Queen Anne's County MD Homes for Sale

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. 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

$500,000

Beautiful Home with Finished Waterproofed Basement & Chesapeake Bay Water Access! Don't miss this exceptional home featuring a professionally waterproofed basement with a transferable warranty. The lower level offers a spacious recreation/living room, full bath, bedroom, and abundant storage space—perfect for guests, extended family, or a home office. You are first greeted by a cozy front porch overlooking the spacious corner lot. The main level boasts an open-concept floor plan with luxury vinyl plank flooring throughout, custom-built shelving, and a welcoming living room highlighted by a fireplace with a wood stove insert. The spacious kitchen is designed for both everyday living and entertaining, featuring granite countertops, white cabinetry, a center island, and a dining area. Step outside to enjoy the large backyard complete with a deck, patio, and oversized storage shed. An oversized garage provides ample space for vehicles, hobbies, tools, or workshop projects. Located in a desirable community offering a playground and water privileges on the Chesapeake Bay, you'll enjoy easy access to the beach and breathtaking sunset views. This home combines comfort, space, and a fantastic lifestyle opportunity. Schedule your showing today—this one won't last long!

101 Birch Road, Stevensville

Listing courtesy of RE/MAX Executive. Contact: 4432741900

$499,000

Welcome to 336 Timber Lane—a beautifully maintained Colonial offering the space, comfort, and lifestyle today's buyers are looking for, all in a convenient Grasonville location just minutes from Kent Island and the Bay Bridge. With over 2,100 square feet, this move-in ready home features 4 bedrooms, 2.5 baths, hardwood flooring, a cozy fireplace, and a spacious, flowing floor plan designed for everyday living and effortless entertaining. The bright kitchen overlooks the family room, creating the perfect gathering place for holidays, game nights, or simply spending time together. Upstairs, the spacious primary suite offers a peaceful retreat with a walk-in closet and private en-suite bath, while three additional bedrooms provide flexibility for family, guests, a home office, or fitness space. Step outside and enjoy a generous backyard with plenty of room for entertaining, gardening, play, or simply relaxing after a day on the water. One of Grasonville's best-kept secrets is the lifestyle. You'll enjoy quick access to marinas, waterfront restaurants, boating, fishing, shopping, and Route 50—all while experiencing less congestion than many neighboring communities. Best of all, this home offers an incredible opportunity to enjoy the Eastern Shore lifestyle while getting more home for your investment than many comparable properties on Kent Island. Whether you're commuting, raising a family, or looking for a place to enjoy everything the Chesapeake Bay has to offer, 336 Timber Lane delivers the perfect blend of space, value, and location.

336 Timber Ln, Grasonville

Listing courtesy of Samson Properties. Contact: 7033788810

$344,900

2 Beds ⋅ 3 Baths

Motivated seller! Experience relaxed waterfront living in this beautifully updated townhome condominium overlooking scenic Thompson Creek, where stunning water views, community amenities, and an exceptional coastal lifestyle come together. Thoughtfully renovated and move-in ready, this waterfront retreat blends modern upgrades with inviting indoor and outdoor spaces designed for both everyday comfort and, entertaining.The main level welcomes you with an updated kitchen featuring granite countertops, stainless steel appliances, and abundant cabinetry. Just beyond, the sunken living room creates a warm and inviting atmosphere highlighted by a beautiful brick gas fireplace (ready for propane hookup if desired and easily convertible back to wood-burning), a custom wet bar, and seamless access to the spacious waterfront deck, perfect for enjoying peaceful sunsets over the creek. Recent improvements totaling approximately $20,000 include luxury vinyl plank flooring, new carpet upstairs, fresh interior paint throughout, and new blinds, giving the home a refreshed, modern feel. Upstairs, you'll find two generously sized bedrooms, ample closet space, and 2.5 baths, including a spacious primary suite with a well-appointed ensuite bath. A private balcony off the primary bedroom provides tranquil water views, breathtaking sunsets, and peaceful views of the community walking paths. Outdoor living is truly at the heart of this property. Enjoy boating, fishing, kayaking, swimming, and waterfront recreation just moments from your door. Residents have access to a community pool, clubhouse, tennis courts, scenic walking and jogging paths, nearby marinas, and multiple boat launch options, including Thompson Creek Landing within walking distance and convenient access to Kent Island. Situated along the banks of Thompson Creek, this home offers picturesque views of the water, mature trees, and surrounding natural beauty, creating a peaceful setting perfect for relaxing, entertaining, or simply enjoying the waterfront lifestyle. Additional conveniences include unassigned off-street parking and a well-maintained community offering exterior building maintenance, professional management, and trash service, providing low-maintenance living and added peace of mind. Whether you're searching for a full-time residence, weekend retreat, or investment opportunity, this home offers the perfect blend of comfort, recreation, and coastal charm in an unbeatable waterfront setting.

1102 Marion Quimby Dr, Stevensville

Listing courtesy of Redfin Corp. Contact: 3016586186

$425,500

3 Beds ⋅ 4 Baths

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

807 Auckland Way, Chester

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

$275,000

MOTIVATED SELLER. Occupied duplex generating immediate rental income in Centreville. Two 1BR/1BA units with one unit occupied and the other on the market for a new tenant. Features include hardwood and laminate flooring, washer hookup in unit B, public water and sewer, shared driveway, and street parking. Recent updates include an updated roof (2023), upgraded electrical panel, new mini-split system (unit B 2026), and new water heater (unit B 2026). Excellent opportunity for investors seeking an income-producing property with existing tenant in place.

