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$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
$420,000
3 Beds ⋅ 3 Baths
Save up to $269/month with a Lender Paid 1 Point Buy Down with an accepted offer by 6/30/26 - ask Lender for Details! Come Check Out the Views of Crab Alley! Welcome to 200 Newtown Road, a charming home perfectly suited for those looking to enjoy Eastern Shore living. The inviting front porch offers the perfect spot to relax and unwind, while the screened porch provides additional space to enjoy the outdoors in comfort. Inside, you’ll find a generously sized kitchen with room for a table for six, ideal for everyday living and entertaining. A sliding door leads to the fenced backyard, offering both convenience and privacy. Enjoy peaceful water views and the freedom of no HOA restrictions. Located just around the corner from Public Landing, this home is perfect for those who love being on the water—bring your boat and take advantage of nearby access. With 3 bedrooms, 2.5 bathrooms, and a price of $445,000, this home offers an excellent opportunity to own near the water in a desirable location.

200 Newtown Rd, Chester

Listing courtesy of Samson Properties. Contact: 7033788810
$672,800
4 Beds ⋅ 3 Baths
One of our most popular designs, the Doral offers formal and informal living areas with lots of room for the whole family to spread out. Your main level features a dining/den/flex space as well as a spacious family room and kitchen, breakfast area that flows to the spacious family room.. Add a light-filled morning room off the rear or expand your space with plan extensions. . Upstairs accommodates four nicely sized bedrooms, including aprimary suite with a massive closet area. and you can customize your lower level rec area to suit your needs. Located just a short walk to the waterfront, the community features a boat launch, pavillion, playground, and bayfront recreational area. Move in ready with versatile living spaces and a thoughtful layout.

323 Chenowith Dr, Stevensville

Listing courtesy of Keller Williams Flagship. Contact:

$699,800
4 Beds ⋅ 3 Baths
One of our most popular designs, The New Doral offers formal and informal living areas with lots of room for the whole family to spread out. Your main level features a dining/den/flex space as well as a spacious family room and kitchen, breakfast area that flows to the spacious family room.. Add a light-filled morning room off the rear or expand your space with plan extensions. . Upstairs accommodates four nicely sized bedrooms, including aprimary suite with a massive closet area. and you can customize your lower level rec area to suit your needs. There is a community beach, a pool and rental slips for the boat. Additionally, there is a playground and tot lot. A great place to claim the Eastern Shore Way of Life. As part of the Cloverfield Home Association, residents enjoy an array of community amentities that elevate the lifestyle: a sparkling pool for summer fun, a private community beach where you can dip your toes in the sand, a playground and tot lot, a marina that has boat rental slips available, and additiaonl recreational spaces that make this neighborhood one of the most sought after on the Eastern Shore. With an easy commute to anywhere on the Eastern Shore, as well as quick access to Annapolis and even Washington DC. This location blends convenience with coastal charm.

233 Nichols Manor Dr, Stevensville

Listing courtesy of Keller Williams Flagship. Contact:

$1,195,000
4 Beds ⋅ 5 Baths
Located in the prestigious Southwind community, a penisula between Crab Alley Bay & Cox Creek, this elegant contemporary ranch-style home offers an unparalleled lifestyle of luxury and comfort. Spanning over 4,400 sq. ft. of finished space, the interior boasts elegant marble flooring, complemented by crown moldings and built-ins that enhance its sophisticated charm. The gourmet kitchen, featuring upgraded countertops and a spacious island, flows seamlessly into the family room, perfect for entertaining. Relax in the primary suite with a lavish bath or unwind in the inviting family room by the fireplace with views out to Crab Alley. Three additional bedrooms (or two bedrooms and an office) and two baths round out the main level that offers sweeping scenic views from every vantage point. Step outside to discover a private oasis on 1.25 acres, complete with extensive hardscaping, a heated in-ground pool, and a soothing hot tub. Enjoy picturesque water views out the front and back, with access for kayaking and boating. The community amenities, including a beach, clubhouse, and tennis courts, elevate your living experience. This home is not just a residence; it's a lifestyle waiting to be embraced and enjoyed. Start living your best 'Shore Life' at 2855 Cox Neck Rd.

2855 Cox Neck Rd, Chester

Listing courtesy of Wilson Realty & Staging LLC. Contact: 4103042250
$337,500
3 Beds ⋅ 2 Baths
Motivated Seller!!! Loan is assumable for a qualified veteran. Opportunity to own a beautiful rancher on 0.46 ac in the town of Crumpton. This home was built in 2021. It has been maintained, and kept meticulously. It compares nicely to new construction. The front porch welcomes you to a well-designed open concept 3 BR, 2 full bathrooms home. Natural light illuminates the living space. There is no shortage of amenities: an updated, modern kitchen with SS appliances, under cabinet lighting, granite countertops, whole house sprinkler system. The laundry room adjoins the kitchen. This home offers plenty of room for all of your outdoor activities. It's two blocks to the boat ramp (Chester River). Easy commute to Route 301, Chestertown, Middletown, and the Bay Bridge. This is a one of a kind listing. Don't wait. Schedule your showings today!

