Chester MD Homes For Sale

Chester MD Homes For Sale

View all the homes for sale in Chester, MD at a median listing home price for all budget. See pricing and listing details of Chester real estate for sale.

Chester MD Homes For Sale

$309,900
2 Beds ⋅ 2 Baths
Welcome to coastal living in this beautifully updated first-floor, end-unit condo, offering the perfect blend of comfort, convenience, and resort-style amenities in one of Kent Island's most sought-after communities. With no stairs to navigate and handicap-accessible features, this home provides effortless everyday living while enjoying the added privacy and abundant natural light that only an end unit can offer. The beautifully updated kitchen features quartz countertops, a breakfast bar, newer stainless steel appliances, and abundant cabinetry, making it as functional as it is stylish. The adjoining dining area flows seamlessly to the private deck through sliding glass doors, bringing the outdoors in and making entertaining a breeze. HVAC and washer/dryer are less than 4 years old. The spacious primary suite serves as a relaxing retreat with a large walk-in closet and private ensuite bath. A second generously sized bedroom offers exceptional flexibility for guests, a home office, or family visits, while elegant plantation shutters add timeless charm and character to both bedrooms. Life at Bayside is about much more than the home itself. Residents enjoy a truly maintenance-free lifestyle, with exterior maintenance and community upkeep handled by the condominium association, leaving more time to enjoy everything Kent Island has to offer. Community amenities include a clubhouse, swimming pool, fitness center, tennis courts, beautifully landscaped grounds, and Castle Marina just a short walk away. Outdoor enthusiasts will appreciate being only steps from the Cross Island Trail, offering miles of scenic walking and biking paths showcasing the natural beauty of the Chesapeake Bay. Ideally located near waterfront dining, shopping, and local attractions, this home also provides easy access to Route 50 and the Chesapeake Bay Bridge, international airports and coastal beaches, making commuting and travel exceptionally convenient. Where every day feels like a vacation—and the only thing left to maintain is your schedule.

302 Merganser Ct Unit #A, Chester

Listing courtesy of Keller Williams Flagship. Contact:

$225,000
1 Beds ⋅ 1 Baths
Bring your vision to one of the most affordable condos currently available in Queen’s Landing. This one-bedroom, one-bath unit offers approximately 640 square feet and is priced well below its tax-assessed value to reflect its original interior condition, giving buyers the flexibility to update and personalize the space to suit their own style. The condo overlooks Lake Amletto, offering a pleasant water view and the relaxing sound of the nearby fountain, while the Chester River is just a short walk away across the street. One-bedroom units benefit from a lower monthly condominium fee while still enjoying access to the community’s many amenities, including the waterfront pool, clubhouse, fitness center, pickleball and tennis courts, walking paths, marina setting, and beautifully maintained grounds. For a water-oriented lifestyle, boat slips may also be available for purchase or rental within the community, subject to availability. Whether you are looking for an affordable entry into Queen’s Landing, a renovation project, an investment opportunity, or a weekend retreat near the water, this property offers plenty of potential.

26 Queen Anne Way, Chester

Listing courtesy of Realty Navigator. Contact: 4106433404
$998,000
3 Beds ⋅ 3 Baths
Welcome to this stunning 4th floor penthouse Severn condominium with serene bay views! This end unit looks out over the walking trails to the water and trees. The fabulous community center /pool / pier is a short 1 mile walk from your backyard.! This unit also has the largest garage space in the the building, plenty of room for one car and storage, a refrigerator etc. There is also an additional inside storage room. This 2600 Sq Ft home is flooded with natural light and has numerous quality upgrades including custom shiplap in most of the rooms, custom ceiling fans and dining room light fixture, custom built his and hers walk in closets. The primary bath has upgraded tile, shelving for more storage, mulitple shower heads and back and front lit vanity mirrors. The gourmet kitchen is designed to impress, featuring elegant quartz countertops,premium appliances and a Wolfe induction cooktop. The island has been upgraded with shiplap as well. Thoughtful upgrades continue throughout the entire home with custom blinds with remote control, a gas fireplace,9 FT ceilings with tray ceilings in the living room and primary suite. A wet bar has also been added to the dining area.The large primary bedroom comes complete with a sitting area/office with exceptional waterviews. It also offers custom designed his -and -her closets that provide both style and storage. This unique residence offers a peaceful setting where you can relax and enjoy the ever-changing waterfront vistas. Whether you are enjoying your morning coffee or entertaining guests, this home offers the perfect blend of sophistication, comfort, and low maintenance waterfront living.

111 Marshgrass Way Unit #41, Chester

Listing courtesy of Long & Foster Real Estate, Inc.. Contact:

$989,800
5 Beds ⋅ 4 Baths
Coastal luxury living by Laine Street Homes, this exceptional waterfront home offers over 3,000 square feet on 3 levels with 5 bedrooms, 3.5 bathrooms, and stunning water views. Perfectly positioned and thoughtfully designed to capture beautiful sunrises over the water, the home is filled with natural light and showcases panoramic water views from the main living areas and the luxurious primary suite. Designed for both luxury living and entertaining, the open floor plan features 7-inch wide plank flooring, a gas fireplace, entry-level guest suite, and high-end finishes throughout. The gourmet kitchen is the heart of the home, complete with shaker-style cabinetry, quartz countertops, an oversized island, premium ZLINE stainless steel appliances, upgraded custom lighting, and expansive water views. Upstairs, the spacious primary suite offers a peaceful waterfront retreat with a spa-inspired bath featuring a 6-foot tiled walk-in shower with dual shower heads, a built-in bench, double vanities, and generous closet space. Bedroom-level laundry and beautifully finished bathrooms with tile flooring add everyday convenience. Outdoor living is just as impressive, with an expansive rear deck and covered patio overlooking the creek—perfect for enjoying sunrises over the water or relaxing while watching local wildlife. Adding to the sense of privacy, approximately 181 acres of rural land zoned "Countryside District" stretch across the shoreline on the opposite side, preserving the natural views with protected land. For those who enjoy life on the water, this location is hard to beat. Launch a kayak, paddleboard, or small boat from your backyard and reach the Chester River in approximately one mile, with the Chesapeake Bay just 5 to 6 water miles beyond. Enjoy quick access to bay boating while returning home to the calm waters, privacy, and natural beauty of a protected creek. Combining quality craftsmanship, upscale finishes, and an exceptional waterfront setting, this newly completed home offers a rare opportunity to enjoy the best of Maryland's Eastern Shore lifestyle!

203 Riverside Dr, Chester

Listing courtesy of Long & Foster Real Estate, Inc.. Contact: 3019459010
$929,990
2 Beds ⋅ 3 Baths
Welcome to the Chester, a thoughtfully designed home offering 2 bedrooms, 2.5 baths, and a 1-car garage. Scheduled for settlement in December 2026, this home combines modern comfort with functional and stylish living spaces. The main living area features a dry bar and an electric fireplace, creating a warm and inviting atmosphere perfect for both relaxing and entertaining. A dedicated home office with lited French doors provides a private and elegant workspace. The kitchen is designed for both everyday living and convenience, featuring a single oven, microwave, gas cooktop with range hood, dishwasher, pendant lighting, tile backsplash, and quartz countertops. Luxury vinyl plank flooring flows throughout the home, with tile flooring in both full baths. The owner’s bath offers a walk-in shower with a seat and handheld shower wand, double sinks, and quartz countertops, creating a comfortable and functional retreat. For a full list of features for this home please contact our sales representatives. Photos are for illustrative purposes only and may not represent the exact home or finishes available.

102 Boatswain Way Unit #2943, Chester

Listing courtesy of Berkshire Hathaway HomeServices PenFed Realty - OP. Contact: 4102083500
$829,990
2 Beds ⋅ 3 Baths
Welcome to the Chester, a thoughtfully designed home offering 2 bedrooms, 2.5 baths, and a 1-car garage. Scheduled for settlement in December 2026, this home combines modern comfort with functional and stylish living spaces. The main living area features a dry bar and an electric fireplace, creating a warm and inviting atmosphere perfect for both relaxing and entertaining. A dedicated home office with lited French doors provides a private and elegant workspace. The kitchen is designed for both everyday living and convenience, featuring a single oven, microwave, gas cooktop with range hood, dishwasher, pendant lighting, tile backsplash, and quartz countertops. Luxury vinyl plank flooring flows throughout the home, with tile flooring in both full baths. The owner’s bath offers a walk-in shower with a seat and handheld shower wand, double sinks, and quartz countertops, creating a comfortable and functional retreat. For a full list of features for this home please contact our sales representatives. Photos are for illustrative purposes only and may not represent the exact home or finishes available.

102 Boatswain Way Unit #2932, Chester

Listing courtesy of Berkshire Hathaway HomeServices PenFed Realty - OP. Contact: 4102083500
$749,000
4 Beds ⋅ 4 Baths
Experience the best of Kent Island living in this beautifully maintained coastal home, ideally situated in the highly desirable Water's Edge section of Gibson's Grant. Built in 2017, this exceptional residence enjoys unobstructed pond views from the welcoming covered front porch, where you can relax while watching blue herons and other native wildlife. Perfectly positioned just one block from the community's exceptional waterfront amenities, including the Chester River, clubhouse, pool, fitness center, kayak launch, fishing pier, and waterfront pavilion, this home offers the perfect blend of luxury, convenience, and the relaxed lifestyle of Maryland's Eastern Shore. Step inside to discover a bright, thoughtfully designed floor plan where beautiful flooring flows throughout the main level and abundant natural light fills every room. Designed for both everyday living and effortless entertaining, the main level offers exceptional versatility with a spacious flex room that is ideal as a home office, den, sitting room, or additional living space, along with a convenient powder room for guests. The heart of the home is the expansive open-concept living area, where the spacious family room, dining area, and beautifully appointed kitchen come together seamlessly. The kitchen features a large center island with abundant seating and workspace, while the family room is highlighted by a beautiful gas fireplace. Just beyond, the brand-new screened porch opens to your own private backyard oasis featuring a beautifully landscaped paver patio, a tranquil ornamental pond with a cascading waterfall, full privacy fencing perfect for pets, and an irrigation system to keep the grounds looking their best. Designed for the ease of first-floor living, the main level features a spacious primary suite privately situated at the rear of the home. The luxurious ensuite bath includes a relaxing Jacuzzi soaking tub, while a second main-level bedroom offers its own private full bath, making it ideal for guests or multigenerational living. The staircase to the upper level is thoughtfully tucked toward the rear of the home, enhancing the home's functional layout. Upstairs, you'll find two generously sized bedrooms and a beautifully appointed full bath, providing comfortable accommodations for family and guests. Completing the home is a spacious rear-entry two-car garage with plenty of room for parking and storage, plus a custom-built workspace perfect for DIY enthusiasts, hobbyists, or woodworking projects. An approximately four-foot-high conditioned crawl space with interior access provides exceptional additional storage. Recent improvements include a brand-new HVAC system, brand-new screened porch, one-year-old oven, and new washer and dryer, allowing you to move in with confidence. Residents of Gibson's Grant enjoy resort-style amenities, including a clubhouse, outdoor pool, fitness center, waterfront pavilion, kayak launch, fishing pier, water access, and direct access to the Cross Island Trail. Tucked behind a peaceful nature preserve just off Route 50, this sought-after waterfront community offers the perfect balance of tranquility and convenience. Located just moments from the Chesapeake Bay Bridge, the home provides an easy commute while placing you minutes from waterfront dining, marinas, shopping, parks, and local entertainment. Beautifully maintained, thoughtfully updated, and ideally located in one of Kent Island's most desirable neighborhoods, this exceptional home offers the perfect opportunity to embrace luxury coastal living on Maryland's Eastern Shore. Schedule your private showing today! Mortgage savings may be available for buyers of this listing.

134 Richard Ingle Way, Chester

Listing courtesy of Redfin Corp. Contact: 3016586186
$895,000
3 Beds ⋅ 3 Baths
Welcome to Southwind, one of Kent Island's most desirable waterfront communities, where peaceful surroundings and an exceptional lifestyle come together. Perfectly positioned on 1.22 beautifully landscaped acres with water views, this inviting single-level home offers the comfort, space, and amenities you've been searching for. Inside, you'll find three spacious bedrooms and three beautifully updated full baths, creating a home that is both stylish and comfortable. Freshly painted throughout, with newly refinished hardwood floors and plush new carpeting in the bedrooms, every room feels bright, fresh, and move-in ready. The heart of the home is the welcoming kitchen, featuring gleaming granite countertops, crisp white cabinetry, a generous pantry with charming French doors, peninsula seating for casual meals and conversation, a vaulted breakfast area with a dramatic palladium window showcasing beautiful water views, and brand-new stainless steel range and refrigerator. Whether you're preparing dinner or gathering with family and friends, this space is designed to bring everyone together. The adjoining family room is warm and inviting, centered around a cozy propane fireplace and accented by custom built-in bookshelves that add both charm and functionality. A sliding glass door opens directly to the slate patio, creating an effortless connection between indoor and outdoor living. Just off the main living area, the light-filled dining room is surrounded by large windows that frame lovely water views, creating the perfect backdrop for everyday meals and special occasions. A versatile bonus sunroom offers even more living space and can easily serve as a cozy den, home office, or additional bedroom to fit your needs. Step outside to enjoy the fenced backyard and slate patio, where a remote-operated awning provides welcome shade at the touch of a button, making it the perfect spot for morning coffee, evening sunsets, or weekend barbecues. Car enthusiasts, hobbyists, and those needing extra space will appreciate the oversized four-car garage. Above, an expansive unfinished area offers endless possibilities. Already plumbed for a future bath, it's ready to become a guest suite, home office, recreation room, or whatever your imagination inspires. Energy efficiency is another standout feature, with owned solar panels and two Tesla Powerwall storage batteries helping to keep utility costs remarkably low while providing added peace of mind. Living in Southwind means more than owning a beautiful home—it's embracing a waterfront lifestyle. Residents enjoy access to the community boat launch, waterfront clubhouse, boat storage lot, pickleball and tennis courts, and scenic nature trail along the water. Whether you're launching your boat for a day on the Chesapeake Bay, enjoying an evening stroll by the shoreline, or simply relaxing at home while taking in the tranquil water views, this property offers the perfect blend of comfort, community, and coastal living.

2810 Harvest Ct, Chester

Listing courtesy of Blackwell Real Estate, LLC. Contact: 4432214120
$345,000
3 Beds ⋅ 2 Baths
Welcome to 1609 Crab Alley Drive, a charming three-bedroom, one-and-a-half-bath rancher offering comfortable one-level living and lovely water views. Inside, hardwood flooring adds warmth and character, while the oversized picture window fills the front living room with natural light. The spacious backyard is made for summertime enjoyment, featuring an above-ground pool with plenty of additional room for entertaining, gardening, pets, or play. A large detached two-car garage provides exceptional space for vehicles, storage, hobbies, or a workshop. With its classic curb appeal, generous outdoor space, and convenient Chester location, this inviting home is ready for its next chapter.

1609 Crab Alley Dr, Chester

Listing courtesy of Paul Wesley Real Estate. Contact: 7032822709
$382,750
3 Beds ⋅ 2 Baths
OPEN HOUSE this Saturday 7/25 - 9am to 11am! ALL NEW Carpet & flooring, fresh custom paint, granite countertops and newer appliances! Welcome to one of the most desirable homes in the Bridgepointe community! This beautifully maintained END UNIT home offers added privacy, abundant natural light and a thoughtfully designed floor plan that perfectly blends comfort and convenience. Featuring one of the community's most sought after amenities... an ATTACHED GARAGE with interior access! This exceptional home also offers a first floor Primary bedroom & full bath, first floor laundry, making it ideal for guests, multigenerational living, a home office, or anyone seeking the convenience of main level living. Step inside to discover bright, inviting living spaces enhanced by the additional windows that only an end unit can provide. The open concept layout creates an effortless flow for both everyday living and entertaining. The well-appointed kitchen opens to the main living areas while the spacious bedrooms provide flexibility for family, guests, or work-from-home needs. Enjoy the best of low maintenance living in the highly desirable Bridgepointe community, with easy access to shopping, dining, parks, schools, marinas, and the Chesapeake Bay. Commuters will appreciate the close proximity to the Bay Bridge, Route 50, Annapolis and Maryland's Eastern Shore. Whether you are searching for a full-time residence or a weekend retreat, this exceptional home offers the perfect combination of location, lifestyle, and value.

2004 Bridgepointe Dr, Chester

Listing courtesy of RE/MAX Executive. Contact: 4432741900
$989,000
5 Beds ⋅ 4 Baths
Discover the extraordinary waterfront oasis of 2702 Sherman Dr. in Chester. This remarkable residence, featuring 5 bedrooms, 2 full bathrooms, and 2 half bathrooms, has undergone a stunning renovation, creating a haven of luxury and serenity on a peaceful street. Every detail of this home has been impeccably updated, from the oversized windows to the modernized bathrooms. However, the true centerpiece is the fully equipped gourmet kitchen, a masterpiece of design. A magnificent 10-foot Quartz center island takes center stage, surrounded by pristine cabinets, state-of-the-art appliances, and exquisite marble countertops. To top it off, the kitchen also boasts its own wet bar with a built-in beverage cooler. The open-concept layout seamlessly connects the kitchen to the living space, with a mesmerizing wall of oversized windows that offer breathtaking views of the expansive waterfront and private pier. Convenience is a priority in this home, with a three-car pull-through garage and a pier equipped with boat lift as well as dual Jetski lift for easy access to the water. Outdoor enjoyment is a given, with two waterfront decks, a screened-in patio, and a private en-suite deck for moments of relaxation. Privacy and the feeling of island-style living are abundant here. Located in the heart of Kent Island, this property provides effortless access to luxury dining options, waterfront restaurants, lively dock bars, and island-style entertainment. All while, being just 2 miles away from the Chesapeake Bay Bridge means seamless travel by land or sea. Welcome to your dream home, here on Kent Island where tranquility and luxury converge with Maryland's Eastern Shore and the Chesapeake Bay.

2702 Sherman Dr, Chester

Listing courtesy of Samson Properties. Contact: 7033788810
$999,990
3 Beds ⋅ 3 Baths
Welcome to the Severn, a beautifully designed home offering 3 bedrooms, 2.5 baths, and a 1-car garage. Scheduled for settlement in October 2026, this home blends modern comfort with functional living spaces. The main living area features a dry bar and an electric fireplace, creating a warm and inviting setting for everyday living and entertaining. The owner’s suite includes a private sitting room and large walk-in closets, offering a spacious and relaxing retreat. The kitchen is designed for both style and convenience, featuring a single oven, microwave, gas cooktop with range hood, dishwasher, pendant lighting, tile backsplash, and quartz countertops. Laminate flooring flows throughout the home, with tile flooring in both full baths. The owner’s bath is thoughtfully designed with a walk-in shower featuring a seat and handheld shower wand, double sinks, and quartz countertops for added comfort and functionality. For a full list of features for this home please contact our sales representatives. Photos are for illustrative purposes only and may not represent the exact home or finishes available.

110 Boatswain Way Unit #3044, Chester

Listing courtesy of Berkshire Hathaway HomeServices PenFed Realty - OP. Contact: 4102083500
$629,990
2 Beds ⋅ 3 Baths
Welcome to the Magothy, a beautifully designed home offering 2 bedrooms, 2.5 baths, and a 1-car garage. This home blends modern comfort with functional living spaces. The main living area features a dry bar and an electric fireplace, creating a warm and inviting setting for everyday living and entertaining. The owner’s suite includes a private sitting room and large walk-in closets, offering a spacious and relaxing retreat. The kitchen is designed for both style and convenience, featuring a single oven, microwave, gas cooktop with range hood, dishwasher, pendant lighting, tile backsplash, and quartz countertops. Laminate flooring flows throughout the home, with tile flooring in both full baths. The owner’s bath is thoughtfully designed with a walk-in shower featuring a seat and handheld shower wand, double sinks, and quartz countertops for added comfort and functionality. For a full list of features for this home please contact our sales representatives. Photos are for illustrative purposes only and may not represent the exact home or finishes available.

102 Boatswain Way Unit #2911, Chester

Listing courtesy of Berkshire Hathaway HomeServices PenFed Realty - OP. Contact: 4102083500
$974,990
5 Beds ⋅ 5 Baths
Welcome to the Tuscaloosa, a beautifully designed home that blends an open-concept floorplan with warm Farmhouse-inspired style, creating the perfect balance of comfort and functionality. Projected for November 2026 settlement, this spacious home features 5 bedrooms, 4.5 bathrooms, and a 3-car garage, offering plenty of room for everyday living, entertaining, and hosting overnight guests. Designed with versatility in mind, the Tuscaloosa includes two primary suites, making it an ideal layout for multi-generational living or accommodating long-term guests. The inviting fireplace serves as a cozy focal point for the main living area, while the screened patio provides the perfect outdoor retreat for enjoying fresh air in comfort throughout the seasons. Thoughtful design and quality craftsmanship come together to create a home that is both stylish and functional. For a complete list of included features and finishes, please contact our sales representatives. Photos are for illustrative purposes only and may not represent the exact home or finishes available. Welcome to a new luxury active adult 55+ community on Maryland's Chesapeake Bay. Discover the amenity-filled, resort-style experience within 45 miles of Washington DC and Baltimore. Residents can take advantage of the community's 24,000 sq. ft. clubhouse with indoor & outdoor pools, a state-of-the-art fitness center, and multiple tennis and pickleball courts. With a full-time lifestyle director on site the community also features a well-maintained calendar of activities such as walking club, indoor and outdoor yoga sessions, mahjong club, kayaking, pickleball and more. Kent Island life is about making friends and enjoying the company of people who have worked hard and now want to enjoy all that a luxury 55+ community has to offer. Located steps from the water and minutes from Annapolis, the location also offers quick access to Rt. 50. Enjoy the convenience of nearby dining and shopping options together with the quaint charm of a small town.

323 Kingfisher Ln, Chester

Listing courtesy of Berkshire Hathaway HomeServices PenFed Realty - OP. Contact: 4102083500
$789,990
4 Beds ⋅ 3 Baths
Welcome to the Simone, a beautifully designed home offering 4 bedrooms, 3 baths, and a 2-car garage. This home combines thoughtful design with comfortable living spaces ideal for both everyday life and entertaining. The main living area features a cozy one-story fireplace, creating a warm and inviting focal point. A dedicated home office provides a private space for work or study, while the screened patio extends your living area outdoors—perfect for relaxing or hosting guests. The kitchen is designed for both style and function, featuring a single oven, microwave, gas cooktop with range hood, dishwasher, French door refrigerator, pendant lighting, tile backsplash, and quartz countertops. Quartz is also featured in the owner’s bath for a cohesive and elegant finish. Luxury vinyl plank flooring runs throughout the foyer, extended foyer, kitchen, dining area, great room, bedroom 2, owner’s suite, HovHall, loft/second floor, and bedrooms 3 and 4. Tile flooring is featured in all full baths and the laundry room. The owner’s bath includes a walk-in shower with a seat and handheld shower wand, along with a double-sink vanity for added comfort and convenience. For a full list of features for this home please contact our sales representatives. Photos are for illustrative purposes only and may not represent the exact home or finishes available. Welcome to a new luxury active adult 55+ community on Maryland's Chesapeake Bay. Discover the amenity-filled, resort-style experience within 45 miles of Washington DC and Baltimore. Residents can take advantage of the community's 24,000 sq. ft. clubhouse with indoor & outdoor pools, a state-of-the-art fitness center, and multiple tennis and pickleball courts. With a full-time lifestyle director on site the community also features a well-maintained calendar of activities such as walking club, indoor and outdoor yoga sessions, mahjong club, kayaking, pickleball and more. Kent Island life is about making friends and enjoying the company of people who have worked hard and now want to enjoy all that a luxury 55+ community has to offer. Located steps from the water and minutes from Annapolis, the location also offers quick access to Rt. 50. Enjoy the convenience of nearby dining and shopping options together with the quaint charm of a small town.

723 Warbler Way, Chester

Listing courtesy of Berkshire Hathaway HomeServices PenFed Realty - OP. Contact: 4102083500
$839,990
4 Beds ⋅ 3 Baths
Welcome to the Simone, a beautifully designed home offering 4 bedrooms, 3 baths, and a 2-car garage. This home combines thoughtful design with comfortable living spaces ideal for both everyday life and entertaining. The main living area features a cozy one-story fireplace, creating a warm and inviting focal point. A dedicated home office provides a private space for work or study, while the screened patio extends your living area outdoors—perfect for relaxing or hosting guests. The kitchen is designed for both style and function, featuring a single oven, microwave, gas cooktop with range hood, dishwasher, French door refrigerator, pendant lighting, tile backsplash, and quartz countertops. Quartz is also featured in the owner’s bath for a cohesive and elegant finish. Luxury vinyl plank flooring runs throughout the foyer, extended foyer, kitchen, dining area, great room, bedroom 2, owner’s suite, HovHall, loft/second floor, and bedrooms 3 and 4. Tile flooring is featured in all full baths and the laundry room. The owner’s bath includes a walk-in shower with a seat and handheld shower wand, along with a double-sink vanity for added comfort and convenience. For a full list of features for this home please contact our sales representatives. Photos are for illustrative purposes only and may not represent the exact home or finishes available. Welcome to a new luxury active adult 55+ community on Maryland's Chesapeake Bay. Discover the amenity-filled, resort-style experience within 45 miles of Washington DC and Baltimore. Residents can take advantage of the community's 24,000 sq. ft. clubhouse with indoor & outdoor pools, a state-of-the-art fitness center, and multiple tennis and pickleball courts. With a full-time lifestyle director on site the community also features a well-maintained calendar of activities such as walking club, indoor and outdoor yoga sessions, mahjong club, kayaking, pickleball and more. Kent Island life is about making friends and enjoying the company of people who have worked hard and now want to enjoy all that a luxury 55+ community has to offer. Located steps from the water and minutes from Annapolis, the location also offers quick access to Rt. 50. Enjoy the convenience of nearby dining and shopping options together with the quaint charm of a small town.

715 Warbler Way, Chester

Listing courtesy of Berkshire Hathaway HomeServices PenFed Realty - OP. Contact: 4102083500
$2,400,000
4 Beds ⋅ 4 Baths
Discover an exquisite Mediterranean-style residence nestled in the prestigious Southwind community, where luxury meets comfort while enjoying breathtaking sunset views. This stunning 4-bedroom, 3.5-bathroom home boasts 4,331 sq. ft. The gourmet kitchen features high-end stainless steel appliances, including a built-in microwave, wall oven, and a sleek cooktop, ensuring culinary excellence. Step outside to your private oasis, where a concrete pool invites relaxation amidst lush landscaping on a generous 1.2-acre lot that includes a covered built in Lynx grill and bar seating. Enjoy direct access to Cox Creek, complete with a private dock for fishing, kayaking, or simply soaking in the serene water views. With a double sided fireplace and three tankless water heater, this home combines elegance with modern convenience, making it a true sanctuary. The main living room features sky high ceilings and a wet bar making hosting a snap and flows into the added sunroom that features heated tile flooring. And the three season room off the back is the perfect gathering space with a wall of sliders to maximize the view. Meticulously maintained and thoroughy enjoyed by the original owners. The expansive rear yard and rip-rap shoreline enhance the outdoor experience, while the community amenities, including a beach, tennis/basketball courts, and fishing pier and boat launch, offer an exclusive lifestyle on Maryland's Eastern Shore.

