Refine Search
Map
Sort by
$543,900
4 Beds ⋅ 4 Baths
Beautiful Single-Family Home in Much Desired Location. New Carpet, Fresh Paint, Re Finished Hardwood Floors, Upgraded Counter Tops, Primary Bath, Walk in Closet(s). Fully Finished Walkout Basement. Must See!

13100 Rockridge Rd, Chester

Listing courtesy of Epique Realty. Contact: 8888933537
$393,900
4 Beds ⋅ 3 Baths
Welcome to this beautiful four-bedroom home nestled in the heart of Chester! Situated on a quiet cul-de-sac, this spacious two-story residence offers approximately 2,392 square feet of comfortable living space. Step inside to a warm and inviting front living room that flows seamlessly into the formal dining room, complete with an elegant chandelier—perfect for hosting gatherings. The heart of the home is the expansive kitchen, featuring a center island, stainless steel appliances, pantry, and abundant cabinet space. The kitchen opens to a bright eat-in area with direct access to the backyard, as well as a large family room highlighted by a cozy gas fireplace—ideal for relaxing or entertaining. Upstairs, the primary suite offers a private retreat with two walk-in closets and an ensuite bath featuring a double vanity, walk-in shower, and separate soaking tub. The second level also includes a convenient laundry room and three additional generously sized bedrooms that share a full hall bathroom. Enjoy outdoor living with a concrete patio—perfect for grilling—and a beautifully maintained backyard garden. Additional highlights include a newer roof (2020) and a spacious two-car garage with ample storage. Conveniently located just minutes from I-95 and Route 288, with easy access to shopping, dining, and more. Schedule your showing today—this one won’t last!

2937 Abbeydale Ct, Chester

Listing courtesy of Move4Free Realty, LLC. Contact: 2023691460
$999,000
5 Beds ⋅ 5 Baths
Welcome to luxury coastal living in the highly desirable Four Seasons at Kent Island 55+ community in Chester. Built in 2025, this practically new home offers the perfect blend of elegance, comfort, and convenience — without the wait for new construction. Ideally situated on coveted Kingfisher Lane, this exceptional Tuscaloosa model offers over 3,200 square feet of beautifully designed living space with 5 bedrooms and 4.5 baths. The upgraded stone-and-shake exterior creates stunning curb appeal, while the covered front porch offers peaceful peek-a-boo water views — the perfect place to enjoy your morning coffee at sunrise. Inside, the open-concept main level showcases a thoughtfully upgraded interior with classic cabinetry, glass display cabinets, and professional-grade GE appliances in the kitchen. The spacious living area is anchored by a dramatic stone gas fireplace, while custom wall detailing and molding upgrades in the foyer and primary suite add warmth and sophistication throughout the home. Norman shutters on every window, upgraded carpet with premium padding, and carefully selected finishes elevate every room. The main-level primary suite offers a private retreat with elegant trim details and a spa-inspired en suite bath featuring a luxurious soaking tub designed for relaxation. Additional upgrades include a screened porch for outdoor enjoyment, epoxy garage flooring, painted garage walls, and a dedicated EV charging station for modern convenience. Located just a short distance from the community dog park, playground, pickleball and tennis courts, and the state-of-the-art clubhouse, this home offers not only exceptional design but also an unmatched lifestyle. Residents of Four Seasons at Kent Island enjoy resort-style amenities including indoor and outdoor pools, a fitness center, walking trails, social spaces, and activities designed to support an active and vibrant coastal lifestyle. All of this is ideally located just minutes from the Chesapeake Bay Bridge, offering convenient access to Washington and Baltimore, while also being close to shopping at the Queenstown Premium Outlets and an array of local waterfront dining and everyday conveniences.

