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.
This charming 1916 home in Chestertown's historic district is in a quiet neighborhood next to Washington College, just a short walk from downtown and the waterfront. Thre...
- 4 Beds
- 2 Baths
- MDKE2005876 MLS
- 1,656 SqFt.
Listing courtesy of Long & Foster Real Estate, Inc.. Contact:
Selling Office: Benson & Mangold, LLC.
*****PRICED $30,000 UNDER THE RECENT APPRAISED VALUE***** One floor living, a wood burning fireplace, and hardwood floors help this represent the cozy but elevated Easte...
- 3 Beds
- 2 Baths
- MDKE2006316 MLS
- 1,588 SqFt.
Listing courtesy of Coldwell Banker Chesapeake Real Estate Company. Contact:
Selling Office: Blackwell Real Estate, LLC.
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
- MDKE2006040 MLS
- 1,216 SqFt.
Listing courtesy of Taylor Properties. Contact:
Selling Office: LPT Realty, LLC.
Well maintained Beautiful Brick Rancher nestled on 2.16 Acres in Chestertown and a short distance to Historic Downtown. 3 Spacious Bedrooms all with Hardwood Flooring an...
- 3 Beds
- 2 Baths
- MDKE2006526 MLS
- 1,440 SqFt.
Listing courtesy of Keller Williams Realty. Contact:
Selling Office: Coldwell Banker Chesapeake Real Estate Company.
Custom-Perfected Home with Luxury Finishes — Without the Luxury Price This beautifully reimagined 3-bedroom, 2-bath home (1,512 sq. ft.) sits on a generous .34-acre lot...
- 3 Beds
- 2 Baths
- MDKE2006486 MLS
- 1,512 SqFt.
Listing courtesy of Coldwell Banker Chesapeake Real Estate Company. Contact:
Selling Office: Compass.
NEW PRICE – One of Chestertown's Best Values! Over 2,500 square feet of 2023 construction priced comparably to many older Chestertown homes with just 1,200–1,800 square f...
- 5 Beds
- 4 Baths
- MDKE2006510 MLS
- 2,534 SqFt.
Listing courtesy of CENTURY 21 New Millennium. Contact:
Selling Office: RE/MAX Advantage Realty.
Charming and full of potential, this 3-bedroom, 1.5-bath Cape Cod home offers a prime in-town Chestertown location with thoughtful updates already in place. New roof (Dec...
- 3 Beds
- 2 Baths
- MDKE2006332 MLS
- 1,404 SqFt.
Listing courtesy of TTR Sotheby's International Realty. Contact:
Selling Office: Cross Street Realtors LLC.
Well situated 70s Ranch. Original kitchen and baths. Hardwood floors. 3 beds, 2 baths.
- 3 Beds
- 2 Baths
- MDKE2006784 MLS
- 1,934 SqFt.
Listing courtesy of Coldwell Banker Chesapeake Real Estate Company. Contact:
Selling Office: TTR Sotheby's International Realty.
Tucked neatly on a corner in Chesapeake Landing, this three-quarter acre parcel is among one of the largest in the neighborhood. The 2020 custom built home exudes simple ...
- 3 Beds
- 2 Baths
- MDKE2006096 MLS
- 1,248 SqFt.
Listing courtesy of TTR Sotheby's International Realty. Contact:
Selling Office: Rosendale Realty.
A Rare Opportunity in the Heart of Historic Chestertown Discover a truly special offering in the vibrant core of Chestertown’s Historic and Arts & Entertainment District...
- MDKE2003720 MLS
- 3,664 SqFt.
Listing courtesy of Coldwell Banker Chesapeake Real Estate Company. Contact:
Selling Office: Taylor Properties.
None
- 3 Beds
- 3 Baths
- MDKE2006154 MLS
- 1,724 SqFt.
Listing courtesy of American Premier Realty, LLC. Contact:
Selling Office: American Premier Realty, LLC.
Welcome to “The Cottage,” as it’s affectionately known! This charming home offers beautiful water views of the Chesapeake Bay, creating a peaceful and relaxing place to c...
- 2 Beds
- 1 Baths
- MDKE2006198 MLS
- 1,294 SqFt.
Listing courtesy of Doug Ashley Realtors, LLC. Contact:
Selling Office: Douglas Realty LLC.
AGENTS - PLEASE VIEW AGENT REMARKS IN BRIGHT MLS. This beautifully renovated 3-bedroom, 2-bath Fairlee home is a true gem, perfectly situated on a private 2-acre lot tha...
- 3 Beds
- 2 Baths
- MDKE2006682 MLS
- 1,296 SqFt.
Listing courtesy of Keller Williams Legacy. Contact:
Selling Office: Samson Properties.
Price Improvement = Even More Value! Discover the perfect blend of space, privacy, and comfort at this well-maintained 3-bedroom, 2-bath, 1,900 square foot home, situated...
- 3 Beds
- 2 Baths
- MDKE2005834 MLS
- 1,900 SqFt.
Listing courtesy of Chesapeake Real Estate Associates, LLC. Contact:
Selling Office: EXIT Preferred Realty.
OPEN HOUSE SATURDAY 3/7/26 FROM 11am-1pm HOPE TO SEE YOU THERE !!! Enjoy easy single-story living in this well-maintained 3-bedroom, 2-bath home situated on a ½-acre lot...