2882 Cox Neck Rd, Chester

Listing courtesy of Wilson Realty & Staging LLC. Contact: 4103042250
$929,990
3 Beds ⋅ 3 Baths
Welcome to the Kerr, a beautifully designed home offering 3 bedrooms, 3 baths, and a 3-car garage. This home combines an open-concept layout with thoughtful design for both comfort and functionality. The main living area features a cozy fireplace with mantel and hearth, creating a warm and inviting focal point. A dedicated home office provides a private space for productivity, while the screened patio extends the living area outdoors—perfect for entertaining or relaxing. The kitchen is equipped for both style and performance, featuring a single oven, microwave, gas cooktop with range hood, dishwasher, French door refrigerator, pendant lighting, tile backsplash, and quartz countertops. Quartz is also featured in the owner’s bath for a cohesive, elegant finish. Hardwood flooring flows throughout the foyer, extended foyer, HovHall, kitchen, dining area, great room, home office, bedrooms 2, the primary suite, loft, and second floor, while tile is featured in all full baths and the laundry room. The primary bath includes a walk-in shower with seat and handheld shower wand and a double-sink vanity for added convenience and luxury. For a full list of features for this home, please contact our sales representatives. Photos are for illustrative purposes only and may not represent the exact home or finishes available. Welcome to a new luxury active adult 55+ community on Maryland's Chesapeake Bay. Discover the amenity-filled, resort-style experience within 45 miles of Washington DC and Baltimore. Residents can take advantage of the community's 24,000 sq. ft. clubhouse with indoor & outdoor pools, a state-of-the-art fitness center, and multiple tennis and pickleball courts. With a full-time lifestyle director on site the community also features a well-maintained calendar of activities such as walking club, indoor and outdoor yoga sessions, mahjong club, kayaking, pickleball and more. Kent Island life is about making friends and enjoying the company of people who have worked hard and now want to enjoy all that a luxury 55+ community has to offer. Located steps from the water and minutes from Annapolis, the location also offers quick access to Rt. 50. Enjoy the convenience of nearby dining and shopping options together with the quaint charm of a small town.

532 Warbler Way, Chester

Listing courtesy of Berkshire Hathaway HomeServices PenFed Realty - OP. Contact: 4102083500
$829,990
2 Beds ⋅ 3 Baths
Welcome to the Chester, a thoughtfully designed home offering 2 bedrooms, 2.5 baths, and a 1-car garage. Scheduled for settlement in December 2026, this home combines modern comfort with functional and stylish living spaces. The main living area features a dry bar and an electric fireplace, creating a warm and inviting atmosphere perfect for both relaxing and entertaining. A dedicated home office with lited French doors provides a private and elegant workspace. The kitchen is designed for both everyday living and convenience, featuring a single oven, microwave, gas cooktop with range hood, dishwasher, pendant lighting, tile backsplash, and quartz countertops. Luxury vinyl plank flooring flows throughout the home, with tile flooring in both full baths. The owner’s bath offers a walk-in shower with a seat and handheld shower wand, double sinks, and quartz countertops, creating a comfortable and functional retreat. For a full list of features for this home please contact our sales representatives. Photos are for illustrative purposes only and may not represent the exact home or finishes available.

102 Boatswain Way Unit #2933, Chester

Listing courtesy of Berkshire Hathaway HomeServices PenFed Realty - OP. Contact: 4102083500
$749,990
2 Beds ⋅ 3 Baths
Welcome to the Chester, a thoughtfully designed home offering 2 bedrooms, 2.5 baths, and a 1-car garage. Scheduled for settlement in October 2026, this home combines modern comfort with functional living spaces. The heart of the home features a dry bar and an electric fireplace, creating a warm and inviting atmosphere. A dedicated home office with lited French doors provides a stylish and private workspace. The kitchen is designed for both everyday living and entertaining, featuring a single oven, microwave, gas cooktop with range hood, dishwasher, pendant lighting, tile backsplash, and quartz countertops. Luxury vinyl plank flooring flows throughout the home, with tile flooring in both full baths. The owner’s bath offers a walk-in shower with seat and handheld shower wand, double sinks, and quartz countertops for added convenience and style. For a full list of features for this home, please contact our sales representatives. Photos are for illustrative purposes only and may not represent the exact home or finishes available.

110 Boatswain Way Unit #3042, Chester

Listing courtesy of Berkshire Hathaway HomeServices PenFed Realty - OP. Contact: 4102083500
$929,990
3 Beds ⋅ 3 Baths
Welcome to the Kerr, a beautifully designed home offering 3 bedrooms, 3 baths, and a 3-car garage. This home combines an open-concept layout with thoughtful design for both comfort and functionality. The main living area features a cozy fireplace with mantel and hearth, creating a warm and inviting focal point. A dedicated home office provides a private space for productivity, while the screened patio extends the living area outdoors—perfect for entertaining or relaxing. The kitchen is equipped for both style and performance, featuring a single oven, microwave, gas cooktop with range hood, dishwasher, French door refrigerator, pendant lighting, tile backsplash, and quartz countertops. Quartz is also featured in the owner’s bath for a cohesive, elegant finish. Hardwood flooring flows throughout the foyer, extended foyer, HovHall, kitchen, dining area, great room, home office, bedrooms 2, the primary suite, loft, and second floor, while tile is featured in all full baths and the laundry room. The primary bath includes a walk-in shower with seat and handheld shower wand and a double-sink vanity for added convenience and luxury. For a full list of features for this home, please contact our sales representatives. Photos are for illustrative purposes only and may not represent the exact home or finishes available. Welcome to a new luxury active adult 55+ community on Maryland's Chesapeake Bay. Discover the amenity-filled, resort-style experience within 45 miles of Washington DC and Baltimore. Residents can take advantage of the community's 24,000 sq. ft. clubhouse with indoor & outdoor pools, a state-of-the-art fitness center, and multiple tennis and pickleball courts. With a full-time lifestyle director on site the community also features a well-maintained calendar of activities such as walking club, indoor and outdoor yoga sessions, mahjong club, kayaking, pickleball and more. Kent Island life is about making friends and enjoying the company of people who have worked hard and now want to enjoy all that a luxury 55+ community has to offer. Located steps from the water and minutes from Annapolis, the location also offers quick access to Rt. 50. Enjoy the convenience of nearby dining and shopping options together with the quaint charm of a small town.

540 Warbler Way, Chester

Listing courtesy of Berkshire Hathaway HomeServices PenFed Realty - OP. Contact: 4102083500
$719,900
2 Beds ⋅ 2 Baths
Experience the ease of elegant one-level living in this exceptional home, located in one of Maryland's premier 55+ active adult communities on the Chesapeake Bay. Designed for both comfort and style, this beautifully appointed residence features a three-car tandem garage with an EV charger, a spacious screened porch, a cozy gas fireplace, upgraded trim and designer feature walls. Thoughtful enhancements include Hunter Douglas plantation shutters, custom California Closets in the owner's suite and second bedroom, modern ceiling fans throughout, reverse osmosis water filtration, and professionally treated energy-efficient windows that reduce UV rays and heat for year-round comfort. Beyond your front door, enjoy a true resort-style lifestyle just 45 miles from both Washington, D.C. and Baltimore. The impressive 24,000-square-foot clubhouse offers indoor and outdoor pools, a state-of-the-art fitness center, tennis and pickleball courts, and an active social calendar led by a full-time lifestyle director. From kayaking, yoga, and walking clubs to mahjong, pickleball, and countless social events, there is something for everyone. Located just steps from the waterfront and minutes from historic Annapolis, this vibrant Kent Island community combines small-town charm with exceptional convenience. Enjoy easy access to Route 50, along with nearby shopping, dining, and everything that makes Chesapeake Bay living so special.

121 Merlin Dr, Chester

Listing courtesy of Coldwell Banker Realty. Contact: 4102638686
$550,000
2 Beds ⋅ 3 Baths
Welcome to resort-style living at K. Hovnanian's Four Seasons at Kent Island — one of the Eastern Shore's premier 55+ waterfront communities on the Chesapeake Bay. This Magothy model condo offers approximately 2003 sq. ft. of thoughtfully designed single-level living, featuring 2 bedrooms — each with its own attached bathroom — plus a powder room for guests, a private home office with French doors, oversized walk-in closets in both bedrooms, a dry bar, and a private deck to unwind and take in the coastal air. A private climate-controlled storage room and a 1-car private garage complete the low-maintenance, lock-and-leave lifestyle this community is known for. Residents enjoy access to a beautifully appointed in-building community room, perfect for relaxing, entertaining, or working from somewhere other than your unit. Your HOA dues unlock access to the award-winning 24,000-sq.-ft. Chester House clubhouse — the true heart of the community — with indoor and outdoor swimming pools, a fully equipped fitness center, yoga studio, demonstration kitchen, library, billiards and game room, and a grand ballroom for private events. Outside, residents enjoy lighted tennis, pickleball, and bocce courts, a dog park, gas and wood-burning fire pits, a waterside tiki bar, and 4.3+ miles of walking and biking trails connecting to the Cross Island Trail. Water lovers will love the 450-foot community pier on the Chester River with boat slips, plus canoe and kayak launch and storage — all just steps from the clubhouse. Live entertainment and community life never stop, with a full-time lifestyle director curating year-round programming: walking club, water aerobics, Zumba, mahjong, kayaking outings, holiday parties, and concerts and movie nights at the community's outdoor waterfront amphitheater. This is more than a home — it's a resort lifestyle every single day. Minutes to Kent Island's shops, waterfront dining, and Queenstown Premium Outlets, with easy access to the Bay Bridge for trips to Annapolis, Baltimore, and Washington D.C. Don't wait to start living the Four Seasons lifestyle — schedule your private showing today.

230 Switchgrass Way Unit #12, Chester

Listing courtesy of Real Broker, LLC - Chester. Contact: 8554500442
$535,000
5 Beds ⋅ 3 Baths
Welcome to 205 Anchor Lane, a spacious and versatile home in the desirable Castle Marina community of Chester! Situated on a generous half-acre lot with no HOA, this oversized split foyer offers the flexibility, space, and location that today's buyers are looking for. With 5 bedrooms and 3 full bathrooms, this home provides room for everyone. The lower level offers excellent potential for multigenerational living, guest accommodations, or a future in-law suite. Fresh carpet, luxury vinyl plank flooring, and updated bathrooms create a move-in ready feel while still leaving opportunities to add your own personal touches and build equity. The functional floor plan offers multiple living spaces, a two-car garage, and abundant storage throughout. Outside, the expansive yard provides plenty of room for entertaining, gardening, pets, or simply enjoying the outdoors. Ideally located within walking distance to local dining, Castle Marina, and the Cross Island Trail, you'll love the convenience of enjoying the Kent Island lifestyle right from your doorstep. Public sewer service and well water add to the property's appeal. Whether you're searching for extra space, a home that can accommodate extended family, or simply a great value in a sought-after location, 205 Anchor Lane delivers endless possibilities.

205 Anchor Ln, Chester

Listing courtesy of Samson Properties. Contact: 7033788810
$629,900
3 Beds ⋅ 2 Baths
This 3 bedroom 2 full bath brick rancher is located 1.88 for plenty of privacy and plenty of room to expand. Not many large lots left in this community, check with county for very possible sub dividing for 2 additional lots. Home is in need of updating with lots of potential to add your own touch and design. More pictures coming soon. Currently on septic but sewer is available.

315 Bentons Pleasure Rd, Chester

Listing courtesy of Douglas Realty LLC. Contact: (866) 987-3937
$749,900
4 Beds ⋅ 3 Baths
Why wait for new construction when you can move right into this beautiful Simone model in the highly sought-after Four Seasons at Kent Island? This spacious home offers 4 bedrooms, 3 full baths, and the perfect blend of comfort, style, and low-maintenance living.The open floor plan makes everyday living and entertaining easy, with a bright kitchen featuring quartz countertops, stainless steel appliances, a large center island, and plenty of space to gather with family and friends. The cozy gas fireplace adds warmth and charm to the main living area, while the screened patio is the perfect spot to relax with your morning coffee or unwind at the end of the day.The large primary suite offers a peaceful retreat with a spacious walk-in closet, double vanities, and a walk-in shower. Additional bedrooms AND an office provide plenty of room for guests, hobbies, or just about anything you can think of and the convenient mud room adds extra functionality.Living in Four Seasons at Kent Island means enjoying an incredible lifestyle. Residents have access to a stunning 24,000-square-foot clubhouse featuring indoor and outdoor pools, a state-of-the-art fitness center, tennis and pickleball courts, and a full-time lifestyle director who keeps the social calendar full of activities including walking clubs, yoga, mahjong, kayaking, pickleball, and more.Kent Island living is all about making new friends, staying active, and enjoying the lifestyle you've worked hard to achieve. Come see why so many people are proud to call Four Seasons home. And if that wasn't enough of a reason to check this out.....the seller will pay the $4000 capital contribution fee with a full price offer!!

233 Peregrine Dr, Chester

Listing courtesy of Rosendale Realty. Contact: 4107580333
$380,000
3 Beds ⋅ 2 Baths
Welcome to this beautifully situated two-story townhome overlooking the tranquil pond in the highly desirable Bridgepointe community on Kent Island. Enjoy an exceptional location with convenient location to Route 50 and just minutes from waterfront dining, Kent Narrows, the Cross Island Trail, public boat ramps, parks, shopping, medical facilities, and more. Experience the perfect blend of comfort, convenience, and the relaxed Eastern Shore lifestyle. Designed for easy everyday living, the bright, open floor plan seamlessly connects the kitchen, dining area, and living room, where a cozy gas fireplace creates a warm and relaxing space. The adjoining spacious sunroom showcases tranquil pond views, providing the perfect backdrop for morning coffee, quiet evenings, or entertaining guests. The main level also features a desirable first-floor primary suite with a walk-in closet, private access to the sunroom, and an en-suite bath complete with a relaxing Jacuzzi tub and separate walk-in shower. A flexible bonus room with a laundry area and French door access offers endless possibilities as a home office, den, additional bedroom, craft room, or fitness space. Upstairs, two generously sized bedrooms and a full bath provide comfortable accommodations for family and visitors. As an added bonus, a brand-new roof is currently being installed by the HOA, offering peace of mind and added value for the new owner. Whether you're looking for a full-time residence, a weekend getaway, or a low-maintenance retreat, this exceptional pond front home offers the very best of Kent Island living. Don't miss this rare opportunity—it's more than a home, it's a lifestyle!

