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5135 Crosby Rd, Rock Hall
$5,900,000
6 Beds ⋅ 5 Baths
A true sportsman’s paradise and a family compound, this impressive 212 +/-acre farm offers breathtaking water views and unparalleled outdoor recreation. The solidly built, colonial style home is designed to capture the beauty of Davis Creek from nearly every room. The kitchen and dining area are perfectly positioned for waterfront entertaining, seamlessly flowing into the family room with gas fireplace and the sunroom. Expansive decks overlook the creek and the entrance to Lankford Bay. For more intimate gatherings, a formal dining room provides the perfect setting for cozy celebrations. Designed for convenience, the home features a main level en-suite bedroom and bath. Upstairs, the spacious primary suite includes an oversized closet and bathroom, accompanied by three additional guest rooms, two full bathrooms, plus an additional bedroom currently used as an office. Two of the guest bedrooms have access to the upstairs porch. There is bonus semi-finished space on the third floor. A dry basement offers ample storage. Boating enthusiasts will appreciate the multi-slip deep-water dock with 5 feet MLW, a 16,000 lb. boat lift and a jet ski lift. The property consists of three parcels. The main parcel is over 72 acres and includes the residence, barn, and outbuildings. There is an 82+ acre buildable parcel featuring a dock and a cleared buildable site with water views. The third buildable parcel is nearly 58-acres with established farmland and prime hunting grounds. The two additional parcels already have paid public sewer hook ups. Approximately 88 acres of woods. The farm is well-equipped for agriculture (111 tillable acres), premier hunting, and endless recreational opportunities. It includes a main pond, two impoundments, and rich wildlife habitat. Hunters will find the property loaded with deer, turkey, geese, and ducks. There are two, 6-man cinder block goose pits (oriented North/South and East/West) and six deer stands. This property is truly one of a kind. Whether you're looking for a private retreat, a working farm, or a premier hunting destination, this estate has it all. Schedule your private tour today!

5135 Crosby Rd, Rock Hall

Listing courtesy of TTR Sotheby's International Realty. Contact:

Selling Office: Select Land & Homes, LLC.

25440 Learman Rd, Chestertown
$3,000,000
3 Beds ⋅ 4 Baths
Welcome to the epitome of Eastern Shore waterfront luxury, offered for the first time in almost 60 years. This stunning 11-acre estate offers an unparalleled lifestyle, featuring 560 feet of prime water frontage on the Chester River and a private 140-foot dock with 7 feet of mean low water, perfect for all your adventures. ** The heart of this property is the beautifully renovated 3-bedroom, 2 full bath, 2 half bath main home, meticulously remodeled in 2018 with the highest quality materials and fixtures. The residence boasts sweeping water views from nearly every room, allowing you to enjoy picturesque sunrises Chester River. ** As you enter, you are greeted by a grand living room featuring a striking five-foot fireplace set within a soaring vaulted ceiling, creating a warm and inviting atmosphere. Expansive windows frame the breathtaking views and fill the space with natural light, enhancing the open-concept design that is perfect for both relaxing and entertaining. ** The gourmet kitchen is a chef's dream, equipped with top-of-the-line stainless steel appliances, custom cabinetry, an oversized island with seating, and elegant custom stone and wood countertops. This thoughtfully designed space allows for effortless meal preparation and entertaining. ** Retreat to the luxurious primary suite, a true sanctuary featuring its own private walled garden, offering a serene escape for relaxation and outdoor enjoyment. The suite also includes a cozy fireplace, perfect for creating a romantic ambiance. The spa-like bathroom is designed for ultimate relaxation, a spacious glass-enclosed double head shower, and dual vanities with exquisite finishes. A generous walk-in closet provides ample storage, ensuring organization and convenience. ** The outdoor living features of this luxurious estate are truly exceptional, designed to create an idyllic sanctuary for relaxation and entertainment. At the heart of the outdoor space is a stunning waterfront concrete pool, refurbished in 2018, offering a refreshing retreat on warm summer days while providing breathtaking views of the Chester River. Surrounding the home, the professionally designed landscaping enhances the natural beauty of the property, featuring lush gardens, vibrant plantings, and mature ornamental trees. The side patio, complete with a charming brick fire pit, invites gatherings with friends and family, perfect for cozy evenings under the stars. The poolside patio off the main living room makes alfresco dining a breeze. Additionally, the private walled garden serves as a tranquil oasis, offering a serene space to unwind amidst nature, making this outdoor area the perfect complement to the luxurious lifestyle this estate offers. ** Accommodate guests or staff in the charming 3-bedroom, 2-bath guest/caretaker's cottage, built in 2013. A spacious 2.5-bay workshop provides ample storage for your outdoor equipment and hobbies. ** This exceptional property seamlessly blends luxury and tranquility, offering a unique opportunity to own a piece of paradise on the Eastern Shore. Don’t miss your chance to experience the charm and elegance of this extraordinary waterfront estate!

25440 Learman Rd, Chestertown

Listing courtesy of TTR Sotheby's International Realty. Contact:

Selling Office: Coldwell Banker Realty.

33658 Golts Rd, Massey
$2,500,000
3 Beds ⋅ 2 Baths
Investment Opportunity is here! Kent County, Md farm offered with 207+/- acres total. The property is unencumbered by any preservation or similar easements such as MALPF or other conservation groups. A quality 1344 square foot rancher home with attached 728 square foot garage with a 216 square foot deck overlooking the pond and fields. The home was built around 1988 and a very substantial outbuilding for all of your outdoor and recreational toys, Tillable acres are estimated at 114+/- with great soil types for a variety of uses. A beautiful 4+/- acre Wildlife Pond for summer and winter recreation. The farm does offer a large second Well for future irrigation uses or winter impoundment uses in the fields east of the home. Exceptional Hunting can be found here with the estimated 88+/- acres of Woodlands with the area seeing frequent Deer Herds, Turkey and other Wildlife on many evenings. This property presents a high level of possibility to an investor willing to navigate the solar options. The presence of two main power feed lines transiting the land with relatively close substations in either direction an interested buyer should investigate the possibilities. As always, any interested buyer should perform their appropriate level of due diligence.

33658 Golts Rd, Massey

Listing courtesy of The Land Group. Contact:

Selling Office: The Land Group.

7989 Quaker Neck Rd, Chestertown
$1,900,000
5 Beds ⋅ 5 Baths
Price Improvement! Spectacular waterfront on the Chester River!! Words can't describe the uniqueness of this property. With the historic charm of an older home but high end modern upgrades, you will be living the life of luxury. Spacious rooms, magnificent views of the Chester River and your private dock with new boat lift, sandy beach, and stunning new saltwater pool. Exposed beams, scalamandre wallpaper, and multiple fireplaces. First floor owners suite featuring reclaimed pine flooring, private laundry area, walk-in closet, gas fireplace and remodeled bath with soaking tub. Second floor owner's suite with additional laundry area and remodeled bath. Breezeway to the garage. New irrigation system to all flower beds. New paint inside and out. House has had major remodels in 2000 and 2020. Town sewer. Not far from town, but the property has a private feel. Some interior images have been AI virtually staged for illustrative purposes. These images do not represent the property's current furnishings or decor.

7989 Quaker Neck Rd, Chestertown

Listing courtesy of Coldwell Banker Chesapeake Real Estate Company. Contact:

Selling Office: Long & Foster Real Estate, Inc..

11500 Possum Hollow Rd, Worton
$1,825,000
3 Beds ⋅ 4 Baths
89± Acres Prime Farmland • Exceptional Hunting • Private Pond • Luxury Country Living Experience the best of Maryland's Eastern Shore on this remarkable 89± acre sporting estate, where productive farmland, exceptional hunting, and refined country living come together in one extraordinary property. Perched atop a picturesque knoll overlooking a private fishing pond, this meticulously maintained estate offers breathtaking panoramic views, complete privacy, and a lifestyle few properties can match. The beautifully maintained 3-bedroom, 3.5-bath brick rancher has been thoughtfully designed for both comfortable everyday living and effortless entertaining. A welcoming foyer with hardwood flooring leads into spacious living areas filled with natural light. The impressive family room features vaulted ceilings, a dramatic floor-to-ceiling brick fireplace, and expansive windows showcasing spectacular views across the pond, fields, and surrounding countryside. The gourmet kitchen serves as the centerpiece of the home and features custom two-tone cabinetry, quartz countertops, a large center island, stainless steel appliances, subway tile backsplash, recessed lighting, luxury vinyl plank flooring, and abundant cabinet and workspace. A bright breakfast area overlooks the pond while the formal dining room provides an elegant setting for holiday gatherings and entertaining. The spacious primary suite offers peaceful views of the surrounding landscape and a private en-suite bath, while two additional bedrooms provide comfortable accommodations for family and guests. The full basement expands the home's living space with an impressive recreation room featuring a custom bar, making it the perfect gathering place after a day in the field or on the water. The unfinished portion is setup with a utility sink,stove for endless options and storage. Step outside onto the covered rear porch, where you'll enjoy morning coffee over looking the pond and unforgettable sunsets over the surrounding farmland. The land is equally impressive. Approximately 50 acres of productive tillable farmland, consisting primarily of highly desirable Matapeake and Sassafras soils, offer exceptional agricultural production and leasing opportunities. Approximately 30 acres of mature hardwoods provide outstanding wildlife habitat, creating one of the area's premier recreational properties. For sportsmen, this property is truly exceptional. The combination of agricultural fields, mature timber, and water creates ideal habitat for wildlife, offering excellent whitetail deer, wild turkey, and goose hunting. An established goose pit in a prime area provides outstanding waterfowl opportunities, along with a private pond. Additional improvements include a 30' x 40' pole barn with ample room for tractors, equipment, recreational vehicles, or workshop space, as well as a 16' x 24' open equipment shed. Beautiful landscaping, an oversized paved driveway, and meticulously maintained grounds further complement this exceptional estate. Whether you're seeking a productive farm, a premier hunting retreat, an income-producing investment, or a private family estate, this rare offering delivers an unmatched combination of luxury, recreation, and agricultural value. Property Features 89± Acres Beautiful 3 Bedroom | 3.5 Bath Brick Rancher Elevated Homesite with Panoramic Views Gourmet Kitchen Quartz Countertops & Custom Cabinetry Vaulted Great Room with Floor-to-Ceiling Brick Fireplace Hardwood Flooring Full Basement with Finished Recreation Room & Custom Bar Covered Rear Porch Approximately 50 Acres of Prime Tillable Land Predominantly Matapeake & Sassafras Soils Approximately 30 Acres of Mature Woodland Exceptional Deer, Turkey & Waterfowl Hunting Established Goose Pit 30' x 40' Pole Barn 16' x 24' Open Equipment Shed Beautifully Landscaped G

11500 Possum Hollow Rd, Worton

Listing courtesy of Taylor Properties. Contact:

Selling Office: Select Land & Homes, LLC.

17 N Chadwick Dr, Dover
$1,550,000
7 Beds ⋅ 7 Baths
CUSTOM-BUILT ELEGANCE CRAFTED FOR LUXURY Step into unmatched luxury in this stunning custom-built home with nearly 10,000 square-feet of living space. Exceptional craftsmanship, top-tier renovations, and the endless natural light of this home set a new standard for refined living. Every inch was thoughtfully designed with no expenses spared. Homes like this rarely come along in Kent County, DE! One of Delaware’s premier builders completed this unique all brick home as a true masterpiece for his own family in one of the area’s most desirable neighborhoods. The home offers an extraordinary blend of elegance, comfort, and modern sophistication. Quality and style shine at every turn. The property also boasts a brand-new, stone finished concrete resort-style heated saltwater pool, perfect for entertaining or relaxing in your own private oasis. Whether hosting gatherings or enjoying quite evenings at home, this residence delivers an unparalleled lifestyle. Adding to its versatility, the property includes a private studio apartment above the second garage, ideal as an in-law suite, guest quarters, or flexible space for generational living. This separate living area is fully equipped with its own mini-split, hot water heater, garage, private entrance, bathroom and sunroom. The home showcases an extensive array of high-end finishes! Highlights include: brand new kitchen with professional-grade Sub-Zero, Wolf and Cove appliances, Kohler fixtures, Anderson custom window, Restoration Hardware lighting features, Soapstone and Quartzite countertops and Marble backsplash. Smart switch technology in kitchen and basement. FX exterior uplighting designed by lighting specialists. Outstanding vehicle capacity with two 2-car garages (4 car capacity) and an additional carport with an extra wide driveway. Two-sided gas fireplace. Elegant dining room with 25-foot ceilings along with a study. Newly renovated 3,000 sq ft basement contains full bathroom, tile flooring, newly upgraded movie theater with Italian leather theater seats and complete surround sound, and a fully equipped gym with high-end cardio and professional strength training equipment. Three electrical panels, three zone HVAC, two on demand tankless hot water heaters, new irrigation system, and new charcoal water softener system. Hardwood floors throughout the home. You name it, this home has it! A rare opportunity to own a timeless residence of distinction, designed to impress!

17 N Chadwick Dr, Dover

Listing courtesy of The Moving Experience Delaware Inc. Contact:

Selling Office: Long & Foster Real Estate, Inc..

24241 Drayton Landing Dr, Worton
$1,450,000
3 Beds ⋅ 3 Baths
Waterfront living overlooking Still Pond Creek! Gently nestled into the woods on 5.67 acres of peace and nature, this special home is the ultimate dream getaway for relaxation and recreation. Enter this very private sanctuary surrounded by nature which offers a large, circular area accommodating parking for many guests. Upon entering the home, you will take in the elevated waterfront views from the light-filled great room with a soaring ceiling and a wall of windows. This space opens to a deck as well as a large screened-in porch that is the heart of the home all summer. It features a seating area to spend hours relaxing and enjoying the sounds of nature in complete privacy, and a dining table to watch the changing colors of the sky every evening. The open floor plan of the home is ideal for entertaining and offers waterfront views from nearly every room. The home features three bedrooms, three full baths, a loft office, a wood-burning fireplace, and a walk-out lower-level area with additional guest space and recreation area, including one of the full baths and additional large storage areas. Upstairs the primary suite is very private, with a renovated bath and beautiful water views. The home has many upgrades throughout, including beautiful hardwood decking on the decks and porch and new two-zone heating and cooling.  The property is surrounded by a native pawpaw patch, and each summer you will await the arrival of the many zebra swallowtail butterflies they host.  In the morning, wake to a beautiful sunrise over the creek, and listen to the many songbirds that pass through the property. The nearby eagle nest often leads to seeing them soaring overhead. At the waterfront there is a private sand beach where no other homes can be seen in any direction. Sunset is also a special time to sit down on the dock and enjoy the evenings. Stone steps lead down the path to the dock and water, first over a short raised boardwalk and then through a magical moss section, arriving at the private pier with a 8000lb boat lift, electricity, and approximately 4.0 ft MLW. Still Pond Creek, ideal for kayaking, fishing, boating, paddle boarding, wake boarding, and more, makes this a water lover’s dream home. The location is ideal - just around the corner from the bay yet just beyond the section frequented by those coming to experience the charm and deep anchorage of the creek. Located in the highly sought-after community of Kinnaird’s Point with a community boat launch, beach, and pavilion, high-speed internet, and located just outside of Chestertown - 59 miles to Annapolis, 87 miles to DC, and 86 miles to Philadelphia. Historic Chestertown on the Chester River, home of Washington College, is located just 10 miles away and offers great restaurants, bars, shopping, an outdoor Farmer’s Market, annual celebrations including the Chestertown Tea Party, Sultana Downrigging Festival, and much more. Please do not drive in the driveway without an appointment. The property is available furnished, excluding art and personal items. The structure sits well above the water and is not in a flood zone. Full home, septic, and water reports available online.  Owner is a licensed PA realtor.

24241 Drayton Landing Dr, Worton

Listing courtesy of Coldwell Banker Realty. Contact:

Selling Office: Coldwell Banker Chesapeake Real Estate Company.

19 Lake Crest Dr, Milford
$1,410,000
4 Beds ⋅ 5 Baths
"The Dream Home" – A spectacular contemporary custom-built estate where luxury, craftsmanship, and resort-style living come together in the prestigious Haven Lake Estates. From the moment you arrive, this extraordinary residence makes a lasting impression. A gated entrance with elegant wrought-iron fencing opens to a lighted asphalt driveway accented with pavers, leading to the recently constructed, climate-controlled three-car detached garage. Every detail has been thoughtfully designed to create a truly one-of-a-kind property. Step inside the grand two-story foyer featuring soaring ceilings, a sparkling chandelier, and a dramatic curved staircase leading to the second-floor catwalk overlooking the main living area. Just beyond, a sun-filled sitting room provides the perfect retreat to enjoy a quiet morning with coffee and the day's news, while the formal dining room is ideal for hosting memorable holiday gatherings and elegant dinner parties. The gourmet kitchen is a chef's dream, showcasing a newly expanded center island with abundant storage, custom cabinetry with accent lighting, hard-surface countertops, a farmhouse sink, and brand-new stainless steel appliances, including a gas range with a drop-down exhaust. The adjoining breakfast area overlooks the beautifully landscaped backyard, creating the perfect setting for casual dining. The breathtaking great room serves as the heart of the home, highlighted by a stunning floor-to-ceiling custom built-in entertainment wall and an impressive wall of windows that frame picturesque views of the outdoor living space, heated in-ground pool, wooded backdrop, and gently winding brook. The privately situated first-floor primary suite is a luxurious retreat featuring separate walk-in closets and a spa-inspired bath complete with a walk-in shower, porcelain soaking tub, double vanity, and a modern digital mirror. The second level offers a private guest suite with its own full bath and walk-in closet, two additional generously sized bedrooms, and another full bathroom. A spacious bonus room with its own private bath, built-in entertainment center, and adjoining office with custom workspace provides endless possibilities as a home office, media room, guest quarters, or recreation space. The finished lower level is equally impressive, featuring a dedicated theater room with surround sound and recessed lighting, along with additional flexible space perfect for a home gym, yoga studio, craft room, or game room. Ample storage with built-in shelving completes the basement. Designed for both entertaining and everyday enjoyment, the outdoor living spaces rival a private resort. The fenced backyard features a recently installed heated in-ground pool, expansive paver patio, newer deck, fully equipped outdoor kitchen with plumbing, pergola, relaxing hot tub, fire pit, gazebo, playground area, and generous green space for gardening or recreation. Recently installed sod and professional landscaping further enhance the beauty of this remarkable property. Additional highlights include a main-level laundry room with overhead cabinetry, an attached three-car garage, a recently replaced roof and siding, a tankless water heater, and meticulous maintenance throughout. Conveniently located within easy driving distance of major metropolitan areas, Delaware's award-winning beaches, and popular coastal destinations, this exceptional estate offers the perfect blend of luxury, privacy, and convenience. More than just a home, it is a lifestyle—a private oasis you'll never want to leave.

19 Lake Crest Dr, Milford

Listing courtesy of The Watson Realty Group, LLC. Contact:

Selling Office: Compass.

13840 Mill Creek Ln, Galena
$1,275,000
3 Beds ⋅ 2 Baths
Do you crave peace, privacy and waterfront? Escape to your own slice of paradise in this meticulously maintained 3-bedroom, 2-bathroom estate, where luxury meets sustainability. Nestled on a beautifully wooded and private 1.58 acre lot, this home is a true sanctuary for nature lovers and water enthusiasts alike. The interior features a thoughtful layout designed for comfort, but the true magic lies in the resort-style amenities. Unwind after a long day in your private sauna or soak in the hot tub while overlooking your lush surroundings. Summer days are best spent lounging by the sparkling inground pool or enjoying the breeze from the screened porch and expansive deck. Winter evenings snuggle up in front of the wood burning fireplace inserts in the living room and the den, or in front of the fire in your bedroom. Unwind by walking the meditation labyrinth. Situated on the upper portion of Mill Creek, this property boasts a private pier, providing a gateway to the Sassafras River for boating, fishing, or simply enjoying the tranquil water views. The detached 2-car garage is more than just storage; it features a finished loft with full bathroom perfect for a home office, guest suite, or creative studio. The fully owned solar panel system heats the inground swimming pool. Thirteen miles from tax-free shopping in Middletown, DE. Whether you’re looking for a full-time residence or a weekend getaway, this property offers an unparalleled blend of peace, privacy, and outdoor adventure. PLEASE RESPECT SELLER'S PRIVACY. NO DRIVE BY. PLEASE REQUEST SHOWING APPOINTMENT.

13840 Mill Creek Ln, Galena

Listing courtesy of EXP Realty, LLC. Contact:

Selling Office: EXIT Preferred Realty.

29313 Glencoe Rd, Kennedyville
$1,100,000
3 Beds ⋅ 2 Baths
Welcome to 29313 Glencoe Rd Kennedyville. Experience waterfront living at its finest with this well-maintained 3-bedroom, 2-bath ranch home. Designed for comfort and relaxation, the home features just a few of the amenities of a bright sunroom, and a spacious walk-out basement. Outside, you'll find two detached garages with additional storage above, offering ample room for vehicles, hobbies, and equipment. An original out building, called the fish house offers a unique perspective of the area. A newer pier with a boat lift and floating dock provides easy access to the water, making it perfect for boating, fishing, or simply enjoying life on the Sassafras River & other tributaries. The property boasts approximately 200 feet of bulkheaded shoreline and a small sandy beach, creating the quintessential waterfront retreat. Elevated views stretch down the Sassafras River and across Freeman Creek, where you can watch abundant wildlife throughout the seasons. Begin each day with breathtaking sunrises over the Sassafras River. This exceptional waterfront property offers the perfect blend of comfort, convenience, and scenic beauty.

29313 Glencoe Rd, Kennedyville

Listing courtesy of Gunther-McClary Real Estate. Contact:

Selling Office: Gunther-McClary Real Estate.

12400 Woods Rd, Worton
$1,095,000
3 Beds ⋅ 2 Baths
More than a home, this is truly a recreational property and boater's paradise. Nestled on a promontory point above Still Pond Creek and just a short drive from historic Chestertown, this house was designed by iconic architect Peter Newlin to provide a coziness and connection to nature that embodies the Eastern Shore lifestyle. Jutting out from the bulkhead designed the Army Corps of Engineers, the dock awaits you for boating adventures and quick access to the Chesapeake Bay directly from the protected waters of Still Pond Creek. Life slows down while appreciating the water and wildlife from the deck. The spacious screened porch is perfect for crab feasts with unmatched views. A lane for vehicles and also a winding walking path leads you down to the private beach where memories and tans are made. The great room boasts vaulted ceilings with exposed beams and flows out with sliders and a side door to the screened porch and deck for indoor-outdoor living. A trio of picture windows and the wood burning fireplace are perfect for cuddling up and looking out over the water on cool winter days. There are two bedrooms and full bath on the main level and a primary suite with ensuite bathroom, vaulted ceilings, and walk in cedar closet upstairs. The large walkout basement is the perfect space for the kayaks, bikes, and other toys that come with living on the Eastern Shore. The land itself is low maintenance but expansive allowing for calming hikes and relaxation in nature. Invest wisely in this irreplaceable asset less than 2 hours from Washington DC, Philadelphia, and Baltimore.

