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$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

$224,900
3 Beds 2 Baths
Rarely available first floor condominium centrally located on Kent Island and in the Thompson Creek Community. Enjoy all the amenities of this water access community including the pool, tennis courts, clubhouse, and within a short walking distance to the water where you sit in a quiet community of proud homeowners. As you arrive, you will notice the peace and tranquility this community offers. Open the door and you will be greeted by the ample living room which features a cozy corner fireplace, plenty of sunlight that fills the home and sliders leading to the private covered balcony where you can enjoy views of the sunsets. Take advantage of the small outside storage closet. The kitchen provides everything a passionate cook needs to prepare even the most elaborate of meals. The primary bedroom features large windows, an ample closet and its private full bath. The other two bedrooms are equal in size and also offers sufficient space for a growing family. Another full bath can be found in the hallway. This condo offers PLENTY of parking and SUPER convenient location - less than 5 minutes to the Bay Bridge, Restaurants, Shopping, and ALL that the Island life has to offer.

1603 Marion Quimby Dr, Stevensville

Listing courtesy of Northrop Realty. Contact: 4105310321

$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 pride of ownership, offering opportunity and authenticity. 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 also 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

$99,000
4 Beds 1 Baths
Located in the small town of Queen Anne, this 4-bedroom, 1-bath farmhouse is in need of extensive repairs and renovation and is being sold as-is. The home was previously used as a rental property and offers an opportunity for investors, contractors or buyers looking for a project property with potential. Features include a covered front porch, off-street parking and a small storage shed. The property shares a well with the neighboring home, which is also available for purchase (13704 Main Street). Enjoy a location less than 3/4 mile from Hillsboro Landing with access to Tuckahoe Creek for boating and fishing and under 5 miles from Tuckahoe State Park. The park is known for its 60-acre lake, presenting fishing and boating opportunities, playgrounds, and more than 20 miles of hiking, biking, and equestrian trails.

13706 Main St, Queen Anne

Listing courtesy of Benson & Mangold, LLC. Contact: (410) 745-0415

$139,000
4 Beds 1 Baths
Opportunity awaits in the quaint town of Queen Anne. This 4-bedroom, 1-bath farmhouse offers plenty of potential. The home features double side porches, off-street parking and classic farmhouse character, but is in need of updates and repairs. Previously used as a rental property for many years, this property could present an opportunity for an investor, contractor or buyer looking to restore and build equity. Property is served by a shared well with the adjoining property (13706 Main Street), which is also being offered for sale. Conveniently located less than 3/4 mile from Hillsboro Landing, providing access to Tuckahoe Creek for boating and fishing, and less than 5 miles from Tuckahoe State Park. Known for its 60-acre lake, the park offers boating, fishing, playgrounds, and over 20 miles of scenic hiking, biking, and equestrian trails.

13704 Main St, Queen Anne

Listing courtesy of Benson & Mangold, LLC. Contact: (410) 745-0415

$514,900
3 Beds 4 Baths
72HR KICK OUT. Tucked away in the peaceful Cloverfields community, this beautifully updated Cape Cod with sunroom and second floor addition blends classic charm with modern comfort. Nearly every inch of the home has been renovated, including a full interior remodel, brand-new kitchen and bathrooms, two added full baths (for a total of four!), new flooring, lighting, paint, windows, roof, skylights, HVAC systems, exterior doors, and more. There’s even a new second laundry room, front porch, paved driveway extension, encapsulated crawlspace, privacy landscaping, and custom closet system. The property also includes two storage sheds, one with electricity — perfect for a workshop, hobby space, or she-shed. Inside, the open floor plan creates an inviting space that’s great for both everyday living and entertaining. The family room feels warm and welcoming with recessed lighting and a cozy electric fireplace. The kitchen is designed for both style and function with custom storage, granite countertops, ample table space, a pantry, and ENERGY STAR appliances. The home offers three spacious bedrooms, including a relaxing primary suite with a spa-like bathroom. Extras like wainscoting, skylights, and main level bedroom add even more comfort and character throughout the home. Outside, the level 0.34-acre lot offers plenty of room to enjoy the outdoors, whether you’re relaxing on the large deck and patio or hosting friends and family. And the location is hard to beat — just four blocks from the Chester River with access to amazing Cloverfields amenities including a community pool, beach, basketball courts, boat ramp, boat slips, playgrounds, and scenic trails. This home offers the perfect mix of modern updates, outdoor living, and laid-back community charm — truly a place you’ll love coming home to.

