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$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:

$1,700,000
7 Beds 6 Baths
Set on more than six private acres in one of Kent Island’s most desirable locations, this exceptional estate offers a rare blend of luxury, scale, and refined livability. Encompassing approximately 5,680 square feet, the residence has been thoughtfully elevated through extensive improvements, resulting in a truly turnkey offering in a setting defined by privacy, presence, and the freedom of no HOA restrictions, including the ability to keep livestock. At the heart of the home, a spectacular chef’s kitchen sets the tone for both everyday living and elevated entertaining. Custom cabinetry frames a suite of premium Viking and Miele appliances, complemented by an oversized refrigerator and freezer, multiple ovens, dual dishwashers, beverage refrigeration, a dedicated ice maker, and a walk-in pantry. This is a space designed to perform just as well for quiet evenings as it does for large gatherings. A soaring two-story family room anchors the main level, filled with natural light and centered around a newly installed pellet stove insert. The main-level primary suite serves as a private retreat, featuring a fully reimagined spa-inspired bath with a steam shower, soaking tub, and bespoke cabinetry. Across three finished levels, seven bedrooms provide remarkable flexibility for multi-generational living, guests, home offices, or creative pursuits. Throughout the home, refreshed interiors, custom built-ins, and thoughtful updates contribute to a cohesive sense of comfort and refinement. Outdoors, the property unfolds like a private resort. An expansive patio, gazebo, curated landscaping, and swimming pool create an effortless setting for entertaining or quiet relaxation. The surrounding acreage enhances the sense of seclusion, with space for recreation, gardening, livestock, or simply enjoying the quiet rhythm of estate living. The detached two-story garage extends the property’s versatility, with a dedicated fitness studio above and generous space below for vehicles, equipment, hobbies, or future expansion. What truly distinguishes the property is the quiet confidence of what has already been accomplished. Comprehensive improvements to core systems and infrastructure ensure a level of reliability and peace of mind rarely found in homes of this scale, allowing the next owner to simply arrive and enjoy. Despite its private and pastoral setting, the estate remains just minutes from Route 50, providing convenient access to Annapolis, Baltimore, Washington, D.C., and the Eastern Shore. Positioned near the highly regarded Matapeake school campus, it offers a rare combination of seclusion, accessibility, and everyday convenience. Rarely does a property combine acreage, scale, and refinement in such a complete way. This is more than a home. It is a private Kent Island estate designed for living well, entertaining effortlessly, and enjoying space without compromise.

102 Little Neck Rd, Stevensville

Listing courtesy of HomeSource Pro Real Estate. Contact: (443) 454-1470

$599,900
3 Beds 3 Baths
Recently Reduced and Ready for Its New Owner! Experience the best of Eastern Shore living at 1024 Avalon Court, where spacious design, natural light, and a peaceful setting come together beautifully. Perfectly positioned on a desirable lot with views of the community pond area and protected woodlands, this exceptional residence offers a wonderful blend of privacy, comfort, and everyday convenience. From the inviting exterior with stone accents and a two car garage to the open interior layout and exceptional outdoor living spaces, this home is designed for easy living and effortless entertaining. Step inside to a welcoming foyer with neutral paint and a bright, airy feel that continues throughout the main level. The thoughtfully designed floor plan offers excellent flexibility with formal living and dining areas, generous open gathering spaces, and seamless flow between rooms. Expansive windows bring in beautiful natural light while framing peaceful rear views, creating a warm and inviting atmosphere throughout the home. The heart of the home is the open concept kitchen and family room area, ideal for both everyday living and entertaining. The kitchen features abundant cabinetry, granite counters, stainless steel appliances, recessed lighting, a center island cooktop, and direct connection to the surrounding living spaces. The spacious family room offers a cozy fireplace and easy access to the private screened porch and large raised concrete patio, two standout features rarely found in this community. Both outdoor spaces overlook the community pond area and protected woodlands, creating a private and peaceful backdrop for relaxing, dining, and entertaining. The home continues with spacious bedrooms, including a large main level owner’s suite with generous closet space and a private bath featuring dual vanities, a soaking tub, and separate shower. This main level suite offers excellent flexibility for multigenerational living, guests, or those seeking everyday convenience. Additional bedrooms on the upper level provide comfortable space for family, guests, home office needs, hobbies, or recreation. Outdoor living is truly a highlight, with multiple areas to enjoy the serene wooded setting. The private screened porch is perfect for morning coffee, quiet evenings, or relaxing without the elements, while the oversized raised concrete patio offers wonderful space for grilling, entertaining, or simply enjoying the peaceful rear views. Additional highlights include flexible living spaces, a heated and air conditioned two car garage with amazing storage, and a peaceful rear setting rarely found in such a convenient location. Ideally positioned with easy access to major commuter routes including Routes 50 and 301, this exceptional residence offers convenient access to Downtown Annapolis, Washington, D.C., Baltimore, Kent Island, the Bay Bridge, Middletown, Dover, NSA, Fort Meade and Dover Air Force Base. Enjoy great local amenities including restaurants, shopping, recreation, and all the lifestyle conveniences that make the Eastern Shore so desirable. Don’t miss out on this incredible opportunity!

