Queen Anne's County MD Homes for Sale

Get ready to be wowed!!! This home has undergone an extensive renovation over the last 5 years. The owners have poured so much love into this home, and it shows. On the interior one of the big standouts is the gourmet kitchen that will surely be the heart of the house. From the granite counters to the 10x4 quartz center island with seating and a build in beverage fridge, to the cozy build in window seating. The living area offers a great pellet stove for those chilly winter nights. Two bedrooms off the living area share a beautifully updated hall bath. The second sitting area is the family room that has a custom pine ceiling and direct access to your Trex deck to enjoy your morning coffee. But wait till you see the primary bedroom with a build in electric fireplace to cozy up too! Cold feet in the mornings no more with the heated primary bath floor, gorgeous shower with rainfall shower head and dual vanities. The exterior of this home is just as amazing as the interior. Get ready all you motorhead for this 30x46 outbuilding with 12 ft ceiling, 200-amp electric service, 2 automatic garage doors, a 18x10 bump out and a craft room for an added bonus! But wait there's more! The above ground pool was just purchased in 2022, with extensive decking for lounging about, or maybe an afternoon cocktail at your own tiki bar. Tired of having to purchase new plants every season well now you can safely store them over the winter in your own 10x12 greenhouse. The backyard even offers a great firepit area for those chilly evenings. Don't take my word for it come and experience all this property has to offer for yourself, you won't be disappointed!

2702 Harrington Rd, Chester

Listing courtesy of Rosendale Realty. Contact: 4107580333

$1,400,000

Welcome to the Taylor, a beautifully designed home that offers the perfect blend of comfort, style, and convenience. Available now, this home features 2 bedrooms, 2.5 baths, and a spacious 3-car garage, making it ideal for those seeking both functional living and elegant design. The open-concept layout is enhanced by a cozy fireplace and decorative ceiling beams that add warmth and architectural charm to the main living area. Step outside to the screened patio, where you can relax and take in peaceful waterfront views, creating the perfect setting for morning coffee or evening gatherings. The kitchen is equipped with a full suite of appliances, and a washer and dryer are also included, allowing you to move in with ease and enjoy modern convenience from day one. The primary bath features a spacious walk-in shower, offering a comfortable and spa-inspired retreat to unwind at the end of the day. 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.

216 Kingfisher Ln, Chester

Listing courtesy of Berkshire Hathaway HomeServices PenFed Realty - OP. Contact: 4102083500

$609,990

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 #2912, Chester

Listing courtesy of Berkshire Hathaway HomeServices PenFed Realty - OP. Contact: 4102083500

$599,999

Experience coastal living at its finest in this stunning 2024-built home located in the sought-after Romancoke community, just steps from the Chesapeake Bay. This beautifully appointed 4-bedroom, 2.5-bath home offers the perfect combination of modern design, comfort, and convenience. The spacious open-concept floor plan is ideal for entertaining, featuring seamless flow between the living, dining, and kitchen areas. High-end custom window blinds add a touch of elegance throughout, while the fully fenced backyard creates the perfect private retreat for relaxing, hosting gatherings, or enjoying time with family and pets. Perfectly situated on a quiet private road, this home offers a peaceful setting with easy access to the bay, making it ideal for boating, fishing, kayaking, or simply enjoying breathtaking waterfront sunsets. Connected to public sewer and built in 2024, you'll enjoy the benefits of newer construction with the peace of mind that comes with modern systems and finishes. Don't miss this opportunity to own a like-new coastal retreat in one of Kent Island's most desirable waterfront communities!

200 Ackerman Dr, Stevensville

Listing courtesy of Rise Real Estate, LLC. Contact: 2025569721

$645,000

5 Beds ⋅ 3 Baths

Your private resort awaits. From the moment you arrive, this stunning home commands attention with its timeless curb appeal, oversized corner lot, and impressive presence. Offering over 5,000 square feet across three levels, this is the perfect blend of luxury, comfort, and everyday functionality. Step inside to soaring ceilings, abundant natural light, and an open floor plan designed for both entertaining and daily living. The spacious two-story family room with a cozy fireplace flows seamlessly into the heart of the home, a beautifully appointed kitchen featuring a large center island, granite countertops, stainless steel appliances, abundant cabinetry, beverage refrigerator, and an oversized breakfast area overlooking the backyard. Whether you're hosting holiday dinners in the formal dining room, enjoying quiet mornings in the sun-filled living spaces, or gathering with friends around the kitchen island, every room has been thoughtfully designed for making memories. Upstairs, the expansive primary suite offers a true retreat with a spa-inspired ensuite bath, generous walk-in closet, and plenty of room to unwind. Spacious secondary bedrooms provide flexibility for family, guests, or a home office. The basement level adds even more living space with endless possibilities for a recreation room, fitness area, media room, or additional guest accommodations. Then step outside... The backyard is where this home truly shines. Imagine summer afternoons spent in the sparkling in-ground pool, evenings under the custom pavilion complete with an outdoor kitchen and bar, relaxing around the fire pit, and entertaining on the expansive paver patio, all surrounded by a fully fenced backyard offering privacy and space to enjoy. This isn't just a backyard, it's your own private vacation destination. Conveniently located near shopping, dining, parks, schools, and major commuter routes, this exceptional home offers the lifestyle you've been waiting for. Luxury. Space. Resort-style living. Welcome home.

