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205 Anchor Ln, Chester
$500,000
4 Beds ⋅ 3 Baths
SPACE, FLEXIBILITY & VALUE ON KENT ISLAND! Welcome to 205 Anchor Lane, where generous square footage, versatile two-level living and incredible outdoor space come together to create a home that can truly adapt to your needs. With 5 bedrooms, updated bathrooms and living spaces on both levels, the floor plan offers excellent flexibility for multi-generational living, guests, a home office or the potential to create a private in-law suite. The main level features easy-care LVP flooring, while the lower level has been refreshed with brand-new carpet, giving the home a fresh, move-in-ready feel. Multiple living and gathering spaces mean there is room to spread out without sacrificing connection. Outside, the possibilities continue! Enjoy morning coffee on the screened porch, entertain on the spacious deck, or take advantage of the large backyard for play, pets, gardening and gatherings. Car enthusiasts, hobbyists and anyone needing serious storage will LOVE the impressive detached 4-car garage—an increasingly hard-to-find feature on Kent Island. And the best part? NO HOA! Enjoy the freedom to make the property your own without the added monthly community expense. With 5 bedrooms, two levels of flexible living space, updated baths, multiple outdoor living areas, a huge backyard and an exceptional 4-car detached garage, 205 Anchor Lane delivers an incredible amount of home and versatility for the money. If you've been searching for true VALUE on Kent Island, this one deserves a look! With 5 bedrooms and 3 full bathrooms, this home provides room for everyone. The lower level offers excellent potential for multigenerational living, guest accommodations, or a future in-law suite. Fresh carpet, luxury vinyl plank flooring, and updated bathrooms create a move-in ready feel while still leaving opportunities to add your own personal touches and build equity. The functional floor plan offers multiple living spaces, a two-car garage, and abundant storage throughout. Outside, the expansive yard provides plenty of room for entertaining, gardening, pets, or simply enjoying the outdoors. Ideally located within walking distance to local dining, Castle Marina, and the Cross Island Trail, you'll love the convenience of enjoying the Kent Island lifestyle right from your doorstep. Public sewer service and well water add to the property's appeal. Whether you're searching for extra space, a home that can accommodate extended family, or simply a great value in a sought-after location, 205 Anchor Lane delivers endless possibilities.

205 Anchor Ln, Chester

Listing courtesy of Samson Properties. Contact:

114 Bayview, Grasonville
$499,000
3 Beds ⋅ 4 Baths
Open Saturday 10am-12pm! WOW! Reduced over $40,000 - Welcome to 114 Bayview—where your boat days get a serious upgrade. This home includes a private boat slip in the community marina with direct access to Kent Narrows, putting you just a 30-minute ride to St. Michaels, Rock Hall, or Cambridge. If you’ve been dreaming about pulling up to waterfront restaurants or spending full days on the water… this is your launch point. Back at home, enjoy front-row views of the 4th of July fireworks, all without leaving your property. Inside, this home is completely turn-key with LVP flooring, fresh paint, and an updated primary bath. Each bedroom features its own private bath, making it ideal for guests, roommates, or weekend hosting. The garage offers the storage every boater needs—perfect for kayaks, paddleboards, bikes, and all your gear. Even better? This home can be sold furnished, making it a true move-in-ready or weekend getaway opportunity. All of this—boat slip, water access, views, updates, garage, and flexibility—offered at just $509,000. If you’ve been waiting for an easy, low-maintenance way to live the Eastern Shore boating lifestyle… this is it.

114 Bayview, Grasonville

Listing courtesy of Samson Properties. Contact:

2011 Stevens Dr, Chester
$489,900
3 Beds ⋅ 2 Baths
Welcome to 2011 Stevens Drive — a completely renovated home offering exceptional one-level living with a spacious, open floor plan and a long list of thoughtful upgrades throughout. From top to bottom, this home has been transformed with modern finishes, new flooring, fresh paint, updated lighting, renovated bathrooms, and a beautifully redesigned kitchen. The oversized kitchen features quartz countertops, updated appliances, abundant cabinetry, and plenty of workspace, with a large laundry room conveniently located just off the kitchen. Just off the kitchen, a beautifully appointed private dining room provides an elegant space for entertaining and hosting gatherings. With its versatility, this room could also serve as a sophisticated home office, library, or additional flex space to suit your lifestyle. The expansive living room is truly a showstopper, featuring dramatic 30-foot ceilings, recessed lighting, a fireplace, and an open, airy feel that makes the space perfect for both everyday living and entertaining. New LVP flooring flows throughout the entire home, complemented by all-new lighting fixtures and fresh paint throughout. The spacious primary suite offers a private retreat with a walk-in closet, a beautifully updated bathroom with a double quartz vanity, and a rare feature — direct access to the rear deck. Step outside from the primary suite and enjoy views overlooking the peaceful, wooded rear yard. Two additional bedrooms provide plenty of flexibility, including an oversized bedroom with its own walk-in closet. Both bathrooms have been completely updated with new vanities and quartz countertops. Additional improvements include a brand-new roof with a 30-year warranty, an oversized two-car attached garage, abundant storage, and thoughtful updates throughout. With its expansive living spaces, impressive ceiling height, renovated kitchen and baths, private wooded setting, and exceptional primary suite, 2011 Stevens Drive delivers refined, turnkey one-level living at its finest.

2011 Stevens Dr, Chester

Listing courtesy of Samson Properties. Contact:

105 State St, Stevensville
$479,500
4 Beds ⋅ 2 Baths
Highest and best due 12pm 10/24/26 With its charming white picket fence, inviting curb appeal, and timeless character, this delightful 4-bedroom, 2-full-bath Cape Cod feels like something straight out of a storybook! Nestled right in town, this home offers the perfect blend of small-town charm and everyday convenience. Enjoy being just a short stroll from local schools, the library, Love Point Park, the dog park, restaurants, coffee shops, the Kent Island Heritage Society, the Kent Island Federation of Arts, and so much more! Imagine morning coffee at your favorite local spot, afternoon walks through town, and enjoying everything this vibrant community has to offer right outside your door. Inside, you'll find a comfortable and versatile floor plan with two bedrooms and a beautifully appointed full bathroom on the main level, featuring a double vanity and walk-in tiled shower. Upstairs, two generously sized bedrooms and another full bathroom provide plenty of space for family, guests, or a home office. Dual-zone HVAC, replaced within the last five years, adds comfort and efficiency. One of the home's most inviting features is the charming sunporch, complete with brick flooring and a propane stove, creating a cozy retreat to enjoy throughout the seasons. Whether you're sipping your morning coffee, curling up with a good book, or watching the seasons change, this space is sure to become a favorite. Outside, the fully enclosed yard, framed by that quintessential white picket fence, completes the fairy-tale setting. A detached two-car garage offers exceptional functionality, including walk-up stairs to additional storage space, while the paved driveway provides plenty of off-street parking. And the practical perks are just as appealing: public water, public sewer, and NO HOA! Full of character, charm, and convenience, 105 State Street is a rare opportunity to enjoy the lifestyle of historic Stevensville with the space and amenities you've been looking for. Offered at $479,500. Come experience the magic of this storybook home for yourself!

105 State St, Stevensville

Listing courtesy of Samson Properties. Contact:

138 Cool Meadow Dr, Centreville
$464,000
4 Beds ⋅ 3 Baths
VA approved short sale at the current list price. Please read agent remarks for more information. Also, please note there is a noticeable smoke odor in the garage, with a lighter residual odor that carries into portions of the home. This home offers the kind of space and flexibility that’s hard to find. With four bedrooms, two and a half baths, and over 4,300 square feet total, there’s room here to spread out, settle in, and make it your own. Just over 2,700 square feet are finished, giving you generous living areas while still leaving plenty of opportunity to customize what comes next. Inside, you’ll find hardwood floors, granite countertops, and stainless steel appliances that bring a clean, timeless feel to the main living spaces. There’s also a flexible room that works well as a home office or creative space and could even function as a small additional bedroom with the use of an armoire. The layout feels practical and comfortable, whether you’re hosting friends or enjoying a quiet night in. The home includes a two car garage and a 120V GFI outlet for electric vehicle charging. Solar panels are already in place and will be assumed by the buyer. Downstairs, the unfinished basement offers even more potential. It includes an egress window, has been professionally waterproofed, and features thoughtful upgrades such as a foundation crack repair, two pillar reinforcements, and a backup sump pump. Completing the system, the hot water heater is an electric and propane hybrid with an eco mode option, designed with efficiency in mind. Beyond the home itself, the lifestyle here is a big part of the appeal. Centreville offers small-town charm with plenty to explore close by. Downtown is home to local favorites like Mamma Mia Italian Bistro, Doc’s Riverside Grille, Colosseum Pizza, and Commerce Street Creamery for coffee, ice cream, or an easy stop downtown. Outdoor time comes naturally with Tuckahoe State Park just a short drive away, offering miles of trails, a lake for kayaking or fishing, and wide open space to unwind. Wye Island Natural Resources Management Area is also nearby, known for its quiet shoreline, wooded trails, and abundant wildlife. With community events, local shops, and quick access to Route 301 for travel toward Annapolis or the Eastern Shore beaches, life here feels relaxed, connected, and easy to enjoy. This property is being sold as a VA short sale and is subject to bank approval. Per short sale requirements, the home must be on the market for a minimum of 15 days before a contract can be written and accepted.