108 Little Kidwell Ave, Centreville

Listing courtesy of Haven Firm. Contact: 2402457276

$610,000

Spanning nearly 2,800 sq. ft., this Colonial style home is perfectly nestled on a private 1 acre corner lot in the highly desirable community of Lently Farms. Framed by mature shade trees and beautiful lush landscaping, this property offers peace, privacy, and plenty of outdoor space to enjoy. Relax or entertain on the hardscaped rear patio, perfect for grilling and soaking up the sun and appreciate the convenience of the double entrance paved driveway. Step inside to a welcoming foyer that leads to a spacious main level, featuring a kitchen with breakfast nook and coffee/bar station, adjoining family room with a custom raised hearth wood-burning fireplace, and easy access to the bright four season room. The first floor also offers a formal living room and dining room, private office with separate entrance, laundry/mudroom with utility sink and storage cabinets and a half bath. Upstairs you’ll find four generously sized bedrooms, including a primary suite with walk-in closet and private bath featuring a double vanity. An additional full guest bath includes a tiled shower and double vanity. Don’t miss the versatile bonus space above the garage, ideal for a hobby room, studio, or additional storage. A spacious 2-car insulated garage completes the home. With some TLC and your own personal touches and updates, this home could easily become the home you’ve been searching for. Conveniently located just minutes from historic Centreville, a charming waterfront town known for its courthouse square and town wharf. Enjoy quick access to MD Route 301, the Chesapeake Bay Bridge, outlet shopping, waterfront restaurants, marinas, and an easy commute to Easton, Annapolis, and the MD/DE beaches. Experience all the Eastern Shore has to offer—fishing, crabbing, parks, bike and walking trails, farmers markets and so much more! Motivated Seller!!

122 Lently Farm Ln, Centreville

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

$240,000

Estate Sale Opportunity in Grasonville, MD! 3 Bedrooms |2 Full Bathrooms | Private Well & Public Septic . SOLD AS-IS, SELLER WILL MAKE NO REPAIRS. Don't miss this opportunity to purchase a single-family home tucked away on a quiet street in sought-after Grasonville, Queen Anne's County. This home sits on a spacious flat lot and has a detached 2 car garage. Buyer is responsible for all due diligence. Home will require major renovation to the floor structure of the home to include among other things floor joist, bandboard and sub flooring. !!! Inspection recommended !!!! Inspection for informational purposes Only. THERE ARE TWO SPOTS IN THE HOME THAT ARE MARKED WHERE THE FLOOR IS REALLY WEAK. BE EXTRA CAREFUL IN THOSE AREAS. ( LIVING ROOM AND BACK BEDROOM) Home is located in a quiet neighborhood with easy access to major highways, waterfront restaurants, public docks, and just a short drive to the Bay Bridge. Great opportunity to put your own vision and sweat equity in creating the home of your dreams or Great opportunity for a fix and flip or rental income generating property in a desirable area of Queen Anne's County.

106 Fischer Rd, Grasonville

Listing courtesy of Save 6, Incorporated. Contact:

$624,900

Welcome to 420 Five Farms Drive in the sought-after Queen Anne Colony community on Kent Island, where the Chesapeake Bay lifestyle is right outside your door. Nestled in a water-oriented neighborhood featuring a community marina, waterfront park, and endless opportunities to enjoy boating, fishing, kayaking, and stunning sunsets, this home offers the perfect blend of coastal living and modern updates. From the moment you arrive, you’ll appreciate the peace of mind that comes with a brand-new roof and brand-new siding, creating incredible curb appeal and low-maintenance living. Inside, you’ll find a light-filled, airy interior accented by beautiful hardwood floors and a stunning renovated kitchen that serves as the heart of the home. Designed for both everyday living and entertaining, the kitchen flows seamlessly into the main living spaces while offering stylish finishes and ample workspace. The home features three spacious bedrooms and beautifully updated bathrooms, providing comfort and functionality for family and guests alike. Step outside to your private backyard retreat where summer memories are waiting to be made. Relax with your morning coffee in the screened porch, host gatherings around the in-ground pool, or enjoy the privacy and security of the fully fenced backyard. Whether you’re looking for a full-time residence or the ultimate Kent Island getaway, 420 Five Farms Drive delivers the lifestyle buyers dream about, updated, move-in ready, and located in one of Stevensville’s most desirable waterfront communities. Brand-new roof. Brand-new siding. Gorgeous kitchen. Inground pool. Marina community. Chesapeake Bay lifestyle. This is the one you’ve been waiting for.

420 Five Farms Dr, Stevensville

Listing courtesy of RE/MAX Executive. Contact: 4432741900

$1,199,000

5 Beds ⋅ 4 Baths

Sellers have identified their home of choice. A rare opportunity to own one of the largest and most beautiful homes in Gibson's Grant! Welcome to this exceptional coastal retreat in the sought-after community of Gibson’s Grant on Kent Island, offering expansive views of the community pond and Macum Creek. Blending timeless architectural details with modern updates, this beautifully appointed home delivers luxury waterfront living in one of Kent Island’s most desirable neighborhoods. At the heart of the home, the open-concept living and kitchen spaces are thoughtfully designed for both everyday living and entertaining. The light-filled gourmet kitchen features an oversized center island with ample seating, custom built-in banquette dining with additional storage, stainless steel appliances, and seamless flow into the spacious family room. A striking coffered ceiling and extensive custom built-in cabinetry add warmth, character, and functionality to the main living area. The main-level primary suite offers newly installed engineered hardwood flooring, elegant French doors, and sweeping views of the water and expansive backyard. Throughout the home, fresh interior paint, plantation shutters, and custom window treatments create a clean and refined aesthetic. The second level features generously sized bedrooms along with a large bonus living area perfect for recreation, media space, or additional lounge seating. Step outside onto the covered upper-level porch to enjoy peaceful elevated water views. Above the garage, a private apartment with full bath provides exceptional flexibility as a fifth bedroom, guest suite, or home office and is equipped with two new high-efficiency mini-split systems for personalized comfort. Outdoor living is equally impressive with a spacious rear deck overlooking the fully fenced backyard, professionally manicured landscaping, and protected natural surroundings. A wide driveway offers ample parking, a rare feature within Gibson’s Grant. Ideally situated on a quiet street just steps from the scenic Cross Island Trail, residents enjoy access to resort style community amenities including a pool, fitness center, fishing pier, playground, bocce ball court, kayak launch and storage, clubhouse with fitness center and meeting room, nature trails, and waterfront pavilion and grills. Experience the best of Eastern Shore living in this thoughtfully designed coastal home surrounded by the natural beauty of the Chesapeake Bay. Just a short drive to Route 50, providing easy access to local dining, shopping, and commuter routes to Annapolis, Baltimore, and Washington DC. Schedule your tour today!