6010 Bridgepointe Dr, Chester

Listing courtesy of Rosendale Realty. Contact: 4107580333
$2,840,000
3 Beds ⋅ 2 Baths
Rare Find - 2 houses on one waterfront property! Each with unobstructed views of the water! Privacy without isolation. This will change your mind if you think you need 5 acres or more to have wide open spaces and not have neighbors breathing down your neck! Discover a captivating blend of traditional charm in the vintage cape cod - the main 3-bedroom, 2-bathroom residence, recently updated in spring 2026. Nestled in a serene rural setting, this home boasts picturesque views along the banks of Cox Creek, offering panoramic western vistas that will take your breath away, especially as the sun sets on the horizon. Step inside to find a thoughtfully designed interior featuring rich wood floors and upgraded countertops that elevate the kitchen, a home perfect for gatherings. The cozy living room, complete with a brick fireplace and mantel, invites warmth and relaxation. Enjoy the convenience of an entry-level bedroom and a traditional floor plan that flows seamlessly throughout. The exterior is equally impressive, featuring a private beach and a circular gravel driveway that accommodates ample parking. With 548 feet of waterfrontage, indulge in fishing, boating, or simply soaking in the tranquil surroundings. The property includes a private dock with electric hoist and ramp, making water access effortless. Additional highlights include a guest house(2BR, 1.5 BA, KT,screened porch) and a storage building providing versatility for equipment or hobbies. The secluded parcel offers year-round access, ensuring your retreat is always within reach. This home is not just a residence; it's a lifestyle waiting to be embraced. Don't miss the opportunity to make this serene haven your own! Less than 30 minutes to Annapolis, 50 minutes to Baltimore or DC.. Convenient to area restaurants and points of interest. Not under subdivision restrictions. Perfect for multi-generational living, private guest quarters, or possible rental income. Room for expansion of living spaces, outdoor sports court, horseshoes, bocci, or garden. Former waterside pool could be revitalized, subject to county approval.

300 Woods Point Rd, Chester

Listing courtesy of Tidewater Properties. Contact:

$490,000
2 Beds ⋅ 3 Baths
Welcome to 1000 Herons Nest Way #23, an exceptional former model home located in the first phase of condominiums within the highly desirable Four Seasons at Kent Island. This beautiful 2-bedroom, 2.5-bath residence combines designer finishes, thoughtful upgrades, and a peaceful natural setting to create the perfect low-maintenance retreat. From the moment you enter, you'll appreciate the bright, open floor plan, gorgeous luxury vinyl plank flooring, and the seamless flow between the kitchen, dining, and living spaces—ideal for entertaining while still offering comfortable, defined living areas. The gourmet kitchen opens effortlessly into the main living space, while the dedicated home office features custom built-in cabinetry, display shelving, and accent lighting, creating an inviting workspace or library. Throughout the home you'll find quality upgrades including plantation shutters in both bedrooms, custom closet organization systems, ceiling fans, and a built-in wireless audio system with a Samsung Frame TV, blending everyday comfort with modern convenience. The spacious primary suite offers a relaxing escape, while the thoughtfully designed split-bedroom layout provides privacy for overnight guests. One of this home's most captivating features is the private balcony overlooking protected wooded surroundings, where you'll enjoy peaceful mornings with coffee while watching deer, birds, and the abundant wildlife that make Kent Island so special. Just outside your door, enjoy convenient access to the Cross Island Trail, nearby Macum Creek, and community kayak storage—perfect for embracing the Eastern Shore lifestyle. Residents of Four Seasons at Kent Island enjoy a truly carefree lifestyle with exterior maintenance, landscaping, and common areas maintained by the HOA, making it easy to lock the door and travel without worry. Resort-style amenities include a stunning clubhouse, indoor and outdoor pools, fitness center, pickleball and tennis courts, walking trails, and an active calendar of clubs and social events. Beautifully upgraded, impeccably maintained, and ideally situated, this former model home offers a rare opportunity to enjoy resort-style living surrounded by the natural beauty of Kent Island.

1000 Herons Nest Way Unit #23, Chester

Listing courtesy of Samson Properties. Contact: 7033788810
$355,000
3 Beds ⋅ 3 Baths
Adorable is the perfect word to describe this beautifully maintained townhome! Freshly painted and featuring a new roof and skylights (2025), this inviting home offers over 1,600 square feet of comfortable living space with three bedrooms, two full baths, and one-half bath. The main level showcases vaulted ceilings with skylights that fill the home with natural light, creating a bright and airy atmosphere. The open-air plan seamlessly connects the spacious living room and dining area, with room to comfortably accommodate four to six guests, making it ideal for both everyday living and entertaining. Step outside to the private porch overlooking a picturesque pond, where you can relax and enjoy the peaceful sound of the fountain. The main-level primary suite offers a walk-in closet, walk-in shower, and private access to the porch—your own tranquil retreat. The bright, open kitchen features abundant windows and space for a cozy breakfast table, creating the perfect spot to enjoy your morning coffee while taking in the views. Additional highlights include a one-car garage, convenient storage space off the porch, and low HOA fees compared to most communities. Ideally located just minutes from shopping, restaurants, churches, the Bay Bridge, and everyday conveniences, this charming townhome offers the perfect combination of comfort, style, and convenience. Don't miss the opportunity to make this wonderful home your own!

7013 Bridgepointe Dr, Chester

Listing courtesy of Coldwell Banker Realty. Contact: kelly.thompson@cbmove.com
$749,000
3 Beds ⋅ 2 Baths
Coastal cottage charm meets waterfront living on picturesque Crab Alley Creek. Offering 120 feet of shoreline and direct access to the Eastern Bay, this beautifully maintained home combines privacy, convenience, and the very best of the Chesapeake lifestyle. A pier permit already in hand provides an exciting opportunity for the next owner to further enhance their waterfront experience. This move-in-ready residence features 3 bedrooms, 2 full baths, and a versatile bonus room that can serve as a home office, guest room, or potential 4th bedroom. Meticulously updated and lovingly maintained throughout, pride of ownership is evident at every turn. Thoughtful upgrades create a warm and inviting atmosphere, including under-cabinet lighting and dimmer switches throughout the home, allowing you to create the perfect ambiance for any occasion. The kitchen is both stylish and functional, featuring an additional beverage refrigerator, making entertaining family and friends a breeze. The bathrooms offer a touch of luxury with heated floors and built-in Bluetooth speakers, creating a spa-like retreat within your own home. Situated on a large, level waterfront lot, the property is designed for both relaxation and recreation. Across the creek, protected conservation land provides a peaceful, natural backdrop and exceptional privacy rarely found on the water. Raised garden beds offer the opportunity to grow your own herbs and vegetables, while the detached garage, two storage sheds, and attic provide ample space for tools, equipment, seasonal items, and all your waterfront essentials. Spend your evenings gathered around the fire pit overlooking the water, launch a kayak from your backyard, or cruise to one of the many waterfront restaurants accessible from the Eastern Bay. Whether you're entertaining guests or enjoying a quiet sunset, this property embraces the laid-back charm of coastal living. Conveniently located just 10 minutes from the Bay Bridge, 20 minutes from Annapolis, and approximately 90 minutes from the beach, you'll enjoy easy access to everything while feeling worlds away. A rare opportunity to own a turnkey waterfront retreat in one of Kent Island's most desirable locations, where every detail has been thoughtfully curated for comfort, convenience, and enjoyment.

205 Riverside Dr, Chester

Listing courtesy of Engel & Volkers Annapolis. Contact: (443) 292-6767
$499,000
4 Beds ⋅ 3 Baths
NEW PRICE—An Unbelievable Value on Kent Island! Built in 2020, this gorgeous, like-new home offers approximately 1,974 square feet of beautifully maintained living space, a spacious yard backing to trees, and a desirable Kent Island location. An assumable VA loan at an attractive 2.75% interest rate may be available to qualified buyers, subject to lender and VA approval. Fresh interior paint and new carpeting throughout make this home truly move-in ready. The spacious living and dining areas provide plenty of room for everyday living and entertaining, while the inviting fireplace adds warmth and character. The kitchen features a breakfast bar, granite, pantry, abundant cabinetry, and generous storage. The spacious owner’s suite offers two walk-in closets and a private en-suite bath, creating a comfortable retreat. Step outside to enjoy the private backyard backing to trees, ideal for relaxing, entertaining, or enjoying peaceful evenings outdoors. Ccnvenient access to nearby boat ramps. Ideally located near shopping, dining, golf, pickleball, waterfront parks, walking trails, beaches, a dog beach, marinas, boat storage, Queenstown Premium Outlets, and popular local restaurants and entertainment. Experience the best of Kent Island living in this beautifully updated home. Some rooms have been virtually staged, including the owner’s suite, living room, and dining room.

124 Riverside Dr, Chester

Listing courtesy of Douglas Realty LLC. Contact: (866) 987-3937
$600,000
2 Beds ⋅ 3 Baths
Beautiful fourth-floor condo offering nearly 2,000 square feet of living space, featuring two bedrooms, a home office, two full baths, and a half bath. Enjoy morning sun from the oversized porch, a spacious living room, and an open-concept layout designed for comfort and entertainment. Highlights include luxury flooring, a fireplace, and a beautifully appointed kitchen with an oversized center island and quartz countertops stainless steel appliances and much more. This unit also includes a one-car garage and private storage space. The community offers unparalleled amenities and gorgeous water views, creating the perfect Chesapeake Bay lifestyle. Enjoy walking trails, outdoor tennis courts, indoor and outdoor pools, and a 23,000-square-foot clubhouse with outdoor spaces, a ballroom, test kitchen, outdoor bar, and community pier, views of the Chester River.

1000 Herons Nest Way Unit #43, Chester

Listing courtesy of Coldwell Banker Realty. Contact: kelly.thompson@cbmove.com
$399,500
3 Beds ⋅ 2 Baths
Welcome to 2645 Cox Neck Road, a move-in ready home in the desirable Harbor View Community of Chester. Offering 3 bedrooms, 1.5 baths, and situated on a spacious .34-acre lot, this well-maintained property combines comfort, convenience, and exceptional value at $399,500. Inside, you'll find a bright and inviting floor plan featuring a kitchen with a stylish tile backsplash, ample cabinetry, and luxury vinyl plank flooring. Thoughtfully maintained and updated over the years, this home offers peace of mind with a roof replaced within the last five years, replacement windows, siding, storm doors, and sliding glass door, as well as a recently replaced well pressure tank. Fresh interior paint and included appliances, including the washer and dryer, make moving in easy. Outdoor living is equally appealing with a charming front patio perfect for morning coffee and a large rear patio ideal for entertaining, grilling, or relaxing with family and friends. The beautifully maintained yard offers plenty of space for gardening, outdoor activities, or simply enjoying the outdoors. Two storage sheds provide ample room for tools, lawn equipment, and recreational gear. Located just minutes from Kent Island's popular restaurants, shopping, marinas, parks, and the Cross Island Trail, this home offers convenient access to everything the Eastern Shore lifestyle has to offer. Commuters will appreciate being less than 10 minutes from the Chesapeake Bay Bridge, while Harbor View residents enjoy a strong sense of community with neighborhood gatherings, holiday celebrations, yard sales, and other neighborhood events throughout the year. Whether you're searching for your first home, looking to downsize, or seeking a move-in ready property in a convenient Kent Island location, 2645 Cox Neck Road is an opportunity you won't want to miss.

2645 Cox Neck Rd, Chester

Listing courtesy of Compass. Contact: (410) 429-7425
$1,350,000
5 Beds ⋅ 2 Baths
The locals called it Keister's Folly. In the mid-1940s, Dr. Keister built a barn on Kent Island overlooking Cox Creek, hoping to raise Black Angus cattle on 25 acres. The acreage was too small for the endeavor — but the barn he built was extraordinary. In the early 1960s, the developer of the Harbor View community converted it into a residence. The current owners' family purchased it in 1965 and has invested over $400,000 in improvements across sixty years of devoted stewardship. This property has never been publicly offered for sale — until now. Situated on 1.65 acres with 205 feet of protected waterfront on Cox Creek, this is one of the largest privately held waterfront parcels remaining in Harbor View. The 75-foot private pier extends into navigable tidal water with approximately 3.5 feet at mean low tide and two boat slips. Shoreline reinforced with professional rip-rap. Maps show Flood Zone X — outside 100-year and 500-year floodplains - buyer and agent should verify. The home offers 3,456 sq ft of living space across two levels including 700+ sq ft of unfinished second and third-level expansion space. Five bedrooms, two full baths. The upper-level primary suite features hardwood floors, panoramic water views, attached full bath, walk-in closet, private coffee bar with refrigerator, and a deck overlooking the creek. Updated kitchen with granite countertops, upgraded cabinetry, and high-end appliances, improvements throughout honor the building's barn heritage. Solid block construction. 200-amp electrical. Well water, public sewer. New Roof will be installed prior to settlement. Ideal for those who are seeking genuine Chesapeake waterfront with privacy, deep water access, and a property unlike anything else on the market. Be sure to download the Home Profile in the documents section for more details on the home including the history of the home.

2513 Cecil Dr, Chester

Listing courtesy of Real Broker, LLC - Chester. Contact: 8554500442
$569,900
2 Beds ⋅ 3 Baths
Nestled in the charming community of Gibsons Grant, this exquisite townhouse offers a luxurious lifestyle with a perfect blend of comfort and elegance. Built in 2009, this Colonial-style residence spans 2,048 square feet and features two spacious bedrooms , with a another room that could be used for a 3rd bedroom and two and a half bathrooms, making it an ideal retreat for those seeking both style and functionality. Step inside to discover a thoughtfully designed interior that boasts hardwood and pine flooring, creating a warm and inviting atmosphere throughout. The combination kitchen and dining area is perfect for entertaining, featuring ample space for gatherings and culinary creations. Natural light floods the home, enhancing the inviting ambiance and highlighting the quality craftsmanship that defines this property. One year old HVAC and four year old hot water heater. The outdoor spaces are equally impressive, with a charming deck and porch that invite you to relax and enjoy the serene surroundings. Imagine sipping your morning coffee while taking in the gentle sounds of nature or hosting evening gatherings under the stars. The community pool and recreational facilities provide additional opportunities for leisure and relaxation, ensuring that every day feels like a vacation. Located just blocks from the Chester River, this property offers water-oriented living at its finest. Enjoy easy access to the river, perfect for kayaking or leisurely strolls along the waterfront. The community amenities, including a clubhouse, exercise room, and jogging paths, cater to an active lifestyle, while the meticulously maintained common grounds provide a picturesque backdrop for your daily activities. Parking is a breeze with a detached garage that offers additional storage space, ensuring that your home remains clutter-free. The association fee includes lawn care, snow removal, and trash services, allowing you to spend more time enjoying the luxurious lifestyle this community has to offer. Gibsons Grant is not just a place to live; it's a lifestyle choice that embraces the beauty of nature while providing modern conveniences. With its prime location, high-end features, and a strong sense of community, this townhouse is a rare gem that promises to be a cherished home for years to come. Experience the perfect blend of luxury and comfort in this stunning property, where every detail has been designed with your enjoyment in mind.