702 Dixon Dr, Stevensville

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

$59,999
Situated on a quiet road, this half-acre property offers a great opportunity to enjoy the Eastern Shore lifestyle. Community water access to the Chester River is located at the end of the road and includes a boat ramp, making it easy to enjoy boating, fishing, crabbing, or paddle boarding right nearby. Located within the Queen Anne’s County school district and just minutes from downtown Chestertown. A mobile home currently exists on the property and is believed to be approximately 60 years old. Buyer to verify condition and habitability of the mobile home or remove at buyer’s discretion. Seller has no knowledge or information regarding the mobile home. Original well and septic are present on the property; buyer to verify condition and functionality of both.

228 Merganser Dr, Chestertown

Listing courtesy of Benson & Mangold, LLC. Contact: 4108226665

$549,000
3 Beds 2 Baths
Coming soon — brand new construction opportunity! This thoughtfully designed ranch-style home will be breaking ground soon and offers the chance to secure a brand-new home before construction begins. Featuring convenient one-level living, this home will include an open floor plan with vaulted ceilings and quality finishes throughout. The kitchen is planned to feature quartz countertops, stainless steel appliances, a center island, and ample cabinet space, opening to the spacious living and dining areas—ideal for everyday living and entertaining. The primary suite is designed as a private retreat with a spacious bedroom, walk-in closet, and ensuite bath featuring a double vanity and oversized shower. Additional bedrooms provide flexibility for guests, family, or a home office. Other highlights include a dedicated laundry room, generous storage, and an attached 2-car garage. Situated on a spacious lot, buyers may have the opportunity to make selections depending on the stage of construction. Get in early and make this upcoming new construction home yours before it’s built!

Tenneessee, Stevensville

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

$549,000
3 Beds 2 Baths
Coming soon — brand new construction opportunity! This thoughtfully designed ranch-style home will be breaking ground soon and offers the chance to secure a brand-new home before construction begins. Featuring convenient one-level living, this home will include an open floor plan with vaulted ceilings and quality finishes throughout. The kitchen is planned to feature quartz countertops, stainless steel appliances, a center island, and ample cabinet space, opening to the spacious living and dining areas—ideal for everyday living and entertaining. The primary suite is designed as a private retreat with a spacious bedroom, walk-in closet, and ensuite bath featuring a double vanity and oversized shower. Additional bedrooms provide flexibility for guests, family, or a home office. Other highlights include a dedicated laundry room, generous storage, and an attached 2-car garage. Situated on a spacious lot, buyers may have the opportunity to make selections depending on the stage of construction. Get in early and make this upcoming new construction home yours before it’s built!