108 Carriage Heath, Chester

Listing courtesy of Coldwell Banker Realty. Contact: 4102638686

$435,000

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

106 Bodys Neck Rd, Chester

Listing courtesy of Realty Navigator. Contact: 4106433404

$599,900

Recently Reduced and Ready for Its New Owner! Experience the best of Eastern Shore living at 1024 Avalon Court, where spacious design, natural light, and a peaceful setting come together beautifully. Perfectly positioned on a desirable lot with views of the community pond area and protected woodlands, this exceptional residence offers a wonderful blend of privacy, comfort, and everyday convenience. From the inviting exterior with stone accents and a two car garage to the open interior layout and exceptional outdoor living spaces, this home is designed for easy living and effortless entertaining. Step inside to a welcoming foyer with neutral paint and a bright, airy feel that continues throughout the main level. The thoughtfully designed floor plan offers excellent flexibility with formal living and dining areas, generous open gathering spaces, and seamless flow between rooms. Expansive windows bring in beautiful natural light while framing peaceful rear views, creating a warm and inviting atmosphere throughout the home. The heart of the home is the open concept kitchen and family room area, ideal for both everyday living and entertaining. The kitchen features abundant cabinetry, granite counters, stainless steel appliances, recessed lighting, a center island cooktop, and direct connection to the surrounding living spaces. The spacious family room offers a cozy fireplace and easy access to the private screened porch and large raised concrete patio, two standout features rarely found in this community. Both outdoor spaces overlook the community pond area and protected woodlands, creating a private and peaceful backdrop for relaxing, dining, and entertaining. The home continues with spacious bedrooms, including a large main level owner’s suite with generous closet space and a private bath featuring dual vanities, a soaking tub, and separate shower. This main level suite offers excellent flexibility for multigenerational living, guests, or those seeking everyday convenience. Additional bedrooms on the upper level provide comfortable space for family, guests, home office needs, hobbies, or recreation. Outdoor living is truly a highlight, with multiple areas to enjoy the serene wooded setting. The private screened porch is perfect for morning coffee, quiet evenings, or relaxing without the elements, while the oversized raised concrete patio offers wonderful space for grilling, entertaining, or simply enjoying the peaceful rear views. Additional highlights include flexible living spaces, a heated and air conditioned two car garage with amazing storage, and a peaceful rear setting rarely found in such a convenient location. Ideally positioned with easy access to major commuter routes including Routes 50 and 301, this exceptional residence offers convenient access to Downtown Annapolis, Washington, D.C., Baltimore, Kent Island, the Bay Bridge, Middletown, Dover, NSA, Fort Meade and Dover Air Force Base. Enjoy great local amenities including restaurants, shopping, recreation, and all the lifestyle conveniences that make the Eastern Shore so desirable. Don’t miss out on this incredible opportunity!

1024 Avalon Ct, Stevensville

Listing courtesy of Berkshire Hathaway HomeServices PenFed Realty. Contact:

$795,000

4 Beds ⋅ 4 Baths

This boater's paradise demonstrates the perfect blend of luxury and convenience. The property boasts three floors of sweeping waterfront views all easily accessed via your own private elevator. High end finishes can be found throughout and the home has been impeccably maintained. The first floor feels inviting with the fireplace, open kitchen, and guest bedroom with ensuite full bathroom currently being used as an office. The second floors wows you with 3 spacious bedrooms including the primary that has a walkout balcony for quiet evenings staring out over the water. The top floor provides yet another entertaining or living space with a wet bar, full bathroom, and a walk out balcony. Outdoor living in general is a highlight here with each floor allowing for a different perspective of the Eastern Shore landscape. Don't forget about the amenities of the community. Lounge out by the pool, walk to famous waterfront seafood establishments, or navigate the vast waters of the Chesapeake from your deeded 35 foot deep water boat slip just steps away. This luxury Eastern Shore destination is located just an hour from Washington, D.C. or Baltimore and less than two hours from Philadelphia.

110 Channel Marker Way Unit #203, Grasonville

Listing courtesy of Coldwell Banker Chesapeake Real Estate Company. Contact:

$635,000

Newer construction opportunity, built in 2022, located in the sought-after water-privileged Romancoke on the Bay community, residents enjoy a private community beach and boat launch with sweeping sunset views over the Chesapeake Bay. This thoughtfully designed craftsman-style home offers over 2,700 sqft of living space. Featuring 10’ main living level ceiling height, 9’ ceilings on the bedroom level. The kitchen features quartz countertops, cast iron farmhouse sink, cabinet crown molding, stainless steel appliances, a center island, and ample cabinet space, opening to the spacious living and dining area for everyday living and entertaining. The dining room leads out to a covered porch in the rear. The primary suite is designed as a private retreat with a spacious bedroom, walk-in closet, and ensuite bath featuring an oversized double vanity and shower. Three additional bedrooms provide flexibility for guests, family, or a home office. Other highlights include a laundry room on the bedroom level, hidden walk in pantry and office area off of the kitchen, mud room leading from garage, generous storage, a flex room on each living level that could be converted into additional bedrooms. Other upgrades to note poured concrete slab in the crawlspace, solid pine interior doors and trim, separate HVAC systems for each living level, oversized concrete driveway poured 5” thick with extra rebar and an attached 2-car garage. Too many upgrades to list! Situated on an open and spacious fenced in lot.