209 3rd St, Crumpton

Listing courtesy of EXP Realty, LLC. Contact: 8885434829
$399,000
3 Beds ⋅ 4 Baths
REDUCED! Just like NEW! Welcome Home to this beautifully upgraded 4BR END UNIT Townhome with 2 full and 2 half baths, thoughtfully renovated from top to bottom! Step inside to find the main level that boasts NEW carpet and new LVP flooring, a NEW half bath, NEW paint, a spacious laundry room and a large bedroom that could be used as another family room, toy/game room, den space, home office and more! Get ready to be wowed by the rich walnut NEWLY stained hardwood flooring throughout the 2nd level where the living room, gas fireplace, NEW half bath and kitchen are located. The BRAND-NEW Kitchen finishes are sure to please with NEW white quartz counter tops, NEW SS Appliances, fresh neutral paint and white cabinetry! Upstairs hosts the huge Primary En-Suite, 2 more bedrooms all with NEW Carpet and another full bathroom with NEWLY Tiled shower, NEW toilet and NEW quartz sink! With three generous levels, a deck overlooking the pond, a cozy patio and a charming front porch, there’s space for everyone to relax and have their own space! Pull right into your own garage and your own driveway which makes life easy not to have to look for parking! The community offers fantastic amenities to enjoy like the inground and life-guarded pool, volleyball & tennis courts, fitness gym and direct access to the Cross Island Trail! Very close to the Castle Harbor Marina, many Beaches, Parks & Playgrounds and just a short stroll to local restaurants along the waters edge of the CHESTER RIVER! Condo living made easy with the Bayside fee covering major exterior maintenance including the roof, deck rails, siding, exterior structural upkeep, landscaping, snow removal, road maintenance, trash, master insurance policy, professional property management, long term reserve funding and the list goes on! Truly turn‑key living in an unbeatable location on the desired Eastern Shore of Maryland! Come see what Kent Island living is all about! SUMMER is here!

208 Blenny Ln, Chester

Listing courtesy of RE/MAX Executive. Contact: 4432741900
$2,375,000
4 Beds ⋅ 4 Baths
Welcome to Sunset Wharf, a refined waterfront enclave set within the picturesque Bay Bridge Marina, where coastal living is defined by sweeping views and effortless sophistication. This fully completed residence is one of just a select offering within the initial collection of three buildings, each thoughtfully designed with only two residences each, creating an intimate and private setting along the water’s edge. Inside, the home unfolds across three levels with a thoughtfully designed four bedroom, four bath layout that offers both flexibility and comfort. A private bedroom and full bath on the entry level provide the perfect space for guests or a quiet home office. The main living level is designed for seamless everyday living and entertaining, highlighted by a warm and inviting living room with a gas fireplace that adds both comfort and ambiance. The upper level features two additional bedroom suites, including a serene primary retreat complete with its own gas fireplace. An elegant touch that enhances the sense of relaxation and retreat. Expansive windows frame captivating views over the marina and out to the Chesapeake Bay, filling the home with natural light and creating an ever-changing backdrop of boating activity and open water. As the day winds down, the setting truly comes to life with breathtaking sunsets that paint the sky and reflect across the water. An experience to be enjoyed from both the interior living spaces and outdoor areas. High-end finishes and a modern, open-concept design elevate the interiors, while the beautifully appointed gourmet kitchen and well designed baths enhance both form and function. Every detail has been curated to deliver a low-maintenance, lock-and-go lifestyle without compromising on luxury. Ideally positioned within walking distance to waterfront dining, including Libbey’s Coastal Kitchen & Cocktails and Knoxie’s Table, residents also enjoy immediate access to marina amenities, scenic walking paths, and the relaxed rhythm of life on the Bay. Sunset Wharf offers a rare opportunity to own a newly completed residence in a thoughtfully designed waterfront community where every day feels like a getaway. Welcome Home!

115 Petrie Way, Stevensville

Listing courtesy of TTR Sotheby's International Realty. Contact: (410) 280-5600
$2,375,000
4 Beds ⋅ 4 Baths
Welcome to Sunset Wharf, a refined waterfront enclave set within the picturesque Bay Bridge Marina, where coastal living is defined by sweeping views and effortless sophistication. This fully completed residence is one of just a select offering within the initial collection of three buildings, each thoughtfully designed with only two residences each, creating an intimate and private setting along the water’s edge. Inside, the home unfolds across three levels with a thoughtfully designed four bedroom, four bath layout that offers both flexibility and comfort. A private bedroom and full bath on the entry level provide the perfect space for guests or a quiet home office. The main living level is designed for seamless everyday living and entertaining, highlighted by a warm and inviting living room with a gas fireplace that adds both comfort and ambiance. The upper level features two additional bedroom suites, including a serene primary retreat complete with its own gas fireplace. An elegant touch that enhances the sense of relaxation and retreat. Expansive windows frame captivating views over the marina and out to the Chesapeake Bay, filling the home with natural light and creating an ever-changing backdrop of boating activity and open water. As the day winds down, the setting truly comes to life with breathtaking sunsets that paint the sky and reflect across the water. An experience to be enjoyed from both the interior living spaces and outdoor areas. High-end finishes and a modern, open-concept design elevate the interiors, while the beautifully appointed gourmet kitchen and well designed baths enhance both form and function. Every detail has been curated to deliver a low-maintenance, lock-and-go lifestyle without compromising on luxury. Ideally positioned within walking distance to waterfront dining, including Libbey’s Coastal Kitchen & Cocktails and Knoxie’s Table, residents also enjoy immediate access to marina amenities, scenic walking paths, and the relaxed rhythm of life on the Bay. Sunset Wharf offers a rare opportunity to own a newly completed residence in a thoughtfully designed waterfront community where every day feels like a getaway. Welcome Home!

119 Petrie Way, Stevensville

Listing courtesy of TTR Sotheby's International Realty. Contact: (410) 280-5600
$2,375,000
4 Beds ⋅ 4 Baths
Welcome to Sunset Wharf, a refined waterfront enclave set within the picturesque Bay Bridge Marina, where coastal living is defined by sweeping views and effortless sophistication. This fully completed residence is one of just a select offering within the initial collection of three buildings, each thoughtfully designed with only two residences each, creating an intimate and private setting along the water’s edge. Inside, the home unfolds across three levels with a thoughtfully designed four bedroom, four bath layout that offers both flexibility and comfort. A private bedroom and full bath on the entry level provide the perfect space for guests or a quiet home office. The main living level is designed for seamless everyday living and entertaining, highlighted by a warm and inviting living room with a gas fireplace that adds both comfort and ambiance. The upper level features two additional bedroom suites, including a serene primary retreat complete with its own gas fireplace. An elegant touch that enhances the sense of relaxation and retreat. Expansive windows frame captivating views over the marina and out to the Chesapeake Bay, filling the home with natural light and creating an ever-changing backdrop of boating activity and open water. As the day winds down, the setting truly comes to life with breathtaking sunsets that paint the sky and reflect across the water. An experience to be enjoyed from both the interior living spaces and outdoor areas. High-end finishes and a modern, open-concept design elevate the interiors, while the beautifully appointed gourmet kitchen and well designed baths enhance both form and function. Every detail has been curated to deliver a low-maintenance, lock-and-go lifestyle without compromising on luxury. Ideally positioned within walking distance to waterfront dining, including Libbey’s Coastal Kitchen & Cocktails and Knoxie’s Table, residents also enjoy immediate access to marina amenities, scenic walking paths, and the relaxed rhythm of life on the Bay. Sunset Wharf offers a rare opportunity to own a newly completed residence in a thoughtfully designed waterfront community where every day feels like a getaway. Welcome Home!

123 Petrie Way, Stevensville

Listing courtesy of TTR Sotheby's International Realty. Contact: (410) 280-5600
$2,375,000
4 Beds ⋅ 4 Baths
Welcome to Sunset Wharf, a refined waterfront enclave set within the picturesque Bay Bridge Marina, where coastal living is defined by sweeping views and effortless sophistication. This fully completed residence is one of just a select offering within the initial collection of three buildings, each thoughtfully designed with only two residences each, creating an intimate and private setting along the water’s edge. Inside, the home unfolds across three levels with a thoughtfully designed four bedroom, four bath layout that offers both flexibility and comfort. A private bedroom and full bath on the entry level provide the perfect space for guests or a quiet home office. The main living level is designed for seamless everyday living and entertaining, highlighted by a warm and inviting living room with a gas fireplace that adds both comfort and ambiance. The upper level features two additional bedroom suites, including a serene primary retreat complete with its own gas fireplace. An elegant touch that enhances the sense of relaxation and retreat. Expansive windows frame captivating views over the marina and out to the Chesapeake Bay, filling the home with natural light and creating an ever-changing backdrop of boating activity and open water. As the day winds down, the setting truly comes to life with breathtaking sunsets that paint the sky and reflect across the water. An experience to be enjoyed from both the interior living spaces and outdoor areas. High-end finishes and a modern, open-concept design elevate the interiors, while the beautifully appointed gourmet kitchen and well designed baths enhance both form and function. Every detail has been curated to deliver a low-maintenance, lock-and-go lifestyle without compromising on luxury. Ideally positioned within walking distance to waterfront dining, including Libbey’s Coastal Kitchen & Cocktails and Knoxie’s Table, residents also enjoy immediate access to marina amenities, scenic walking paths, and the relaxed rhythm of life on the Bay. Sunset Wharf offers a rare opportunity to own a newly completed residence in a thoughtfully designed waterfront community where every day feels like a getaway. Welcome Home!

107 Petrie Way, Stevensville

Listing courtesy of TTR Sotheby's International Realty. Contact: (410) 280-5600
$680,000
3 Beds ⋅ 3 Baths
A rare blend of coastal proximity and refined living unfolds within this beautifully appointed corner residence in the sought-after 55+ waterfront community of Four Seasons at Kent Island. Built in 2024 and impeccably maintained , this like-new residence offers the comfort of immediate enjoinment without the wait for new construction. Positioned near a tranquil creek leading to the Chesapeake Bay, the home offers a lifestyle deeply connected to the water without the demands of direct waterfront ownership. Sunlight fills the open-concept layout through the residence’s desirable corner positioning, highlighting soaring ceilings, luxury vinyl plank flooring, and thoughtfully selected finishes throughout. The gourmet kitchen flows seamlessly into the dining and living areas, creating an inviting space for both quiet evenings and entertaining. Just beyond, a private balcony offers peaceful green surroundings with subtle water views, extending the home’s living space into a serene outdoor setting. The spacious primary suite serves as a private retreat with walk-in closets and a beautifully finished en-suite bath, while two additional bedrooms provide flexibility for guests, hobbies, or a home office. Residents of Four Seasons at Kent Island enjoy access to resort-style amenities including indoor and outdoor pools, fitness center, clubhouse spaces, pickleball and tennis courts, scenic walking trails, kayak launch, and fishing pier. Conveniently located near Kent Narrows, Annapolis, and Route 50, this exceptional residence offers a refined Eastern Shore lifestyle with easy access to dining, recreation, and waterfront experiences.

111 Marshgrass Way Unit #21, Chester

Listing courtesy of Samson Properties. Contact: 2406308689
$300,000
22.49 wooded acres on Romancoke Rd in Queen Anne’s County, MD, located 8 miles south of Stevensville. Features include mature pines, trail system, strong deer and turkey presence, and extensive road frontage thru two separate entrance pts. Close to Chesapeake Bay boat access and less than 8 miles to the Bay Bridge. Property has not been perc tested; all uses subject to buyer due diligence. Schedule an appointment for a private tour.

Romancoke Rd, Stevensville

Listing courtesy of Whitetail Properties Real Estate, LLC. Contact:

$365,000
3 Beds ⋅ 2 Baths
Practically brand new and just 2 years young with access to the Chester River, this beautifully maintained home is perfectly situated in a desirable water-oriented community—offering the best of Eastern Shore living! Located in the Queen Anne’s County school district and just minutes from downtown Chestertown, you’ll love the convenience paired with the peaceful setting. Enjoy easy access to the Chester River—you can drive your boat to the community ramp at the end of the street, or even take a nice short walk down to the water, to spend your days crabbing, fishing, kayaking, or simply soaking in the waterfront lifestyle. Inside, this 3-bedroom, 2 full bath home features durable and stylish LVP flooring throughout and a thoughtfully designed split floor plan. The spacious primary suite is privately situated on one side of the home and offers a walk-in shower, dual vanity, and a beautifully appointed bath. On the opposite side, you’ll find two additional bedrooms and a full bath with a tub/shower combo—ideal for guests or flexible living. The kitchen and living room are centrally located, creating an inviting and functional space for everyday living and entertaining. A standout bonus—an unfinished upstairs area of 544 additional SF, already in place and ready for your vision! Use it for storage now or finish it off for additional bedrooms, a home office, or recreation space. Step outside and enjoy both a charming front porch—perfect for morning coffee—and a massive back deck ideal for entertaining, grilling, or simply relaxing while taking in the peaceful surroundings. The generously sized yard with mature trees offers both privacy and room to enjoy the outdoors. Even more exciting—the county has indicated plans to pave the road in the near future. Added perk: fiber optic Talkie Internet is already available at the property, making working from home or streaming a breeze. Move-in ready, full of potential, and located in a charming waterfront community—this one checks all the boxes!

240 Merganser Dr, Chestertown

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

$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
$4,700,000
6 Beds ⋅ 6 Baths
Welcome to 200 Wye Road, an exceptional waterfront estate set on over two private acres along the Wye River, directly across from the protected natural beauty of Wye Island. Here, scale, setting, and thoughtful design converge to create a truly elevated Eastern Shore lifestyle. Spanning more than 8,100 square feet across three finished levels, the residence offers a refined yet highly livable floor plan designed to capture water views from nearly every room. Expansive living spaces, a formal dining room with handpainted custom wallpaper from the U.K., and a reimagined gourmet kitchen create an environment equally suited for everyday living and large-scale entertaining. The kitchen has been thoughtfully redesigned with updated cabinetry, statement lighting, and a full suite of premium appliances, including Wolf, Sub-Zero, and Bosch. The home offers exceptional flexibility, including an optional first-floor primary suite, a dedicated home gym, two laundry rooms, and an oversized mudroom designed for seamless day-to-day living. Two wood-burning fireplaces add warmth and character, enhancing the home’s sense of comfort and timeless appeal. The primary suite serves as a private retreat, complete with two walk-in closets and a fully renovated, spa-inspired bath featuring heated flooring, a soaking tub, a glass-enclosed shower, and its own gas fireplace, delivering a level of comfort and detail rarely found. Since 2024, the property has undergone extensive upgrades that enhance both performance and long-term value, including a new Owens Corning roof with a transferable warranty, three fully replaced Trane HVAC systems, a whole-home water filtration system, and comprehensive renovations throughout the bathrooms and interior spaces. Outdoor living is where the property truly distinguishes itself. A newly renovated 20x40 waterfront pool with a pebble finish and automatic cover anchors the setting, complemented by expansive hardscaping, manicured grounds, and multiple areas designed for entertaining or quiet relaxation. The shoreline has been improved with 250 feet of stone rip rap, and the deep-water dock is outfitted with new electrical service and lighting, featuring a new 25,000 lb boat lift and a 12,000 lb one along with two additional slips, providing effortless access to the Wye River and beyond. Whether enjoying sunrise coffee on the screened porch, hosting summer gatherings by the pool, or heading out by boat to St. Michaels or the Kent Narrows, this property offers a lifestyle defined by ease, privacy, and connection to the water. Conveniently located in Queenstown, just minutes from shopping, dining, and Route 50, with easy access to Annapolis and Easton, 200 Wye Road represents a rare opportunity to own a turnkey waterfront estate in one of the Eastern Shore’s most sought-after settings.

200 Wye Rd, Queenstown

Listing courtesy of TTR Sotheby's International Realty. Contact: (410) 280-5600
$639,000
3 Beds ⋅ 3 Baths
Beautifully updated home in sought-after Claiborne Fields a peaceful setting just outside of downtown Centreville, offering 3 bedrooms and 3 baths on a picturesque 1.5-acre lot. This exceptional property features a stunning outdoor setting with an in-ground saltwater pool, surrounded by Trex decking, a decorative vinyl fence, and an additional electric invisible dog fence—perfect for relaxing or entertaining—along with a detached 2-car garage>> The fully renovated first floor (2023) showcases new luxury vinyl plank flooring and a gourmet kitchen equipped with Matte Black Smart GE Café appliances, including an induction Glide Touch cooktop, single wall oven with True European convection, built-in convection/smart microwave, beverage and wine center, and BEST Cattura downdraft. A convenient 16" round bar sink is perfectly positioned in the beverage center nook for easy entertaining. The primary suite offers hardwood floors and a spa tub, creating a true retreat. Additional interior features include new carpet, an interior custom-built dog kennel, with Dutch door and dedicated shower room, and a propane fireplace added during the 2023 renovation. A generator, located in the detached garage, provides added peace of mind. Energy-efficient upgrades include a 2026 energy audit, encapsulated crawl space, attic insulation, air-sealed attic, and a commercial-grade dehumidifier. Anderson windows and Hunter Douglas blinds enhance both comfort and style. Numerous updates include a 2019 Black Stainless refrigerator and dishwasher, resealed driveway, new pool liner, and conversion to a saltwater pool (2021), making this home truly move-in ready. See estimated Square Footage Floor Plans Photos of Square footage is approximate and not guaranteed. Listing information, including total square footage and floor plans, are estimates and subject to buyer verification. Ideally located close to downtown Centreville and convenient to Rt. 301 for easy access to Kent Island ,Annapolis, Ocean City, and Delaware.

108 Claiborne Fields Dr, Centreville

Listing courtesy of Coldwell Banker Realty. Contact: kelly.thompson@cbmove.com
$424,000
3 Beds ⋅ 3 Baths
Cloverfields - This 3 bedroom 2 1/2 bath home is move in ready and updated with new carpet, paint, vinyl flooring, new bathroom cabinets and kitchen. The community offer pool, beach, boat ramp, play area and community club house. This is the perfect home to have just in time for summer and use all the community benefits.

729 Davol Rd, Stevensville

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

$569,900
2 Beds ⋅ 2 Baths
Welcome to easy, elevated living in the sought-after 55+ community of Bay Bridge Cove. From the moment you arrive, the private courtyard entry creates a warm and inviting first impression, offering a peaceful space to begin and end your day. Inside, you’ll find beautiful hardwood flooring throughout and a bright, open layout designed for both comfort and connection. The kitchen is the heart of the home, featuring a spacious center island, granite countertops, stainless steel appliances, and crisp white cabinetry that feels both timeless and fresh. The living area is filled with natural light and anchored by a cozy gas fireplace, creating the perfect space to relax or gather with friends. Just beyond, the sunroom truly shines, offering stunning views of the pond and fountain and a serene setting to enjoy your morning coffee or unwind in the evening. With western exposure, you’ll be treated to gorgeous sunset views that make this home feel extra special. The primary suite offers a peaceful retreat with a tray ceiling, generous closet space, and a comfortable, private feel. A second bedroom and full bath provide flexibility for guests, hobbies, or a home office. Bay Bridge Cove offers a vibrant, low-maintenance lifestyle with amenities including a clubhouse, outdoor pool, fitness center, billiards room, and beautifully maintained common grounds. Lawn care, snow removal, and community management are all taken care of, allowing you to focus on enjoying each day. Ideally located with easy access to shopping, Route 50, and the Bay Bridge, this home offers the perfect blend of convenience and tranquility. Opportunities like this, especially with pond views and sunset exposure, are rare within the community. Come see how effortlessly this beautiful home fits into your next chapter.Some photos are virtually staged.

845 Moorings Cir Unit #138, Stevensville

Listing courtesy of Coldwell Banker Realty. Contact: kelly.thompson@cbmove.com
$579,999
2 Beds ⋅ 3 Baths
Tucked away in a peaceful community on the Chesapeake Bay, this 2 bedroom, 2.5 bathroom townhouse with a loft offers the perfect mix of comfort, charm, and bay living. Situated on a desirable corner lot, the home features beautiful hardwood floors, a spacious kitchen with plenty of room to cook and gather, and a cozy fireplace that makes the living space feel warm and inviting on a winter day. **Boat Slip Included & Dredging has been started!** Step outside onto the large deck and take in the views — the perfect spot for morning coffee or relaxing evenings by the Bay. The loft adds extra flexible space for a home office, guest area, or additional lounge space. Residents also enjoy access to a private community pool, making it easy to enjoy everything this lifestyle has to offer.

118 Bayview, Grasonville

Listing courtesy of LPT Realty, LLC. Contact: 8773662213
$629,900
4 Beds ⋅ 3 Baths
Repositioned to reflect today’s market and offering exceptional value! This beautifully maintained custom-built home in the desirable Eagle Manor community combines luxury finishes, thoughtful design, and over an acre of professionally landscaped privacy. Inside, you’ll find an open and airy floor plan featuring 4 bedrooms, 3 full baths, luxury vinyl plank flooring, custom moldings, shiplap accents, two fireplaces, and abundant natural light. The gourmet kitchen is designed for gathering with quartz countertops, a large center island, farmhouse sink, stainless steel appliances, and ample cabinetry. The first-floor primary suite offers a private retreat with a spacious walk-in closet, soaking tub, and walk-in shower. Generous secondary bedrooms and flexible living spaces provide room for guests, a home office, or multigenerational living. Step outside to enjoy your own backyard oasis featuring an oversized screened porch, professionally landscaped grounds, mature privacy plantings, a serene koi pond, irrigation system, and elegant wrought iron fencing. The expansive one-acre lot also offers plenty of room for a future pool. With more than $140,000 in seller improvements, this move-in-ready home offers exceptional quality and value that would be difficult to replicate at today’s construction costs. Conveniently located near Centreville, Chestertown, waterfront marinas, shopping, dining, and the Chesapeake Bay, this is an outstanding opportunity to enjoy the best of Maryland’s Eastern Shore. Schedule your private showing today and experience everything 403 Eagle Manor has to offer.

403 Eagle Manor Dr, Church Hill

Listing courtesy of Coldwell Banker Realty. Contact: 4438562211
$850,000
4 Beds ⋅ 3 Baths
This charming ranch-style home in the desirable Prospect Bay community offers a perfect blend of comfort and elegance. With 4 spacious bedrooms and 3 full baths, the traditional floor plan features a cozy family room off the gourmet kitchen, ideal for gatherings. Enjoy upgraded countertops and a pantry, complemented by modern stainless steel appliances and huge center island. The large 3 Season room offers great flex space and views of the course. Enjoy the benefits of a tankless hot water, too! Step outside to a serene 1.01-acre lot with a rear yard, perfect for outdoor activities. The expansive deck invites you to relax while taking in stunning views of the nearby golf course. Community amenities include a refreshing pool and easy access to Prospect Bay, where you can enjoy canoeing, kayaking, and fishing. Conveniently located less than 10 miles from the airport, this home also boasts an oversized attached garage and ample driveway parking. Experience the warmth of this inviting residence, where every detail is designed for comfort and enjoyment.

5 Prospect Bay Dr W, Grasonville

Listing courtesy of Wilson Realty & Staging LLC. Contact: 4103042250
$569,000
5 Beds ⋅ 3 Baths
Nestled in a peaceful country setting in Queenstown, Maryland, this spacious 5-bedroom, 2.5-bath Colonial offers the perfect blend of privacy, comfort, and room to grow. Located in the heart of Queen Anne's County on Maryland's Eastern Shore, this beautiful home combines the tranquility of country living with the convenience today's buyers are searching for. Designed with everyday living and entertaining in mind, the home features generous living spaces filled with natural light. The large kitchen provides plenty of room for meal preparation and gathering with family and friends, while the adjoining family room with a cozy fireplace creates a warm and inviting atmosphere. Just off the family room, the screened-in porch offers the perfect space for outdoor dining, morning coffee, or relaxing while enjoying peaceful country views. The main level includes a versatile fifth bedroom, making it ideal for guests, multigenerational living, a private home office, or a flex space to fit your lifestyle. Upstairs, you'll find a spacious primary suite with an ensuite bath, along with three additional generously sized bedrooms and a newly renovated full bathroom. A finished bonus room over the two-car garage provides even more flexible living space—perfect for a home office, playroom, media room, home gym, or recreation area. Step outside to a fully fenced backyard that's ideal for pets, children, and outdoor entertaining. Backing to open farmland with no homes behind, the property offers exceptional privacy and scenic views rarely found in today's market. Additional highlights include a two-car attached garage, ample storage, and a functional floor plan designed for modern living. Conveniently located just minutes from the Queenstown Premium Outlets, Route 301, waterfront restaurants, marinas, and the many attractions of Maryland's Eastern Shore, this home also offers an easy commute to Annapolis, the Chesapeake Bay Bridge, and Delaware beaches. If you're searching for a spacious Queenstown home for sale with flexible living spaces, country charm, and a prime location, this exceptional property is one you won't want to miss.

306 Overlook Dr, Queenstown

Listing courtesy of Coldwell Banker Realty. Contact: kelly.thompson@cbmove.com
$485,000
2 Beds ⋅ 3 Baths
BACK on the MARKET. GREAT OPPORTUNITY at THIS PRICE. This Chester model has scenic, seasonal views of Macum Creek, beautiful sunrises, and an incredible display of wildlife in all seasons. Easy walk to Kayak launch and creek. With nearly 2000 square feet of open living space this home has a great layout for entertaining family and friends. The spacious great room, adjacent to the dining area and kitchen, provide an open area for gatherings. The gourmet kitchen is equipped with upgrades from the stunning kitchen island with quartz counter tops, beautiful upgraded cabinetry to the GE Profile appliances. This kitchen is designed for everyday living as well as hosting the occasional dinner party. The primary bedroom, is a separate self-contained suite complete with two closets and a luxury owners' bath that includes double sinks, and quartz countertops. The bright and airy 2nd bedroom is also a separate suite with a full bath and an oversized walk-in closet. In addition to the two bedrooms, there is a home office with stylish French Doors and a powder room for guests. The separate laundry room is equipped with a GE washer and dryer. This home also has a garage with adjoining driveway/parking space and large personal storage room which is a few short steps from the elevator. This home is just a short walk to resident kayak racks with launch access to the Chester River. KEEP IN MIND THIS CHESTER MODEL, WITH PLENTY OF FEATURES AND UPGRADES INCLUDED, IS MOVE-IN READY AND PRICED TO SELL***** Award-winning 24,000 Square Foot Clubhouse with Stunning Chester River Views! Fantastic amenities include 4.3 miles of walking trails throughout the community, outdoor infinity pool, indoor pool with on-duty lifeguard, fitness center, library, game room, gas and wood burning fire pits, Tiki bar equipped with refrigerators, sinks and television monitors, pier with transient boat slips, walking paths that link to the Cross Island Trail, lighted pickle ball courts, tennis courts, bocce, dog park, and an outdoor amphitheater for live music and movie nights. The community lifestyle director will keep you busy with daily activities such as yoga, a variety of exercise classes and an assortment of clubs including biking, billiards, book club, baking, mahjong, environmental club, trivia night and more. In addition to the weekly and monthly activities, residents can enjoy crab feasts, oyster roasts, and holiday gatherings throughout the year. This development is an unrivaled, amenity-filled, resort-style experience with convenient access to Annapolis, DC, Baltimore, and BWI. Kent Island offers multiple dining and shopping options, a nearby outlet mall, and a 6.5 mile cross-island trail surrounded by views of the Chester River.

1000 Herons Nest Way Unit #22, Chester

Listing courtesy of RE/MAX Executive. Contact: 4432741900
$174,000
This prime residential land parcel, located in the desirable ROMANCOKE ON THE BAY subdivision in Stevensville, MD, offers a unique investment or building opportunity with significant potential for appreciation. Spanning 0.56 acres, this corner lot features wooded areas, providing both privacy and a natural aesthetic that enhances the property's overall appeal. Strategically positioned just about four blocks from the picturesque Eastern Bay, this lot benefits from proximity to water-oriented activities without the premium of direct waterfront ownership. Investors can capitalize on the growing demand for properties near water bodies, making this an attractive option for future development. The community amenities are a standout feature, including a boat ramp, clubhouse, picnic area, and jogging/walking paths. These facilities not only enhance the quality of life for residents but also increase the property's desirability to potential buyers or renters. With super low association fees, investors can enjoy the benefits of community amenities without the burden of high costs. The lot's corner location alongside the South Kent Island walking path provides ample privacy and accessibility, which can be advantageous for future residential building projects. The surrounding area is poised for growth, making this property an excellent long-term investment. As demand for residential properties near water continues to rise, this lot presents a compelling opportunity for those looking to enter the real estate market or expand their portfolio. In summary, this 0.56-acre corner lot in ROMANCOKE ON THE BAY is not just a piece of land; it's a strategic investment in a thriving community with abundant amenities and proximity to Eastern Bay. With the potential for appreciation and the appeal of a water-oriented lifestyle, this property is a must-consider for savvy investors looking to maximize their returns or those seeking to build their dream home.