138 Cool Meadow Dr, Centreville

Listing courtesy of EXP Realty, LLC. Contact:

336 Timber Ln, Grasonville
$455,000
4 Beds ⋅ 3 Baths
OPEN DAILY BY APPT. SPACE, COMFORT & LOCATION! (NOTE: Pictures with furniture are virtually staged). You really can have it all! Welcome to 336 Timber Ln in Grasonville! This well-maintained two story colonial offers 4 bedrooms, 2.5 bathrooms, and a 2 car garage, all just minutes from Kent Island and the Chesapeake Bay Bridge. An ideal location for an easy commute while enjoying everything the Eastern Shore has to offer! Inside, you’ll find a spacious, inviting layout with a well sized kitchen featuring a breakfast bar that opens to the family room and sunroom. Picture cozy evenings by the fireplace as the temperatures drop! The sunroom adds even more flexible living space, perfect for a breakfast nook, additional seating, or simply enjoying the natural light. Upstairs, the spacious primary suite features a large walk-in closet and private bath with dual sinks, a soaking tub, and a separate water closet. Three additional bedrooms, a full hall bath, and multiple closets provide plenty of room for family, guests, or a home office. Love outdoor living? Start your morning with coffee on the welcoming front porch, then enjoy the large deck for grilling, entertaining, or unwinding with your favorite evening beverage. You’ll also love the convenient location near waterfront restaurants, marinas, the Yacht Club, shopping, and easy access to Route 50. Looking for room to spread out, spaces to enjoy, and a location that makes everyday life easier? Come see what 336 Timber Lane has to offer!

336 Timber Ln, Grasonville

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

227 Dorchester Rd, Stevensville
$449,900
3 Beds ⋅ 3 Baths
Welcome to 227 Dorchester Road — a nicely updated 3-bedroom, 3-full-bath split foyer tucked on a private, fenced lot in the water-oriented community of Kent Island Estates. The main level features new LVP flooring, a bright kitchen with painted cabinetry, 3 bedrooms and 2 full baths, including a fully renovated primary bath with a custom tiled shower. The hall bath has also been refreshed with updated flooring and paint. The finished lower level offers fantastic flexible living space and was substantially renovated in 2023 with new drywall, electrical, flooring and paint, plus a cozy pellet stove and an existing third full bath. Outside, enjoy the fenced backyard, a large deck with access to the yard and eat-in dining area, a concrete patio and plenty of room for entertaining, gardening or play. There's even a chicken coop that conveys — and the chickens can convey too! The STEP sewer system was installed in 2018, taking one more major item off the list. And when you're ready to get out and enjoy Kent Island, the South Kent Island Trail runs right through the community, while nearby Romancoke Pier offers fishing, crabbing, picnicking and a small sandy beach for launching kayaks. Updated, comfortable and close to the water — this is Kent Island living! Check out the community website for more information on the associations and optional fees for access to the various amenities. The $20/year mandatory fee is for KIE road maintenance.

227 Dorchester Rd, Stevensville

Listing courtesy of RE/MAX Leading Edge. Contact:

102 Sophie Ln, Stevensville
$429,900
4 Beds ⋅ 3 Baths
MOTIVATED SELLERS HAVE FOUND THEIR HOME OF CHOICE! Seller is willing to contribute toward a mortgage rate buy-down with an acceptable offer, giving buyers an opportunity to potentially secure a lower interest rate. Priced well below recent neighborhood comparables, 102 Sophie Lane offers an incredible opportunity to own an end-unit townhome in the sought-after Ellendale community! This home offers a bright, functional layout with plenty of natural light and inviting living spaces. The living room features a shiplap accent wall with an electric fireplace, while the kitchen offers granite countertops and a spacious island. Step outside to the composite rear deck, perfect for relaxing or entertaining. Custom California Closets® organization systems add exceptional storage to the bedroom closets. Enjoy the Ellendale lifestyle with access to a community pool, piers and walking trails, all just minutes from shopping, dining and Route 50. With motivated sellers, attractive pricing and a potential mortgage rate buy-down, this is an opportunity you don’t want to miss!

