Recently Viewed Properties
88 Results

Chestertown, MD Real Estate & Homes For Sale

Add

Oops! We need you to add a location.
more
Selecting these elements will cause content on the page to be updated. Near by
NEARBY
    Selecting these elements will cause content on the page to be updated. History
    HISTORY
      Save this Search
      Filters
      Selection will refresh the page with new results. properties
      —
      You’ll get email updates when new properties matching this criteria go on the market. You can also run these searches quickly under “Properties & Searches” at the top of every page.
      Selection will refresh the page with new results.
      Selection will refresh the page with new results. properties
      Property Type
      PRICE
      to
      BEDROOMS
      BATHROOMS
      STATUS (only include)
      Lot Sizeto
      FEATURES

      Add

      Max keywords reached
      Save this Search
      Hide Map
      Order By

      Save this Search

      88 Results
      Order By

      Use previous and next buttons to navigate

      24295 Langford Rd, Chestertown, MD 21620 - Photo 1
      Coming Soon

      1/1

      24295 Langford Rd  Chestertown, MD 21620

      $445,000
      • Single Family
      • Coming Soon
      • MLS # MDKE2006320
      • Updated 1 day ago
      • 3
        Beds
      • 2
        Full Baths
      • 1
        Partial Bath
      • 3
        Total Baths
      • 3,510
        Sq. Ft.
      • 4
        Car Garage
      Listed by Chesapeake Real Estate Associates, LLC, Amy L Larrauri

      Use previous and next buttons to navigate

      240 Merganser Dr, Chestertown, MD 21620 - Photo 1 240 Merganser Dr, Chestertown, MD 21620 - Photo 2 240 Merganser Dr, Chestertown, MD 21620 - Photo 3 240 Merganser Dr, Chestertown, MD 21620 - Photo 4 240 Merganser Dr, Chestertown, MD 21620 - Photo 5 240 Merganser Dr, Chestertown, MD 21620 - Photo 6 240 Merganser Dr, Chestertown, MD 21620 - Photo 7 240 Merganser Dr, Chestertown, MD 21620 - Photo 8
      Coming Soon

      1/8

      240 Merganser Dr  Chestertown, MD 21620

      $425,000
      • Single Family
      • Coming Soon
      • MLS # MDQA2016900
      • Updated 12 hours ago
      • 3
        Beds
      • 2
        Full Baths
      • 2
        Total Baths
      • 1,664
        Sq. Ft.
      Listed by Chesapeake Real Estate Associates, LLC, Erin Anderson

      Use previous and next buttons to navigate

      10594 Millbrook Dr, Chestertown, MD 21620 - Photo 1 10594 Millbrook Dr, Chestertown, MD 21620 - Photo 2 10594 Millbrook Dr, Chestertown, MD 21620 - Photo 3 10594 Millbrook Dr, Chestertown, MD 21620 - Photo 4 10594 Millbrook Dr, Chestertown, MD 21620 - Photo 5 10594 Millbrook Dr, Chestertown, MD 21620 - Photo 6 10594 Millbrook Dr, Chestertown, MD 21620 - Photo 7 10594 Millbrook Dr, Chestertown, MD 21620 - Photo 8
      Coming Soon

      1/8

      Open House
      Sun4/1912-2

      10594 Millbrook Dr  Chestertown, MD 21620

      $329,000
      • Single Family
      • Coming Soon
      • MLS # MDKE2006378
      • Updated 2 hours ago
      • 3
        Beds
      • 2
        Full Baths
      • 2
        Total Baths
      • 1,499
        Sq. Ft.
      Listed by Chesapeake Real Estate Associates, LLC, Maryn J. LeClair

