Spacious, Stylish, and Designed for Real Life – Discover the perfect blend of comfort, flexibility, and convenience in this expansive 4-bedroom home, tucked into the soug...
- 4 Beds
- 3 Baths
- MDKE2005500 MLS
- 3,820 SqFt.
Listing courtesy of TTR Sotheby's International Realty. Contact:
Selling Office: .
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: .
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: .
Only 500 steps from the center of Chestertown (5-minute walk) to this early 20th C gem of a traditional "Four Square". This prominent STAND-OUT RESIDENCE, crafted by acc...
- 4 Beds
- 4 Baths
- MDKE2005538 MLS
- 2,917 SqFt.
Listing courtesy of Cross Street Realtors LLC. Contact:
Selling Office: .
109 South Water, along with the historic Custom House, is a bookend to a small, but iconic, cluster of historic (c1900) townhouses that give pause to every passer-by, esp...
- 4 Beds
- 2 Baths
- MDKE2006064 MLS
- 2,064 SqFt.
Listing courtesy of Cross Street Realtors LLC. Contact:
Selling Office: .
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: .
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
- 2,506 SqFt.
Listing courtesy of Coldwell Banker Chesapeake Real Estate Company. Contact:
Selling Office: .
Country Club Estates - Live Where You Play – Just 1.5 Miles from Downtown Chestertown! Enjoy the ease of one-level living in a prime location near the Chester River Yacht...
- 3 Beds
- 3 Baths
- MDKE2005552 MLS
- 2,280 SqFt.
Listing courtesy of Cross Street Realtors LLC. Contact:
Selling Office: .
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: .
Price improvement! Prepare to be wowed when you walk through the front door. Gleaming hardwood floors, huge floor-to-ceiling windows, high-end kitchen and primary bath. ...
- 4 Beds
- 2 Baths
- MDKE2005762 MLS
- 2,869 SqFt.
Listing courtesy of Coldwell Banker Chesapeake Real Estate Company. Contact:
Selling Office: .
Looking for a large spacious home in a lovely neighborhood that is close to downtown & shopping, 20 min from Rt. 301, within 2 miles of the Chester River...Look no furthe...
- 4 Beds
- 4 Baths
- MDKE2005594 MLS
- 3,676 SqFt.
Listing courtesy of Douglas Realty LLC. Contact:
Selling Office: .
Stunning waterfront property with private dock site on the Chester River. The house has been gutted and needs a complete rehab, or it can be removed and rebuilt to suit ...
- 3 Beds
- 3 Baths
- MDKE2005422 MLS
- 1,600 SqFt.
Listing courtesy of Coldwell Banker Chesapeake Real Estate Company. Contact:
Selling Office: .
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: .
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: .
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: .
$20,000 Price Reduction! A One-of-a-Kind Historic Treasure Reimagined for Modern Living Step into history with this extraordinary Greek Revival chapel, originally built i...
- 1 Beds
- 1 Baths
- MDKE2005028 MLS
- 1,148 SqFt.
Listing courtesy of Hyatt & Company Real Estate, LLC. Contact:
Selling Office: .
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
- 1,949 SqFt.
Listing courtesy of Shoreline Realty. Contact:
Selling Office: .
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: .
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: .
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: .
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: .
*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 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: .
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: .
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: .
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: .