Baltimore Dr, Stevensville

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

$590,000
4 Beds 4 Baths
THE ASSUMABLE 3 1/8% MORTGAGE ON THIS HOUSE WOULD SAVE A BUYER SEVERAL HUNDRED DOLLARS ON EACH MONTHLY MORTGAGE PAYMENT. A historic home made new again! Recent improvements include a brand new HVAC system installed in 2023, a water heater replaced in 2022, a new roof and gutters completed in April 2026, refinished butcher block countertops, freshly painted kitchen cabinets, updated stainless steel appliances, added storm windows for comfort and efficiency, newly added ceiling fans on the covered front veranda, and thoughtful renovations throughout that help blend historic charm with everyday modern living. Steeped in history and full of soul, the historic Queenstown School House, known as Double School House Number 6 and built in 1834, feels less like a house and more like a story carefully carried through generations. Expanded, renovated, and thoughtfully updated over the years, it still holds onto the details that make historic homes unforgettable. Original wavy glass window panes catch the sunlight beautifully while added storm windows help preserve comfort and efficiency. Look closely and you’ll even spot square nails still visible in portions of the flooring, quiet reminders of craftsmanship from another era. Exposed beams, wide plank hardwood floors, brick accents, enchanting natural light, and inviting living spaces give the home a feeling that’s difficult to recreate. Every room seems to catch sunlight differently throughout the day, giving each space its own personality. It’s rare to find a home that blends modern farmhouse comfort, country living, vintage style, and historic schoolhouse character in a way that feels this natural and instantly like home. Just off the kitchen, the dining room creates an easy flow for everyday meals or gatherings with friends and family. Near the front of the home, a cozy study offers the perfect spot for reading or quiet moments, while the family room beside it feels welcoming for game nights and long conversations. The main level also includes two half baths along with a practical laundry and pantry area that helps everyday living stay organized. In the kitchen, refinished butcher block countertops, a farmhouse sink with an unlacquered brass faucet, freshly painted cabinets, stainless steel appliances, and a pellet stove tie everything together beautifully while adding supplemental heat in the kitchen during colder months. Upstairs, you’ll find four bedrooms, two full bathrooms, and a flexible recreation area that can easily become an art studio, hobby room, workout space, reading area, or whatever fits your lifestyle best. Outside, the property unfolds beautifully in every direction. The covered front veranda, complete with a hanging porch swing and newly added ceiling fans, feels like the kind of place where coffee lasts longer and neighbors stop to wave while walking their dogs or heading through town on errands. That’s part of what makes Queenstown feel so special. It’s welcoming, connected, and the kind of small town where people still genuinely know one another. A classic picket fence surrounds the property while the gardens come alive throughout the seasons with raised beds, David Austin roses, mature elderberries, gooseberries, thornless blackberries, hydrangeas, lilacs, evergreen jasmine, and four varieties of peonies that bloom for nearly a month every spring. Just outside the sunroom, a classic English pea gravel gardenscape creates a beautiful outdoor dining area for holidays, celebrations, or evenings under the stars. Located in historic Queenstown, this home is close to Queenstown Pizzeria, Salt Wellness, Queenstown Harbor Golf Course, the town boat ramp, a hidden beach, waterfront dining, outlet shopping, and nearby parks. Nearly two centuries old, it still feels comfortable, loved, and full of life.

7121 Main St, Queenstown

Listing courtesy of EXP Realty, LLC. Contact: 8888607369

$499,900
4 Beds 3 Baths
Cloverfields - Location, Location, Location! Welcome to a home that truly offers the best of convenience, community, and Eastern Shore living. Ideally situated just one mile from the Bay Bridge, this property places you within walking distance of all local schools—from pre-kindergarten through 12th grade—as well as the Cross Island Trail and Love Point Park, both just a 3-minute stroll away. Shopping, dining, and everyday conveniences are only minutes from your doorstep, making it easy to enjoy everything Kent Island has to offer while embracing the relaxed coastal lifestyle. Located in the highly desirable Cloverfield's community, residents enjoy exceptional amenities including a community pool, clubhouse, private beach, and marina—all included with the remarkably low HOA. Inside, you'll find a spacious and flexible floor plan offering 4–5 bedrooms and the option for a second-floor laundry area. Thoughtful updates and improvements throughout make this home truly move-in ready. Features include beautiful bamboo flooring, granite countertops, Andersen windows, fresh paint, new luxury vinyl plank flooring in the foyer and primary bathroom, and new carpet in the primary bedroom. Major improvements provide peace of mind for years to come. The front porch has been professionally repointed, the garage door is brand new, and the expansive 16' x 20' deck has recently been redecked—perfect for outdoor entertaining. Additionally, the crawl space has been professionally encapsulated, and a sump pump and dehumidifier have been installed. The heart of the home is the large kitchen, offering ample space for a dining table and everyday gathering. An open dining and living area creates the perfect setting for holidays, celebrations, and family get-togethers. From the welcoming beveled-glass entry door to the beautifully established perennial flower beds, every detail adds warmth and charm. This is more than just a house—it's a lifestyle. Come experience the perfect blend of comfort, convenience, and community in one of Kent Island's most sought-after neighborhoods.

606 Kimberly Way, Stevensville

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

$2,450,000
4 Beds 5 Baths
Sited on Cox Creek with 369 feet of waterfront, this elegant contemporary residence offers 2.3 private acres, spectacular western exposure, and breathtaking sunset views. Thoughtfully designed to maximize water vistas from nearly every room, the home features 4 bedrooms, 3 full baths and 2 half baths, and approximately 4,717 square feet of refined living space. The gourmet kitchen is appointed with rich custom cabinetry, granite countertops, upgraded stainless steel appliances, and a gas cooktop, creating an ideal setting for both everyday living and entertaining. Custom hardwood flooring spans the main level, complemented by two fireplaces and timeless architectural details throughout. The luxurious main-level primary suite offers serene water views, multiple walk-in closets, and a recently renovated spa-inspired bath. A beautiful three-season room overlooks the creek, providing the perfect space to relax and enjoy the tranquil setting. There is also ample room to add a pool. Upstairs, three additional bedrooms and two full baths provide comfortable accommodations for family and guests, with three of the four bedrooms enjoying water views. The upper level has been recently updated with luxury vinyl plank flooring in place of carpet. Additional highlights include mature professional landscaping, a temperature-controlled wine room, a 3-car garage, a new roof, private pier with electric and water, boat lift, jet ski lifts, and riprap shoreline protection. Located in the desirable Southwind community, residents enjoy amenities including a boat launch, boat storage area, tennis courts, walking trails, and a clubhouse — all conveniently located near shopping, dining, and more.

2832 Cox Neck Rd, Chester

Listing courtesy of Coldwell Banker Realty. Contact: kelly.thompson@cbmove.com

$499,900
4 Beds 4 Baths
From the moment you arrive, this charming Cape Cod feels like home. Built in 2002 with 2x6 construction and beautifully updated in 2021, it offers the perfect mix of comfortable living and thoughtful upgrades. Inside, you’ll find 4 spacious bedrooms and 3.5 baths, 9' ceilings, along with a warm, welcoming interior featuring hardwood floors, recessed lighting, and touches of stained glass that add just the right amount of character. The kitchen truly is the heart of the home, with upgraded countertops, stainless steel appliances, and a center island that’s perfect for everything from quick breakfasts to gathering with friends and family. The living room invites you to slow down and relax, centered around a beautiful marble fireplace that makes chilly evenings feel extra cozy. You’ll also appreciate the convenience of main-level laundry, plus an additional hookup in the basement. Downstairs, the partially finished basement creates a fun and flexible space to enjoy—complete with a home theater, a fully stocked bar with seating, a full bathroom, and plenty of room left for storage. Set on 0.65 acres and backing to trees, the outdoor space offers a peaceful, private setting. Whether you're enjoying your morning coffee on the deck or winding down at the end of the day, it’s easy to feel at home here. The outbuilding and shed provide plenty of extra space for hobbies, tools, or storage. With an attached garage and plenty of driveway parking, this home checks all the boxes for comfort, space, and everyday ease. Seller's home warranty is good through September and is transferrable. If you’ve been looking for a home that feels inviting the moment you walk in, you won’t want to miss this one.

120 Archer Ln, Millington

Listing courtesy of Cross Street Realtors LLC. Contact: 4434803453

$450,000
3 Beds 2 Baths
This light-filled Mozart model has three bedrooms and two bathrooms. Living and dining rooms as you enter the home, and the kitchen and family room are to the left, with granite countertops and recent appliances. This is a cozy area, with a fireplace and access to the custom brick patio and rear yard. There is a small walled-off space near the family room which could be used as an office. The owner's suite has new carpeting, a huge walk-in closet, and the adjoining bathroom has a corner soaking tub, separate shower and double vanity. The guest bedroom and bathroom are located down a short hallway, and the third bedroom is at the opposite end of the house from the kitchen. It would be suitable for a hobby room, large office or library.  With beautiful hardwood floors, fresh neutral paint, new bedroom carpeting and a new roof, this home is ready for its new owner. Just a short walk to the clubhouse and pool, you can park your car and have a stroll.  Symphony Village is a community of 395 houses, with mature trees, lush landscaping, and a magnificent clubhouse where myriad activities are available, including frequent social gatherings, holiday picnics, card games, mahjong, language and dance classes, billiards, a vibrant artisan group with  classes and shows, plus a quarterly reception for residents and friends to view the latest art creations. There are bocce courts, tennis and pickle ball courts, and a putting green with many keen players. The outdoor pool is open from May to September, and you can find several shady seating spots if you wish. The indoor heated pool is open year-round, and features a lift chair for those who need it. Water aerobics classes are offered weekdays indoors  or outdoors depending on the season.  Centreville is the Queen Anne County seat, with a historic courthouse, several restaurants, grocery stores, and other essential services. Easy drive to Easton, St. Michaels, Annapolis and Chestertown, and the beach is not too far away.

149 Sonata Way, Centreville

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

$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

$994,000
5 Beds 3 Baths
Welcome to this stunning custom home overlooking the 10th green in the prestigious Prospect Bay community. Situated on a beautiful one-acre lot, this residence offers over 3,000 square feet of living space with 4-5 bedrooms and an ideal floor plan for everyday living and entertaining. The dramatic two-story foyer welcomes you into a thoughtfully designed home featuring elegant architectural details, including tray and vaulted ceilings. The bright kitchen features abundant cabinetry, a center island, pantry, and sunny morning room, plus a separate formal dining room. Open to the kitchen, the inviting family room offers bamboo flooring, a gas fireplace, custom built-ins, and access to the expansive deck overlooking the backyard and golf course. The spacious primary bedroom includes a large walk-in closet and private bath with a soaking tub, dual vanities, and a walk-in shower. Four additional bedrooms provide flexibility for guests, a home office, or multigenerational living, including one bedroom conveniently located on the main level.  Enjoy the best of Eastern Shore living with outdoor spaces designed for relaxing and entertaining. Barbecue on the large deck or gather with family and friends for a traditional Maryland crab feast in the screened gazebo while taking in peaceful golf course views. Additional highlights include a three-car garage, oversized parking pad, main level heat pump replaced in 2021, and crawl space encapsulated in 2025. Prospect Bay residents enjoy outstanding resort-style amenities, including an 18-hole championship golf course, clubhouse restaurant, swimming pool, tennis and pickleball courts, boat ramp, pro shop, and an active social calendar. Ideally located just minutes from the Chesapeake Bay Bridge, this lovely home offers the perfect combination of golf, boating, and relaxed coastal living.

14 Fairway Is, Grasonville

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

$605,000
3 Beds 3 Baths
Welcome to Perry’s Retreat, an exquisite coastal-inspired community in the heart of Grasonville, where luxury living meets the charm of the Chesapeake Bay lifestyle. Built by Ryan Homes, this stunning Craftsman-style residence showcases exceptional curb appeal with a covered front entry, handsome stone accents, classic siding details, and a spacious two-car garage, creating a warm and timeless first impression. Inside, a spacious and welcoming foyer sets the tone for the home’s thoughtfully designed interior. Nearby, elegant French doors open to a versatile flex room, perfect as a private home office, formal dining room, or optional guest bedroom. Beautiful luxury vinyl plank flooring spans the main level, complemented by recessed lighting throughout the home and plush carpeting upstairs for added comfort. The thoughtfully designed open floor plan is anchored by an extraordinary great room and show-stopping chef’s kitchen that truly define the heart of the home. Designed with impeccable attention to detail, the gourmet kitchen features crisp white cabinetry beautifully contrasted by a striking navy center island, a stunning blue herringbone tile backsplash, and premium Wolf appliances including an induction cooktop and M Series double wall ovens. A custom coffee station with pull-out drawers and pocket doors offers both convenience and seamless style, while the floor-to-ceiling pantry with pull-out storage provides exceptional organization. The oversized island with breakfast bar seating and adjoining dining area flow effortlessly into the spacious family room, highlighted by a dramatic floor-to-ceiling board and batten accent wall with a 50” Dimplex linear electric fireplace. The main-level primary suite is a luxurious retreat featuring a coffered ceiling, expansive walk-in closet, and spa-inspired ensuite bath with dual vanities and a beautifully appointed walk-in shower. A second sunny main-level bedroom is conveniently served by a full hall bath with a tiled tub/shower combination. Upstairs, flexible loft space offers endless possibilities for a media room, family room, hobby space, or playroom. An additional bedroom featuring custom millwork headboard detailing capped off with a picture shelf, and a spacious walk-in closet provides both charm and functionality. A third full bath and a large storage room complete the upper level. Outdoor living is equally impressive. Step from the dining area onto the covered patio, ideal for relaxing evenings, entertaining, and cookouts overlooking the beautifully landscaped, fully fenced backyard. Stone garden beds, dual side gates, privacy vinyl fencing, and a 10x14 storage shed add both beauty and functionality to the outdoor space. Perry’s Retreat offers the charm of a quaint, thoughtfully designed neighborhood complete with sidewalks, classic lamppost lighting, beautifully maintained green spaces, and a neighborhood park with playgrounds that create a warm and inviting community atmosphere perfect for evening strolls, outdoor recreation, and connecting with neighbors. Perfectly situated in Grasonville, a picturesque Chesapeake Bay waterfront town known for its proximity to the Kent Narrows marinas, waterfront dining, boutique shopping, and coastal charm, Perry’s Retreat offers an unmatched lifestyle. Enjoy the peaceful beauty and Eastern Shore tranquility of a bucolic waterfront setting while being just a hop, skip, and a jump across the Bay Bridge to Annapolis in approximately 15 minutes, with convenient commuting access to both Washington, D.C. and Baltimore. This exceptional location truly offers the best of both worlds, an idyllic Eastern Shore lifestyle paired with effortless access to all the conveniences and opportunities of Maryland’s Western Shore.

115 Pathfinder Cir, Grasonville

Listing courtesy of Northrop Realty. Contact: 4439213900

$549,900
3 Beds 2 Baths
Symphony Village a premier 55 plus active adult community which is well desired and nicely located just on the edge of Centreville. If you are looking for the perfect 55 plus community this is it! Active adults loving life and enjoying the community this neighborhood provides from Happy Hours, Pools, events, pickleball, the gym and more. You will always see neighbors walking, riding bikes and enjoying life in the Village! This home is one of the few which gives you privacy out back backing to the woods offering you complete peace. Relax on your back patio and watch the wildlife, listen to the birds, drink your coffee, grill or have nice gatherings with your friends. This amazing and well kept home is ready for a new owner and you will not be disappointed! Offering 3 nice sized bedrooms an d2 full bathrooms with a nice open concept this floor plan allows you the option to set it up how you choose. Offering a ton of natural lighting with all of the windows this home exudes fresh and airy feelings. The kitchen has a ton of cabinets perfect for the person who loves to cook and plenty of space for your kitchen table. You will enjoy the gas fireplace all winter long as it is a great feature. The garage offers 2 parking spaces and a huge room above the garage with ample storage. This neighborhood's HOA includes lawn care, trash, snow removal, and the FANTASTIC Club house! Come and take a look and see why everyone loves Symphony Village! You will want to live here too!

126 Encore Ct, Centreville

Listing courtesy of EXP Realty, LLC. Contact: 8888607369

$399,000
3 Beds 1 Baths
Nestled along the banks of the Chester River in the historic waterfront town of Millington, this enchanting 1955 cottage offers a rare opportunity to embrace the beauty of Eastern Shore living. Steeped in tradition and situated on the original Rings End Farm property, this special home is rich with local history and timeless character. Surrounded by lush landscaping, mature trees, abundant wildlife, and sweeping river views, the property invites a lifestyle defined by nature, tranquility, and endless days on the water. Eagles soar overhead, herons wade along the shoreline, and the peaceful rhythm of the river creates an extraordinary natural setting in every season. Inside, timeless charm meets comfortable living with thoughtfully designed spaces that celebrate the surrounding landscape. The spacious kitchen features a sunlit breakfast room with large windows framing peaceful backyard and river views, while a separate dining room creates the perfect setting for intimate gatherings. An RO system under the kitchen sink provides added convenience and water quality. The inviting living room is filled with warmth and character, complete with a skylight and cozy wood-burning stove. A generous family room opens directly to an expansive brick patio, seamlessly blending indoor and outdoor living. Three comfortable bedrooms, a large laundry/mud room with side entrance and additional storage, and two substantial outbuildings provide both functionality and flexibility for everyday life and waterfront adventures. Recent improvements include a new well pump installed in 2025 and a new thermostat also installed in 2025, offering additional peace of mind. The true magic of the property unfolds at the water’s edge. Stroll down to your private pier and floating dock (5 foot MWL) where days are spent embracing the very best of waterfront living. Cruise the river by boat, launch a kayak or paddleboard, spend quiet mornings crabbing, or cast a fishing line into the Chester River, known for catfish, spot, sunfish, yellow perch, and other local catches. Whether enjoying an afternoon on the water or simply taking in the breathtaking sunsets from the pier, the river becomes an extension of everyday life and a constant source of recreation. The town of Millington adds to the charm, offering two public parks and a public community swim club complete with pool and tennis courts. Conveniently located to shopping and dining in both Millington and nearby, Chestertown, Middletown DE, the property also offers easy access to Route 301, connecting you effortlessly to Eastern Shore destinations, Wilmington in just about an hour, and Philadelphia in approximately 90 minutes. Whether you're seeking a peaceful weekend retreat or a year-round waterfront sanctuary, this remarkable property captures the essence of refined Eastern Shore living while honoring the history and heritage of the original Rings End Farm.

