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21620 Real Estate and Properties for Sale

$2,000
Active
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351 CALVERT STREET

CHESTERTOWN, MD 21620

  • Rental
  • 3 Beds
  • 1 Bath
  • 1,122 sqft
$325,000
Coming Soon
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896 WASHINGTON AVENUE

CHESTERTOWN, MD 21620

  • Single Family
  • 3 Beds
  • 1 Bath
  • 1,000 sqft
$735,000
Coming Soon
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210 N QUEEN STREET

CHESTERTOWN, MD 21620

  • Single Family
  • 4 Beds
  • 3 Baths
  • 2,730 sqft
$475,000
Active
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105 N WATER STREET #2

CHESTERTOWN, MD 21620

  • Single Family
  • 2 Beds
  • 2 Baths
  • 1,011 sqft
$2,500
Active
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8890 FAIRLEE ROAD

CHESTERTOWN, MD 21620

  • Rental
  • 3 Beds
  • 2 Baths
  • 1,232 sqft
$279,900
Active
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22481 GOOSE HOLLOW DRIVE

CHESTERTOWN, MD 21620

  • Single Family
  • 3 Beds
  • 2 Baths
  • 1,296 sqft
$324,900
Active
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517 ROUND TOP ROAD

CHESTERTOWN, MD 21620

  • Single Family
  • 3 Beds
  • 1 Bath
  • 1,248 sqft
$1,400
Active
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103 S LYNCHBURG STREET

CHESTERTOWN, MD 21620

  • Rental
  • 2 Beds
  • 2 Baths
  • 1,040 sqft
$247,000
Active
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104 CONLEY DRIVE

CHESTERTOWN, MD 21620

  • Single Family
  • 3 Beds
  • 2 Baths
  • 1,280 sqft
$515,000
Active
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101 S MILL STREET

CHESTERTOWN, MD 21620

  • Single Family
  • 2 Beds
  • 3 Baths
  • 1,476 sqft
$75,000
Active
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FAIRLEE ROAD

CHESTERTOWN, MD 21620

  • Vacant Land
$284,900
Active
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104 ACORN DRIVE

CHESTERTOWN, MD 21620

  • Single Family
  • 3 Beds
  • 3 Baths
  • 1,900 sqft
$100,000
Active
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234 N COLLEGE AVENUE

CHESTERTOWN, MD 21620

  • Single Family
  • 2 Beds
  • 1 Bath
  • 1,296 sqft
$468,000
Active
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25750 COLLINS AVENUE

CHESTERTOWN, MD 21620

  • Single Family
  • 3 Beds
  • 2 Baths
  • 3,262 sqft
$1,100,000
Active
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25416 COMMERCE LANE

CHESTERTOWN, MD 21620

  • Commercial
  • 5,600 sqft
$99,900
Active
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110 PROSPECT STREET

CHESTERTOWN, MD 21620

  • Single Family
  • 3 Beds
  • 2 Baths
  • 2,210 sqft
$2,950
Active
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222 MOUNT VERNON AVENUE

CHESTERTOWN, MD 21620

  • Rental
  • 4 Beds
  • 2 Baths
  • 1,656 sqft
$80,000
Active
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8886 GEORGETOWN ROAD

CHESTERTOWN, MD 21620

  • Vacant Land
$200,000
Active
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21172 WYOMING AVENUE

CHESTERTOWN, MD 21620

  • Single Family
  • 4 Beds
  • 1 Bath
  • 2,920 sqft
$429,900
Active
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10781 FERMOY ROAD

CHESTERTOWN, MD 21620

  • Single Family
  • 4 Beds
  • 3 Baths
  • 2,160 sqft
$380,000
Active
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213 BYFORD DRIVE

CHESTERTOWN, MD 21620

  • Single Family
  • 4 Beds
  • 2 Baths
  • 1,277 sqft
$1,650,000
Active
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8796 MARYLAND PARKWAY

CHESTERTOWN, MD 21620

  • Commercial
  • 5,000 sqft
$1,200,000
Active
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202 ROYSTON SHORES ROAD

CHESTERTOWN, MD 21620

  • Single Family
  • 4 Beds
  • 3 Baths
  • 2,292 sqft
$110,000
Active
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1906 PONDTOWN ROAD

CHESTERTOWN, MD 21620

  • Vacant Land
$265,000
Active
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1904 PONDTOWN ROAD

CHESTERTOWN, MD 21620

  • Single Family
  • 3 Beds
  • 1 Bath
  • 1,967 sqft
$15,000
Active
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23741 L ROAD

CHESTERTOWN, MD 21620

  • Vacant Land
$399,900
Active
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522 HIGH STREET

CHESTERTOWN, MD 21620

  • Single Family
  • 2 Beds
  • 3 Baths
  • 1,518 sqft
$2,400
Active
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1010 TWIN COURT

CHESTERTOWN, MD 21620

  • Rental
  • 4 Beds
  • 2 Baths
  • 1,476 sqft
$55,000
Active
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MAP 36 PARCEL 80 WATERTOWER ROAD

CHESTERTOWN, MD 21620

  • Vacant Land
$329,900
Active
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102 FLYING CLOUD DRIVE

CHESTERTOWN, MD 21620

  • Single Family
  • 3 Beds
  • 3 Baths
  • 1,896 sqft
$1,450,000
Active
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22470 FAIRGALE FARM LANE

CHESTERTOWN, MD 21620

  • Single Family
  • 4 Beds
  • 5 Baths
  • 4,257 sqft
$6,000
Active
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23683 L ROAD

CHESTERTOWN, MD 21620

  • Vacant Land
$1,450
Active
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128 N QUEEN STREET #3

CHESTERTOWN, MD 21620

  • Rental
  • 1 Bed
  • 1 Bath
  • 900 sqft
$79,000
Active
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SANDY BOTTOM ROAD

CHESTERTOWN, MD 21620

  • Vacant Land
$309,900
Active
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304 HADAWAY DRIVE

CHESTERTOWN, MD 21620

  • Single Family
  • 4 Beds
  • 2 Baths
  • 1,325 sqft
$59,999
Active
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228 MERGANSER DRIVE

CHESTERTOWN, MD 21620

  • Vacant Land
$2,600
Active
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104 CEDAR STREET

CHESTERTOWN, MD 21620

  • Rental
  • 3 Beds
  • 3 Baths
  • 2,612 sqft
$135,000
Active
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109 2ND STREET

CHESTERTOWN, MD 21620

  • Vacant Land
$385,000
Active
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107 FLYING CLOUD DRIVE

CHESTERTOWN, MD 21620

  • Single Family
  • 5 Beds
  • 4 Baths
  • 2,534 sqft
$340,000
Active
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214 SILVER HEEL ROAD

CHESTERTOWN, MD 21620

  • Single Family
  • 4 Beds
  • 3 Baths
  • 1,972 sqft
$109,999
Active
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116 CROSS STREET

CHESTERTOWN, MD 21620

  • Vacant Land
$259,900
Active
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103 METCALF RD

CHESTERTOWN, MD 21620

  • Single Family
  • 3 Beds
  • 2 Baths
  • 1,280 sqft
$2,050
Active
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104 MAPLE AVENUE #6

CHESTERTOWN, MD 21620

  • Rental
  • 2 Beds
  • 2 Baths
  • 900 sqft
$1,469,900
Active
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104 MAPLE AVENUE

CHESTERTOWN, MD 21620

  • Commercial
  • 7,296 sqft
$320,000
Active
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8706 ELM ROAD

CHESTERTOWN, MD 21620

  • Single Family
  • 3 Beds
  • 2 Baths
  • 1,232 sqft
$299,000
Active
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208 CENTRAL DRIVE

CHESTERTOWN, MD 21620

  • Single Family
  • 3 Beds
  • 1 Bath
  • 1,120 sqft
$389,000
Active
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240 MERGANSER DRIVE

CHESTERTOWN, MD 21620

  • Single Family
  • 3 Beds
  • 2 Baths
  • 1,120 sqft
$244,500
Active
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21217 TEXAS AVENUE

CHESTERTOWN, MD 21620

  • Single Family
  • 2 Beds
  • 1 Bath
  • 912 sqft
$898,000
Active
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226 S WATER STREET

CHESTERTOWN, MD 21620

  • Single Family
  • 3 Beds
  • 4 Baths
  • 2,172 sqft
$1,300,000
Active
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327 CANNON STREET

CHESTERTOWN, MD 21620

  • Commercial
  • 3,740 sqft
$550,000
Active
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103 SUTTON WAY

CHESTERTOWN, MD 21620

  • Single Family
  • 5 Beds
  • 4 Baths
  • 3,816 sqft
$3,000
Active
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COGAR ROAD

CHESTERTOWN, MD 21620

  • Vacant Land
$225,000
Active
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HAACKE DRIVE LOT 3

CHESTERTOWN, MD 21620

  • Commercial
$250,000
Active
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SCHEELER ROAD LOT 2

CHESTERTOWN, MD 21620

  • Vacant Land
$524,900
Active
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101 COLEMAN DRIVE

CHESTERTOWN, MD 21620

  • Single Family
  • 3 Beds
  • 3 Baths
  • 2,268 sqft
$3,000
Active
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TONOPAH ROAD

CHESTERTOWN, MD 21620

  • Vacant Land
$3,000
Active
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LENAPAH RD

CHESTERTOWN, MD 21620

  • Vacant Land
$200,000
Active
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0 ROUND TOP ROAD

CHESTERTOWN, MD 21620

  • Vacant Land
$865,000
Active
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106 QUEEN STREET S

CHESTERTOWN, MD 21620

  • Single Family
  • 3 Beds
  • 4 Baths
  • 2,472 sqft
$1,395,000
Active
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8276 BROAD NECK ROAD

CHESTERTOWN, MD 21620

  • Single Family
  • 4 Beds
  • 4 Baths
  • 3,383 sqft
$1,800
Active
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7501 CHURCH HILL ROAD #5

CHESTERTOWN, MD 21620

  • Rental
  • 2 Beds
  • 1 Bath
  • 1,000 sqft
$200,000
Active
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117 WATER STREET N #1B

CHESTERTOWN, MD 21620

  • Single Family
  • 1 Bed
  • 1 Bath
  • 700 sqft
$375,000
Active
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117 WATER STREET N #2A

CHESTERTOWN, MD 21620

  • Single Family
  • 2 Beds
  • 1 Bath
  • 787 sqft
$350,000
Active
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117 WATER STREET N #2B

CHESTERTOWN, MD 21620

  • Single Family
  • 1 Bed
  • 1 Bath
  • 850 sqft
$1,600,000
Active
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117 WATER STREET N #1A, 1B, 2A, & 2B

CHESTERTOWN, MD 21620

  • Single Family
  • 7 Beds
  • 5 Baths
  • 5,400 sqft
$685,000
Active
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117 WATER STREET N #1A

CHESTERTOWN, MD 21620

  • Single Family
  • 3 Beds
  • 3 Baths
  • 3,000 sqft
$750,000
Active
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201 N LYNCHBURG STREET

CHESTERTOWN, MD 21620

  • Vacant Land
$565,000
Active
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204 DOUBLE CREEK ROAD

CHESTERTOWN, MD 21620

  • Single Family
  • 3 Beds
  • 3 Baths
  • 2,927 sqft
$15,000
Active
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22681 WOOD YARD LANE

CHESTERTOWN, MD 21620

  • Vacant Land
$384,000
Active
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6746 QUAKER NECK ROAD

CHESTERTOWN, MD 21620

  • Single Family
  • 5 Beds
  • 3 Baths
  • 3,371 sqft
$384,000
Active
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6746 QUAKER ROAD

CHESTERTOWN, MD 21620

  • Commercial
  • 3,371 sqft
$499,999
Active
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218 CAMELOT DRIVE

CHESTERTOWN, MD 21620

  • Single Family
  • 5 Beds
  • 4 Baths
  • 3,932 sqft
$450,000
Active
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110 TRAFFORD DRIVE

CHESTERTOWN, MD 21620

  • Single Family
  • 4 Beds
  • 3 Baths
  • 2,880 sqft
$765,900
Active
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#37 LANDING LANE

CHESTERTOWN, MD 21620

  • Single Family
  • 3 Beds
  • 3 Baths
  • 1,964 sqft
$753,500
Active
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#36 LANDING LANE

CHESTERTOWN, MD 21620

  • Single Family
  • 3 Beds
  • 3 Baths
  • 1,964 sqft
$786,900
Active
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#35 LANDING LANE

CHESTERTOWN, MD 21620

  • Single Family
  • 3 Beds
  • 3 Baths
  • 1,964 sqft
$839,500
Active
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102 LITTLE HARBOR WAY

CHESTERTOWN, MD 21620

  • Single Family
  • 3 Beds
  • 3 Baths
  • 1,964 sqft
$813,900
Active
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104 LANDING LANE

CHESTERTOWN, MD 21620

  • Single Family
  • 3 Beds
  • 4 Baths
  • 2,192 sqft
$1,099,900
Active
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#25 LANDING LANE

CHESTERTOWN, MD 21620

  • Single Family
  • 4 Beds
  • 4 Baths
  • 2,784 sqft
$90,000
Active
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GEORGETOWN ROAD

CHESTERTOWN, MD 21620

  • Vacant Land
$635,000
Active
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108 LITTLE HARBOR WAY

CHESTERTOWN, MD 21620

  • Vacant Land
$799,900
Active
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106 LANDING LANE

CHESTERTOWN, MD 21620

  • Single Family
  • 3 Beds
  • 4 Baths
  • 2,092 sqft
$849,900
Active
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104 LITTLE HARBOR WAY

CHESTERTOWN, MD 21620

  • Single Family
  • 3 Beds
  • 3 Baths
  • 1,980 sqft
$1,245,500
Active
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105 HIGH STREET

CHESTERTOWN, MD 21620

  • Single Family
  • 5 Beds
  • 5 Baths
  • 3,243 sqft
$499,900
Active
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8620 PARK DRIVE

CHESTERTOWN, MD 21620

  • Single Family
  • 4 Beds
  • 3 Baths
  • 2,524 sqft
$320,000
Active
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222 DUTCHESS ROAD

CHESTERTOWN, MD 21620

  • Single Family
  • 3 Beds
  • 2 Baths
  • 1,096 sqft
$10,000
Active
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CLARISSA ROAD

CHESTERTOWN, MD 21620

  • Vacant Land
$19,500
Active
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404 SPRING ROAD

CHESTERTOWN, MD 21620

  • Vacant Land
$499,999
Active
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103 LANDING LANE

CHESTERTOWN, MD 21620

  • Single Family
  • 2 Beds
  • 3 Baths
  • 2,100 sqft
$385,000
Active
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23043 BAY SHORE SPUR

CHESTERTOWN, MD 21620

  • Single Family
  • 4 Beds
  • 3 Baths
  • 2,630 sqft
$2,200,000
Active
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7989 QUAKER NECK ROAD

CHESTERTOWN, MD 21620

  • Single Family
  • 5 Beds
  • 5 Baths
  • 4,305 sqft
$10,000
Active
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BUCK NECK LANDING ROAD

CHESTERTOWN, MD 21620

  • Vacant Land
$25,000
Active
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JOHNSONTOWN ROAD

CHESTERTOWN, MD 21620

  • Vacant Land
$9,000
Active
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BUCK NECK ROAD

CHESTERTOWN, MD 21620

  • Vacant Land
$9,000
Active
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KINGLET ROAD

CHESTERTOWN, MD 21620

  • Vacant Land
$150,000
Active
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CAULKS FIELD ROAD

CHESTERTOWN, MD 21620

  • Vacant Land
$150,000
Active
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GEORGETOWN ROAD SE

CHESTERTOWN, MD 21620

  • Vacant Land
$1,800,000
Active
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LITTLE HARBOR WAY #1

CHESTERTOWN, MD 21620

  • Single Family
  • 4 Beds
  • 4 Baths
  • 3,540 sqft
$59,000
Active
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OLD MORGNEC ROAD

CHESTERTOWN, MD 21620

  • Vacant Land
$5,000
Active
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TOWHEE ROAD

CHESTERTOWN, MD 21620

  • Vacant Land
The data relating to real estate for sale on this web site comes in part from the IDX program of BRIGHT MLS. Information is supplied by seller and other third parties and has not been verified. All information provided is deemed reliable but is not guaranteed. All properties are subject to prior sale or withdrawal. Data may not be reproduced or redistributed and may not be used for any purpose other than consumers’ personal, non-commercial use. MLS Data Last Updated 6/30/2026 01:30 AM PST. Copyright 2026 BRIGHT MLS – All Rights Reserved.