Refine Search
Map
Sort by
$399,000
2 Beds ⋅ 2 Baths
Waterfront Living on Thompson Creek – Rare End-Unit Townhome Fantastic opportunity to own an end-unit waterfront townhome with direct views of Thompson Creek, complete with an assigned pier featuring power and water. Inside, gleaming hardwood floors flow through the kitchen and living room. The main level offers a convenient bedroom, while upstairs you'll find a huge loft-style primary suite complete with a spacious primary bathroom featuring an oversized walk-in shower and an equally impressive walk-in closet. A versatile bonus room offers flexibility as a 3rd bedroom or home office. The kitchen offers ample counter space and storage alongside a large dining area, perfect for entertaining. Step outside to a spacious deck to soak in the water views, plus a second private balcony off the primary bedroom. With western exposure, enjoy breathtaking sunsets over the creek every evening. The HOA maintains the pier as well as all exterior upkeep of the home, including the roof and siding, offering true low-maintenance waterfront living. Ideally located on Kent Island, just a half mile to Route 50 and minutes to two shopping centers featuring Food Lion, Target, and a variety of restaurants. Incredible value at $399,000 for waterfront living with a private pier. Furnishings are available for purchase separately, excluding personal items.

101 Marion Quimby Dr, Stevensville

Listing courtesy of Engel & Volkers Annapolis. Contact: (443) 292-6767
$749,900
3 Beds ⋅ 2 Baths
Nestled within the prestigious Oyster Cove community, this exquisite 3rd floor Penthouse corner residence offers a harmonious blend of luxury and comfort, perfectly situated along the serene Kent Narrows/ Prospect bay. Served by elevator, the contemporary architectural style is complemented by high-end finishes throughout, including luxury vinyl plank flooring and elegant built-ins that enhance the open floor plan. Step inside to discover a spacious family room that seamlessly connects to a gourmet kitchen, featuring upgraded countertops and modern appliances, including a sleek electric range and a convenient dishwasher. The inviting breakfast area is perfect for casual dining, while the primary bath offers a private retreat with sophisticated fixtures. Enjoy the tranquility of river views from your porch, where you can unwind and soak in the picturesque surroundings. The property boasts deeded private 40 foot boat slip, ideal for boating enthusiasts, and a community pool for leisurely afternoons. Additional amenities include a gated entrance, ensuring privacy and security, along with beautifully maintained common grounds and walking paths. With three generously sized bedrooms and a cozy electric fireplace, this home is designed for both relaxation and entertaining. The community offers a wealth of recreational options, including tennis courts, pickle ball and picnic areas, enhancing the luxurious lifestyle that Oyster Cove provides. Experience the ultimate in waterfront living, where every detail has been thoughtfully curated for your enjoyment.

130 Oyster Cove Dr Unit #130, Grasonville

Listing courtesy of Coldwell Banker Waterman Realty. Contact: (410) 643-5005
$589,000
4 Beds ⋅ 2 Baths
Welcome Home to 729 Kimberly Way, nestled in the highly sought-after waterfront community of Cloverfields on Kent Island—where thoughtful updates, exceptional outdoor living, and versatile bonus space combine to create a home you’ll be proud to call your own. This beautifully maintained 4-bedroom, 2-bath raised rancher welcomes you with mature landscaping, vibrant flower beds, a spacious half-circle driveway, and outstanding curb appeal. The extended driveway leads to an oversized detached garage with generous storage above, offering endless potential to be finished into additional workspace, a private office, hobby room, or the perfect retreat to fit your lifestyle. Step into your own backyard oasis, thoughtfully designed for both entertaining and everyday enjoyment. Stamped concrete walkways and patios lead to an expansive two-tier deck, complemented by covered outdoor living space, mature trees for added privacy, and beautifully maintained landscaping that creates a peaceful setting. With ample parking and inviting outdoor spaces, this property is ideal for hosting family and friends or simply relaxing after a day on the water. Inside, you’ll find numerous updates and energy-efficient features throughout. The lower level offers a spacious family room centered around a charming wood-burning stove, creating a warm gathering place while helping reduce heating costs during the cooler months. Paired with the home’s highly efficient geothermal heating and cooling system—a rare and valuable feature on Maryland’s Eastern Shore—you’ll enjoy year-round comfort and exceptional energy savings. The lower level also features a full bathroom, welcoming tiled entry, and updated mechanicals, including a new water heater and new washer and dryer. Upstairs, engineered hardwood flooring flows throughout the main living areas, adding warmth and timeless character. The updated kitchen offers modern appliances and opens seamlessly to the dining area, where sliding glass doors lead to the expansive rear deck overlooking the private backyard. The upper level includes three comfortable bedrooms, including a spacious split primary suite with abundant closet space. The beautifully updated bathroom showcases ceramic tile flooring, an oversized tiled shower, and a relaxing soaking tub. Fresh paint, updated lighting, and meticulous care make this home truly move-in ready. Living in Cloverfields means enjoying some of Kent Island’s most desirable community amenities, including a private sandy beach, marina, boat ramp, fishing pier, swimming pool, clubhouse, playgrounds, and parks—all just minutes from the Chesapeake Bay Bridge, waterfront restaurants, shopping, and everything the Eastern Shore lifestyle has to offer. If you’ve been searching for a home that offers comfort, flexibility, energy efficiency, and an unbeatable waterfront community, 729 Kimberly Way is an opportunity you won’t want to miss.

