Address	Bed / Bath	Listing Price
611 CANNON STREET This 2-bedroom, 1.5-bath bungalow offers a bright, open layout with updates throughout. The home features a sun-filled front room, an eat-in kitchen with new butcher block seating and updated appliances, and a fully renovated bathroom with new tile and a modern vanity. A rear utility room with laund CHESTERTOWN, MD Living Area: 920 Sqft.	2 Beds, 2 Baths	$299,000
105 HIGH STREET This masterpiece is finally complete. Rebuilt in 1863, the Tilley Residence showcases classic Second Empire style on one of Chestertown’s most prominent corners, neighboring Widehall and the Custom House. Expertly restored in 2024–2025 by one of Kent County’s premier builders, the home offers CHESTERTOWN, MD Living Area: 3243 Sqft.	5 Beds, 5 Baths	$1,395,500
222 MOUNT VERNON AVENUE Motivated sellers - bring us an offer! This historic 1916 home is charming inside and out. They don’t build houses like this anymore! Featuring 4 bedrooms and 2 full baths, this home is adjacent to Washington College and a short stroll to downtown Chestertown. Three finished levels and high ceilin CHESTERTOWN, MD Living Area: 1656 Sqft.	4 Beds, 2 Baths	$470,000
109 S COLLEGE AVENUE Charming Move-In Ready Colonial in the Heart of Town This beautifully updated Colonial blends timeless character with modern comfort. Ideally located within walking distance of local restaurants, shops, and the scenic waterfront, it offers the perfect combination of charm and convenience. The exte CHESTERTOWN, MD Living Area: 1216 Sqft.	3 Beds, 3 Baths	$449,900
7844 CHESTER COURT 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 private, beautifully landscaped backyard — your own personal oasis. This room offers unlimited views of the back yard, which w CHESTERTOWN, MD Living Area: 3248 Sqft.	4 Beds, 3 Baths	$770,000
206 S WATER STREET Live in the heart of Chestertown’s Historic District—see your boat from your front porch! Beautifully rebuilt and expanded, this versatile home offers 3 1/2 baths and over 2,000 sq. ft. of finished living space. The rear addition features a sunroom/mudroom with separate entrance leading to a gu CHESTERTOWN, MD Living Area: 2008 Sqft.	4 Beds, 4 Baths	$619,000
7989 QUAKER NECK ROAD 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 high end modern upgrades, you will be living the life of luxury. Spacious rooms, magnificent views of the Chester River and your pr CHESTERTOWN, MD Living Area: 4305 Sqft.	5 Beds, 5 Baths	$2,500,000
200 WASHINGTON AVENUE 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 acclaimed master builder Walter Pippin, extends a warm welcome to anyone driving (only 25mph please!) or strolling from the college c CHESTERTOWN, MD Living Area: 2917 Sqft.	4 Beds, 4 Baths	$695,000
141 PROSPECT STREET INTOWN Investor Special! This 4-bedroom, 1.5-bath bungalow is full of potential and ready for your vision. Situated on a large, private lot at the end of a quiet street, the home offers solid bones and a detached garage/workshop area that is hard to find! Located just minutes from Chestertown and Wa CHESTERTOWN, MD Living Area: 1156 Sqft.	4 Beds, 2 Baths	$167,000
108 S KENT STREET Price improvement! Cute as a button in the historic district on South Kent St. This 1-bedroom, 1.5 bath home is in the center of town, within walking distance to the farmers market and all the shops and restaurants. Just 4 blocks from Chestertown's waterfront promenade. Upstairs is a large, sun-fill CHESTERTOWN, MD Living Area: 936 Sqft.	1 Bed, 2 Baths	$315,000
132 PROSPECT STREET Priced To Sell Fast! Renovate & Resell or Buy & Hold, Desirable 2 Level Colonial, Spacious Kitchen, Spacious Bedrooms, Covered Front Porch, Much More!! Just Waiting For Your Personal Cosmetics and Renovations to Make it Shine. Close to Schools, Shopping and Commuter Routes. This Will Not Last! Sol CHESTERTOWN, MD Living Area: 910 Sqft.	2 Beds, 1 Bath	$62,400
234 N COLLEGE AVENUE Investor Special – Charming Colonial in Prime Chestertown Location! Welcome to 234 N College Ave, an adorable colonial full of character and potential, nestled in the heart of historic Chestertown. This short sale opportunity is a rare find for savvy investors or buyers ready to bring their visio CHESTERTOWN, MD Living Area: 1296 Sqft.	2 Beds, 1 Bath	$164,000
624 HIGH STREET Step into the charm of historic Chestertown with this 2BR/1BA home full of potential. Featuring a screened front porch, spacious layout, and rear alley access, this property is perfect for investors or visionary buyers. Located just blocks from Washington College, the Chester River, downtown shop CHESTERTOWN, MD Living Area: 1290 Sqft.	2 Beds, 1 Bath	$240,000

Maryland, United States

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Homes for sale near Chestertown Stabilization Pond Number 1, Kent County, MD, USA