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Chestertown, MD Real Estate & Homes For Sale

169 properties

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308 Park Row, Chestertown, MD 21620 View this property at 308 Park Row, Chestertown, MD 21620
308 Park Row Chestertown MD 21620
Just Listed
308 Park Row 
Chestertown, MD 21620
$140,000
  • Duplex
  • Active
  • MLS # KE10065862
  • Updated 16 hours ago
  • 2
    Beds
  • 1
    Full Bath
  • 1
    Partial Bath
  • 2
    Total Baths

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208 Queen Street South, Chestertown, MD 21620 View this property at 208 Queen Street South, Chestertown, MD 21620
208 Queen Street South Chestertown MD 21620
Just Listed

1/16

208 Queen Street South 
Chestertown, MD 21620
$340,000
  • Single Family
  • Active
  • MLS # KE10064553
  • Updated 3 days ago
  • 2
    Beds
  • 2
    Full Baths
  • 1
    Partial Bath
  • 3
    Total Baths
  • 1,640
    Sq. Ft.

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112 Devon Drive, Chestertown, MD 21620 View this property at 112 Devon Drive, Chestertown, MD 21620
112 Devon Drive Chestertown MD 21620

1/29

112 Devon Drive 
Chestertown, MD 21620
$314,900
  • Single Family
  • Active
  • MLS # KE10060246
  • Updated 3 days ago
  • 4
    Beds
  • 3
    Full Baths
  • 1
    Partial Bath
  • 4
    Total Baths
  • 2,564
    Sq. Ft.
  • 2
    Car Garage

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157 Longfellow Drive, Chestertown, MD 21620 View this property at 157 Longfellow Drive, Chestertown, MD 21620
157 Longfellow Drive Chestertown MD 21620

1/27

157 Longfellow Drive 
Chestertown, MD 21620
$179,900
Est. Rent: $1,420/mo
  • Single Family
  • Active
  • MLS # QA10060319
  • Updated 3 days ago
  • 3
    Beds
  • 2
    Full Baths
  • 2
    Total Baths
  • 1
    Car Garage

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26712 Morgnec Road, Chestertown, MD 21620 View this property at 26712 Morgnec Road, Chestertown, MD 21620
26712 Morgnec Road Chestertown MD 21620

1/18

26712 Morgnec Road 
Chestertown, MD 21620
$125,000
  • Single Family
  • Active
  • MLS # KE10060332
  • Updated 7 days ago
  • 2
    Beds
  • 1
    Full Bath
  • 1
    Total Bath

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8721 Orchard Drive, Chestertown, MD 21620 View this property at 8721 Orchard Drive, Chestertown, MD 21620
8721 Orchard Drive Chestertown MD 21620
Sale Pending
8721 Orchard Drive 
Chestertown, MD 21620
$425,000
  • Single Family
  • Pending
  • MLS # KE10057960
  • Updated 10 days ago
  • 5
    Beds
  • 3
    Full Baths
  • 3
    Total Baths
  • 2
    Car Garage

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108 School Road, Chestertown, MD 21620 View this property at 108 School Road, Chestertown, MD 21620
108 School Road Chestertown MD 21620

1/29

108 School Road 
Chestertown, MD 21620
$195,900
  • Single Family
  • Active
  • MLS # KE10058302
  • Updated 1 hour ago
  • 4
    Beds
  • 2
    Full Baths
  • 2
    Total Baths

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406 River Road, Chestertown, MD 21620 View this property at 406 River Road, Chestertown, MD 21620
406 River Road Chestertown MD 21620

1/26

406 River Road 
Chestertown, MD 21620
$1,250,000
  • Single Family
  • Active
  • MLS # QA10056028
  • Updated 12 days ago
  • 4
    Beds
  • 3
    Full Baths
  • 1
    Partial Bath
  • 4
    Total Baths
  • 2
    Car Garage

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6854 Pentridge Court, Chestertown, MD 21620 View this property at 6854 Pentridge Court, Chestertown, MD 21620
6854 Pentridge Court Chestertown MD 21620

1/29

6854 Pentridge Court 
Chestertown, MD 21620
$1,250,000
  • Single Family
  • Active
  • MLS # KE10055129
  • Updated 9 days ago
  • 4
    Beds
  • 3
    Full Baths
  • 1
    Partial Bath
  • 4
    Total Baths
  • 2,940
    Sq. Ft.
  • 3
    Car Garage

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311 South Queen Street, Chestertown, MD 21620 View this property at 311 South Queen Street, Chestertown, MD 21620
311 South Queen Street Chestertown MD 21620

1/24

311 South Queen Street 
Chestertown, MD 21620
$297,000
  • Townhouse
  • Active
  • MLS # KE10055156
  • Updated 2 days ago
  • 3
    Beds
  • 3
    Full Baths
  • 1
    Partial Bath
  • 4
    Total Baths

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9011 Georgetown Road, Chestertown, MD 21620 View this property at 9011 Georgetown Road, Chestertown, MD 21620
9011 Georgetown Road Chestertown MD 21620

1/3

9011 Georgetown Road 
Chestertown, MD 21620
$24,900
  • Single Family
  • Active
  • MLS # KE10052205
  • 3
    Beds
  • 1
    Full Bath
  • 1
    Total Bath

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223 Devon Drive, Chestertown, MD 21620 View this property at 223 Devon Drive, Chestertown, MD 21620
223 Devon Drive Chestertown MD 21620

1/30

223 Devon Drive 
Chestertown, MD 21620
$262,500
  • Single Family
  • Active
  • MLS # KE10050197
  • 4
    Beds
  • 2
    Full Baths
  • 1
    Partial Bath
  • 3
    Total Baths
  • 2,186
    Sq. Ft.
  • 2
    Car Garage

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115 Conley Drive, Chestertown, MD 21620 View this property at 115 Conley Drive, Chestertown, MD 21620
115 Conley Drive Chestertown MD 21620

1/23

115 Conley Drive 
Chestertown, MD 21620
$124,000
  • Duplex
  • Active
  • MLS # KE10050834
  • 3
    Beds
  • 1
    Full Bath
  • 1
    Partial Bath
  • 2
    Total Baths
  • 1,320
    Sq. Ft.

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21244 Iowa Avenue, Chestertown, MD 21620 View this property at 21244 Iowa Avenue, Chestertown, MD 21620
21244 Iowa Avenue Chestertown MD 21620

1/16

21244 Iowa Avenue 
Chestertown, MD 21620
$83,500
  • Single Family
  • Active
  • MLS # KE10050681
  • 4
    Beds
  • 2
    Full Baths
  • 2
    Total Baths

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105 College Avenue, Chestertown, MD 21620 View this property at 105 College Avenue, Chestertown, MD 21620
105 College Avenue Chestertown MD 21620

1/11

105 College Avenue 
Chestertown, MD 21620
$120,000
  • Multi-Family
  • Active
  • MLS # KE10043146

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105 Trafford Drive, Chestertown, MD 21620 View this property at 105 Trafford Drive, Chestertown, MD 21620
105 Trafford Drive Chestertown MD 21620
Price Reduced

1/23

105 Trafford Drive 
Chestertown, MD 21620
$264,970
-$5 (0%)
  • Single Family
  • Active
  • MLS # KE10041414
  • Updated 6 days ago
  • 4
    Beds
  • 2
    Full Baths
  • 2
    Partial Baths
  • 4
    Total Baths
  • 2,208
    Sq. Ft.
  • 2
    Car Garage

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610 High Street, Chestertown, MD 21620 View this property at 610 High Street, Chestertown, MD 21620
610 High Street Chestertown MD 21620

1/1

610 High Street 
Chestertown, MD 21620
$129,900
  • Single Family
  • Active
  • MLS # KE10041501
  • 3
    Beds
  • 1
    Full Bath
  • 1
    Total Bath

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436 Pear Tree Point Road, Chestertown, MD 21620 View this property at 436 Pear Tree Point Road, Chestertown, MD 21620
436 Pear Tree Point Road Chestertown MD 21620

1/17

436 Pear Tree Point Road 
Chestertown, MD 21620
$499,900
  • Single Family
  • Active
  • MLS # QA10041173
  • 4
    Beds
  • 3
    Full Baths
  • 3
    Total Baths
  • 2,887
    Sq. Ft.

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109 Lyons Lane, Chestertown, MD 21620 View this property at 109 Lyons Lane, Chestertown, MD 21620
109 Lyons Lane Chestertown MD 21620

1/29

109 Lyons Lane 
Chestertown, MD 21620
$425,000
Est. Rent: $2,760/mo
  • Single Family
  • Active
  • MLS # QA10040691
  • 3
    Beds
  • 2
    Full Baths
  • 1
    Partial Bath
  • 3
    Total Baths
  • 2
    Car Garage

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207 Longfellow Drive, Chestertown, MD 21620 View this property at 207 Longfellow Drive, Chestertown, MD 21620
207 Longfellow Drive Chestertown MD 21620

1/29

207 Longfellow Drive 
Chestertown, MD 21620
$155,555
  • Single Family
  • Active
  • MLS # QA10040169
  • 4
    Beds
  • 2
    Full Baths
  • 2
    Total Baths

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10202 John Carvill Road, Chestertown, MD 21620 View this property at 10202 John Carvill Road, Chestertown, MD 21620
10202 John Carvill Road Chestertown MD 21620

1/20

10202 John Carvill Road 
Chestertown, MD 21620
$339,000
  • Single Family
  • Active
  • MLS # KE10038872
  • Updated 5 days ago
  • 3
    Beds
  • 2
    Full Baths
  • 1
    Partial Bath
  • 3
    Total Baths
  • 3
    Car Garage

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9035 Queen Anne Street, Chestertown, MD 21620 View this property at 9035 Queen Anne Street, Chestertown, MD 21620
9035 Queen Anne Street Chestertown MD 21620

1/13

9035 Queen Anne Street 
Chestertown, MD 21620
$184,200
  • Single Family
  • Active
  • MLS # KE10037765
  • 3
    Beds
  • 1
    Full Bath
  • 1
    Partial Bath
  • 2
    Total Baths

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866 Washington Avenue, Chestertown, MD 21620 View this property at 866 Washington Avenue, Chestertown, MD 21620
866 Washington Avenue Chestertown MD 21620

1/1

Open House
Fri9/2911-1
866 Washington Avenue 
Chestertown, MD 21620
$165,000
  • Single Family
  • Active
  • MLS # KE10037799
  • 4
    Beds
  • 1
    Full Bath
  • 1
    Total Bath
  • 1,224
    Sq. Ft.

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222 Calvert Street, Chestertown, MD 21620 View this property at 222 Calvert Street, Chestertown, MD 21620
222 Calvert Street Chestertown MD 21620

1/15

222 Calvert Street 
Chestertown, MD 21620
$109,900
  • Single Family
  • Active
  • MLS # KE10037203
  • Updated 3 days ago
  • 2
    Beds
  • 1
    Full Bath
  • 1
    Partial Bath
  • 2
    Total Baths

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