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$609,990
2 Beds ⋅ 3 Baths
Welcome to the Magothy, a beautifully designed home offering 2 bedrooms, 2.5 baths, and a 1-car garage. This home blends modern comfort with functional living spaces. The main living area features a dry bar and an electric fireplace, creating a warm and inviting setting for everyday living and entertaining. The owner’s suite includes a private sitting room and large walk-in closets, offering a spacious and relaxing retreat. The kitchen is designed for both style and convenience, featuring a single oven, microwave, gas cooktop with range hood, dishwasher, pendant lighting, tile backsplash, and quartz countertops. Laminate flooring flows throughout the home, with tile flooring in both full baths. The owner’s bath is thoughtfully designed with a walk-in shower featuring a seat and handheld shower wand, double sinks, and quartz countertops for added comfort and functionality. For a full list of features for this home please contact our sales representatives. Photos are for illustrative purposes only and may not represent the exact home or finishes available.

102 Boatswain Way Unit #2912, Chester

Listing courtesy of Berkshire Hathaway HomeServices PenFed Realty - OP. Contact: 4102083500
$529,900
3 Beds ⋅ 3 Baths
Enjoy Chesapeake Bay breezes, amazing water views and sunsets! Why pay waterfront prices and taxes when you can enjoy the same coastal lifestyle just steps from the water? Built in 2025 and impeccably maintained, this beautifully upgraded 3 bedroom, 2.5 bath home backs directly to Kentmorr Marina, offering beautiful Bay and marina views along with the rare opportunity to enjoy one of Kent Island's most desirable waterfront communities. The open-concept floor plan features luxury vinyl plank flooring throughout the main level, quartz countertops, an oversized farmhouse sink, white shaker cabinetry with soft-close drawers and cabinets, Craftsman-style interior doors, black designer fixtures, framed mirrors, and a spacious primary suite with a beautifully tiled shower and double vanity. A composite rear deck with vinyl railings provides the perfect place to relax and enjoy the marina views, while fresh landscaping, raised garden beds, and an expanded asphalt driveway add to the home's exceptional curb appeal. Located on a quiet street with no through traffic, you'll love being just steps from the private community beach where breathtaking Chesapeake Bay sunsets become part of everyday life. Bring your boat! Kentmorr Marina is right outside your back door (contact the marina for slip availability and pricing) or take a short stroll to Channel Side Restaurant for waterfront dining, live music, sandy beach seating, and a lively tiki bar. The Kent Island South Trail, nearby kayak launches, fishing piers, and Blue Heron Golf Course offer even more opportunities to enjoy the outdoors. Why wait for new construction? This exceptional property offers something a new build can't: a truly established waterfront community where the marina, private beach, waterfront dining, and unforgettable sunsets are all just steps from your front door. Ideally situated just minutes from the Bay Bridge, you'll enjoy convenient access to the Western Shore while embracing the relaxed coastal lifestyle of Kent Island.

520 Chesapeake Ave, Stevensville

Listing courtesy of Samson Properties. Contact: 7033788810
$379,000
2 Beds ⋅ 1 Baths
Charming Cape Cod home offering both residential comfort and commercial potential, beautifully updated with modern finishes while maintaining its classic character. This move-in-ready property features 2 bedrooms, 1 full bathroom, an inviting sunroom entry, and luxury vinyl plank flooring throughout. The updated kitchen showcases stainless steel appliances, an induction range, new refrigerator, granite countertops, and refreshed cabinetry. Recent improvements include the bathroom, double-pane windows, roof, siding, HVAC system, well system, electrical panel, and front entry door. The property also features an oversized detached garage with side entry and a spacious asphalt driveway for added convenience. Minutes to Kent Island, close to major hwy. A rare opportunity to own a versatile property with endless possibilities!

3801 Main St, Grasonville

Listing courtesy of Fairfax Realty Select. Contact: 7035932381
$1,250,000
5 Beds ⋅ 3 Baths
Classic Colonial Overlooking the Golf Course in Prospect Bay. Welcome to this beautifully maintained brick-front Colonial, perfectly positioned with picturesque golf course views in the sought-after Prospect Bay community. Filled with natural light from oversized windows, the open floor plan offers the perfect balance of comfortable everyday living and elegant spaces for entertaining. The home features four spacious bedrooms upstairs, plus a first-floor office or optional fifth bedroom, making it ideal for guests, multi-generational living, or working from home. Hardwood floors, two fireplaces, a formal dining room, and generously sized living spaces create timeless appeal throughout. The spacious primary suite offers a peaceful retreat with a walk-in closet and private bath. A three-car garage provides ample storage and convenience. Step outside to your private backyard oasis, where a heated swimming pool, expansive deck with a covered awning, and sweeping golf course views create the perfect setting for relaxing or entertaining. Enjoy watching golfers from your backyard while soaking in the peaceful surroundings. Living in Prospect Bay means enjoying resort-style amenities, including an 18-hole championship golf course, clubhouse with members-only restaurant and bar, marina with boat launch, swimming pool, tennis and pickleball courts, playground, and a full calendar of year-round social events. This exceptional home offers the perfect blend of classic elegance, modern comfort, and an unbeatable lifestyle.