122 Fair Brook Way, Centreville

Listing courtesy of RE/MAX Executive. Contact: 4432741900

$529,900

Enjoy Chesapeake Bay breezes, amazing water views and sunsets! Why pay waterfront prices and taxes when you can enjoy the same coastal lifestyle just steps from the water? Built in 2025 and impeccably maintained, this beautifully upgraded 3 bedroom, 2.5 bath home backs directly to Kentmorr Marina, offering beautiful Bay and marina views along with the rare opportunity to enjoy one of Kent Island's most desirable waterfront communities. The open-concept floor plan features luxury vinyl plank flooring throughout the main level, quartz countertops, an oversized farmhouse sink, white shaker cabinetry with soft-close drawers and cabinets, Craftsman-style interior doors, black designer fixtures, framed mirrors, and a spacious primary suite with a beautifully tiled shower and double vanity. A composite rear deck with vinyl railings provides the perfect place to relax and enjoy the marina views, while fresh landscaping, raised garden beds, and an expanded asphalt driveway add to the home's exceptional curb appeal. Located on a quiet street with no through traffic, you'll love being just steps from the private community beach where breathtaking Chesapeake Bay sunsets become part of everyday life. Bring your boat! Kentmorr Marina is right outside your back door (contact the marina for slip availability and pricing) or take a short stroll to Channel Side Restaurant for waterfront dining, live music, sandy beach seating, and a lively tiki bar. The Kent Island South Trail, nearby kayak launches, fishing piers, and Blue Heron Golf Course offer even more opportunities to enjoy the outdoors. Why wait for new construction? This exceptional property offers something a new build can't: a truly established waterfront community where the marina, private beach, waterfront dining, and unforgettable sunsets are all just steps from your front door. Ideally situated just minutes from the Bay Bridge, you'll enjoy convenient access to the Western Shore while embracing the relaxed coastal lifestyle of Kent Island.

520 Chesapeake Ave, Stevensville

Listing courtesy of Samson Properties. Contact: 7033788810

$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

$1,900,000

Steeped in history and surrounded by the timeless beauty of Maryland’s Eastern Shore, 1130 Old Love Point Road presents a once-in-a-generation opportunity to own an extraordinary family farm in the heart of Kent Island. Spanning approximately 36.73 acres, this remarkable property blends agricultural heritage, historic character, and exceptional future potential in one of the Shore’s most storied locations. At the center of the property sits an historic Victorian farmhouse dating to circa 1896, recognized by the Maryland Historical Trust as a historically contributing structure representative of the classic 19th-century Delmarva farmhouse. The home and grounds reflect generations of stewardship and offers tremendous opportunity for its next generation renovation, rehabilitation and future development prior to occupancy. Old Love Point Road itself carries a rich and fascinating history. Before the Chesapeake Bay Bridge connected Maryland to the Eastern Shore, Love Point served as one of the principal gateways to the Shore. Ferries, steamships, and rail lines once brought travelers from Baltimore and Annapolis to Kent Island, where they continued eastward across Maryland and Delaware. Love Point became known as a romantic waterfront destination and transportation hub, welcoming visitors arriving by ferry and the historic Queen Anne’s Railroad. The property’s location captures the spirit of that history while offering exceptional convenience to today’s modern traveler. Situated just minutes from Route 50 and the Chesapeake Bay Bridge, the farm offers easy access to Annapolis, Washington D.C., Baltimore, and the Delaware beaches while maintaining the peaceful charm of Eastern Shore living. Currently farmed and designated as prime farmland, the property is ideally suited for a gentleman’s farm, equestrian estate, vineyard, winery, agritourism venue, or luxury country retreat. The Development Analysis Report identifies a winery as one of the site’s most favorable and viable uses, noting that agritourism operations such as vineyards and wineries are specifically encouraged within Queen Anne’s County’s future agricultural economy plans. In addition to its agricultural and lifestyle appeal, the property, perhaps most importantly, offers substantial long-term development potential. Located within the County’s Suburban Estate zoning district and designated growth area, the site may support future residential subdivision opportunities, including large-lot estate development, clustered single-family communities, multifamily concepts, or additional residential lots under current moratorium guidelines. Whether envisioned as a private family compound, vineyard and winery destination, legacy investment, or future development opportunity, 1130 Old Love Point Road represents a rare chance to own a meaningful piece of Maryland’s Eastern Shore history — where the past, present, and future converge along one of Kent Island’s most iconic roads.