729 Kimberly Way, Stevensville

Listing courtesy of Samson Properties. Contact: 7033788810
$1,350,000
4 Beds ⋅ 3 Baths
WATERFRONT LIVING on Winchester Creek! This wonderful 4 bedroom, 2.5 bath Grasonville estate offers the ultimate Eastern Shore lifestyle, fully refreshed with a newly painted neutral interior, gleaming refinished hardwoods, and carpet. A grand 2-story foyer with a palladium window, transom accents, and elegant French doors welcomes you inside. The main level features 11' ceilings, a great room with fireplace and a bank of windows with water views, a separate dining room, bright breakfast room, and a fabulous kitchen with an island, pantry, and reverse osmosis water filtration. The main floor primary suite boasts a walk-in closet and a no-threshold shower, complemented by a full, hall bath and convenient half bath. Upstairs, a versatile bonus space features custom built-ins— perfect for an office and media space. Your outdoor resort awaits: a Trex deck with built-in benches and retractable awning leads to a custom paver patio and a sparkling 18’ x 37’ saltwater pool with a tranquil waterfall feature. Boaters will love the deeded boat slip (#10), mooring pile, and private boat lift. Rounding out this incredible home is an oversized 2-car garage with storage space, HVAC (2018), buried 500-gallon propane tank, and full water conditioning system and lush landscaping.

104 Port Ct, Grasonville

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

$160,000
2 Beds ⋅ 1 Baths
Are you looking for the perfect weekend summer house? Look no further! Welcome to 194C Beach Harbor conveniently located in Grasonville. Beach Harbor is a Co-Op RV Resort located right on the water packed with all the amenities you need. Community boat ramp, private beach front area, private pier, volley ball court, shuffle board, community pool and hot tub, club house and so much more. Imagine a weekend home away from home where you can escape the hustle and drive around on your golf cart eating crabs on your front porch overlooking the bay. Pool parties where you don't have to clean the pool or lift a finger! Pop the boat in at the ramp, or launch your kayak right from the beach which is only steps from your front door. This is a doublewide with a newly remodeled sunroom. Trailer is 12X33, attached sunroom 12X32. It has 2 bedrooms, 1 bath, new W/D. Large private driveway big enough for a boat or 3+ cars. Front deck comes with a screened room or remove it for unobstructed water views. Covered back deck has storage shed & boot box. Kitchen appliances are new and this home has been very well maintained and updated every year. Central heat and AC work great and the space is cozy and clean. This is a gated community which is open from mid March and closes the week after Thanksgiving. Community facilities include bathhouse w/showers, laundry, 2 pavillions, beach area, pier, boat launch, tennis court, pickleball, basketball, volleyball, 2 playgrounds. Great community with fun activities for the family like bingo, pig roasts, fireworks, and so much more! If you are looking for a summer spot that wont break the bank you could start enjoying right now! Yearly dues already paid for 2026, and this can come furnished so move right in and start your summer living! See attached disclosures for more details