233 Kingfisher Ln, Chester

Listing courtesy of Samson Properties. Contact: 7033788810
$559,000
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
$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
$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
$195,000
3 Beds ⋅ 2 Baths
🏡 This home qualifies for special financing opportunities, including access to in-house lender programs and available grant assistance for eligible buyers! 💰 Whether you’re a first-time buyer, a homeowner who is relocating, or looking to reduce out-of-pocket costs, you may qualify for down payment and closing cost assistance. Don’t miss the chance to make homeownership more affordable — contact today for details and qualification information! Completely remodeled and truly move-in ready! This home features brand new flooring throughout, including beautiful new floors that add warmth and modern appeal to every room. The property has been fully renovated with all new framing and insulation, new plumbing (PVC & PEX), a brand new electrical system with 200 AMP service, new doors and windows, and a 2025 roof. The home is filled with beautiful lighting that enhances the bright and inviting layout. With all major systems brand new, you will not have any issues for years to come. Architectural plans and full renovation details are available upon request. No HOA. Conveniently located near Widener University, Subaru Park, Interstate 95, and the Commodore Barry Bridge for easy commuting. Close to Eddystone Crossings, perfect for convenient shopping and everyday needs.

1119 Thomas St, Chester

Listing courtesy of Giraldo Real Estate Group. Contact: 2157450101
$724,500
5 Beds ⋅ 4 Baths
Price improvement! Motivated sellers. This custom built home offers the perfect opportunity to live just minutes away from the Chesapeake Bay Bridge and Route 50, offering partial water views and a layout designed for both everyday living and effortless entertaining. The main level features 12 foot ceilings and oversized 6 foot windows that create bright, open living spaces. A vaulted morning room transitions seamlessly into a sunroom, providing flexible space for dining, relaxing, or working from home. The gourmet eat-in kitchen offers granite countertops, a substantial center island, pantry, and an open-concept design that opens into the family room and sunroom. The primary suite is generously sized, featuring a tray ceiling and a well-designed bath with custom tile shower and double vanity. The remaining four bedrooms share two jack-and-jill style bathrooms offering convenience for family and guests. Outdoor living is equally appealing, with an 800-square-foot wraparound deck ideal for entertaining. The property also offers space for a potential in-ground pool (buyer to verify with Planning & Zoning). Additional features include custom hardwood and tile flooring run throughout, tailored Roman blinds and wood shutters, new HVAC system, finished garage, and dedicated laundry room with new washer, dryer, and utility sink. A rare 1,820-square-foot crawl space with 4-foot ceilings, finished concrete floor, and indoor access provides plenty of additional storage. Built by local builder Lacrosse Homes with numerous upgrades, this well-maintained home offers immediate value in one of the most popular areas on the Eastern Shore - all with no HOA. Schedule your tour today.

1868 Roberta Dr, Chester

Listing courtesy of Coldwell Banker Realty. Contact: 4102638686
$470,000
3 Beds ⋅ 3 Baths
New and improved price! This beautifully updated and well maintained home delivers exceptional value in the highly desirable Harbor View community—just two miles east of the Chesapeake Bay Bridge. Set on a picturesque 0.35‑acre corner lot, this 3‑bedroom, 2 full and 1 half bath home blends comfort, quality, and an unbeatable location. Inside, you’ll love the bright, updated kitchen featuring new countertops and backsplash, complemented by hardwood floors on the main and upper levels. A dramatic cathedral ceiling with skylights fills the home with natural light, creating an open and welcoming atmosphere. The spacious lower‑level family room offers a cozy retreat, while a flexible bonus room is perfect for a home office, guest room, or additional sleeping space. *Recent improvements add peace of mind and long‑term value, including a new roof (2019) with 50‑year shingles, new stove and hot water heater, and a new vinyl pool liner with a lifetime warranty. *Enjoy peace of mind with brand-new Pella tilt-in windows installed throughout the home in 2025, combining style, convenience, and energy efficiency. The pool is also equipped with a new robotic cleaner, making maintenance simple and hassle-free. The pool is open! Step outside to a fully fenced backyard oasis featuring a private in‑ground pool and deck— ready for summer entertaining or relaxing at home. Residents also enjoy access to the Harbor View community’s one‑acre field with pavilion and playground, perfect for gatherings and outdoor fun. Conveniently located just 20 minutes to Annapolis, 45 minutes to Baltimore, and under an hour to Washington, D.C., this home also offers easy access to Kent Narrows waterfront dining, the 6.5‑mile Cross Island Trail, and Queenstown Premium Outlets just minutes away. With updated features, transferable warranties, and a refreshed price, this home is move‑in ready and offers an outstanding opportunity to enjoy the best of Kent Island living. Schedule your showing today—this one is not to be missed.