12400 Woods Rd, Worton

Listing courtesy of Coldwell Banker Chesapeake Real Estate Company. Contact:

Selling Office: BHHS Fox & Roach - Hockessin.

26230 Royal Swan Rd, Still Pond
$1,050,000
3 Beds ⋅ 4 Baths
Some Day has arrived. Tucked within 38 rolling acres near Betterton Beach and the Chesapeake Bay, this private equestrian retreat offers space to slow down, reconnect with nature, and awaken to birdsong across the fields. The inviting three-bedroom, three-and-a-half-bath home features a first-floor primary suite, private study, and an attached two-car garage with a loft roughed in for a potential caretaker’s or guest suite. Paddocks, riding trails, a sand ring, five-stall stable, and four-bay machine shed complete the equestrian setting, while more than half the acreage is currently tilled under a farm lease. Peaceful and private, Some Day Farm is a place to breathe deeply and live fully. The property is an estate and is being sold as is.

26230 Royal Swan Rd, Still Pond

Listing courtesy of Coldwell Banker Chesapeake Real Estate Company. Contact:

Selling Office: Heroes Real Estate.

26230 Royal Swan Rd, Still Pond
$1,050,000
3 Beds ⋅ 4 Baths
Some Day has arrived. Tucked within 38 rolling acres near Betterton Beach and the Chesapeake Bay, this private equestrian retreat offers space to slow down, reconnect with nature, and awaken to birdsong across the fields. The inviting three-bedroom, three-and-a-half-bath home features a first-floor primary suite, private study, and an attached two-car garage with a loft roughed in for a potential caretaker’s or guest suite. Paddocks, riding trails, a sand ring, five-stall stable, and four-bay machine shed complete the equestrian setting, while more than half the acreage is currently tilled under a farm lease. Peaceful and private, Some Day Farm is a place to breathe deeply and live fully. This property is an estate and is being sold as is.

26230 Royal Swan Rd, Still Pond

Listing courtesy of Coldwell Banker Chesapeake Real Estate Company. Contact:

Selling Office: Heroes Real Estate.

231 Richard Dr, Chestertown
$1,050,000
5 Beds ⋅ 3 Baths
Experience the best of waterfront living just steps outside of the heart of Downtown Chestertown. Only a few blocks from shops, restaurants, the bustling farmers market, art galleries, annual festivals, and the vibrant cultural life that defines this beloved Eastern Shore community, this exceptional property offers a rare opportunity to enjoy riverfront living with walkable in-town convenience. * With five (plus) bedrooms accommodating up to fourteen guests and three full baths, the home is designed for comfort, flexibility, and enjoyment. Multiple indoor and outdoor gathering spaces make it ideal for those seeking a full-time residence, a weekend retreat, a multi-generational destination, or a strong investment property with outstanding rental potential. * On the main level, a cozy den with a wood-burning fireplace captures Chester River views, creating a warm and welcoming spot to relax after a day on the water. Additional living spaces provide room for groups to spread out—whether entertaining, working remotely, or simply taking a quiet moment to unwind. The primary suite offers its own private vantage point with a picture window overlooking the pool and riverfront—perfect for greeting the sunrise or watching wildlife glide across the water. * Outdoor living is where this property truly shines. Enjoy a covered patio for shaded summer crab feasts, a large deck with a stone fireplace for crisp evenings, and an in-ground pool that looks out toward the shore. With immediate water access, you’ll launch kayaks, paddle boards, and jet skis right from your backyard—ideal for embracing the river lifestyle. A two-car attached garage provides convenient storage for gear, bikes, and all the water toys. It could also be the perfect space to keep your street legal golf cart which the Town Of Chestertown now allows! * Your new home is also just a short walk from the full-service Chestertown Marina with the potential for a transferable slip—already paid through the 2026 boating season—ensuring you can enjoy hassle-free access to Chester River fun. Additionally, it's a quick ride to the Chester River Yacht & Country Club, where you can indulge in 18 holes of golf, relax by the pool, enjoy happy hour or meals at the full restaurant and bar, and partake in a host of other fantastic member benefits. * Whether you’re making it your full-time home, your getaway from the city, or your next strategic investment, this property delivers the best of Chestertown living—waterfront, walkable, and wonderfully welcoming. Embrace a lifestyle of leisure and convenience in this exceptional location.

