Welcome to the epitome of Eastern Shore waterfront luxury, offered for the first time in almost 60 years. This stunning 11-acre estate offers an unparalleled lifestyle, f...
- 3 Beds
- 4 Baths
- MDKE2006468 MLS
- 3,142 SqFt.
Listing courtesy of TTR Sotheby's International Realty. Contact:
Selling Office: Coldwell Banker Realty.
Price Improvement! Spectacular waterfront on the Chester River!! Words can't describe the uniqueness of this property. With the historic charm of an older home but hig...
- 5 Beds
- 5 Baths
- MDKE2005590 MLS
- 4,305 SqFt.
Listing courtesy of Coldwell Banker Chesapeake Real Estate Company. Contact:
Selling Office: Long & Foster Real Estate, Inc..
None
- 5 Beds
- 3 Baths
- MDKE2006542 MLS
- 2,700 SqFt.
Listing courtesy of TTR Sotheby's International Realty. Contact:
Selling Office: Davis Real Estate, Inc..
Experience the best of waterfront living just steps outside of the heart of Downtown Chestertown. Only a few blocks from shops, restaurants, the bustling farmers market, ...
- 5 Beds
- 3 Baths
- MDKE2005900 MLS
- 2,956 SqFt.
Listing courtesy of TTR Sotheby's International Realty. Contact:
Selling Office: RE/MAX Chesapeake.
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 & Coun...
- 4 Beds
- 4 Baths
- MDKE2006350 MLS
- 4,145 SqFt.
Listing courtesy of Taylor Properties. Contact:
Selling Office: Unrepresented.
None
- 3 Beds
- 3 Baths
- MDKE2006358 MLS
- 3,136 SqFt.
Listing courtesy of Coldwell Banker Chesapeake Real Estate Company. Contact:
Selling Office: Cross Street Realtors LLC.
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
- MDKE2006744 MLS
- 2,730 SqFt.
Listing courtesy of Coldwell Banker Chesapeake Real Estate Company. Contact:
Selling Office: Coldwell Banker Chesapeake Real Estate Company.
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 an...
- 3 Beds
- 5 Baths
- MDKE2006496 MLS
- 3,047 SqFt.
Listing courtesy of Coldwell Banker Chesapeake Real Estate Company. Contact:
Selling Office: Cross Street Realtors LLC.
***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*** Th...
- 3 Beds
- 4 Baths
- MDKE2006890 MLS
- 4,037 SqFt.
Listing courtesy of Chesapeake Real Estate Associates, LLC. Contact:
Selling Office: Unrepresented.
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...
- 3 Beds
- 2 Baths
- MDKE2006324 MLS
- 1,566 SqFt.
Listing courtesy of Coldwell Banker Chesapeake Real Estate Company. Contact:
Selling Office: RE/MAX Chesapeake.
An impeccably maintained, perfectly positioned two bedroom, two and one-half bath condo featuring one of the best vistas of Chestertown and the Chester River. Here, body...
- 2 Beds
- 3 Baths
- MDKE2006084 MLS
- 1,600 SqFt.
Listing courtesy of Cross Street Realtors LLC. Contact:
Selling Office: Coldwell Banker Chesapeake Real Estate Company.
Welcome to 118 Little Harbor Way #202, a beautifully reimagined waterfront condo offering effortless living and sweeping panoramic views of the Chester River. Located in ...
- 3 Beds
- 2 Baths
- MDKE2005800 MLS
- 1,600 SqFt.
Listing courtesy of Benson & Mangold, LLC. Contact:
Selling Office: Doug Ashley Realtors, LLC.
Beautifully Updated Home in a Serene Setting! Welcome to this stunning home filled with thoughtful improvements and timeless charm. The spacious Florida room overlooks a...
- 4 Beds
- 3 Baths
- MDKE2005796 MLS
- 3,248 SqFt.
Listing courtesy of Doug Ashley Realtors, LLC. Contact:
Selling Office: Coldwell Banker Chesapeake Real Estate Company.
Rare lakefront opportunity in Kent County offering exceptional privacy and a peaceful natural setting. Tucked away on 2.62 partially wooded acres along Urieville Lake, th...
- 4 Beds
- 4 Baths
- MDKE2004586 MLS
- 3,684 SqFt.
Listing courtesy of Coldwell Banker Chesapeake Real Estate Company. Contact:
Selling Office: LPT Realty, LLC.
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
- MDKE2006676 MLS
- 4,536 SqFt.
Listing courtesy of Coldwell Banker Chesapeake Real Estate Company. Contact:
Selling Office: Cross Street Realtors LLC.
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
- MDKE2006058 MLS
- 2,008 SqFt.
Listing courtesy of TTR Sotheby's International Realty. Contact:
Selling Office: Coldwell Banker Chesapeake Real Estate Company.
Prime location in Downtown Chestertown’s Historic District offering approximately 1,785 square feet of practical office and workspace on three levels with 4 off-street pa...
- MDKE2006536 MLS
Listing courtesy of Cross Street Realtors LLC. Contact:
Selling Office: Cross Street Realtors LLC.
Prime location in Downtown Chestertown’s Historic District offering approximately 1,785 square feet of practical living space on three levels with 4 off-street parking sp...
- 3 Beds
- 2 Baths
- MDKE2006520 MLS
- 1,785 SqFt.
Listing courtesy of Cross Street Realtors LLC. Contact:
Selling Office: Cross Street Realtors LLC.
Welcome to 9816 Fairlee Road. Be Sure to Click the Virtual Tour!! This property has been meticulously cared for by the current owners and it shows. The property sits on 6...
- 3 Beds
- 3 Baths
- MDKE2006488 MLS
- 1,624 SqFt.
Listing courtesy of Long & Foster Real Estate, Inc.. Contact:
Selling Office: Coldwell Banker Chesapeake Real Estate Company.
Recently updated "coastal" home located in a small community of 8 homes , three miles east of historic Chestertown. The house sits on high ground, less than a mile from...
- 3 Beds
- 3 Baths
- MDKE2006820 MLS
- 2,824 SqFt.
Listing courtesy of Shoreline Realty. Contact:
Selling Office: Doug Ashley Realtors, LLC.
Nestled in the desirable Crestview neighborhood, this beautifully maintained rancher built by respected local builder KRM Construction offers the perfect blend of quality...
- 3 Beds
- 2 Baths
- MDKE2006516 MLS
- 1,817 SqFt.
Listing courtesy of Cross Street Realtors LLC. Contact:
Selling Office: Doug Ashley Realtors, LLC.
Nestled in the natural serene of Great Oak Estates, this beautiful 5 bedroom, 3.5 bathroom Nanticoke Home offers a flexible floor plan, updated kitchen, spacious backyard...
- 5 Beds
- 4 Baths
- MDKE2006478 MLS
- 2,688 SqFt.
Listing courtesy of Doug Ashley Realtors, LLC. Contact:
Selling Office: Compass Realty, Inc..
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: Long & Foster Real Estate, Inc..
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: Benson & Mangold, LLC.
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
- 3,984 SqFt.
Listing courtesy of Doug Ashley Realtors, LLC. Contact:
Selling Office: Cross Street Realtors LLC.
*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
- 3,799 SqFt.
Listing courtesy of Berkshire Hathaway HomeServices PenFed Realty. Contact:
Selling Office: Keller Williams Gateway LLC.
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: Cross Street Realtors LLC.
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: Cross Street Realtors LLC.
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: Samson Properties.
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: Unrepresented.