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Endless Possibilities on 20 Rolling Acres at Dawnwood Farm — Discover the magic of Maryland’s Eastern Shore at this captivating 20-acre farmstead, where heritage charm meets modern comfort. Whether you're a dreamer, a doer, or a little of both, this property offers something extraordinary for every kind of buyer—from adventure-seeking families and aspiring homesteaders to seasoned growers and urban escapees in search of space to breathe. At the heart of the property stands a gracious three-story 19th-century Victorian farmhouse, beautifully preserved and thoughtfully updated over the past decade. Original character—like hardwood floors, tall ceilings, and elegant millwork—blends seamlessly with modern conveniences and flexible living spaces suited to today’s lifestyle. Outdoors, you’ll find yourself surrounded by gently rolling country hills, inviting everything from morning hikes and afternoon picnics to stargazing by a campfire at night. Cool off with a dip in the in-ground pool, then retreat to the pool house for relaxation or weekend entertaining. A charming caretaker’s cottage provides extra space for guests, rental income, or multi-generational living. For those called to the land, the established organic gardens and mature fruit trees—peach, fig, and pawpaw—make it easy to envision a self-sustaining lifestyle. Cultivate your own food, raise chickens, or expand into a full-scale working farm—there’s room to grow, and inspiration at every turn. Perfectly suited for horses or livestock - the property includes two large restorable open bay barns that have been structurally stabilized, and a vintage silo. Approximately 15 acres of organically farmed open fields are currently under the purview of the Washington College CES’s Natural Lands Project and planted with native wildflowers which are in full bloom all summer long. And when you're ready for a change of pace, Betterton Beach and the sparkling Chesapeake Bay are just a few miles down the road, offering kayaking, crabbing, sunset walks, and family beach days that feel like a vacation—without ever leaving home. Whether you're seeking a weekend getaway, a family compound, or a forever home with purpose and possibility, this Still Pond treasure offers the rare blend of privacy, charm, and usable land—just minutes from Chestertown and an easy escape from city life. Don’t miss this opportunity to live your next chapter—schedule your private tour today and experience the beauty, space, and freedom of life on the Eastern Shore.

13699 Still Pond Rd, Still Pond

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

Selling Office: Gunther-McClary Real Estate.

$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.

$905,000

Serene Waterfront Retreat on Fairlee Creek is nestled in the tranquil woods of a private community just 10 minutes from the charming shops, museums, and dining of Chestertown, and the neighboring waterfront oriented town of Rock Hall. This stunning 4-bedroom, 2-bathroom waterfront home on Fairlee Creek offers the ultimate blend of seclusion, modern luxury, and effortless outdoor living. Imagine stepping out to launch your boat or kayak, or maybe just casting a line from your own private pier and floating dock—newly installed in 2025. Step inside this thoughtfully updated retreat, where every detail whispers "move-in ready." The upper level welcomes you with an open-concept living area, dining area, and kitchen, all flowing outside onto a partial wraparound deck perfect for sunset cocktails or al fresco family meals. Cozy up by the wood-burning stove in the living room on crisp evenings, or entertain in the heart of the home with a gas range and new quartz countertops in the kitchen. The upper level bedroom invites you to start your day with private deck access and creek views. Venture downstairs to the versatile lower main level, featuring three generously sized bedrooms—one with direct waterfront vistas and french doors to the expansive lower deck and lush yard. The flexible family room adapts to your lifestyle, whether as a cozy office, kids' play haven, home gym, or media lounge, all with easy access to the outdoors. Recent enhancements shine throughout: fresh paint graces the entire house and decks (2025), while a brand-new roof installed on October 6 of this year ensures peace of mind for years to come. A new central HVAC system for the lower level, efficient mini-splits on the upper level, and bathroom remodels were all completed in September of this year. The septic system was replaced in 2021 with new BAT septic system, rated for 4 bedrooms. Outside, the magic truly unfolds. Extensive hardscaping creates an entertainer's paradise, anchored by an inviting fire pit for starry-night gatherings, barbecues, gardening, or simply soaking in the creek's serene rhythm. Your private pier and floating dock make water access effortless—launch kayaks, tie up your boat, or just watch wildlife drift by. Fairlee Creek provides a short trip direct to the Chesapeake Bay. Want a little less privacy? As a resident of this exclusive community, you unlock access to the Safe Harbor at Great Oak Landing Marina for a modest annual fee. Walk, ride a golf cart, bicycle, or drive to the marina and golf course and enjoy a resort-like lifestyle with a sparkling pool, seasonal waterfront restaurant, sandy beach, and golf course. Boat slip availability? Contact Safe Harbor directly to secure your spot at the marina. Enjoy priceless privacy in a wooded waterfront wonderland, with upgrades galore and the Chesapeake Bay lifestyle at your doorstep. Schedule your private tour today and claim your water-side paradise!