102 Sophie Ln, Stevensville

Listing courtesy of Douglas Realty LLC. Contact:

136 Long Dr, Queenstown
$425,000
3 Beds ⋅ 3 Baths
Nestled in the prestigious Queenstown Harbor community, this exquisite carriage house-style townhouse offers an unparalleled blend of luxury and comfort. Spanning 1,916 square feet, this meticulously maintained residence is a sanctuary for those who appreciate high-end living and an exclusive lifestyle. Step inside to discover an open floor plan that seamlessly integrates elegance and functionality. The interior boasts stunning hardwood floors, complemented by plush carpeting and ceramic tile, creating a warm and inviting atmosphere. Crown moldings and ceiling fans add a touch of sophistication, while the corner brick fireplace serves as a captivating focal point, perfect for cozy evenings. The gourmet kitchen is a chef's dream, featuring stainless steel appliances, including a built-in microwave, dishwasher, and electric oven/range. Ample cabinetry and counter space ensure that culinary creations can be crafted with ease. Retreat to the luxurious master suite, where tranquility reigns. The thoughtfully designed layout includes two additional bedrooms, providing ample space for guests or a home office. With two full bathrooms and a convenient half bath, morning routines are a breeze. Step outside to your private deck, where you can savor morning coffee or unwind with a glass of wine while overlooking the lush golf course views. The meticulously landscaped exterior features a well-maintained gutter system and sidewalks, enhancing the overall curb appeal. A detached garage and ample driveway parking ensure convenience for you and your guests. For water enthusiasts, this property offers private access to a cove just blocks away, perfect for boating and fishing adventures. The serene surroundings invite you to embrace an active lifestyle, whether it's a leisurely day on the water or a round of golf at the nearby course. This home is not just a residence; it's a lifestyle choice that embodies luxury, comfort, and convenience. Experience the best of Queenstown Harbor living, where every detail has been thoughtfully curated to elevate your everyday life. Don't miss the opportunity to make this exceptional property your own.

136 Long Dr, Queenstown

Listing courtesy of Coldwell Banker Realty. Contact:

125 Forest Rd, Grasonville
$405,000
3 Beds ⋅ 2 Baths
Welcome to 125 Forest Road in Grasonville! This beautifully fully remodeled home is move-in ready and offers modern updates throughout. The brand-new kitchen features fresh finishes and updated amenities, while the newly renovated bathrooms add style and functionality. Major improvements include a new HVAC system, new roof, new well, and refinished floors, providing both peace of mind and lasting value. Tucked away on a quiet cul-de-sac, this home offers a peaceful setting while remaining conveniently located near Route 50 for an easy commute and access to shopping, dining, and recreation. Located in a desirable area with access to good schools, this extensively updated home is an excellent opportunity for buyers looking for comfort, convenience, and a truly turn-key property.

125 Forest Rd, Grasonville

Listing courtesy of Homecoin.com. Contact:

117 Wright Rd, Chester
$399,999
3 Beds ⋅ 2 Baths
Nestled up to vast farm land, this exquisite ranch-style home offers a perfect blend of comfort and sophistication.This residence boasts a well-maintained exterior with charming vinyl siding, inviting you into a space that feels both warm and welcoming. Step inside to discover an open floor plan that seamlessly integrates the kitchen and living areas, creating an ideal setting for both relaxation and entertaining. The luxury vinyl plank flooring flows gracefully throughout, providing a stylish yet durable foundation for your daily life. Natural light pours in, accentuating the spaciousness and warmth of the home. The heart of this residence is undoubtedly the modern kitchen, equipped with SS Appliances that cater to your culinary aspirations. Featuring an electric oven/range, a sleek microwave, and a dishwasher, this kitchen is designed for both functionality and elegance. The refrigerator offers ample storage for all your gourmet ingredients, making meal preparation a delight. With 3 bedrooms and 2 full bathrooms, this home provides plenty of space for comfort and privacy. Updated Ceiling Fans and Lights throughout the home ensure a refreshing atmosphere year-round. Brand New Roof and Water Heater Installed 2024. Step outside to enjoy the inviting patio, new fence, perfect for morning coffee or evening gatherings under the stars. The expansive 0.26-acre lot offers plenty of room for outdoor activities, gardening, or simply enjoying the tranquility of your surroundings. Parking is a breeze with an attached garage and additional driveway space for guests. The gravel driveway adds a rustic charm while ensuring easy access. This property is not just a house; it's a lifestyle. Experience the joy of living in a well-appointed home that combines modern conveniences with a cozy atmosphere. Whether you're hosting friends or enjoying a quiet evening, this residence is designed to meet your every need. Embrace the opportunity to make this beautiful home your own and enjoy the exclusive lifestyle it offers. Sale of this Home is Contingent upon Sellers finding their home of choice.