115 Gibson Cir, Chester

Listing courtesy of Long & Foster Real Estate, Inc.. Contact:

$700,000
3 Beds ⋅ 3 Baths
Newly adjusted price. Please visit me at the OPEN HOUSE this Sunday from 1-3pm. Rarely available, this luxurious Severn penthouse in Four Seasons at Kent Island offers the perfect blend of waterfront beauty, comfort, and resort-style living. Built in 2020 and meticulously maintained, the home features an open-concept design filled with natural light and stunning views of Macum Creek and the Chester River. The gourmet kitchen is the heart of the home, showcasing a large island, premium appliances, and picturesque water views. Three spacious bedrooms, two-and-a-half baths, and inviting living spaces provide comfort and flexibility for everyday living and entertaining. Enjoy spectacular sunrises, abundant wildlife, and peaceful water views from your private balcony. Just steps away, you'll find creekside trails, kayak launches, picnic areas, and direct access to the natural beauty that makes Kent Island so special. Located in desirable Phase One, this penthouse offers enhanced privacy, mature surroundings, and freedom from nearby construction. Additional features include an oversized attached garage with interior access and a secure storage room. Residents enjoy access to Four Seasons' exceptional amenities, including a 24,000-square-foot clubhouse, indoor and outdoor pools, fitness center, pickleball and tennis courts, fishing pier, kayak launches, dog parks, walking trails, tiki bar, and more.

2000 Herons Nest Way Unit #401, Chester

Listing courtesy of Real Broker, LLC. Contact: 8504500442
$599,900
3 Beds ⋅ 4 Baths
Experience the best of Kent Island waterfront living in this beautifully appointed home located in the sought-after Bayside community of Chester. Designed for both everyday comfort and effortless entertaining, this residence features an open-concept floor plan with abundant natural light, spacious living areas, and stylish finishes throughout. The gourmet kitchen serves as the heart of the home, offering generous counter space, quality cabinetry, and a seamless flow into the dining and living areas. The expansive primary suite provides a private retreat with a walk-in closet and luxurious ensuite bath. Additional bedrooms and flexible living spaces offer plenty of room for guests, a home office, or recreation. Enjoy outdoor living from the private deck, perfect for relaxing and taking in the peaceful surroundings. An attached garage and ample storage add convenience to everyday life. Residents of Bayside enjoy exceptional community amenities, including a clubhouse, fitness center, swimming pool, tennis courts, walking trails, and marina access. The boat slips at Castle Marina are rented. It can be on a short term up to a yearly basis. There are some slips over on the side where Queens landing condos are that can be for sale. Ideally located near waterfront dining, shopping, golf courses, and major commuter routes, this home offers the perfect blend of Eastern Shore charm and modern convenience. Don't miss this opportunity to enjoy a resort-style lifestyle in one of Chester's premier waterfront communities. Additional parking spaces are located across the street for your convenience.

1012 Auckland Way, Chester

Listing courtesy of Redfin Corp. Contact: 3016586186
$425,500
3 Beds ⋅ 4 Baths
Exceptional value for this renovated 3-bedroom, 3.5-bath end-unit townhome in the premier Bayside waterfront community. Comparable properties in this Chester River community have recently sold for much more, making this an outstanding opportunity for buyers seeking turnkey condition with over $50,000 in premium upgrades. Welcome to Bayside living at its finest. This meticulously maintained home sits in one of Chester's most desirable waterfront communities, offering nearby water access for morning walks along the Chester River, resort-style outdoor pool for summer enjoyment, and professionally maintained grounds. Minutes from Route 50/301 for easy commuting, yet peacefully situated in a serene riverside setting close to shopping, dining, and recreational activities. The owners have transformed this residence with quality upgrades throughout. Real hardwood flooring spans the entire main and upper levels with no carpet anywhere in the home. The entry welcomes you with elegant slate tile while abundant natural light floods every room, creating bright and inviting spaces perfect for both daily living and entertaining. The completely renovated chef-inspired kitchen features top-tier stainless steel appliances including Thermador induction cooktop, GE Monogram wall oven, and Bosch dishwasher. Granite countertops, updated cabinetry, and recessed lighting complete this stunning space. The open-concept design connects seamlessly to the spacious living area, making entertaining effortless and family gatherings comfortable. Your main level living room centers around a cozy gas fireplace surrounded by built-in bookshelves, creating the perfect gathering spot year-round. Step outside to your private deck with retractable awning where you can enjoy winter water views of the Chester River. This outdoor space provides an ideal extension of your living area for morning coffee, evening relaxation, or weekend entertaining. The upper level primary suite serves as your personal retreat with a spacious walk-in closet and luxurious ensuite bathroom featuring a jetted soaking tub and separate shower. Your own private outdoor deck off the primary suite provides a serene escape for morning coffee or quiet evening moments. The second bedroom on this level includes its own attached full bathroom, offering privacy and comfort for family or guests. The versatile top-floor loft space features abundant natural light, two generous walk-in closets, and another full bathroom. Use this flexible area as a guest suite, home office, creative studio, or third bedroom based on your lifestyle needs. The possibilities are endless with this unique third-level retreat. Modern systems ensure comfort and efficiency throughout. The recently updated HVAC system provides year-round climate control while reducing energy costs. High-efficiency washer and dryer convey with the home for added value. The attached one-car garage offers protected parking and additional storage space, while the end-unit positioning provides enhanced privacy with no neighbors on one side. This home is completely turnkey and move-in ready. The combination of hardwood floors, premium Thermador and GE Monogram appliances, modern HVAC system, and updated finishes throughout means you can move in immediately and start enjoying your new lifestyle without any projects or renovations required. Low-maintenance living at its best. Your monthly Condo fee includes lawn maintenance, snow removal, community pool access, and recreation facilities, allowing you to spend your time enjoying the waterfront lifestyle rather than maintaining property. This is the perfect balance of Chester River community living with modern convenience and resort-style amenities. The value proposition is compelling. This home's aggressive positioning combined with over $50,000 in premium upgrades creates an exceptional opportunity for discerning buyers. The motivated seller situation, extensive recent improvements, prime end-unit location

807 Auckland Way, Chester

Listing courtesy of Real Broker, LLC - Chester. Contact: 8554500442
$435,000
3 Beds ⋅ 3 Baths
Welcome to Bayside, where coastal living and resort-style amenities come together in one of the area’s most desirable waterfront communities. This 3-bedroom, 2.5-bath condo offers a relaxing marina-side setting with both upper and lower decks overlooking the marina, creating the perfect backdrop for morning coffee, evening sunsets, and everything in between. Inside, you’ll find a spacious layout designed for comfortable living, complete with a cozy gas fireplace, generous living spaces, and the convenience of a 1-car garage. Recent improvements include a new roof in 2023 and the front foot fee paid off in 2024, as well as a one-year home warranty for the buyer — adding additional value and peace of mind for the next owner. Life in Bayside is all about lifestyle. Residents enjoy access to resort-style amenities including a clubhouse, outdoor pool, fitness center, tennis courts, volleyball courts, and scenic walking and jogging trails — all just steps from the marina and moments from the Chesapeake Bay. Perfectly located near waterfront restaurants, local shops, and major commuter routes to Annapolis, Baltimore, and Washington D.C., this home offers the ideal blend of relaxation and accessibility. Whether you’re searching for a full-time residence or the perfect weekend waterfront escape, this Bayside condo captures the very best of Eastern Shore living.

106 Bodys Neck Rd, Chester

Listing courtesy of Realty Navigator. Contact: 4106433404
$840,000
4 Beds ⋅ 4 Baths
Situated on one of the largest lots in sought-after Gibson’s Grant, this 4-bedroom, 3.5-bath home offers space, flexibility, and room to grow. High ceilings and an open layout create an airy feel, with an oversized kitchen flowing seamlessly into the family room and a separate main-level office for work or quiet retreat. The main level also features a formal dining room and living room. Upstairs, the spacious primary suite features a sitting area, two walk-in closets, and en-suite bath, alongside three additional bedrooms and two full bathrooms. The unfinished walkout basement includes a rough-in for a future bath. Outside, enjoy a fenced backyard complete with a patio and built-in fire pit—perfect for gathering year-round. Community amenities include swimming pool, clubhouse, fitness center, walking trails, community pier, picnic area, and kayak launch. Centrally located on Kent Island. Only 5 minutes to the Bay Bridge.

232 Evelyne St, Chester

Listing courtesy of TTR Sotheby's International Realty. Contact: 4106733344
$700,000
2 Beds ⋅ 3 Baths
Priced to sell at just $700,000, this is an exceptional opportunity. With a $160,000 lot premium and over $60,000 in builder upgrades, this home is offered below its replacement value. Experience everything Four Seasons has to offer without the wait. This meticulously maintained home shows like new and is located just steps from the community amenities and vibrant social spaces that make Four Seasons so desirable. 132 Wheelhouse Way offers one of the most desirable locations in the community, with exceptional water views, ground-level access, and an easy walk to the resort-style amenities. Inside, you'll find a gourmet kitchen with quartz countertops, GE Café double wall ovens, upgraded stainless steel appliances, luxury vinyl plank flooring, and an open-concept living space with an electric fireplace and beautiful water views. The primary suite features patio access, a walk-in closet, and a luxurious bath, while the second bedroom suite and private office provide comfort and flexibility. Residents enjoy the Chester House Clubhouse, indoor and outdoor pools, a fitness center, pickleball and tennis courts, walking trails, a kayak launch, fishing pier, dog park, tiki bar, and more. Perfectly located on Kent Island, this home offers an exceptional blend of luxury, convenience, and the Chesapeake Bay lifestyle.

132 Wheelhouse Way Unit #11, Chester

Listing courtesy of Real Broker, LLC. Contact: 8504500442
$364,900
3 Beds ⋅ 3 Baths
Nestled in the heart of Kent Island, this charming 3 Bedroom, 2 Full Bathroom townhome with Bonus Room, offers the perfect blend of comfort, convenience, and peaceful surroundings. Located in the desirable Bridgepointe community, this home features major updates including a newer roof, HVAC system, and water heater providing peace of mind for years to come. Enjoy a private backyard setting that backs to mature trees, creating a serene outdoor retreat, while being just steps from the community lake, walking paths, and boat parking lot! Inside, the functional layout offers spacious living areas, comfortable bedrooms, and plenty of natural light throughout. Whether you're looking for a primary residence, weekend getaway, or low-maintenance lifestyle near the Chesapeake Bay, this Kent Island gem is ideally situated close to shopping, dining, marinas, and commuter routes. Schedule your tour today!

5011 Bridgepointe Dr, Chester

Listing courtesy of Keller Williams Realty Centre. Contact: 4103120000
$357,900
3 Beds ⋅ 3 Baths
Low maintenance island living at its best! 6005 Bridgepointe Dr is freshly painted, deep cleaned, and ready for its new owners! All appliances new within the last two years, power washed & fresh paint on the deck with beautiful views of the pond. Easy access to RT50 - perfect for the commuter. Quiet neighborhood.

6005 Bridgepointe Dr, Chester

Listing courtesy of Rosendale Realty. Contact: 4107580333
$216,000
3 Beds ⋅ 2 Baths
You wouldn't think it but the property offers 3 bedroom and 2 full baths. Patio right off kitchen for the summer cookouts! Easy yard maintenance here, not much grass to manage, leaves plenty of time for those cookouts. Close to Route 8 for easy east/west access. Property sold as is, no repairs will be made by seller. HUD CASE 244-032645, reach out for more information on this unique buying opportunity. Property is owned by the US Dept. of HUD. All HUD Homes are sold “AS-IS”. This property is HUD Case # 244-032645. Information and Disclosures available at hudhomestore website. property Insurability code is: IE. Bids may only be submitted by HUD Registered Agents/Agencies. Buyers are responsible for Dewints/Rewints coordination/expenses. LBP (Lead-Based Paint) may be present. Seller makes no representations or warranties as to property condition.

108 Price Rd, Chester

Listing courtesy of Thurston Wyatt Real Estate, LLC. Contact: 4103206785
$620,000
3 Beds ⋅ 3 Baths
Welcome to 265 Evelyne Street in the sought-after waterfront community of Gibsons Grant! Offering nearly 2,200 square feet of living space, this beautifully maintained home combines coastal charm with modern comfort. Inside, you’ll find engineered hardwood floors, a spacious open-concept layout, and a beautifully appointed kitchen featuring a large island, gas stove, double oven, and plenty of space for gathering and entertaining. The flexible floor plan includes a spacious family room above the two-car garage — perfect for a media room, playroom, home office, or guest retreat. The primary suite offers a relaxing escape with a double vanity, soaking tub, and walk-in shower. Additional highlights include a Rinnai tankless hot water heater, welcoming front porch, and thoughtful upgrades throughout. Enjoy all that Gibsons Grant has to offer, including a community pool, clubhouse, fitness center, kayak launch, walking trails, playgrounds, waterfront access, and scenic open spaces — all conveniently located just minutes from the Bay Bridge, shopping, dining, and everything Kent Island has to offer. Coastal living at its best!