4 Prospect Bay Dr W, Grasonville

Listing courtesy of Coldwell Banker Realty. Contact: 4102638686
$989,800
5 Beds ⋅ 4 Baths
Coastal luxury living by Laine Street Homes, this exceptional waterfront home offers over 3,000 square feet on 3 levels with 5 bedrooms, 3.5 bathrooms, and stunning water views. Perfectly positioned and thoughtfully designed to capture beautiful sunrises over the water, the home is filled with natural light and showcases panoramic water views from the main living areas and the luxurious primary suite. Designed for both luxury living and entertaining, the open floor plan features 7-inch wide plank flooring, a gas fireplace, entry-level guest suite, and high-end finishes throughout. The gourmet kitchen is the heart of the home, complete with shaker-style cabinetry, quartz countertops, an oversized island, premium ZLINE stainless steel appliances, upgraded custom lighting, and expansive water views. Upstairs, the spacious primary suite offers a peaceful waterfront retreat with a spa-inspired bath featuring a 6-foot tiled walk-in shower with dual shower heads, a built-in bench, double vanities, and generous closet space. Bedroom-level laundry and beautifully finished bathrooms with tile flooring add everyday convenience. Outdoor living is just as impressive, with an expansive rear deck and covered patio overlooking the creek—perfect for enjoying sunrises over the water or relaxing while watching local wildlife. Adding to the sense of privacy, approximately 181 acres of rural land zoned "Countryside District" stretch across the shoreline on the opposite side, preserving the natural views with protected land. For those who enjoy life on the water, this location is hard to beat. Launch a kayak, paddleboard, or small boat from your backyard and reach the Chester River in approximately one mile, with the Chesapeake Bay just 5 to 6 water miles beyond. Enjoy quick access to bay boating while returning home to the calm waters, privacy, and natural beauty of a protected creek. Combining quality craftsmanship, upscale finishes, and an exceptional waterfront setting, this newly completed home offers a rare opportunity to enjoy the best of Maryland's Eastern Shore lifestyle!

203 Riverside Dr, Chester

Listing courtesy of Long & Foster Real Estate, Inc.. Contact: 3019459010
$929,990
2 Beds ⋅ 3 Baths
Welcome to the Chester, a thoughtfully designed home offering 2 bedrooms, 2.5 baths, and a 1-car garage. Scheduled for settlement in December 2026, this home combines modern comfort with functional and stylish living spaces. The main living area features a dry bar and an electric fireplace, creating a warm and inviting atmosphere perfect for both relaxing and entertaining. A dedicated home office with lited French doors provides a private and elegant workspace. The kitchen is designed for both everyday living and convenience, featuring a single oven, microwave, gas cooktop with range hood, dishwasher, pendant lighting, tile backsplash, and quartz countertops. Luxury vinyl plank flooring flows throughout the home, with tile flooring in both full baths. The owner’s bath offers a walk-in shower with a seat and handheld shower wand, double sinks, and quartz countertops, creating a comfortable and functional retreat. For a full list of features for this home please contact our sales representatives. Photos are for illustrative purposes only and may not represent the exact home or finishes available.

102 Boatswain Way Unit #2943, Chester

Listing courtesy of Berkshire Hathaway HomeServices PenFed Realty - OP. Contact: 4102083500
$829,990
2 Beds ⋅ 3 Baths
Welcome to the Chester, a thoughtfully designed home offering 2 bedrooms, 2.5 baths, and a 1-car garage. Scheduled for settlement in December 2026, this home combines modern comfort with functional and stylish living spaces. The main living area features a dry bar and an electric fireplace, creating a warm and inviting atmosphere perfect for both relaxing and entertaining. A dedicated home office with lited French doors provides a private and elegant workspace. The kitchen is designed for both everyday living and convenience, featuring a single oven, microwave, gas cooktop with range hood, dishwasher, pendant lighting, tile backsplash, and quartz countertops. Luxury vinyl plank flooring flows throughout the home, with tile flooring in both full baths. The owner’s bath offers a walk-in shower with a seat and handheld shower wand, double sinks, and quartz countertops, creating a comfortable and functional retreat. For a full list of features for this home please contact our sales representatives. Photos are for illustrative purposes only and may not represent the exact home or finishes available.

102 Boatswain Way Unit #2932, Chester

Listing courtesy of Berkshire Hathaway HomeServices PenFed Realty - OP. Contact: 4102083500
$345,000
3 Beds ⋅ 2 Baths
Welcome to 1609 Crab Alley Drive, a charming three-bedroom, one-and-a-half-bath rancher offering comfortable one-level living and lovely water views. Inside, hardwood flooring adds warmth and character, while the oversized picture window fills the front living room with natural light. The spacious backyard is made for summertime enjoyment, featuring an above-ground pool with plenty of additional room for entertaining, gardening, pets, or play. A large detached two-car garage provides exceptional space for vehicles, storage, hobbies, or a workshop. With its classic curb appeal, generous outdoor space, and convenient Chester location, this inviting home is ready for its next chapter.

1609 Crab Alley Dr, Chester

Listing courtesy of Paul Wesley Real Estate. Contact: 7032822709
$349,000
3 Beds ⋅ 2 Baths
Welcome to easy, one-level living in a location that truly gives you the best of both worlds! Just minutes from the charm and downtown, walkable, waterfront lifestyle of Chestertown, yet tucked within the highly sought-after Queen Anne’s County School District, this beautifully updated 3-bedroom, 2-bath home is ready to impress. Step inside to find a spacious, open feel highlighted by a massive living room—perfect for gathering, relaxing, and entertaining. The heart of the home is the stunning, renovated kitchen, offering plenty of space to cook, host, and make everyday living feel a little more special. Both bathrooms have been tastefully updated, giving the home a fresh, modern feel throughout. Enjoy the ease of all one-level living, along with a screened-in porch that’s perfect for morning coffee, evening unwinding, or hosting friends without the bugs. Outside, you’ll love the great yard—ideal for play, pets, or simply enjoying the peaceful setting. Need extra space? The large detached 2-car garage offers plenty of room for vehicles, storage, hobbies, or a workshop setup. This water-oriented community offers private access to the Chester River just a couple of blocks away—perfect for kayaking, fishing, or soaking in those Eastern Shore sunsets. There’s also a voluntary property owners association at just $30/year if you’d like to participate. If you’ve been looking for space, updates, and that relaxed Eastern Shore lifestyle—all in a convenient location—this one checks all the boxes!

123 Heath Rd, Chestertown

Listing courtesy of Chesapeake Real Estate Associates, LLC. Contact:

$2,850,000
5 Beds ⋅ 5 Baths
Set on Forty Five picturesque acres of prime agricultural land with extensive tillable acreage, this exceptional Five bedroom, Four and one half bath brick colonial blends timeless design with modern versatility and waterfront charm. Privately situated on a quiet cove just off the mouth of the Chester River, the property offers a rare combination of space, functionality, and lifestyle appeal. Inside, the home features a thoughtfully designed layout ideal for both everyday living and entertaining. A main-level en-suite provides excellent flexibility for multi-generational living or private guest quarters, while an additional upper-level en-suite enhances comfort and convenience for visitors. The spacious primary suite serves as a true retreat, complemented by well-proportioned secondary bedrooms and multiple full baths. Refined living spaces include a formal dining room, a dedicated home office perfect for remote work, and an inviting screened porch overlooking the water—an ideal setting to relax and take in the tranquil views. The nearly fully finished basement expands your living options with generous space for recreation, hobbies, or a workshop. Recent upgrades—including a new roof and septic system—offering peace of mind, while the 2-zone HVAC system ensures efficient year-round comfort. Outdoors, enjoy the in-ground pool surrounded by a patio, perfect for entertaining or unwinding, along with open acreage that offers endless possibilities for farming, equestrian use, or a private rural lifestyle. Complete with a Twocar garage and located in a highly desirable waterfront setting, this property presents a rare opportunity to own a versatile estate that balances luxury living, scenic beauty, and agricultural potential.

1810 Love Point Rd, Stevensville

Listing courtesy of Monument Sotheby's International Realty. Contact: (410) 525-5435
$999,990
3 Beds ⋅ 3 Baths
Welcome to the Severn, a beautifully designed home offering 3 bedrooms, 2.5 baths, and a 1-car garage. Scheduled for settlement in October 2026, this home blends modern comfort with functional living spaces. The main living area features a dry bar and an electric fireplace, creating a warm and inviting setting for everyday living and entertaining. The owner’s suite includes a private sitting room and large walk-in closets, offering a spacious and relaxing retreat. The kitchen is designed for both style and convenience, featuring a single oven, microwave, gas cooktop with range hood, dishwasher, pendant lighting, tile backsplash, and quartz countertops. Laminate flooring flows throughout the home, with tile flooring in both full baths. The owner’s bath is thoughtfully designed with a walk-in shower featuring a seat and handheld shower wand, double sinks, and quartz countertops for added comfort and functionality. For a full list of features for this home please contact our sales representatives. Photos are for illustrative purposes only and may not represent the exact home or finishes available.

