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| Address | Bed / Bath | Listing Price |
|---|---|---|
204 ROLLING ROAD
Live with ease in this beautifully updated and maintained one floor home in downtown Chestertown. The current owners put a large addition on the house that includes a family room with wood burning stove, sunroom, and primary suite with en suite bathroom and walk in closet. A large laundry room on th
Living Area:
2296 Sqft.
|
3
Beds,
2
Baths
|
$370,000 |
112 SILVER HEEL DRIVE
AGENTS - PLEASE VIEW AGENT REMARKS IN BRIGHT MLS.
Welcome to this stunning 2023 built home — a move-in ready, three-story residence offering 5 bedrooms and 3.5 baths across 2,615 sq ft of thoughtfully designed space. The first floor features an open layout with a spacious family room, dining area
Living Area:
2615 Sqft.
|
5
Beds,
4
Baths
|
$250,000 |
304 HADAWAY DRIVE
Welcome to 304 Hadaway Dr. This classic home has been completely reimagined and is ready for it's next chapter. Entering the home you will immediately notice the beautifully refinished original hardwood floors. As you make your way down the hallway past the newly renovated hall bath with custom ti
Living Area:
1325 Sqft.
|
4
Beds,
2
Baths
|
$425,000 |
303 E CAMPUS AVENUE
Charming Brick Rancher in the Heart of Chestertown
Discover this classic brick rancher nestled in one of Chestertown’s established neighborhoods. Enjoy the convenience of being just a short walk or bike ride from downtown, where you’ll find favorite local shops, restaurants, and the beloved Sat
Living Area:
1532 Sqft.
|
3
Beds,
2
Baths
|
$363,000 |
318 LINCOLN
Kent County welcomes you with a move-in ready home that’s full of updates! This 3-bedroom, 2-bath home sits on nearly a half-acre and is just minutes from downtown Chestertown. Enjoy peace of mind with a newer roof (approximately 5 years old), central heat and air, and a tankless water heater. The
Living Area:
960 Sqft.
|
3
Beds,
2
Baths
|
$269,000 |
411 GREENWOOD AVENUE
Experience the best of in-town Chestertown living in this custom-built single-level home! The open floor plan features abundant natural light, gleaming hardwood floors and a bright, inviting layout perfect for entertaining or relaxing. The dining room is open to the kitchen which includes some updat
Living Area:
1676 Sqft.
|
3
Beds,
3
Baths
|
$419,000 |
107 MALONE AVENUE
Welcome to 107 Malone Ave. in the friendly community of Foxley Manor....A Great place to call "HOME"! This lovely 3 Bedroom, 1 Bath home is ready for you to make new memories, grow your family or downsize while enjoying single level living. Hardwood Floors throughout the living room and bedrooms ha
Living Area:
1200 Sqft.
|
3
Beds,
1
Bath
|
$290,000 |
206 VALLEY
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. Floor plan that flows beautifully. 4 bedrooms and 2 baths. Wood burning fire place in the living room. House is filled with natu
Living Area:
2869 Sqft.
|
4
Beds,
2
Baths
|
$615,000 |
100 ADELA WAY
*Days on Market Reporting Incorrectly- Property listed Oct 30, 2025*
Nestled just outside of historic Chestertown, minutes from farmers market, waterfront park and local shops and eateries. This home offers the best of small-town living with modern updates at every turn.
Step inside to discover woo
Living Area:
3799 Sqft.
|
4
Beds,
4
Baths
|
$515,000 |
116 HARLAN LOOP
$$THE OWNER MUST RELOCATE. TAKE ADVANTAGE OF THE NEW PRICE IMPROVEMENT! $$
Welcome to Coventry Farms in Chestertown — where comfort, elegance, and space come together in this stunning colonial-style home!
Built in 2009 and meticulously maintained, this spacious property offers over 4,000 square f
Living Area:
4067 Sqft.
|
5
Beds,
4
Baths
|
$519,000 |
103 ADELA WAY
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 further! 3 Floors of living space, 4 - possibly 5 Bedrooms, 3 Full & 1 -1/2 Baths. Enter in through this spacious well-lit foyer which
Living Area:
5576 Sqft.
|
4
Beds,
4
Baths
|
$595,000 |
907 N MEADOWVIEW DRIVE
JUST INSTALLED BRAND NEW CARPET!
Welcome to 907 N Meadowview Drive, a beautifully maintained home in the sought-after Crestview community of Chestertown. Situated on a spacious .707-acre lot, this 3-bedroom, 2.5-bath home offers 1,842 square feet of comfortable living space.
Step inside to find a
Living Area:
1842 Sqft.
|
3
Beds,
3
Baths
|
$410,000 |
251 DEVON DRIVE
Welcome to 251 Devon Drive located in the desirable Coventry Farms neighborhood. When entering the paved circular driveway, you will find the property meticulously landscaped. The inviting curb appeal welcomes you into the home's foyer where you will find a living room to the left and formal dini
Living Area:
3935 Sqft.
|
3
Beds,
3
Baths
|
$595,000 |