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

1810 Love Point Rd, Stevensville

Listing courtesy of Monument Sotheby's International Realty. Contact: (410) 525-5435
$60,000
Vacant lot ready for your own choice of residence. Walking distance to the Chester River community access by boat or just enjoy the waterfront on the community deck.

233 Merganser Dr, Chestertown

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

$199,900
3 Beds ⋅ 2 Baths
Nestled along the water's edge, this waterfront opportunity offers a canvas to create your own Eastern Shore retreat. Whether you choose to renovate the existing 3BR cottage or build on the existing foundation there is plenty of potential. Buyer to confirm building restrictions with the county. This property features a new deep well, new well pump, and new septic holding tanks in 2026. The existing interior of the home has been taken down to the framing and includes 100-amp electrical service, providing a solid starting point for your vision. Outdoor enthusiasts will enjoy everything this property has to offer. Fish for perch, bass, catfish, and snakeheads, or spend the day crabbing from your shoreline. Waterfowl hunters will enjoy the existing duck blind, while everyone will appreciate the stunning sunsets overlooking the water. Whether you're looking for a peaceful weekend escape, a hunting and fishing camp, or the site of your future waterfront cottage, this property offers an opportunity that's becoming increasingly difficult to find.

220 Kirbys Landing Rd, Millington

Listing courtesy of Select Land & Homes, LLC. Contact: (410) 708-0956
$899,000
3 Beds ⋅ 3 Baths
Escape to your own private Eastern Shore sanctuary! Nestled on 15.39 acres in Stevensville, 225 Batts Neck Road offers the ultimate blend of coastal convenience and secluded mountain-getaway. This stunning 3BR/2.5BA post-and-beam cabin welcomes you with a classic wrap-around porch and a cozy interior featuring a wood-burning stove—complete with a second fireplace rough-in for the upstairs lofted primary suite. The expansive layout includes an amazing living room and game area designed for hosting memorable family gatherings. The 15+ acres are an outdoor enthusiast's dream, featuring established walking and ATV trails, along with cleared open areas perfect for camping and firepits. Whether you are looking for a premier hunting retreat, a weekend getaway, or a permanent homestead with the potential to build a second home, this unique acreage delivers. Enjoy the best of the Eastern Shore: less than 2 miles from Matapeake Beach, 2.5 miles from Kentmorr Marina, and 4 miles from Bay Bridge Marina. Best of all, you are just 4 miles from the Bay Bridge for a seamless commute to Annapolis, Baltimore, or DC!

225 Batts Neck Rd, Stevensville

Listing courtesy of Real Broker, LLC - Annapolis. Contact: 8554500442
$395,000
3 Beds ⋅ 2 Baths
This charming ranch-style home, renovated in 2020, offers a perfect blend of modern comfort and classic appeal. With a thoughtfully designed living space, this residence features three inviting bedrooms and two full bathrooms, including a luxurious primary bath with upgraded countertops and a walk-in tiled shower. The heart of the home is the spacious eat-in kitchen, complete with stainless steel appliances, an island for casual dining, and a family room that flows seamlessly off the kitchen, making it ideal for gatherings. Natural light abounds and the recessed lighting & ceiling fans enhance the warm ambiance throughout. Step outside to enjoy the maintenance-free deck and porch, perfect for relaxing or entertaining while overlooking the level fenced rear yard. Abundant off-street paved parking for numerous boats, RV's & vehicles. Situated in a welcoming community, this home is surrounded by well-maintained parks and recreational areas, providing ample opportunities for outdoor activities including; boating, fishing/crabbing, cook-outs & swimming on the sandy beaches along the scenic Chesapeake Bay. With easy access to restaurants, shops and a friendly neighborhood atmosphere, this property is not just a house; it's a place to create lasting memories. Experience the comfort and community spirit that this lovely Stevensville home and Kent Island lifestyle has to offer!

105 Bobbit Ct, Stevensville

Listing courtesy of Beam Realty Group, Inc.. Contact: 4438656969
$669,900
3 Beds ⋅ 2 Baths
Welcome to your private Eastern Shore oasis at 116 Mallard Drive, Stevensville, MD 21666! This beautifully maintained and recently updated Cape Cod home sits on a rare 1.1-acre lot in a quiet, private neighborhood on Kent Island — one of the hardest-to-find lot sizes in this desirable area. Enjoy serene, protected views of Mallard Pond, where you can watch ducks glide across the water, sip morning coffee on the screened porch, and truly experience peaceful Kent Island living at its finest. Boasting 1,976 square feet of above-grade living space (built in 2000), this 3-bedroom, 2-bath home features thoughtful updates throughout. Enjoy new LVP flooring and carpet, a bright open-concept main level perfect for everyday living and entertaining, and a stunning kitchen with granite countertops and all new appliances. The spacious primary suite includes a luxurious soaking tub and walk-in closet, while two additional bedrooms and a full bath complete the main level. A 2-car garage and newer furnace add convenience and peace of mind. The standout feature is the large unfinished attic with electrical wiring and HVAC already extended — substantial, flexible space ready for your vision. Easily finish into additional bedrooms, a home office, playroom, or family suite. Outside, the expansive 1.1-acre lot delivers exceptional privacy and natural beauty, bordered by community-owned preserved woodlands and Mallard Pond that ensure your views remain undisturbed for years to come. Enjoy the screened porch overlooking the pond, low-maintenance exterior, low HOA fees of only $17 per month, and the incredible location on Kent Island — walk or bike to the public golf course, Kent Island Trail, waterfront parks, piers, and just minutes from Chesapeake Bay adventures, shopping, and dining. This updated home combines solid construction, modern finishes, low monthly costs, and a truly rare 1.1-acre private setting. Whether you’re looking for a peaceful full-time residence or a lifestyle property with room to grow, 116 Mallard Drive is a standout opportunity on Kent Island. Don’t miss it!

116 Mallard Dr, Stevensville

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

$73,000
Residential Lot For Sale in the charming town of Barclay! This property offers a peaceful rural setting while remaining conveniently located just minutes from Route 301. The partly wooded property provides a blend of natural beauty and privacy, creating an ideal backdrop for your future home. A private well will be required for water service, and public sewer is available and ready for connection, offering added convenience for new construction. Connection fee information has been provided in the attached documents for prospective buyers. Current sewer service fee is $43.87 per month. Enjoy small-town living with easy access to major commuting routes and the surrounding Eastern Shore amenities. Buyer to verify all utility connections, fees, and building requirements with the appropriate authorities.

105 Barclay Cutoff Rd, Barclay

Listing courtesy of Benson & Mangold, LLC. Contact: (443) 988-0483
$4,995,000
5 Beds ⋅ 5 Baths
Architect-designed contemporary waterfront home on nearly 18 private acres across two parcels with approximately 1,400 feet of shoreline on Greenwood Creek. Positioned to capture 180-degree western views, the property offers privacy, deep water, and a setting that is increasingly difficult to find on Maryland’s Eastern Shore. A custom pivoting front door creates a striking first impression and sets the tone for the home's thoughtful design. The home was designed to take advantage of the surrounding water and landscape, with floor-to-ceiling windows, open gathering spaces, and strong indoor-outdoor connections throughout. The kitchen opens to the main living areas and features a glass accordion door that connects directly to the screened porch, creating a seamless transition between indoor and outdoor spaces. The layout flows easily between the kitchen, dining areas, family room, porch, and pool area, making the home equally well suited for everyday living and entertaining. The primary suite is set apart from the rest of the home by a glass-enclosed walkway and includes a private office, large dressing room, en-suite bath, and private porch access. In addition to the primary suite, the main level includes three additional bedrooms, each with access to a private bathroom. The finished lower level includes a home theater, billiards room, bar area, workout room, additional bedroom and full bathroom, along with unfinished basement space for storage. Outdoor features include a solar-heated pool, private beach, and deep-water pier with two boat lifts. The protected shoreline and direct access to Eastern Bay make this an ideal property for boating and waterfront living. A three-bay outbuilding with workshop space and additional storage provides room for equipment, hobbies, or car and boat storage. Located just outside Queenstown, the property is convenient to Easton, Annapolis, Washington D.C., Baltimore, and Philadelphia while offering the privacy and pace of the Eastern Shore.

2800 Bennett Point Rd, Queenstown

Listing courtesy of TTR Sotheby's International Realty. Contact: 4106733344
$180,000
Don’t settle for less! If you’ve been searching for space, country living, and freedom from HOA restrictions — all while maintaining convenient access to major routes — this property deserves your attention. Situated on 9+ acres just approximately 3 miles from Rt. 301 in the quaint Town of Barclay, the possibilities here are endless. Partly wooded and rich with mature landscaping, this beautiful property features a charming small stream and offers the perfect setting to build your dream family home. ***Public sewer access is now available and at site for this property. You will just need to connect to your home when ready! As per QAC Director of Public Works, the "pump shell" is already installed on the property and the actual pump is ready to be installed when necessary. NO allocation fee is necessary for a single home on this property*** Current Sewer Service Fee is $73/mo. Looking for less acreage? This parcel may offer subdivision potential, subject to buyer due diligence. An existing trailer remains on the property and is uninhabitable — please do not enter. Trailer to be removed soon!

1420 Barclay Rd, Barclay

Listing courtesy of Benson & Mangold, LLC. Contact: (443) 988-0483
$2,850,000
5 Beds ⋅ 5 Baths
Set on Forty Five picturesque acres of prime agricultural land with extensive tillable acreage, this exceptional Five bedroom, Four and one half bath brick colonial blends timeless design with modern versatility and waterfront charm. Privately situated on a quiet cove just off the mouth of the Chester River, the property offers a rare combination of space, functionality, and lifestyle appeal. Inside, the home features a thoughtfully designed layout ideal for both everyday living and entertaining. A main-level en-suite provides excellent flexibility for multi-generational living or private guest quarters, while an additional upper-level en-suite enhances comfort and convenience for visitors. The spacious primary suite serves as a true retreat, complemented by well-proportioned secondary bedrooms and multiple full baths. Refined living spaces include a formal dining room, a dedicated home office perfect for remote work, and an inviting screened porch overlooking the water—an ideal setting to relax and take in the tranquil views. The nearly fully finished basement expands your living options with generous space for recreation, hobbies, or a workshop. Recent upgrades—including a new roof and septic system—offering peace of mind, while the 2-zone HVAC system ensures efficient year-round comfort. Outdoors, enjoy the in-ground pool surrounded by a patio, perfect for entertaining or unwinding, along with open acreage that offers endless possibilities for farming, equestrian use, or a private rural lifestyle. Complete with a Twocar garage and located in a highly desirable waterfront setting, this property presents a rare opportunity to own a versatile estate that balances luxury living, scenic beauty, and agricultural potential.