1024 Avalon Ct, Stevensville

Listing courtesy of Berkshire Hathaway HomeServices PenFed Realty. Contact:

$559,000
3 Beds 3 Baths
Welcome to this beautifully maintained 3-bedroom, 2.5-bathroom home in the Waterman’s Cove community in Chester. Nestled on a quiet street along scenic Cox Creek, this charming property offers the perfect blend of comfort, style, and convenience. An inviting front porch welcomes you home, while water views greet you upon arrival and can also be enjoyed from the spacious rear composite deck, built by Lundberg Builders, perfect for relaxing or entertaining. The home sits adjacent to community open space, offering added privacy with no direct neighbor next door. Inside, you’ll find hardwood flooring and an open-concept layout designed for modern living. The living room flows seamlessly into the dining area and kitchen, which features granite countertops, stainless steel appliances, and a beautiful tile backsplash. Sliding doors off the dining area lead to the composite deck and a lush, partially fenced yard, creating an ideal space for indoor-outdoor living. The kitchen also provides convenient interior access to the attached one-car garage. Upstairs, the primary suite offers a well-appointed bath, two additional bedrooms, a second full bath, and a laundry room for added convenience. Located just one mile from Route 50 on Cox Neck Road, this home offers quick access to shopping, dining, commuter routes to Washington DC and Baltimore, and the Chesapeake Bay Bridge. The intimate Waterman’s Cove community consists of just nine homes, with HOA services that include lawn care and trash removal - making for easy, low-maintenance living. Enjoy the peaceful lifestyle of Maryland’s Eastern Shore, with water views and privacy in a highly convenient location.

126 Watermans Cove Ln, Chester

Listing courtesy of Coldwell Banker Realty. Contact: 4102638686

$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

$4,158,000
9 Beds 8 Baths
Nestled within the prestigious Wolf Farm community, this exquisite residence offers a harmonious blend of luxury and comfort, perfect for those seeking an elevated lifestyle. This property is one of few on Kent Island that has unobstructed views of Annapolis, Baltimore and the Chesapeake Bay Bridge. Guests are welcomed with a gated circular drive adorn with stone pillars, lush flower beds and a professionally manicured lawn. The neoclassical architectural style mimics that of Thomas Jeffersons home Monticello. Spanning an impressive 10,152 square feet, the kitchen has been meticulously renovated in 2026, ensuring convenience of use while gazing at the Bay. Step inside to discover an open floor plan that invites natural light to dance across the stunning marble and luxury vinyl plank flooring. The eat-in kitchen and separate formal dining room provide ample space for entertaining, while the pantry ensures that all your culinary needs are met. The primary suite is a true sanctuary, boasting a bay-front view, a lavish primary bath, and expansive walk-in closets. Each of the nine bedrooms is designed with comfort in mind, offering generous space and thoughtful details. With eight full bathrooms, morning routines are a breeze, ensuring privacy and convenience for all. The heart of the home is complemented by three elegant fireplaces, creating cozy nooks for relaxation. Recessed lighting and upgraded countertops throughout add a touch of sophistication, while the wet/dry bar and custom wine cellar elevate your entertaining experience. Step outside to your personal oasis, where a stunning in-ground pool awaits, surrounded by multiple terraces and balconies that overlook the serene Chesapeake Bay. With 500 feet of waterfrontage, this property offers unparalleled access to the water, complete with a private composite dock that accommodates multiple slips for your boating adventures. Whether you enjoy power boating or kayaking, the navigable waters provide endless opportunities for exploration. Additional features include a full daylight basement with outside access, perfect for guests or recreational activities, and an attached side-entry garage with ample driveway space for up to 15 vehicles. This home is not just a residence; it's a lifestyle. Experience the tranquility of waterfront living combined with the luxury of modern amenities, all within the embrace of a warm and inviting atmosphere. Embrace the exclusive lifestyle that awaits you in this remarkable property.