251 Rings End Rd, Millington

Listing courtesy of Northrop Realty. Contact: 4102956579

$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

$295,000
2 Beds 1 Baths
Discover the charm of this delightful bungalow nestled in the heart of Centreville Heights. This beautifully maintained 2-bedroom, 1-bathroom home boasts hardwood floors that flow seamlessly throughout, creating a warm and inviting atmosphere. The eat-in kitchen is perfect for those early morning coffees or evening cocktails, including a cooktop, wall oven, dishwasher, and refrigerator, perfect for culinary enthusiasts. Step outside to enjoy your private deck, ideal for enjoy those beatiful mornings or evening gatherings. The spacious lot offers ample outdoor space, complemented by street lights that enhance the neighborhood's inviting ambiance. A convenient shed provides additional storage for your gardening tools or outdoor equipment. The interior features include an attic for extra storage, a cozy dining area, and energy-efficient double-hung windows that fill the home with natural light. The basement, equipped with a drainage system and sump pump, offers potential for additional living space or a workshop. Located in a vibrant community, this home is just minutes away from local parks, providing endless opportunities for outdoor activities and relaxation. The neighborhood is known for its friendly atmosphere and accessibility to essential public services. This property is not just a house; it's a place to create lasting memories. Embrace the lifestyle you've always wanted in Centreville Heights!

313 Oak St, Centreville

Listing courtesy of Cummings & Co. Realtors. Contact:

$999,000
4 Beds 3 Baths
Big reduction Three Homes! With each independent and separate addresses, all on 48 acres. The lands include woods and a pond. The primary home is 2800 square feet just recently remodeled. Open concept living all the rooms are very spacious with a kitchen with tons of storage and lots of counter space. There is an office space as well so many options to use as additional bedrooms or hobby room. A laundry area that is a room not a closet. The HVAC system was just replaced on the main home, as many other features of this house. Number two house was just put on the property in 2025, Clayton Holmes three bedrooms two baths would make a wonderful in-laws house or a rental. Number three house sits to the back of the property again is its own separate structure, is a remodled single wide. Would make an excellent income, Property or a caretaker residence. This property offers so many options it’s unlimited. It also includes a 30 x 50 insulated pole barn with a concrete floor electric separate meter and pitcher pump. Two pasture areas exist with shelter for live stock they currently have goats. This is a absolutly one of a kind property if you want to have a Equine center lots of room to build a indoor arena or to raise livestock. The entire family can live here and have there own house. The current owners have greatly improved the property it is now waiting for the next care takers to see what they do with this special property and its new use.

420 Duhamel Corner Rd, Marydel

Listing courtesy of Benson & Mangold, LLC.. Contact: (410) 479-0777

$229,000
3 Beds 1 Baths
Opportunity Knocks in Sudlersville! Situated on 1.41 acres, this 3-bedroom, 1-bath home presents a rare chance to create value in an area where renovated homes are selling for significantly more. This property is in need of extensive renovation, but the upside potential makes it an excellent opportunity for investors, renovators, or buyers looking to design a home on a spacious lot. The former garage has been converted to storage space, offering flexibility for future use or redesign. With the right vision, this property can be transformed into something truly special. Sold strictly AS-IS, WHERE-IS. Seller has never occupied the property. Buyer responsible for verifying all utilities, systems, and property condition. Bring your vision and make it your own!