265 Evelyne St, Chester

Listing courtesy of Samson Properties. Contact: 7033788810
$349,500
2 Beds ⋅ 3 Baths
Seller is offering closing cost assistance for qualified buyers! This charming townhouse in Queens Landing offers a perfect blend of comfort and community amenities. Step inside to discover a traditional floor plan featuring a cozy living room off the eat-in kitchen, with a separate family room ideal for gatherings. The home boasts two spacious bedrooms and 2.5 baths, including a primary bath for added convenience. Updates include new flooring throughout; LED lighting, granite counters, newer windows and HVAC system. Enjoy modern amenities with a suite of appliances, including a built-in microwave, dishwasher, electric range, washer and dryer. Outside, the community shines with well-maintained sidewalks, streetlights, and a variety of recreational facilities. Take advantage of the clubhouse, outdoor pool, tennis courts, and scenic waterfront jogging paths. The nearby Chester River provides a serene backdrop for leisurely strolls and outdoor activities, with access to the Cross Island Trail connecting waterfront features at Terrapin Park and The Narrows. Located within a vibrant neighborhood, residents benefit from access to parks and essential public services. This home is not just a place to live; it's a gateway to a fulfilling lifestyle in a welcoming community. Some photos displayed used AI and may not be 100% accurate. Please schedule an in-person tour to view this beautiful property.

45 Queen Neva Ct, Chester

Listing courtesy of Coldwell Banker Realty. Contact: 4102638686
$5,900,000
7 Beds ⋅ 9 Baths
Designed to rival a private resort, this waterfront estate was built for celebrating with family and friends. Sweeping Chesapeake views set the stage for every gathering. The waterfront pool features a cascading rock waterfall, a tucked in bench, and a generous sun shelf, all overlooked by a pool house with a covered summer kitchen, bar, seating area, and full bath with AC. A curated firepit lounge, expansive patios and balconies, and a screened waterside porch bring indoor and outdoor living together for every occasion. At the shoreline, life on the Bay begins, with an expansive private beach perfect for wading, sandcastles, and quiet evenings by the water. The newly expanded L shaped pier stretches 260 feet and is engineered for serious boating, with dockage for a large yacht, 24,000 lb. and 10,000 lb. lifts, electric, R/O water, dual pedestals, and decorative lighting. Protected waters offer calm conditions for docking, fishing, crabbing, and watersports, with direct Bay access and easy cruising to Annapolis, St. Michaels, and beyond. A circular driveway centered by a gorgeous fountain leads to the entry, where a stunning two story foyer and grand staircase greet you, framed by spectacular water views. The great room features a soaring wall of glass and a fireplace, opening to a chef's kitchen appointed with Wolf and Sub Zero appliances, custom cabinetry, a conversation bar, pantry, and breakfast nook. The dining room seats twelve or more, ready for every holiday feast. The primary suite is a private waterfront retreat, with a sitting area beneath a domed ceiling, a fireplace, custom built ins, and a spa bath with heated floors, a jetted soaking tub, and a multi head shower. The waterfront game room offers a fireplace, wet bar, and large TV, while the private theater seats eight in front of a 100 inch screen, making this home the destination for family and friends year round. Upstairs, five architecturally unique bedrooms, three ensuite, include private waterfront balconies and a large activity room opening to a deck overlooking the pool, dock, creek, and bay. A fully equipped in law suite offers its own kitchen, living area, bedroom, fireplace, and attached two car garage, while a separate heated and cooled four car garage with porcelain tile and custom cabinetry serves as studio, workshop, or gym. Six fireplaces, Anderson and Palladian windows, tankless water heaters, a whole house water softener and reverse osmosis system, a 60KW whole house generator, and fiberoptic 2.5GB internet with seventeen access points bring comfort and connectivity throughout. Fully app based control manages lighting, HVAC, security, pool, spa, generator, music, locks, and network, inside and out. Tucked along a quiet private road with easy access to the Bay Bridge, Annapolis, and Washington D.C., this is waterfront vacation living designed to be experienced every day. Serenity Lane describes how you feel, not just where you are. Welcome home.

330 Serenity Ln, Chester

Listing courtesy of TTR Sotheby's International Realty. Contact: (410) 280-5600
$359,900
3 Beds ⋅ 3 Baths
Completely remodeled in 2026 with a new kitchen to include new appliances, quartz counters, and backsplash, 3 new bathrooms, all new flooring throughout, new washer and dryer and freshly painted. Nestled in the serene enclave of Queens Landing, this exquisite remodeled in 2026 Colonial townhouse offers a harmonious blend of luxury and comfort. Spanning 1,440 square feet, the open floor plan invites you to experience a seamless flow between the combination dining and living areas, perfect for both intimate gatherings and entertaining. The family room, conveniently located off the kitchen, creates a warm atmosphere where cherished memories are made. Indulge in the elegance of three spacious bedrooms all on the same level and two and a half beautifully recently remodeled bathrooms, designed for relaxation and rejuvenation. The inviting ambiance is enhanced by the cozy fireplace, providing a perfect backdrop for cozy evenings at home. Step outside to discover the community's stunning outdoor pool, where you can unwind under the sun or enjoy leisurely afternoons by the water. With direct access to the Chester River, water enthusiasts will appreciate the navigable waters, ideal for kayaking or simply soaking in the tranquil views. Queens Landing boasts an array of amenities, including a clubhouse, exercise room, and scenic bike trails, fostering an active and vibrant lifestyle. The meticulously maintained common grounds offer a picturesque setting for leisurely strolls or social gatherings. This property is not just a home; it's a lifestyle choice that embodies luxury, comfort, and community. Experience the best of waterfront living in this exceptional residence, where every detail has been thoughtfully curated for your enjoyment. Schedule your tour today!

54F Queen Caroline Ct, Chester

Listing courtesy of Long & Foster Real Estate, Inc.. Contact:

$319,900
3 Beds ⋅ 3 Baths
Priced to Sell! Discover refined waterfront community living in this beautifully updated and rarely available 3-bedroom, 2.5-bath condo in the highly desirable Queen’s Landing community. Thoughtfully designed with both comfort and style in mind, this spacious home offers fresh interior paint, an inviting open layout, and a beautifully updated kitchen featuring elegant quartz countertops—perfect for everyday living, relaxing weekends, and entertaining family and friends. Natural light fills the living spaces, while the seamless flow between the kitchen, dining, and living areas creates a warm and welcoming atmosphere throughout the home. Step outside to enjoy your private screened porch—ideal for morning coffee or evening unwinding—or host summer gatherings on the private patio designed for grilling and outdoor entertaining. Rare opportunities like this don’t come along often in Queen’s Landing, especially with the combination of three bedrooms, modern updates, and exceptional outdoor living spaces. Enjoy a true resort-style lifestyle with community amenities that include a swimming pool, fitness center, pickleball and tennis courts, and a private marina. Whether you’re looking for a full-time residence, weekend retreat, or low-maintenance coastal lifestyle, this home offers the perfect balance of relaxation and convenience. Ideally located in the heart of Chester, you are just minutes from waterfront dining, shopping, entertainment, and major commuter routes—making it easy to enjoy everything the Eastern Shore has to offer while staying connected to Annapolis, Baltimore, and Washington, D.C.

54 Queen Caroline Ct, Chester

Listing courtesy of Island Realty, LLC. Contact:

$999,000
5 Beds ⋅ 5 Baths
Welcome to luxury coastal living in the highly desirable Four Seasons at Kent Island 55+ community in Chester. Built in 2025, this practically new home offers the perfect blend of elegance, comfort, and convenience — without the wait for new construction. Ideally situated on coveted Kingfisher Lane, this exceptional Tuscaloosa model offers over 3,200 square feet of beautifully designed living space with 5 bedrooms and 4.5 baths. The upgraded stone-and-shake exterior creates stunning curb appeal, while the covered front porch offers peaceful peek-a-boo water views — the perfect place to enjoy your morning coffee at sunrise. Inside, the open-concept main level showcases a thoughtfully upgraded interior with classic cabinetry, glass display cabinets, and professional-grade GE appliances in the kitchen. The spacious living area is anchored by a dramatic stone gas fireplace, while custom wall detailing and molding upgrades in the foyer and primary suite add warmth and sophistication throughout the home. Norman shutters on every window, upgraded carpet with premium padding, and carefully selected finishes elevate every room. The main-level primary suite offers a private retreat with elegant trim details and a spa-inspired en suite bath featuring a luxurious soaking tub designed for relaxation. Additional upgrades include a screened porch for outdoor enjoyment, epoxy garage flooring, painted garage walls, and a dedicated EV charging station for modern convenience. Located just a short distance from the community dog park, playground, pickleball and tennis courts, and the state-of-the-art clubhouse, this home offers not only exceptional design but also an unmatched lifestyle. Residents of Four Seasons at Kent Island enjoy resort-style amenities including indoor and outdoor pools, a fitness center, walking trails, social spaces, and activities designed to support an active and vibrant coastal lifestyle. All of this is ideally located just minutes from the Chesapeake Bay Bridge, offering convenient access to Washington and Baltimore, while also being close to shopping at the Queenstown Premium Outlets and an array of local waterfront dining and everyday conveniences.

233 Kingfisher Ln, Chester

Listing courtesy of Samson Properties. Contact: 7033788810
$295,000
2 Beds ⋅ 2 Baths
Experience the ease of resort-style, maintenance-free living in this beautifully updated upper-level condominium featuring open views, abundant natural light, and the privacy of having no neighbors above. Hardwood floors, soaring vaulted ceilings, and a cozy gas fireplace create a warm and inviting atmosphere throughout the main living area. The spacious primary suite offers a peaceful retreat with a generous bedroom, ample closet space, and a private ensuite bath. A second bedroom provides exceptional flexibility as a guest room, home office, or space for family and grandchildren. The updated kitchen is equipped with newer appliances, including a refrigerator, microwave, washer, dryer, garbage disposal and hot water heater. The adjoining dining area overlooks sliding glass doors leading to a private balcony where you can relax and enjoy the expansive open views. Beyond the home, enjoy an exceptional lifestyle with access to community amenities including a clubhouse, swimming pool, pickleball courts, and fitness center. A marina is within walking distance, making it easy to enjoy boating and waterfront activities. The cross trail is just steps from your condo. The condominium association handles exterior maintenance and community upkeep, allowing you more time to enjoy the things you love. Ideally situated near fine dining, shopping, and cultural attractions, this location also offers outstanding accessibility—within easy reach of three international airports—making travel convenient whether for business, family visits, or leisure. This is the perfect opportunity to enjoy a low-maintenance lifestyle without sacrificing comfort, convenience, or amenities. "Elevated living, exceptional amenities, and a carefree lifestyle—all in one remarkable home."

114 Merganser Ct, Chester

Listing courtesy of Benson & Mangold, LLC. Contact: (443) 988-0483
$559,000
3 Beds ⋅ 3 Baths
Welcome to this beautifully maintained 3-bedroom, 2.5-bathroom home in the Waterman’s Cove community in Chester. Nestled on a quiet street along scenic Cox Creek, this charming property offers the perfect blend of comfort, style, and convenience. An inviting front porch welcomes you home, while water views greet you upon arrival and can also be enjoyed from the spacious rear composite deck, built by Lundberg Builders, perfect for relaxing or entertaining. The home sits adjacent to community open space, offering added privacy with no direct neighbor next door. Inside, you’ll find hardwood flooring and an open-concept layout designed for modern living. The living room flows seamlessly into the dining area and kitchen, which features granite countertops, stainless steel appliances, and a beautiful tile backsplash. Sliding doors off the dining area lead to the composite deck and a lush, partially fenced yard, creating an ideal space for indoor-outdoor living. The kitchen also provides convenient interior access to the attached one-car garage. Upstairs, the primary suite offers a well-appointed bath, two additional bedrooms, a second full bath, and a laundry room for added convenience. Located just one mile from Route 50 on Cox Neck Road, this home offers quick access to shopping, dining, commuter routes to Washington DC and Baltimore, and the Chesapeake Bay Bridge. The intimate Waterman’s Cove community consists of just nine homes, with HOA services that include lawn care and trash removal - making for easy, low-maintenance living. Enjoy the peaceful lifestyle of Maryland’s Eastern Shore, with water views and privacy in a highly convenient location.

126 Watermans Cove Ln, Chester

Listing courtesy of Coldwell Banker Realty. Contact: 4102638686
$1,195,000
4 Beds ⋅ 5 Baths
Located in the prestigious Southwind community, a penisula between Crab Alley Bay & Cox Creek, this elegant contemporary ranch-style home offers an unparalleled lifestyle of luxury and comfort. Spanning over 4,400 sq. ft. of finished space, the interior boasts elegant marble flooring, complemented by crown moldings and built-ins that enhance its sophisticated charm. The gourmet kitchen, featuring upgraded countertops and a spacious island, flows seamlessly into the family room, perfect for entertaining. Relax in the primary suite with a lavish bath or unwind in the inviting family room by the fireplace with views out to Crab Alley. Three additional bedrooms (or two bedrooms and an office) and two baths round out the main level that offers sweeping scenic views from every vantage point. Step outside to discover a private oasis on 1.25 acres, complete with extensive hardscaping, a heated in-ground pool, and a soothing hot tub. Enjoy picturesque water views out the front and back, with access for kayaking and boating. The community amenities, including a beach, clubhouse, and tennis courts, elevate your living experience. This home is not just a residence; it's a lifestyle waiting to be embraced and enjoyed. Start living your best 'Shore Life' at 2855 Cox Neck Rd.

