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815 Chester River Dr, Grasonville
$349,900
3 Beds ⋅ 2 Baths
REDUCED!! 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:

54f Queen Caroline Ct, Chester
$349,900
3 Beds ⋅ 3 Baths
Completely remodeled in 2026 with a new kitchen to include new appliances, quartz counters, and backsplash, 3 new bathrooms, all new flooring throughout, new washer and dryer and freshly painted. Nestled in the serene enclave of Queens Landing, this exquisite remodeled in 2026 Colonial townhouse offers a harmonious blend of luxury and comfort. Spanning 1,440 square feet, the open floor plan invites you to experience a seamless flow between the combination dining and living areas, perfect for both intimate gatherings and entertaining. The family room, conveniently located off the kitchen, creates a warm atmosphere where cherished memories are made. Indulge in the elegance of three spacious bedrooms all on the same level and two and a half beautifully recently remodeled bathrooms, designed for relaxation and rejuvenation. The inviting ambiance is enhanced by the cozy fireplace, providing a perfect backdrop for cozy evenings at home. Step outside to discover the community's stunning outdoor pool, where you can unwind under the sun or enjoy leisurely afternoons by the water. With direct access to the Chester River, water enthusiasts will appreciate the navigable waters, ideal for kayaking or simply soaking in the tranquil views. Queens Landing boasts an array of amenities, including a clubhouse, exercise room, and scenic bike trails, fostering an active and vibrant lifestyle. The meticulously maintained common grounds offer a picturesque setting for leisurely strolls or social gatherings. This property is not just a home; it's a lifestyle choice that embodies luxury, comfort, and community. Experience the best of waterfront living in this exceptional residence, where every detail has been thoughtfully curated for your enjoyment. Schedule your tour today!!

54f Queen Caroline Ct, Chester

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

1305 Marion Quimby Dr, Stevensville
$344,900
2 Beds ⋅ 3 Baths
Welcome to 1305 Marion Quimby Drive in Stevensville, a rare waterfront opportunity offering stunning views, low-maintenance living, and direct access to the best of Kent Island’s coastal lifestyle. This beautifully positioned 2-bedroom, 2.5-bath home sits right along the water, delivering breathtaking panoramic views you’ll enjoy from sunrise to sunset. Whether you’re sipping your morning coffee or unwinding in the evening, the peaceful waterfront setting creates the perfect backdrop for everyday living. Step outside and you’re immediately connected to the scenic waterfront walking trail ideal for morning jogs, sunset strolls, or simply soaking in the shoreline beauty. For boating enthusiasts, the property also includes a deeded boat slip, making it effortless to get out on the Chesapeake Bay whenever the mood strikes. Inside, you’ll find a thoughtfully designed layout with two spacious bedrooms, each offering privacy and comfort, plus two full bathrooms and a convenient half bath for guests. The home blends relaxed coastal charm with functional living spaces perfect for year-round enjoyment or a weekend retreat. Water views. Boat access. Community pool. Community fitness center and clubhouse. Walkable waterfront lifestyle. This is Kent Island living at its finest.

1305 Marion Quimby Dr, Stevensville

Listing courtesy of Keller Williams Realty Centre. Contact:

53 Queen Caroline Ct, Chester
$329,000
2 Beds ⋅ 3 Baths
Nestled in the community of Queens Landing, this townhome offers a blend of coastal charm and contemporary elegance with carefree living. Boat slips with provisioned boats when available through marina along with Kayaking and storage. With 1,440 square feet of thoughtfully designed living space, this home is a sanctuary of comfort and style. Step inside to discover an inviting open floor plan that seamlessly connects the living and dining areas, creating an ideal space for entertaining or quiet evenings at home. The family room, conveniently located off the kitchen, features an electric fireplace, providing a cozy ambiance for gatherings. On the second level, are two bedrooms both with their private full bath. The most recent upgrades include; New HVAC, new electric fireplace, new kitchen appliances (GE Profile), updated bathroom, new shower, new carpeting and painted throughout. The community amenities include access to an outdoor swimming pool, tennis courts, and pickleball courts, all designed for an active and social lifestyle. The clubhouse and fitness center provide additional opportunities for relaxation and recreation. This home is conveniently located off of 301/50 and minutes from the Bay Bridge for an easy commute. to Annapolis/DC or Baltimore. NOTE; Community upgrade for Fios internet in process and a line of new trees is going behind the home this fall for added privacy as per HOA

