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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.

$2,500,000

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.

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.

$1,900,000

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.

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..

$1,825,000

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

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.

$1,550,000

5 Beds ⋅ 3 Baths

7761 Broad Neck Rd, Chestertown

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

Selling Office: Davis Real Estate, Inc..

$1,450,000

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.

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.

$1,400,000

This sale price includes the real estate only at 173 Sassafras St, Millington, MD. There's 19,656 SF of office and production/warehouse area in three structures on 1.92 acres of land. Light Industrial Zoning allows for many uses. Approximately 6,000 SF of office area plus lab space and about 13,656 SF of production area in two steel buildings. The property has public water and sewer, 208V - 3 phase electric service, and high speed internet. Security fencing around the warehouse/production area. Possible seller financing. This property is in an excellent location within a two hour drive to Baltimore, Washington DC, Philadelphia, Wilmington, and more.

173 Sassafras St, Millington

Listing courtesy of Rock Hall Properties Real Estate. Contact:

Selling Office: Non Subscribing Office.

$1,275,000

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.

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.

$1,100,000

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.

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.

$1,095,000

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.

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.

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.

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.

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.

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.

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.

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.

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.

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.

$1,010,000

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!

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.

$918,000

Completely renovated four-bedroom home offering an ideal Upper Eastern Shore location where Swantown Creek meets the Sassafras River. This private retreat features convenient first-floor living, with water views from the living room, dining area, kitchen, and two primary bedrooms. The home is enhanced by a spacious deck overlooking the water, a finished basement, outdoor shower, hot tub, fire pit and a detached storage shed. Set in a park-like setting, the property is just minutes from Middletown, DE and the bypass, providing easy access to northern destinations while still enjoying the charm of of nearby Georgetown and Chesapeake City.

Completely renovated four-bedroom home offering an ideal Upper Eastern Shore location where Swantown Creek meets the Sassafras River. This private retreat features convenient first-floor living, with water views from the living room, dining area, kitchen, and two primary bedrooms. The home is enhanced by a spacious deck overlooking the water, a finished basement, outdoor shower, hot tub, fire pit and a detached storage shed. Set in a park-like setting, the property is just minutes from Middletown, DE and the bypass, providing easy access to northern destinations while still enjoying the charm of of nearby Georgetown and Chesapeake City.

31902 Swantown Dr, Galena

Listing courtesy of Gunther-McClary Real Estate. Contact:

Selling Office: Chesapeake Real Estate Associates, LLC.

$825,000

Exceptional custom-built 2018 one-level home on 2.28 private acres in the highly sought-after Prestwick community, ideally nestled just off the Chester River Yacht & Country Club. This thoughtfully designed residence offers a seamless blend of comfort, elegance, and functionality, featuring an open-concept layout with soaring ceilings and abundant natural light throughout. The gourmet kitchen showcases timeless off-white cabinetry, granite countertops in warm earthy tones, and a coordinating backsplash, all opening effortlessly to the expansive great room anchored by a striking stone fireplace—perfect for both everyday living and entertaining. Enjoy multiple outdoor living options including a screened porch, rear porch, and patio—each offering peaceful wooded views and backing to open space for a truly private, tranquil setting that invites you to unwind and explore. The home features rich hardwood flooring, tile, fresh carpet, and fresh neutral paint throughout. The spacious primary suite, privately situated, offers a tray ceiling, two walk-in closets, and a luxurious en-suite bath, while three additional bedrooms and two full baths are thoughtfully positioned on the opposite side—ideal for guests, family, or a dedicated home office. Additional highlights include a welcoming front porch, partially finished basement with half bath and exterior access, and flexible space for recreation, hobbies, or future customization. The attached 2-car garage is complemented by a stairway off the laundry room leading to unfinished space above—perfect for expansion or storage. A standout feature is the detached custom 3-car garage equipped with a car-lift, work benches, cabinets, a mini-split system and unfinished upper level—an incredible opportunity for additional living space. Surrounded by nature, this property offers a rare combination of privacy, craftsmanship, and subtle details that are best experienced in person. Don’t miss this rare opportunity! Built by Alton E. Darling Construction.

