Chestertown Homes for Sale

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Single Family

910 WASHINGTON AVENUE, CHESTERTOWN, Maryland 21620

4Bedroom(s)
2Bathroom(s)
6Parking(s)
25Picture(s)
1,806Sqft
Take advantage of this spacious Cape Cod that can be residential and/or commercial with 4 bedrooms and/or offices and 2 full baths, hardwood floors throughout the main level, brick fireplace, freshly painted and large backyard. Prime location right on 213 and close to all Chestertown offers; Washington College, restaurants, hospital, local shops, new marina and much more.
$199,000

Single Family

108 CANNON STREET, CHESTERTOWN, Maryland 21620

3Bedroom(s)
4Bathroom(s)
2Parking(s)
25Picture(s)
3,429Sqft
New Listing ~ The Cuff House ~ an impeccably restored historic home with modern amenities and substantial upgrades located on Cannon Street in Chestertown with water views from the front porch and a short distance to downtown.
$850,000

Single Family

103 CANNON STREET, CHESTERTOWN, Maryland 21620

4Bedroom(s)
4Bathroom(s)
25Picture(s)
2,642Sqft
Gorgeous Victorian replica, 1995 build in the Historic District. BRAND NEW windows and siding; refinished mahogany hardwood flooring; elevator access from the basement to the 2nd floor; 3rd floor artists studio; spa room for ultimate relaxation; off street parking lot; only 1 block from the new marina and all that Downtown Chestertown has to offer.
$459,900

Single Family

200 COURT STREET, CHESTERTOWN, Maryland 21620

10Picture(s)
1,503Sqft
Great opportunity for someone wanting professional office space or would like to convert into a residence! RB professional zoning permits both! Was used as a law office for many years and would be ideal for the lawyer who is ready to branch out on their own. Recently has had mold remediation, documentation is available.
$329,900

Single Family

616 HIGH STREET, CHESTERTOWN, Maryland 21620

2Bedroom(s)
2Bathroom(s)
25Picture(s)
1,005Sqft
Completely renovated with central air/heat, original wood floors, 2 full baths & tile backsplash in the kitchen! The 3rd room upstairs could be used for an office, nursery or make it into a large closet for that extra storage! Large living and dining rooms are great for entertaining with a bonus storage area.
$165,900

Single Family

535 HIGH STREET, CHESTERTOWN, Maryland 21620

2Bedroom(s)
3Bathroom(s)
25Picture(s)
1,608Sqft
Unique and charming home within walking distance of downtown Chestertown and the river! Lovingly restored in 2013, the home features hardwood floors throughout, fresh paint in many rooms, a spacious screened porch and two master suites. The second floor features a spacious bedroom with a walk-in closet, a separate dressing room & laundry area next to the full bath with double vanity.
$319,000

Single Family

102 CANNON STREET, CHESTERTOWN, Maryland 21620

3Bedroom(s)
3Bathroom(s)
25Picture(s)
2,028Sqft
Impeccably maintained charming home with a water view of the Chester River. First floor open floor plan is perfect for entertaining. Living room with fireplace flows into a gourmet kitchen and right into the dinning area. Beautifully restored staircase takes you to a landing with bookcases and three bedrooms with two baths.
$995,000

Single Family

107 S QUEEN STREET, CHESTERTOWN, Maryland 21620

4Bedroom(s)
2Bathroom(s)
3Parking(s)
25Picture(s)
2,530Sqft
Location, Location, Location! Historic downtown home situated literally in the heart of everything Chestertown has to offer....
$349,000

Single Family

202 N QUEEN ST, CHESTERTOWN, Maryland 21620

5Bedroom(s)
3Bathroom(s)
25Picture(s)
0.12Acre
Gorgeous Victorian Two-Unit Home in Need of a Facelift. She's a Beauty Located in a Beautiful Historic Waterfront Town! Pretty Street, Nice Front and Rear Yards, Rear Shed. Inside Has Fantastic Heart of Pine Flooring, Spacious Rooms and a Great Floor Plan.
$250,000

Single Family

PARK DRIVE, CHESTERTOWN, Maryland 21620

3Bedroom(s)
2Bathroom(s)
2Parking(s)
25Picture(s)
2,000Sqft
TO BE BUILT - List price reflects the lot & lot development with the Haydn model. There are many other floor plans and upgrades available with Caruso Homes, however there is no builder tie-in. All on two parcels totaling approximately 1.81 Acres on a quiet street among well-kept homes and manicured lawns.
$439,000

Single Family

8861 GEORGETOWN ROAD, CHESTERTOWN, Maryland 21620

3Bedroom(s)
1Bathroom(s)
3Picture(s)
1,292Sqft
Small bungalow, quiet street, public utilities, priced to sell.
$69,000

Residential

10252 FAIRLEE RD, CHESTERTOWN, Maryland 21620

2Bedroom(s)
1Bathroom(s)
2Picture(s)
2Acre
This property does not have a regular septic tank. You can do holding tanks and there is grant money available to help pay for that. There is a well . If you would like to talk to the Health Department please call John Bescuit at (410) 778-1350.
$70,000
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