Homes for Sale in Chestertown, MD

price
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42-82 of 92 Homes
Active
front view of a house with a yard
1/24
New Construction

$765,900

3
Bedrooms
1,964
Square Feet

37 Landing Lane, Chestertown, MD 21620

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a front view of house with yard
1/24
New Construction

$799,900

3
Bedrooms
2,092
Square Feet
Unavailable
Acres

106 Landing Lane, Chestertown, MD 21620

a front view of a house with a yard
1/24
New Construction

$813,900

3
Bedrooms
2,192
Square Feet
Unavailable
Acres

104 Landing Lane, Chestertown, MD 21620

a front view of a house
1/26
New Construction

$786,900

3
Bedrooms
1,964
Square Feet

35 Landing Lane, Chestertown, MD 21620

$753,500 | 36 Landing Lane, Chestertown, MD 21620
1/26
New Construction

$753,500

3
Bedrooms
1,964
Square Feet

36 Landing Lane, Chestertown, MD 21620

a front view of a house
1/23
New Construction

$839,500

3
Bedrooms
1,964
Square Feet

102 Little Harbor Way, Chestertown, MD 21620

$865,000 | 106 South Queen Street, Chestertown, MD 21620
1/92

$865,000

3
Bedrooms
2,472
Square Feet
0.14
Acres

106 South Queen Street, Chestertown, MD 21620

a front view of a house with a yard
1/23
New Construction

$849,900

3
Bedrooms
1,980
Square Feet

104 Little Harbor Way, Chestertown, MD 21620

a front view of a residential apartment building with a yard
1/73

$1,600,000

7
Bedrooms
5,400
Square Feet

117 North Water Street, Unit 1A 1B 2A & 2B, Chestertown, MD 21620

$1,395,000 | 8276 Broad Neck Road, Chestertown, MD 21620
1/82

$1,395,000

4
Bedrooms
3,383
Square Feet
19.81
Acres

8276 Broad Neck Road, Chestertown, MD 21620

$1,800,000 | Little Harbor Way, Unit 1, Chestertown, MD 21620
1/29
Virtual TourNew Construction

$1,800,000

4
Bedrooms
3,540
Square Feet

Little Harbor Way, Unit 1, Chestertown, MD 21620

a front view of a house with a porch
1/22
New Construction

$1,099,900

4
Bedrooms
2,784
Square Feet

25 Landing Lane, Chestertown, MD 21620

$2,200,000 | 7989 Quaker Neck Road, Chestertown, MD 21620
1/60
Open: 7/4 11:00AM - 01:00PM

$2,200,000

5
Bedrooms
4,305
Square Feet
0.84
Acres

7989 Quaker Neck Road, Chestertown, MD 21620

a view of a back yard of the house
1/13

$750,000

Unavailable
Bedrooms
2,045
Square Feet
0.10
Acres

201 North Lynchburg Street, Chestertown, MD 21620

an aerial view of a house
1/3

$55,000

Unavailable
Bedrooms
Unavailable
Bathrooms
Unavailable
Square Feet
0.70
Acres

36 Parcel 80 Watertower Road, Chestertown, MD 21620

$1,245,500 | 105 High Street, Chestertown, MD 21620
1/48
Open: 7/11 10:00AM - 12:00PMVirtual Tour

$1,245,500

5
Bedrooms
3,243
Square Feet
0.06
Acres

105 High Street, Chestertown, MD 21620

$299,000 | 208 Central Drive, Chestertown, MD 21620
1/16

$299,000

3
Bedrooms
1,120
Square Feet
0.55
Acres

208 Central Drive, Chestertown, MD 21620

$320,000 | 222 Dutchess Road, Chestertown, MD 21620
1/25

$320,000

3
Bedrooms
1,096
Square Feet
0.67
Acres

222 Dutchess Road, Chestertown, MD 21620

$59,999 | 228 Merganser Drive, Chestertown, MD 21620
1/13

$59,999

Unavailable
Bedrooms
Unavailable
Bathrooms
Unavailable
Square Feet
0.51
Acres

228 Merganser Drive, Chestertown, MD 21620

$519,900 | 101 Coleman Drive, Chestertown, MD 21620
1/56

$519,900

3
Bedrooms
2,268
Square Feet
1.1
Acres

101 Coleman Drive, Chestertown, MD 21620

$565,000 | 204 Double Creek Road, Chestertown, MD 21620
1/46

$565,000

3
Bedrooms
2,927
Square Feet
0.87
Acres

204 Double Creek Road, Chestertown, MD 21620

$135,000 | 109 2nd Street, Chestertown, MD 21620

$135,000

Unavailable
Bedrooms
Unavailable
Bathrooms
Unavailable
Square Feet
1.8
Acres

109 2nd Street, Chestertown, MD 21620

$6,000 | 23683 L Road, Chestertown, MD 21620
1/4

$6,000

Unavailable
Bedrooms
Unavailable
Bathrooms
Unavailable
Square Feet
0.69
Acres

23683 L Road, Chestertown, MD 21620

$59,000 | Sandy Bottom Road, Chestertown, MD 21620
1/6

$59,000

Unavailable
Bedrooms
Unavailable
Bathrooms
Unavailable
Square Feet
1.95
Acres

Sandy Bottom Road, Chestertown, MD 21620

a view of swimming pool with outdoor space
1/23

$200,000

Unavailable
Bedrooms
Unavailable
Bathrooms
Unavailable
Square Feet
5.81
Acres

0 Round Top Road, Chestertown, MD 21620

an aerial view of residential house with outdoor space and swimming pool
1/9

$109,999

Unavailable
Bedrooms
Unavailable
Bathrooms
Unavailable
Square Feet
0.18
Acres

116 South Cross Street, Chestertown, MD 21620

$25,000 | Johnsontown Road, Chestertown, MD 21620
1/14

$25,000

Unavailable
Bedrooms
Unavailable
Bathrooms
Unavailable
Square Feet
0.9
Acres

Johnsontown Road, Chestertown, MD 21620

a view of a lake with houses
1/5

$635,000

Unavailable
Bedrooms
Unavailable
Bathrooms
Unavailable
Square Feet
0.09
Acres

108 Little Harbor Way, Chestertown, MD 21620

a backyard of a house with lots of green space
1/3

$750,000

Unavailable
Bedrooms
Unavailable
Bathrooms
Unavailable
Square Feet
0.10
Acres

201 North Lynchburg Street, Chestertown, MD 21620

$225,000 | Haacke Drive, Chestertown, MD 21620
1/7

$225,000

Unavailable
Bedrooms
Unavailable
Bathrooms
Unavailable
Square Feet
0.87
Acres

Haacke Drive, Chestertown, MD 21620

$250,000 | Scheeler Road, Chestertown, MD 21620
1/4

$250,000

Unavailable
Bedrooms
Unavailable
Bathrooms
Unavailable
Square Feet
0.85
Acres

Scheeler Road, Chestertown, MD 21620

$3,000 | Cogar Road, Chestertown, MD 21620
1/3

$3,000

Unavailable
Bedrooms
Unavailable
Bathrooms
Unavailable
Square Feet
0.34
Acres

Cogar Road, Chestertown, MD 21620

a green yard with lots of trees
1/8

$150,000

Unavailable
Bedrooms
Unavailable
Bathrooms
Unavailable
Square Feet
2
Acres

Caulks Field Road, Chestertown, MD 21620

$3,000 | Lenapah Road, Chestertown, MD 21620
1/3

$3,000

Unavailable
Bedrooms
Unavailable
Bathrooms
Unavailable
Square Feet
0.34
Acres

Lenapah Road, Chestertown, MD 21620

$38,000 | Spinnaker Road, Chestertown, MD 21620
1/2

$38,000

Unavailable
Bedrooms
Unavailable
Bathrooms
Unavailable
Square Feet
0.56
Acres

Spinnaker Road, Chestertown, MD 21620

$37,000 | Fish Hatchery Road, Chestertown, MD 21620
1/2

$37,000

Unavailable
Bedrooms
Unavailable
Bathrooms
Unavailable
Square Feet
0.34
Acres

Fish Hatchery Road, Chestertown, MD 21620

$24,000 | 23710 L Road, Chestertown, MD 21620
1/2

$24,000

Unavailable
Bedrooms
Unavailable
Bathrooms
Unavailable
Square Feet
0.5
Acres

23710 L Road, Chestertown, MD 21620

$38,000 | Redfield Road, Chestertown, MD 21620
1/2

$38,000

Unavailable
Bedrooms
Unavailable
Bathrooms
Unavailable
Square Feet
0.34
Acres

Redfield Road, Chestertown, MD 21620

$40,000 | Montgomery Avenue, Chestertown, MD 21620
1/2

$40,000

Unavailable
Bedrooms
Unavailable
Bathrooms
Unavailable
Square Feet
0.11
Acres

Montgomery Avenue, Chestertown, MD 21620

an aerial view of a house

$9,500

Unavailable
Bedrooms
Unavailable
Bathrooms
Unavailable
Square Feet
0.34
Acres

Quaker Neck Landing Road, Chestertown, MD 21620

$8,000 | Parcel Buck Neck Road, Chestertown, MD 21620
1/6

$8,000

Unavailable
Bedrooms
Unavailable
Bathrooms
Unavailable
Square Feet
0.34
Acres

Parcel Buck Neck Road, Chestertown, MD 21620

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