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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.

$2,100,000

Gobbler Hill, circa 1858 with an addition built in 1989, sits like a jewel atop one of the highest points in Kent County. Listed on the National Historic Registry, the transitional architecture is an excellent example of late Greek Revival to early Italianate. The property consists of four parcels totaling over 65 acres. Wildlife abounds on the fields of native prairie grasses, wild flowers, woods, approximately 20 tilled acres and a large pond. Impeccable attention was payed to maintaining the historic character of both the interior and exterior. From the Lincrusta wall covering, 19th century faux wood finishing, plaster medallions, white and sugar pine wood floors and crown molding on the 11 ft. ceilings to the monumental copper roof, the thoughtful restoration is stunning. The newer addition beautifully blends into the original section adding modern conveniences and natural light. The library boasts black walnut bookshelves constructed by a local craftsman. Well maintained grounds offer gardens, mature trees, a classic poured concrete in ground pool with inlaid tile and stunning views. This unique, lovingly restored piece of Kent County history is now looking for a new steward to guide it into its next chapter.

6 Beds ⋅ 5 Baths

Gobbler Hill, circa 1858 with an addition built in 1989, sits like a jewel atop one of the highest points in Kent County. Listed on the National Historic Registry, the transitional architecture is an excellent example of late Greek Revival to early Italianate. The property consists of four parcels totaling over 65 acres. Wildlife abounds on the fields of native prairie grasses, wild flowers, woods, approximately 20 tilled acres and a large pond. Impeccable attention was payed to maintaining the historic character of both the interior and exterior. From the Lincrusta wall covering, 19th century faux wood finishing, plaster medallions, white and sugar pine wood floors and crown molding on the 11 ft. ceilings to the monumental copper roof, the thoughtful restoration is stunning. The newer addition beautifully blends into the original section adding modern conveniences and natural light. The library boasts black walnut bookshelves constructed by a local craftsman. Well maintained grounds offer gardens, mature trees, a classic poured concrete in ground pool with inlaid tile and stunning views. This unique, lovingly restored piece of Kent County history is now looking for a new steward to guide it into its next chapter.

10121 Fairlee Rd, Chestertown

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

We are in a multiple offer situation. Seller will review all offers on Monday, August 18th. Offers are due to the listing agent by 4pm. 12530 Dads Desire Lane in Still Pond Md offers 158 acres of land and a three bedroom ranch house. 123 acres of the 158 are currently being farmed. The additional acreage is treed and offers amazing opportunities for hunting. The original farm house and barns were removed years ago, but can be rebuilt (buyer to confirm with Kent County). There is a Verizon tower on the property that shares the annual tax bill and pays the seller annually. The land lease agreement for the tower has a First Right of Refusal, within 30 days, for any offer made and accepted by the seller. All contracts will be contingent on this land lease agreement stipulation. However, the agreement is in the last term and a new agreement will be needed, and negotiated, with the new owners. (Buyers to confirm with the tower company). The property does have a Conservation Plan in place which dictates the terms of the acres that are currently farmed. All due diligence will need to be done by the buyer within the first 30 days. No showings will be allowed without a written pre-approval or proof of funds. All offers will be considered. The property will be open on Friday, August 15th from 10am-12pm for potential buyers to come and walk the property, review the conservation plans, land lease agreements with Verizon, and speak to the Listing Agent.

$2,000,000

3 Beds ⋅ 1 Baths

We are in a multiple offer situation. Seller will review all offers on Monday, August 18th. Offers are due to the listing agent by 4pm. 12530 Dads Desire Lane in Still Pond Md offers 158 acres of land and a three bedroom ranch house. 123 acres of the 158 are currently being farmed. The additional acreage is treed and offers amazing opportunities for hunting. The original farm house and barns were removed years ago, but can be rebuilt (buyer to confirm with Kent County). There is a Verizon tower on the property that shares the annual tax bill and pays the seller annually. The land lease agreement for the tower has a First Right of Refusal, within 30 days, for any offer made and accepted by the seller. All contracts will be contingent on this land lease agreement stipulation. However, the agreement is in the last term and a new agreement will be needed, and negotiated, with the new owners. (Buyers to confirm with the tower company). The property does have a Conservation Plan in place which dictates the terms of the acres that are currently farmed. All due diligence will need to be done by the buyer within the first 30 days. No showings will be allowed without a written pre-approval or proof of funds. All offers will be considered. The property will be open on Friday, August 15th from 10am-12pm for potential buyers to come and walk the property, review the conservation plans, land lease agreements with Verizon, and speak to the Listing Agent.

12530 Dads Desire Ln, Still Pond

Listing courtesy of Compass. Contact:

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.

$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..

$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..

$1,550,000

**Exquisite Waterfront Retreat on Chester River** Welcome to 7961 Quaker Neck Road, Chestertown, MD – an elegant and modern sanctuary nestled on the coveted Chester River, offering a rare opportunity to own a completely remodeled waterfront property. This exceptional home encompasses five beautifully appointed bedrooms, four luxurious bathrooms, and sits gracefully on nearly half an acre of pristine land. As you step inside, you're greeted by an abundance of natural light streaming through perfectly placed skylights, highlighting the breathtaking waterfront views. The main level features an expansive living room adorned with a cozy fireplace, seamlessly flowing into a chef's dream kitchen. This culinary masterpiece boasts an expansive island with seating for eight, upgraded cabinetry and countertops, a deep farmhouse sink, and top-of-the-line stainless steel appliances, including two dishwashers, two wall ovens, a gas range, microwave, refrigerator, and a wine fridge. Every detail has been meticulously crafted to showcase the stunning water views. The adjoining sunroom offers a serene space to unwind, while the recreation room provides ample space for entertainment and leisure. The main level also includes three spacious bedrooms, one with an ensuite, and an additional full bathroom. Upstairs, discover two more bedrooms, each with its own en suite, and a primary bedroom that features expansive windows and access to a private deck, perfect for savoring the tranquil water views. Outside, the peaceful backyard beckons you to relax and enjoy the serene beauty of the Chester River. A recently constructed dock, less than three years old, provides easy access to the water, while two outdoor showers offer convenience after a day of river adventures. The large detached garage ensures ample storage space for all your needs. This home is enhanced by a range of modern upgrades, including newer windows, skylights, and doors, all completed in 2022, along with freshly painted exteriors and a Rinnai water heater. Three working fireplaces, two wood-burning and one gas, create inviting spaces to gather on cool evenings. Additional amenities include a whole house generator, two whole house dehumidifiers, and a fully remodeled interior designed for ultimate relaxation and enjoyment. Located just minutes from Historic Chestertown, this property allows you to enjoy the charm of small-town living with access to a variety of shops, coffee houses, and bakeries. Experience the perfect blend of elegance and modern comfort in this meticulously curated waterfront retreat. Homes like this are truly a rare find.

5 Beds ⋅ 4 Baths

**Exquisite Waterfront Retreat on Chester River** Welcome to 7961 Quaker Neck Road, Chestertown, MD – an elegant and modern sanctuary nestled on the coveted Chester River, offering a rare opportunity to own a completely remodeled waterfront property. This exceptional home encompasses five beautifully appointed bedrooms, four luxurious bathrooms, and sits gracefully on nearly half an acre of pristine land. As you step inside, you're greeted by an abundance of natural light streaming through perfectly placed skylights, highlighting the breathtaking waterfront views. The main level features an expansive living room adorned with a cozy fireplace, seamlessly flowing into a chef's dream kitchen. This culinary masterpiece boasts an expansive island with seating for eight, upgraded cabinetry and countertops, a deep farmhouse sink, and top-of-the-line stainless steel appliances, including two dishwashers, two wall ovens, a gas range, microwave, refrigerator, and a wine fridge. Every detail has been meticulously crafted to showcase the stunning water views. The adjoining sunroom offers a serene space to unwind, while the recreation room provides ample space for entertainment and leisure. The main level also includes three spacious bedrooms, one with an ensuite, and an additional full bathroom. Upstairs, discover two more bedrooms, each with its own en suite, and a primary bedroom that features expansive windows and access to a private deck, perfect for savoring the tranquil water views. Outside, the peaceful backyard beckons you to relax and enjoy the serene beauty of the Chester River. A recently constructed dock, less than three years old, provides easy access to the water, while two outdoor showers offer convenience after a day of river adventures. The large detached garage ensures ample storage space for all your needs. This home is enhanced by a range of modern upgrades, including newer windows, skylights, and doors, all completed in 2022, along with freshly painted exteriors and a Rinnai water heater. Three working fireplaces, two wood-burning and one gas, create inviting spaces to gather on cool evenings. Additional amenities include a whole house generator, two whole house dehumidifiers, and a fully remodeled interior designed for ultimate relaxation and enjoyment. Located just minutes from Historic Chestertown, this property allows you to enjoy the charm of small-town living with access to a variety of shops, coffee houses, and bakeries. Experience the perfect blend of elegance and modern comfort in this meticulously curated waterfront retreat. Homes like this are truly a rare find.

7961 Quaker Neck Rd, Chestertown

Listing courtesy of Compass. Contact:

Selling Office: Compass.

$1,524,900

Chesapeake Bay Waterfront with Breathtaking Views. Experience exceptional waterfront living in this custom-built 5,240 sq ft residence, beautifully situated on an elevated bluff in the sought-after Great Oak Community of Chestertown, Maryland. Offering 5 bedrooms and 3.5 baths, this remarkable home captures sweeping Chesapeake Bay views and unforgettable sunsets from nearly every room. The property features 150 feet of riprap-protected shoreline and direct water access via a brand-new private 140ft pier complete with lighting, water service in four locations, a 12,000-lb boat lift, and two jet ski lifts—perfect for boating and waterfront recreation. Inside, the home impresses with 9-foot ceilings and hardwood floors throughout most of the main level. Designed for entertaining, the gourmet kitchen showcases luxury appliances, a distinctive chef’s cutting-board countertop, and new LVP flooring. The grand great room is a true showpiece, featuring a floor-to-ceiling brick wood-burning fireplace, vaulted shiplap pine ceiling, exposed beams, and views of the Bay! Additional living spaces include an elegant formal dining room, a spacious gathering room, and a casual dining area highlighted by a gas fireplace. The first-floor primary suite offers privacy and comfort with a walk-in closet and an updated bath featuring new flooring, a corner soaking tub, and dual vanities. Two additional bedrooms, a full bath, and a laundry room complete the main level. The second floor provides two generously sized bedrooms, a large living area, a full bath, and an 18’ x 22’ unfinished bonus room/man cave with a separate staircase offering access to the garage or exterior—ideal for future expansion or customization. Notable features include a new roof, an oversized two-car garage with workbench, a small basement housing a state-of-the-art temperature- and humidity-controlled wine cellar, a Culligan whole-house water filtration system, and two hot water heaters. One of the home’s most captivating spaces is the expansive screened-in porch, stretching across much of the waterfront side of the home. With three ceiling fans and panoramic Chesapeake Bay views, it offers the perfect setting for relaxing or entertaining year-round. Whether you’re seeking a serene waterfront retreat or a home designed for memorable gatherings, this exceptional coastal property delivers. Just minutes from historic Chestertown, home to Washington College, waterfront dining, farmers’ markets, parks, festivals, and river cruises. Conveniently located near Safe Harbor Great Oak Marina and approximately 90 minutes from Washington, D.C. and Philadelphia. Schedule your private showing and experience Chesapeake Bay living at its finest