53 Queen Caroline Ct, Chester

Listing courtesy of EXP Realty, LLC. Contact:

217 Edmore Rd, Chestertown
$325,000
3 Beds ⋅ 2 Baths
Lovingly restored rancher located on a a quiet street in sought after Chester Harbor. Generous sized corner lot, with beautiful landscaping and asphalt drive. Home had a complete renovation in 2020 inside and out and practically everything is new since then. Enter into an inviting and updated open floor plan that combines living and dining area, perfect for entertaining and large gatherings. Updated laminate plank floors throughout entire home with SS appliances and kitchen breakfast bar, plus separate dining area. Stackable laundry and half bath conveniently located just off dining area. The sun room, over looking the back garden makes a great sitting room, office, or flex space. Down the hall you'll find 3 good sized bedrooms, all with double closets, a good sized bathroom with modern vanity, laminate floors and tub shower. Outside is a gardener's oasis with mature specimen plantings, just waiting for you to make it your own!

217 Edmore Rd, Chestertown

Listing courtesy of Doug Ashley Realtors, LLC. Contact:

205 Bryantown Lndg, Queenstown
$324,900
4 Beds ⋅ 2 Baths
MAJOR PRICE IMPROVEMENT! Discover this updated home that blends classic architecture with modern living, offering 1,783 sq. ft. of versatile space. Venture inside to find a welcoming traditional floor plan with new luxury vinyl plank flooring and fresh interior paint that flows from the living room to dining room and well-appointed bedrooms. The upgraded kitchen, equipped with white shaker cabinetry, stainless-steel appliances and granite countertops, is a perfect place for culinary enthusiasts. The three bedrooms and full bathroom equipped with a stall shower and whirlpool tub, ensures comfort and relaxation after a long day. The finished 2nd level with new carpet flooring can be converted or used into a 4th bedroom while the main level sunroom with its bright airy ambience is a perfect spot for entertaining. Outside, enjoy the tranquility of your front and rear yards, great for gardening or outdoor activities.

205 Bryantown Lndg, Queenstown

Listing courtesy of Century 21 Downtown. Contact:

45 Queen Neva Ct, Chester
$318,500
2 Beds ⋅ 3 Baths
Price Improvement! Seller is offering closing cost assistance for qualified buyers! This charming townhouse in Queens Landing offers a perfect blend of comfort and community amenities. Step inside to discover a traditional floor plan featuring a cozy living room off the eat-in kitchen, with a separate family room ideal for gatherings. The home boasts two spacious bedrooms and 2.5 baths, including a primary bath for added convenience. Updates include new flooring throughout; LED lighting, granite counters, newer windows and HVAC system. Enjoy modern amenities with a suite of appliances, including a built-in microwave, dishwasher, electric range, washer and dryer. Outside, the community shines with well-maintained sidewalks, streetlights, and a variety of recreational facilities. Take advantage of the clubhouse, outdoor pool, tennis courts, and scenic waterfront jogging paths. The nearby Chester River provides a serene backdrop for leisurely strolls and outdoor activities, with access to the Cross Island Trail connecting waterfront features at Terrapin Park and The Narrows. Located within a vibrant neighborhood, residents benefit from access to parks and essential public services. This home is not just a place to live; it's a gateway to a fulfilling lifestyle in a welcoming community. Some photos displayed used AI and may not be 100% accurate. Please schedule an in-person tour to view this beautiful property.

45 Queen Neva Ct, Chester

Listing courtesy of Coldwell Banker Realty. Contact:

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:

205 Dominion Ln, Chester
$300,000
3 Beds ⋅ 2 Baths
Opportunity on Kent Island! Welcome to 205 Dominion Lane in Chester, a detached home situated on a 0.27-acre lot with plenty of potential for the right buyer. Currently used as a rental, this property offers an opportunity for homeowners, investors, or buyers looking to make a home their own. While the property could benefit from some updates and TLC, it provides a chance to add value through improvements and personal touches. Whether you're looking for a primary residence, an investment property, or your next renovation project, this home offers flexibility in a desirable Kent Island location. Enjoy convenient access to shopping, dining, local amenities, and Route 50 for commuting. Bring your vision, explore the possibilities, and schedule your showing today!

205 Dominion Ln, Chester

Listing courtesy of EXP Realty, LLC. Contact:

Damsontown Road, Queen Anne
$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 Road, Queen Anne

Listing courtesy of Eastern Shore Real Estate, LLC. 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:

54 Queen Caroline Ct, Chester
$299,900
3 Beds ⋅ 3 Baths
Motivated Seller now offering $5,000 closing help! This home is move in ready. Discover refined waterfront community living in this beautifully updated and rarely available 3-bedroom, 2.5-bath condo in the highly desirable Queen’s Landing community. Thoughtfully designed with both comfort and style in mind, this spacious home offers fresh interior paint, an inviting open layout, and a beautifully updated kitchen featuring elegant quartz countertops—perfect for everyday living, relaxing weekends, and entertaining family and friends. Natural light fills the living spaces, while the seamless flow between the kitchen, dining, and living areas creates a warm and welcoming atmosphere throughout the home. Step outside to enjoy your private screened porch—ideal for morning coffee or evening unwinding—or host summer gatherings on the private patio designed for grilling and outdoor entertaining. Rare opportunities like this don’t come along often in Queen’s Landing, especially with the combination of three bedrooms, modern updates, and exceptional outdoor living spaces. Enjoy a true resort-style lifestyle with community amenities that include a swimming pool, fitness center, pickleball and tennis courts, and a private marina. Whether you’re looking for a full-time residence, weekend retreat, or low-maintenance coastal lifestyle, this home offers the perfect balance of relaxation and convenience. Ideally located in the heart of Chester, you are just minutes from waterfront dining, shopping, entertainment, and major commuter routes—making it easy to enjoy everything the Eastern Shore has to offer while staying connected to Annapolis, Baltimore, and Washington, D.C. Some photos are for illustrative purposes only.

54 Queen Caroline Ct, Chester

Listing courtesy of Island Realty, LLC. 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:

1606 Marion Quimby Dr, Stevensville
$285,000
3 Beds ⋅ 2 Baths
Welcome to 1606 Marion Quimby Drive in Stevensville, Maryland! Enjoy convenient, low-maintenance living in this inviting upper-level condo offering 3 bedrooms, 2 full baths, and 949 square feet of comfortable living space. Step inside to discover a functional floor plan featuring a cozy wood-burning fireplace, perfect for relaxing evenings at home. The private balcony provides a wonderful spot to enjoy your morning coffee or unwind at the end of the day. Additional conveniences include in-unit laundry, making everyday living that much easier. Beyond the condo itself, residents can enjoy the added benefits of a community designed for convenience and relaxation. Spend warm summer days lounging by the community’s in-ground swimming pool, take advantage of the recreation center, and enjoy the beautifully landscaped, professionally maintained common areas. With exterior common-area maintenance handled for you, there’s more time to enjoy everything Kent Island has to offer. It’s a wonderful combination of affordable comfortable living, community amenities, and everyday convenience! Location is everything! Conveniently situated near grocery stores, shopping, restaurants, and everyday essentials, with quick access to Route 50 and the Chesapeake Bay Bridge. Commuters will appreciate the easy drive to Annapolis and surrounding areas while enjoying all that Kent Island has to offer. Even better, the seller is offering a $5,000 contribution toward buyer closing costs or an interest rate buy-down, subject to lender approval and applicable loan guidelines! This added incentive provides an opportunity to help reduce upfront expenses or potentially lower monthly mortgage payments. Whether you’re purchasing your first home, looking to downsize, or searching for an Eastern Shore getaway, this property offers a wonderful combination of comfort, convenience, and location. Schedule your private showing and discover the possibilities!

1606 Marion Quimby Dr, Stevensville

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

1403 Marion Quimby Dr, Stevensville
$285,000
3 Beds ⋅ 2 Baths
Discover the charm of Thompson Creek Condos. This beautifully maintained 3-bedroom, 2-bathroom unit offers an inviting open floor plan, perfect for both relaxation and entertaining. Enjoy the warmth of an electric fireplace in the cozy living area, while the spacious eat in kitchen is equipped with essential appliances including a dishwasher and stacked washer/dryer. Step outside to your private balcony, where serene pond views create a tranquil retreat. The community boasts exceptional amenities, including a refreshing outdoor pool, a fitness center, and scenic jogging paths, ensuring an active lifestyle right at your doorstep. With sidewalks and street lights enhancing the neighborhood's charm, evening strolls become a delightful routine. Thompson Creek Condos is ideally situated near top-rated schools, lush parks, and essential public services, making it a prime location for convenience and community engagement. The association fee covers maintenance and insurance, allowing you to enjoy a worry-free lifestyle. Experience the best of both worlds-relaxation and recreation-within this vibrant community. Whether you're lounging by the pool or exploring the nearby river, this property offers a lifestyle that is both enriching and fulfilling. Don't miss your chance to call this stunning condo home!

1403 Marion Quimby Dr, Stevensville

Listing courtesy of Benson & Mangold, LLC. Contact:

101 Bufflehead Ct, Chester
$275,000
2 Beds ⋅ 2 Baths
Welcome to easy, low-maintenance living in the sought-after Bayside community of Chester! This beautifully maintained 2-bedroom, 2-bathroom condo offers the perfect combination of comfort, style, and convenience. Gorgeous hardwood floors flow throughout, while the spacious family room, kitchen, and dining area create an inviting layout perfect for everyday living and entertaining. Both bedrooms offer generous space, with the primary suite featuring a walk-in closet and private full bathroom. Enjoy the fresh air and beautiful weather from your private deck, while convenient in-unit laundry adds to the ease of everyday living. The Bayside community offers fantastic amenities, including a clubhouse, fitness center, and outdoor pool, along with easy access to the Cross Island Trail for walking, running, and biking. Conveniently located just minutes from local dining, shopping, and the Chesapeake Bay Bridge. Don't miss your opportunity to enjoy all that Kent Island living has to offer!

101 Bufflehead Ct, Chester

Listing courtesy of The KW Collective. Contact:

15 Mariners Way Unit A-1, Stevensville
$265,000
2 Beds ⋅ 2 Baths
Chesapeake Waterfront Lifestyle Without the Waterfront Price Tag! Welcome to a beautifully transformed retreat in Kent Cove, where easy coastal living meets the comfort and convenience of a thoughtfully updated home. This exceptional 2-bedroom, 1.5-bath townhouse offers a rare opportunity to enjoy water views, community water access, multiple docks, resort-style amenities, and expansive outdoor living—all in a peaceful Stevensville setting just one minute from Routes 301/50. From the moment you arrive, you'll notice that this isn't your typical townhouse. Extensively updated and lovingly maintained, the home received approximately $25,000 in improvements in 2018, including a complete kitchen renovation, updated bathrooms, new flooring throughout, stainless steel appliances, granite countertops, fresh paint, updated water-heater components, and a custom cabinet niche/coffee station in the dining area. An additional $3,000 in improvements was completed in 2026, keeping the home fresh and move-in ready. The heart of the outdoor experience is the new 8' x 22' Trex deck—a substantial private entertaining space designed for morning coffee, evening cocktails, outdoor dining, or simply enjoying the peaceful Kent Cove surroundings. A second front deck opens to a relaxing common area, while the semi-private common area behind the home creates an additional sense of privacy and space. And then there's the water. Enjoy water views and community access to the water, with three community docks providing opportunities to take in the scenery and enjoy the Eastern Shore lifestyle. Whether you're looking for a peaceful place to unwind after a long day, a weekend escape, or an easy-care home where you can enjoy the outdoors without the responsibilities of a larger property, Kent Cove delivers. The community's amenities add exceptional value and convenience. The $522 monthly HOA fee includes water and sewer, twice-weekly trash pickup, snow removal, maintenance of common areas, exterior townhouse maintenance, a community pool, and access to three docks. It's a lifestyle designed to let you spend less time maintaining a property and more time enjoying it. A detached one-car garage provides valuable storage and parking, while the two-level layout offers comfortable separation between living and private spaces. Best of all, you get the tranquility and character of Eastern Shore living while remaining incredibly convenient to major commuter routes. Routes 301/50 are just one minute away, putting the Bay Bridge, Annapolis, shopping, dining, and everything Stevensville has to offer within easy reach. Updated. Waterfront-oriented. Turnkey. Low maintenance. Convenient. If you've been waiting for an opportunity to enjoy the Kent Island lifestyle without taking on the price and upkeep of a detached waterfront home, this is the one to see. Come experience the views, the decks, the water, and the unique sense of community that make Kent Cove such a special place to call home.

15 Mariners Way Unit A-1, Stevensville

Listing courtesy of RE/MAX Plus. Contact:

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