2855 Cox Neck Rd, Chester

Listing courtesy of Wilson Realty & Staging LLC. Contact: 4103042250
$399,000
3 Beds ⋅ 4 Baths
REDUCED! Just like NEW! Welcome Home to this beautifully upgraded 4BR END UNIT Townhome with 2 full and 2 half baths, thoughtfully renovated from top to bottom! Step inside to find the main level that boasts NEW carpet and new LVP flooring, a NEW half bath, NEW paint, a spacious laundry room and a large bedroom that could be used as another family room, toy/game room, den space, home office and more! Get ready to be wowed by the rich walnut NEWLY stained hardwood flooring throughout the 2nd level where the living room, gas fireplace, NEW half bath and kitchen are located. The BRAND-NEW Kitchen finishes are sure to please with NEW white quartz counter tops, NEW SS Appliances, fresh neutral paint and white cabinetry! Upstairs hosts the huge Primary En-Suite, 2 more bedrooms all with NEW Carpet and another full bathroom with NEWLY Tiled shower, NEW toilet and NEW quartz sink! With three generous levels, a deck overlooking the pond, a cozy patio and a charming front porch, there’s space for everyone to relax and have their own space! Pull right into your own garage and your own driveway which makes life easy not to have to look for parking! The community offers fantastic amenities to enjoy like the inground and life-guarded pool, volleyball & tennis courts, fitness gym and direct access to the Cross Island Trail! Very close to the Castle Harbor Marina, many Beaches, Parks & Playgrounds and just a short stroll to local restaurants along the waters edge of the CHESTER RIVER! Condo living made easy with the Bayside fee covering major exterior maintenance including the roof, deck rails, siding, exterior structural upkeep, landscaping, snow removal, road maintenance, trash, master insurance policy, professional property management, long term reserve funding and the list goes on! Truly turn‑key living in an unbeatable location on the desired Eastern Shore of Maryland! Come see what Kent Island living is all about! SUMMER is here!

208 Blenny Ln, Chester

Listing courtesy of RE/MAX Executive. Contact: 4432741900
$680,000
3 Beds ⋅ 3 Baths
A rare blend of coastal proximity and refined living unfolds within this beautifully appointed corner residence in the sought-after 55+ waterfront community of Four Seasons at Kent Island. Built in 2024 and impeccably maintained , this like-new residence offers the comfort of immediate enjoinment without the wait for new construction. Positioned near a tranquil creek leading to the Chesapeake Bay, the home offers a lifestyle deeply connected to the water without the demands of direct waterfront ownership. Sunlight fills the open-concept layout through the residence’s desirable corner positioning, highlighting soaring ceilings, luxury vinyl plank flooring, and thoughtfully selected finishes throughout. The gourmet kitchen flows seamlessly into the dining and living areas, creating an inviting space for both quiet evenings and entertaining. Just beyond, a private balcony offers peaceful green surroundings with subtle water views, extending the home’s living space into a serene outdoor setting. The spacious primary suite serves as a private retreat with walk-in closets and a beautifully finished en-suite bath, while two additional bedrooms provide flexibility for guests, hobbies, or a home office. Residents of Four Seasons at Kent Island enjoy access to resort-style amenities including indoor and outdoor pools, fitness center, clubhouse spaces, pickleball and tennis courts, scenic walking trails, kayak launch, and fishing pier. Conveniently located near Kent Narrows, Annapolis, and Route 50, this exceptional residence offers a refined Eastern Shore lifestyle with easy access to dining, recreation, and waterfront experiences.

111 Marshgrass Way Unit #21, Chester

Listing courtesy of Samson Properties. Contact: 2406308689
$559,900
2 Beds ⋅ 3 Baths
Experience "Paradise" in Queen’s Landing. This rare, end-unit waterfront gem offers an unparalleled living experience overlooking the serene Lake Amleto. Boasting a 2019 full-gut renovation by a custom contractor, this 1,425 sq. ft. residence (including a 145 sq. ft. sunroom) blends sophisticated design with resort-style tranquility. The interior showcases master-level craftsmanship: solid hickory wood floors, custom solid wood doors, custom maple cabinetry with ingenious storage solutions (toe-kick and spice & utensil drawers), and Calacatta Gold marble adorning both the kitchen and the gas fireplace surround. The open floor plan is optimized with structural improvements, including a pantry with a pocket door, a custom staircase with integrated storage, and a hidden Murphy door. Extensive recessed lighting on main floor with 3 dimmable picture wall accent lighting. Luxury finishes abound, from Emtek brass hardware and crown molding in every room to Monogram premium appliances and custom window treatments with a hidden railing system. Both upper-level bedrooms feature ensuites and are private retreats; one features a Travertine shower and floor with antique bronze hardware, while the other offers elegant Italian tile. Relax year-round in the sunroom, constructed with heavy-duty UV-protected glass, to watch herons and waterfowl against a backdrop of lake fountains. A remote-controlled full patio width awning installed to control the amount of sunlight coming into the home. Modern peace of mind is provided by an under- warranty Carrier HVAC system (with humidifier/air cleaner), Homeguard water softener, and updated roof, windows, and stucco. The Queen's Landing lifestyle includes a renovated clubhouse, heated outdoor pool, fitness center, pickleball and tennis, racquetball, community marina, kayak launch and racks. Unique Opportunity: The owner is also offering a 70-foot deep-water boat slip for separate purchase—a rare find for the avid mariner. Features List: • Renovation: Total gut-renovation (2019) including structural optimizations. • Kitchen: Custom Maple cabinetry, Calacatta Gold Marble counter tops and backsplash, Monogram/Blomberg appliances. • Mechanicals: Carrier HVAC w/ humidifier, Homeguard softener, LG HE Washer/Dryer. • Extra insulation in the attic with insulated access cover. Sound proofing insulation between the first and second floor was added during the remodel. • WellSys water dispenser: tied to home plumbing and includes cold and hot water. This is an optional rental unit and is contained within the kitchen cabinet. • Exterior: New Roof (2021), New Stucco (2017), New Windows/Front Door (2017). • Parking/Storage: Storage room off sunroom; ample community parking. • Boating: 70’ deep-water slip available.

29 Queen Mary Ct, Chester

Listing courtesy of Jorge A. Zea. Contact: 8555500528
$485,000
2 Beds ⋅ 3 Baths
BACK on the MARKET. GREAT OPPORTUNITY at THIS PRICE. This Chester model has scenic, seasonal views of Macum Creek, beautiful sunrises, and an incredible display of wildlife in all seasons. Easy walk to Kayak launch and creek. With nearly 2000 square feet of open living space this home has a great layout for entertaining family and friends. The spacious great room, adjacent to the dining area and kitchen, provide an open area for gatherings. The gourmet kitchen is equipped with upgrades from the stunning kitchen island with quartz counter tops, beautiful upgraded cabinetry to the GE Profile appliances. This kitchen is designed for everyday living as well as hosting the occasional dinner party. The primary bedroom, is a separate self-contained suite complete with two closets and a luxury owners' bath that includes double sinks, and quartz countertops. The bright and airy 2nd bedroom is also a separate suite with a full bath and an oversized walk-in closet. In addition to the two bedrooms, there is a home office with stylish French Doors and a powder room for guests. The separate laundry room is equipped with a GE washer and dryer. This home also has a garage with adjoining driveway/parking space and large personal storage room which is a few short steps from the elevator. This home is just a short walk to resident kayak racks with launch access to the Chester River. KEEP IN MIND THIS CHESTER MODEL, WITH PLENTY OF FEATURES AND UPGRADES INCLUDED, IS MOVE-IN READY AND PRICED TO SELL***** Award-winning 24,000 Square Foot Clubhouse with Stunning Chester River Views! Fantastic amenities include 4.3 miles of walking trails throughout the community, outdoor infinity pool, indoor pool with on-duty lifeguard, fitness center, library, game room, gas and wood burning fire pits, Tiki bar equipped with refrigerators, sinks and television monitors, pier with transient boat slips, walking paths that link to the Cross Island Trail, lighted pickle ball courts, tennis courts, bocce, dog park, and an outdoor amphitheater for live music and movie nights. The community lifestyle director will keep you busy with daily activities such as yoga, a variety of exercise classes and an assortment of clubs including biking, billiards, book club, baking, mahjong, environmental club, trivia night and more. In addition to the weekly and monthly activities, residents can enjoy crab feasts, oyster roasts, and holiday gatherings throughout the year. This development is an unrivaled, amenity-filled, resort-style experience with convenient access to Annapolis, DC, Baltimore, and BWI. Kent Island offers multiple dining and shopping options, a nearby outlet mall, and a 6.5 mile cross-island trail surrounded by views of the Chester River.

1000 Herons Nest Way Unit #22, Chester

Listing courtesy of RE/MAX Executive. Contact: 4432741900
$765,000
2 Beds ⋅ 3 Baths
Penthouse Unit! Seller offering closing cost assistance to qualified buyers! Rare top floor unit with year-round water views perfectly positioned to capture stunning sunrises every morning. This home has been owned and meticulously maintained by the original owner who spared no expense and opted for every builder upgrade that was offered, over $60,000.00 in options. The open concept design seamlessly connects the living room, dining area, and kitchen areas, all enhanced by expansive windows letting in an abundant amount of natural light. Experience resort style living in the highly sought after Four Seasons at Kent Island, a premier 55+ waterfront community. Residents enjoy access to world class amenities, including indoor and outdoor pools, walking trails, a Chester River pier. Ideally located just minutes from waterfront dining, shopping, and the Chesapeake Bay Bridge, this home offers the perfect blend of relaxation, convenience and low maintenance living at its finest.

111 Marshgrass Way Unit #43, Chester

Listing courtesy of Coldwell Banker Realty. Contact: 4102638686
$1,049,500
5 Beds ⋅ 5 Baths
Price Reduced $50K – Check out the Virtual Tour! Exceptional Value in Four Seasons at Kent Island Why wait to build? This less-than-one-year-old Tuscaloosa model on sought-after Kingfisher Lane delivers the upgrades, location, and efficiency buyers are chasing—without the timeline or added expense. Positioned just across from the Chester River, enjoy peekaboo water views from the covered front porch and even a sightline to the clubhouse. Inside, the home is bright, open, and thoughtfully designed with 5 bedrooms and 4.5 baths, offering flexibility for guests, work-from-home space, or multigenerational living. It shows like new—but lives better—because everything has already been elevated beyond builder grade. Over $70,000 in post-builder upgrades, including: • Owned solar system (10kW+) providing substantial energy savings • Custom closet systems throughout the home • Custom window treatments already installed • Premium Café Series appliances • Tankless water heater • Upgraded lighting and fixtures • Additional high-end finishes and improvements throughout The spacious floor plan offers room for everyone, while the oversized garage provides ample storage for vehicles, golf carts, and all the gear that comes with Eastern Shore living. Life in Four Seasons at Kent Island is about more than the home itself. Residents enjoy resort-style amenities including a stunning clubhouse, indoor and outdoor pools, fitness center, pickleball courts, walking trails, kayak launch, fishing pier, and an active social calendar designed for a vibrant lifestyle. With immediate availability, extensive upgrades already completed, and one of the community's most desirable locations, this home represents an opportunity that's becoming increasingly difficult to find. Add in the recent $50,000 price reduction, and this is one of the best values currently available in Four Seasons at Kent Island. Don't miss your chance to enjoy nearly new construction, energy-efficient living, and the Chesapeake Bay lifestyle you've been waiting for.

215 Kingfisher Ln, Chester

Listing courtesy of RE/MAX Executive. Contact: 4432741900
$365,000
2 Beds ⋅ 2 Baths
**OPEN HOUSE this SATURDAY July 25TH: 9AM-11AM** Looking for more space than you might expect on Kent Island? This spacious end-unit home offers over 1,800 square feet with a flexible layout designed to give you plenty of room to make it your own. At the heart of the home, the oversized kitchen provides an abundance of cabinetry and countertop space, making it ideal for everyday living, entertaining, or anyone who simply appreciates having room to spread out. The open layout flows into a generously sized living area, while a conditioned sunroom surrounded by windows adds even more usable living space and leads to a large rear deck overlooking peaceful pond and fountain views. Two spacious bedrooms and two full bathrooms provide comfortable accommodations, while the converted garage creates valuable bonus space ready to adapt to your needs as a home office, den, hobby room, guest space or additional living area, with the option to return it to a traditional garage if desired. The end-unit location brings additional natural light and a more open feel, while multiple living spaces throughout the home offer flexibility that's increasingly hard to find. Conveniently located in Chester and close to everything Kent Island has to offer, this home combines generous square footage, a versatile floor plan and a peaceful outdoor setting with plenty of opportunity to make the space your own. Additional peace of mind with one year Home Warranty offer!!

2008 Bridgepointe Dr, Chester

Listing courtesy of RE/MAX Executive. Contact: 4432741900
$159,900
2 Great Building Lots - Sewer Approved on Kent Island , Sewer fee is paid for - Harley Lane Lot #1 Parcel 63 comes with working Well $159,900. An Adjacent Lot #2 Parcel 64 is available. Sewer is also approved with fee paid. $149,900. These approved Lots are registered with Queen Annes County. *****The Harley Lane 2 lot sub division was created by adding 2 lots on land owned on Good hand creek road. Entrance to lots is from Harley lane left turn from Dominion road

Lot #1 Harley Ln, Chester

Listing courtesy of NetRealtyNow.com, LLC. Contact: (703) 581-8605
$515,000
2 Beds ⋅ 3 Baths
WATERFRONT Condo! Open House dates scheduled. Beautifully renovated 2BR/2.5BA waterfront condominium located in the sought-after Queen’s Landing resort-style community on the scenic Chester River, just off the Chesapeake Bay. This move-in-ready home showcases a stunning top-to-bottom remodel, including new luxury vinyl plank flooring, new carpet, fresh paint throughout (ceilings, walls, trim, and doors), new white cabinetry, beautiful quartz countertops with beveled white backsplash, updated bathroom vanities, flooring and modern lighting fixtures. The light-filled open floor plan is designed to highlight the panoramic Chester River views. The spacious family room off the kitchen features an oversized sliding glass door leading to a private balcony with beautiful eastern water views—perfect for morning coffee or relaxing evenings overlooking the river. Upstairs, the primary bedroom suite offers elevated water views and a private full bath. A second large bedroom and additional full bath complete the upper level, with washer and dryer conveniently located between the bedrooms. Residents of Queen’s Landing enjoy exceptional waterfront amenities including a private marina, swimming pool overlooking the Chester River, clubhouse, fitness center, tennis and pickleball courts, and scenic waterfront walking paths. Ideally located just minutes from shopping, dining, entertainment, the Cross Island Trail, and the Chesapeake Bay Bridge, this home is perfect as a full-time residence or weekend waterfront retreat on Maryland’s Eastern Shore. Schedule your private tour today!

34 Queen Anne Way, Chester

Listing courtesy of Taylor Properties. Contact:

$240,000
1 Beds ⋅ 1 Baths
Queens Landing - One bedroom condo with living room overlooking kitchen, good for entertaining. Private patio off bedroom with secured storage. Laundry is stackable located in bedroom. You will enjoy the Queen's Landing community clubhouse, marina, tennis court and pool and well as the trails in the community. Call today for your private showing.