111 Beach Harbor Dr Unit ##194C, Grasonville

Listing courtesy of Keller Williams Realty Centre. Contact: 4103120000
$700,000
3 Beds ⋅ 3 Baths
Newly adjusted price. Rarely available, this luxurious Severn penthouse in Four Seasons at Kent Island offers the perfect blend of waterfront beauty, comfort, and resort-style living. Built in 2020 and meticulously maintained, the home features an open-concept design filled with natural light and stunning views of Macum Creek and the Chester River. The gourmet kitchen is the heart of the home, showcasing a large island, premium appliances, and picturesque water views. Three spacious bedrooms, two-and-a-half baths, and inviting living spaces provide comfort and flexibility for everyday living and entertaining. Enjoy spectacular sunrises, abundant wildlife, and peaceful water views from your private balcony. Just steps away, you'll find creekside trails, kayak launches, picnic areas, and direct access to the natural beauty that makes Kent Island so special. Located in desirable Phase One, this penthouse offers enhanced privacy, mature surroundings, and freedom from nearby construction. Additional features include an oversized attached garage with interior access and a secure storage room. Residents enjoy access to Four Seasons' exceptional amenities, including a 24,000-square-foot clubhouse, indoor and outdoor pools, fitness center, pickleball and tennis courts, fishing pier, kayak launches, dog parks, walking trails, tiki bar, and more.

2000 Herons Nest Way Unit #401, Chester

Listing courtesy of Real Broker, LLC. Contact: 8504500442
$395,000
4 Beds ⋅ 3 Baths
Kent Island Living at Its Best – Location, Lifestyle & Unlimited Potential! Rare opportunities like this are becoming harder to find in Stevensville. Nestled within a highly sought-after waterfront community, this spacious 4-bedroom, 2.5-bath home offers the perfect combination of location, lifestyle, and value. Situated directly across from the school and just a short stroll to the community recreation fields, this home provides everyday convenience that families will appreciate. The detached garage offers additional storage, workspace, or room for all your outdoor and recreational gear. Inside, you'll find generous living spaces and a layout designed for comfortable living. While some cosmetic updates could enhance the home's appeal, this is the perfect opportunity for buyers to add their own style and create a home that reflects their personal taste. Rather than paying a premium for someone else's renovations, you'll have the chance to customize the finishes you love while building equity in an established neighborhood where location truly matters. The real showstopper is the incredible community lifestyle. Residents enjoy exclusive access to a private beach, community pool, boat launch, and clubhouse, providing endless opportunities for boating, fishing, swimming, social gatherings, and enjoying the Chesapeake Bay. Imagine spending your weekends on the water, relaxing by the beach, or gathering with neighbors at community events, all just minutes from your front door. Whether you're looking for a primary residence, a place to grow, or an investment in one of Kent Island's most desirable communities, this home delivers exceptional value and endless potential. Homes with this combination of space, amenities, convenience, and opportunity are increasingly rare. Bring your vision, add your personal touch, and discover why so many people are choosing to call Stevensville and Kent Island home. Don't miss this chance to create something truly special while enjoying the waterfront lifestyle you've always wanted.

606 Old Love Point Rd, Stevensville

Listing courtesy of Thyme Real Estate Co LLC. Contact: 3026900245
$599,900
3 Beds ⋅ 4 Baths
Experience the best of Kent Island waterfront living in this beautifully appointed home located in the sought-after Bayside community of Chester. Designed for both everyday comfort and effortless entertaining, this residence features an open-concept floor plan with abundant natural light, spacious living areas, and stylish finishes throughout. The gourmet kitchen serves as the heart of the home, offering generous counter space, quality cabinetry, and a seamless flow into the dining and living areas. The expansive primary suite provides a private retreat with a walk-in closet and luxurious ensuite bath. Additional bedrooms and flexible living spaces offer plenty of room for guests, a home office, or recreation. Enjoy outdoor living from the private deck, perfect for relaxing and taking in the peaceful surroundings. An attached garage and ample storage add convenience to everyday life. Residents of Bayside enjoy exceptional community amenities, including a clubhouse, fitness center, swimming pool, tennis courts, walking trails, and marina access. The boat slips at Castle Marina are rented. It can be on a short term up to a yearly basis. There are some slips over on the side where Queens landing condos are that can be for sale. Ideally located near waterfront dining, shopping, golf courses, and major commuter routes, this home offers the perfect blend of Eastern Shore charm and modern convenience. Don't miss this opportunity to enjoy a resort-style lifestyle in one of Chester's premier waterfront communities. Additional parking spaces are located across the street for your convenience.

1012 Auckland Way, Chester

Listing courtesy of Redfin Corp. Contact: 3016586186
$435,000
3 Beds ⋅ 3 Baths
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
$799,000
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:

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

606 Kimberly Way, Stevensville

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

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

303 Creeks End Ln, Stevensville

Listing courtesy of Paul Wesley Real Estate. Contact: 7032822709
$485,000
4 Beds ⋅ 2 Baths
Lovely 4 bedroom rancher with big, fenced backyard on cul de sac in Stevensville neighborhood of Cloverfields on Kent Island. Community pool, beach, clubhouse, playground, and boat marina. Very large primary bedroom addition, big living room, large kitchen-dining combo area, nice outdoor deck off kitchen, two large outbuildings in backyard and plenty of room for garden, fire pit, volleyball etc.

15 Dixon Ct, Stevensville

Listing courtesy of Cottage Street Realty LLC. Contact:

$999,000
5 Beds ⋅ 5 Baths
Welcome to luxury coastal living in the highly desirable Four Seasons at Kent Island 55+ community in Chester. Built in 2025, this practically new home offers the perfect blend of elegance, comfort, and convenience — without the wait for new construction. Ideally situated on coveted Kingfisher Lane, this exceptional Tuscaloosa model offers over 3,200 square feet of beautifully designed living space with 5 bedrooms and 4.5 baths. The upgraded stone-and-shake exterior creates stunning curb appeal, while the covered front porch offers peaceful peek-a-boo water views — the perfect place to enjoy your morning coffee at sunrise. Inside, the open-concept main level showcases a thoughtfully upgraded interior with classic cabinetry, glass display cabinets, and professional-grade GE appliances in the kitchen. The spacious living area is anchored by a dramatic stone gas fireplace, while custom wall detailing and molding upgrades in the foyer and primary suite add warmth and sophistication throughout the home. Norman shutters on every window, upgraded carpet with premium padding, and carefully selected finishes elevate every room. The main-level primary suite offers a private retreat with elegant trim details and a spa-inspired en suite bath featuring a luxurious soaking tub designed for relaxation. Additional upgrades include a screened porch for outdoor enjoyment, epoxy garage flooring, painted garage walls, and a dedicated EV charging station for modern convenience. Located just a short distance from the community dog park, playground, pickleball and tennis courts, and the state-of-the-art clubhouse, this home offers not only exceptional design but also an unmatched lifestyle. Residents of Four Seasons at Kent Island enjoy resort-style amenities including indoor and outdoor pools, a fitness center, walking trails, social spaces, and activities designed to support an active and vibrant coastal lifestyle. All of this is ideally located just minutes from the Chesapeake Bay Bridge, offering convenient access to Washington and Baltimore, while also being close to shopping at the Queenstown Premium Outlets and an array of local waterfront dining and everyday conveniences.

233 Kingfisher Ln, Chester

Listing courtesy of Samson Properties. Contact: 7033788810
$559,900
2 Beds ⋅ 3 Baths
Experience "Paradise" in Queen’s Landing. This rare, end-unit waterfront gem offers an unparalleled living experience overlooking the serene Lake Amleto. Boasting a 2019 full-gut renovation by a custom contractor, this 1,425 sq. ft. residence (including a 145 sq. ft. sunroom) blends sophisticated design with resort-style tranquility. The interior showcases master-level craftsmanship: solid hickory wood floors, custom solid wood doors, custom maple cabinetry with ingenious storage solutions (toe-kick and spice & utensil drawers), and Calacatta Gold marble adorning both the kitchen and the gas fireplace surround. The open floor plan is optimized with structural improvements, including a pantry with a pocket door, a custom staircase with integrated storage, and a hidden Murphy door. Extensive recessed lighting on main floor with 3 dimmable picture wall accent lighting. Luxury finishes abound, from Emtek brass hardware and crown molding in every room to Monogram premium appliances and custom window treatments with a hidden railing system. Both upper-level bedrooms feature ensuites and are private retreats; one features a Travertine shower and floor with antique bronze hardware, while the other offers elegant Italian tile. Relax year-round in the sunroom, constructed with heavy-duty UV-protected glass, to watch herons and waterfowl against a backdrop of lake fountains. A remote-controlled full patio width awning installed to control the amount of sunlight coming into the home. Modern peace of mind is provided by an under- warranty Carrier HVAC system (with humidifier/air cleaner), Homeguard water softener, and updated roof, windows, and stucco. The Queen's Landing lifestyle includes a renovated clubhouse, heated outdoor pool, fitness center, pickleball and tennis, racquetball, community marina, kayak launch and racks. Unique Opportunity: The owner is also offering a 70-foot deep-water boat slip for separate purchase—a rare find for the avid mariner. Features List: • Renovation: Total gut-renovation (2019) including structural optimizations. • Kitchen: Custom Maple cabinetry, Calacatta Gold Marble counter tops and backsplash, Monogram/Blomberg appliances. • Mechanicals: Carrier HVAC w/ humidifier, Homeguard softener, LG HE Washer/Dryer. • Extra insulation in the attic with insulated access cover. Sound proofing insulation between the first and second floor was added during the remodel. • WellSys water dispenser: tied to home plumbing and includes cold and hot water. This is an optional rental unit and is contained within the kitchen cabinet. • Exterior: New Roof (2021), New Stucco (2017), New Windows/Front Door (2017). • Parking/Storage: Storage room off sunroom; ample community parking. • Boating: 70’ deep-water slip available.

