Homes for Sale in Chestertown, MD

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1-41 of 98 Homes
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$499,999 | 218 Camelot, Chestertown, MD 21620
1/44
Listed By Coldwell Banker Realty

$499,999

5
Bedrooms
3,932
Square Feet
0.24
Acres

218 Camelot, Chestertown, MD 21620

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$279,900 | 22481 Goose Hollow Drive, Chestertown, MD 21620
1/88

$279,900

3
Bedrooms
1,296
Square Feet
2
Acres

22481 Goose Hollow Drive, Chestertown, MD 21620

$468,000 | 25750 Collins Avenue, Chestertown, MD 21620
1/50

$468,000

3
Bedrooms
3,262
Square Feet
0.76
Acres

25750 Collins Avenue, Chestertown, MD 21620

$475,000 | 105 North Water Street, Unit 2, Chestertown, MD 21620
1/49
Virtual Tour

$475,000

2
Bedrooms
1,011
Square Feet

105 North Water Street, Unit 2, Chestertown, MD 21620

$615,000 | 103 Maple Avenue, Chestertown, MD 21620
1/13
New

$615,000

4
Bedrooms
4,536
Square Feet
0.27
Acres

103 Maple Avenue, Chestertown, MD 21620

$515,000 | 101 South Mill Street, Chestertown, MD 21620
1/39

$515,000

2
Bedrooms
1,476
Square Feet
0.08
Acres

101 South Mill Street, Chestertown, MD 21620

$247,000 | 104 Conley Drive, Chestertown, MD 21620
1/27

$247,000

3
Bedrooms
1,280
Square Feet
0.07
Acres

104 Conley Drive, Chestertown, MD 21620

$324,900 | 517 Round Top Road, Chestertown, MD 21620
1/28

$324,900

3
Bedrooms
1,248
Square Feet
0.34
Acres

517 Round Top Road, Chestertown, MD 21620

$284,900 | 104 Acorn Drive, Chestertown, MD 21620
1/26

$284,900

3
Bedrooms
1,900
Square Feet
0.05
Acres

104 Acorn Drive, Chestertown, MD 21620

$100,000 | 234 North College Avenue, Chestertown, MD 21620
1/3

$100,000

2
Bedrooms
1,296
Square Feet
0.09
Acres

234 North College Avenue, Chestertown, MD 21620

$1,200,000 | 202 Royston Shores Road, Chestertown, MD 21620
1/72

$1,200,000

4
Bedrooms
2,292
Square Feet
0.61
Acres

202 Royston Shores Road, Chestertown, MD 21620

$99,900 | 110 Prospect Street, Chestertown, MD 21620
1/6

$99,900

3
Bedrooms
2,210
Square Feet
0.08
Acres

110 Prospect Street, Chestertown, MD 21620

$1,650,000 | 8796 Maryland Parkway, Chestertown, MD 21620
1/60
Virtual Tour

$1,650,000

9
Bedrooms
4,776
Square Feet
9.2
Acres

8796 Maryland Parkway, Chestertown, MD 21620

$380,000 | 213 Byford Drive, Chestertown, MD 21620
1/39

$380,000

4
Bedrooms
1,277
Square Feet
0.34
Acres

213 Byford Drive, Chestertown, MD 21620

$75,000 | Fairlee Road, Chestertown, MD 21620
1/7

$75,000

Unavailable
Bedrooms
Unavailable
Bathrooms
Unavailable
Square Feet
2.2
Acres

Fairlee Road, Chestertown, MD 21620

$200,000 | 21172 Wyoming Avenue, Chestertown, MD 21620

$200,000

4
Bedrooms
2,920
Square Feet
0.28
Acres

21172 Wyoming Avenue, Chestertown, MD 21620

$429,900 | 10781 Fermoy Road, Chestertown, MD 21620
1/54

$429,900

4
Bedrooms
2,160
Square Feet
0.39
Acres

10781 Fermoy Road, Chestertown, MD 21620

a green field with lots of trees
1/11

$265,000

3
Bedrooms
1,967
Square Feet
2.64
Acres

1904 Pondtown Road, Chestertown, MD 21620

$1,450,000 | 22470 Fairgale Farm Lane, Chestertown, MD 21620
1/49

$1,450,000

4
Bedrooms
4,257
Square Feet
3.55
Acres

22470 Fairgale Farm Lane, Chestertown, MD 21620

$425,000 | 522 High Street, Chestertown, MD 21620
1/15

$425,000

2
Bedrooms
1,518
Square Feet
0.08
Acres