201 Ackerman Dr, Stevensville

Listing courtesy of Mr. Lister Realty. Contact: (410) 486-5478

$505,000

2 Beds ⋅ 3 Baths

Welcome to effortless luxury in this beautifully maintained move-in-ready home located within a highly desirable 55+ resort-style community. From the moment you step inside, the high ceilings and custom architectural details elevate the entire space creating an atmosphere of refined elegance. The beautiful thoughtful layout maximizes comfort and convenience, allowing you to live effortlessly. Gleaming hardwood floors flow seamlessly through the main living areas, which feature two spacious bedrooms and two-and-a-half pristine bathrooms. Enjoy access to top tier community amenities while relaxing in a home crafted with unmatched care and quality. Recent care: Roof-late 2022, water heater replaced 2025; heat pump replaced 2022; updated appliances, coated garage flooring; gutter guard, finished sky basement. The Symphony Village community is well established, with mature trees throughout, and an impressive clubhouse with many amenities, including a concert hall for the many events organized by the various committees. The main gathering area is bright and welcoming, and is the location for semi-monthly social hours where you bring a dish to share and get to meet your neighbors. Several groups with varied interests meet in the clubhouse on a regular basis, and you might walk through the clubhouse and see folks learning to paint in the craft room, others playing pool, some playing mahjong in the concert hall, or committee meetings to keep things humming along. You can walk outside to the covered patio area and the pool beyond, where residents enjoy holiday picnics, quiet evening time, and fun with the kids during the day. The indoor pool is open every day from early morning until late at night, and you can show up for water aerobics every weekday morning at 9:00A.M. Currently there are Spanish classes offered, in addition to soul line dancing, and at any time you can learn how to play bridge or hand and foot, so there is plenty to keep everyone busy. However, there is no requirement to participate in any activities, and you can live a quiet life in Symphony Village enjoying retirement or still working. There are many areas to walk in around the neighborhood, and in the clubhouse grounds is a pergola to sit and watch the world go by, a kids' playground, a picnic area, bocce, a putting green (and active league) and a trail leading to Dunkin' Donuts and the shopping center just minutes away.

204 Overture Way, Centreville

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

$675,000

High End & High Efficiency! Sustainable living meets timeless craftsmanship in this incredible custom-built Nexus home. If you’ve been dreaming of a property that blends luxury, efficiency, privacy, and intentional design… this is it. Situated on an acre with NO HOA, this craftsman-style beauty was thoughtfully designed for both comfort and energy efficiency with features rarely found together in one home: Owned Solar Panels Brand New Geothermal Heating System Electric Vehicle Charging Plug-Ins Hardiboard Plank Siding for durability and timeless curb appeal Inside, the details shine: ✨ Beautiful custom moldings ✨ Updated kitchen with high-end appliances & countertops ✨ Warm, elevated finishes throughout ✨ Spaces that feel both elegant and grounded Outside is where this home truly becomes a lifestyle: 🌿 Covered porches for slow mornings and evening unwinds 🔥 Hardscaped patios perfect for entertaining ⚽️ Wide open green space for gardening, soccer games, pets, or simply breathing a little deeper An almost net-zero home with privacy, style, and functionality like this is incredibly rare.

103 Beech Tree Ln, Centreville

Listing courtesy of Samson Properties. Contact: 7033788810

$1,470,000

5 Beds ⋅ 5 Baths

Waterfront living with lifestyle, location and luxury! Located at the mouth of the Chester River, this home is in the perfect spot for days on the Bay, boat rides to Kent Narrows restaurants, golf at Queenstown and shopping the Outlets. Just minutes from the Bay Bridge, this beautifully updated home delivers the best of Eastern Shore living with 259' waterfront, community pier, good schools and easy access to Annapolis and beyond. The deeded slip (with boat and PWC lifts) makes life on the water a breeze, while the waterfront backyard soaks up the sun and wildlife on Winchester Creek. This beautiful home features more than 4,400 square feet on three finished levels with west-facing water views from expansive windows that fill the home with natural light. The two-story family room features a rebuilt luxury fireplace with custom trim work, creating an everyday space that is upscale yet comfortable. The renovated gourmet kitchen offers quartz countertops, heated floors, stainless steel appliances, abundant cabinetry, a breakfast nook, and a redesigned island perfect for gathering with family and friends. The first floor also boasts a two-story foyer, formal dining room, and a comfortable living room/study complete with large windows and a 2nd fireplace. Hardwood floors, custom millwork, fresh paint and designer finishes create a timeless coastal feel thoughout. Enjoy beautiful water views from the main-level primary suite that features California Closets, a beautifully remodeled spa-inspired bath and a cozy bay window sitting area. The second waterfront ensuite provides ideal accommodations for guests, extended family or single-floor living. The second level features three additional bedrooms and a versatile bonus room ideal for a home office, homework or as a second family room. The third level is designed for entertaining, complete with a wet bar, beverage cooler, full bath and surround sound. It's perfect for game days, movie nights, or extended-stay guests. Set on more than 1.37 acres, the property offers privacy, an expansive lawn, updated landscaping, abundant wildlife and sweeping water views. Enjoy morning coffee as the sun rises over the water and glowing sunsets from the new TimberTech deck and covered porch. The slip at Homeport's 4MLW private pier is almost next-door for an early morning ride or sunset cruise. Whether hosting family and friends, raising children, enjoying pets in the backyard or unwinding by the water after a day on the boat, this setting is thoughtfully designed for comfort and ease. Extensive recent improvements in the dedicated utility room include dual Bosch high-efficiency HVAC systems (2023 and 2024), a Rinnai tankless water heater and a whole-house smart water treatment and management system. The home also features smart thermostats on each floor, ceiling fans throughout, a Vector security system, invisible pet fence, professional landscaping, nearly all new lighting inside & out, updated bathrooms and more. Enjoy Chesapeake living with easy access to Annapolis and the Bay Bridge.

