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$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

$1,900,000
3 Beds 2 Baths
Steeped in history and surrounded by the timeless beauty of Maryland’s Eastern Shore, 1130 Old Love Point Road presents a once-in-a-generation opportunity to own an extraordinary family farm in the heart of Kent Island. Spanning approximately 36.73 acres, this remarkable property blends agricultural heritage, historic character, and exceptional future potential in one of the Shore’s most storied locations. At the center of the property sits an historic Victorian farmhouse dating to circa 1896, recognized by the Maryland Historical Trust as a historically contributing structure representative of the classic 19th-century Delmarva farmhouse. The home and grounds reflect generations of stewardship and offers tremendous opportunity for its next generation renovation, rehabilitation and future development prior to occupancy. Old Love Point Road itself carries a rich and fascinating history. Before the Chesapeake Bay Bridge connected Maryland to the Eastern Shore, Love Point served as one of the principal gateways to the Shore. Ferries, steamships, and rail lines once brought travelers from Baltimore and Annapolis to Kent Island, where they continued eastward across Maryland and Delaware. Love Point became known as a romantic waterfront destination and transportation hub, welcoming visitors arriving by ferry and the historic Queen Anne’s Railroad. The property’s location captures the spirit of that history while offering exceptional convenience to today’s modern traveler. Situated just minutes from Route 50 and the Chesapeake Bay Bridge, the farm offers easy access to Annapolis, Washington D.C., Baltimore, and the Delaware beaches while maintaining the peaceful charm of Eastern Shore living. Currently farmed and designated as prime farmland, the property is ideally suited for a gentleman’s farm, equestrian estate, vineyard, winery, agritourism venue, or luxury country retreat. The Development Analysis Report identifies a winery as one of the site’s most favorable and viable uses, noting that agritourism operations such as vineyards and wineries are specifically encouraged within Queen Anne’s County’s future agricultural economy plans. In addition to its agricultural and lifestyle appeal, the property, perhaps most importantly, offers substantial long-term development potential. Located within the County’s Suburban Estate zoning district and designated growth area, the site may support future residential subdivision opportunities, including large-lot estate development, clustered single-family communities, multifamily concepts, or additional residential lots under current moratorium guidelines. Whether envisioned as a private family compound, vineyard and winery destination, legacy investment, or future development opportunity, 1130 Old Love Point Road represents a rare chance to own a meaningful piece of Maryland’s Eastern Shore history — where the past, present, and future converge along one of Kent Island’s most iconic roads.

1130 Old Love Point Rd, Stevensville

Listing courtesy of Monument Sotheby's International Realty. Contact: (443) 746-2090

$2,769,000
5 Beds 8 Baths
Designed by YSA Homes and Simply Wesley Interior Design of Annapolis, this extraordinary brand-new modern coastal farmhouse style smart-home offers over 6,148 square feet of thoughtfully designed living space, where every tile throughout the home was handpicked and expertly curated using top-of-the-line luxury selections. The kitchen is outfitted with premium, top-tier appliances including Wolf, creating a seamless blend of elevated craftsmanship, timeless design, and modern functionality at every turn. The property is permitted for a pool to be built. This stunning residence features five oversized bedrooms, each with its own expansive en suite bathroom, and three of the five have waterfront bay views. Totals include six full bathrooms, two half bathrooms, five gigantic bedrooms, 2 car oversized attached garage with rear entry door. An owner’s suite on the main level (with huge custom closet) provides everyday convenience, while the second level includes an additional  owner’s suite with a massive custom walk-in closet, ideal for multi-generational living or extended guest stays. Upon entering the home, you are welcomed into an open-concept main level where the kitchen flows seamlessly into the dining and living areas, creating an ideal setting for entertaining and everyday living. The living room is anchored by a striking wireless water vapor fireplace, offering modern ambiance without heat or emissions. A main-level half bath adds convenience, while the primary suite features a spa-inspired oversized bathroom with a soaking tub, a large European-style walk-in shower, and exquisite designer finishes throughout. The second level impresses with a spacious great room, complete with a wet bar and an additional half bath, opening to a large upper-level deck designed for optimal water views and entertaining. Four generously sized en suite bedrooms are located on this level, two of which showcase stunning water views through oversized windows, filling the space with natural light. The lower level offers exceptional flexibility, featuring a walk-out basement with exterior sliding doors, a full bathroom, a dedicated laundry room, and ample space for a game room, den, home gym, or additional living areas. Ask the listing agent about available improvement and build-out options for the basement. Outdoor living continues on the main-level patio, with the option to expand or customize to suit your vision. Located on sought-after Kent Island, this home offers access to a true Chesapeake Bay lifestyle just approximately 20 minutes from historic downtown Annapolis. Enjoy nearby waterfront parks, marinas, beaches, and miles of scenic walking and biking trails along the Cross Island Trail. Golf enthusiasts will appreciate proximity to Blue Heron Golf Course with membership options available, as well as the nationally recognized Queenstown Harbor Golf Links featuring two championship courses. Residents can easily enjoy all that downtown Annapolis has to offer, including boutique shopping, waterfront dining, sailing culture, festivals, and the charm of the historic district and U.S. Naval Academy. Just minutes away, **Queenstown Premium Outlets—featuring Calvin Klein, J.Crew, and other popular brand-name retailers—*provide convenient access to everyday shopping. Kent Island is also home to waterfront dining, local crab houses, and Love Point Vineyards, while Terrapin Nature Park and Matapeake Beach offer stunning Chesapeake Bay views. Conveniently positioned for commuting to Baltimore and Washington, D.C., this location blends coastal living with everyday accessibility. This is not just a home, this is a coastal lifestyle.

414 Bay Dr, Stevensville

Listing courtesy of Cummings & Co. Realtors. Contact: (410) 823-0033

$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

$675,000
4 Beds 2 Baths
Photos Coming Soon! Welcome to this beautifully maintained one-level rancher, perfectly situated on a private 1-acre lot. Offering 2,441 square feet of comfortable living space, this home provides 4 bedrooms, 2 full baths, and has an inviting open floor plan designed for everyday living and entertaining. Thoughtful architectural details, including coffered ceilings and crown molding, add character and elegance throughout the main living areas. The spacious living room is anchored by a fireplace with a wood-burning insert, creating a warm and welcoming atmosphere. The well-appointed kitchen offers abundant cabinet and counter space and opens seamlessly to the main living areas. The dining area is spacious, ideal for hosting family and friends. A large four-season room, complete with heating and cooling, provides additional year-round living space and overlooks the lovely backyard. Step outside to enjoy the expansive deck and pergola-covered seating area, perfect for relaxing or entertaining. The fully fenced backyard offers plenty of room for outdoor activities while maintaining a sense of privacy. A detached two-car garage features a heated and cooled bonus room above, ideal for a home office, gym, hobby room, or additional flex space. Major improvements completed within the past five years include a newer HVAC system, roof, gutters, and kitchen updates, providing added value and peace of mind. This exceptional property combines the convenience of one-level living with modern updates, versatile spaces, and a peaceful setting—ready for you to call it home.

2200 Bennett Point Rd, Queenstown

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

$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

$409,000
3 Beds 2 Baths
Welcome Home! Eastern Shore Cape Cod awaits new Owners. Awesome 3 bed 2 bath home has a little bit of something for everyone. Cozy floor plan features entry level bedroom plus 2 large 2nd floor bedrooms. Granite counters, carpet and vinyl plank flooring throughout. Outside features backyard patio for entertaining and large fenced rear yard with room for garden, firepit or critters. The real gem is the 24x36 garage connected by covered breezeway. Room for vehicles, boat, workshop, man cave or she shed. Also included is an outlet for RV hook-up. Conveniently located close to public boat ramps, The Crumpton Auction, DE tax Free shopping and Rt 301 for commuters. Professional pics to come. Minor excluded items

100 Clark Ct, Millington

Listing courtesy of Berkshire Hathaway Homeservice Homesale Realty. Contact: (800) 383-3535

$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

$534,900
5 Beds 3 Baths
Welcome to 126 Meadowcroft Drive — a beautifully updated 5‑bedroom, 2.5‑bath home tucked in one of Centreville’s most desirable neighborhoods. With a brand‑new roof within the last few years and newer dual‑zoned HVAC units, this spacious home offers modern comfort, low maintenance, and peace of mind from day one. Step inside to find fresh updates throughout, including stylish finishes, gas fireplace and a bright, inviting layout perfect for both everyday living and entertaining. The main level features generous living spaces, an updated kitchen, and a flexible floor plan suited for today’s lifestyle. Upstairs, five well‑sized bedrooms provide ample room for family and guests. The primary suite offers its own private bathroom with a tile shower and soaking tub, while an additional full bath ensures convenience for all. Outside, enjoy a quiet setting with space to relax on the back patio complete with a firepit—ideal for anyone seeking both comfort and room to unwind in a well‑established community. Move‑in ready and thoughtfully updated, 126 Meadowcroft Drive delivers ease of ownership and timeless small‑town charm. Don’t miss this opportunity!

126 Meadowcroft Dr, Centreville

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

$749,000
4 Beds 4 Baths
Experience the best of Kent Island living in this beautifully maintained coastal home, ideally situated in the highly desirable Water's Edge section of Gibson's Grant. Built in 2017, this exceptional residence enjoys unobstructed pond views from the welcoming covered front porch, where you can relax while watching blue herons and other native wildlife. Perfectly positioned just one block from the community's exceptional waterfront amenities, including the Chester River, clubhouse, pool, fitness center, kayak launch, fishing pier, and waterfront pavilion, this home offers the perfect blend of luxury, convenience, and the relaxed lifestyle of Maryland's Eastern Shore. Step inside to discover a bright, thoughtfully designed floor plan where beautiful flooring flows throughout the main level and abundant natural light fills every room. Designed for both everyday living and effortless entertaining, the main level offers exceptional versatility with a spacious flex room that is ideal as a home office, den, sitting room, or additional living space, along with a convenient powder room for guests. The heart of the home is the expansive open-concept living area, where the spacious family room, dining area, and beautifully appointed kitchen come together seamlessly. The kitchen features a large center island with abundant seating and workspace, while the family room is highlighted by a beautiful gas fireplace. Just beyond, the brand-new screened porch opens to your own private backyard oasis featuring a beautifully landscaped paver patio, a tranquil ornamental pond with a cascading waterfall, full privacy fencing perfect for pets, and an irrigation system to keep the grounds looking their best. Designed for the ease of first-floor living, the main level features a spacious primary suite privately situated at the rear of the home. The luxurious ensuite bath includes a relaxing Jacuzzi soaking tub, while a second main-level bedroom offers its own private full bath, making it ideal for guests or multigenerational living. The staircase to the upper level is thoughtfully tucked toward the rear of the home, enhancing the home's functional layout. Upstairs, you'll find two generously sized bedrooms and a beautifully appointed full bath, providing comfortable accommodations for family and guests. Completing the home is a spacious rear-entry two-car garage with plenty of room for parking and storage, plus a custom-built workspace perfect for DIY enthusiasts, hobbyists, or woodworking projects. An approximately four-foot-high conditioned crawl space with interior access provides exceptional additional storage. Recent improvements include a brand-new HVAC system, brand-new screened porch, one-year-old oven, and new washer and dryer, allowing you to move in with confidence. Residents of Gibson's Grant enjoy resort-style amenities, including a clubhouse, outdoor pool, fitness center, waterfront pavilion, kayak launch, fishing pier, water access, and direct access to the Cross Island Trail. Tucked behind a peaceful nature preserve just off Route 50, this sought-after waterfront community offers the perfect balance of tranquility and convenience. Located just moments from the Chesapeake Bay Bridge, the home provides an easy commute while placing you minutes from waterfront dining, marinas, shopping, parks, and local entertainment. Beautifully maintained, thoughtfully updated, and ideally located in one of Kent Island's most desirable neighborhoods, this exceptional home offers the perfect opportunity to embrace luxury coastal living on Maryland's Eastern Shore. Schedule your private showing today! Mortgage savings may be available for buyers of this listing.

134 Richard Ingle Way, Chester

Listing courtesy of Redfin Corp. Contact: 3016586186

$895,000
3 Beds 3 Baths
Welcome to Southwind, one of Kent Island's most desirable waterfront communities, where peaceful surroundings and an exceptional lifestyle come together. Perfectly positioned on 1.22 beautifully landscaped acres with water views, this inviting single-level home offers the comfort, space, and amenities you've been searching for. Inside, you'll find three spacious bedrooms and three beautifully updated full baths, creating a home that is both stylish and comfortable. Freshly painted throughout, with newly refinished hardwood floors and plush new carpeting in the bedrooms, every room feels bright, fresh, and move-in ready. The heart of the home is the welcoming kitchen, featuring gleaming granite countertops, crisp white cabinetry, a generous pantry with charming French doors, peninsula seating for casual meals and conversation, a vaulted breakfast area with a dramatic palladium window showcasing beautiful water views, and brand-new stainless steel range and refrigerator. Whether you're preparing dinner or gathering with family and friends, this space is designed to bring everyone together. The adjoining family room is warm and inviting, centered around a cozy propane fireplace and accented by custom built-in bookshelves that add both charm and functionality. A sliding glass door opens directly to the slate patio, creating an effortless connection between indoor and outdoor living. Just off the main living area, the light-filled dining room is surrounded by large windows that frame lovely water views, creating the perfect backdrop for everyday meals and special occasions. A versatile bonus sunroom offers even more living space and can easily serve as a cozy den, home office, or additional bedroom to fit your needs. Step outside to enjoy the fenced backyard and slate patio, where a remote-operated awning provides welcome shade at the touch of a button, making it the perfect spot for morning coffee, evening sunsets, or weekend barbecues. Car enthusiasts, hobbyists, and those needing extra space will appreciate the oversized four-car garage. Above, an expansive unfinished area offers endless possibilities. Already plumbed for a future bath, it's ready to become a guest suite, home office, recreation room, or whatever your imagination inspires. Energy efficiency is another standout feature, with owned solar panels and two Tesla Powerwall storage batteries helping to keep utility costs remarkably low while providing added peace of mind. Living in Southwind means more than owning a beautiful home—it's embracing a waterfront lifestyle. Residents enjoy access to the community boat launch, waterfront clubhouse, boat storage lot, pickleball and tennis courts, and scenic nature trail along the water. Whether you're launching your boat for a day on the Chesapeake Bay, enjoying an evening stroll by the shoreline, or simply relaxing at home while taking in the tranquil water views, this property offers the perfect blend of comfort, community, and coastal living.

2810 Harvest Ct, Chester

Listing courtesy of Blackwell Real Estate, LLC. Contact: 4432214120

$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! More pictures are coming soon!! Sellers prefer 24 hours notice for showings, but if you need one sooner, don't hesitate to call or text the listing agent & sellers will try to accommodate!

123 Heath Rd, Chestertown

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

$989,000
5 Beds 4 Baths
Discover the extraordinary waterfront oasis of 2702 Sherman Dr. in Chester. This remarkable residence, featuring 5 bedrooms, 2 full bathrooms, and 2 half bathrooms, has undergone a stunning renovation, creating a haven of luxury and serenity on a peaceful street. Every detail of this home has been impeccably updated, from the oversized windows to the modernized bathrooms. However, the true centerpiece is the fully equipped gourmet kitchen, a masterpiece of design. A magnificent 10-foot Quartz center island takes center stage, surrounded by pristine cabinets, state-of-the-art appliances, and exquisite marble countertops. To top it off, the kitchen also boasts its own wet bar with a built-in beverage cooler. The open-concept layout seamlessly connects the kitchen to the living space, with a mesmerizing wall of oversized windows that offer breathtaking views of the expansive waterfront and private pier. Convenience is a priority in this home, with a three-car pull-through garage and a pier equipped with boat lift as well as dual Jetski lift for easy access to the water. Outdoor enjoyment is a given, with two waterfront decks, a screened-in patio, and a private en-suite deck for moments of relaxation. Privacy and the feeling of island-style living are abundant here. Located in the heart of Kent Island, this property provides effortless access to luxury dining options, waterfront restaurants, lively dock bars, and island-style entertainment. All while, being just 2 miles away from the Chesapeake Bay Bridge means seamless travel by land or sea. Welcome to your dream home, here on Kent Island where tranquility and luxury converge with Maryland's Eastern Shore and the Chesapeake Bay.

2702 Sherman Dr, Chester

Listing courtesy of Samson Properties. Contact: 7033788810

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

729 Kimberly Way, Stevensville

Listing courtesy of Samson Properties. Contact: 7033788810

$974,990
5 Beds 5 Baths
Welcome to the Tuscaloosa, a beautifully designed home that blends an open-concept floorplan with warm Farmhouse-inspired style, creating the perfect balance of comfort and functionality. Projected for November 2026 settlement, this spacious home features 5 bedrooms, 4.5 bathrooms, and a 3-car garage, offering plenty of room for everyday living, entertaining, and hosting overnight guests. Designed with versatility in mind, the Tuscaloosa includes two primary suites, making it an ideal layout for multi-generational living or accommodating long-term guests. The inviting fireplace serves as a cozy focal point for the main living area, while the screened patio provides the perfect outdoor retreat for enjoying fresh air in comfort throughout the seasons. Thoughtful design and quality craftsmanship come together to create a home that is both stylish and functional. For a complete list of included features and finishes, please contact our sales representatives. Photos are for illustrative purposes only and may not represent the exact home or finishes available. Welcome to a new luxury active adult 55+ community on Maryland's Chesapeake Bay. Discover the amenity-filled, resort-style experience within 45 miles of Washington DC and Baltimore. Residents can take advantage of the community's 24,000 sq. ft. clubhouse with indoor & outdoor pools, a state-of-the-art fitness center, and multiple tennis and pickleball courts. With a full-time lifestyle director on site the community also features a well-maintained calendar of activities such as walking club, indoor and outdoor yoga sessions, mahjong club, kayaking, pickleball and more. Kent Island life is about making friends and enjoying the company of people who have worked hard and now want to enjoy all that a luxury 55+ community has to offer. Located steps from the water and minutes from Annapolis, the location also offers quick access to Rt. 50. Enjoy the convenience of nearby dining and shopping options together with the quaint charm of a small town.

323 Kingfisher Ln, 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:

$789,990
4 Beds 3 Baths
Welcome to the Simone, a beautifully designed home offering 4 bedrooms, 3 baths, and a 2-car garage. This home combines thoughtful design with comfortable living spaces ideal for both everyday life and entertaining. The main living area features a cozy one-story fireplace, creating a warm and inviting focal point. A dedicated home office provides a private space for work or study, while the screened patio extends your living area outdoors—perfect for relaxing or hosting guests. The kitchen is designed for both style and function, featuring a single oven, microwave, gas cooktop with range hood, dishwasher, French door refrigerator, pendant lighting, tile backsplash, and quartz countertops. Quartz is also featured in the owner’s bath for a cohesive and elegant finish. Luxury vinyl plank flooring runs throughout the foyer, extended foyer, kitchen, dining area, great room, bedroom 2, owner’s suite, HovHall, loft/second floor, and bedrooms 3 and 4. Tile flooring is featured in all full baths and the laundry room. The owner’s bath includes a walk-in shower with a seat and handheld shower wand, along with a double-sink vanity for added comfort and convenience. 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. Welcome to a new luxury active adult 55+ community on Maryland's Chesapeake Bay. Discover the amenity-filled, resort-style experience within 45 miles of Washington DC and Baltimore. Residents can take advantage of the community's 24,000 sq. ft. clubhouse with indoor & outdoor pools, a state-of-the-art fitness center, and multiple tennis and pickleball courts. With a full-time lifestyle director on site the community also features a well-maintained calendar of activities such as walking club, indoor and outdoor yoga sessions, mahjong club, kayaking, pickleball and more. Kent Island life is about making friends and enjoying the company of people who have worked hard and now want to enjoy all that a luxury 55+ community has to offer. Located steps from the water and minutes from Annapolis, the location also offers quick access to Rt. 50. Enjoy the convenience of nearby dining and shopping options together with the quaint charm of a small town.

723 Warbler Way, Chester

Listing courtesy of Berkshire Hathaway HomeServices PenFed Realty - OP. Contact: 4102083500

$839,990
4 Beds 3 Baths
Welcome to the Simone, a beautifully designed home offering 4 bedrooms, 3 baths, and a 2-car garage. This home combines thoughtful design with comfortable living spaces ideal for both everyday life and entertaining. The main living area features a cozy one-story fireplace, creating a warm and inviting focal point. A dedicated home office provides a private space for work or study, while the screened patio extends your living area outdoors—perfect for relaxing or hosting guests. The kitchen is designed for both style and function, featuring a single oven, microwave, gas cooktop with range hood, dishwasher, French door refrigerator, pendant lighting, tile backsplash, and quartz countertops. Quartz is also featured in the owner’s bath for a cohesive and elegant finish. Luxury vinyl plank flooring runs throughout the foyer, extended foyer, kitchen, dining area, great room, bedroom 2, owner’s suite, HovHall, loft/second floor, and bedrooms 3 and 4. Tile flooring is featured in all full baths and the laundry room. The owner’s bath includes a walk-in shower with a seat and handheld shower wand, along with a double-sink vanity for added comfort and convenience. 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. Welcome to a new luxury active adult 55+ community on Maryland's Chesapeake Bay. Discover the amenity-filled, resort-style experience within 45 miles of Washington DC and Baltimore. Residents can take advantage of the community's 24,000 sq. ft. clubhouse with indoor & outdoor pools, a state-of-the-art fitness center, and multiple tennis and pickleball courts. With a full-time lifestyle director on site the community also features a well-maintained calendar of activities such as walking club, indoor and outdoor yoga sessions, mahjong club, kayaking, pickleball and more. Kent Island life is about making friends and enjoying the company of people who have worked hard and now want to enjoy all that a luxury 55+ community has to offer. Located steps from the water and minutes from Annapolis, the location also offers quick access to Rt. 50. Enjoy the convenience of nearby dining and shopping options together with the quaint charm of a small town.

715 Warbler Way, Chester

Listing courtesy of Berkshire Hathaway HomeServices PenFed Realty - OP. Contact: 4102083500

$2,400,000
4 Beds 4 Baths
Discover an exquisite Mediterranean-style residence nestled in the prestigious Southwind community, where luxury meets comfort while enjoying breathtaking sunset views. This stunning 4-bedroom, 3.5-bathroom home boasts 4,331 sq. ft. The gourmet kitchen features high-end stainless steel appliances, including a built-in microwave, wall oven, and a sleek cooktop, ensuring culinary excellence. Step outside to your private oasis, where a concrete pool invites relaxation amidst lush landscaping on a generous 1.2-acre lot that includes a covered built in Lynx grill and bar seating. Enjoy direct access to Cox Creek, complete with a private dock for fishing, kayaking, or simply soaking in the serene water views. With a double sided fireplace and three tankless water heater, this home combines elegance with modern convenience, making it a true sanctuary. The main living room features sky high ceilings and a wet bar making hosting a snap and flows into the added sunroom that features heated tile flooring. And the three season room off the back is the perfect gathering space with a wall of sliders to maximize the view. Meticulously maintained and thoroughy enjoyed by the original owners. The expansive rear yard and rip-rap shoreline enhance the outdoor experience, while the community amenities, including a beach, tennis/basketball courts, and fishing pier and boat launch, offer an exclusive lifestyle on Maryland's Eastern Shore.