110 Boatswain Way Unit #3044, Chester

Listing courtesy of Berkshire Hathaway HomeServices PenFed Realty - OP. Contact: 4102083500
$629,990
2 Beds ⋅ 3 Baths
Welcome to the Magothy, a beautifully designed home offering 2 bedrooms, 2.5 baths, and a 1-car garage. This home blends modern comfort with functional living spaces. The main living area features a dry bar and an electric fireplace, creating a warm and inviting setting for everyday living and entertaining. The owner’s suite includes a private sitting room and large walk-in closets, offering a spacious and relaxing retreat. The kitchen is designed for both style and convenience, featuring a single oven, microwave, gas cooktop with range hood, dishwasher, pendant lighting, tile backsplash, and quartz countertops. Laminate flooring flows throughout the home, with tile flooring in both full baths. The owner’s bath is thoughtfully designed with a walk-in shower featuring a seat and handheld shower wand, double sinks, and quartz countertops for added comfort and functionality. For a full list of features for this home please contact our sales representatives. Photos are for illustrative purposes only and may not represent the exact home or finishes available.

102 Boatswain Way Unit #2911, Chester

Listing courtesy of Berkshire Hathaway HomeServices PenFed Realty - OP. Contact: 4102083500
$675,000
4 Beds ⋅ 3 Baths
Welcome to 144 Wye Knot Road, where peaceful country living meets everyday convenience. Nestled on 3 private, level acres, this spacious cape cod offers the perfect blend of comfort, functionality, and open space, all within easy reach of Easton, Annapolis, the Bay Bridge, and major commuter routes. A tree-lined paved driveway welcomes you home, while the classic exterior, complete with a full front porch, dormer accents, and an attached side-load two-car garage, creates timeless curb appeal. Inside, you'll find over 2,200 square feet of thoughtfully designed living space featuring four bedrooms, two-and-a-half bathrooms, and an ideal floor plan for both everyday living and entertaining. Formal living and dining rooms flank the welcoming foyer, while the rear of the home opens to a dramatic family room with soaring cathedral ceilings, abundant natural light, rich wood flooring, and a cozy gas fireplace. The kitchen serves as the heart of the home, offering Corian countertops, stainless steel appliances, a center island, generous cabinetry, and an informal dining area overlooking the backyard. Step outside to the spacious deck, perfect for morning coffee, summer barbecues, or simply relaxing while taking in the peaceful surroundings. Upstairs, you'll find four generously sized bedrooms, including a spacious primary suite. The finished bonus room above the garage provides exceptional flexibility and is ideal for a recreation room, home office, fitness room, playroom, or 4th bedroom/2nd primary suite. Additional features include dual-zone HVAC (replaced within the last 10 years), a tankless gas water heater (replaced within the last 10 years) and an EV charger-ready garage. The true highlight of this property is the land. Level, usable acreage like this is increasingly difficult to find and provides endless opportunities for gardening, recreation, entertaining, future outdoor amenities, or simply enjoying the peace, privacy, and beauty of country living. If you've been searching for a home that offers room to breathe without sacrificing convenience, 144 Wye Knot Road is an exceptional opportunity to enjoy the best of Maryland's Eastern Shore lifestyle.

144 Wye Knot Rd, Queenstown

Listing courtesy of RE/MAX Leading Edge. Contact:

$829,990
2 Beds ⋅ 3 Baths
Welcome to the Chester, a thoughtfully designed home offering 2 bedrooms, 2.5 baths, and a 1-car garage. Scheduled for settlement in December 2026, this home combines modern comfort with functional and stylish living spaces. The main living area features a dry bar and an electric fireplace, creating a warm and inviting atmosphere perfect for both relaxing and entertaining. A dedicated home office with lited French doors provides a private and elegant workspace. The kitchen is designed for both everyday living and convenience, featuring a single oven, microwave, gas cooktop with range hood, dishwasher, pendant lighting, tile backsplash, and quartz countertops. Luxury vinyl plank flooring flows throughout the home, with tile flooring in both full baths. The owner’s bath offers a walk-in shower with a seat and handheld shower wand, double sinks, and quartz countertops, creating a comfortable and functional retreat. For a full list of features for this home please contact our sales representatives. Photos are for illustrative purposes only and may not represent the exact home or finishes available.

102 Boatswain Way Unit #2933, Chester

Listing courtesy of Berkshire Hathaway HomeServices PenFed Realty - OP. Contact: 4102083500
$749,990
2 Beds ⋅ 3 Baths
Welcome to the Chester, a thoughtfully designed home offering 2 bedrooms, 2.5 baths, and a 1-car garage. Scheduled for settlement in October 2026, this home combines modern comfort with functional living spaces. The heart of the home features a dry bar and an electric fireplace, creating a warm and inviting atmosphere. A dedicated home office with lited French doors provides a stylish and private workspace. The kitchen is designed for both everyday living and entertaining, featuring a single oven, microwave, gas cooktop with range hood, dishwasher, pendant lighting, tile backsplash, and quartz countertops. Luxury vinyl plank flooring flows throughout the home, with tile flooring in both full baths. The owner’s bath offers a walk-in shower with seat and handheld shower wand, double sinks, and quartz countertops for added convenience and style. For a full list of features for this home, please contact our sales representatives. Photos are for illustrative purposes only and may not represent the exact home or finishes available.

110 Boatswain Way Unit #3042, Chester

Listing courtesy of Berkshire Hathaway HomeServices PenFed Realty - OP. Contact: 4102083500
$1,500,000
4 Beds ⋅ 3 Baths
Waterfront on the Corsica River—opportunities like this don't come along every day! Proudly positioned on a spectacular 2-acre lot with approximately 540 feet of shoreline, this exceptional 4-bedroom, 3-bath home offers breathtaking panoramic views and an unmatched waterfront lifestyle. Located at the end of a quiet cul-de-sac in the established community of Corsica Landing Estates, just outside Centreville town limits, you'll enjoy the benefits of no town taxes or HOA fees. Mature landscaping and thoughtfully designed hardscaping create a private setting that perfectly complements the expansive river views. Designed for entertaining, the backyard is truly a waterfront oasis. Enjoy the in-ground concrete pool with diving board, a spacious hot tub housed in its own versatile room for year-round enjoyment, and a 145-foot private dock with approximately 6 feet of mean low water, complete with electric, water, two boat lifts, and a floating dock. Whether you prefer relaxing in the sun or unwinding in the shade, the beautifully landscaped outdoor living spaces have something for everyone, including an expansive 47.5' x 18' Trex deck with two pergola-like covered cooking and dining areas and a spacious waterside patio. Inside, the home offers comfortable living with generous spaces throughout. The eat-in kitchen features granite countertops, stainless steel appliances, including a new oversized refrigerator, and a separate wet bar with wine refrigerator and wine rack. The main level also includes a spacious living room with a wood-burning fireplace, an oversized formal dining room, a home office with custom built-ins and a large bay window, a full bath, and a convenient laundry/mudroom. One of the home's standout features is the incredible waterside sunroom, filled with natural light from walls of windows and offering spectacular views of the pool and river. Complete with a beautiful stone propane fireplace and ceiling fans, it's the perfect place to relax in every season. The spacious primary suite includes hardwood flooring, a walk-in closet, dual vanities, a walk-in shower, and direct access to a large 18.5' x 24' bonus room above the garage. With its own private staircase from the attached two-car garage, this flexible space is ideal for a guest suite, recreation room, fitness area, studio, or additional home office. Next to the garage is an attached exterior storage/utility room which provides even more convenience. THE FINISHED LIVING AREA SQUARE FOOTAGE FOR THIS HOME IS LARGER THAN THE ASSESSMENT OFFICE REPRESENTS AND THE GOOGLE SATELLITE IMAGE MAP DOES NOT REFLECT ALL OF THE PROPERTY. PLEASE SEE DEEDS AND MAPS ATTACHED IN THE DOCUMENTS. Numerous updates have been completed over the years, including the HVAC system and ductwork, roof, triple-pane windows and sunroom doors with a lifetime warranty. The pool was renovated in 2016, with a new pool pump and skimmer pipe installed in 2023 and a new pool motor in 2026. The well pump was replaced and lowered in 2007, offering additional peace of mind. Whether you're searching for a full-time waterfront residence, the ultimate family gathering place, or a home designed for entertaining, this remarkable property delivers. With boating, fishing, kayaking, swimming, and unforgettable sunsets right from your backyard—and a county boat ramp, playground, and pavilion just minutes away—there's still plenty of summer left to enjoy. Schedule your private tour today and experience everything this extraordinary Corsica River property has to offer. Located within an hour to Baltimore, Washington, DC or Delaware. Stay Tuned For Professional Photos Coming Soon !

405 Quail Run Dr, Centreville

Listing courtesy of Benson & Mangold, LLC. Contact: (443) 988-0483
$549,900
4 Beds ⋅ 3 Baths
Professional Photos coming soon. TWO LOTS FOR SALE with two different tax Ids/addresses. The home sits on 1.16 arces and the additional adjacent lot sits on 1.10 acres which was graded as a Par 3 golf course. The second lots tax ID is 1805020174, address is 165 Greenwood Creek Rd, Queenstown, MD 21658. This house is ready for your own personal touches, with four bedrooms and 2.5 baths sitting on 2.16 lush acres of privacy. This homes offers a mature landscaped yard with WATERVIEWS! Hardwood floors throughout just waiting to be brought back to their original beauty. This home also features a full In-law suite / guest house. Located in Queenstown, with easy commutes to Annapolis, Washington, Baltimore, Delaware and the beaches. Come see this home and make it your own today!