8 Queen Victoria Way, Chester

Listing courtesy of Long & Foster Real Estate, Inc.. Contact:

$724,500
5 Beds ⋅ 4 Baths
Price improvement! Motivated sellers. This custom built home offers the perfect opportunity to live just minutes away from the Chesapeake Bay Bridge and Route 50, offering partial water views and a layout designed for both everyday living and effortless entertaining. The main level features 12 foot ceilings and oversized 6 foot windows that create bright, open living spaces. A vaulted morning room transitions seamlessly into a sunroom, providing flexible space for dining, relaxing, or working from home. The gourmet eat-in kitchen offers granite countertops, a substantial center island, pantry, and an open-concept design that opens into the family room and sunroom. The primary suite is generously sized, featuring a tray ceiling and a well-designed bath with custom tile shower and double vanity. The remaining four bedrooms share two jack-and-jill style bathrooms offering convenience for family and guests. Outdoor living is equally appealing, with an 800-square-foot wraparound deck ideal for entertaining. The property also offers space for a potential in-ground pool (buyer to verify with Planning & Zoning). Additional features include custom hardwood and tile flooring run throughout, tailored Roman blinds and wood shutters, new HVAC system, finished garage, and dedicated laundry room with new washer, dryer, and utility sink. A rare 1,820-square-foot crawl space with 4-foot ceilings, finished concrete floor, and indoor access provides plenty of additional storage. Built by local builder Lacrosse Homes with numerous upgrades, this well-maintained home offers immediate value in one of the most popular areas on the Eastern Shore - all with no HOA. Schedule your tour today.

1868 Roberta Dr, Chester

Listing courtesy of Coldwell Banker Realty. Contact: 4102638686
$299,900
3 Beds ⋅ 3 Baths
Estate Sale! Incredible opportunity to own one of the best values on Kent Island. Priced well below its potential, this 3-bedroom, 2.5-bath Dundee Harbor townhome offers approximately 1,400 square feet with an excellent upside. An updated home in the community sold for $365,000 in 2025, and this property offers outstanding potential for investors, flippers, or buyers looking to build equity. Estimated rental potential of approximately $2,400 per month (buyer to verify). Enjoy relaxing or entertaining on the rear deck, then take advantage of Dundee Harbor's water privileges on Piney Creek, including a private community pier for fishing, kayaking, paddleboarding, crabbing, or simply enjoying the waterfront. Just minutes from Kent Narrows, you'll love the waterfront restaurants, marinas, boat ramps, tiki bars, live entertainment, and Chesapeake Bay lifestyle. Conveniently located near shopping, everyday conveniences, and Route 50, this home offers an easy commute while delivering the relaxed Eastern Shore lifestyle buyers are looking for. Whether you're searching for an investment property, primary residence, or weekend retreat, this Estate Sale is an opportunity you won't want to miss. Schedule your showing today!

1025 Dundee Ct, Chester

Listing courtesy of RE/MAX Executive. Contact: 4432741900
$530,000
2 Beds ⋅ 3 Baths
Four Seasons @ Kent Island - 55+ Community - Price Improvement + Seller to Credit $4000 towards Capital Contribution Fee * Turn-key & Lovely 2nd Floor Condo in Elevator Building with 1 Car Garage plus 1 Car Outdoor Parking and Private, Secure Indoor Storage Area. This Chester Model offers 1900 sf with pond view and winter water views of Macum Creek. Enter to find an expansive, open floor plan featuring a beautiful white Kitchen with quartz counters, propane gas cooktop with range hood, wall oven + microwave combo and a huge Island that accommodates plenty of bar seating. Spacious Bedroom suites each with private full baths and generous closet spaces. The Primary bath has His 'n Her's double sinks with Moen fixtures, comfort height vanities, large vanity mirrors, medicine cabinets and a walk-in tiled shower with seat. The Primary bedroom features 2 closets; one walk-in-closet and one generous wall closet, a ceiling fan and a single French door to access the balcony. The 2nd Bedroom is large enough to hold a traditional sized bedroom set and features a tub/shower combo in the bath. The open Great Room is large, bright and has serene pond views and winter water views of Macum Creek with oversized sliders to a covered balcony. You will love the convenient laundry room located off the foyer area that accommodates the included full-sized GE washer and dryer. Elevator down to the Lobby level to your private garage and a just a few steps down the corridor is your private, keyed storage closet. This condo building features a secure lobby entrance and is impeccably decorated and maintained. Additionally, the 2nd floor has a common Club Room/Meeting Room great for socializing with your neighbors or as additional entertainment space. It features Public Water, Public Sewer, individually metered propane gas heat and cooking. All residents have access to the community amenities which include a huge 20,000 sf Club House with Billiards Room, Casual Lounge Area, Fitness Center, Party and Meeting rooms, and fabulous Indoor Heated Pool & Spa. Outside awaits a resort-like Pool, Cabana House, Private Beach Area, Outdoor Concert Space, Pier for Fishing and taking in the magnificent Chester River views & Kayak launch and Walking Trails. Pickle Ball enthusiasts you are in luck as there are Tennis Courts and Pickle Ball Courts for all, and grand kids can be entertained at a small Playground Area. Come tour today and see why this is THE place to be in Kent Island for 55+ living!

4000 Herons Nest Way Unit #22, Chester

Listing courtesy of RE/MAX Leading Edge. Contact:

$470,000
3 Beds ⋅ 3 Baths
New and improved price! This beautifully updated and well maintained home delivers exceptional value in the highly desirable Harbor View community—just two miles east of the Chesapeake Bay Bridge. Set on a picturesque 0.35‑acre corner lot, this 3‑bedroom, 2 full and 1 half bath home blends comfort, quality, and an unbeatable location. Inside, you’ll love the bright, updated kitchen featuring new countertops and backsplash, complemented by hardwood floors on the main and upper levels. A dramatic cathedral ceiling with skylights fills the home with natural light, creating an open and welcoming atmosphere. The spacious lower‑level family room offers a cozy retreat, while a flexible bonus room is perfect for a home office, guest room, or additional sleeping space. *Recent improvements add peace of mind and long‑term value, including a new roof (2019) with 50‑year shingles, new stove and hot water heater, and a new vinyl pool liner with a lifetime warranty. *Enjoy peace of mind with brand-new Pella tilt-in windows installed throughout the home in 2025, combining style, convenience, and energy efficiency. The pool is also equipped with a new robotic cleaner, making maintenance simple and hassle-free. The pool is open! Step outside to a fully fenced backyard oasis featuring a private in‑ground pool and deck— ready for summer entertaining or relaxing at home. Residents also enjoy access to the Harbor View community’s one‑acre field with pavilion and playground, perfect for gatherings and outdoor fun. Conveniently located just 20 minutes to Annapolis, 45 minutes to Baltimore, and under an hour to Washington, D.C., this home also offers easy access to Kent Narrows waterfront dining, the 6.5‑mile Cross Island Trail, and Queenstown Premium Outlets just minutes away. With updated features, transferable warranties, and a refreshed price, this home is move‑in ready and offers an outstanding opportunity to enjoy the best of Kent Island living. Schedule your showing today—this one is not to be missed.

1916 Stevens Dr, Chester

Listing courtesy of Coldwell Banker Realty. Contact: kelly.thompson@cbmove.com
$329,000
2 Beds ⋅ 3 Baths
DON"T MISS OUT on this super deal!! Owners have lowered the price by $10,000 and are willing to look at offers! Nothing to do but move in! Be in this spring to enjoy all that summer offers on the shore!! This roomy 2 bedroom, 2.5 bathroom end unit has been completely painted in a beautiful neutral shade and has new carpet throughout the living areas and new vinyl flooring in the kitchen. A propane fireplace highlights the great room turning chilly nights into cozy nights! On warm days, enjoy relaxing in the enclosed patio/porch or just being outside. Being an end-unit it offers lots of privacy. Any and all assessments have been paid by the owner, so you are ready to go and enjoy all the amenities that Queens Landing is known for...beautiful waterside pool, the club house with a party room, racquet ball court, exercise room, tennis courts, jogging trail, and more! Close to the cross-island trail, the Matapeake Dog Park, restaurants, schools, library...it is a wonderful place to live! Whether you are looking for a place to use as a vacation or weekend home, or as a year-round residence, this will suit both needs. It's situated in a great location...minutes to the Bay Bridge for any commuters to the western shore, and many airports, and an easy drive to the MD and DE beaches! Note: 4 pictures have been Virtually Enhanced!

54 Queen Caroline Ct, Chester

Listing courtesy of Long & Foster Real Estate, Inc.. Contact:

$479,000
2 Beds ⋅ 3 Baths
A price improvement has been made, making this unit the best value in the entire community. This home shows like a model with approximately $55,000.00 in upgrades. No need to wait for new construction this unit is ready for immediate occupancy. Love Where You Live! Experience resort-style living that blends comfort, luxury, and convenience—just steps from the waterfront. Enjoy peaceful mornings without the disruption of construction nearby. This highly sought-after first-floor condo is move-in ready and has been meticulously maintained, featuring numerous upgrades throughout. Step inside to an open, light-filled layout enhanced by crown molding, recessed lighting, and direct views of the lush greenspace with seasonal water glimpses. The gourmet kitchen and dining area are ideal for entertaining, offering a spacious island with seating, quartz countertops/bar, sleek wifi enabled appliances, and seamless flow into the living room. Unwind by the cozy fireplace or open the double sliding glass doors to your private patio—perfect for watching the sunrise, morning coffee, reading, or simply enjoying the peaceful natural setting. The owner’s suite offers both a walk-in and secondary closet, private patio access, and a luxurious en-suite bath with dual sinks and a spa-inspired frameless glass shower. The guest suite is bright and spacious, complete with its own en-suite bath, custom tilework, and large vanity. A bonus room with upgraded frosted glass doors provides the perfect space for a home office, workout area, or reading nook. Additional highlights include: LVP flooring throughout the entire home, interior access to a private one-car garage, and a secure storage unit. From your patio, take a stroll along the walking trail where you can take in the sights and sounds of nature to discover tranquil views and your kayak launch. The community also has direct access to the Kent Island Cross Island Trail. Many extra amenities to enjoy including an indoor heated pool, outdoor infinity pool, firepits, pickleball and tennis courts, dog park, and beautiful walking and biking trails. Live every day like you’re on vacation—this stunning condo offers the lifestyle you’ve been waiting for and is a must see to experience all of the upgrades! Water and sewer fees are already included in the owners monthly COA.

3000 Herons Nest Way Unit #11, Chester

Listing courtesy of Coldwell Banker Realty. Contact: 4102638686
$1,294,800
4 Beds ⋅ 4 Baths
*****Immediate Delivery*****WATERFRONT DEEP WATER ****Schedule showoing today! New Home, New Pier, New Pool!!!!!The Blue Heron is a new home design offered by Lacrosse Homes. The single family design features now one but TWO decks -- one from the second floor great room and the second from the third level primary bedroom suite. Take in all the beautiful sights and sounds of a Coastal Maryland lifestyle in this home built for entertaining and an enhanced lifestyle! There is room for everyone in this home, starting with a main level 2-car garage, rec room area, full bath & exercise/office -- this is your fun zone or whatever zone! The second level is light-filled and open with island kitchen featuring upgraded finishes, dining area, powder bath and great room with deck. You can ADD another deck on the rear of the home off the dining area if you're looking for more outdoor space. The third level features a laundry, three bedrooms including the spacious primary bedroom with updated bath and another stunning deck. The Blue Heron is a beautiful home and will serve a multitude of lifestyles. Explore your options today!

1757 Harbor Dr, Chester

Listing courtesy of Keller Williams Flagship. Contact:

$19,500
2 Beds ⋅ 1 Baths
This property, situated on a 0.17-acre lot, offers a blank canvas for your vision. Located in Queen Anne's County, the existing structure presents endless possibilities for the right buyer. Take advantage of the spacious lot size, perfect for outdoor activities or future expansion plans. Buyers are encouraged to perform their own due diligence to verify property details. Please note that access to 1405 Little Creek Rd is via 104 Little Creek Ct, followed by a left turn. Do not use or enter any neighboring driveways or properties as they are privately owned and clearly marked with “No Trespassing” signs. For safety reasons, please respect these boundaries.

1405 Little Creek Rd, Chester

Listing courtesy of The Parker Group. Contact: 3022176692
$275,000
Kent Island Waterfront on Cox Creek!! Public Sewer available, road frontage is 45ft. This is a flag lot with opening on the waterfront of 108 ft. This property does not have a pier, so please do not go on pier. This is the perfect lot to build your dream home. The natural environment has wildlife and waterfowl and as well as good fishing and crabbing. If you want a piece of the shore-life this is the property you have been looking for. Seller will consider holding a note for purchaser.

Parks Rd, Chester

Listing courtesy of Long & Foster Real Estate, Inc.. Contact:

$439,900
3 Beds ⋅ 2 Baths
PRICE Improvement...Discover the charm of this fully updated ranch in a serene, water-privileged community! With a spacious yard and an inviting open floor plan, this home features a stunning new kitchen complete with a large white granite island, sleek white cabinets, and stainless steel appliances. Sunlight floods the dining area through new sliding doors, while the generous living room is accented with stylish shiplap walls. There's Nothing Like NEW! Step onto the new flooring that leads you to three roomy bedrooms and two beautifully renovated full baths. Every detail has been attended to, with all-new windows, siding, plumbing, fixtures, electrical panel, light switches, septic work, water heater, doors, drywall, and a new HVAC system. With a recent roof and a dehumidified crawl space featuring a vapor barrier, this home is move-in ready—no worries, just settle in! The community enhances your lifestyle with access to four beaches, three boat ramps, a playground, ball fields, a basketball court, a picnic pavilion, a fishing pier, and plenty of opportunities for gatherings. This is the perfect place to create lasting memories!

1340 Queen Anne Dr, Chester

Listing courtesy of RE/MAX Executive. Contact: 4432741900
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