29 Queen Mary Ct, Chester

Listing courtesy of Jorge A. Zea. Contact: 8555500528
$1,049,500
5 Beds ⋅ 5 Baths
Price Reduced $50K – Check out the Virtual Tour! Exceptional Value in Four Seasons at Kent Island Why wait to build? This less-than-one-year-old Tuscaloosa model on sought-after Kingfisher Lane delivers the upgrades, location, and efficiency buyers are chasing—without the timeline or added expense. Positioned just across from the Chester River, enjoy peekaboo water views from the covered front porch and even a sightline to the clubhouse. Inside, the home is bright, open, and thoughtfully designed with 5 bedrooms and 4.5 baths, offering flexibility for guests, work-from-home space, or multigenerational living. It shows like new—but lives better—because everything has already been elevated beyond builder grade. Over $70,000 in post-builder upgrades, including: • Owned solar system (10kW+) providing substantial energy savings • Custom closet systems throughout the home • Custom window treatments already installed • Premium Café Series appliances • Tankless water heater • Upgraded lighting and fixtures • Additional high-end finishes and improvements throughout The spacious floor plan offers room for everyone, while the oversized garage provides ample storage for vehicles, golf carts, and all the gear that comes with Eastern Shore living. Life in Four Seasons at Kent Island is about more than the home itself. Residents enjoy resort-style amenities including a stunning clubhouse, indoor and outdoor pools, fitness center, pickleball courts, walking trails, kayak launch, fishing pier, and an active social calendar designed for a vibrant lifestyle. With immediate availability, extensive upgrades already completed, and one of the community's most desirable locations, this home represents an opportunity that's becoming increasingly difficult to find. Add in the recent $50,000 price reduction, and this is one of the best values currently available in Four Seasons at Kent Island. Don't miss your chance to enjoy nearly new construction, energy-efficient living, and the Chesapeake Bay lifestyle you've been waiting for.

215 Kingfisher Ln, Chester

Listing courtesy of RE/MAX Executive. Contact: 4432741900
$525,000
3 Beds ⋅ 4 Baths
Save up to $320/month with a Lender Paid 1 Point Buy Down with accepted offer by 6/30/26 - Ask Lender for details! 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 $540,000. 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: 7033788810
$769,000
4 Beds ⋅ 3 Baths
Discover the charm of this beautifully renovated split-level home in the desirable Prospect Bay community. With 4 spacious bedrooms and 3 full baths, this residence boasts an inviting interior featuring upgraded countertops, LVP floors, and cozy exposed beams. The heart of the home is the combination kitchen/dining area, perfect for gatherings that can flow outside to the new expanded deck. With one bedroom, full bath and living room on lower level it could be the perfect in-law suite or college student apartment. Enjoy the serene 1.22-acre corner lot with firepit, trees perfect for hammock, backing to mature trees, offering a peaceful views. The community amenities include a pool, golf course, marina, community pool, tennis & pickleball courts and playgrounds, fostering a vibrant neighborhood spirit. Enjoy easy access to the Prospect Bay sanctuary for boating and fishing enthusiasts. Located in a friendly community with excellent schools and nearby parks, this home is perfect for those seeking comfort and convenience. BONUS: Outdoor Office with private entrance on back right corner of house. PLUS: Community has a few boat slips available for rent!