- 3 Beds
- 2 Baths
- MDKE2006062 MLS
- 1,628 SqFt.
Listing courtesy of Benson & Mangold, LLC. Contact:
Selling Office: Coldwell Banker Chesapeake Real Estate Company.
Bring your vision and transform this unique property into the home of your dreams. Situated on 3.79 picturesque acres, the property features a beautiful one-acre stocked ...
- 3 Beds
- 2 Baths
- MDKE2006854 MLS
- 3,292 SqFt.
Listing courtesy of Pearson Smith Realty, LLC. Contact:
Selling Office: LPT Realty, LLC.
Turnkey Perfection! Fully Renovated Ranch Home in Desirable Fairlee! Prepare to be impressed by this stunning ranch home that has undergone a complete, top-to-bottom reno...
- 3 Beds
- 1 Baths
- MDKE2005676 MLS
- 1,805 SqFt.
Listing courtesy of Real Broker LLC. Contact:
Selling Office: Doug Ashley Realtors, LLC.
Offers due Wednesday 4/22 by 6PM! Welcome to this beautifully upgraded 3-bedroom, 2-bath Cape Cod, just six years young and perfectly situated in the sought-after Chesape...
- 3 Beds
- 2 Baths
- MDKE2006378 MLS
- 1,499 SqFt.
Listing courtesy of Chesapeake Real Estate Associates, LLC. Contact:
Selling Office: Unrepresented.
Welcome home to 10572 Watonga Road, a charming Cape Cod nestled on a beautifully wooded corner lot in the desirable Chesapeake Landing community. Built in 2007 and meticu...
- 3 Beds
- 2 Baths
- MDKE2006644 MLS
- 1,404 SqFt.
Listing courtesy of Serhant. Contact:
Selling Office: Long & Foster Real Estate, Inc..
None
- 3 Beds
- 1 Baths
- MDKE2006538 MLS
- 1,427 SqFt.
Listing courtesy of TTR Sotheby's International Realty. Contact:
Selling Office: Chesapeake Real Estate Associates, LLC.
Welcome to 102 Flying Cloud a new community known as The Village of Chestertown. This is a rare opportunity to own a home at this price and condition. Designed to with an...
- 3 Beds
- 3 Baths
- MDKE2006586 MLS
- 1,896 SqFt.
Listing courtesy of Long & Foster Real Estate, Inc.. Contact:
Selling Office: Coldwell Banker Chesapeake Real Estate Company.
Welcome to Chesapeake Landing — where new construction meets timeless Cape Cod charm in the heart of Chestertown, MD. This brand-new 3 BR / 2.5 BA home at 10584 Klamath R...
- 3 Beds
- 2 Baths
- MDKE2006328 MLS
Listing courtesy of Real Broker, LLC - Chester. Contact:
Selling Office: Chesapeake Real Estate Associates, LLC.
Charming Single-Level Home in the Heart of Walkable Chestertown. Welcome to one of Chestertown's most convenient addresses — a quaint, single-level, three-bedroom home se...
- 3 Beds
- 3 Baths
- MDKE2006792 MLS
- 1,397 SqFt.
Listing courtesy of TTR Sotheby's International Realty. Contact:
Selling Office: Chesapeake Real Estate Associates, LLC.
Welcome to 10720 Foreston Rd, a charming and inviting home situated in the peaceful surroundings of Chesapeake Landing in Chestertown, MD. 3 bedrooms and 2 full bathroom...
- 3 Beds
- 2 Baths
- MDKE2006800 MLS
- 1,412 SqFt.
Listing courtesy of Compass. Contact:
Selling Office: Taylor Properties.
Welcome to this charming 4-bedroom rancher nestled in the heart of historic Chestertown, offering the perfect blend of peaceful rural living and convenient access to town...
- 4 Beds
- 2 Baths
- MDKE2006482 MLS
- 1,325 SqFt.
Listing courtesy of Redfin Corporation. Contact:
Selling Office: Chesapeake Real Estate Associates, LLC.
This beautifully maintained end-unit townhome, owned by its original owner, has been meticulously cared for and is now ready for its next chapter. The end-unit location p...
- 2 Beds
- 3 Baths
- MDKE2006224 MLS
- 1,867 SqFt.
Listing courtesy of Doug Ashley Realtors, LLC. Contact:
Selling Office: Chesapeake Real Estate Associates, LLC.
Discover this beautifully renovated ranch-style home (2023), offering 1,152 square feet of thoughtfully updated living space. The open floor plan creates a seamless flow ...
- 3 Beds
- 2 Baths
- MDKE2006170 MLS
- 1,152 SqFt.
Listing courtesy of Chesapeake Real Estate Associates, LLC. Contact:
Selling Office: Foraker Realty Co..
Escape to the Eastern Shore! Nestled among mature trees on a .41 acre wooded lot, this charming Cape Cod-style home offers the perfect blend of privacy, comfort, and East...
- 2 Beds
- 2 Baths
- MDKE2006858 MLS
- 1,500 SqFt.
Listing courtesy of Cross Street Realtors LLC. Contact:
Selling Office: Cross Street Realtors LLC.
✨ 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
- MDKE2006614 MLS
- 1,518 SqFt.
Listing courtesy of Benson & Mangold, LLC. Contact:
Selling Office: CR Realty.