      Use previous and next buttons to navigate

      10087 John Carvill Rd, Chestertown, MD 21620 - Photo 1 10087 John Carvill Rd, Chestertown, MD 21620 - Photo 2 10087 John Carvill Rd, Chestertown, MD 21620 - Photo 3 10087 John Carvill Rd, Chestertown, MD 21620 - Photo 4 10087 John Carvill Rd, Chestertown, MD 21620 - Photo 5 10087 John Carvill Rd, Chestertown, MD 21620 - Photo 6 10087 John Carvill Rd, Chestertown, MD 21620 - Photo 7 10087 John Carvill Rd, Chestertown, MD 21620 - Photo 8 10087 John Carvill Rd, Chestertown, MD 21620 - Photo 9 10087 John Carvill Rd, Chestertown, MD 21620 - Photo 10 10087 John Carvill Rd, Chestertown, MD 21620 - Photo 11 10087 John Carvill Rd, Chestertown, MD 21620 - Photo 12 10087 John Carvill Rd, Chestertown, MD 21620 - Photo 13 10087 John Carvill Rd, Chestertown, MD 21620 - Photo 14 10087 John Carvill Rd, Chestertown, MD 21620 - Photo 15 10087 John Carvill Rd, Chestertown, MD 21620 - Photo 16 10087 John Carvill Rd, Chestertown, MD 21620 - Photo 17 10087 John Carvill Rd, Chestertown, MD 21620 - Photo 18 10087 John Carvill Rd, Chestertown, MD 21620 - Photo 19 10087 John Carvill Rd, Chestertown, MD 21620 - Photo 20 10087 John Carvill Rd, Chestertown, MD 21620 - Photo 21 10087 John Carvill Rd, Chestertown, MD 21620 - Photo 22 10087 John Carvill Rd, Chestertown, MD 21620 - Photo 23 10087 John Carvill Rd, Chestertown, MD 21620 - Photo 24 10087 John Carvill Rd, Chestertown, MD 21620 - Photo 25 10087 John Carvill Rd, Chestertown, MD 21620 - Photo 26 10087 John Carvill Rd, Chestertown, MD 21620 - Photo 27 10087 John Carvill Rd, Chestertown, MD 21620 - Photo 28 10087 John Carvill Rd, Chestertown, MD 21620 - Photo 29 10087 John Carvill Rd, Chestertown, MD 21620 - Photo 30 10087 John Carvill Rd, Chestertown, MD 21620 - Photo 31 10087 John Carvill Rd, Chestertown, MD 21620 - Photo 32 10087 John Carvill Rd, Chestertown, MD 21620 - Photo 33 10087 John Carvill Rd, Chestertown, MD 21620 - Photo 34 10087 John Carvill Rd, Chestertown, MD 21620 - Photo 35 10087 John Carvill Rd, Chestertown, MD 21620 - Photo 36 10087 John Carvill Rd, Chestertown, MD 21620 - Photo 37 10087 John Carvill Rd, Chestertown, MD 21620 - Photo 38 10087 John Carvill Rd, Chestertown, MD 21620 - Photo 39 10087 John Carvill Rd, Chestertown, MD 21620 - Photo 40 10087 John Carvill Rd, Chestertown, MD 21620 - Photo 41 10087 John Carvill Rd, Chestertown, MD 21620 - Photo 42 10087 John Carvill Rd, Chestertown, MD 21620 - Photo 43 10087 John Carvill Rd, Chestertown, MD 21620 - Photo 44 10087 John Carvill Rd, Chestertown, MD 21620 - Photo 45 10087 John Carvill Rd, Chestertown, MD 21620 - Photo 46 10087 John Carvill Rd, Chestertown, MD 21620 - Photo 47 10087 John Carvill Rd, Chestertown, MD 21620 - Photo 48 10087 John Carvill Rd, Chestertown, MD 21620 - Photo 49 10087 John Carvill Rd, Chestertown, MD 21620 - Photo 50 10087 John Carvill Rd, Chestertown, MD 21620 - Photo 51 10087 John Carvill Rd, Chestertown, MD 21620 - Photo 52 10087 John Carvill Rd, Chestertown, MD 21620 - Photo 53 10087 John Carvill Rd, Chestertown, MD 21620 - Photo 54 10087 John Carvill Rd, Chestertown, MD 21620 - Photo 55 10087 John Carvill Rd, Chestertown, MD 21620 - Photo 56 10087 John Carvill Rd, Chestertown, MD 21620 - Photo 57 10087 John Carvill Rd, Chestertown, MD 21620 - Photo 58 10087 John Carvill Rd, Chestertown, MD 21620 - Photo 59 10087 John Carvill Rd, Chestertown, MD 21620 - Photo 60 10087 John Carvill Rd, Chestertown, MD 21620 - Photo 61 10087 John Carvill Rd, Chestertown, MD 21620 - Photo 62 10087 John Carvill Rd, Chestertown, MD 21620 - Photo 63
      Just Listed

      1/63

      10087 John Carvill Rd  Chestertown, MD 21620

      $695,000
      • Single Family
      • Active
      • MLS # MDKE2006324
      • Updated 4 days ago
      • 3
        Beds
      • 2
        Full Baths
      • 2
        Total Baths
      • 1,566
        Sq. Ft.
      Listed by Coldwell Banker Chesapeake Real Estate Company, Jennifer L Mobley

      Use previous and next buttons to navigate

      126 Char nor Manor Blvd, Chestertown, MD 21620 - Photo 1 126 Char nor Manor Blvd, Chestertown, MD 21620 - Photo 2 126 Char nor Manor Blvd, Chestertown, MD 21620 - Photo 3 126 Char nor Manor Blvd, Chestertown, MD 21620 - Photo 4
      Coming Soon

      1/4

      Open House
      Fri4/245-7

      126 Char nor Manor Blvd  Chestertown, MD 21620

      $349,000
      • Single Family
      • Coming Soon
      • MLS # MDQA2016812
      • Updated 4 days ago
      • 3
        Beds
      • 2
        Full Baths
      • 2
        Total Baths
      • 1,304
        Sq. Ft.
      • 2
        Car Garage
      Listed by RE/MAX Executive, Crystal M Smith

      Use previous and next buttons to navigate

      2032 Pondtown Rd, Chestertown, MD 21620 - Photo 1 2032 Pondtown Rd, Chestertown, MD 21620 - Photo 2 2032 Pondtown Rd, Chestertown, MD 21620 - Photo 3 2032 Pondtown Rd, Chestertown, MD 21620 - Photo 4 2032 Pondtown Rd, Chestertown, MD 21620 - Photo 5 2032 Pondtown Rd, Chestertown, MD 21620 - Photo 6 2032 Pondtown Rd, Chestertown, MD 21620 - Photo 7 2032 Pondtown Rd, Chestertown, MD 21620 - Photo 8 2032 Pondtown Rd, Chestertown, MD 21620 - Photo 9 2032 Pondtown Rd, Chestertown, MD 21620 - Photo 10 2032 Pondtown Rd, Chestertown, MD 21620 - Photo 11 2032 Pondtown Rd, Chestertown, MD 21620 - Photo 12 2032 Pondtown Rd, Chestertown, MD 21620 - Photo 13 2032 Pondtown Rd, Chestertown, MD 21620 - Photo 14 2032 Pondtown Rd, Chestertown, MD 21620 - Photo 15 2032 Pondtown Rd, Chestertown, MD 21620 - Photo 16 2032 Pondtown Rd, Chestertown, MD 21620 - Photo 17 2032 Pondtown Rd, Chestertown, MD 21620 - Photo 18 2032 Pondtown Rd, Chestertown, MD 21620 - Photo 19 2032 Pondtown Rd, Chestertown, MD 21620 - Photo 20 2032 Pondtown Rd, Chestertown, MD 21620 - Photo 21 2032 Pondtown Rd, Chestertown, MD 21620 - Photo 22 2032 Pondtown Rd, Chestertown, MD 21620 - Photo 23 2032 Pondtown Rd, Chestertown, MD 21620 - Photo 24 2032 Pondtown Rd, Chestertown, MD 21620 - Photo 25 2032 Pondtown Rd, Chestertown, MD 21620 - Photo 26 2032 Pondtown Rd, Chestertown, MD 21620 - Photo 27 2032 Pondtown Rd, Chestertown, MD 21620 - Photo 28 2032 Pondtown Rd, Chestertown, MD 21620 - Photo 29 2032 Pondtown Rd, Chestertown, MD 21620 - Photo 30 2032 Pondtown Rd, Chestertown, MD 21620 - Photo 31 2032 Pondtown Rd, Chestertown, MD 21620 - Photo 32
      Just Listed

      1/32

      2032 Pondtown Rd  Chestertown, MD 21620

      $325,000
      • Single Family
      • Active
      • MLS # MDQA2016688
      • Updated 1 day ago
      • 3
        Beds
      • 2
        Full Baths
      • 2
        Total Baths
      • 1,120
        Sq. Ft.
      Listed by Northrop Realty, Joie L White