1 Bunker, Grasonville

Listing courtesy of Wilson Realty & Staging LLC. Contact: 4103042250
$259,900
2 Beds ⋅ 2 Baths
This charming two-bedroom, one-and-a-half-bath townhouse is designed for comfortable everyday living within a friendly, family-oriented community setting. A thoughtfully designed traditional floor plan showcases engineered flooring, carpeting, and ceramic tile in select areas, creating a warm interior. The well-appointed kitchen features coordinating appliances, including a dishwasher and microwave, offering both style and convenience for everyday living and entertaining. Main-floor laundry enhances the home’s effortless functionality. A designated location for a pellet stove is already in place, complete with chimney piping through the upper levels and roof. A one-time fee is required to obtain a boat slip. Slips are assigned by unit number and are available for use only after purchase by a unit owner. The current assigned slip is 17-2, located on the pier behind the pool. Enjoy a resort-style lifestyle with access to community amenities, including an in-ground pool and direct access to Thompson Creek, which flows into the Cox Creek—ideal for unlimited boating, fishing, and kayaking. The home also offers an attached garage, additional off-street parking, and an overflow guest lot for added convenience. Situated in a vibrant, well-maintained neighborhood residents benefit from the nearby parks, schools, and essential public services, this property delivers low-maintenance luxury. Association-managed common areas ensure a pristine setting, allowing residents to enjoy a carefree and elevated lifestyle.

17 Mariners Way Unit #17-2, Stevensville

Listing courtesy of Up-County Realty, Inc.. Contact:

$70,000
2 Beds ⋅ 1 Baths
HUGE PRICE DROP! Now is your time to buy that sweet summer spot! Welcome to your waterfront paradise in the highly sought-after Beach Harbor Camper Cooperative Inc. of Grasonville, MD! This Town and Country Park model ranch-style home is the perfect blend of comfort, convenience, and offers some inspiring views, making it the ultimate 3-season go to for the water and beach lovers! This incredible home boasts 1.5 bedrooms and one bathroom, perfect for weekend or monthly summer getaways. New vinyl flooring and fresh paint. Beautiful water views of the Jackson Creek and the majestic Chester River. Shed provides ample storage. Step outside onto the deck and enjoy your morning coffee or entertain for breakfast, lunch or dinner. Picture yourself lounging on the beach or embarking on thrilling adventures in your kayak or boat through the sprawling waterways of the area. If you're a paddle-boarder, the protected waters of the creek and river are an absolute dream! Indoors cool off with window air conditioners for personalized climate control. The "half bedroom" features 2 bunk beds and a window, while the primary bedroom offers ample space for a queen bed and includes a closet. Conveniently located just steps from the community beach, this community offers immediate access to a host of outdoor activities, from swimming and fishing to kayaking, paddleboarding, shuffleboard, basketball and tennis. The delightful community pool, hot tub and clubhouse provide the perfect place for social gatherings and community events. Don't let this opportunity slip away! Take the first step towards owning your slice of paradise in the Beach Harbor Camper Cooperative. Schedule a viewing today and prepare to experience the very best of waterfront living, all at an incredibly affordable price! Enjoy! (Monthly fee $350/Monthly or $4,200/Yearly

111 Beach Harbor F, Grasonville

Listing courtesy of HSA By The Bay. Contact: 4432504707
$1,275,000
3 Beds ⋅ 4 Baths
REDUCED PRICE ! Experience Exceptional Waterfront Living on the Chester River! A stunning 3000 sq ft townhome featuring 3 bedrooms, 3.5 bathrooms, a dedicated office AND a large bonus room - offering the perfect combination of comfort and flexibility. This was also one of the few "stretch" units- built wider to accommodate setbacks. The result was a wider Dining Room adding more natural light, wider decks, and more WATERVIEWS! Inside you'll find an open floor plan that's perfect for entertaining! It has hardwood floors, a dramatic floor to ceiling stone fireplace, a gourmet kitchen with high end newer stainless steel appliances & finishes, granite countertops, and ensuite bathrooms in all the bedrooms! Enjoy Beautiful Water Views from nearly every room thanks to thoughtfully designed architectural windows. Two covered decks with remote controlled screens invite you to relax and take in the breathtaking views over the Chester River. You also have a 2 car attached garage! Located in an exclusive gated community on a private peninsula, this home backs up to the renowned Safe Harbor Marina that offers a pool, fitness center, and over 600 slips, making it a boaters dream! Narrows Pointe is just around the corner from many great ( docking) restaurants, tiki bars, coffee and dessert spots! Golf enthusiasts will love being just 5 minutes from Queenstown Golf Links, close to other courses too! Outlet shopping is nearby for convenience. Only 20 minutes from Annapolis and Easton, 45 minutes from BWI Airport, 55 minutes from Washington, DC & Baltimore, and 1 1/2 hours away from Ocean City ! Whether you're looking for a year-round residence or a weekend retreat, this home offers the ultimate Chesapeake Bay lifestyle !

346 Narrows Pointe Dr, Grasonville

Listing courtesy of Berkshire Hathaway HomeServices Homesale Realty. Contact: 8003833535