Chestertown Homes for Sale

Sort Option
  • _score
  • Price ↓
  • Newest Listings First
  • Square Footage ↓
  • Year Built ↓
Grid
List
Map

Residential

24095 CHESTERTOWN ROAD, CHESTERTOWN, Maryland 21620

3Bedroom(s)
1Bathroom(s)
1Parking(s)
10Picture(s)
1,104Sqft
Cute rancher located a few miles outside of Chestertown. New carpet and new paint!!! Great living space. Kitchen has all of the major appliances. Laundry is located in the bath for easy access. Great backyard that overlooks farm fields. There is a one car detached garage. Could be used as a rental and has received a lead free certification.
$175,000

Single Family

705 HIGH STREET, CHESTERTOWN, Maryland 21620

2Bedroom(s)
1Bathroom(s)
9Picture(s)
640Sqft
This could be the perfect investment for you!!! Fix it up and make it your own! Just a few blocks to downtown and the waterfront area! FANTASTIC PRICE!
$37,500

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.
$340,000

Residential

332 QUEEN STREET, CHESTERTOWN, Maryland 21620

4Bedroom(s)
2Bathroom(s)
10Picture(s)
2,060Sqft
Circa 1870 home with Chester River views situated on an acre-plus just blocks from downtown Chestertown and Washington College. Enjoy the private, park-like setting of this hilltop property located in a quiet riverfront neighborhood.
$399,900

Single Family

531 CANNON STREET, CHESTERTOWN, Maryland 21620

2Bedroom(s)
2Bathroom(s)
10Picture(s)
1,190Sqft
This in town location is perfect - walk to shops and restaurants and enjoy all the activities that Chestertown has to offer. The home is in good condition with new carpet on the first floor. Updated kitchen as well.
$159,000

Single Family

8634 CAULKS FIELD ROAD, CHESTERTOWN, Maryland 21620

3Bedroom(s)
1Bathroom(s)
10Picture(s)
1,128Sqft
Near Rock Hall, MD. Great 3 bedroom, bath Ranch home on 1.66 acres in Chestertown, MD. This home is a great starter home or for downsizing. It has a large living room and dining room off the kitchen. Hardwood floors. The yard is flat with open space that backs to woods. The front of the house faces farm fields. If you are looking for peace and quiet you will find it here.
$92,000

Single Family

103 CANNON STREET, CHESTERTOWN, Maryland 21620

4Bedroom(s)
4Bathroom(s)
10Picture(s)
2,642Sqft
Gorgeous Victorian replica, 1995 build in the Historic District. Seller is offering a $4,000 appliance credit! 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.
$475,000

Residential

602 CANNON STREET, CHESTERTOWN, Maryland 21620

2Bedroom(s)
2Bathroom(s)
10Picture(s)
0.20Acre
Bring your plans & start building! The footprint is solid, the water & sewer lines are BRAND NEW, the electric supply and breaker box are BRAND NEW, and the lot is HUGE with tons of potential! All within walking distance to everything Downtown Chestertown has to offer... shops, restaurants, parks & the new marina.
$79,000

Single Family

519 HIGH STREET, CHESTERTOWN, Maryland 21620

6Bedroom(s)
3Bathroom(s)
10Picture(s)
2,076Sqft
Investment opportunity! Multi unit in Downtown Chestertown offers 3 units, 1st floor (largest) is a 3 bedroom 1 bath, washer/dryer & has rented for $950/month, 2nd floor is a 2 bedroom 1 bath and has rented for $850 but currently empty & 3rd floor (attic) is a studio (needs work) but can be rented at $450/month.
$179,500

Residential

112 S KENT STREET, CHESTERTOWN, Maryland 21620

3Bedroom(s)
3Bathroom(s)
10Picture(s)
1,524Sqft
Meticulously renovated with stunning details. One of Chestertown~s finest historic renovations. Professionally designed features preserving its original historic charm. A perfect example of what careful planning and style achieves. Close distance to the river, bakery, local coffee shop, waterfront dining, Washington College and the soon to be completed Chestertown Marina.
$345,000

Single Family

100 S KENT ST, CHESTERTOWN, Maryland 21620

3Bedroom(s)
1Bathroom(s)
9Picture(s)
0.02Acre
Enjoy living in Historic Chestertown, short distance to downtown, shopping, and restaurants and the Chester River. Well maintained 3 BR, 1 BA home, enclosed front porch with heat. Nice cozy home for first time homebuyers or investors.
$229,500

Single Family

204 N WATER STREET, CHESTERTOWN, Maryland 21620

3Bedroom(s)
3Bathroom(s)
10Picture(s)
2,135Sqft
204 NORTH WATER is the perfect marriage between early 20th century and 21st century. The era in which it was built featured many gracious details all retained and meticulously restored. One is struck by the inviting front porch, the Victorian details of ballustrades, true working shutters, metal roof and Wisteria mounted along porch eaves. So typical of the time.
$529,000
82 Results returned.Per Page
Do NOT follow this link or you will be banned from the site!