231 Richard Dr, Chestertown

Listing courtesy of TTR Sotheby's International Realty. Contact:

Selling Office: RE/MAX Chesapeake.

25209 Wymont Park Rd, Worton
$1,050,000
3 Beds ⋅ 1 Baths
Wymont Park Waterfront Living! Welcome to Wymont Park, a charming waterfront community on Still Pond Creek that perfectly embodies Eastern Shore living. This one-of-a-kind home has a rich history—originally built as a cozy bungalow, it has grown over the years through thoughtful additions and, most recently, a complete remodel that transformed it into the stunning residence it is today. With three levels facing the water, this home is designed to maximize the views and the experience of creekside living. Step through the main entrance and you’re greeted by original post-and-beam details that flow into an open living, kitchen, and dining area. These spaces lead seamlessly to a screened porch overlooking lush gardens, your private dock, and breathtaking Still Pond sunsets. The primary suite on the second floor offers a private walk-out deck, the perfect retreat for morning coffee or evening stargazing. With 3 bedrooms, 2 full baths, and 2 powder rooms, there’s ample space for both relaxation and entertaining. The walk-out lower level provides additional sitting areas and opens to outdoor living spaces, including a unique wood-fired oven crafted from the home’s original fieldstone. This area is surrounded by gardens and the relaxing sounds of the fish ponds and waterfalls with peaceful seating to enjoy. Every update and remodel has been carried out with care, blending modern comforts with the character and charm of the home’s history. From sunrise coffee on the deck to sunset views over the creek, this property offers the ultimate Eastern Shore lifestyle.

25209 Wymont Park Rd, Worton

Listing courtesy of Doug Ashley Realtors, LLC. Contact:

Selling Office: Keller Williams Legacy.

5980 Lawton Ave, Rock Hall
$1,010,000
3 Beds ⋅ 3 Baths
Welcome to Silly Manor, a Chesapeake Bay-front property with an abundance of coastal charm and panoramic views. This home is perfectly situated on the coveted Lawton Avenue, one of Kent County's most sought-after neighborhoods. Enjoy stunning sunsets all year-round and direct access to the dynamic waters of the Chesapeake Bay. The open living and dining space offer spectacular views of the Chesapeake. The kitchen opens up to the patio and garden, and has a spacious island for entertaining. The home was designed with a first-floor primary suite, offering convenient (and hard-to-find) one-floor living. There are two additional bedrooms and a full bath on the second floor. Watch the boats glide in and out of Swan Creek all day long, or enjoy the cozy fireplace during the colder months, with the Bay sparkling just outside. This is one of the larger parcels on Lawton, and it boasts a detached, oversized one-car garage, along with a separate workshop. The hardscape patio and stone walkways are perfect for al fresco dining or simply soaking in the surrounding beauty. The home feels very private, yet is located just minutes from many marinas, restaurants, shops and the Rock Hall Beach. This is the perfect weekend retreat or full-time home!

5980 Lawton Ave, Rock Hall

Listing courtesy of Gunther-McClary Real Estate. Contact:

Selling Office: Coldwell Banker Realty.

319 Wheatleys Pond Rd, Clayton
$1,000,000
4 Beds ⋅ 4 Baths
Nestled on a serene 5.6-acre lot, this exquisite ranch-style residence offers a harmonious blend of luxury and comfort, perfect for those seeking an exclusive lifestyle. Built in 2018, this home showcases impeccable craftsmanship and modern design, ensuring a warm and inviting atmosphere throughout. Step inside to discover a thoughtfully designed interior featuring luxury vinyl plank flooring and plush carpeting that exudes elegance. The heart of the home is the spacious kitchen, complete with upgraded countertops, an expansive island, and a spacious pantry, making it a culinary haven for entertaining guests. The open floor plan seamlessly connects the kitchen to the dining area and living area, where a cozy gas fireplace serves as a focal point, inviting relaxation on chilly evenings. The primary suite is a true retreat, boasting his/hers walk-in closets and a spa-like bathroom with a walk-in shower, providing a tranquil escape. Convenience is key with a main floor mud room/laundry area, enhancing the ease of daily living. Step outside to your private oasis, where a screened porch and lovely deck invite you to unwind while overlooking the beautifully landscaped garden and pond. The in-ground pool, surrounded by a fenced area, offers a perfect spot for summer gatherings or peaceful afternoons basking in the sun. The property also features a shed for additional storage, invisible fencing, an underground irrigation system to maintain the lush greenery. With views of the pond and lovely garden, this home is a nature lover's dream, providing a tranquil backdrop for everyday life. The partly wooded lot offers privacy and a sense of seclusion, while still being conveniently located near local amenities. Parking is a breeze with an attached garage, a detached garage, and a paved driveway, ensuring plenty of space for vehicles and recreational toys. This property is not just a home; it's a lifestyle, offering the perfect blend of luxury, comfort, and natural beauty. Experience the tranquility and elegance that this remarkable residence has to offer.

319 Wheatleys Pond Rd, Clayton

Listing courtesy of Samson Properties of DE, LLC. Contact:

Selling Office: Keller Williams Realty Central-Delaware.

1895 Windswept Cir, Dover
$940,000
4 Beds ⋅ 5 Baths
Experience the unparalleled beauty of waterfront living in this exceptional estate, perfectly positioned to capture breathtaking panoramic river views from nearly every room. Nestled within Windswept, one of Kent County's most prestigious waterfront communities, this meticulously transformed home offers an extraordinary blend of timeless elegance, sophisticated design, and resort-style living. Encompassing more than 5,100 square feet, this remarkable home features four spacious bedrooms and five luxurious bathrooms, thoughtfully designed to maximize both comfort and the spectacular waterfront setting. From the moment you enter, soaring ceilings, walls of oversized windows, and rich wide-plank hardwood floors create a light-filled interior where the ever-changing water views become part of the home's design. A dramatic spiral staircase serves as the architectural focal point, making an unforgettable first impression. Designed for both everyday living and grand entertaining, the chef's kitchen is a masterpiece of form and function, showcasing custom cabinetry, granite countertops, professional-grade appliances, an expansive center island, and its own inviting fireplace. Flowing seamlessly into the spectacular great room, a soaring floor-to-ceiling stone fireplace anchors the space while endless views of the water provide a breathtaking backdrop for every gathering. The main-level primary suite is a private sanctuary where you'll wake each morning to tranquil river vistas. A dedicated study, elegant formal living and dining spaces, and thoughtfully designed entertaining areas complete the first floor, all oriented to embrace the home's stunning waterfront location. Upstairs, three beautifully appointed en-suite bedrooms provide exceptional comfort and privacy for family and guests, while a versatile loft offers the perfect setting for a media room, lounge, or additional retreat. Outside, your own private waterfront resort awaits. A heated saltwater Gunite pool, relaxing hot tub, and expansive terraced patios create an extraordinary outdoor living experience designed to celebrate the home's spectacular setting. Whether enjoying your morning coffee as the sun rises over the water, entertaining beneath colorful evening skies, or simply relaxing to the peaceful sights and sounds of the river, every moment here feels like a vacation. This is more than a luxury home—it's a waterfront lifestyle defined by breathtaking views, exceptional craftsmanship, and unforgettable sunsets. Opportunities like this are exceedingly rare. Schedule your private tour today and experience one of Kent County's finest waterfront properties.

1895 Windswept Cir, Dover

Listing courtesy of Burns & Ellis Realtors. Contact:

Selling Office: Keller Williams Realty Central-Delaware.

58 Mulberry Dr, Frederica
$850,000
4 Beds ⋅ 3 Baths
Rare find! Don't miss this remarkable contemporary home with direct beach access and breathtaking views of Delaware Bay. It is nestled on the bayfront of Bowers Beach - a hidden gem with a secluded sandy beach and many community events. You can enjoy walking to the beach from your backyard and watching the dolphins right from your back porch. Can it get any better? Yes! Because the house itself has so much to offer! The home has an open floor plan with a flexible living room space that opens to the kitchen, 4 generously sized bedrooms, and 3 full bathrooms. The spacious kitchen features self-closing cabinets, an island, two sinks, new GE Cafe double oven range and dishwaher, Samsung Flex refrigerator with navy blue doors, tile backsplash, and a separate wet bar with a new beverage refrigerator. The inviting living room has access to the expansive deck overlooking the bay and a cozy gas fireplace for chilly nights. The primary bedroom suite has its own deck, a luxurious bathroom with a whirlpool tub, walk-in shower, a makeup vanity station, and a walk-in closet. The home also has a two-car garage and a laundry room featuring front-loading new LG washer and dryer and a laundry sink. The wish-list additions also include LVP flooring throughout the house, Anderson windows and doors, a generator that is powered by propane. Recent upgrades include new electric water heater and new Coastal heat pumps (electric). The electric stove could be converted back to gas. Multiple decks and plenty of windows overlook picturesque views of the Bay and shoreline wildlife. The town of Bowers Beach offers public boat ramps with generous parking, restaurants, seasonal fine dining dockside, a maritime museum, and a beach perfect for kayaking, fishing, and swimming. If this sounds like your dream home and lifestyle - why wait? - Schedule your tour today!

58 Mulberry Dr, Frederica

Listing courtesy of Patterson-Schwartz-Rehoboth. Contact:

Selling Office: Bryan Realty Group.