161 Greenwood Creek Rd, Queenstown

Listing courtesy of Chesapeake Real Estate Associates, LLC. Contact:

$535,000
5 Beds ⋅ 3 Baths
Welcome to 205 Anchor Lane, a spacious and versatile home in the desirable Castle Marina community of Chester! Situated on a generous half-acre lot with no HOA, this oversized split foyer offers the flexibility, space, and location that today's buyers are looking for. 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: 7033788810
$619,900
4 Beds ⋅ 3 Baths
Welcome home to this spacious and inviting 4-bedroom, 2.5-bath Colonial located in the sought-after community of Mallard Run, with easy access to the nearby bike trail. With an open floor plan and plenty of room to spread out, this home offers the perfect blend of comfort and convenience. The kitchen is truly the heart of the home, featuring granite countertops, a center island, and new stainless steel appliances, all flowing seamlessly into the main living areas. Just off the kitchen, the large sunroom provides the perfect spot to relax, entertain, or enjoy your morning coffee. Beautiful bamboo flooring adds warmth and character throughout much of the home, while the pellet stove creates a cozy atmosphere during the cooler months. A first-floor laundry room adds everyday convenience. Upstairs, the spacious primary suite offers a walk-in closet and a private bath with double vanities. Three additional bedrooms provide plenty of space for family, guests, or a home office. Step outside to enjoy the composite deck and patio, ideal for summer cookouts and outdoor gatherings. There is even an existing pad for you to bring your hot tub! Additional updates include a roof that's approximately 6 years old and an HVAC system that's approximately 4 years old. If you've been looking for a well-maintained home in a desirable neighborhood with room to live, work, and entertain, this one is not to be missed.

324 Web Foot Ln, Stevensville

Listing courtesy of Rosendale Realty. Contact: 4107580333
$490,000
2 Beds ⋅ 3 Baths
Welcome to 1000 Herons Nest Way #23, an exceptional former model home located in the first phase of condominiums within the highly desirable Four Seasons at Kent Island. This beautiful 2-bedroom, 2.5-bath residence combines designer finishes, thoughtful upgrades, and a peaceful natural setting to create the perfect low-maintenance retreat. From the moment you enter, you'll appreciate the bright, open floor plan, gorgeous luxury vinyl plank flooring, and the seamless flow between the kitchen, dining, and living spaces—ideal for entertaining while still offering comfortable, defined living areas. The gourmet kitchen opens effortlessly into the main living space, while the dedicated home office features custom built-in cabinetry, display shelving, and accent lighting, creating an inviting workspace or library. Throughout the home you'll find quality upgrades including plantation shutters in both bedrooms, custom closet organization systems, ceiling fans, and a built-in wireless audio system with a Samsung Frame TV, blending everyday comfort with modern convenience. The spacious primary suite offers a relaxing escape, while the thoughtfully designed split-bedroom layout provides privacy for overnight guests. One of this home's most captivating features is the private balcony overlooking protected wooded surroundings, where you'll enjoy peaceful mornings with coffee while watching deer, birds, and the abundant wildlife that make Kent Island so special. Just outside your door, enjoy convenient access to the Cross Island Trail, nearby Macum Creek, and community kayak storage—perfect for embracing the Eastern Shore lifestyle. Residents of Four Seasons at Kent Island enjoy a truly carefree lifestyle with exterior maintenance, landscaping, and common areas maintained by the HOA, making it easy to lock the door and travel without worry. Resort-style amenities include a stunning clubhouse, indoor and outdoor pools, fitness center, pickleball and tennis courts, walking trails, and an active calendar of clubs and social events. Beautifully upgraded, impeccably maintained, and ideally situated, this former model home offers a rare opportunity to enjoy resort-style living surrounded by the natural beauty of Kent Island.

1000 Herons Nest Way Unit #23, Chester

Listing courtesy of Samson Properties. Contact: 7033788810
$415,000
3 Beds ⋅ 2 Baths
Just Reduced.... Welcome to 624 Romancoke Road on Kent Island. This beautiful 3 bedroom, 2 full bath Rancher is move in ready and awaiting it's next owner. Situated on a large lot with easy 2 minute access to the Chesapeake Bay Bridge, and easy commute to Annapolis, DC and Baltimore. No worrying about a private well or septic, this home is on public water and sewer. Fully renovated in 2016 with HVAC, appliances and roof in 2017, recent updates include the crawl space encapsulation 2025, additional attic insulation 2025, new windows 2024, front door and rear sliding door 2025 and the rear deck refurbished 2023. Located in the Bay City community that includes a boat ramp and pavilion, and a 2nd park located on the Chesapeake Bay with a tot lot. The feel of this home is bright and welcoming and the fenced rear yard allows for plenty of room for a future garage or pool. Take a tour of this home that will be available for a quick settlement.

624 Romancoke Rd, Stevensville

Listing courtesy of RE/MAX Executive. Contact: 4432741900
$355,000
3 Beds ⋅ 3 Baths
Adorable is the perfect word to describe this beautifully maintained townhome! Freshly painted and featuring a new roof and skylights (2025), this inviting home offers over 1,600 square feet of comfortable living space with three bedrooms, two full baths, and one-half bath. The main level showcases vaulted ceilings with skylights that fill the home with natural light, creating a bright and airy atmosphere. The open-air plan seamlessly connects the spacious living room and dining area, with room to comfortably accommodate four to six guests, making it ideal for both everyday living and entertaining. Step outside to the private porch overlooking a picturesque pond, where you can relax and enjoy the peaceful sound of the fountain. The main-level primary suite offers a walk-in closet, walk-in shower, and private access to the porch—your own tranquil retreat. The bright, open kitchen features abundant windows and space for a cozy breakfast table, creating the perfect spot to enjoy your morning coffee while taking in the views. Additional highlights include a one-car garage, convenient storage space off the porch, and low HOA fees compared to most communities. Ideally located just minutes from shopping, restaurants, churches, the Bay Bridge, and everyday conveniences, this charming townhome offers the perfect combination of comfort, style, and convenience. Don't miss the opportunity to make this wonderful home your own!

7013 Bridgepointe Dr, Chester

Listing courtesy of Coldwell Banker Realty. Contact: kelly.thompson@cbmove.com
$749,000
3 Beds ⋅ 2 Baths
Coastal cottage charm meets waterfront living on picturesque Crab Alley Creek. Offering 120 feet of shoreline and direct access to the Eastern Bay, this beautifully maintained home combines privacy, convenience, and the very best of the Chesapeake lifestyle. A pier permit already in hand provides an exciting opportunity for the next owner to further enhance their waterfront experience. This move-in-ready residence features 3 bedrooms, 2 full baths, and a versatile bonus room that can serve as a home office, guest room, or potential 4th bedroom. Meticulously updated and lovingly maintained throughout, pride of ownership is evident at every turn. Thoughtful upgrades create a warm and inviting atmosphere, including under-cabinet lighting and dimmer switches throughout the home, allowing you to create the perfect ambiance for any occasion. The kitchen is both stylish and functional, featuring an additional beverage refrigerator, making entertaining family and friends a breeze. The bathrooms offer a touch of luxury with heated floors and built-in Bluetooth speakers, creating a spa-like retreat within your own home. Situated on a large, level waterfront lot, the property is designed for both relaxation and recreation. Across the creek, protected conservation land provides a peaceful, natural backdrop and exceptional privacy rarely found on the water. Raised garden beds offer the opportunity to grow your own herbs and vegetables, while the detached garage, two storage sheds, and attic provide ample space for tools, equipment, seasonal items, and all your waterfront essentials. Spend your evenings gathered around the fire pit overlooking the water, launch a kayak from your backyard, or cruise to one of the many waterfront restaurants accessible from the Eastern Bay. Whether you're entertaining guests or enjoying a quiet sunset, this property embraces the laid-back charm of coastal living. Conveniently located just 10 minutes from the Bay Bridge, 20 minutes from Annapolis, and approximately 90 minutes from the beach, you'll enjoy easy access to everything while feeling worlds away. A rare opportunity to own a turnkey waterfront retreat in one of Kent Island's most desirable locations, where every detail has been thoughtfully curated for comfort, convenience, and enjoyment.

205 Riverside Dr, Chester

Listing courtesy of Engel & Volkers Annapolis. Contact: (443) 292-6767
$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:

$569,900
4 Beds ⋅ 3 Baths
PRICE IMPROVEMENT! $10K REDUCTION! Why wait for new construction when this barely lived-in home in the desirable community of Perry’s Retreat is available now? Welcome to 128 Perry’s Retreat Boulevard, offering a bright, open-concept main level with LVP flooring throughout and a layout designed for everyday living and easy entertaining. The spacious kitchen features an oversized island, stainless steel appliances, pantry, quartz countertops, soft-close cabinetry, and plenty of room to gather. The main level also includes a convenient half bathroom, office space, garage access, an oversized coat closet, and a walkout to the spacious backyard. Upstairs, you’ll find four carpeted bedrooms, two full bathrooms, and a conveniently located laundry area. The beautiful primary suite features a tray ceiling, spacious walk-in closet with natural light, and an upgraded en-suite bathroom with LVP flooring, a dual vanity, and a shower with built-in seating and dual showerheads. Outside, enjoy a covered front porch with space for seating, a spacious backyard, and a maintenance-free vinyl privacy fence. Perry’s Retreat offers sidewalks throughout the community, playgrounds, and additional parking for boats, RVs, and extra vehicles. The location is another major bonus, with quick access to Route 50 and close proximity to Kent Island, the Narrows, Annapolis, Easton, St. Michaels, local dining, shopping, golf, boat launches, and Chesapeake Bay favorites. This move-in ready home offers the benefits of newer construction, a convenient Eastern Shore location, and no wait!

128 Perrys Retreat Blvd, Grasonville

Listing courtesy of RE/MAX Executive. Contact:

$446,950
3 Beds ⋅ 3 Baths
Open House August 15th, 1-3 pm. Be the first in to visit this property. A Rare Opportunity in a much sought after community. The ideal townhome in a waterfront community with Dock and slips across the street. Queenstown Harbor Golf in your Backyard. Walkable to Historic Queenstown. Just 15 minutes to the Bay Bridge. An easy commute to Annapolis. This home has been lovingly maintained. Very Private. A Pellet Stove in Family Room keeps you toasty in the Winter.