1826 Sudlersville Rd, Sudlersville

Listing courtesy of 212 Degrees Realty, LLC. Contact: 3013438538

$575,000
3 Beds 3 Baths
*BIG PRICE IMPROVEMENT ON THIS BEAUTY* SELLER IS ALSO OFFERING CLOSING ASSISTANCE!Welcome to Bay Bridge Cove, an active adult 55+ community designed for comfort, convenience, and low-maintenance living. Residents enjoy exceptional amenities including a clubhouse with outdoor pool, fitness center, lounge, library, meeting space, and game room, along with walking trails, scenic ponds, pickleball and bocce courts, a crab shack, and community vegetable and herb gardens. Ideally located near Historic Annapolis, shopping, dining, recreation, and major commuter routes including Rt. 50, Rt. 97, the Bay Bridge, Washington, D.C., Baltimore, and the Eastern Shore. This beautifully upgraded Easton model by award-winning McKee Builders offers quality craftsmanship, energy efficiency, and thoughtful design throughout. A private gated paver courtyard creates a warm welcome, while the spacious rear deck overlooks open green space and mature trees for a peaceful outdoor setting. Inside, this meticulously maintained home offers approximately 2,000 square feet with 3 bedrooms, 3 full baths, a versatile loft, and a 2-car garage. The gourmet kitchen is appointed with upgraded cabinetry featuring pull-out shelving and soft-close doors and drawers, granite countertops, decorative backsplash, Kohler undermount stainless sink, and upgraded stainless steel appliances. Additional improvements include upgraded flooring, renovated baths, and a tankless on-demand water heater. The open and airy interior is filled with natural light from two skylights in the main living area. Architectural details include crown molding, chair rail accents, soaring foyer ceilings, cathedral ceilings in the dining and family rooms, and a tray ceiling in the primary suite. The spacious primary retreat includes two closets and a beautifully updated bath. Two additional bedrooms and two full baths, with one bedroom and bath on each level, offer flexibility for guests or multigenerational living. The loft provides ideal space for a home office, den, or reading area. A large conditioned crawl space with interior access offers excellent storage. Please note: public records do not reflect the correct square footage. Approximate finished living area is 2,000 square feet. CALL ME TODAY FOR YOUR SHOWING!

324 Moorings Cir Unit #108, Stevensville

Listing courtesy of Clark & Co Realty, LLC. Contact: 410-490-2183

$649,900
4 Beds 3 Baths
Welcome to life on Kent Island in the sought-after Cox Creek Landing community—where coastal charm meets everyday convenience. With water access on the community pier and available BOAT SLIP EASEMENT WITH BOAT LIFT! CCL neighborhood is perfect for embracing the Chesapeake Bay lifestyle, all just minutes from shopping, dining, and local amenities. From the moment you arrive, the inviting front porch sets the tone—an ideal spot to relax with a morning coffee or unwind in the evening while enjoying the peaceful surroundings. Inside, the home is thoughtfully designed for both comfort and functionality. The main level features a desirable first-floor primary suite with a full bath, along with an additional half bath for guests. A private home office with elegant glass doors provides the perfect space for remote work or quiet retreat. The heart of the home is the open-concept kitchen and family room, where vaulted ceilings create an airy, inviting atmosphere. Just beyond, a sun-filled morning room offers the perfect place to start your day, overlooking the beautifully landscaped backyard. Step outside to a brick patio surrounded by lush, mature landscaping, creating a private outdoor oasis ideal for entertaining or relaxing. A side-load two-car garage adds both curb appeal and practicality. Upstairs, you’ll find an additional three generously sized bedrooms and a full bath, offering ample space for all with 4 bedrooms throughout. This home perfectly blends style, space, and location—offering a rare opportunity to enjoy the best of Kent Island living in a waterfront-access community.

303 Creeks End Ln, Stevensville

Listing courtesy of Paul Wesley Real Estate. Contact: 7032822709

$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: