Available Listings

$395,000
Active

Chestertown Area Townhome

Active

349 High Street Chestertown, MD 21620

7 Bed
4 Baths
3664 sqft
MLS# MDKE2004076
A Rare Opportunity in the Heart of Historic ChestertownDiscover a truly special offering in the vibrant core of Chestertown’s Historic and Arts & Entertainment Districts. Owned by the same family for over 50 years, this multi-family property sits on a generous double lot known historically as the Laurence Lots—featured on original town maps and steeped in local heritage.Brimming with character and potential, the property currently features a townhouse on one side and two apartments on the other, offering a flexible layout ideal for renovation, income generation, or a creative reimagining. Whether you're envisioning a stately single-family residence, a dynamic live/work space, or a thoughtfully restored multi-unit investment, the possibilities are as expansive as the lot itself.That said, this is not a turnkey property. Significant settling has occurred over the years, and a substantial renovation will be required to bring it back to life. Offered strictly as-is, this is a true fixer-upper for the visionary buyer ready to take on a transformative project.Situated within both the Arts & Entertainment District and Enterprise Zone, this location supports both residential and commercial uses—making it an ideal candidate for those looking to merge lifestyle, business, and history.Bring your vision, creativity, and tools—and seize the chance to breathe new life into a piece of Chestertown’s storied past. Opportunities like this don’t come along often.Schedule your showing today and imagine the future you can build here.
Listing Courtesy of BRIGHT IDX / Coldwell Banker Chesapeake Real Estate Company / Cheryl Hurt
$395,000
Active

Chestertown Area Multi-Family Home

Active

349 &Amp 351 High Street Chestertown, MD 21620

Bed
0 Baths
3664 sqft
MLS# MDKE2003720
A Rare Opportunity in the Heart of Historic ChestertownDiscover a truly special offering in the vibrant core of Chestertown’s Historic and Arts & Entertainment Districts. Owned by the same family for over 50 years, this multi-family property sits on a generous double lot known historically as the Laurence Lots—featured on original town maps and steeped in local heritage.Brimming with character and potential, the property currently features a townhouse on one side and two apartments on the other, offering a flexible layout ideal for renovation, income generation, or a creative reimagining. Whether you're envisioning a stately single-family residence, a dynamic live/work space, or a thoughtfully restored multi-unit investment, the possibilities are as expansive as the lot itself.That said, this is not a turnkey property. Significant settling has occurred over the years, and a substantial renovation will be required to bring it back to life. Offered strictly as-is, this is a true fixer-upper for the visionary buyer ready to take on a transformative project.Situated within both the Arts & Entertainment District and Enterprise Zone, this location supports both residential and commercial uses—making it an ideal candidate for those looking to merge lifestyle, business, and history.Bring your vision, creativity, and tools—and seize the chance to breathe new life into a piece of Chestertown’s storied past. Opportunities like this don’t come along often.Schedule your showing today and imagine the future you can build here.
Listing Courtesy of BRIGHT IDX / Coldwell Banker Chesapeake Real Estate Company / Cheryl Hurt
$340,000
Pending

Rising Sun Area Residential Home

Pending

442 Telegraph Road Rising Sun, MD 21911

3 Bed
3 Baths
2072 sqft
MLS# MDCC2016704
Welcome Home to This Charming Farmhouse Retreat!Nestled just outside the quaint town of Rising Sun, this beautifully updated farmhouse offers the perfect blend of classic charm and modern upgrades. Situated on a spacious 0.88-acre lot, this property is ideal for those seeking peaceful country living with convenient access to town amenities. You won't ever have to worry about being snowed in, as the county will take care of your snow plow needs in the winter. Close proximity to the firehouse as well!Step onto the inviting front porch, perfect for relaxing evenings in a rocking chair while enjoying the serene surroundings. Inside, you'll find a warm and welcoming layout featuring 3 generously sized bedrooms, 1 full bathroom, and 2 convenient half baths. The heart of the home is the updated kitchen, complete with a large peninsula that offers ample counter space and room for bar stools—ideal for casual dining or entertaining. Adjacent to the kitchen, the formal dining and living rooms boast rich hardwood flooring and plenty of natural light. All bedrooms are located on the upper level, each offering comfortable space and easy access to the full bath. This home has seen several recent upgrades, including a new metal roof, new gutters and gutter guards, new siding, new windows, and a brand-new hot water heater (2025). Additionally, the property features an owned propane tank, offering added value and efficiency. Don’t miss the opportunity to own this delightful farmhouse filled with charm and thoughtful updates—your peaceful countryside retreat awaits!
Listing Courtesy of BRIGHT IDX / Chesapeake Real Estate Company / Brittany Lombardi
$339,000
Active

Still Pond Area Residential Home

Active

12776 Still Pond Road Still Pond, MD 21667

3 Bed
2 Baths
1735 sqft
MLS# MDKE2005116
Welcome to 12776 Still Pond Road: an endearing early 20th Century Victorian in the quiet town of Still Pond. This could be the perfect Eastern Shore retreat or full time residence. Historic Charm abounds with pocket doors, bay windows, 9 foot ceilings, hardwood floors, bullseye corner moldings, mahogany front porch, oak mantels, custom built-ins, and so much more. Enjoy rolling farmland views and picturesque sunsets from the front porch swinging bench. The sun-filled formal parlor flows seamlessly through the large pocket door into the dining room and kitchen. Follow the solid-wood staircase and railing upstairs to find 3 generously sized bedrooms and a 4th bedroom or office space. Massive 3rd floor could be finished for a 4th bedroom or den / game room. Recent upgrades include: architectural shingle roof, 6 mini-split systems for central heating and air, water conditioner, water heater, fireplace mantel with propane insert, and a brand new Fuji septic system. Almost 3/4 of an acre allows plenty of space for the dogs and kids to play. Open farmland surrounds for great views from any direction. Less than 90 minutes to Philadelphia and Washington D.C. 30 minutes to Middletown, Delaware and tax-free shopping. Close to Turners Creek State Park, Betterton Beach and the restaurants/marinas in Galena on the Sassafras River. Quick drive to historic downtown Chestertown. Founded in 1706, Chestertown sits on the banks of the Chester and is home to Washington College. Enjoy the historic homes, local shopping, restaurants, art galleries, and waterfront parks. Chestertown is home to many festivals, an award-winning weekly Farmer's Market, and a brand new YMCA with full gym, racquet sports, lap pool, sauna, etc. Enjoy country living on the Eastern Shore.
Listing Courtesy of BRIGHT IDX / Coldwell Banker Chesapeake Real Estate Company / Joseph Ciganek