319 Blue Bay Rd, Stevensville

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

$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

$719,000
3 Beds 3 Baths
GAME CHANGER--Qualified buyers may take advantage of a seller-paid 2-1 interest rate buydown with acceptable terms. This beauty is ready to WOW you & has a new lower price! From the moment you step inside your attention will be drawn to all the little details that make this property a show stopper... Wood beams on the soaring ceilings, huge center kitchen island with storage on both sides, gorgeous engineered flooring, screened porch built on a cement foundation not decking, shadow box detail and so much more. You'll appreciate the generous primary suite on one side and two additional bedrooms with full bath on the other side of the first floor. Multiple living spaces, cozy propane fireplace, laundry room off attached garage that will actually make you want to do the laundry! Upstairs is a nicely sized bonus room complete with a mini split perfect as a home office, family room or guest room. Sellers made a number of after construction upgrades. To put it simply, you will love everything about this home! Completely turnkey.

481 Eagle Manor Dr, Church Hill

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

$2,495,000
5 Beds 4 Baths
Price improvement. Welcome home to this stunning waterfront property in Cove Creek Club on Kent Island. Cove Creek is a Golfer's Paradise! This remarkable five bedroom, four bathroom home offers an unparalleled blend of privacy, elegance, and panoramic coastal beauty all located on your very own private peninsula. With an impressive 566 feet of protected shoreline where Tanner’s Creek converges with Cove Creek, opening directly to the Eastern Bay, this southern-facing residence offers breathtaking water views from nearly every room. Upon entering, you’re greeted by a dramatic two-story foyer with soaring vaulted and coffered ceilings that set an immediate tone of refinement, drawing the eye straight through to the large backyard and shimmering water views beyond. The thoughtfully designed main level features high ceilings throughout and a serene primary suite with views of the pool and waterfront. The primary retreat offers a custom walk-in closet with built-ins, tray ceiling, and a spa-inspired bath with dual vanities, private water closet, soaking tub, expansive walk-in shower, and plantation shutters for added privacy. Upstairs, enjoy a recreation room with wide angle water views and balcony perfect for enjoying sunsets while playing a game of pool or darts. Four additional bedrooms can be found here as well, two on either side of the home sharing jack-and-jill style bathrooms with private closets. Designed for effortless entertaining and elevated everyday living, the open-concept living and dining spaces flow seamlessly from the beautifully updated kitchen. Here, refined finishes include soft-close cabinetry, granite countertops, a marble backsplash, center island, walk-in pantry, stainless-steel appliances, gas cooktop, wine refrigerator, and warming drawer. The kitchen opens to an inviting living room with sliding doors to access the outdoor living area. Outside you’ll find extensive hardscaping with a built-in grill, granite countertops, and a granite dining table seating eight, perfect for hosting refined waterfront gatherings. The resort-style backyard is a private sanctuary, featuring a sparkling pool and a private pier equipped with three boat lifts—ideal for boating, paddle boarding, crabbing, or simply enjoying sunsets accompanied by visits from blue herons and bald eagles. Professionally designed landscaping offers year-round color with mature plantings all complemented by a lush, level lawn maintained by a multi-zone irrigation system. Additional highlights include a spacious three-car garage with room for vehicles, golf carts, and storage, along with premium finishes throughout that reflect timeless craftsmanship and meticulous attention to detail. As a resident of Cove Creek, enjoy access to an exceptional array of private amenities including a USGA-rated golf course, deep-water marina, private beach, clubhouse, fitness center, tennis, pickleball, and bocce courts, boat ramp and storage yard, as well as miles of scenic walking and biking trails - all located on Kent Island, just minutes from the Chesapeake Bay Bridge and Route 50.

137 Tanners Point Dr, Stevensville

Listing courtesy of Coldwell Banker Realty. Contact: 4102638686