117 Wright Rd, Chester

Listing courtesy of Douglas Realty LLC. Contact:

105 Bobbit Ct, Stevensville
$387,500
3 Beds ⋅ 2 Baths
**USDA zero down payment financing with favorable rates available for this property** Fantastic Price Improvement, and sellers will provide a 1-year home warranty!! This charming ranch-style home, renovated in 2020, offers a perfect blend of modern comfort and classic appeal. With a thoughtfully designed living space, this residence features three inviting bedrooms and two full bathrooms, including a luxurious primary bath with upgraded countertops and a walk-in tiled shower. The heart of the home is the spacious eat-in kitchen, complete with stainless steel appliances, an island for casual dining, and a family room that flows seamlessly off the kitchen, making it ideal for gatherings. Natural light abounds and the recessed lighting & ceiling fans enhance the warm ambiance throughout. Step outside to enjoy the maintenance-free deck and porch, perfect for relaxing or entertaining while overlooking the level fenced rear yard. Abundant off-street paved parking for numerous boats, RV's & vehicles. Situated in a welcoming community, this home is surrounded by well-maintained parks and recreational areas, providing ample opportunities for outdoor activities including; boating, fishing/crabbing, cook-outs & swimming on the sandy beaches along the scenic Chesapeake Bay. With easy access to restaurants, shops and a friendly neighborhood atmosphere, this property is not just a house; it's a place to create lasting memories. Experience the comfort and community spirit that this lovely Stevensville home and Kent Island lifestyle has to offer!

105 Bobbit Ct, Stevensville

Listing courtesy of Beam Realty Group, Inc.. Contact:

116 Chesapeake Estates Dr, Stevensville
$384,900
3 Beds ⋅ 1 Baths
Experience Chesapeake Bay living for under $385,000! Ideally located just up the road from the community beach, picnic area, and playground on the Chesapeake Bay, this beautifully updated rancher offers over 1,400 sqft with the perfect blend of comfort, value, and location. Thoughtfully updated, this home features new flooring (2026), a new heat pump (2025), a new roof (2024), and newer siding and windows (except bay window), offering added peace of mind for years to come. The spacious 22' x 24' detached garage provides plenty of room for parking, a workshop, hobbies, or additional storage. Outdoor enthusiasts will love being just minutes from the South Island Trail, a scenic 7-mile paved trail stretching from Romancoke Fishing Pier to Matapeake State Park—perfect for walking, running, and biking. Enjoy convenient access to a nearby public boat ramp, waterfront dining, shopping, medical facilities, and everyday amenities. Don't miss this opportunity to own a home in this sought-after Chesapeake Bay waterfront community at an exceptional price! Come discover the lifestyle and make this charming rancher your own. Square Footage based on Cubicasa Floor Plan, Buyer to verify

116 Chesapeake Estates Dr, Stevensville

Listing courtesy of Rosendale Realty. Contact:

1645 Ruthsburg Rd, Centreville
$375,000
3 Beds ⋅ 2 Baths
BACK ON THE MARKET—through no fault of the sellers! Sellers of 1645 Ruthsburg Rd are offering up to $18,000 toward buyer’s allowable closing costs, prepaid expenses, and/or a lender-approved interest-rate buydown with a mutually accepted contract on or before October 31, 2026. Buyers may alternatively negotiate a price reduction in lieu of the closing-cost credit. All incentives are subject to seller-approved price and terms, lender approval, and applicable loan-program limits.Opportunity meets location at this charming 1891 farmhouse situated on a spacious ¾-acre lot just a few short miles off 301 . Located within the Village Center District. And NO TOWN TAXES. The home features 3 bedrooms and 2 full baths, blending historic character with thoughtful updates including granite countertops and stainless steel appliances. Outside, the standout feature is the impressive 32' x 24' detached garage with two 10' x 10' doors. Enjoy the convenience of being just minutes from downtown Centreville, schools, shopping, dining, and major commuter routes while maintaining the space and flexibility that only a property like this can provide.