1916 Stevens Dr, Chester

Listing courtesy of Coldwell Banker Realty. Contact: kelly.thompson@cbmove.com
$120,000
2 Beds ⋅ 1 Baths
Investment opportunity in Chester. 1337 Townsend Street offers rental potential. This property features 2 bedrooms on the main floor. There is also an extra storage room accessed through the living room. Conveniently located near Widener University and public transit.

1337 Townsend St, Chester

Listing courtesy of Keller Williams Main Line. Contact: 6105200100
$1,294,800
4 Beds ⋅ 4 Baths
*****Immediate Delivery*****WATERFRONT DEEP WATER ****Schedule showoing today! New Home, New Pier, New Pool!!!!!The Blue Heron is a new home design offered by Lacrosse Homes. The single family design features now one but TWO decks -- one from the second floor great room and the second from the third level primary bedroom suite. Take in all the beautiful sights and sounds of a Coastal Maryland lifestyle in this home built for entertaining and an enhanced lifestyle! There is room for everyone in this home, starting with a main level 2-car garage, rec room area, full bath & exercise/office -- this is your fun zone or whatever zone! The second level is light-filled and open with island kitchen featuring upgraded finishes, dining area, powder bath and great room with deck. You can ADD another deck on the rear of the home off the dining area if you're looking for more outdoor space. The third level features a laundry, three bedrooms including the spacious primary bedroom with updated bath and another stunning deck. The Blue Heron is a beautiful home and will serve a multitude of lifestyles. Explore your options today!

1757 Harbor Dr, Chester

Listing courtesy of Keller Williams Flagship. Contact:

$19,500
2 Beds ⋅ 1 Baths
This property, situated on a 0.17-acre lot, offers a blank canvas for your vision. Located in Queen Anne's County, the existing structure presents endless possibilities for the right buyer. Take advantage of the spacious lot size, perfect for outdoor activities or future expansion plans. Buyers are encouraged to perform their own due diligence to verify property details. Please note that access to 1405 Little Creek Rd is via 104 Little Creek Ct, followed by a left turn. Do not use or enter any neighboring driveways or properties as they are privately owned and clearly marked with “No Trespassing” signs. For safety reasons, please respect these boundaries.

1405 Little Creek Rd, Chester

Listing courtesy of The Parker Group. Contact: 3022176692
$439,900
3 Beds ⋅ 2 Baths
PRICE Improvement...Discover the charm of this fully updated ranch in a serene, water-privileged community! With a spacious yard and an inviting open floor plan, this home features a stunning new kitchen complete with a large white granite island, sleek white cabinets, and stainless steel appliances. Sunlight floods the dining area through new sliding doors, while the generous living room is accented with stylish shiplap walls. There's Nothing Like NEW! Step onto the new flooring that leads you to three roomy bedrooms and two beautifully renovated full baths. Every detail has been attended to, with all-new windows, siding, plumbing, fixtures, electrical panel, light switches, septic work, water heater, doors, drywall, and a new HVAC system. With a recent roof and a dehumidified crawl space featuring a vapor barrier, this home is move-in ready—no worries, just settle in! The community enhances your lifestyle with access to four beaches, three boat ramps, a playground, ball fields, a basketball court, a picnic pavilion, a fishing pier, and plenty of opportunities for gatherings. This is the perfect place to create lasting memories!

1340 Queen Anne Dr, Chester

Listing courtesy of RE/MAX Executive. Contact: 4432741900