109 Starboard Ct, Grasonville

Listing courtesy of Northrop Realty. Contact: 4105310321

$699,900

Wonderful opportunity awaits on the sandy beaches of the Chesapeake Bay. Bring your vision and dreams to this three-bedroom rancher in need of major updates located on the southern shores of Kent Island. This home is ready for your vision of a salty life on the Bay. Conveniently located about 15 minutes from the Bay Bridge in the popular neighborhood of Tower Gardens. The expansive lot provides ample room for possible renovation and expansion of the home's current footprint. Sandy beach area with plenty of room for installation of a private pier or use the community's private boat ramp. Attached 2 car garage with large parking pads. Fenced in yard for privacy. Public Sewer installed in 2022 allows for the immediate addition of bedrooms and bathrooms for the new owners. Home is ready for quick settlement and investors are welcome!

400 Beachside Dr, Stevensville

Listing courtesy of ExecuHome Realty. Contact: 4436323000

$548,000

NOE: THIS HOME OFFERS OVER 3,630 Sq Ft of Finished Space including the Professionally Finished dWalkout Basement! This stunning home as been refreshed and is ready to be your retreat from the fast lane of life! You won’t find a home at Symphony Village with more desirable features than this spacious home backing to acres of preserved woodlands and paved walking trails. Come through the front door into the foyer... Step into a huge great room offering flexible living /dining/ entertaining space, a beautiful kitchen with breakfast bar that opens to a Morning room with cathedral ceilings and a grand arched palladian window overlooking the woods. You will enjoy relaxing in the spacious family room featuring a gas fireplace or step out to the fully finished 3-Season room and just enjoy watching nature bloom before your eyes. Also on the main level, you will find the primary bedroom with "His & Hers" walk-in closets and a spacious private bath with soaking tub and a walk-in shower as well as a 2nd Bedroom bedroom with another full bath. A large mud room/laundry room is conveniently located just inside entry from the garage. Only a relatively small number of homes in Symphony Village offer a full basement...this one offers a FULLY FINISHED FULL BASEMENT with a walkout exit to the private rear yard, and a custom Patio backing to acres of wooded open space and walk/jogging paths. The lower level includes a third bedroom, full bath, a hobby room, utility room PLUS an enormous Flex Room that is the perfect finished space for your theatre room, billiard room, party room, playroom or even your own ,private gym!Are you looking for plenty of storage? The "Sky Basement" on the upper floor provides plenty of additional storage and is also nicely finished. Oversized 2 car garage. This home is one of only a small number of homes featuring a full finished walk out basement! Symphony Village in Centreville, Maryland is a popular 55+ active adult community known for its clubhouse, indoor & outdoor pools, tennis/pickle ball courts, walking paths, fitness center, party room, beautiful community bar for gathering with friends and other social amenities. Come take a tour and you'll find your home!

107 Overture Way, Centreville

Listing courtesy of Chaney Homes, LLC. Contact: (410) 739-0242

$840,000

4 Beds ⋅ 4 Baths

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

232 Evelyne St, Chester

Listing courtesy of TTR Sotheby's International Realty. Contact: 4106733344

$875,000

Much loved home sited on 1.03 acres offering sunset views over the water on one side and golf course views on the other. This spacious home features quality 2x6 construction, hardwood flooring, and Andersen windows that provide abundant natural light throughout. The kitchen measures approximately 19’ x 14’ and includes maple cabinetry, a center island, table space, and an open layout connecting directly to the family room. The family room features a fireplace with an efficient wood-burning insert and a wall mounted 77 inch LG OLED TV, about one year old. Separate living and dining rooms, both with bow windows, frame the beautiful water views. The main-level fourth bedroom includes built-in shelving and currently serves as a home office. The gracious primary suite features water views from a bow window, a large bath, and huge walk-in closet. Two additional good sized bedrooms and a full bath complete the upper level. The oversized two-car garage offers approximately 600 square feet with workshop space, pegboard walls, and extensive shelving. The blacktop driveway includes a large parking pad with room for up to six vehicles. Outdoor features include a screened porch overlooking the golf course and a 16’ x 12’ Amish-built shed designed to complement the home, complete with interior shelving. Additional features include a walk-in attic with shelving and extensive storage space, recently upgraded lighting, a built-in ironing board in the laundry area, and a Bruno stairlift on the wide staircase between the first and second floors, which can be removed if desired. Recent upgrades include new washer, dryer, refrigerator, microwave, dishwasher, and Trane heat pumps that are less than two years old. Located in the waterfront community of Prospect Bay, offering resort-style amenities—including golf, a swimming pool, boat ramp, tennis courts and a clubhouse with restaurant.