522 High Street, Chestertown, MD 21620

$110,000 | 1906 Pondtown Road, Chestertown, MD 21620
1/4

$110,000

Unavailable
Bedrooms
Unavailable
Bathrooms
Unavailable
Square Feet
1.93
Acres

1906 Pondtown Road, Chestertown, MD 21620

$285,000 | 956 Washington Avenue, Chestertown, MD 21620
1/29

$285,000

3
Bedrooms
1,248
Square Feet
0.69
Acres

956 Washington Avenue, Chestertown, MD 21620

a backyard of a house with table and chairs
1/3

$80,000

Unavailable
Bedrooms
Unavailable
Bathrooms
Unavailable
Square Feet
4.03
Acres

8886 Georgetown Road, Chestertown, MD 21620

$329,900 | 102 Flying Cloud Drive, Chestertown, MD 21620
1/41

$329,900

3
Bedrooms
1,896
Square Feet
0.09
Acres

102 Flying Cloud Drive, Chestertown, MD 21620

$385,000 | 107 Flying Cloud Drive, Chestertown, MD 21620
1/51

$385,000

5
Bedrooms
2,534
Square Feet
0.11
Acres

107 Flying Cloud Drive, Chestertown, MD 21620

$309,900 | 304 Hadaway Drive, Chestertown, MD 21620
1/38
Virtual Tour

$309,900

4
Bedrooms
1,325
Square Feet
0.41
Acres

304 Hadaway Drive, Chestertown, MD 21620

$340,000 | 214 Silver Heel Road, Chestertown, MD 21620
1/26

$340,000

4
Bedrooms
1,972
Square Feet
0.10
Acres

214 Silver Heel Road, Chestertown, MD 21620

a front view of a house with a garden
1/65

$399,900

3
Bedrooms
1,944
Square Feet
0.23
Acres

103 Trafford Drive, Chestertown, MD 21620

$15,000 | 23741 L Road, Chestertown, MD 21620
1/2

$15,000

Unavailable
Bedrooms
Unavailable
Bathrooms
Unavailable
Square Feet
1
Acres

23741 L Road, Chestertown, MD 21620

a house with trees in the background
1/51

$389,000

3
Bedrooms
1,120
Square Feet
0.51
Acres

240 Merganser Drive, Chestertown, MD 21620

$198,000 | 139 Prospect Street, Chestertown, MD 21620
1/28

$198,000

3
Bedrooms
1,200
Square Feet
0.15
Acres

139 Prospect Street, Chestertown, MD 21620

$259,900 | 103 Metcalf Road, Chestertown, MD 21620
1/22
Open: 6/30 02:00PM - 06:00PMNew Construction

$259,900

3
Bedrooms
1,280
Square Feet
0.13
Acres

103 Metcalf Road, Chestertown, MD 21620

a view of entryway and hall
1/23

$350,000

1
Bedrooms
850
Square Feet

117 North Water Street, Unit 2B, Chestertown, MD 21620

a front view of a house with a garden
1/20

$244,500

2
Bedrooms
912
Square Feet
0.37
Acres

21217 Texas Avenue, Chestertown, MD 21620

a front view of a house with a yard and trees
1/29

$429,999

4
Bedrooms
1,656
Square Feet
0.15
Acres

222 Mt Vernon Avenue, Chestertown, MD 21620

$450,000 | 110 Trafford Drive, Chestertown, MD 21620
1/22

$450,000

4
Bedrooms
2,880
Square Feet
0.28
Acres

110 Trafford Drive, Chestertown, MD 21620

an outdoor space with lots of furniture and garden
1/70

$499,999

2
Bedrooms
2,100
Square Feet
0.03
Acres

103 Landing Lane, Chestertown, MD 21620

$499,900 | 8620 Park Drive, Chestertown, MD 21620
1/66

$499,900

4
Bedrooms
2,524
Square Feet
1.37
Acres

8620 Park Drive, Chestertown, MD 21620

a living room with fireplace furniture and a window
1/24

$375,000

2
Bedrooms
787
Square Feet

117 North Water Street, Unit 2A, Chestertown, MD 21620

a front view of a house with a garden
1/7

$320,000

3
Bedrooms
1,232
Square Feet
0.33
Acres

8706 Elm Road, Chestertown, MD 21620

a front view of a house with a yard and trees
1/27

$385,000

4
Bedrooms
2,630
Square Feet
1.65
Acres

23043 Bay Shore Spur, Chestertown, MD 21620

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