136 Long Dr, Queenstown

Listing courtesy of Coldwell Banker Realty. Contact: 4102638686
$575,555
4 Beds ⋅ 3 Baths
Discover the perfect blend of coastal living and everyday comfort in this spacious 4-bedroom, 3-bath single-family home located in the lovely area of Stevensville. Set on a generous 0.39-acre private fully fenced in lot. Ideal for those who enjoy entertaining, recreation, gardening or simply rest and relaxation with the Chesapeake Bay in your own backyard. Inside, you’ll find a bright and welcoming flexible floorplan layout featuring multiple living areas, a well-appointed kitchen, a beautifully decorated, spacious and bright morning room and much more. A home suited for families or multi-generational living. Recent updates include energy-efficient windows, a french drain around the home, modern appliances, improved insulation, upgraded water systems, and refreshed finishes, providing peace of mind and added comfort. The spacious backyard offers endless possibilities—gardening, play areas, or outdoor gatherings—while the property’s ample parking, carport/garage, and room for boat storage make it a standout for those who love life on the water. Just a short distance from your own neighborhood private beach, nearby marinas and restaurants. This home delivers coastal charm on the Eastern Shore. Conveniently located near Route 50...Come and visit us! A rare opportunity you don't want to miss to own in one of Kent Island’s most sought out water-access neighborhoods.

511 Chesapeake Ave, Stevensville

Listing courtesy of RE/MAX Realty Centre, 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
$4,995,000
5 Beds ⋅ 5 Baths
Architect-designed contemporary waterfront home on nearly 18 private acres across two parcels with approximately 1,400 feet of shoreline on Greenwood Creek. Positioned to capture 180-degree western views, the property offers privacy, deep water, and a setting that is increasingly difficult to find on Maryland’s Eastern Shore. A custom pivoting front door creates a striking first impression and sets the tone for the home's thoughtful design. The home was designed to take advantage of the surrounding water and landscape, with floor-to-ceiling windows, open gathering spaces, and strong indoor-outdoor connections throughout. The kitchen opens to the main living areas and features a glass accordion door that connects directly to the screened porch, creating a seamless transition between indoor and outdoor spaces. The layout flows easily between the kitchen, dining areas, family room, porch, and pool area, making the home equally well suited for everyday living and entertaining. The primary suite is set apart from the rest of the home by a glass-enclosed walkway and includes a private office, large dressing room, en-suite bath, and private porch access. In addition to the primary suite, the main level includes three additional bedrooms, each with access to a private bathroom. The finished lower level includes a home theater, billiards room, bar area, workout room, additional bedroom and full bathroom, along with unfinished basement space for storage. Outdoor features include a solar-heated pool, private beach, and deep-water pier with two boat lifts. The protected shoreline and direct access to Eastern Bay make this an ideal property for boating and waterfront living. A three-bay outbuilding with workshop space and additional storage provides room for equipment, hobbies, or car and boat storage. Located just outside Queenstown, the property is convenient to Easton, Annapolis, Washington D.C., Baltimore, and Philadelphia while offering the privacy and pace of the Eastern Shore.

2800 Bennett Point Rd, Queenstown

Listing courtesy of TTR Sotheby's International Realty. Contact: 4106733344
$499,000
4 Beds ⋅ 3 Baths
Welcome to 336 Timber Lane—a beautifully maintained Colonial offering the space, comfort, and lifestyle today's buyers are looking for, all in a convenient Grasonville location just minutes from Kent Island and the Bay Bridge. With over 2,100 square feet, this move-in ready home features 4 bedrooms, 2.5 baths, hardwood flooring, a cozy fireplace, and a spacious, flowing floor plan designed for everyday living and effortless entertaining. The bright kitchen overlooks the family room, creating the perfect gathering place for holidays, game nights, or simply spending time together. Upstairs, the spacious primary suite offers a peaceful retreat with a walk-in closet and private en-suite bath, while three additional bedrooms provide flexibility for family, guests, a home office, or fitness space. Step outside and enjoy a generous backyard with plenty of room for entertaining, gardening, play, or simply relaxing after a day on the water. One of Grasonville's best-kept secrets is the lifestyle. You'll enjoy quick access to marinas, waterfront restaurants, boating, fishing, shopping, and Route 50—all while experiencing less congestion than many neighboring communities. Best of all, this home offers an incredible opportunity to enjoy the Eastern Shore lifestyle while getting more home for your investment than many comparable properties on Kent Island. Whether you're commuting, raising a family, or looking for a place to enjoy everything the Chesapeake Bay has to offer, 336 Timber Lane delivers the perfect blend of space, value, and location.

336 Timber Ln, Grasonville

Listing courtesy of Samson Properties. Contact: 7033788810