1130 Old Love Point Rd, Stevensville

Listing courtesy of Monument Sotheby's International Realty. Contact: (443) 746-2090

$2,769,000

5 Beds ⋅ 8 Baths

Designed by YSA Homes and Simply Wesley Interior Design of Annapolis, this extraordinary brand-new modern coastal farmhouse style smart-home offers over 6,148 square feet of thoughtfully designed living space, where every tile throughout the home was handpicked and expertly curated using top-of-the-line luxury selections. The kitchen is outfitted with premium, top-tier appliances including Wolf, creating a seamless blend of elevated craftsmanship, timeless design, and modern functionality at every turn. The property is permitted for a pool to be built. This stunning residence features five oversized bedrooms, each with its own expansive en suite bathroom, and three of the five have waterfront bay views. Totals include six full bathrooms, two half bathrooms, five gigantic bedrooms, 2 car oversized attached garage with rear entry door. An owner’s suite on the main level (with huge custom closet) provides everyday convenience, while the second level includes an additional owner’s suite with a massive custom walk-in closet, ideal for multi-generational living or extended guest stays. Upon entering the home, you are welcomed into an open-concept main level where the kitchen flows seamlessly into the dining and living areas, creating an ideal setting for entertaining and everyday living. The living room is anchored by a striking wireless water vapor fireplace, offering modern ambiance without heat or emissions. A main-level half bath adds convenience, while the primary suite features a spa-inspired oversized bathroom with a soaking tub, a large European-style walk-in shower, and exquisite designer finishes throughout. The second level impresses with a spacious great room, complete with a wet bar and an additional half bath, opening to a large upper-level deck designed for optimal water views and entertaining. Four generously sized en suite bedrooms are located on this level, two of which showcase stunning water views through oversized windows, filling the space with natural light. The lower level offers exceptional flexibility, featuring a walk-out basement with exterior sliding doors, a full bathroom, a dedicated laundry room, and ample space for a game room, den, home gym, or additional living areas. Ask the listing agent about available improvement and build-out options for the basement. Outdoor living continues on the main-level patio, with the option to expand or customize to suit your vision. Located on sought-after Kent Island, this home offers access to a true Chesapeake Bay lifestyle just approximately 20 minutes from historic downtown Annapolis. Enjoy nearby waterfront parks, marinas, beaches, and miles of scenic walking and biking trails along the Cross Island Trail. Golf enthusiasts will appreciate proximity to Blue Heron Golf Course with membership options available, as well as the nationally recognized Queenstown Harbor Golf Links featuring two championship courses. Residents can easily enjoy all that downtown Annapolis has to offer, including boutique shopping, waterfront dining, sailing culture, festivals, and the charm of the historic district and U.S. Naval Academy. Just minutes away, **Queenstown Premium Outlets—featuring Calvin Klein, J.Crew, and other popular brand-name retailers—*provide convenient access to everyday shopping. Kent Island is also home to waterfront dining, local crab houses, and Love Point Vineyards, while Terrapin Nature Park and Matapeake Beach offer stunning Chesapeake Bay views. Conveniently positioned for commuting to Baltimore and Washington, D.C., this location blends coastal living with everyday accessibility. This is not just a home, this is a coastal lifestyle.

414 Bay Dr, Stevensville

Listing courtesy of Cummings & Co. Realtors. Contact: (410) 823-0033

$222,000

3 Beds ⋅ 1 Baths

Property is located on an acre in a rural setting yet within a 1/2 mile to Route 50. Detached 2 car garage with electric in rear of property. Built-ins remain for extra storage throughout home. Some updates have been made to bath but still elements of the past give it a vintage vibe. Property strictly sold as is. HUD CASE 244-033541. Please see website hudhomestore for details

518 Arrington Rd, Queenstown

Listing courtesy of Thurston Wyatt Real Estate, LLC. Contact: 4103206785

$399,000

2 Beds ⋅ 2 Baths

Waterfront Living on Thompson Creek – Rare End-Unit Townhome Fantastic opportunity to own an end-unit waterfront townhome with direct views of Thompson Creek, complete with an assigned pier featuring power and water. Inside, gleaming hardwood floors flow through the kitchen and living room. The main level offers a convenient bedroom, while upstairs you'll find a huge loft-style primary suite complete with a spacious primary bathroom featuring an oversized walk-in shower and an equally impressive walk-in closet. A versatile bonus room offers flexibility as a 3rd bedroom or home office. The kitchen offers ample counter space and storage alongside a large dining area, perfect for entertaining. Step outside to a spacious deck to soak in the water views, plus a second private balcony off the primary bedroom. With western exposure, enjoy breathtaking sunsets over the creek every evening. The HOA maintains the pier as well as all exterior upkeep of the home, including the roof and siding, offering true low-maintenance waterfront living. Ideally located on Kent Island, just a half mile to Route 50 and minutes to two shopping centers featuring Food Lion, Target, and a variety of restaurants. Incredible value at $399,000 for waterfront living with a private pier. Furnishings are available for purchase separately, excluding personal items.

101 Marion Quimby Dr, Stevensville

Listing courtesy of Engel & Volkers Annapolis. Contact: (443) 292-6767

$379,000

2 Beds ⋅ 1 Baths

Charming Cape Cod home offering both residential comfort and commercial potential, beautifully updated with modern finishes while maintaining its classic character. This move-in-ready property features 2 bedrooms, 1 full bathroom, an inviting sunroom entry, and luxury vinyl plank flooring throughout. The updated kitchen showcases stainless steel appliances, an induction range, new refrigerator, granite countertops, and refreshed cabinetry. Recent improvements include the bathroom, double-pane windows, roof, siding, HVAC system, well system, electrical panel, and front entry door. The property also features an oversized detached garage with side entry and a spacious asphalt driveway for added convenience. Minutes to Kent Island, close to major hwy. A rare opportunity to own a versatile property with endless possibilities!