5 Beds ⋅ 4 Baths

Chesapeake Bay Waterfront with Breathtaking Views. Experience exceptional waterfront living in this custom-built 5,240 sq ft residence, beautifully situated on an elevated bluff in the sought-after Great Oak Community of Chestertown, Maryland. Offering 5 bedrooms and 3.5 baths, this remarkable home captures sweeping Chesapeake Bay views and unforgettable sunsets from nearly every room. The property features 150 feet of riprap-protected shoreline and direct water access via a brand-new private 140ft pier complete with lighting, water service in four locations, a 12,000-lb boat lift, and two jet ski lifts—perfect for boating and waterfront recreation. Inside, the home impresses with 9-foot ceilings and hardwood floors throughout most of the main level. Designed for entertaining, the gourmet kitchen showcases luxury appliances, a distinctive chef’s cutting-board countertop, and new LVP flooring. The grand great room is a true showpiece, featuring a floor-to-ceiling brick wood-burning fireplace, vaulted shiplap pine ceiling, exposed beams, and views of the Bay! Additional living spaces include an elegant formal dining room, a spacious gathering room, and a casual dining area highlighted by a gas fireplace. The first-floor primary suite offers privacy and comfort with a walk-in closet and an updated bath featuring new flooring, a corner soaking tub, and dual vanities. Two additional bedrooms, a full bath, and a laundry room complete the main level. The second floor provides two generously sized bedrooms, a large living area, a full bath, and an 18’ x 22’ unfinished bonus room/man cave with a separate staircase offering access to the garage or exterior—ideal for future expansion or customization. Notable features include a new roof, an oversized two-car garage with workbench, a small basement housing a state-of-the-art temperature- and humidity-controlled wine cellar, a Culligan whole-house water filtration system, and two hot water heaters. One of the home’s most captivating spaces is the expansive screened-in porch, stretching across much of the waterfront side of the home. With three ceiling fans and panoramic Chesapeake Bay views, it offers the perfect setting for relaxing or entertaining year-round. Whether you’re seeking a serene waterfront retreat or a home designed for memorable gatherings, this exceptional coastal property delivers. Just minutes from historic Chestertown, home to Washington College, waterfront dining, farmers’ markets, parks, festivals, and river cruises. Conveniently located near Safe Harbor Great Oak Marina and approximately 90 minutes from Washington, D.C. and Philadelphia. Schedule your private showing and experience Chesapeake Bay living at its finest

10800 Cliff Rd, Chestertown

Listing courtesy of Taylor Properties. Contact:

Selling Office: RE/MAX Chesapeake.

$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.

$1,435,000

Here's an opportunity to own an established assisted living facility (The Golden Rule) in the popular resort town of Rock Hall, MD. Currently licensed for 8 beds, with application complete for 3 additional beds, this facility has been operated by the current owners since it was built in 1999. The original 3BR/2 bath brick and cedar ranch home was built in 1986, with the 2,000+ sq.ft. assisted living addition constructed in 1999. An additional resident suite was built in 2004 for a total of 4,096 sq.ft. of living space. This bucolic setting features a pond and flowering gardens on 1.16 acres. Residents and visitors enjoy birdwatching in the sunroom and gentle breezes on the rear deck. All business inventory and equipment conveys. Other possible uses include a bed & breakfast operation or a residence with echo housing. This lovely property is 0.25 mile from the Rock Hall public beach and 0.25 mile from the harbor. Looking for a successful business and home combination - this is it.

20806 Bayside Ave, Rock Hall

Listing courtesy of Rock Hall Properties Real Estate. Contact:

Selling Office: Dream Realty, Inc..

$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.

$1,270,000

Public Auction held Onsite at 10434 Big Stone Road Millington, MD. Auction Date: Saturday November 22nd at 10am. Auction conducted by Witman Auctioneers, Inc. SELLING ABSOLUTE TO THE HIGHEST BIDDER AT or ABOVE OPENING BID OF $1,000,000.00. *** UPDATED*** 150.5 Acres in total. 3 Separate Parcels being sold in its entirety. Fantastic opportunity to own Kent County, MD farm ground. Approximately 130 acres tillable ground, Approximately 18 Acres wooded for Hunting or Recreation, 2.2 Acres Enrolled in CRP. There is an older farm house and equipment sheds/ buildings on property. Buildings and House need replaced or completely restored. Farm ground is currently leased by farmer till December 2026 for $132/ Per Acre, Written Contract/Lease in place. This farm has approximately 2.2 acres enrolled in CRP program. This farm is not enrolled in any other agriculture easement or preservation. Parcel 1 is 138 acre farm with older farm house and buildings zoned Agricultural , Parcel 2 is 9.1 Acre lot zoned Community Residential with 2 deeded separate lots and no improvements, Parcel 3 is 3.4 Acre lot zoned Community Residential with 1 deeded lot. Recent boundary survey, metes and bounds completed in 2025. Real estate appraisal completed in 2023. Great location only 12 minutes from MD-301, major route to Wilmington, DE. 8 minutes from town of Millington, Millington Hardware near by. 19 Minutes to Chestertown, MD. Auction Terms and Conditions: Property Sold in As-Is Condition, $100,000.00 non-refundable deposit due on auction day with certified check made payable to Witman Auctioneers, Inc., 30 Day Settlement, Buyer pays all Transfer and Settlement Costs. Broker/ Realtor Participation being offered. All Realtors/ Brokers Must be registered 48 hours prior to auction date and time. Broker/ Realtor form is an attachment on MLS. Property Inspection Dates: Monday, November 3rd 2pm-4pm, Sunday November 9th 12noon-2pm, Thursday November 13th 2pm-4pm. Property will also be available to preview auction day November 22nd 8:30am-10am.

10434 Big Stone Rd, Millington

Listing courtesy of Streett Hopkins Real Estate, LLC. Contact:

Price is the starting bid for a Ten-X auction to be held online from December 15-17. Pre-auction offers are being considered. Contact listing agent for details. Radcliffe Mill presents an exceptional opportunity for a savvy investor looking for value and a one-of-a-kind investment with endless possibilities. Since its major restoration in 2007, and further transformation in 2017, the property has operated as a mixed-use space. The Mill building features four floors of office space and a 70+ seat restaurant. The Annex/Seed House houses a brewery which hosts live music on weekend, as well as offices. Additionally, there is an undeveloped Grain Elevator, parking for 65 vehicles, and a dedicated loading dock for the restaurant. Having played a significant role in Kent County’s agricultural landscape since 1694, Radcliffe Mill underwent a historic restoration in 2007, transforming it into its current use with over 16,000 square feet of finished space. The centerpiece is the four-story mill building, dating back to 1891. The restoration seamlessly blended modern amenities like an elevator, sprinkler system and HVAC systems, with original features such as exposed beams and reclaimed flooring. While currently configured as office space across four floors, the property's zoning permits various uses, including conversion to apartments. Café Sado, a local sushi restaurant, is also housed within the mill building. All of the major restaurant equipment is included in the sale. The Annex dates back to the early 1900s and The Seed House to the 1970s. Today, the blended building features soaring ceilings, exposed woodwork, and meticulously restored standing end 2x4 flooring. Presently, the building accommodates a diverse range of wellness practitioners, with the studio space and café awaiting the creative touch of a new occupant. The sale includes all café equipment, including refrigerators, freezer, ice maker, keg tap, a warming oven and more. Four of The Seed Offices are on the ground floor, with a fifth office on the second floor, along with additional storage and laundry facilities. Finally, there is an unfinished Grain Elevator, awaiting the creativity of a new buyer. Radcliffe Mill is on the National Register of Historic Places (see documents), and having previously received historic preservation tax credits a new owner could benefit from a shorter process for further property development and improvement tax credits. The property is also in a Maryland Enterprise Zone, and an Opportunity Zone and eligible for energy improvement incentive programs. Radcliffe Mill is strategically located one-mile from downtown Chestertown, a short walk along the rail trail, which used to run directly to the grain elevator. Founded in 1706 on the banks of the Chester River, Chestertown is home to Washington College. Located approximately 80 miles from Washington, DC and Philadelphia, PA and an hour from Wilmington, DE, Chestertown hosts a number of vibrant festivals throughout the year and an active arts and entertainment district. The property consists of two different parcels, and each parcel is also being offered for sale separately. Buyers requesting additional information must sign a Non-Disclosure Agreement.

$1,236,000

860 & 870 High St, Chestertown

Listing courtesy of Taylor Properties. Contact:

Selling Office: Metropolitan Regional Information Systems, Inc..

$1,165,000

From within and without, from the front, the sides and the back, this exceptional 1876 and 1998 residence sings. Every passer-by has stopped and gazed upon the wrap around porch. No doubt, many a conversation "over the railing" has taken place for decades. Those fortunate enough to have enjoyed hospitality inside this German-wood clad home have experienced both its expansive flow of inter-connected rooms with center hall, the cozy grandness of an era long ago and comfortable living today amidst an eclectic mix of modern art and furniture, antiques, and other treasures. Prominent historic downtown location. Significant land parcel. 5 bedrooms, office, 6 public rooms on first floor, 4 and 1 half baths. Beautiful side and rear garden, with pond, brick paths, and exceptional specimens. Former garage converted to studio with full bath. Come visit Charleston or Savanah in Chestertown.

5 Beds ⋅ 5 Baths

From within and without, from the front, the sides and the back, this exceptional 1876 and 1998 residence sings. Every passer-by has stopped and gazed upon the wrap around porch. No doubt, many a conversation "over the railing" has taken place for decades. Those fortunate enough to have enjoyed hospitality inside this German-wood clad home have experienced both its expansive flow of inter-connected rooms with center hall, the cozy grandness of an era long ago and comfortable living today amidst an eclectic mix of modern art and furniture, antiques, and other treasures. Prominent historic downtown location. Significant land parcel. 5 bedrooms, office, 6 public rooms on first floor, 4 and 1 half baths. Beautiful side and rear garden, with pond, brick paths, and exceptional specimens. Former garage converted to studio with full bath. Come visit Charleston or Savanah in Chestertown.

119 High St, Chestertown

Listing courtesy of Cross Street Realtors LLC. Contact:

Selling Office: Cross Street Realtors LLC.

$1,150,000

**Exclusive Waterfront Craftsman Home with Sandy Beach – A Rare Opportunity** Nestled on the serene East Fork of Langford Creek/Bay, this stunning 3-bedroom Craftsman- style home offers the perfect blend of comfort, privacy, and natural beauty. With approximately 150 feet of shoreline and a sandy beach, this property is a true waterfront gem. **Key Features:** - **Spacious Great Room**: Added in 2001, the great room boasts expansive living space with vaulted ceilings, a loft, and a catwalk for a unique and inviting atmosphere. - **Updated Kitchen**: In 2022, the kitchen was beautifully remodeled to include modern finishes and appliances, making it the perfect space for entertaining. - **Exclusive Community**: Located within the Cacaway Farm Cooperative Housing Corporation, this home is part of a select group of 5 waterfront properties. Enjoy ownership in a corporation with the added benefit of sharing common expenses for a lower cost of living. Soon the coop ownership to become fee simple. Make your appointment today to be apart of that in the near future, with this lower price and no transfer fees. - **Private Waterfront**: A gentle slope leads you to your own piece of paradise with a sandy beach, ideal for launching kayaks or canoes. Plus, the deep-water boat slip at the community dock provides the perfect haven for boat owners. - **South-Facing Exposure**: Enjoy breathtaking water views and refreshing summer breezes from your south-facing waterfront. - **Heated Garage & Bonus Area**: The property includes a 2-car heated garage, built in 2006, with a separate storage area and a bonus space above—complete with radiant floor heat for year- round comfort. - **Modern Infrastructure**: A new BAT septic system was installed in the past 4 years, and the shared sewage disposal area is maintained by the county for worry-free living. This property offers the rare combination of privacy, community, and stunning waterfront access. Don't miss out on this incredible opportunity to own a piece of paradise. The south-facing orientation of the property offers a natural advantage when it comes to the climate and the breezes that sweep across the waterfront. Because of its position, the home is perfectly situated to catch the prevailing summer winds from the south, which are often cool and refreshing. These gentle breezes help to moderate the temperature, creating a comfortable, airy atmosphere throughout the warmer months. Whether you're relaxing on the deck, enjoying the beach, or sitting inside with the windows open, the breezes will bring a pleasant, natural ventilation, keeping things cool and comfortable even on the hottest days. The south-facing exposure also ensures you have plenty of sunshine throughout the day, adding to the overall warmth and welcoming feel of the space. This combination of sunlight and breeze provides a wonderful outdoor living experience, whether you’re lounging on the waterfront or enjoying an evening dinner on the deck with the gentle breeze in the air. It’s the kind of peaceful, tranquil environment that enhances the feeling of living in harmony with nature. **Please note**: Cacaway Farm Lane is a private road, so appointments are required to view the property. Schedule a showing today and make this dream home yours!

**Exclusive Waterfront Craftsman Home with Sandy Beach – A Rare Opportunity** Nestled on the serene East Fork of Langford Creek/Bay, this stunning 3-bedroom Craftsman- style home offers the perfect blend of comfort, privacy, and natural beauty. With approximately 150 feet of shoreline and a sandy beach, this property is a true waterfront gem. **Key Features:** - **Spacious Great Room**: Added in 2001, the great room boasts expansive living space with vaulted ceilings, a loft, and a catwalk for a unique and inviting atmosphere. - **Updated Kitchen**: In 2022, the kitchen was beautifully remodeled to include modern finishes and appliances, making it the perfect space for entertaining. - **Exclusive Community**: Located within the Cacaway Farm Cooperative Housing Corporation, this home is part of a select group of 5 waterfront properties. Enjoy ownership in a corporation with the added benefit of sharing common expenses for a lower cost of living. Soon the coop ownership to become fee simple. Make your appointment today to be apart of that in the near future, with this lower price and no transfer fees. - **Private Waterfront**: A gentle slope leads you to your own piece of paradise with a sandy beach, ideal for launching kayaks or canoes. Plus, the deep-water boat slip at the community dock provides the perfect haven for boat owners. - **South-Facing Exposure**: Enjoy breathtaking water views and refreshing summer breezes from your south-facing waterfront. - **Heated Garage & Bonus Area**: The property includes a 2-car heated garage, built in 2006, with a separate storage area and a bonus space above—complete with radiant floor heat for year- round comfort. - **Modern Infrastructure**: A new BAT septic system was installed in the past 4 years, and the shared sewage disposal area is maintained by the county for worry-free living. This property offers the rare combination of privacy, community, and stunning waterfront access. Don't miss out on this incredible opportunity to own a piece of paradise. The south-facing orientation of the property offers a natural advantage when it comes to the climate and the breezes that sweep across the waterfront. Because of its position, the home is perfectly situated to catch the prevailing summer winds from the south, which are often cool and refreshing. These gentle breezes help to moderate the temperature, creating a comfortable, airy atmosphere throughout the warmer months. Whether you're relaxing on the deck, enjoying the beach, or sitting inside with the windows open, the breezes will bring a pleasant, natural ventilation, keeping things cool and comfortable even on the hottest days. The south-facing exposure also ensures you have plenty of sunshine throughout the day, adding to the overall warmth and welcoming feel of the space. This combination of sunlight and breeze provides a wonderful outdoor living experience, whether you’re lounging on the waterfront or enjoying an evening dinner on the deck with the gentle breeze in the air. It’s the kind of peaceful, tranquil environment that enhances the feeling of living in harmony with nature. **Please note**: Cacaway Farm Lane is a private road, so appointments are required to view the property. Schedule a showing today and make this dream home yours!

23393 Cacaway Farm Ln, Chestertown

Listing courtesy of Gunther-McClary Real Estate. Contact:

Selling Office: Rock Hall Properties Real Estate.

$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.

$1,100,000

Welcome to 24028 Cliff Drive- This property offers phenomenal views, open living space, and private water access! Take in the elevated views from the great room, with cathedral ceilings and windows overlooking the Bay. The great room opens up to a spacious deck, and connecting screened-in porch for waterfront dinners. The kitchen and dining area have ample natural light and water views. The main-level boasts a large primary suite with a spacious connected bathroom and closet. The primary bedroom has access to the deck and overlooks the water. Downstairs, the walkout finished basement adds two additional bedrooms, and a den, perfect for guests or family. In the backyard, a short path leads to the private dock with two slips and a boat lift, providing instant access to the Chesapeake Bay. The two car garage and workshop offer room for storage or projects. A short drive to downtown Chestertown shops, restaurants and year-round activities. Under an hour to Middletown, and under 2 hours from Wilmington and Philadelphia.

3 Beds ⋅ 3 Baths

Welcome to 24028 Cliff Drive- This property offers phenomenal views, open living space, and private water access! Take in the elevated views from the great room, with cathedral ceilings and windows overlooking the Bay. The great room opens up to a spacious deck, and connecting screened-in porch for waterfront dinners. The kitchen and dining area have ample natural light and water views. The main-level boasts a large primary suite with a spacious connected bathroom and closet. The primary bedroom has access to the deck and overlooks the water. Downstairs, the walkout finished basement adds two additional bedrooms, and a den, perfect for guests or family. In the backyard, a short path leads to the private dock with two slips and a boat lift, providing instant access to the Chesapeake Bay. The two car garage and workshop offer room for storage or projects. A short drive to downtown Chestertown shops, restaurants and year-round activities. Under an hour to Middletown, and under 2 hours from Wilmington and Philadelphia.

24028 Cliff Drive Ext, Worton

Listing courtesy of Gunther-McClary Real Estate. Contact:

Selling Office: Select Land & Homes, LLC.

$1,100,000

120 Speer Rd, Chestertown

Listing courtesy of Mackenzie Commercial R E SVCS, LLC. Contact:

$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.

$1,070,000

This home leaves nothing to be desired. Custom built just over a decade ago, this home brings an oasis to your everyday life. You'd never guess that just a few minutes over the MD/DE state line, you'd find this gem! Tucked back on 16 acres of land, with water views of the Sassafras, you have privacy and serenity. Enter the home through the oversized custom door to a cozy entryway, met with stone accents and large, vaulted ceilings. Straight ahead you will find the grand family room, with beautiful views and a large stone custom fireplace. The floor to ceiling windows fill your day with natural light and the peaceful view of the river. Right next to the living room, you are met with a chef's kitchen, with top of the line custom hickory cabinetry and chef grade appliances, along with a breakfast bar as well- every home chef's dream! This side of the home hosts two large bedrooms, a large laundry room, a mud room complete with a pet bathing station, and interior access to the garage, as well as the unfinished framed out lofted space - ready to make your vision of an extra bedroom or home gym come to life! Follow the custom hickory floors to the other wing of the home, and find yourself in the enormous primary ensuite. The custom bathroom has a bidet, a whirlpool air jet tub and a large shower, and even a TV for when you want to relax in your personal "spa". With an additional powder room and home office space, this home checks all the boxes! The full unfinished basement is in pristine condition for storage or for additional finish-able space in the future. The tall ceilings and double egress make it the perfect canvas for your basement vision! While serene and private, this home is a short drive to I-95, Middletown DE, and more. Truly the best of both worlds and a must- see...you'll never want to leave! Schedule your tour today!

3 Beds ⋅ 3 Baths

This home leaves nothing to be desired. Custom built just over a decade ago, this home brings an oasis to your everyday life. You'd never guess that just a few minutes over the MD/DE state line, you'd find this gem! Tucked back on 16 acres of land, with water views of the Sassafras, you have privacy and serenity. Enter the home through the oversized custom door to a cozy entryway, met with stone accents and large, vaulted ceilings. Straight ahead you will find the grand family room, with beautiful views and a large stone custom fireplace. The floor to ceiling windows fill your day with natural light and the peaceful view of the river. Right next to the living room, you are met with a chef's kitchen, with top of the line custom hickory cabinetry and chef grade appliances, along with a breakfast bar as well- every home chef's dream! This side of the home hosts two large bedrooms, a large laundry room, a mud room complete with a pet bathing station, and interior access to the garage, as well as the unfinished framed out lofted space - ready to make your vision of an extra bedroom or home gym come to life! Follow the custom hickory floors to the other wing of the home, and find yourself in the enormous primary ensuite. The custom bathroom has a bidet, a whirlpool air jet tub and a large shower, and even a TV for when you want to relax in your personal "spa". With an additional powder room and home office space, this home checks all the boxes! The full unfinished basement is in pristine condition for storage or for additional finish-able space in the future. The tall ceilings and double egress make it the perfect canvas for your basement vision! While serene and private, this home is a short drive to I-95, Middletown DE, and more. Truly the best of both worlds and a must- see...you'll never want to leave! Schedule your tour today!

33487 Galena Sassafras Rd, Galena

Listing courtesy of Compass Pennsylvania, LLC. Contact:

Selling Office: Gunther-McClary Real Estate.

$1,050,000

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.

$1,050,000

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.