1645 Ruthsburg Rd, Centreville

Listing courtesy of Samson Properties. Contact:

249 White Marsh Rd, Centreville
$365,000
3 Beds ⋅ 1 Baths
Back to market at a price you absolutely cannot argue with. We have an appraisal in hand for $445,000, conducted just last year — walk into this home with $80,000 of instant equity. At this price, it will be back under contract quickly, so don't hesitate. Welcome to 249 White Marsh Road, a clean, move-in-ready home on a beautifully landscaped property in Centreville. This well-maintained home features beautiful wood floors, a bright and inviting living space, and a recently renovated bathroom. Pride of ownership shows throughout, so the next owner can move right in and enjoy the home from day one. The lower level offers valuable flex space — perfect as a home office, workout area, hobby room, or potential additional bedroom. Outside, the landscaped yard provides a peaceful setting with plenty of room to relax, entertain, and enjoy the outdoors. And the location works as hard as the price: it's a short trip to Route 301 and the Bay Bridge, making this an ideal home base for commuters heading in either direction. Whether you're a first-time buyer, downsizing, or simply looking for a well-cared-for home with room to make it your own, 249 White Marsh Road is a property worth seeing.

249 White Marsh Rd, Centreville

Listing courtesy of Real Broker, LLC. Contact:

715 Winchester Creek Rd, Grasonville
$365,000
**Seller is motivated and ready to move on to the next project—**all offers will be considered! Currently priced significantly below assessed value. This west-facing waterfront lot on Winchester Creek offers over 4 acres of private, NO-HOA living directly off the Chester River. A fully engineered site plan is complete and ready for final submissions—over a year of professional engineering has gone into identifying the ideal build site, saving you time and effort in the permitting process. Enjoy immediate use of the waterfront this season while your new home is under construction. The property features a pier, boat ramp, and partially bulk headed shoreline, providing excellent water access from day one. By boat, you're just minutes from the world-famous Kent Narrows, with Rock Hall and Chestertown nearby. The fishing here is top-notch, with the Chester River producing some of the Eastern Shore’s largest catfish and snakeheads, in addition to excellent salt and brackish water opportunities. Calm and protected, Winchester Creek is ideal for kayaking and paddle boarding. Bring your own builder or use ours—this is a rare opportunity to create your dream waterfront retreat.

715 Winchester Creek Rd, Grasonville

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

815 Chester River Dr, Grasonville
$349,900
3 Beds ⋅ 2 Baths
REDUCED!! NEWER Furnace, NEWER Hot Water Heater, NEWER Dishwasher and No Flood Zone. Discover the desired WATERFRONT Chester River Beach Community! Just one block from the Boat landing with boat ramp, boat slips, playground, beach, pavilio , picnic area and kayak storage! This one level Rancher boasts 1,593 sqft. of living space and features an open floor plan. The large kitchen boasts an eat-in area with plenty of room for a large dining table for all to gather! The heart of the home is the cozy wood stove, creating a warm atmosphere in the family room. Enjoy three spacious bedrooms and two full baths, which includes the ensuite bath in the primary! Step outside to your huge backyard and enjoy nights under the stars or unwind and grill dinner in your own little courtyard! One car garage is perfect for storage along with an extensive driveway for ample parking. Just take a very short stroll to the community landing and indulge in fishing, crabbing, kayaking or simply soaking in the tranquil views and the BEST SUNSETS! NEW Furnace '24, NEW Hot Water Heater '25, NEW Dishwasher '25 and No Flood Zone here! Top-rated schools, nearby parks and Kent Island Cross Trail is just an added bonus! Close to Marinas, Waterfront Dining, the Narrows, Boutique Shopping this location is perfect for those seeking a vibrant lifestyle on the Shore! Easy on and off RT 50 for the commuter. Don't miss your opportunity to be in Chester River Beach at this great price!

815 Chester River Dr, Grasonville

Listing courtesy of RE/MAX Executive. Contact:

1102 Marion Quimby Dr, Stevensville
$334,900
2 Beds ⋅ 3 Baths
Motivated seller! Price reduced! 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:

5011 Bridgepointe Dr, Chester
$315,000
3 Beds ⋅ 3 Baths
Nestled in the heart of Kent Island, this charming 3 Bedroom, 2 Full Bathroom townhome with Bonus Room, offers the perfect blend of comfort, convenience, and peaceful surroundings. Located in the desirable Bridgepointe community, this home features major updates including a newer roof, HVAC system, and water heater providing peace of mind for years to come. Enjoy a private backyard setting that backs to mature trees, creating a serene outdoor retreat, while being just steps from the community lake, walking paths, and boat parking lot! Inside, the functional layout offers spacious living areas, comfortable bedrooms, and plenty of natural light throughout. Whether you're looking for a primary residence, weekend getaway, or low-maintenance lifestyle near the Chesapeake Bay, this Kent Island gem is ideally situated close to shopping, dining, marinas, and commuter routes. Schedule your tour today! Home sold as-is.

5011 Bridgepointe Dr, Chester

Listing courtesy of Keller Williams Realty Centre. Contact:

116 Homestead Ln, Stevensville
$299,999
6 Beds ⋅ 2 Baths
Back to ACTIVE! Rare opportunity in the highly coveted Love Point community of Stevensville! Nestled on 1.67 acres and bordered by the State of Maryland Department of Natural Resources, this unique property offers a private, peaceful setting surrounded by nature. The existing home is a true blank canvas and presents an incredible opportunity for investors, builders, or buyers with a vision to bring this property back to life. A full renovation is needed, but the possibilities are endless for creating a custom retreat in one of Queen Anne’s County’s most desirable locations. Enjoy the serenity of the natural surroundings while being conveniently located near waterfront destinations, marinas, shopping, dining, and commuter routes. Properties with this combination of acreage, privacy, and location are rarely available. Bring your plans, your imagination, and your vision—this is the perfect project for those looking to create something truly special in Love Point. This is an estate sale being sold strictly as-is.

116 Homestead Ln, Stevensville

Listing courtesy of Keller Williams Flagship. Contact:

124 Wilton Rd, Chestertown
$294,900
3 Beds ⋅ 1 Baths
MOVE IN READY!! Charming 3 bedroom ranch home in the desirable water oriented community of Chester Harbor and Queen Anne’s County school district. This recently updated home offers a wonderful blend of modern comfort, convenience and peaceful surroundings. The home features a carefully updated galley kitchen with beautiful custom countertops, soft close cabinets and stainless steel appliances. The home also offers a reverse-osmosis water system in the kitchen. Numerous updates have been completed recently, including new LVP flooring, carpet, light fixtures, a new roof in 2020, new windows in 2021, new exterior and entry doors in 2023. Perfect location for dog lovers with a recently added split-rail fence enclosing the backyard. Walking distance to Round Top Park and minutes from Downtown Chestertown where you can enjoy local restaurants, shops, waterfront attractions, the dog park and the popular farmers market every Saturday! Don't miss this opportunity to make this wonderful property your new home!

124 Wilton Rd, Chestertown

Listing courtesy of Doug Ashley Realtors, LLC. Contact:

2551 Church Hill Rd, Centreville
$250,000
Village Center Zoning – Residential & Commercial Potential! Explore the possibilities at 2551 Church Hill Road in Centreville, Maryland! Situated in Queen Anne's County's Village Center (VC) zoning district, this property features an existing dwelling and offers potential for a variety of residential and commercial uses. Currently vacant, the property presents an opportunity for buyers seeking a residence, possible business location, or investment property. Village Center zoning is designed to accommodate a mix of uses while preserving the character of the surrounding community. Any proposed commercial use or conversion is subject to applicable zoning, permitting, and county approvals. Buyers are encouraged to verify their intended use with Queen Anne's County Planning and Zoning.. Additional 1 Acre Perc Approved lot behind it is available as well for a package deal offering 2.57 Acres total. (111 Hatchett Rd Centreville, MD 21617 )

2551 Church Hill Rd, Centreville

Listing courtesy of Taylor Properties. Contact:

106 Fischer Rd, Grasonville
$240,000
3 Beds ⋅ 2 Baths
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:

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