1810 Love Point Rd, Stevensville

Listing courtesy of Monument Sotheby's International Realty. Contact: (410) 525-5435
$459,900
3 Beds ⋅ 2 Baths
*BACK ON THE MARKET - BUYER HOME SALE CONTINGENCY FELL THROUGH! Welcome to this beautifully renovated and remodeled 3-bedroom, 2-bath home offering the perfect blend of modern style, comfort, and location. Designed with today’s lifestyle in mind, this home features a bright open floor plan with spacious living and dining areas that flow seamlessly into the stunning gourmet kitchen. The kitchen is a true showstopper with elegant quartz countertops, a large center island, and ample space for cooking, gathering, and entertaining. Both full bathrooms have been tastefully updated with ceramic tile finishes and brand-new high-end vanities. The spacious primary suite offers a private retreat with its own en-suite bathroom for added comfort and convenience. Step outside to enjoy the level front and backyard spaces, ideal for outdoor entertaining, gardening, play, or simply relaxing. Located just one block from the Chesapeake Bay, you’ll love the nearby neighborhood waterfront park featuring picnic areas and fishing access. Conveniently situated for commuters, this home offers easy access to the Eastern Shore beaches, Washington, DC, and Baltimore—making it the perfect place to enjoy coastal living with city convenience. Don’t miss this exceptional opportunity!

109 Birch Rd, Stevensville

Listing courtesy of Five Star Real Estate. Contact:

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

137 Tanners Point Dr, Stevensville

Listing courtesy of Coldwell Banker Realty. Contact: 4102638686
$1,375,000
4 Beds ⋅ 5 Baths
BEAUTIFUL 21 ACRE WATERFRONT ESTATE WITH OVER 400' OF WATER FRONTAGE AND SEPARATELY DEEDED DEEP WATER SLIP IS INCLUDED, SLIP #16 AT THE FAR LEFT END OF THE PIER RIGHT ACROSS THE STREET! APPROXIMATELY 6 CLEARED ACRES AND 15 WOODED ACRES. SPECTACULAR 3-STORY HOME WITH 4 LARGE BEDROOMS W/ENSUITE BATHROOMS. RECENT TOP QUALITY GOURMET KITCHEN RENOVATION W/GAS COOKTOP. IT'S AWESOME! ATTACHED 2-CAR GARAGE AND A MONSTROUS DETACHED GARAGE WITH ROOM FOR 6 MORE CARS. PLENTY OF STORAGE. BEAUTIFUL, PRIVATE INGROUND GUNITE POOL. CALL LISTING AGENT FOR MANY MORE AMENITIES. READ HOA DOCS IN DISCLOSURES. TRY TO GIVE 1-2 DAYS SHOWING NOTICE, PLEASE.

105 Port Ct, Grasonville

Listing courtesy of Douglas Realty LLC. Contact: (410) 255-3690
$2,428,725
161.85 acres with NO EASTMENT! Limited by only zoning and your imagination. About 97 tillable, on east and west sides of MD Route 213 between Centreville and Church Hill; 4 platted perk sites, and more potential. Communications Tower lease $837.32/month; In the Queen Anne's County "Opportunity Zone" tax breaks for permitted uses. No Easements! Chesapeake Bay Scenic Byway(Potential sale of easement); Hunting: Goose, Deer, Turkey, wood ducks; 1000+/- feet along both sides of Granny Findley Branch - surrounded by woodland filled with deer. Invest in the future, rent the farmland and hunting rights, farm it yourself, build your dream home no builder tie in.

Sparks Mill Corner - E&W Sparks Mill At Route 213 Rd, Centreville

Listing courtesy of Tidewater Properties. Contact:

$2,428,725
161.85 acres with NO EASTMENT! Limited by only zoning and your imagination. About 97 tillable, on east and west sides of MD Route 213 between Centreville and Church Hill; 4 platted perk sites, and more potential. Communications Tower lease $836.32/month; In the Queen Anne's County "Opportunity Zone" tax breaks for permitted uses. No Easements! Chesapeake Bay Scenic Byway(Potential sale of easement); Hunting: Goose, Deer, Turkey, wood ducks; 1000+/- feet along both sides of Granny Findley Branch - surrounded by woodland filled with deer. Invest in the future, rent the farmland and hunting rights, farm it yourself, build your dream home no builder tie in.

Sparks Corner Sparks Mill At Route 213 Rd, Centreville

Listing courtesy of Tidewater Properties. Contact: