Chestertown Property Listings

Real Estate

Chestertown

Perc approved lot for sale in Chesapeake Landing. A total of .34 combined with both lots. Community has a voluntary HOA giving you access to the boat ramp, marina and a slip for an extra fee.

Price: $29,000

View additional photos »

Please call 410-275-2118 to speak with a representative about this property or fill out the form on the contact page.

Chestertown

Charming Historic Chestertown investment opportunity! Once updated this building can accommodate two street-front shops, a first floor one bedroom apartment, as well as a spacious apartment upstairs. Back deck overlooks sweet courtyard, perfect for relaxing. GREAT location and tons of character - enjoy the Chestertown Farmer's Market year round, the Chester River just a few blocks away, shops and restaurants right down the street - you cannot beat this Historic District location and opportunity. Seller has removed plaster walls downstairs and updated the electric. Other updates include: exterior painting, new metal roof and a new deck with entry to second floor apartment.

Price: $349,000

View additional photos »

Please call 410-639-2118 to speak with a representative about this property or fill out the form on the contact page.

Chestertown

This exquisitely renovated 1800s home showcases the timeless elegance of its original architecture. Every detail has been restored to its former glory. No expense has been spared in selecting the finest finishes and materials for this renovation and it extends beyond the interior, with the creation of an outdoor oasis. This meticulously landscaped gardens and charming patio provide a private retreat right in the heart of Historic Downtown Chestertown. Chestertown is conveniently located on Maryland's Eastern Shore, less 80 miles from Washington DC and 90 miles from Philadelphia

Price: $950,000

View additional photos »

Please call 410-275-2118 to speak with a representative about this property or fill out the form on the contact page.

Chestertown

This exquisitely renovated 1800s 2 Bedroom home showcases the timeless elegance of its original architecture. Every detail has been restored to its former glory with preserving its charm and character of its historic roots while incorporating modern updates for a truly exception living experience. Located in the heart of Chestertown with very easy walk to shops, restaurants, parks and just two blocks from the Chester River waterfront. Chestertown is conveniently located on Maryland's Eastern Shore, less 80 miles from Washington DC and 90 miles from Philadelphia

Price: $625,000

View additional photos »

Please call 410-275-2118 to speak with a representative about this property or fill out the form on the contact page.

Chestertown

Lot 3 located at the midway point of Fairway #10, a perfect spot to enter the back nine and head to the club house for lunch or dinner (membership required) Prestwick offers the best in eastern shore living with the small town charm of Chestertown Md, yet only 1 to 2 hours from Wilmington, Philadelphia, Baltimore and Washington DC. Join the club and have access to the great golfing, club pool, marina (with boat slips) and boat ramp or just launch the boat, paddle board or kayak at the new town marina or the many county owned ramps. Design and build the home you want with one of the area s finest builders.

Price: $150,000

View additional photos »

Please call 410-275-2118 to speak with a representative about this property or fill out the form on the contact page.

Chestertown

Location (3 fairway lots available), Location (minutes from historic Chestertown), Location (easy access to pristine waterways of Maryland s eastern shore). Two other interior lots available including two corner locations. Lot 4 overlooks two greens on on hole #10 the other on # 5 with fairway boarders on two sides. Prestwick offers the best in eastern shore living with the small town charm of Chestertown Md, yet only 1 to 2 hours from Wilmington, Philadelphia, Baltimore and Washington DC. Join the club and have access to the great golfing, club pool, marina (with boat slips) and boat ramp or just launch the boat, paddle board or kayak at the new town marina or the many county owned ramps. Design and build the home you want with one of the areas finest builders

Price: $175,000

View additional photos »

Please call 410-275-2118 to speak with a representative about this property or fill out the form on the contact page.

Chester River

A stately 1800’s waterfront Victorian home, rich in history enters a new chapter in life with 6 new condominium units. Make sure to bring all you water toys or a lounge chair to relax on the banks of Chester River. All the units have been renovated with with upgraded bathrooms and brand new kitchens. Enjoy all the amenities of living waterfront--Community dock, kayak storage, patio, and your own ground level storage. This is a unique setting offering waterfront living in downtown historic Chestertown and includes off street parking. Walk to downtown restaurants and shops. Beautiful southeast views of the Chester River with spectacular sunrises and plenty of year-round sunshine. Take in the all of the nearly year-round waterfront activities from your own back yard, including Chestertown Tea Party, 4th of July fireworks and Sultana down rigging weekend. Located on Maryland’s scenic eastern shore less than 85 miles from Washington DC to the south or Philadelphia to the north, this home is the perfect meeting spot for those living in the Mid-Atlantic region. 5 Units ranging from 1-2 bedrooms

Price: Starting @ $385,000

View additional photos »

Please call 410-275-2118 to speak with a representative about this property or fill out the form on the contact page.

Chestertown

Newly constructed 3 Bedroom townhouses with nearly all the desired attributes of town living, with water views and access from the marina on one side and waterfront park on the other. Walk to downtown shops and restaurants, just a few blocks away.

Price: Starting @ $950,000

View additional photos »

Please call 410-275-2118 to speak with a representative about this property or fill out the form on the contact page.