108 Prospect Bay Dr W, Grasonville

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

$1,100,000

Welcome to this pristine contemporary ranch in the coveted waterfront community of South Wind on Kent Island, where luxury, comfort, and resort-style living come together on 1.21 beautifully landscaped acres. From the moment you arrive, the home’s lush green lawn, vibrant gardens, and custom walkways create a picture-perfect setting worthy of a magazine cover. Inside, the open-concept floor plan is filled with natural light and highlighted by gleaming hardwood floors and exceptional upgrades throughout this 4 bedroom, 3 full bath estate. The stunning designer kitchen is truly the heart of the home, featuring crisp white cabinetry, granite countertops, an oversized center island, a premium Wolf 5-burner gas cooktop flanked by custom spice cabinets, a wall convection oven, and built-in microwave...crafted for both everyday living and effortless entertaining. Just beyond the main living areas, the inviting three-season sun porch with white tile flooring overlooks your own private backyard retreat. Step outside onto the expansive maintenance-free decking and new patio surrounding the spectacular heated gunite pool, complete with a waterfall feature and dual stair entrances, creating the ultimate outdoor oasis. The professionally designed landscaping continues throughout the property, accented with colorful plantings, mature greenery, and thoughtfully designed outdoor spaces. A custom-built shed, designed to perfectly complement the home, offers electric service and a gated outdoor storage area. Additional premium features include an oversized two-car garage with air conditioning, two-zone gas heat and central air, a whole-house generator, tankless water heater, updated crawlspace with dehumidifier, and energy-saving foil-wrapped attic insulation. The roof is only two years young, offering peace of mind for years to come. Perfectly positioned to capture serene open-space and water views, this exceptional property also includes access to South Wind’s sought-after amenities, including a community beach, boat ramp, pier, tennis courts, dry dock, and more. This is more than a home...it’s a private Kent Island retreat designed for exceptional living.

2812 Harvest Ct, Chester

Listing courtesy of RE/MAX Executive. Contact: 4432741900

$700,000

2 Beds ⋅ 3 Baths

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

132 Wheelhouse Way Unit #11, Chester

Listing courtesy of Real Broker, LLC. Contact: 8504500442

$649,500

4 Beds ⋅ 2 Baths

Discover the exceptional craftsmanship of Lomaxx Custom Homes with this thoughtfully designed modern farmhouse rancher! This to-be-built home offers 4 spacious bedrooms, 2 full bathrooms, and an inviting open-concept floor plan perfect for everyday living and entertaining. Unlike many new construction homes, this property comes loaded with premium upgrades already included—without the hefty upgrade costs! Standard features include a fully encapsulated and conditioned crawl space, luxury vinyl plank flooring throughout, custom trim work and built-ins, stunning faux wood beams, black windows, stainless steel appliances, quartz countertops, and high-end finishes that truly set this home apart. Situated on just over 2 acres, there’s plenty of room for whatever hobbies, recreation, or outdoor lifestyle you can imagine. The breathtaking rural views create the perfect peaceful setting while still offering convenient access to nearby destinations—approximately 5 minutes to the Town of Centreville, 20 minutes to the Bay Bridge, and just 30 minutes to Middletown, Delaware. The lot offers a beautiful natural slope away from the homesite, adding to both the setting and functionality of the property. Enjoy peaceful mornings on the covered front porch and unwind in the evenings on the rear patio while taking in the surrounding countryside. The bright and airy living spaces are complemented by a stunning kitchen and a private owner’s suite designed for comfort and relaxation. Additional floor plans and layouts are also available and can be discussed to fit your needs and vision. The builder is also open to constructing a pole barn for an additional cost, creating endless possibilities for storage, hobbies, workshop space, or recreational use. Photos shown are of a previously built model.

Price Station Rd, Centreville

Listing courtesy of CR Realty. Contact: 4104900460

$575,000

Discover the exceptional craftsmanship of Lomaxx Custom Homes with this thoughtfully designed modern farmhouse rancher! This to-be-built home offers 3 spacious bedrooms, 2 full bathrooms, and an inviting open-concept floor plan perfect for everyday living and entertaining. Unlike many new construction homes, this property comes loaded with premium upgrades already included—without the hefty upgrade costs! Standard features include a fully encapsulated and conditioned crawl space, luxury vinyl plank flooring throughout, custom trim work and built-ins, stunning faux wood beams, black windows, stainless steel appliances, quartz countertops, and high-end finishes that truly set this home apart. Situated on just over 2 acres, there’s plenty of room for whatever hobbies, recreation, or outdoor lifestyle you can imagine. The breathtaking rural views create the perfect peaceful setting while still offering convenient access to nearby destinations—approximately 5 minutes to the Town of Centreville, 20 minutes to the Bay Bridge, and just 30 minutes to Middletown, Delaware. Enjoy peaceful mornings on the covered front porch and unwind in the evenings on the back deck while taking in the surrounding countryside. The bright and airy living spaces are complemented by a stunning kitchen and a private owner’s suite designed for comfort and relaxation. Additional floor plans and layouts are also available and can be discussed to fit your needs and vision. The builder is also open to constructing a pole barn for an additional cost, which would fit perfectly on the right side of the property beyond the hedge row and ditch. A culvert is being installed by the builder to provide easy access to this area, creating endless possibilities for storage, hobbies, workshop space, or recreational use. Photos shown are of a previously built model.

Clark Corner Rd, Centreville

Listing courtesy of CR Realty. Contact: 4104900460

$679,900

Welcome to Meadow Creek. Estate homes on acre plus homesites with plenty of room for a pool and a separate garage.. In the country but close to downtown Centreville. Centreville offers restaurants, grocery stores, parks and schools. This one level home features a formal dining area flanked by columns as well as three nicely sized bedrooms and a large living area with gourmet-appointed island kitchen, breakfast room and optional morning room on one level. Your owner’s bath includes a separate soaking tub and shower or you may choose to install the large enclosed spa shower and closet for linens. Plan features a main level washer/dryer laundry/mud room and a lower level which can be customized to meet your needs. **Special offer Construction financing** Models shown with options

319 Twin Meadows Farm Ln, Centreville

Listing courtesy of Keller Williams Flagship. Contact:

$787,000

Searching for a property that truly stands out? This fully upgraded custom designed home offers the perfect blend of luxury and privacy. From the moment you turn onto the driveway, you'll already be in love! Greeted by a long gravel driveway, oversized parking area and breathtaking curb appeal that only gets better as you head to your grand entrance front covered porch. Set on a large lot with thoughtfully planted trees for future privacy, rows of whimsical wildflowers, scenic farmland views and extensive landscaping, the setting feels both peaceful and refined. Inside, the wide open floorplan is anchored by a stunning gas fireplace that creates a warm focal point for the main living space, while the oversized kitchen island is perfect for everyday dining or weekend entertaining. A butler’s pantry provides exceptional storage for appliances and kitchen essentials, and the luxurious primary suite features an elevated bathroom and enormous walk in closet that conveniently wraps around to the main level laundry room. Just beyond the main living area, the attached three seasons room showcases floor to ceiling glass views, creating the perfect space to enjoy the Eastern Shore of Maryland’s changing seasons in year round comfort. Downstairs, the unfinished basement with a walk out staircase offers endless potential for future living space, recreation or storage, while the detached building with its own electric meter, concrete pad and covered lean to adds incredible flexibility for hobbies, equipment or workshop space.

117 Woodfield Ct, Centreville

Listing courtesy of RE/MAX Executive. Contact: 4432741900

$569,900

New Home to be built! Spacious rancher on an oversized lot. Act now to pick your colors! Call today for more information!

Baltimore Rd, Stevensville

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

$180,000

Don’t settle for less! If you’ve been searching for space, country living, and freedom from HOA restrictions — all while maintaining convenient access to major routes — this property deserves your attention. Situated on 9+ acres just approximately 3 miles from Rt. 301 in the quaint Town of Barclay, the possibilities here are endless. Partly wooded and rich with mature landscaping, this beautiful property features a charming small stream and offers the perfect setting to build your dream family home. ***Public sewer access is now available and at site for this property. You will just need to connect to your home when ready! As per QAC Director of Public Works, the "pump shell" is already installed on the property and the actual pump is ready to be installed when necessary. NO allocation fee is necessary for a single home on this property*** Current Sewer Service Fee is $73/mo. Looking for less acreage? This parcel may offer subdivision potential, subject to buyer due diligence. An existing trailer remains on the property and is uninhabitable — please do not enter. Trailer to be removed soon!

1420 Barclay Rd, Barclay

Listing courtesy of Benson & Mangold, LLC. Contact: (443) 988-0483

$649,999

Welcome to the lifestyle you’ve worked so hard for in the sought-after 55+ community of Bay Bridge Cove. This stunning end-unit home offers over 2,300 square feet of upgraded living space designed for comfort, convenience, and enjoying every moment of this next chapter. From the moment you walk in, you’ll love the wide-open floor plan, beautiful LVP flooring, and the natural light that fills the home. The heart of the home is the gorgeous kitchen and living space, perfectly designed for entertaining or relaxing at home. The kitchen features stunning quartz countertops, a large center island, high-end appliances, and an abundance of cabinet space, all flowing seamlessly into the dining area and cozy living room with a fireplace. The main level offers the ease of two spacious bedrooms, each with its own full bathroom. The primary suite feels like a private retreat with a sitting area, oversized walk-in closet, and a luxurious bathroom featuring double vanities, floor-to-ceiling tiled shower, and glass doors. Bedroom two is equally impressive with its own beautifully tiled stand-up shower and glass doors. Upstairs offers incredible flexibility with a large bonus living space perfect for a family room, office, gym, hobby area, or guest retreat, along with a third bedroom and full bathroom with a shower/tub combo. Step outside and unwind in the relaxing screened-in porch or separate deck, all overlooking mature trees that provide exceptional privacy and peaceful views. Bay Bridge Cove offers more than just a home, it’s a lifestyle. Enjoy resort-style amenities including a clubhouse, pool, tennis courts, bocce ball, dog park, and a full calendar of community events and activities designed to keep you as active and social as you’d like to be. This is your opportunity to finally experience the lifestyle you’ve earned.

364 Moorings Cir Unit #100, Stevensville

Listing courtesy of RE/MAX Executive. Contact: 4432741900

$150,000

Zoned for commercial/residential, public sewer, no water currently availability. Trailer is not livable. Great opportunity to build your new home in the heart of Grasonville and on 1/2 acre lot with lots of mature trees.

110 James Ln, Grasonville

Listing courtesy of Wilson Realty & Staging LLC. Contact: 4103042250

$384,900

Experience Eastern Shore living at its finest in this oversized end‑unit townhome offering beautiful water views, multiple composite decks, and a community that has recently upgraded its siding, roofing, and more. Inside, the main level features hardwood floors, recessed lighting, a fireplace, an updated full bath, and a main‑level bedroom, along with a spacious kitchen and dining area and a conveniently located laundry room. A brand‑new heat pump system adds comfort and efficiency. Upstairs, the primary suite boasts a private balcony, large ensuite bath, and generous closet space, while the secondary bedroom includes its own full bath. Just 3 minutes to the Bay Bridge, 20 minutes to Annapolis, and 45 minutes to D.C., this home is ideal for a weekend retreat or full‑time living. Condo amenities include a pool, clubhouse, lawn care, waterside path, snow removal, and trash/recycling. Enjoy kayaking, paddleboarding, boating, or simply taking in the water views, all within walking distance of restaurants, shops, a winery, pet store, post office, and more.

1301 Marion Quimby Dr, Stevensville

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

$364,900

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

5011 Bridgepointe Dr, Chester

Listing courtesy of Keller Williams Realty Centre. Contact: 4103120000

$357,900

Low maintenance island living at its best! 6005 Bridgepointe Dr is freshly painted, deep cleaned, and ready for its new owners! All appliances new within the last two years, power washed & fresh paint on the deck with beautiful views of the pond. Easy access to RT50 - perfect for the commuter. Quiet neighborhood.

