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Charming Move-In Ready Colonial in the Heart of Town This beautifully updated Colonial blends timeless character with modern comfort. Ideally located within walking dist...
- 3 Beds
- 3 Baths
Listing courtesy of Taylor Properties. Contact:
Selling Office: .
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,...
- 4 Beds
- 3 Baths
Listing courtesy of Coldwell Banker Chesapeake Real Estate Company. Contact:
The Pearce House has been a testament to fine Eastlake Victorian architecture since it was constructed by famous early Eastern Shore builder H.M. Stuart for Judge James P...
- 4 Beds
- 3 Baths
Listing courtesy of Coldwell Banker Chesapeake Real Estate Company. Contact:
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
Listing courtesy of Coldwell Banker Chesapeake Real Estate Company. Contact:
✨ Historic Charm in the Heart of Downtown Chestertown ✨ Step back in time and discover the character, craftsmanship, and endless potential of this circa-1820 historic ho...
- 2 Beds
- 3 Baths
Listing courtesy of Benson & Mangold, LLC. Contact: 4108226665
Seller says sell! Massive price reduction ! Below market for this pristine home well situated in chestertown historic district! A rare Water Street opportunity—see yo...
- 4 Beds
- 3 Baths
Listing courtesy of TTR Sotheby's International Realty. Contact:
Selling Office: .
Newly constructed three-bedroom townhome with fantastic water views from the living level and bedrooms! Spacious open living space featuring a gourmet kitchen; 5-burner ...
- 3 Beds
- 4 Baths
Listing courtesy of Gunther-McClary Real Estate. Contact:
Rebuilt in 1863, the Tilley Residence showcases classic Second Empire architecture on one of Chestertown’s most prominent historic corners across from the Custom House, o...
- 5 Beds
- 5 Baths
Listing courtesy of Coldwell Banker Chesapeake Real Estate Company. Contact:
ALSO AVAILABLE FOR LEASE: Please reach out to agent for details. This charming 1916 home in Chestertown's historic district is in a quiet neighborhood next to Washington...
- 4 Beds
- 2 Baths
Listing courtesy of Long & Foster Real Estate, Inc.. Contact:
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 c...
- 1 Beds
- 1 Baths
Listing courtesy of Gunther-McClary Real Estate. Contact:
Selling Office: .
Fabulous location in the Chestertown Historic District with lots of room for expansion among brand new luxury homes! 420 Cannon sits on a 5,000 square foot lot that fron...
- 2 Beds
- 2 Baths
Listing courtesy of Doug Ashley Realtors, LLC. Contact:
Selling Office: .
Lovingly maintained, this charming home in Chestertown’s Historic District seamlessly blends classic character with modern comfort. Restored windows, original yellow hear...
- 4 Beds
- 2 Baths
Listing courtesy of Cross Street Realtors LLC. Contact:
Selling Office: .
The Vannort House stands proudly on historic Queen Street with a colonial-era smokehouse in the yard! Light & breezy: The 31' long screened-in side-porch has doors from ...
- 4 Beds
- 2 Baths
Listing courtesy of Doug Ashley Realtors, LLC. Contact:
Selling Office: .
This end unit waterfront condo in Scott's Point has beautiful water views up and down the Chester River! It is a light filled gem with water views from every window. It h...
- 3 Beds
- 4 Baths
Listing courtesy of Coldwell Banker Chesapeake Real Estate Company. Contact:
Selling Office: .
Step into this beautifully renovated 1,416 sq. ft., 2 bedrooms, 1.5 bath home in the heart of Chestertown. The building operated as the Johnson General Store into the 195...
- 2 Beds
- 2 Baths
Listing courtesy of Rock Hall Properties Real Estate. Contact:
Selling Office: .
This stunning renovation is the jewel of Chestertown's revitalized upper historic district! A beautiful view of Washington College (9th best college in the country by Pri...
- 4 Beds
- 4 Baths
Listing courtesy of Doug Ashley Realtors, LLC. Contact:
Selling Office: .
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 c...
- 2 Beds
- 1 Baths
Listing courtesy of Gunther-McClary Real Estate. Contact:
Selling Office: .
Embrace the walkable lifestyle of Chestertown in this completely renovated downtown gem from 1900. Experience both historic charm and modern amenities as this home has al...
- 3 Beds
- 2 Baths
Listing courtesy of Coldwell Banker Chesapeake Real Estate Company. Contact:
Selling Office: .
Charming and completely remodeled home in Historic Chestertown. Low maintenance with rare main floor living and off street parking with just enough yard! This home was...
- 2 Beds
- 1 Baths
Listing courtesy of Coldwell Banker Chesapeake Real Estate Company. Contact:
Selling Office: .
Prime historic district location! This fully furnished, prominent Church Alley address is completely turn-key for your immediate enjoyment! Circa 1880, 104 Church Alley...
- 2 Beds
- 2 Baths
Listing courtesy of Doug Ashley Realtors, LLC. Contact:
Selling Office: .
Your dream house awaits in the most perfect location! This delightful custom built home, being offered on one of the most sought after streets in Downtown Chestertown, an...
- 4 Beds
- 2 Baths
Listing courtesy of Doug Ashley Realtors, LLC. Contact:
Selling Office: .
Beautiful home with stately presence on a large corner parcel within Chestertown's Historic District. Mill Street offers privacy and quiet living in the heart of town. ...
- 4 Beds
- 4 Baths
Listing courtesy of Gunther-McClary Real Estate. Contact:
Selling Office: .Chestertown Historic District Real Estate & Homes
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