3801 Main St, Grasonville

Listing courtesy of Fairfax Realty Select. Contact: 7035932381

$675,000

4 Beds ⋅ 2 Baths

Photos Coming Soon! Welcome to this beautifully maintained one-level rancher, perfectly situated on a private 1-acre lot. Offering 2,441 square feet of comfortable living space, this home provides 4 bedrooms, 2 full baths, and has an inviting open floor plan designed for everyday living and entertaining. Thoughtful architectural details, including coffered ceilings and crown molding, add character and elegance throughout the main living areas. The spacious living room is anchored by a fireplace with a wood-burning insert, creating a warm and welcoming atmosphere. The well-appointed kitchen offers abundant cabinet and counter space and opens seamlessly to the main living areas. The dining area is spacious, ideal for hosting family and friends. A large four-season room, complete with heating and cooling, provides additional year-round living space and overlooks the lovely backyard. Step outside to enjoy the expansive deck and pergola-covered seating area, perfect for relaxing or entertaining. The fully fenced backyard offers plenty of room for outdoor activities while maintaining a sense of privacy. A detached two-car garage features a heated and cooled bonus room above, ideal for a home office, gym, hobby room, or additional flex space. Major improvements completed within the past five years include a newer HVAC system, roof, gutters, and kitchen updates, providing added value and peace of mind. This exceptional property combines the convenience of one-level living with modern updates, versatile spaces, and a peaceful setting—ready for you to call it home.

2200 Bennett Point Rd, Queenstown

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

$350,000

Welcome to 213 Elm Street in Centreville. Be Sure to Click the Virtual Tour!! This property has been meticulously cared for by the current owners, and it shows! The property sits on .23 acres. Pride of ownership shines through in this gem of a home. This property gives you plenty of space both inside and out. You will be welcomed home every day by your screened in, front porch and its classic brick floor. There is hardwood flooring throughout the first and second floor. The living room includes a wood burning fireplace that was serviced and repaired in 2024 and has worked beautifully since. The property backs up to a nice, wooded area with plenty of peace and quiet. Enjoy tons of natural light in the spacious kitchen where granite countertops are partnered with a modern backsplash, Refrigerator, built-in microwave and stove. This home has three spacious bedrooms, 1 full and recently updated bathroom and an additional half-bathroom upstairs. The second floor could serve as a spacious owner’s suite with its very own sitting room, walk-in closet, updated half-bath and bedroom. The sitting area upstairs comes with custom-made built-in shelving. The unfinished lower level provides you with even more space for storage or it can be your very own blank canvas to finish and increase your living space. The laundry area is on the main floor, and the washer and dryer will stay with the home. The roof was replaced in 2020. The deck was updated and stained in 2025. The storage shed stays with the property, which has even more space. High Speed Talkie internet is available. It is in the town of Centreville, and it is minutes away from local shops. This is an Amazing Home! It is turn-key and ready to Welcome its New Owners.

213 Elm St, Centreville

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

$1,250,000

5 Beds ⋅ 3 Baths

Classic Colonial Overlooking the Golf Course in Prospect Bay. Welcome to this beautifully maintained brick-front Colonial, perfectly positioned with picturesque golf course views in the sought-after Prospect Bay community. Filled with natural light from oversized windows, the open floor plan offers the perfect balance of comfortable everyday living and elegant spaces for entertaining. The home features four spacious bedrooms upstairs, plus a first-floor office or optional fifth bedroom, making it ideal for guests, multi-generational living, or working from home. Hardwood floors, two fireplaces, a formal dining room, and generously sized living spaces create timeless appeal throughout. The spacious primary suite offers a peaceful retreat with a walk-in closet and private bath. A three-car garage provides ample storage and convenience. Step outside to your private backyard oasis, where a heated swimming pool, expansive deck with a covered awning, and sweeping golf course views create the perfect setting for relaxing or entertaining. Enjoy watching golfers from your backyard while soaking in the peaceful surroundings. Living in Prospect Bay means enjoying resort-style amenities, including an 18-hole championship golf course, clubhouse with members-only restaurant and bar, marina with boat launch, swimming pool, tennis and pickleball courts, playground, and a full calendar of year-round social events. This exceptional home offers the perfect blend of classic elegance, modern comfort, and an unbeatable lifestyle.

4 Prospect Bay Dr W, Grasonville

Listing courtesy of Coldwell Banker Realty. Contact: 4102638686

$409,000

Welcome Home! Eastern Shore Cape Cod awaits new Owners. Awesome 3 bed 2 bath home has a little bit of something for everyone. Cozy floor plan features entry level bedroom plus 2 large 2nd floor bedrooms. Granite counters, carpet and vinyl plank flooring throughout. Outside features backyard patio for entertaining and large fenced rear yard with room for garden, firepit or critters. The real gem is the 24x36 garage connected by covered breezeway. Room for vehicles, boat, workshop, man cave or she shed. Also included is an outlet for RV hook-up. Conveniently located close to public boat ramps, The Crumpton Auction, DE tax Free shopping and Rt 301 for commuters. Professional pics to come. Minor excluded items

100 Clark Ct, Millington

Listing courtesy of Berkshire Hathaway Homeservice Homesale Realty. Contact: (800) 383-3535

$998,000

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

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

$190,000

Vacant lot in upcoming community.

Baltimore Drive Dr, Stevensville

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

$534,900

5 Beds ⋅ 3 Baths

Welcome to 126 Meadowcroft Drive — a beautifully updated 5‑bedroom, 2.5‑bath home tucked in one of Centreville’s most desirable neighborhoods. With a brand‑new roof within the last few years and newer dual‑zoned HVAC units, this spacious home offers modern comfort, low maintenance, and peace of mind from day one. Step inside to find fresh updates throughout, including stylish finishes, gas fireplace and a bright, inviting layout perfect for both everyday living and entertaining. The main level features generous living spaces, an updated kitchen, and a flexible floor plan suited for today’s lifestyle. Upstairs, five well‑sized bedrooms provide ample room for family and guests. The primary suite offers its own private bathroom with a tile shower and soaking tub, while an additional full bath ensures convenience for all. Outside, enjoy a quiet setting with space to relax on the back patio complete with a firepit—ideal for anyone seeking both comfort and room to unwind in a well‑established community. Move‑in ready and thoughtfully updated, 126 Meadowcroft Drive delivers ease of ownership and timeless small‑town charm. Don’t miss this opportunity!

126 Meadowcroft Dr, Centreville

Listing courtesy of Chesapeake Real Estate Associates, LLC. Contact:

$749,900

Nestled within the prestigious Oyster Cove community, this exquisite 3rd floor Penthouse corner residence offers a harmonious blend of luxury and comfort, perfectly situated along the serene Kent Narrows/ Prospect bay. Served by elevator, the contemporary architectural style is complemented by high-end finishes throughout, including luxury vinyl plank flooring and elegant built-ins that enhance the open floor plan. Step inside to discover a spacious family room that seamlessly connects to a gourmet kitchen, featuring upgraded countertops and modern appliances, including a sleek electric range and a convenient dishwasher. The inviting breakfast area is perfect for casual dining, while the primary bath offers a private retreat with sophisticated fixtures. Enjoy the tranquility of river views from your porch, where you can unwind and soak in the picturesque surroundings. The property boasts deeded private 40 foot boat slip, ideal for boating enthusiasts, and a community pool for leisurely afternoons. Additional amenities include a gated entrance, ensuring privacy and security, along with beautifully maintained common grounds and walking paths. With three generously sized bedrooms and a cozy electric fireplace, this home is designed for both relaxation and entertaining. The community offers a wealth of recreational options, including tennis courts, pickle ball and picnic areas, enhancing the luxurious lifestyle that Oyster Cove provides. Experience the ultimate in waterfront living, where every detail has been thoughtfully curated for your enjoyment.

130 Oyster Cove Dr Unit #130, Grasonville

Listing courtesy of Coldwell Banker Waterman Realty. Contact: (410) 643-5005

$6,000,000

For Sale or Lease! Positioned at the gateway to Kent Island, 1406 Main Street commands 1.78 acres with dual frontage on U.S. Route 50/301 and Main Street — among the most visible corners on Maryland's busiest Eastern Shore corridor. The site holds a three-building commercial complex of approximately 12,034 square feet: a large retail store fronting Route 50, a separate retail building addressing Main Street, and service space totaling nine drive-in bays.

1406 Main St, Stevensville

Listing courtesy of SVN/Miller Commercial Real Estate. Contact: 410-543-2440

$929,990

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

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

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

$635,000

Mallard Run - This Colonial features 4 large-size bedrooms 2.5 bath home featuring 2,708 sq ft of living space. The open floor plan is great for entertaining, The luxury vinyl flooring is throughout the first floor. The kitchen is bright white cabinets with granite countertops also featuring an island and eat up bar area. You will also, enjoy the sunroom and beautiful backyard. The mud room and laundry off the two-car garage is great for storage. Close access to schools and local parks and trail, this is the location you have been looking for.

376 Web Foot Ln, Stevensville

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

$435,000

Grasonville - This home offers 3 bedroom and 3 baths located on 1.2 acres. The garage space is amazing for all of your projects. Featuring two garages, one car oversized attached is heated and with an oversized two car detached 24x 30 with heat and AC. The house roof is a 50-year shingle with about 7 years on it. You will enjoy the fall and the rest of the summer in the large screened in porch. NO Hoa or restrictions. This is the home you have been looking for. Call today for your showing appointment.

407 Sawmill Ln, Grasonville

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

$345,000

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

$349,000

Welcome to easy, one-level living in a location that truly gives you the best of both worlds! Just minutes from the charm and downtown, walkable, waterfront lifestyle of Chestertown, yet tucked within the highly sought-after Queen Anne’s County School District, this beautifully updated 3-bedroom, 2-bath home is ready to impress. Step inside to find a spacious, open feel highlighted by a massive living room—perfect for gathering, relaxing, and entertaining. The heart of the home is the stunning, renovated kitchen, offering plenty of space to cook, host, and make everyday living feel a little more special. Both bathrooms have been tastefully updated, giving the home a fresh, modern feel throughout. Enjoy the ease of all one-level living, along with a screened-in porch that’s perfect for morning coffee, evening unwinding, or hosting friends without the bugs. Outside, you’ll love the great yard—ideal for play, pets, or simply enjoying the peaceful setting. Need extra space? The large detached 2-car garage offers plenty of room for vehicles, storage, hobbies, or a workshop setup. This water-oriented community offers private access to the Chester River just a couple of blocks away—perfect for kayaking, fishing, or soaking in those Eastern Shore sunsets. There’s also a voluntary property owners association at just $30/year if you’d like to participate. If you’ve been looking for space, updates, and that relaxed Eastern Shore lifestyle—all in a convenient location—this one checks all the boxes!