4 Beds ⋅ 4 Baths

Exceptional custom-built 2018 one-level home on 2.28 private acres in the highly sought-after Prestwick community, ideally nestled just off the Chester River Yacht & Country Club. This thoughtfully designed residence offers a seamless blend of comfort, elegance, and functionality, featuring an open-concept layout with soaring ceilings and abundant natural light throughout. The gourmet kitchen showcases timeless off-white cabinetry, granite countertops in warm earthy tones, and a coordinating backsplash, all opening effortlessly to the expansive great room anchored by a striking stone fireplace—perfect for both everyday living and entertaining. Enjoy multiple outdoor living options including a screened porch, rear porch, and patio—each offering peaceful wooded views and backing to open space for a truly private, tranquil setting that invites you to unwind and explore. The home features rich hardwood flooring, tile, fresh carpet, and fresh neutral paint throughout. The spacious primary suite, privately situated, offers a tray ceiling, two walk-in closets, and a luxurious en-suite bath, while three additional bedrooms and two full baths are thoughtfully positioned on the opposite side—ideal for guests, family, or a dedicated home office. Additional highlights include a welcoming front porch, partially finished basement with half bath and exterior access, and flexible space for recreation, hobbies, or future customization. The attached 2-car garage is complemented by a stairway off the laundry room leading to unfinished space above—perfect for expansion or storage. A standout feature is the detached custom 3-car garage equipped with a car-lift, work benches, cabinets, a mini-split system and unfinished upper level—an incredible opportunity for additional living space. Surrounded by nature, this property offers a rare combination of privacy, craftsmanship, and subtle details that are best experienced in person. Don’t miss this rare opportunity! Built by Alton E. Darling Construction.

25475 Turnberry Ct, Chestertown

Listing courtesy of Taylor Properties. Contact:

Selling Office: Unrepresented.

$750,000

Perfectly situated home in move-in condition, views of glorious Sassafras from almost every room. 1st Fl multiple options for eating, relaxing, and entertaining, and powder room. Large master bedroom with bath joins four other bedrooms, two baths and laundry room on second floor, approached by a classic staircase with upstairs wrap around landing. Irrigated landscaping t/o with amazing patio.

5 Beds ⋅ 3 Baths

Perfectly situated home in move-in condition, views of glorious Sassafras from almost every room. 1st Fl multiple options for eating, relaxing, and entertaining, and powder room. Large master bedroom with bath joins four other bedrooms, two baths and laundry room on second floor, approached by a classic staircase with upstairs wrap around landing. Irrigated landscaping t/o with amazing patio.

29030 Belchester Rd, Kennedyville

Listing courtesy of Cross Street Realtors LLC. Contact:

Selling Office: Non Subscribing Office.

$745,000

Thoughtfully designed and built in 2017, this private retreat sits on nearly 7 peaceful acres just 5 minutes north of historic Chestertown and 30 minutes from Middletown, Delaware. Surrounded by farmland and mature landscaping, the property offers the perfect balance of modern comfort, flexibility, and quiet Eastern Shore living. The heart of the home is the stunning chef’s kitchen featuring cathedral ceilings, top-of-the-line appliances, a large center island, and separate pantry. The kitchen flows into the family room with a propane fireplace and French doors leading to the rear screened porch where you can take in views of the yard and surrounding countryside. The main level primary suite offers a spacious bathroom and oversized dressing room closet. A second main level bedroom provides access to a full bathroom and dedicated office. An additional bonus room on the main level offers flexibility for dining, hobbies, crafts, or running a business from home. Upstairs, you’ll find two additional bedrooms and a full bathroom. The partially finished walkout basement expands the living space even further with a full bathroom and flexible recreation or guest area with direct access to the backyard. Additional features include an oversized detached two-car garage with attic storage above, numerous garden beds throughout the property, and a peaceful setting that offers privacy, space, and room to truly enjoy the outdoors.

4 Beds ⋅ 4 Baths

Thoughtfully designed and built in 2017, this private retreat sits on nearly 7 peaceful acres just 5 minutes north of historic Chestertown and 30 minutes from Middletown, Delaware. Surrounded by farmland and mature landscaping, the property offers the perfect balance of modern comfort, flexibility, and quiet Eastern Shore living. The heart of the home is the stunning chef’s kitchen featuring cathedral ceilings, top-of-the-line appliances, a large center island, and separate pantry. The kitchen flows into the family room with a propane fireplace and French doors leading to the rear screened porch where you can take in views of the yard and surrounding countryside. The main level primary suite offers a spacious bathroom and oversized dressing room closet. A second main level bedroom provides access to a full bathroom and dedicated office. An additional bonus room on the main level offers flexibility for dining, hobbies, crafts, or running a business from home. Upstairs, you’ll find two additional bedrooms and a full bathroom. The partially finished walkout basement expands the living space even further with a full bathroom and flexible recreation or guest area with direct access to the backyard. Additional features include an oversized detached two-car garage with attic storage above, numerous garden beds throughout the property, and a peaceful setting that offers privacy, space, and room to truly enjoy the outdoors.

11122 Boyer Ln, Worton

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

Selling Office: Coldwell Banker Chesapeake Real Estate Company.

$740,000

Coveted WATERFRONT in charming RockHall — the Pearl of the Chesapeake. This beautifully updated home offers plenty of space for family and friends with 4 bedrooms and 3 full baths, all wrapped in natural landscaping that provides privacy inside and out. Enjoy peaceful water views of Swan Creek / Haven Creek Cove from the deck or sunroom, or launch your boat or kayak directly from your private dock. The open main-level floor plan, combined with a sunroom just off the living room, creates an ideal setting for entertaining or relaxing while surrounded by nature and abundant wildlife. Whether you’re looking for a vacation getaway, retirement retreat, or a strong VRBO opportunity, this property checks every box. Just a short walk down the street to dinner, shops, and Rock Hall’s beloved town festivals — there’s always something happening in this vibrant waterfront community.*Check out the daily flock of Geese and Ducks that land in the Cove! *All kitchen appliances & laundry purchased new in 2022* Newer Heat pump 2022

Coveted WATERFRONT in charming RockHall — the Pearl of the Chesapeake. This beautifully updated home offers plenty of space for family and friends with 4 bedrooms and 3 full baths, all wrapped in natural landscaping that provides privacy inside and out. Enjoy peaceful water views of Swan Creek / Haven Creek Cove from the deck or sunroom, or launch your boat or kayak directly from your private dock. The open main-level floor plan, combined with a sunroom just off the living room, creates an ideal setting for entertaining or relaxing while surrounded by nature and abundant wildlife. Whether you’re looking for a vacation getaway, retirement retreat, or a strong VRBO opportunity, this property checks every box. Just a short walk down the street to dinner, shops, and Rock Hall’s beloved town festivals — there’s always something happening in this vibrant waterfront community.*Check out the daily flock of Geese and Ducks that land in the Cove! *All kitchen appliances & laundry purchased new in 2022* Newer Heat pump 2022

20992 Rock Hall Ave, Rock Hall

Listing courtesy of Chaney Homes, LLC. Contact:

Selling Office: Keller Williams Select Realtors of Cambridge.

$730,000

Experience the warmth and charm of in-town living in this beautiful residence in Chestertown's Historic District. Just a few blocks from the waterfront, shops, galleries, and restaurants, it offers the perfect balance of walkability and tranquility on one of the district's quietest streets. The thoughtfully designed layout makes excellent use of every square foot, while tasteful updates fill the home with natural light. A spacious screened porch extends from the dining room, offering a peaceful place to relax and enjoy the character of the neighborhood. The fenced backyard is a gardener's dream, featuring lush landscaping, vibrant plantings, and beautiful hardscaping that create a private outdoor sanctuary. A rear entrance with off-street parking adds everyday convenience while preserving the home's charming streetscape. This exceptional historic property offers an outstanding lifestyle less than two hours from Washington, DC, and Philadelphia.

Experience the warmth and charm of in-town living in this beautiful residence in Chestertown's Historic District. Just a few blocks from the waterfront, shops, galleries, and restaurants, it offers the perfect balance of walkability and tranquility on one of the district's quietest streets. The thoughtfully designed layout makes excellent use of every square foot, while tasteful updates fill the home with natural light. A spacious screened porch extends from the dining room, offering a peaceful place to relax and enjoy the character of the neighborhood. The fenced backyard is a gardener's dream, featuring lush landscaping, vibrant plantings, and beautiful hardscaping that create a private outdoor sanctuary. A rear entrance with off-street parking adds everyday convenience while preserving the home's charming streetscape. This exceptional historic property offers an outstanding lifestyle less than two hours from Washington, DC, and Philadelphia.

210 N Queen St, Chestertown

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

Selling Office: Coldwell Banker Chesapeake Real Estate Company.

$725,000

Built in 1780/1840, "Highcroft" is in the heart of the Historic District near the Chester River. A rare in-town property that offers a 2-car garage with a second floor and a long driveway for tons of off-street parking. 3 bedrooms, 4 full baths and 1 half bath. Primary bedroom has his and hers private baths. 8.2 kw solar array on the garage. EV level 2 charger. Easy room flow from front to back for entertaining. Just steps to restaurants, bars, and shops. This is an ultra efficient "green" house.

3 Beds ⋅ 5 Baths

Built in 1780/1840, "Highcroft" is in the heart of the Historic District near the Chester River. A rare in-town property that offers a 2-car garage with a second floor and a long driveway for tons of off-street parking. 3 bedrooms, 4 full baths and 1 half bath. Primary bedroom has his and hers private baths. 8.2 kw solar array on the garage. EV level 2 charger. Easy room flow from front to back for entertaining. Just steps to restaurants, bars, and shops. This is an ultra efficient "green" house.

407 High St, Chestertown

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

Selling Office: Cross Street Realtors LLC.

$705,000

***OFFER DEADLINE FOR HIGHEST & BEST IS MONDAY, 8/10 @ 5PM--SELLER RESERVES THE RIGHT TO ACCEPT AN OFFER AT ANY POINT PRIOR TO THE DEADLINE AT THEIR SOLE DISCRETION*** This exceptional property offers classic charm, thoughtful updates, and a highly desirable location in a neighborhood where homes rarely become available. No trendy updates here-timeless, classic elegance and warmth invite you home and will stand the test of time. Situated on a beautifully landscaped 0.88-acre lot with mature trees, this home is just minutes to the Country Club (close enough to walk) and a few minutes drive to downtown Chestertown. The main level features a spacious and well-designed layout with 3 bedrooms, 2 full baths, and 1 half bath. The renovated kitchen is complete with a large island, new granite countertops, lovely cabinetry, gas cooking, under-cabinet lighting, and recessed lighting. A bright dining room with custom built-ins and bay window flows into the formal living room with French doors. The great room offers a warm and inviting space with a gas fireplace, beautiful brick surround and chimney hugged by timeless built-ins on each side, with another bright bay window. The main-level primary suite includes access to the rear deck, a renovated en-suite bath with pocket door, and a walk-in closet. Two additional bedrooms, a full hall bath, laundry room, and a convenient half bath complete the main level. The second level provides incredible flexibility with two finished rooms, a bonus room that could serve as a potential 4th bedroom and another room, ideal for an office, recreation, or hobby space. An additional half bath is located on the upper level, and an extensive unfinished storage space & room is awaiting your vision. Additional features include a basement and crawlspace, water softener system, reverse osmosis kitchen faucet, sump pump, and dehumidifier, attached 2 car garage & potting shed, just to name a few. Outdoor living is equally impressive with a covered front porch, large rear deck, lawn irrigation, and meticulously maintained landscaping. A rare opportunity in a sought-after location—schedule your showing soon. Please do not enter the property without an appointment. Most of the furnishings and decor are negotiable and available for purchase. Being Sold As-Is.

***OFFER DEADLINE FOR HIGHEST & BEST IS MONDAY, 8/10 @ 5PM--SELLER RESERVES THE RIGHT TO ACCEPT AN OFFER AT ANY POINT PRIOR TO THE DEADLINE AT THEIR SOLE DISCRETION*** This exceptional property offers classic charm, thoughtful updates, and a highly desirable location in a neighborhood where homes rarely become available. No trendy updates here-timeless, classic elegance and warmth invite you home and will stand the test of time. Situated on a beautifully landscaped 0.88-acre lot with mature trees, this home is just minutes to the Country Club (close enough to walk) and a few minutes drive to downtown Chestertown. The main level features a spacious and well-designed layout with 3 bedrooms, 2 full baths, and 1 half bath. The renovated kitchen is complete with a large island, new granite countertops, lovely cabinetry, gas cooking, under-cabinet lighting, and recessed lighting. A bright dining room with custom built-ins and bay window flows into the formal living room with French doors. The great room offers a warm and inviting space with a gas fireplace, beautiful brick surround and chimney hugged by timeless built-ins on each side, with another bright bay window. The main-level primary suite includes access to the rear deck, a renovated en-suite bath with pocket door, and a walk-in closet. Two additional bedrooms, a full hall bath, laundry room, and a convenient half bath complete the main level. The second level provides incredible flexibility with two finished rooms, a bonus room that could serve as a potential 4th bedroom and another room, ideal for an office, recreation, or hobby space. An additional half bath is located on the upper level, and an extensive unfinished storage space & room is awaiting your vision. Additional features include a basement and crawlspace, water softener system, reverse osmosis kitchen faucet, sump pump, and dehumidifier, attached 2 car garage & potting shed, just to name a few. Outdoor living is equally impressive with a covered front porch, large rear deck, lawn irrigation, and meticulously maintained landscaping. A rare opportunity in a sought-after location—schedule your showing soon. Please do not enter the property without an appointment. Most of the furnishings and decor are negotiable and available for purchase. Being Sold As-Is.

7903 Radcliffe Rd, Chestertown

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

Selling Office: Unrepresented.

$695,000

Toad Hall, as the current owners affectionately call it, is located in a natural wooded setting on Fairlee Creek in Great Oak Estates just minutes from the Chesapeake Bay. Peaceful water views from almost every room in the home create the feeling of living in a tree house, and the dock is just steps away down the hillside - no flood insurance needed. Enter the house through a split foyer with a few steps up to the main level and into the great room with the central kitchen, dining and living areas. The master suite is located on one end of the main level and features a large walk-in tile shower and a small private deck. The other end of the main level features a vaulted sunroom, a great spot to commune with nature or host the family crab feast. The lower walk out level offers a family room with a wood stove, two bedrooms, a full bath, a laundry room, and outdoor access. 2.5-3' MLW Buyer to verify. See Documents for Seller updates plus info on Association benefits. New roof added in 2021 and a BAT septic system was installed in 2023. Property has been well maintained but is being sold AS IS.

Toad Hall, as the current owners affectionately call it, is located in a natural wooded setting on Fairlee Creek in Great Oak Estates just minutes from the Chesapeake Bay. Peaceful water views from almost every room in the home create the feeling of living in a tree house, and the dock is just steps away down the hillside - no flood insurance needed. Enter the house through a split foyer with a few steps up to the main level and into the great room with the central kitchen, dining and living areas. The master suite is located on one end of the main level and features a large walk-in tile shower and a small private deck. The other end of the main level features a vaulted sunroom, a great spot to commune with nature or host the family crab feast. The lower walk out level offers a family room with a wood stove, two bedrooms, a full bath, a laundry room, and outdoor access. 2.5-3' MLW Buyer to verify. See Documents for Seller updates plus info on Association benefits. New roof added in 2021 and a BAT septic system was installed in 2023. Property has been well maintained but is being sold AS IS.

10087 John Carvill Rd, Chestertown

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

Selling Office: RE/MAX Chesapeake.

118 Little Harbor Way Unit 202, Chestertown

$660,000

Welcome to 118 Little Harbor Way #202, a beautifully reimagined waterfront condo offering effortless living and sweeping panoramic views of the Chester River. Located in the highly desirable Chester River Landing community, this second-floor, 3-bedroom, 2-bath residence delivers the perfect blend of modern luxury, low maintenance, and classic Eastern Shore charm. Completely taken down to the studs and thoughtfully rebuilt, the condo feels brand new from top to bottom. The open floor plan is filled with soft, natural light and showcases wide-plank wood flooring, a cozy gas fireplace, and uninterrupted river views from the main living areas. The stunning kitchen features white quartz countertops and backsplash, stainless steel appliances, and a seamless flow for both everyday living and entertaining. The primary suite is a true retreat, complete with a walk-in closet and a spa-like tiled shower with multiple shower heads, including a rainfall feature. Both bathrooms are finished with timeless, high-quality materials, creating a clean, classic, and calming feel throughout. Step out onto the private balcony and take in peaceful, north-facing river views with soft, consistent light throughout the day. It is ideal for relaxing, reading, or simply watching boats drift by without the glare of direct sun. This is waterfront living at its most comfortable and serene. Additional features include elevator access to the second floor, a one-car garage, and a deeded boat slip, approximately 4 feet MLW. The community offers a pool, fishing pier, and marina with floating docks, along with beautifully maintained grounds featuring oyster shell walking paths and a firepit. The marina area also includes a community grill and multiple tables, perfect for outdoor dining and gathering. Flood insurance is not currently required for this second-floor unit, contributing to overall affordability. Buyers are encouraged to perform their own due diligence and verify any insurance requirements. Ideally located within walking distance to historic downtown Chestertown, and just a short drive to golf, dining, and the yacht club at Chester River Yacht and Country Club, this condo is perfectly suited for those looking to downsize, simplify, or secure a refined second home on the water. Move in ready, thoughtfully updated, and designed for relaxed coastal living, this is Eastern Shore living at its finest.

Welcome to 118 Little Harbor Way #202, a beautifully reimagined waterfront condo offering effortless living and sweeping panoramic views of the Chester River. Located in the highly desirable Chester River Landing community, this second-floor, 3-bedroom, 2-bath residence delivers the perfect blend of modern luxury, low maintenance, and classic Eastern Shore charm. Completely taken down to the studs and thoughtfully rebuilt, the condo feels brand new from top to bottom. The open floor plan is filled with soft, natural light and showcases wide-plank wood flooring, a cozy gas fireplace, and uninterrupted river views from the main living areas. The stunning kitchen features white quartz countertops and backsplash, stainless steel appliances, and a seamless flow for both everyday living and entertaining. The primary suite is a true retreat, complete with a walk-in closet and a spa-like tiled shower with multiple shower heads, including a rainfall feature. Both bathrooms are finished with timeless, high-quality materials, creating a clean, classic, and calming feel throughout. Step out onto the private balcony and take in peaceful, north-facing river views with soft, consistent light throughout the day. It is ideal for relaxing, reading, or simply watching boats drift by without the glare of direct sun. This is waterfront living at its most comfortable and serene. Additional features include elevator access to the second floor, a one-car garage, and a deeded boat slip, approximately 4 feet MLW. The community offers a pool, fishing pier, and marina with floating docks, along with beautifully maintained grounds featuring oyster shell walking paths and a firepit. The marina area also includes a community grill and multiple tables, perfect for outdoor dining and gathering. Flood insurance is not currently required for this second-floor unit, contributing to overall affordability. Buyers are encouraged to perform their own due diligence and verify any insurance requirements. Ideally located within walking distance to historic downtown Chestertown, and just a short drive to golf, dining, and the yacht club at Chester River Yacht and Country Club, this condo is perfectly suited for those looking to downsize, simplify, or secure a refined second home on the water. Move in ready, thoughtfully updated, and designed for relaxed coastal living, this is Eastern Shore living at its finest.

118 Little Harbor Way Unit 202, Chestertown

Listing courtesy of Benson & Mangold, LLC. Contact:

Selling Office: Doug Ashley Realtors, LLC.

$650,000

Classic Rock Hall craftsman home expanded and updated with luxury amenities. This is one of the largest homes on south Hawthorne, on almost an acre of land. One of the first homes built on Hawthorne, the home and property has been lovingly cared for and expanded by previous and current owners. Three bedrooms plus two full renovated baths offer plenty of room to relax. The large detached garage is a workshop paradise. All this is just steps from Rock Hall harbor and close to marinas and restaurants.

Classic Rock Hall craftsman home expanded and updated with luxury amenities. This is one of the largest homes on south Hawthorne, on almost an acre of land. One of the first homes built on Hawthorne, the home and property has been lovingly cared for and expanded by previous and current owners. Three bedrooms plus two full renovated baths offer plenty of room to relax. The large detached garage is a workshop paradise. All this is just steps from Rock Hall harbor and close to marinas and restaurants.

5786 S Hawthorne Ave, Rock Hall

Listing courtesy of Rock Hall Properties Real Estate. Contact:

Selling Office: TTR Sotheby's International Realty.

$640,000

Beautifully Updated Home in a Serene Setting! Welcome to this stunning home filled with thoughtful improvements and timeless charm. The spacious Florida room overlooks a private, beautifully landscaped backyard — your own personal oasis. This room offers unlimited views of the back yard, which was designed in collaboration with a professional landscaper, this garden is a delight in every season and a true haven for butterflies and hummingbirds. You will delight in an outdoor sitting area under a lovely shade tree. The main level features gleaming hardwood floor, a semi-open floor plan with a cozy fireplace perfect for cool evenings, and abundant natural light that creates a calming atmosphere throughout. The large primary suite offers comfort and convenience, and there is the option for a second bedroom on the main level. Current owners have opted to make that room a large office, and it features two closets. The kitchen is a dream — spacious enough for a large island and a generous breakfast area that easily fits a full-sized table. There is a mural border that shows scenes of historic Chestertown. Pantry and plenty of storage. Upstairs, you’ll find two large bedrooms and a full hall bath, ideal for guests or loved ones. Each bedroom offers walk-in storage — no attic ladders needed! Solar operated fans keep the attic spaces cool. Additional highlights include leased solar panels which have been paid out, a large garage with ample storage, additional storage shed with electric and water. , and a fantastic location just minutes from the Chester River and the Chester River Yacht and Country Club. Two zone for heating and cooling. Come see this charming home for yourself — it’s the perfect blend of beauty, comfort, and thoughtful design!