Chestertown, MD Real Estate and Properties for Sale | Berkshire Hathaway HomeServices Fox & Roach

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Chestertown, MD Real Estate and Properties for Sale

$3,150,000
Active
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6520 SWAN CREEK ROAD

ROCK HALL, MD 21661

  • Single Family
  • 7 Beds
  • 7 Baths
  • 12,520 sqft
$2,550,000
Active
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5307 ELBURN LANE

ROCK HALL, MD 21661

  • Commercial
  • 3,457 sqft
$2,500,000
Active
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31436 SASSAFRAS RIVER AVENUE

GALENA, MD 21635

  • Single Family
  • 4 Beds
  • 4 Baths
  • 5,236 sqft
$2,475,000
Active
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26566 LAMBS MEADOW ROAD

WORTON, MD 21678

  • Commercial
  • 25,950 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
$1,800,000
Active
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LITTLE HARBOR WAY #1

CHESTERTOWN, MD 21620

  • Single Family
  • 4 Beds
  • 4 Baths
  • 3,540 sqft
$1,799,000
Active
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11500 POSSUM HOLLOW ROAD

WORTON, MD 21678

  • Single Family
  • 3 Beds
  • 4 Baths
  • 3,138 sqft
$1,650,000
Active
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8796 MARYLAND PARKWAY

CHESTERTOWN, MD 21620

  • Single Family
  • 9 Beds
  • 7 Baths
  • 4,776 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
$1,469,900
Active
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104 MAPLE AVENUE

CHESTERTOWN, MD 21620

  • Commercial
  • 7,296 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
$1,395,000
Active
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8276 BROAD NECK ROAD

CHESTERTOWN, MD 21620

  • Single Family
  • 4 Beds
  • 4 Baths
  • 3,383 sqft
$1,300,000
Active
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327 CANNON STREET

CHESTERTOWN, MD 21620

  • Commercial
  • 3,740 sqft
$1,250,000
Active
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5979 LAWTON AVENUE

ROCK HALL, MD 21661

  • Single Family
  • 5 Beds
  • 5 Baths
  • 3,527 sqft
$1,250,000
Active
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ROCK HALL ROAD

ROCK HALL, MD 21661

  • Vacant Land
$1,250,000
Active
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Lot 1 CARROLL CLARK ROAD

GALENA, MD 21635

  • Vacant Land
$1,245,500
Active
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105 HIGH STREET

CHESTERTOWN, MD 21620

  • Single Family
  • 5 Beds
  • 5 Baths
  • 3,243 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
$1,195,000
Active
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10672 WORTON ROAD

WORTON, MD 21678

  • Single Family
  • 4 Beds
  • 3 Baths
  • 2,872 sqft
$1,195,000
Active
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10700 WORTON ROAD

WORTON, MD 21678

  • Commercial
  • 6,000 sqft
$1,125,000
Active
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#2 LAWTON AVENUE

ROCK HALL, MD 21661

  • Vacant Land
$1,100,000
Active
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25416 COMMERCE LANE

CHESTERTOWN, MD 21620

  • Commercial
  • 5,600 sqft
$1,099,900
Active
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#25 LANDING LANE

CHESTERTOWN, MD 21620

  • Single Family
  • 4 Beds
  • 4 Baths
  • 2,784 sqft
$935,000
Active
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24050 MACS LANE

WORTON, MD 21678

  • Single Family
  • 3 Beds
  • 3 Baths
  • 2,102 sqft
$865,000
Active
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106 QUEEN STREET S

CHESTERTOWN, MD 21620

  • Single Family
  • 3 Beds
  • 4 Baths
  • 2,472 sqft
$850,000
Active
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4020 EASTERN NECK ROAD

ROCK HALL, MD 21661

  • Single Family
  • 4 Beds
  • 2 Baths
  • 3,300 sqft
$850,000
Active
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21190 GREEN LANE

ROCK HALL, MD 21661

  • Vacant Land
$849,900
Active
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104 LITTLE HARBOR WAY

CHESTERTOWN, MD 21620

  • Single Family
  • 3 Beds
  • 3 Baths
  • 1,980 sqft
$839,500
Active
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102 LITTLE HARBOR WAY

CHESTERTOWN, MD 21620

  • Single Family
  • 3 Beds
  • 3 Baths
  • 1,964 sqft
$795,000
Active
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515 WASHINGTON AVENUE

CHESTERTOWN, MD 21620

  • Commercial
$786,900
Active
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#35 LANDING LANE

CHESTERTOWN, MD 21620

  • Single Family
  • 3 Beds
  • 3 Baths
  • 1,964 sqft
$765,900
Active
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#37 LANDING LANE

CHESTERTOWN, MD 21620

  • Single Family
  • 3 Beds
  • 3 Baths
  • 1,964 sqft
$765,000
Active
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24274 WATERVIEW DRIVE

WORTON, MD 21678

  • Single Family
  • 4 Beds
  • 4 Baths
  • 3,006 sqft
$753,500
Active
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#36 LANDING LANE

CHESTERTOWN, MD 21620

  • Single Family
  • 3 Beds
  • 3 Baths
  • 1,964 sqft
$750,000
Active
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201 N LYNCHBURG STREET

CHESTERTOWN, MD 21620

  • Commercial
  • 3,527 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
$665,000
Active
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4819 EASTERN NECK ROAD

ROCK HALL, MD 21661

  • Single Family
  • 3 Beds
  • 3 Baths
  • 1,745 sqft
$663,000
Active
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SWAN CREEK ROAD

ROCK HALL, MD 21661

  • Vacant Land
$650,000
Active
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20694 MERCER AVENUE

ROCK HALL, MD 21661

  • Single Family
  • 4 Beds
  • 2 Baths
  • 2,271 sqft
$649,900
Active
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24204 DRAYTON LANDING DRIVE

WORTON, MD 21678

  • Single Family
  • 3 Beds
  • 2 Baths
  • 2,176 sqft
$649,900
Active
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21173 and 21163 CHESAPEAKE AVENUE

ROCK HALL, MD 21661

  • Single Family
  • 4 Beds
  • 4 Baths
  • 2,944 sqft
$649,000
Active
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14200 METASEQUOIA COURT

GALENA, MD 21635

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

CHESTERTOWN, MD 21620

  • Vacant Land
$585,000
Active
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5807 BLUE CLAW COURT

ROCK HALL, MD 21661

  • Single Family
  • 4 Beds
  • 3 Baths
  • 2,672 sqft
$575,000
Active
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25133 WYMONT PARK ROAD

WORTON, MD 21678

  • Single Family
  • 1 Bed
  • 2 Baths
  • 1,724 sqft
$565,000
Active
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204 DOUBLE CREEK ROAD

CHESTERTOWN, MD 21620

  • Single Family
  • 3 Beds
  • 3 Baths
  • 2,927 sqft
$550,000
Active
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103 SUTTON WAY

CHESTERTOWN, MD 21620

  • Single Family
  • 5 Beds
  • 4 Baths
  • 3,816 sqft
$540,000
Active
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21186 CHESAPEAKE AVENUE

ROCK HALL, MD 21661

  • Single Family
  • 3 Beds
  • 3 Baths
  • 1,760 sqft
$524,900
Active
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101 COLEMAN DRIVE

CHESTERTOWN, MD 21620

  • Single Family
  • 3 Beds
  • 3 Baths
  • 2,268 sqft
$515,000
Active
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101 S MILL STREET

CHESTERTOWN, MD 21620

  • Single Family
  • 2 Beds
  • 3 Baths
  • 1,476 sqft
$499,999
Active
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218 CAMELOT DRIVE

CHESTERTOWN, MD 21620

  • Single Family
  • 5 Beds
  • 4 Baths
  • 3,932 sqft
$499,900
Active
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8620 PARK DRIVE

CHESTERTOWN, MD 21620

  • Single Family
  • 4 Beds
  • 3 Baths
  • 2,524 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
$475,000
Active
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25428 WORTON LYNCH ROAD

WORTON, MD 21678

  • Single Family
  • 3 Beds
  • 3 Baths
  • 1,872 sqft
$468,000
Active
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25750 COLLINS AVENUE

CHESTERTOWN, MD 21620

  • Single Family
  • 3 Beds
  • 2 Baths
  • 3,262 sqft
$450,000
Active
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110 TRAFFORD DRIVE

CHESTERTOWN, MD 21620

  • Single Family
  • 4 Beds
  • 3 Baths
  • 2,880 sqft
$449,000
Active
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21111 CHESAPEAKE AVENUE

ROCK HALL, MD 21661

  • Commercial
$436,500
Active
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5827 S HAWTHORNE AVENUE

ROCK HALL, MD 21661

  • Single Family
  • 3 Beds
  • 1 Bath
  • 1,440 sqft
$429,999
Active
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222 MOUNT VERNON AVENUE

CHESTERTOWN, MD 21620

  • Single Family
  • 4 Beds
  • 2 Baths
  • 1,656 sqft
$429,900
Active
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10781 FERMOY ROAD

CHESTERTOWN, MD 21620

  • Single Family
  • 4 Beds
  • 3 Baths
  • 2,160 sqft
$427,000
Active
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22300 FRAZIER ROAD

ROCK HALL, MD 21661

  • Single Family
  • 3 Beds
  • 2 Baths
  • 2,556 sqft
$399,900
Active
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103 TRAFFORD DRIVE

CHESTERTOWN, MD 21620

  • Single Family
  • 3 Beds
  • 3 Baths
  • 1,944 sqft
$399,900
Active
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522 HIGH STREET

CHESTERTOWN, MD 21620

  • Single Family
  • 2 Beds
  • 3 Baths
  • 1,518 sqft
$399,800
Active
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122 MAIN STREET

GALENA, MD 21635

  • Single Family
  • 4 Beds
  • 3 Baths
  • 1,684 sqft
$399,000
Active
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21424 CATHOLIC AVENUE

ROCK HALL, MD 21661

  • Single Family
  • 4 Beds
  • 2 Baths
  • 1,247 sqft
$394,900
Active
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21123 STRIPER RUN

ROCK HALL, MD 21661

  • Single Family
  • 3 Beds
  • 3 Baths
  • 2,040 sqft
$389,000
Active
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21733 CENTENNIAL LANE

ROCK HALL, MD 21661

  • Single Family
  • 4 Beds
  • 2 Baths
  • 2,162 sqft
$389,000
Active
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240 MERGANSER DRIVE

CHESTERTOWN, MD 21620

  • Single Family
  • 3 Beds
  • 2 Baths
  • 1,120 sqft
$389,000
Active
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6416 EDESVILLE ROAD

ROCK HALL, MD 21661

  • Single Family
  • 3 Beds
  • 3 Baths
  • 2,200 sqft
$385,000
Active
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23043 BAY SHORE SPUR

CHESTERTOWN, MD 21620

  • Single Family
  • 4 Beds
  • 3 Baths
  • 2,630 sqft
$385,000
Active
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107 FLYING CLOUD DRIVE

CHESTERTOWN, MD 21620

  • Single Family
  • 5 Beds
  • 4 Baths
  • 2,534 sqft
$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
$380,000
Active
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213 BYFORD DRIVE

CHESTERTOWN, MD 21620

  • Single Family
  • 4 Beds
  • 2 Baths
  • 1,277 sqft
$375,000
Active
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105 DOGWOOD DRIVE

GALENA, MD 21635

  • Single Family
  • 3 Beds
  • 2 Baths
  • 1,764 sqft
$375,000
Active
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5686 S MAIN ST

ROCK HALL, MD 21661

  • Single Family
  • 3 Beds
  • 2 Baths
  • 1,326 sqft
$375,000
Active
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21336 HAVEN ROAD

ROCK HALL, MD 21661

  • Single Family
  • 3 Beds
  • 2 Baths
  • 1,684 sqft
$375,000
Active
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117 WATER STREET N #2A

CHESTERTOWN, MD 21620

  • Single Family
  • 2 Beds
  • 1 Bath
  • 787 sqft
$374,900
Active
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21124 STRIPER RUN

ROCK HALL, MD 21661

  • Single Family
  • 3 Beds
  • 3 Baths
  • 1,712 sqft
$370,000
Active
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21384 E SHARP STREET

ROCK HALL, MD 21661

  • Single Family
  • 3 Beds
  • 2 Baths
  • 1,574 sqft
$364,900
Active
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21131 STRIPER RUN

ROCK HALL, MD 21661

  • Single Family
  • 3 Beds
  • 3 Baths
  • 1,626 sqft
$359,900
Active
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5862 N MAIN STREET

ROCK HALL, MD 21661

  • Single Family
  • 3 Beds
  • 2 Baths
  • 1,381 sqft
$350,000
Active
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117 WATER STREET N #2B

CHESTERTOWN, MD 21620

  • Single Family
  • 1 Bed
  • 1 Bath
  • 850 sqft
$350,000
Active
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21305 HAVEN ROAD

ROCK HALL, MD 21661

  • Single Family
  • 4 Beds
  • 2 Baths
  • 1,499 sqft
$344,900
Active
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109 WILTON ROAD

CHESTERTOWN, MD 21620

  • Single Family
  • 3 Beds
  • 2 Baths
  • 1,392 sqft
$340,000
Active
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214 SILVER HEEL ROAD

CHESTERTOWN, MD 21620

  • Single Family
  • 4 Beds
  • 3 Baths
  • 1,972 sqft
$340,000
Active
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21232 ROCK HALL AVENUE

ROCK HALL, MD 21661

  • Single Family
  • 2 Beds
  • 2 Baths
  • 1,200 sqft
$329,900
Active
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102 FLYING CLOUD DRIVE

CHESTERTOWN, MD 21620

  • Single Family
  • 3 Beds
  • 3 Baths
  • 1,896 sqft
$325,000
Active
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21279 W SHARP STREET

ROCK HALL, MD 21661

  • Commercial
  • 3,430 sqft
$324,900
Active
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517 ROUND TOP ROAD

CHESTERTOWN, MD 21620

  • Single Family
  • 3 Beds
  • 1 Bath
  • 1,248 sqft
$320,000
Active
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11054 AUSTIN LANE

WORTON, MD 21678

  • Single Family
  • 3 Beds
  • 2 Baths
  • 1,376 sqft
$320,000
Active
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8706 ELM ROAD

CHESTERTOWN, MD 21620

  • Single Family
  • 3 Beds
  • 2 Baths
  • 1,232 sqft
$320,000
Active
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222 DUTCHESS ROAD

CHESTERTOWN, MD 21620

  • Single Family
  • 3 Beds
  • 2 Baths
  • 1,096 sqft
$310,000
Active
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0 will be 11037 BOTTOM ROAD

WORTON, MD 21678

  • Single Family
  • 3 Beds
  • 2 Baths
  • 1,300 sqft
$309,900
Active
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304 HADAWAY DRIVE

CHESTERTOWN, MD 21620

  • Single Family
  • 4 Beds
  • 2 Baths
  • 1,325 sqft
$300,000
Active
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21435 ROCK HALL AVENUE

ROCK HALL, MD 21661

  • Commercial
  • 990 sqft
$299,000
Active
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208 CENTRAL DRIVE

CHESTERTOWN, MD 21620

  • Single Family
  • 3 Beds
  • 1 Bath
  • 1,120 sqft
$298,000
Active
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4818 PINEY NECK ROAD

ROCK HALL, MD 21661

  • Single Family
  • 3 Beds
  • 1 Bath
  • 1,892 sqft
$288,500
Active
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11167 OAK LANE

WORTON, MD 21678

  • Single Family
  • 3 Beds
  • 1 Bath
  • 960 sqft
$280,000
Active
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11060 PLUM DRIVE

WORTON, MD 21678

  • Single Family
  • 3 Beds
  • 1 Bath
  • 1,008 sqft

Nearby Cities to Chestertown

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 6/29/2026 05:17 PM PST. Copyright 2026 BRIGHT MLS – All Rights Reserved.