123 Heath Rd, Chestertown

Listing courtesy of Chesapeake Real Estate Associates, LLC. Contact:

$345,600

3 Beds ⋅ 1 Baths

Cutest little rancher in the cutest little town! Welcome to Queenstown! Walk to the bank, post office, restaurant, waterfront overlook or even the GOLF COURSE! Quaint smalltown living at its finest! Brand new composite deck boards and vinyl rails. Brand new paver walkway and steps being completed. Updated kitchen!!! Newer cabinets! Newer quartz countertops! Newer appliances! Newer LVP flooring! Newer fence! Nice corner lot with water views! Hardwood and ceramic floors. Easy commute on and off of 301 to Annapolis, Easton, or wherever!

6808 Main St, Queenstown

Listing courtesy of Coldwell Banker Waterman Realty. Contact: (410) 643-5005

$382,750

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

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

$589,000

4 Beds ⋅ 2 Baths

Welcome Home to 729 Kimberly Way, nestled in the highly sought-after waterfront community of Cloverfields on Kent Island—where thoughtful updates, exceptional outdoor living, and versatile bonus space combine to create a home you’ll be proud to call your own. This beautifully maintained 4-bedroom, 2-bath raised rancher welcomes you with mature landscaping, vibrant flower beds, a spacious half-circle driveway, and outstanding curb appeal. The extended driveway leads to an oversized detached garage with generous storage above, offering endless potential to be finished into additional workspace, a private office, hobby room, or the perfect retreat to fit your lifestyle. Step into your own backyard oasis, thoughtfully designed for both entertaining and everyday enjoyment. Stamped concrete walkways and patios lead to an expansive two-tier deck, complemented by covered outdoor living space, mature trees for added privacy, and beautifully maintained landscaping that creates a peaceful setting. With ample parking and inviting outdoor spaces, this property is ideal for hosting family and friends or simply relaxing after a day on the water. Inside, you’ll find numerous updates and energy-efficient features throughout. The lower level offers a spacious family room centered around a charming wood-burning stove, creating a warm gathering place while helping reduce heating costs during the cooler months. Paired with the home’s highly efficient geothermal heating and cooling system—a rare and valuable feature on Maryland’s Eastern Shore—you’ll enjoy year-round comfort and exceptional energy savings. The lower level also features a full bathroom, welcoming tiled entry, and updated mechanicals, including a new water heater and new washer and dryer. Upstairs, engineered hardwood flooring flows throughout the main living areas, adding warmth and timeless character. The updated kitchen offers modern appliances and opens seamlessly to the dining area, where sliding glass doors lead to the expansive rear deck overlooking the private backyard. The upper level includes three comfortable bedrooms, including a spacious split primary suite with abundant closet space. The beautifully updated bathroom showcases ceramic tile flooring, an oversized tiled shower, and a relaxing soaking tub. Fresh paint, updated lighting, and meticulous care make this home truly move-in ready. Living in Cloverfields means enjoying some of Kent Island’s most desirable community amenities, including a private sandy beach, marina, boat ramp, fishing pier, swimming pool, clubhouse, playgrounds, and parks—all just minutes from the Chesapeake Bay Bridge, waterfront restaurants, shopping, and everything the Eastern Shore lifestyle has to offer. If you’ve been searching for a home that offers comfort, flexibility, energy efficiency, and an unbeatable waterfront community, 729 Kimberly Way is an opportunity you won’t want to miss.

729 Kimberly Way, Stevensville

Listing courtesy of Samson Properties. Contact: 7033788810

$2,850,000

5 Beds ⋅ 5 Baths

Set on Forty Five picturesque acres of prime agricultural land with extensive tillable acreage, this exceptional Five bedroom, Four and one half bath brick colonial blends timeless design with modern versatility and waterfront charm. Privately situated on a quiet cove just off the mouth of the Chester River, the property offers a rare combination of space, functionality, and lifestyle appeal. Inside, the home features a thoughtfully designed layout ideal for both everyday living and entertaining. A main-level en-suite provides excellent flexibility for multi-generational living or private guest quarters, while an additional upper-level en-suite enhances comfort and convenience for visitors. The spacious primary suite serves as a true retreat, complemented by well-proportioned secondary bedrooms and multiple full baths. Refined living spaces include a formal dining room, a dedicated home office perfect for remote work, and an inviting screened porch overlooking the water—an ideal setting to relax and take in the tranquil views. The nearly fully finished basement expands your living options with generous space for recreation, hobbies, or a workshop. Recent upgrades—including a new roof and septic system—offering peace of mind, while the 2-zone HVAC system ensures efficient year-round comfort. Outdoors, enjoy the in-ground pool surrounded by a patio, perfect for entertaining or unwinding, along with open acreage that offers endless possibilities for farming, equestrian use, or a private rural lifestyle. Complete with a Twocar garage and located in a highly desirable waterfront setting, this property presents a rare opportunity to own a versatile estate that balances luxury living, scenic beauty, and agricultural potential.

