Beautiful Brick Rancher in Great Oak Estates – Chestertown, MD Nestled on 1.33 acres in the desirable Great Oak Estates community, just a short walk or golf cart drive t...
- 3 Beds
- 3 Baths
- MDKE2005476 MLS
- 2,774 SqFt.
Listing courtesy of Chesapeake Real Estate Associates, LLC. Contact:
Selling Office: .
Your private retreat awaits! Nestled on nearly 4 acres in Worton, Maryland, this beautifully renovated Cape Cod offers the perfect blend of space, comfort, and functional...
- 4 Beds
- 2 Baths
- MDKE2005228 MLS
- 1,820 SqFt.
Listing courtesy of RE/MAX Executive. Contact:
Selling Office: .
Welcome to 591 Mill Lane in Galena, MD—your private country retreat set on 5.67 unrestricted acres of beautiful Eastern Shore landscape. This charming all-brick ranch st...
- 3 Beds
- 2 Baths
- MDKE2006248 MLS
- 2,046 SqFt.
Listing courtesy of Compass. Contact:
Selling Office: .
This cute as a button downtown stunner is recently updated and ready for the next owner to fall in love with the lifestyle that comes with living in the Historic District...
- 2 Beds
- 3 Baths
- MDKE2006674 MLS
- 1,476 SqFt.
Listing courtesy of Coldwell Banker Chesapeake Real Estate Company. Contact:
Selling Office: .
An amazing home located just a few blocks from Washington College! This mostly brick Cape Cod has 4 bedrooms, 3 full baths, formal dining room, living room with firepla...
- 4 Beds
- 3 Baths
- MDKE2006030 MLS
- 2,672 SqFt.
Listing courtesy of Doug Ashley Realtors, LLC. Contact:
Selling Office: .
Nestled in the charming Byford Development, this beautifully renovated home exudes warmth and comfort, making it the perfect retreat. With a thoughtful renovation complet...
- 4 Beds
- 3 Baths
- MDKE2006204 MLS
- 2,220 SqFt.
Listing courtesy of Cross Street Realtors LLC. Contact:
Selling Office: .
Welcome to this spacious 5-bedroom, 2.5 bath raised ranch located on picturesque Jim Davis Road in Galena, MD, offering peaceful country living on 2 acres with convenient...
- 5 Beds
- 3 Baths
- MDKE2006060 MLS
- 2,660 SqFt.
Listing courtesy of Remax Vision. Contact:
Selling Office: .
*Days on Market Reporting Incorrectly- Property listed Oct 30, 2025* Nestled just outside of historic Chestertown, minutes from farmers market, waterfront park and loca...
- 4 Beds
- 4 Baths
- MDKE2005636 MLS
- 2,492 SqFt.
Listing courtesy of Berkshire Hathaway HomeServices PenFed Realty. Contact:
Selling Office: .
Welcome to 14525 John Peel Road, a beautifully maintained home offering the perfect blend of elegance, comfort, and scenic surroundings in a highly desirable location. Se...
- 3 Beds
- 3 Baths
- MDKE2006056 MLS
- 1,932 SqFt.
Listing courtesy of Corner House Realty. Contact:
Selling Office: .
Welcome to 25428 Worton Lynch Road in Worton, Maryland! Situated on 1.28 acres, this charming 3-bedroom, 2.5-bath home offers comfortable living with thoughtful features ...
- 3 Beds
- 3 Baths
- MDKE2006692 MLS
- 1,872 SqFt.
Listing courtesy of Coldwell Banker Chesapeake Real Estate Company. Contact:
Selling Office: .
Welcome to 101 Birch Run Rd., Chestertown, MD! 3 Bedrooms | 2 Full Baths | Oversized 2-Car Garage | .42 Acres Discover this stunning full-brick rancher located in the he...
- 3 Beds
- 2 Baths
- MDKE2005810 MLS
- 1,961 SqFt.
Listing courtesy of Remax Vision. Contact:
Selling Office: .
Spacious waterfront rancher with pole barn—priced below appraised value for a quick sale! Appraised at $534K, this motivated seller is offering a rare opportunity for ins...
- 3 Beds
- 3 Baths
- MDKE2006150 MLS
- 1,821 SqFt.
Listing courtesy of Chesapeake Real Estate Associates, LLC. Contact:
Selling Office: .
311 Devon Drive is located in Coventry Farms; and being located within the Chestertown town limits offers town utilities. The front entrance welcomes you with an open tw...
- 4 Beds
- 3 Baths
- MDKE2005930 MLS
- 3,504 SqFt.
Listing courtesy of Doug Ashley Realtors, LLC. Contact:
Selling Office: .
Multiple offers received- Highest and Best due by 6/17 at noon! This property truly has a little something for everyone! Spacious 4-bedroom, 2-bath rancher situated on 1....
- 4 Beds
- 2 Baths
- MDKE2006570 MLS
- 1,680 SqFt.
Listing courtesy of Chesapeake Real Estate Associates, LLC. Contact:
Selling Office: .
Open House Friday July 3rd 4-6pm! Located on Water Street in the heart of Chestertown's premier waterfront historic district, this beautiful two-bedroom, two-bath condomi...
- 2 Beds
- 2 Baths
- MDKE2006680 MLS
- 1,011 SqFt.
Listing courtesy of Northrop Realty. Contact:
Selling Office: .
Enjoy three bedrooms on the main floor, including a spacious primary suite with its own private bath. The open-concept main living area seamlessly connects the kitchen, f...
- 4 Beds
- 4 Baths
- MDKE2006124 MLS
- 2,186 SqFt.
Listing courtesy of Chesapeake Real Estate Associates, LLC. Contact:
Selling Office: .
Impeccably maintained! One-level home offers easy living on a quiet street. Thoughtful updates and meticulous care are evident throughout, including a new vapor barrier i...
- 3 Beds
- 2 Baths
- MDKE2005546 MLS
- 1,886 SqFt.
Listing courtesy of Cross Street Realtors LLC. Contact:
Selling Office: .
The famous Durding's Building in Rock Hall is a landmark property with four rental units. This property was originally an apothecary with a popular soda fountain that con...
- MDKE2005994 MLS
Listing courtesy of Rock Hall Properties Real Estate. Contact:
Selling Office: .
Crew's Landing 3 bedroom Townhouse, located in Betterton, The Jewel of the Chesapeake. This 12 unit complex has become a premier waterfront community on the upper Bay. ...
- 3 Beds
- 3 Baths
- MDKE2006230 MLS
Listing courtesy of Gunther-McClary Real Estate. Contact:
Selling Office: .
A perfect pied-a-terre or full time residence, this adorable historic home is just steps from the farmers market, shops, restaurants, theater,art galleries and the Cheste...
- 2 Beds
- 2 Baths
- MDKE2006900 MLS
- 1,058 SqFt.
Listing courtesy of Coldwell Banker Chesapeake Real Estate Company. Contact:
Selling Office: .
Charming Rancher with Private Backyard Oasis in Byford Estates 206 Barroll Drive, Chestertown, MD Located in the highly desirable Byford Estates community, this well-main...
- 3 Beds
- 2 Baths
- MDKE2005094 MLS
- 1,820 SqFt.
Listing courtesy of Cross Street Realtors LLC. Contact:
Selling Office: .
Back on the market at no fault of seller. Rigbie Bluff is the perfect maintenance-free community in the quiet waterfront town of Betterton; known as the Jewel of the Che...
- 3 Beds
- 2 Baths
- MDKE2005008 MLS
- 2,000 SqFt.
Listing courtesy of Coldwell Banker Chesapeake Real Estate Company. Contact:
Selling Office: .
Price improvement! Located in Country Club Estates, on a lovely, corner lot with mature trees. Solid brick rancher with good bones. 3 bedrooms, 2 full baths. The basement...
- 3 Beds
- 2 Baths
- MDKE2005632 MLS
- 2,162 SqFt.
Listing courtesy of Coldwell Banker Chesapeake Real Estate Company. Contact:
Selling Office: .
Lovely countryside Cape Cod on over 3 private acres. Sit on the front porch and enjoy the summer breeze or grill off the back deck and watch the deer in the woods. This...
- 3 Beds
- 2 Baths
- MDKE2005230 MLS
- 1,788 SqFt.
Listing courtesy of Coldwell Banker Chesapeake Real Estate Company. Contact:
Selling Office: .
This charming 1916 home in Chestertown's historic district is in a quiet neighborhood next to Washington College, just a short walk from downtown and the waterfront. Thre...
- 4 Beds
- 2 Baths
- MDKE2005876 MLS
- 1,656 SqFt.
Listing courtesy of Long & Foster Real Estate, Inc.. Contact:
Selling Office: .
*****PRICED $30,000 UNDER THE RECENT APPRAISED VALUE***** One floor living, a wood burning fireplace, and hardwood floors help this represent the cozy but elevated Easte...
- 3 Beds
- 2 Baths
- MDKE2006316 MLS
- 1,588 SqFt.
Listing courtesy of Coldwell Banker Chesapeake Real Estate Company. Contact:
Selling Office: .
Adorable updated cottage in the heart of town on popular Bayside Avenue offering approximately 1,400 sq. ft. of charming coastal living. This delightful Cape Cod features...
- 3 Beds
- 2 Baths
- MDKE2006568 MLS
- 1,400 SqFt.
Listing courtesy of Rock Hall Properties Real Estate. Contact:
Selling Office: .
Charming Cape Cod nestled on a beautiful 2-acre lot offering the perfect blend of space, privacy, and timeless charm! This well-maintained home features a long driveway, ...
- 4 Beds
- 2 Baths
- MDKE2006514 MLS
- 1,512 SqFt.
Listing courtesy of Coldwell Banker Realty. Contact:
Selling Office: .
Welcome to this beautifully updated 3-bedroom, 1.5-bath rancher offering 1,344 sq ft of comfortable, energy-efficient living. Thoughtfully improved since 2018, this home ...
- 3 Beds
- 2 Baths
- MDKE2006292 MLS
- 1,344 SqFt.
Listing courtesy of Rock Hall Properties Real Estate. Contact:
Selling Office: .
Experience the best of in-town Chestertown living in this custom-built single-level home! The open floor plan features abundant natural light, gleaming hardwood floors an...
- 3 Beds
- 3 Baths
- MDKE2005824 MLS
- 1,676 SqFt.
Listing courtesy of Coldwell Banker Chesapeake Real Estate Company. Contact:
Selling Office: .