4 Beds ⋅ 2 Baths

Serene Waterfront Retreat on Fairlee Creek is nestled in the tranquil woods of a private community just 10 minutes from the charming shops, museums, and dining of Chestertown, and the neighboring waterfront oriented town of Rock Hall. This stunning 4-bedroom, 2-bathroom waterfront home on Fairlee Creek offers the ultimate blend of seclusion, modern luxury, and effortless outdoor living. Imagine stepping out to launch your boat or kayak, or maybe just casting a line from your own private pier and floating dock—newly installed in 2025. Step inside this thoughtfully updated retreat, where every detail whispers "move-in ready." The upper level welcomes you with an open-concept living area, dining area, and kitchen, all flowing outside onto a partial wraparound deck perfect for sunset cocktails or al fresco family meals. Cozy up by the wood-burning stove in the living room on crisp evenings, or entertain in the heart of the home with a gas range and new quartz countertops in the kitchen. The upper level bedroom invites you to start your day with private deck access and creek views. Venture downstairs to the versatile lower main level, featuring three generously sized bedrooms—one with direct waterfront vistas and french doors to the expansive lower deck and lush yard. The flexible family room adapts to your lifestyle, whether as a cozy office, kids' play haven, home gym, or media lounge, all with easy access to the outdoors. Recent enhancements shine throughout: fresh paint graces the entire house and decks (2025), while a brand-new roof installed on October 6 of this year ensures peace of mind for years to come. A new central HVAC system for the lower level, efficient mini-splits on the upper level, and bathroom remodels were all completed in September of this year. The septic system was replaced in 2021 with new BAT septic system, rated for 4 bedrooms. Outside, the magic truly unfolds. Extensive hardscaping creates an entertainer's paradise, anchored by an inviting fire pit for starry-night gatherings, barbecues, gardening, or simply soaking in the creek's serene rhythm. Your private pier and floating dock make water access effortless—launch kayaks, tie up your boat, or just watch wildlife drift by. Fairlee Creek provides a short trip direct to the Chesapeake Bay. Want a little less privacy? As a resident of this exclusive community, you unlock access to the Safe Harbor at Great Oak Landing Marina for a modest annual fee. Walk, ride a golf cart, bicycle, or drive to the marina and golf course and enjoy a resort-like lifestyle with a sparkling pool, seasonal waterfront restaurant, sandy beach, and golf course. Boat slip availability? Contact Safe Harbor directly to secure your spot at the marina. Enjoy priceless privacy in a wooded waterfront wonderland, with upgrades galore and the Chesapeake Bay lifestyle at your doorstep. Schedule your private tour today and claim your water-side paradise!

10050 Forrest Ln, Chestertown

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

Selling Office: Coldwell Banker Chesapeake Real Estate Company.

$890,000

NO LOT LINE ADJUSTMENT!!! Nestled along the serene banks of the Sassafras River, this charming brick fixer-upper offers a rare opportunity to create your dream waterfront retreat. Set on a sprawling 2.58-acre lot with 175 feet of private shoreline, the property boasts breathtaking river views, peaceful natural surroundings, and direct deep-water access. Inside, the home offers over 1,500 square feet of functional living space ready for your personal touch. It features 2 bedrooms, 2 full baths, a cozy family room with a fireplace, and a spacious river room adorned with stunning bluestone flooring. An expansive enclosed porch invites you to sip your morning coffee while taking in the sunrise over the water. A conveniently attached garage adds to the home’s functionality. The real star of this property is outside: a private 185-foot dock with 4+ MLW, complete with a boathouse, boat lift, and launch ramp — perfect for boating, kayaking, paddleboarding, or simply enjoying life by the water. Whether you’re an avid water enthusiast or seeking a tranquil escape, this location delivers. Offered strictly AS IS, this property presents multiple possibilities — renovate, expand, or start anew. Whatever your vision, the actual value lies in the land and unparalleled location on one of the most desirable stretches of the Sassafras River. Please do not walk on the dock, as it needs to be renovated along with the boathouse. There is a shared driveway easement; however, please confirm with the county that you have the option to put in your own driveway.

2 Beds ⋅ 2 Baths

NO LOT LINE ADJUSTMENT!!! Nestled along the serene banks of the Sassafras River, this charming brick fixer-upper offers a rare opportunity to create your dream waterfront retreat. Set on a sprawling 2.58-acre lot with 175 feet of private shoreline, the property boasts breathtaking river views, peaceful natural surroundings, and direct deep-water access. Inside, the home offers over 1,500 square feet of functional living space ready for your personal touch. It features 2 bedrooms, 2 full baths, a cozy family room with a fireplace, and a spacious river room adorned with stunning bluestone flooring. An expansive enclosed porch invites you to sip your morning coffee while taking in the sunrise over the water. A conveniently attached garage adds to the home’s functionality. The real star of this property is outside: a private 185-foot dock with 4+ MLW, complete with a boathouse, boat lift, and launch ramp — perfect for boating, kayaking, paddleboarding, or simply enjoying life by the water. Whether you’re an avid water enthusiast or seeking a tranquil escape, this location delivers. Offered strictly AS IS, this property presents multiple possibilities — renovate, expand, or start anew. Whatever your vision, the actual value lies in the land and unparalleled location on one of the most desirable stretches of the Sassafras River. Please do not walk on the dock, as it needs to be renovated along with the boathouse. There is a shared driveway easement; however, please confirm with the county that you have the option to put in your own driveway.

29341 Glencoe Rd, Kennedyville

Listing courtesy of Coldwell Banker Realty. Contact:

This property has an amazing amount to offer! There are 3 parcels included with a total of just over 5.5 acres. The complex includes a commercially zoned 2.6+/- parcel with several large outbuildings, a 4 bedroom, 2.5 bath extremely well built home on 2.68+/- acres a .35 acre lot. The commercial parcel has a 4 bay garage with foam insulation, an approximately 100' long x approximately 30' wide insulated workshop with 14' door that includes a full bath and laundry, a half bath, office and is heated and cooled. There is a 40' x 30' pole building in the rear of the commercial side. The house also offers a spacious kitchen with center island and granite counters, a family area, laminate flooring throughout most of the house, a laundry room, screened porch and a partial basement. Heated and cooled with heat pump and propane backup. Hot water is supplied by tankless water heating system. There is a 1 car attached garage and a large open dirt floor shed for additional space close by. In the rear of the property is a 47' x 42' two bay pole building with 1 bay having a 12'+/- door.Last but not least is a .35+/- acre lot that has potential to be built on but would require a water and sewer allocation. This is a rare find and would be perfect for someone who has a small lawn/landscaping business and wants to expand or possibly a small excavating business and wants to live where they work. The possibilities are are there for the entrepreneur who has vision, to utilize everything this property has to offer!!

$875,000

10700 Worton Rd, Worton

Listing courtesy of Doug Ashley Realtors, LLC. Contact:

Selling Office: Select Land & Homes, LLC.

$875,000

This property has an amazing amount to offer! There are 3 parcels included with a total of just over 5.5 acres. The complex includes a 4 bedroom, 2.5 baths extremely well built home on 2.68+/- acres, a .35 acre lot and a commercially zoned 2.6+/- parcel with several large outbuildings. The house also offers a spacious kitchen with center island and granite counters, a family area, laminate flooring throughout most of the house, a laundry room, screened porch and a partial basement. Heated and cooled with heat pump and propane backup. Hot water is supplied by tankless water heating system. There is a 1 car attached garage and a large open dirt floor shed for additional space close by. In the rear of the property is a 47' x 42' two bay pole building with 1 bay having a 12'+/- door. The commercial parcel has a 4 bay garage with foam insulation, an approximately 100' long x approximately 30' wide insulated workshop with 14' door that includes a full bath and laundry, a half bath, office and is heated and cooled. There is a 40' x 30' pole building in the rear of the commercial side. Last but not least is a .35+/- acre lot that has potential to be built on but would require a water and sewer allocation. This is a rare find and would be perfect for someone who has a small lawn/landscaping business and wants to expand or possibly a small excavating business and wants to live where they work. The possibilities are are there for the entrepreneur who has vision, to utilize everything this property has to offer!!

This property has an amazing amount to offer! There are 3 parcels included with a total of just over 5.5 acres. The complex includes a 4 bedroom, 2.5 baths extremely well built home on 2.68+/- acres, a .35 acre lot and a commercially zoned 2.6+/- parcel with several large outbuildings. The house also offers a spacious kitchen with center island and granite counters, a family area, laminate flooring throughout most of the house, a laundry room, screened porch and a partial basement. Heated and cooled with heat pump and propane backup. Hot water is supplied by tankless water heating system. There is a 1 car attached garage and a large open dirt floor shed for additional space close by. In the rear of the property is a 47' x 42' two bay pole building with 1 bay having a 12'+/- door. The commercial parcel has a 4 bay garage with foam insulation, an approximately 100' long x approximately 30' wide insulated workshop with 14' door that includes a full bath and laundry, a half bath, office and is heated and cooled. There is a 40' x 30' pole building in the rear of the commercial side. Last but not least is a .35+/- acre lot that has potential to be built on but would require a water and sewer allocation. This is a rare find and would be perfect for someone who has a small lawn/landscaping business and wants to expand or possibly a small excavating business and wants to live where they work. The possibilities are are there for the entrepreneur who has vision, to utilize everything this property has to offer!!

10672 Worton Rd, Worton

Listing courtesy of Doug Ashley Realtors, LLC. Contact:

Selling Office: Select Land & Homes, LLC.

$875,000

Nestled on the tranquil shores of Swan Creek, this 3,000+/- sq ft waterfront home offers a rare blend of elegance, comfort and Chesapeake charm. Featuring 3-4 bedrooms, 3.5 baths, and a desirable first-floor primary suite, this thoughtfully designed home invites relaxed coastal living. The great room is a showstopper with its dramatic two-story windows and cozy fireplace, framing picture-perfect waterviews of boats gliding by. Enjoy seamless indoor-outdoor living with a fully fenced yard—ideal for entertaining, gardening, or quiet evenings under the stars. The spacious two-car garage offers ample storage, while your private boat slip just steps away provides effortless access to the water. Located in a unique land condominium community in the heart of Rock Hall, this home is just minutes from marinas, restaurants, and shops. Whether you're savoring fresh local crabs on the deck or soaking in Swan Creek’s unforgettable sunsets, every day here feels like a getaway. This is Eastern Shore living at its finest.

Nestled on the tranquil shores of Swan Creek, this 3,000+/- sq ft waterfront home offers a rare blend of elegance, comfort and Chesapeake charm. Featuring 3-4 bedrooms, 3.5 baths, and a desirable first-floor primary suite, this thoughtfully designed home invites relaxed coastal living. The great room is a showstopper with its dramatic two-story windows and cozy fireplace, framing picture-perfect waterviews of boats gliding by. Enjoy seamless indoor-outdoor living with a fully fenced yard—ideal for entertaining, gardening, or quiet evenings under the stars. The spacious two-car garage offers ample storage, while your private boat slip just steps away provides effortless access to the water. Located in a unique land condominium community in the heart of Rock Hall, this home is just minutes from marinas, restaurants, and shops. Whether you're savoring fresh local crabs on the deck or soaking in Swan Creek’s unforgettable sunsets, every day here feels like a getaway. This is Eastern Shore living at its finest.

6119 New St Unit 2, Rock Hall

Listing courtesy of Rock Hall Properties Real Estate. Contact:

Selling Office: Unrepresented.

$872,500

Elevated coastal elegance is displayed in this waterfront perched on the banks of Mill Creek. An open floor plan, radiant floor heating, high ceilings in the great room create an ambience conducive to a luxury weekend retreat or full time residence. Water views are celebrated from nearly every inch of the home and the large windows allow for a deep connection with nature. Outdoor living is a highlight with a covered waterfront screened in porch for crab feasts, fire pit with seating providing sweeping views of Mill Creek, and expensive rear decks on each floor. Two bedrooms on the main level make one floor living a breeze including the primary with ensuite bathroom and walk in closet. Stainless steel appliances adorn the kitchen. The great room is impressive, creating a magnet effect for family and friends. Upstairs has an bonus room perfect for your home office. This is a boater's paradise with direct access to the bay within minutes but protected waters at your shoreline. The private dock includes an additional floating pier suitable for kayak excursions. The front yard has thoughtful planting, pea gravel driveway, and potting shed. Across the lane is an additional lot that comes with the property and is currently used for storage. Feel a connection with the Eastern Shore and its waterways with this high end waterfront sanctuary just 15 minutes from the shops, galleries, and restaurants of historic Chestertown.

3 Beds ⋅ 3 Baths

Elevated coastal elegance is displayed in this waterfront perched on the banks of Mill Creek. An open floor plan, radiant floor heating, high ceilings in the great room create an ambience conducive to a luxury weekend retreat or full time residence. Water views are celebrated from nearly every inch of the home and the large windows allow for a deep connection with nature. Outdoor living is a highlight with a covered waterfront screened in porch for crab feasts, fire pit with seating providing sweeping views of Mill Creek, and expensive rear decks on each floor. Two bedrooms on the main level make one floor living a breeze including the primary with ensuite bathroom and walk in closet. Stainless steel appliances adorn the kitchen. The great room is impressive, creating a magnet effect for family and friends. Upstairs has an bonus room perfect for your home office. This is a boater's paradise with direct access to the bay within minutes but protected waters at your shoreline. The private dock includes an additional floating pier suitable for kayak excursions. The front yard has thoughtful planting, pea gravel driveway, and potting shed. Across the lane is an additional lot that comes with the property and is currently used for storage. Feel a connection with the Eastern Shore and its waterways with this high end waterfront sanctuary just 15 minutes from the shops, galleries, and restaurants of historic Chestertown.

10761 Kasota Rd, Chestertown

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

Selling Office: Compass.

$850,000

Motivated sellers!! Nestled on .83 acres, this captivating Chesapeake Bay waterfront home offers the perfect blend of comfort and coastal charm just outside of Rock Hall. The property includes a 3-bedroom plus bonus room, 2 1/2-bath main house and a detached garage with a 1-bedroom, 1-bath efficiency apartment, ideal for guests or potential rental use. Step inside to be welcomed by a stunning wall of windows showcasing panoramic views of the Chesapeake Bay. The spacious family room features vaulted ceilings and a cozy wood-burning fireplace, creating an inviting space for relaxation. The modern, coastal kitchen is a chef’s delight, boasting a large island, a breakfast area, and new appliances. The bayside primary bedroom is a serene retreat, complete with sliding door access to a deck, an en-suite bathroom, and an oversized closet. Two additional guest bedrooms on the main level share a full bathroom, providing ample space for family or visitors. Upstairs, a versatile bedroom with a half bath offers flexibility for various needs. The expansive laundry room comes equipped with an additional refrigerator, wine refrigerator, sink, and plenty of storage space. The bonus room above the detached garage provides privacy for guests, featuring a full bathroom and a balcony overlooking the picturesque bay. Outdoor living is at its finest with two waterside decks, a picnic area, and a fire pit perfect for gatherings. The new pier with a 10,000 lb boat lift makes boating and water activities a breeze. Watch breathtaking sunsets over the Chesapeake Bay and create lasting memories in this home designed for entertaining family and friends. Don’t miss the opportunity to own this extraordinary waterfront retreat—schedule your private viewing today!

Motivated sellers!! Nestled on .83 acres, this captivating Chesapeake Bay waterfront home offers the perfect blend of comfort and coastal charm just outside of Rock Hall. The property includes a 3-bedroom plus bonus room, 2 1/2-bath main house and a detached garage with a 1-bedroom, 1-bath efficiency apartment, ideal for guests or potential rental use. Step inside to be welcomed by a stunning wall of windows showcasing panoramic views of the Chesapeake Bay. The spacious family room features vaulted ceilings and a cozy wood-burning fireplace, creating an inviting space for relaxation. The modern, coastal kitchen is a chef’s delight, boasting a large island, a breakfast area, and new appliances. The bayside primary bedroom is a serene retreat, complete with sliding door access to a deck, an en-suite bathroom, and an oversized closet. Two additional guest bedrooms on the main level share a full bathroom, providing ample space for family or visitors. Upstairs, a versatile bedroom with a half bath offers flexibility for various needs. The expansive laundry room comes equipped with an additional refrigerator, wine refrigerator, sink, and plenty of storage space. The bonus room above the detached garage provides privacy for guests, featuring a full bathroom and a balcony overlooking the picturesque bay. Outdoor living is at its finest with two waterside decks, a picnic area, and a fire pit perfect for gatherings. The new pier with a 10,000 lb boat lift makes boating and water activities a breeze. Watch breathtaking sunsets over the Chesapeake Bay and create lasting memories in this home designed for entertaining family and friends. Don’t miss the opportunity to own this extraordinary waterfront retreat—schedule your private viewing today!

4938 Huntingfield Rd, Rock Hall

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

Selling Office: Benson & Mangold, 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.

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.

$800,000

Nestled within the serene enclave of Cliffs City, this waterfront homestead offers a harmonious blend of natural beauty and water access. Spanning over 3.35 acres, the property boasts an impressive 185 feet of riverfront, providing an idyllic setting for your lifestyle. Charming brick ranch home features three bedrooms and two full baths. The heart of the home is the open family and dining room, where a cozy gas fireplace serves as a focal point set between custom built bookshelves and cabinets. Large windows throughout the home frame stunning views of the bay and river, allowing natural light to flood the space and create an inviting atmosphere. Outside, the property features a private dock site, ideal for boating enthusiasts and those who enjoy kayaking or canoeing on the tranquil waters. The rip-rap waterfront enhances the natural beauty while providing stability and protection. For those with a passion for outdoor living, the expansive lot offers ample space for gardening, entertaining, or simply enjoying the scenic vistas that surround you. Additional structures, including a 1,000 SF pole barn and two shed bays, provide practical storage solutions while maintaining the aesthetic charm of the property. Embrace the luxury of waterfront living, surrounded by nature's splendor, and create lasting memories in this exceptional property. Located only 10 miles from Historic Chestertown, you have access to shops, restaurants and the many arts and craft fairs, farmers markets and annual Tea Party celebration. This residence needs updating and the value is in the land and property. is not just a home; it's a lifestyle, where every day feels like a vacation. Home and pier are being sold strictly As-Is. Seller will not be making any repairs

3 Beds ⋅ 2 Baths

Nestled within the serene enclave of Cliffs City, this waterfront homestead offers a harmonious blend of natural beauty and water access. Spanning over 3.35 acres, the property boasts an impressive 185 feet of riverfront, providing an idyllic setting for your lifestyle. Charming brick ranch home features three bedrooms and two full baths. The heart of the home is the open family and dining room, where a cozy gas fireplace serves as a focal point set between custom built bookshelves and cabinets. Large windows throughout the home frame stunning views of the bay and river, allowing natural light to flood the space and create an inviting atmosphere. Outside, the property features a private dock site, ideal for boating enthusiasts and those who enjoy kayaking or canoeing on the tranquil waters. The rip-rap waterfront enhances the natural beauty while providing stability and protection. For those with a passion for outdoor living, the expansive lot offers ample space for gardening, entertaining, or simply enjoying the scenic vistas that surround you. Additional structures, including a 1,000 SF pole barn and two shed bays, provide practical storage solutions while maintaining the aesthetic charm of the property. Embrace the luxury of waterfront living, surrounded by nature's splendor, and create lasting memories in this exceptional property. Located only 10 miles from Historic Chestertown, you have access to shops, restaurants and the many arts and craft fairs, farmers markets and annual Tea Party celebration. This residence needs updating and the value is in the land and property. is not just a home; it's a lifestyle, where every day feels like a vacation. Home and pier are being sold strictly As-Is. Seller will not be making any repairs

4671 Cliffs City Rd, Chestertown

Listing courtesy of Cummings & Co. Realtors. Contact:

Extraordinary development opportunity in downtown historic Chestertown. Large parcel of land (1.56+/- acres) zoned C-2 (half R1 and half R5 zoning) many permitted uses such as Muliple-Family dwelling, Townhouses, professional and business offices, non-profit museums, and others. Includes 1 building (Warehouse) and property fronts on three streets. Excellent location-- just a few blocks to the Chester River water frontage, Parks, shops, restaurants, galleries and Washington College.

$800,000

206 Cannon St, Chestertown

Listing courtesy of Benson & Mangold, LLC. Contact:

Discover the charm of this exquisite transitional Victorian home nestled just off the beaten path in downtown Chestertown. Built in 2011, this stunning residence boasts meticulously maintained living space, featuring an open floor plan that seamlessly blends comfort and style. The interior showcases beautiful wood floors, exposed beams, and an abundance of natural light from skylights and double-pane windows, creating an inviting atmosphere throughout. The owner's suite is located on the main floor with a beautiful new ensuite bathroom. On the second floor, you will find another living area with an additional 3 bedrooms and bathroom. Cozy up in the living area by the Vermont Castings pellet stove, perfect for creating lasting memories. The main floor laundry adds convenience to your daily routine. Step outside to enjoy the wrap-around porch, screened porch, and balcony, all overlooking the beautifully landscaped yard, ideal for entertaining or simply unwinding in your private oasis. The attached garage and paved driveway provide ample parking for you and your guests. Encapsulated crawlspace with room for storage. This home is just a short walk from historic downtown with all of the amenities like shopping, dining, farmers market and theater.

$795,000

Discover the charm of this exquisite transitional Victorian home nestled just off the beaten path in downtown Chestertown. Built in 2011, this stunning residence boasts meticulously maintained living space, featuring an open floor plan that seamlessly blends comfort and style. The interior showcases beautiful wood floors, exposed beams, and an abundance of natural light from skylights and double-pane windows, creating an inviting atmosphere throughout. The owner's suite is located on the main floor with a beautiful new ensuite bathroom. On the second floor, you will find another living area with an additional 3 bedrooms and bathroom. Cozy up in the living area by the Vermont Castings pellet stove, perfect for creating lasting memories. The main floor laundry adds convenience to your daily routine. Step outside to enjoy the wrap-around porch, screened porch, and balcony, all overlooking the beautifully landscaped yard, ideal for entertaining or simply unwinding in your private oasis. The attached garage and paved driveway provide ample parking for you and your guests. Encapsulated crawlspace with room for storage. This home is just a short walk from historic downtown with all of the amenities like shopping, dining, farmers market and theater.

201 Radcliffe Dr, Chestertown

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

Selling Office: Coldwell Banker Chesapeake Real Estate Company.

$775,000

Handsome farmhouse on 36 acres. House maintains much of its original character. Spacious rooms and beautiful views.

Handsome farmhouse on 36 acres. House maintains much of its original character. Spacious rooms and beautiful views.

8293 Brices Mill Rd, Chestertown

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

Originally built with handcrafted bricks in 1782, this Flemish Bond Georgian Colonial home is the embodiment of simple elegance. Restored with the utmost historical respect in the mid-1980’s with handcrafted oak windows and mahogany doors with period hardware and modernized with preservation-sensitive practices and materials over the past eight years by the current stewards of the home, step into the past while enjoying today’s comforts. The four-bay home has a traditional floor plan with the living and dining room flanking the center hall, a large sunken family room anchored by the massive hearth – reconstructed with original bricks from the 1782 structure and walnut mantel, and a kitchen and sunroom addition on the back of the home, added between the mid-80’s and early-90’s. The kitchen was afforded another renovation around 2008 with high end finishes and an open, welcoming concept ideal for functionality and entertaining. Follow the original staircase upstairs, running your hand along the centuries old banister to two of the bedrooms which share a generous bathroom off the second story landing. Closets have been incorporated in the landing and bedrooms to allow for modern storage solutions, all while using period specific paneling and hardware to replicate the historic aspects of the original design scheme of the 1790s. The primary suite wing, accessed by its own staircase, consists of a one-bay bedroom, dressing room with laundry, and an en suite bath overlooking the rear yard. Each bedroom has its own fireplace, where the gentle crackle of the flames offers a retreat from the modern world, inviting guests to appreciate simpler times and the charm of a bygone era. Modern comfort conveniences including two year new HVAC units, preservation-sensitive insulation, professionally restored windows with new storm windows, and two brand new woodstoves round out the incredible features that make this home low maintenance and turn-key. The studio barn, accessed by its own gravel drive and parking pad, is a two story, two bay garage, with an interior but separate workshop. Since 2018 it has been insulated, drywalled, painted, had its own dedicated water, high-voltage electric, and fiber optic internet lines run, and had a pellet stove installed. Situated on 6.8 serene acres, the grounds have a mature boxwood hedge, a perimeter of pines, fallow pastures which fill with wildflowers throughout the summer, wandering paths to birdwatch, and scattered perennials which pop up each spring with a burst of color and personality. The home has a rich history dating back to the earliest settlements of Maryland. The namesake of the road upon which it sits, the home was built by the Lamb family who settled in the area in the 1600s, purchasing land from the area Native Americans. The Lambs went on to divide the farmland, constructing many homes built in the same period for their descendants including this one, the best-restored home of the Lamb houses. The Hepburns (actress Catherine Hepburn’s family) and the Bowers are part of the same local family. The local Library has a detailed reference book on the history of the Family. Friendship was constructed by Daniel Lamb in 1782 – the same year Washington College in Chestertown was founded. The original house was a four-room, split-level house. You can see “DL 1782” in the date brick that was salvaged when the chimney was reconstructed in 1985. Ten years later, his nephew went-on to construct the east wing of the house to complete the center-hall colonial you see today. The 1792 date brick for this addition for this addition can be located between the two windows on the east-wall exterior: “H DL 1792” for Harriet Bowers and Daniel Lamb. You can find Harriet’s signature on the ceiling beam of the center bedroom.

$765,000

3 Beds ⋅ 3 Baths

Originally built with handcrafted bricks in 1782, this Flemish Bond Georgian Colonial home is the embodiment of simple elegance. Restored with the utmost historical respect in the mid-1980’s with handcrafted oak windows and mahogany doors with period hardware and modernized with preservation-sensitive practices and materials over the past eight years by the current stewards of the home, step into the past while enjoying today’s comforts. The four-bay home has a traditional floor plan with the living and dining room flanking the center hall, a large sunken family room anchored by the massive hearth – reconstructed with original bricks from the 1782 structure and walnut mantel, and a kitchen and sunroom addition on the back of the home, added between the mid-80’s and early-90’s. The kitchen was afforded another renovation around 2008 with high end finishes and an open, welcoming concept ideal for functionality and entertaining. Follow the original staircase upstairs, running your hand along the centuries old banister to two of the bedrooms which share a generous bathroom off the second story landing. Closets have been incorporated in the landing and bedrooms to allow for modern storage solutions, all while using period specific paneling and hardware to replicate the historic aspects of the original design scheme of the 1790s. The primary suite wing, accessed by its own staircase, consists of a one-bay bedroom, dressing room with laundry, and an en suite bath overlooking the rear yard. Each bedroom has its own fireplace, where the gentle crackle of the flames offers a retreat from the modern world, inviting guests to appreciate simpler times and the charm of a bygone era. Modern comfort conveniences including two year new HVAC units, preservation-sensitive insulation, professionally restored windows with new storm windows, and two brand new woodstoves round out the incredible features that make this home low maintenance and turn-key. The studio barn, accessed by its own gravel drive and parking pad, is a two story, two bay garage, with an interior but separate workshop. Since 2018 it has been insulated, drywalled, painted, had its own dedicated water, high-voltage electric, and fiber optic internet lines run, and had a pellet stove installed. Situated on 6.8 serene acres, the grounds have a mature boxwood hedge, a perimeter of pines, fallow pastures which fill with wildflowers throughout the summer, wandering paths to birdwatch, and scattered perennials which pop up each spring with a burst of color and personality. The home has a rich history dating back to the earliest settlements of Maryland. The namesake of the road upon which it sits, the home was built by the Lamb family who settled in the area in the 1600s, purchasing land from the area Native Americans. The Lambs went on to divide the farmland, constructing many homes built in the same period for their descendants including this one, the best-restored home of the Lamb houses. The Hepburns (actress Catherine Hepburn’s family) and the Bowers are part of the same local family. The local Library has a detailed reference book on the history of the Family. Friendship was constructed by Daniel Lamb in 1782 – the same year Washington College in Chestertown was founded. The original house was a four-room, split-level house. You can see “DL 1782” in the date brick that was salvaged when the chimney was reconstructed in 1985. Ten years later, his nephew went-on to construct the east wing of the house to complete the center-hall colonial you see today. The 1792 date brick for this addition for this addition can be located between the two windows on the east-wall exterior: “H DL 1792” for Harriet Bowers and Daniel Lamb. You can find Harriet’s signature on the ceiling beam of the center bedroom.

25999 Lambs Meadow Rd, Worton

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

Selling Office: Monument Sotheby's International Realty.

$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.

$750,000

Nestled along the tranquil western shore of the Chester River, this beautiful townhome in Chester River Landing offers an unparalleled waterfront living experience with direct water access and captivating water views. Just a short stroll from the historic heart of Chestertown, MD, it combines modern luxury with timeless charm. This elegant 3-bedroom, 2.5-bath residence is designed to maximize comfort and style. The spacious living areas are bathed in natural light, enhancing the serene ambiance of this waterfront haven. The open-plan living and dining areas flow seamlessly into the well-appointed kitchen, equipped with top-of-the-line appliances and ample storage. The master bedroom is a true retreat, with easterly river views and an ensuite bath. The additional bedrooms are generously sized, perfect for family or guests. The 3.5 baths are elegantly designed, featuring modern fixtures and finishes. One of the standout features of this home is its perfect vantage point for watching the daily sunrise. Imagine starting your day with a cup of coffee on the balcony, as the first light of dawn reflects off the calm waters of the Chester River while rowing teams begin their daily workout. Whether you're seeking a peaceful waterfront retreat or a picturesque spot to entertain, this townhome offers it all. The community amenities of Chester River Landing further enhance the lifestyle, with walking paths, swimming pool, private pier with available boat slips for purchase or lease, outdoor grilling and beautifully landscaped common areas. Discover the unique blend of history, luxury, and natural beauty at this waterfront home on the Chester River.

Nestled along the tranquil western shore of the Chester River, this beautiful townhome in Chester River Landing offers an unparalleled waterfront living experience with direct water access and captivating water views. Just a short stroll from the historic heart of Chestertown, MD, it combines modern luxury with timeless charm. This elegant 3-bedroom, 2.5-bath residence is designed to maximize comfort and style. The spacious living areas are bathed in natural light, enhancing the serene ambiance of this waterfront haven. The open-plan living and dining areas flow seamlessly into the well-appointed kitchen, equipped with top-of-the-line appliances and ample storage. The master bedroom is a true retreat, with easterly river views and an ensuite bath. The additional bedrooms are generously sized, perfect for family or guests. The 3.5 baths are elegantly designed, featuring modern fixtures and finishes. One of the standout features of this home is its perfect vantage point for watching the daily sunrise. Imagine starting your day with a cup of coffee on the balcony, as the first light of dawn reflects off the calm waters of the Chester River while rowing teams begin their daily workout. Whether you're seeking a peaceful waterfront retreat or a picturesque spot to entertain, this townhome offers it all. The community amenities of Chester River Landing further enhance the lifestyle, with walking paths, swimming pool, private pier with available boat slips for purchase or lease, outdoor grilling and beautifully landscaped common areas. Discover the unique blend of history, luxury, and natural beauty at this waterfront home on the Chester River.

212 Landing Ln, Chestertown

Listing courtesy of Gunther-McClary Real Estate. Contact:

$749,500

3 Beds ⋅ 3 Baths

6 Byford Ct, Chestertown

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

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.

$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.

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.

$740,000

Tremendously charming historic house, sensitively restored, a short distance from Great Oak Marina. Beautiful original 18th century pine floors, mantel pieces, six-panel doors and built-in cupboard. House was originally two small historic houses located in the village of Church Creek, Dorchester County, Maryland, moved to current location ca.1980. Private yard and garden. Chestertown and Rock Hall nearby. House has upgraded electric and Best Available Technology (BAT) septic system. Well water filtration system. First story bedroom and guest bedroom, additional bedrooms up. Modern kitchen with new Whirlpool brand stainless steel appliances, gas cookstove opening to family/entertaining area. Formal parlor with gas fireplace. Sunroom with skylights, tile floor, ceiling fan, overlooking garden. Most rooms have plantation shutters. Spacious closets. New recessed lights. If owner wants to join marina with pool and beach, it is believed that current fee is $100; additional dock fee if new owner has a boat and desires slip. $350/year road maintenance.

Tremendously charming historic house, sensitively restored, a short distance from Great Oak Marina. Beautiful original 18th century pine floors, mantel pieces, six-panel doors and built-in cupboard. House was originally two small historic houses located in the village of Church Creek, Dorchester County, Maryland, moved to current location ca.1980. Private yard and garden. Chestertown and Rock Hall nearby. House has upgraded electric and Best Available Technology (BAT) septic system. Well water filtration system. First story bedroom and guest bedroom, additional bedrooms up. Modern kitchen with new Whirlpool brand stainless steel appliances, gas cookstove opening to family/entertaining area. Formal parlor with gas fireplace. Sunroom with skylights, tile floor, ceiling fan, overlooking garden. Most rooms have plantation shutters. Spacious closets. New recessed lights. If owner wants to join marina with pool and beach, it is believed that current fee is $100; additional dock fee if new owner has a boat and desires slip. $350/year road maintenance.

10230 John Carvill Rd, Chestertown

Listing courtesy of Shoreline Realty. Contact:

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.

$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.

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:

This incredibly private retreat property is situated on 9+ acres in Northern Kent County Maryland overlooking it's own private lake loaded with record size fish and includes a nearly new 2800+/- sq. foot home built in 2020, two detached 3-bay metal shop buildings, and a vast variety of native wildlife including bald eagles, herons, turkeys, deer, and multiple waterfowl species. The home itself offers spacious rooms, country eat-in kitchen, glassed in porch overlooking the private inground pool, first floor primary suite with upgrade bathroom features, walk in closet, and sliding doors to your own lakeside deck, second first floor bedroom with second full bath across the hall, laundry/utility room, hobby room, and single car attached garage. Upstairs there is a third bedroom, large recreation room, and roughed in third bath. The property is located at the end of Sixth Avenue in the town of Betterton, known as the Jewel of the Chesapeake and is only a short ride to all the conveniences of Middletown Delaware, Historic Chestertown, Rock Hall, and Molly's Sporting Goods. This exceptional offering is ideal for either full time residency or weekend vacation occupancy!

$725,000

4 Beds ⋅ 2 Baths

This incredibly private retreat property is situated on 9+ acres in Northern Kent County Maryland overlooking it's own private lake loaded with record size fish and includes a nearly new 2800+/- sq. foot home built in 2020, two detached 3-bay metal shop buildings, and a vast variety of native wildlife including bald eagles, herons, turkeys, deer, and multiple waterfowl species. The home itself offers spacious rooms, country eat-in kitchen, glassed in porch overlooking the private inground pool, first floor primary suite with upgrade bathroom features, walk in closet, and sliding doors to your own lakeside deck, second first floor bedroom with second full bath across the hall, laundry/utility room, hobby room, and single car attached garage. Upstairs there is a third bedroom, large recreation room, and roughed in third bath. The property is located at the end of Sixth Avenue in the town of Betterton, known as the Jewel of the Chesapeake and is only a short ride to all the conveniences of Middletown Delaware, Historic Chestertown, Rock Hall, and Molly's Sporting Goods. This exceptional offering is ideal for either full time residency or weekend vacation occupancy!

21 6th Ave, Betterton

Listing courtesy of Select Land & Homes, LLC. Contact:

Selling Office: Benson & Mangold, 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.

$700,000

Nestled in the serene Orchard Hill community, this stunning Craftsman-Colonial offers 3,735 sq. ft. of luxury and comfort. The open, light-filled floor plan showcases rich hardwood floors and elegant finishes throughout. The gourmet kitchen features upgraded countertops, pecan wood-stained cherry cabinetry, stainless steel appliances, including double ovens, a gas cooktop, and a tankless water heater. It opens to the family room with a cozy corner gas fireplace—perfect for entertaining or relaxing. The main level includes an office, primary suite with a large bath and walk-in closet, an additional bedroom and full bath, and a dedicated laundry area. A screened-in porch off the main floor provides a peaceful space to enjoy morning coffee or evening gatherings surrounded by nature. Upstairs offers an open sitting area with window seat, two additional bedrooms, and a full bath. Set on a beautifully landscaped 2.81-acre lot backing to trees, this property provides a private outdoor retreat. Additional highlights include a side-entry garage, paved driveway, and outbuilding for extra storage. Experience the best of Orchard Hill living—where quality, comfort, and natural beauty come together.

Nestled in the serene Orchard Hill community, this stunning Craftsman-Colonial offers 3,735 sq. ft. of luxury and comfort. The open, light-filled floor plan showcases rich hardwood floors and elegant finishes throughout. The gourmet kitchen features upgraded countertops, pecan wood-stained cherry cabinetry, stainless steel appliances, including double ovens, a gas cooktop, and a tankless water heater. It opens to the family room with a cozy corner gas fireplace—perfect for entertaining or relaxing. The main level includes an office, primary suite with a large bath and walk-in closet, an additional bedroom and full bath, and a dedicated laundry area. A screened-in porch off the main floor provides a peaceful space to enjoy morning coffee or evening gatherings surrounded by nature. Upstairs offers an open sitting area with window seat, two additional bedrooms, and a full bath. Set on a beautifully landscaped 2.81-acre lot backing to trees, this property provides a private outdoor retreat. Additional highlights include a side-entry garage, paved driveway, and outbuilding for extra storage. Experience the best of Orchard Hill living—where quality, comfort, and natural beauty come together.

8951 Orchard Dr, Chestertown

Listing courtesy of Rock Hall Properties Real Estate. Contact:

Selling Office: Coldwell Banker Chesapeake Real Estate Company.

$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.

3 Beds ⋅ 2 Baths

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.

$695,000

Beautiful and spacious 3- bedroom home in historic Chestertown. Just a short distance from vibrant shops, restaurants, and the scenic Chester River waterfront. The gourmet kitchen has a beautiful wood-top island and stainless steel appliances. The kitchen leads to the large formal dining room, featuring the original stone fireplace, updated with a gas insert. The living space is designed for both comfortable living and effortless entertaining. During the winter, enjoy the wood burning fireplace in the living room, or warm up in the beautiful sunroom, just off of the living space. Downstairs there’s a full bathroom and bedroom, as well as a half bath. Upstairs you’ll find two full bathrooms and two bedrooms. additionally, there's a studio or office nook, which could be used as extra sleeping space. This property also features a unique opportunity for extra income. Part of the second-floor can become it's own apartment, complete with a kitchen, full bathroom, and a private entrance from the driveway. The one bedroom apartment is perfect for guests, an in-law suite, or as a rental unit. Outside, a fenced-in yard with a covered patio offers a private oasis for relaxing evenings. The private driveway leads to a spacious barn garage with three barn doors. The barn offers ample storage, space for a small vehicle, or could be used as a workshop. This home truly has it all, in the heart of Chestertown!

Beautiful and spacious 3- bedroom home in historic Chestertown. Just a short distance from vibrant shops, restaurants, and the scenic Chester River waterfront. The gourmet kitchen has a beautiful wood-top island and stainless steel appliances. The kitchen leads to the large formal dining room, featuring the original stone fireplace, updated with a gas insert. The living space is designed for both comfortable living and effortless entertaining. During the winter, enjoy the wood burning fireplace in the living room, or warm up in the beautiful sunroom, just off of the living space. Downstairs there’s a full bathroom and bedroom, as well as a half bath. Upstairs you’ll find two full bathrooms and two bedrooms. additionally, there's a studio or office nook, which could be used as extra sleeping space. This property also features a unique opportunity for extra income. Part of the second-floor can become it's own apartment, complete with a kitchen, full bathroom, and a private entrance from the driveway. The one bedroom apartment is perfect for guests, an in-law suite, or as a rental unit. Outside, a fenced-in yard with a covered patio offers a private oasis for relaxing evenings. The private driveway leads to a spacious barn garage with three barn doors. The barn offers ample storage, space for a small vehicle, or could be used as a workshop. This home truly has it all, in the heart of Chestertown!

110 S Mill St, Chestertown

Listing courtesy of Gunther-McClary Real Estate. Contact:

Live where you play at 7712 Waterview Lane in sought-after Country Club Estates. Situated on just under an acre, this beautifully renovated, well-maintained Cape Cod is a quick bike ride to downtown Chestertown or an easy walk to the Chester River Yacht and Country Club. Timeless interior features, a main-floor primary suite, and practical indoor/outdoor living spaces make this the perfect home for everyday living or a weekend retreat. The well-designed first floor - featuring hardwoods, baseboards, and crown moldings throughout - is anchored by the open-concept kitchen and living room spaces, which flow naturally to the back sunroom and exterior deck. The renovated kitchen now features solid wood cabinets, quartz countertops, stainless steel appliances, recessed lighting, and overhanging bar seating. Cozy up with a book by the living room brick fireplace with a propane insert, surrounded by classic built-in bookshelves. Passing through the back sliding doors, you will be greeted by the sunroom and oversized back deck: each perfect for crab feasts and summer bbq's. Enjoy summer evenings while overlooking the private backyard, which is fully fenced-in and has plenty of space for dogs and children. The main floor also features a primary bedroom with an ensuite bath, a large walk-in closet, and a separate office. The renovated primary bath now features ceramic tile, a standing stall shower, wainscoting, double vanity, and new recessed lights. A dining room off the kitchen with a lovely bay window flows through a pocket door into the formal living room with built-in bookcases. The main floor is finished by a renovated powder room and laundry room just off the kitchen. Upstairs, you will find two more generously sized bedrooms, a full shared bath, and a potential 4th bedroom or office space for those who work from home. An attached two-car garage includes another half bath, additional storage, and a separate workroom for those who like to tinker. Mature trees provide lots of shade and privacy around the meticulously maintained front and back yards. A generously sized storage shed is perfect for garden tools and the lawnmower. Located on a quiet, dead-end street, the neighborhood is great for dog walkers and evening strolls. Improvements made by current owner: whole kitchen remodel including cabinets, countertops, appliances, hardwood floors (2019); primary bathroom and powder room remodel including ceramic tile, standing shower stall, toilets, wainscoting, double vanity, fixtures (2017), 14 windows replaced with double-pane insulated (2017); Carrier HVAC (2017); whole-house water filter and well pressure tank (2022); crawl space improvement (2016); and professional landscaping. Founded in 1706, Chestertown sits on the banks of the Chester River and is home to Washington College. Enjoy the historic architecture, local shopping, restaurants, art galleries, and waterfront parks. Chestertown is home to many festivals, an award-winning weekly Farmer's Market, and a laid-back lifestyle with an endless number of social or volunteer activities. Less than 90 minutes to Washington D.C. or Philadelphia. Enjoy country living on the Eastern Shore. Professional photos to come!

$665,000