2882 Cox Neck Rd, Chester

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

$929,990
3 Beds 3 Baths
Welcome to the Kerr, a beautifully designed home offering 3 bedrooms, 3 baths, and a 3-car garage. This home combines an open-concept layout with thoughtful design for both comfort and functionality. The main living area features a cozy fireplace with mantel and hearth, creating a warm and inviting focal point. A dedicated home office provides a private space for productivity, while the screened patio extends the living area outdoors—perfect for entertaining or relaxing. The kitchen is equipped for both style and performance, featuring a single oven, microwave, gas cooktop with range hood, dishwasher, French door refrigerator, pendant lighting, tile backsplash, and quartz countertops. Quartz is also featured in the owner’s bath for a cohesive, elegant finish. Hardwood flooring flows throughout the foyer, extended foyer, HovHall, kitchen, dining area, great room, home office, bedrooms 2, the primary suite, loft, and second floor, while tile is featured in all full baths and the laundry room. The primary bath includes a walk-in shower with seat and handheld shower wand and a double-sink vanity for added convenience and luxury. 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. Welcome to a new luxury active adult 55+ community on Maryland's Chesapeake Bay. Discover the amenity-filled, resort-style experience within 45 miles of Washington DC and Baltimore. Residents can take advantage of the community's 24,000 sq. ft. clubhouse with indoor & outdoor pools, a state-of-the-art fitness center, and multiple tennis and pickleball courts. With a full-time lifestyle director on site the community also features a well-maintained calendar of activities such as walking club, indoor and outdoor yoga sessions, mahjong club, kayaking, pickleball and more. Kent Island life is about making friends and enjoying the company of people who have worked hard and now want to enjoy all that a luxury 55+ community has to offer. Located steps from the water and minutes from Annapolis, the location also offers quick access to Rt. 50. Enjoy the convenience of nearby dining and shopping options together with the quaint charm of a small town.

532 Warbler Way, Chester

Listing courtesy of Berkshire Hathaway HomeServices PenFed Realty - OP. Contact: 4102083500

$210,000
3 Beds 2 Baths
Welcome to 3701 Barclay Rd, a fantastic opportunity to own a 3-bedroom, 2-bath manufactured home on nearly half an acre in the peaceful countryside of Queen Anne's County. Built in 2004, this property offers a spacious open floor plan ready for your vision and personal touch. Inside, you'll find a generously sized living area that flows into the kitchen featuring a center island, making it an ideal layout for everyday living and entertaining. Step outside to enjoy the rear porch overlooking the backyard, complete with an above-ground pool and a shed/outbuilding for additional storage. Whether you're an investor searching for your next value-add project or a homeowner looking to build equity while creating your dream home, this property is packed with potential. With some updates and repairs, this home could truly shine. Enjoy the privacy and charm of country living while remaining within easy reach of nearby towns, shopping, and commuter routes. Located in the desirable Queen Anne's County Public School District. Property is being sold strictly as-is.

3701 Barclay Rd, Marydel

Listing courtesy of LPT Realty, LLC. Contact: 8773662213

$929,990
3 Beds 3 Baths
Welcome to the Kerr, a beautifully designed home offering 3 bedrooms, 3 baths, and a 3-car garage. This home combines an open-concept layout with thoughtful design for both comfort and functionality. The main living area features a cozy fireplace with mantel and hearth, creating a warm and inviting focal point. A dedicated home office provides a private space for productivity, while the screened patio extends the living area outdoors—perfect for entertaining or relaxing. The kitchen is equipped for both style and performance, featuring a single oven, microwave, gas cooktop with range hood, dishwasher, French door refrigerator, pendant lighting, tile backsplash, and quartz countertops. Quartz is also featured in the owner’s bath for a cohesive, elegant finish. Hardwood flooring flows throughout the foyer, extended foyer, HovHall, kitchen, dining area, great room, home office, bedrooms 2, the primary suite, loft, and second floor, while tile is featured in all full baths and the laundry room. The primary bath includes a walk-in shower with seat and handheld shower wand and a double-sink vanity for added convenience and luxury. 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. Welcome to a new luxury active adult 55+ community on Maryland's Chesapeake Bay. Discover the amenity-filled, resort-style experience within 45 miles of Washington DC and Baltimore. Residents can take advantage of the community's 24,000 sq. ft. clubhouse with indoor & outdoor pools, a state-of-the-art fitness center, and multiple tennis and pickleball courts. With a full-time lifestyle director on site the community also features a well-maintained calendar of activities such as walking club, indoor and outdoor yoga sessions, mahjong club, kayaking, pickleball and more. Kent Island life is about making friends and enjoying the company of people who have worked hard and now want to enjoy all that a luxury 55+ community has to offer. Located steps from the water and minutes from Annapolis, the location also offers quick access to Rt. 50. Enjoy the convenience of nearby dining and shopping options together with the quaint charm of a small town.