1810 Love Point Rd, Stevensville

Listing courtesy of Monument Sotheby's International Realty. Contact: (410) 525-5435

$359,000

Live like you're on vacation every day in the highly desirable Queen's Landing community on Kent Island! Nestled along the Chester River, this charming lake-front townhome offers the perfect blend of comfort, style, and resort-style living. You'll love the gorgeous remodeled kitchen featuring granite countertops, a large center island, breakfast bar, custom built-ins, and a pass-through to the living room—perfect for cooking, entertaining, and everyday living! The spacious living room features a cozy fireplace and opens to a beautiful enclosed pond-front porch where you can relax with your morning coffee while taking in the peaceful water views. The primary suite offers incredible lake views and a private bath, plus you'll find two additional bedrooms and the convenience of second-floor laundry. Enjoy the incredible community amenities: Community pool, Pickleball & tennis courts, Fitness center, Clubhouse, Adjacent to Castle Harbor Marina Queen's Landing on Kent Island is the perfect getaway—whether you're looking for a second home or a primary residence. Enjoy resort-style living with beautiful surroundings and all the charm of the Eastern Shore.

29 Queen Mary Ct, Chester

Listing courtesy of Rosendale Realty. Contact: 4107580333

$162,000

Bring your dream home, and your builder to this beautiful 1-acre lot! This perc-approved homesite allows for a basement, giving you the flexibility to design the home you've always envisioned. Enjoy the opportunity to build in a peaceful setting while creating a home tailored to your lifestyle.

441 Eagle Manor Dr, Church Hill

Listing courtesy of Chesapeake Real Estate Associates, LLC. Contact:

$999,990

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

$600,000

Welcome to one of Sudlersville's most extraordinary heritage homes, a magnificent Queen Anne Victorian that beautifully honors its historic character while embracing the comforts of modern living. Following an extensive 2019 renovation that left virtually no system untouched, this remarkable residence has been thoughtfully reimagined for today's lifestyle while preserving the timeless architectural details that make it truly one of a kind. Set on more than an acre beneath majestic centuries-old shade trees, this magical family estate commands attention with its soaring turret, five striking bay windows, and deep, sweeping wraparound porch that invites you to slow down and savor every season. Overlooking the neighborhood park, the setting is as enchanting as the home itself, nestled within the quintessential Hallmark town of Sudlersville, where the historic train station now serves as a museum and the soft rumble of the grain train passing through town a few times each week provides a nostalgic reminder of the community's rich heritage. Inside, soaring ceilings, exquisite millwork, and an impressive foyer introduce an unexpectedly open floor plan designed for both gracious entertaining and everyday living. The expansive kitchen is a true gathering place, featuring stunning custom cabinetry that extends to the ceiling with thoughtfully designed pull-out drawers, a dramatic designer backsplash, updated stainless steel appliances, many with transferable warranties, and a large picture window above the sink that fills the space with natural light. The kitchen flows seamlessly into the dining room, beautifully nestled within one of the home's signature bay windows. The adjoining family room creates an airy, connected living space rarely found in historic homes, while multiple rooms open directly onto the wraparound porch, blurring the line between indoor and outdoor living. A dedicated office surrounded by windows offers an inspiring workspace, and the butler's pantry with wet bar provides the perfect staging area for effortless entertaining on the porch and patios. The main-level primary suite offers exceptional convenience with a spacious ensuite bath featuring a soaking tub and separate shower, while a powder room completes the first floor. Upstairs, four additional bedrooms include a private ensuite guest suite and a beautifully appointed hall bath. Fresh new carpeting enhances the upper-level bedrooms, while two of the bedrooms are graced by the home's distinctive bay window bump-outs, creating expansive sitting areas bathed in natural light and showcasing the architectural character that makes this residence so special. A walk-up third floor offers abundant storage along with the enchanting turret room, an unforgettable space ready to become a library, reading retreat, artist's studio, or simply a breathtaking lookout over the surrounding landscape. The immaculate cellar provides exceptional storage, while the park-like grounds are designed for year-round enjoyment with patios, arbors, expansive lawns, a welcoming fire pit tucked beneath towering centuries-old shade trees, and two substantial outbuildings, including a garage and a detached studio currently used as a fitness space. Rich in history yet thoughtfully transformed for thoroughly modern living - including a Level 2 EV Tesla charger! This spectacular Queen Anne Victorian is far more than a home, it is a once-in-a-lifetime opportunity to become the next steward of one of Sudlersville's most treasured residences.