6005 Bridgepointe Dr, Chester

Listing courtesy of Rosendale Realty. Contact: 4107580333

$216,000

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

108 Price Rd, Chester

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

$950,000

5 Beds ⋅ 5 Baths

WOW! This one is an absolute 11 on a scale of 1–10! Thoughtfully updated with stylish, on-trend finishes throughout, this property is truly exceptional from top to bottom. From the moment you step onto the covered front porch and into the dramatic two-story foyer, you’ll feel the difference. A private dining room sits to one side while two spacious main-level offices on the other make balancing work and home life effortless. And YES—high-speed internet is available through Talkie Fiber! At the heart of the home is a bright and beautiful gourmet kitchen featuring stainless steel appliances, a full refrigerator and full freezer, center island seating, and the kind of layout that naturally becomes the gathering place for everyone. The adjoining living room is warm and inviting, anchored by a fireplace and framed by oversized windows that flood the space with natural light while overlooking the picturesque backyard. Upstairs, you’ll find a magazine-worthy laundry room along with three spacious bedrooms and two beautifully updated full baths. The primary suite was designed to feel like a true personal retreat—complete with vaulted ceilings, a private deck overlooking the grounds, and plenty of natural light. Start your mornings with coffee in the fresh air or unwind at the end of the day under the stars. The luxurious ensuite bath features a soaking tub, separate shower, double vanity, and soaring ceilings that make the space feel spa-like. And just when you think it can’t get any better… there’s approximately 1,800 additional square feet of finished living space in the lower level! Complete with a private movie theater with seating for eight, bedroom, full bath, family room, kitchenette, and private entrance, the lower level offers incredible flexibility for guests, multi-generational living, or an in-law suite. Situated on nearly 1.5 acres surrounded by mature trees, this property offers the peaceful privacy of your own backyard oasis. The in-ground pool with landscaping, fire pit, multiple lounging areas, and glowing string lights create the perfect setting for entertaining family and friends all summer long. And tucked beyond it all? A beach volleyball court and horseshoe pit that make this property feel like your own private resort. PLUS: (As if all that wasn't enough) There is a whole house Generac to ensure you never lose power AND a 46,000 Enphase Solar (owned--no lease takeover!!) that saves BIG on electric and also returns Solar Renewable Energy Credits (SREC). Brand New Roof, too! Sound too good to be true? It’s not… unless you wait too long. This GEM is guaranteed to turn heads the moment it hits the market—so be ready!

218 Upland Ln, Centreville

Listing courtesy of Wilson Realty & Staging LLC. Contact: 4103042250

$3,000,000

Stevensville - 4 Buildings zoned SHVC on 1.32 acres of investment property. 2 buildings are residential with tenants and a total of 6 apartments. The third building has one residential apartment and a retail space on first floor. The multi-functional office space is about 15,000 sq ft. The two-story main building has and elevator that is currently used as a daycare/school. There is some available space for rent on the first floor that is currently set up as a spa. Large rear parking lot and in the center of the historic Stevensville.

104 E Main St, Stevensville

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

$670,000

Friday July 24th all day open house 10-7. Welcome home to this Colonial-style home located in the highly sought-after Claiborne Fields in Centreville, MD! Featuring 4 bedrooms and 3 bathrooms, 2 car garage, this exceptional property offers timeless charm, quality construction, and space to grow. From the moment you arrive, the outstanding landscaping and curb appeal make a lasting impression. Inside, you’ll find original hardwood floors throughout, a spacious layout, and attention to detail that truly sets this home apart. The sunroom and patio with a permanent umbrella overlook breathtaking views of fields, mature trees and the peaceful pond, creating the perfect setting for relaxing mornings, entertaining guests, or enjoying nature year-round. Additional highlights include an encapsulated crawl space, new roof, newer heat pumps and furnace all in the past 4 years, granite countertops, Anderson 400 series windows, hot water Rinnai tankless, water treatment system, numerous upgrades throughout, and craftsmanship that must be seen to be appreciated. No detail was missed in the construction quality of this home — you’ll need to read the extensive upgrade list to believe it! Located in a friendly, established neighborhood with convenient access to local amenities, schools, parks, and everything Centreville has to offer. This one is truly special — see the video!

306 Old Line Dr, Centreville

Listing courtesy of Taylor Properties. Contact:

$300,000

Enjoy the opportunity to own a mostly cleared parcel in the heart of Queen Anne’s County, just minutes from downtown Centreville. This mostly cleared lot offers a great opportunity for buyers looking for privacy, open space, and convenient access to town while still enjoying a peaceful country setting. Located just minutes from historic downtown Centreville, you’ll enjoy easy access to local restaurants, shopping, schools, parks, and Route 301 for commuting. The property has not been perc tested within the last 20 years, giving buyers the opportunity to explore future possibilities and improvements to suit their vision. With much of the clearing already completed, this parcel provides an excellent head start for a future homesite, weekend retreat, or long-term investment. Enjoy everything Queen Anne’s County has to offer including boating, fishing, waterfront dining, and the laid-back Eastern Shore lifestyle — all while remaining conveniently close to Centreville and an easy drive to the Bay Bridge.

Damsontown Rd, Queen Anne

Listing courtesy of Eastern Shore Real Estate, LLC. Contact: 4103042011

$620,000

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

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

$499,900

Brand new home ALMOST COMPLETE in Chesapeake Estates! Shorter drive to Route 50 than most other new construction in Stevensville. House is well appointed with LVP throughout the 1st floor and bathrooms, quartz countertops, full kitchen appliance suite, white shaker cabinets, large window at the kitchen sink, front porch, and more. The home is located on a very quiet, private street with minimal traffic. Energy efficient new home for low maintenance and low energy bills. Can close in 30 days or less!

111 Chestnut Rd, Stevensville

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

$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

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