Touhey Dr, Stevensville

Listing courtesy of Realty Navigator. Contact: 4106433404
$725,000
2 Lots, 2 tax parcels 3.38 acres facing US Route 50/301 on Hess Frontage Road. Quasi Private Drive shared with Delmarva Power Company right of way, Whaler Boat Sales, Furniture Sales, Zoned Urban Commercial with most uses permitted. Has a private rear right of way to County Wilson Road for possible sewer hook-up currently has existing single family residence with 1 bath, kitchen living room and 2 bedrooms, covert it to office and add your workshop, storage buildings.

144 Hess Frontage Rd, Grasonville

Listing courtesy of Tidewater Properties. Contact:

$520,000
4 Beds ⋅ 3 Baths
Welcome to this charming home nestled in the quaint town of Ingleside, MD, offering the perfect blend of comfort, space, and peaceful country living. Situated on a generous .70 acre lot, this 2 1/2 story residence provides room to grow, and enjoy the beauty of it’s serene surroundings. Inside, you’ll find 4 spacious bedrooms, 2 full baths and 1 half bath, thoughtfully designed for both everyday living and entertaining. The kitchen features sleek stainless steel appliances, self closing cabinetry, and a cozy eat-in area, while a separate formal dining room provides the perfect setting for gatherings and special occasions. Luxury Vinyl Plank flooring runs throughout the main living area, offering durability and style, with soft carpeting in the bedrooms for added comfort. The primary suite includes a private en-suite bath with a walk in shower, creating a relaxing retreat at the end of the day. The versatile fourth bedroom on the third floor offers endless possibilities- ideal as a playroom, home office, or private getaway space. Step outside to a large rear deck with IPE decking, overlooking a fully fenced backyard, perfect for pet, children, or simply enjoying the outdoors. Additional features include an encapsulated crawl space for improved energy efficiency and moisture control, a spacious storage shed, and a chicken coop with chickens that can convey with the property if desired. Perfect for those looking to embrace a bit of country living. This property offers the tranquility of rural life with all the comforts of home, don’t miss your opportunity to make it yours.

2649 Roberts Station Rd, Ingleside

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

$505,000
2 Beds ⋅ 2 Baths
Bay Bridge Cove is a premier, amenity-rich, 55+ community on beautiful Kent Island! This absolutely adorable, compact Easton is loaded with cottage charm and offers the opportunity to move into this sought-after community at a remarkable price! It starts with a custom-paved courtyard, hardwood floors, fresh professional painting, and easy main-level living. The open-flow floor plan features an island kitchen with custom pendant and under-counter dimmable lighting, a great room, and a dining room, located on a premium lot with a grassy lawn and privacy from a tree-lined view, and a massive 4' crawl space with inside stairway access for storage. Walking distance to the clubhouse, pool, and all the community amenities, including an outdoor pool, tennis, pickleball, bocce, crab shack, community herb and vegetable gardens, walking paths, dog park, and clubhouse with exercise room, meeting room, library, and game room. Ideally located less than 5 minutes to the Bay Bridge, shopping, and waterfront restaurants, and within walking distance to Kent Manor Beach Club, with easy access to the Cross Island Trail, public parks, Eastern Shore beach towns, Annapolis, BWI, Baltimore, DC, and multiple nationally recognized medical facilities. A perfect place to call home!

854 Moorings Cir Unit #12, Stevensville

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

$765,000
2 Beds ⋅ 3 Baths
Penthouse Unit! Seller offering closing cost assistance to qualified buyers! Rare top floor unit with year-round water views perfectly positioned to capture stunning sunrises every morning. This home has been owned and meticulously maintained by the original owner who spared no expense and opted for every builder upgrade that was offered, over $60,000.00 in options. The open concept design seamlessly connects the living room, dining area, and kitchen areas, all enhanced by expansive windows letting in an abundant amount of natural light. Experience resort style living in the highly sought after Four Seasons at Kent Island, a premier 55+ waterfront community. Residents enjoy access to world class amenities, including indoor and outdoor pools, walking trails, a Chester River pier. Ideally located just minutes from waterfront dining, shopping, and the Chesapeake Bay Bridge, this home offers the perfect blend of relaxation, convenience and low maintenance living at its finest.

111 Marshgrass Way Unit #43, Chester

Listing courtesy of Coldwell Banker Realty. Contact: 4102638686
$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