108 Maple Ave, Sudlersville

Listing courtesy of Northrop Realty. Contact: (302) 947-9100

$629,990

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

$675,000

Welcome to 144 Wye Knot Road, where peaceful country living meets everyday convenience. Nestled on 3 private, level acres, this spacious cape cod offers the perfect blend of comfort, functionality, and open space, all within easy reach of Easton, Annapolis, the Bay Bridge, and major commuter routes. A tree-lined paved driveway welcomes you home, while the classic exterior, complete with a full front porch, dormer accents, and an attached side-load two-car garage, creates timeless curb appeal. Inside, you'll find over 2,200 square feet of thoughtfully designed living space featuring four bedrooms, two-and-a-half bathrooms, and an ideal floor plan for both everyday living and entertaining. Formal living and dining rooms flank the welcoming foyer, while the rear of the home opens to a dramatic family room with soaring cathedral ceilings, abundant natural light, rich wood flooring, and a cozy gas fireplace. The kitchen serves as the heart of the home, offering Corian countertops, stainless steel appliances, a center island, generous cabinetry, and an informal dining area overlooking the backyard. Step outside to the spacious deck, perfect for morning coffee, summer barbecues, or simply relaxing while taking in the peaceful surroundings. Upstairs, you'll find four generously sized bedrooms, including a spacious primary suite. The finished bonus room above the garage provides exceptional flexibility and is ideal for a recreation room, home office, fitness room, playroom, or 4th bedroom/2nd primary suite. Additional features include dual-zone HVAC (replaced within the last 10 years), a tankless gas water heater (replaced within the last 10 years) and an EV charger-ready garage. The true highlight of this property is the land. Level, usable acreage like this is increasingly difficult to find and provides endless opportunities for gardening, recreation, entertaining, future outdoor amenities, or simply enjoying the peace, privacy, and beauty of country living. If you've been searching for a home that offers room to breathe without sacrificing convenience, 144 Wye Knot Road is an exceptional opportunity to enjoy the best of Maryland's Eastern Shore lifestyle.

144 Wye Knot Rd, Queenstown

Listing courtesy of RE/MAX Leading Edge. Contact:

$1,300,000

Coming soon to Kent Island Estates — a rare opportunity to own directly on the Eastern Bay. This 5-bedroom, 3.5-bath Coastal-style home offers 2,704 square feet of finished living space across three levels, with soaring high ceilings, rich hardwood floors, and crown molding and wainscotting carrying throughout. The gourmet kitchen features upgraded countertops and premium appliances, with a breakfast area perfect for casual mornings, plus a fireplace in the main living area for cooler evenings. Professional Photos to come. Multiple bedrooms open directly onto a screened-in porch and private balconies, framing sweeping views of the Chesapeake Bay from nearly every angle. Step outside to your own private pier and dock, putting boating, fishing, and bay access just steps from the back door — while an in-ground pool adds resort-style living to your own backyard. Pella double-pane windows fill the home with natural light while keeping energy costs in check. Set on a 0.32-acre lot with no HOA, this home sits in the sought-after Kent Island Estates community, with access to a neighborhood park, the South Kent Island Trail, and quick proximity to local restaurants, grocery stores, and the Bay Bridge for an easy commute to Annapolis. Waterfront opportunities like this on the Eastern Bay are rare — don't miss your chance.

366 Queen Anne Rd, Stevensville

Listing courtesy of Real Broker, LLC - Chester. Contact: 8554500442

$600,000

Welcome to this stunning home in the picturesque 55+ Community of Bay Bridge Cove - the place for Kent Island living at its best, so close to the waters of the Chesapeake Bay. This 3-bedroom, 3-bath home offers so many upgraded features. Conveniently located across from the community center and backing up to quiet, tree-lined space, you are steps away from enjoying all the amenities the neighborhood has to offer. Welcoming you at the front of the home is your own private courtyard, with space to sit and relax or socialize with friends under the strings of cafe lights. Walk inside to the warm-toned luxury wood plank vinyl floors throughout the entire first floor; abundant light spills in to accent the paneled foyer with upper crown molding. The roomy kitchen features soft-close cabinets/drawers with lots of storage, pull-out trash and recycle bins, a corner cabinet with lazy-susan shelving, stainless steel appliances, premium countertops and backsplash, under-the-counter lighting, and updated cabinet knobs and pendant lights. The main level great room has plenty of space for a large dining table and your comfortable living room furniture, and features a cozy gas fireplace (and includes a convenient wall mount for your TV). Step into the bright and airy sunroom at the back of the home - make it your book nook, office, or a spot to enjoy your guests. The primary bedroom features a tray ceiling, 2 walk-in closets (one is huge!), and a private bath with tiled shower and ceramic tiled flooring. The 2nd bedroom on the first floor connects to the hall bath. A sizable laundry room includes upgraded Samsung appliances, shelving, and a storage closet. Upstairs you'll find a relaxing retreat with a large loft area, a bedroom with walk-in closet, and a full bath. A bonus feature of this home is the beautifully enhanced loft wall on each side with added railing, making this space safe for the little ones while maintaining the line of sight to the first floor. With ceiling fans throughout, added storm doors on the front and back with pull-down screens, unique custom blinds on all windows matched perfectly to the function of each room, and an irrigation system for low-maintenance gardening, this home may be the perfect one you've been looking for! This thriving community has it all - a calendar of activities and outings, bocce and pickleball, picnics at the crab shack, a pool, indoor gym, library, game rooms, community garden and fresh herb garden, walking paths around the beautifully landscaped ponds, and quick access to the Cross Island Trail right next to the neighborhood. There's so much to do here!

222 Moorings Cir Unit #126, Stevensville

Listing courtesy of The KW Collective. Contact: 4435741600

$789,990

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

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