540 Warbler Way, Chester

Listing courtesy of Berkshire Hathaway HomeServices PenFed Realty - OP. Contact: 4102083500

$669,900
4 Beds 3 Baths
Welcome to 220 Creeks End Lane, an elegant and stylish 4-bedroom, 2.5-bath home offering 2,840 square feet of beautifully designed living space in the desirable water oriented community of Cox Creek Landing. From the moment you enter, you will appreciate the spacious, open layout and thoughtful details throughout. Freshly refinished hardwood floors bring warmth and character to the home, while crown molding, recessed lighting, a separate dining room, and a private home office provide the perfect combination of style, comfort, and functionality. The inviting living area features a newly updated gas fireplace, creating a comfortable gathering space at the heart of the home. The spacious kitchen is enhanced by new appliances and offers plenty of room for cooking, entertaining, and everyday living. One of the home's most appealing features is the expansive screened-in porch overlooking the fenced backyard. Whether enjoying your morning coffee, entertaining friends and family, or relaxing at the end of the day, this exceptional outdoor living space is designed to be enjoyed throughout much of the year. The heated and cooled two-car garage provides year-round comfort and added flexibility for parking, hobbies, a workshop, or additional usable space. For boating enthusiasts, the waterfront lifestyle extends beyond the home. The seller owns a boat slip at the community pier equipped with a newer boat lift. The boat slip may be available for separate purchase outside of the real estate transaction, offering a rare opportunity to enjoy convenient access to the water just moments from home. Located in the water-oriented Cox Creek Landing community, residents enjoy access to the community pier, playground, and waterfront amenities. Elegant, stylish, spacious, and thoughtfully updated, 220 Creeks End Lane offers the perfect combination of comfortable living, exceptional outdoor spaces, and the Eastern Shore lifestyle. Sellers have a deeded easement boat slip and is available for sale.

220 Creeks End Ln, Stevensville

Listing courtesy of Real Estate Depot. Contact:

$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

$719,900
2 Beds 2 Baths
Experience the ease of elegant one-level living in this exceptional home, located in one of Maryland's premier 55+ active adult communities on the Chesapeake Bay. Designed for both comfort and style, this beautifully appointed residence features a three-car tandem garage with an EV charger, a spacious screened porch, a cozy gas fireplace, upgraded trim and designer feature walls. Thoughtful enhancements include Hunter Douglas plantation shutters, custom California Closets in the owner's suite and second bedroom, modern ceiling fans throughout, reverse osmosis water filtration, and professionally treated energy-efficient windows that reduce UV rays and heat for year-round comfort. Beyond your front door, enjoy a true resort-style lifestyle just 45 miles from both Washington, D.C. and Baltimore. The impressive 24,000-square-foot clubhouse offers indoor and outdoor pools, a state-of-the-art fitness center, tennis and pickleball courts, and an active social calendar led by a full-time lifestyle director. From kayaking, yoga, and walking clubs to mahjong, pickleball, and countless social events, there is something for everyone. Located just steps from the waterfront and minutes from historic Annapolis, this vibrant Kent Island community combines small-town charm with exceptional convenience. Enjoy easy access to Route 50, along with nearby shopping, dining, and everything that makes Chesapeake Bay living so special.

121 Merlin Dr, Chester

Listing courtesy of Coldwell Banker Realty. Contact: 4102638686