      Use previous and next buttons to navigate

      115 Acorn Dr, Chestertown, MD 21620 - Photo 1
      Coming Soon

      1/1

      Open House
      Sat5/211-1

      115 Acorn Dr  Chestertown, MD 21620

      $296,000
      • Townhouse
      • Coming Soon
      • MLS # MDKE2006360
      • Updated 2 days ago
      • 2
        Beds
      • 2
        Full Baths
      • 1
        Partial Bath
      • 3
        Total Baths
      • 1,864
        Sq. Ft.
      • 1
        Car Garage
      Listed by Chesapeake Real Estate Associates, LLC, Amy L Larrauri

      Use previous and next buttons to navigate

      21217 Texas Ave, Chestertown, MD 21620 - Photo 1 21217 Texas Ave, Chestertown, MD 21620 - Photo 2 21217 Texas Ave, Chestertown, MD 21620 - Photo 3 21217 Texas Ave, Chestertown, MD 21620 - Photo 4 21217 Texas Ave, Chestertown, MD 21620 - Photo 5 21217 Texas Ave, Chestertown, MD 21620 - Photo 6 21217 Texas Ave, Chestertown, MD 21620 - Photo 7 21217 Texas Ave, Chestertown, MD 21620 - Photo 8 21217 Texas Ave, Chestertown, MD 21620 - Photo 9 21217 Texas Ave, Chestertown, MD 21620 - Photo 10 21217 Texas Ave, Chestertown, MD 21620 - Photo 11 21217 Texas Ave, Chestertown, MD 21620 - Photo 12 21217 Texas Ave, Chestertown, MD 21620 - Photo 13 21217 Texas Ave, Chestertown, MD 21620 - Photo 14 21217 Texas Ave, Chestertown, MD 21620 - Photo 15 21217 Texas Ave, Chestertown, MD 21620 - Photo 16 21217 Texas Ave, Chestertown, MD 21620 - Photo 17 21217 Texas Ave, Chestertown, MD 21620 - Photo 18 21217 Texas Ave, Chestertown, MD 21620 - Photo 19
      Just Listed

      1/19

      21217 Texas Ave  Chestertown, MD 21620

      $265,000
      • Single Family
      • Active
      • MLS # MDKE2006364
      • Updated 4 days ago
      • 2
        Beds
      • 1
        Full Bath
      • 1
        Total Bath
      • 912
        Sq. Ft.
      Listed by RE/MAX Leading Edge, Terry L Catalano

      Use previous and next buttons to navigate

      226 S Water St, Chestertown, MD 21620 - Photo 1 226 S Water St, Chestertown, MD 21620 - Photo 2 226 S Water St, Chestertown, MD 21620 - Photo 3 226 S Water St, Chestertown, MD 21620 - Photo 4 226 S Water St, Chestertown, MD 21620 - Photo 5 226 S Water St, Chestertown, MD 21620 - Photo 6 226 S Water St, Chestertown, MD 21620 - Photo 7 226 S Water St, Chestertown, MD 21620 - Photo 8 226 S Water St, Chestertown, MD 21620 - Photo 9 226 S Water St, Chestertown, MD 21620 - Photo 10 226 S Water St, Chestertown, MD 21620 - Photo 11 226 S Water St, Chestertown, MD 21620 - Photo 12 226 S Water St, Chestertown, MD 21620 - Photo 13 226 S Water St, Chestertown, MD 21620 - Photo 14 226 S Water St, Chestertown, MD 21620 - Photo 15 226 S Water St, Chestertown, MD 21620 - Photo 16 226 S Water St, Chestertown, MD 21620 - Photo 17 226 S Water St, Chestertown, MD 21620 - Photo 18 226 S Water St, Chestertown, MD 21620 - Photo 19 226 S Water St, Chestertown, MD 21620 - Photo 20 226 S Water St, Chestertown, MD 21620 - Photo 21 226 S Water St, Chestertown, MD 21620 - Photo 22 226 S Water St, Chestertown, MD 21620 - Photo 23 226 S Water St, Chestertown, MD 21620 - Photo 24 226 S Water St, Chestertown, MD 21620 - Photo 25 226 S Water St, Chestertown, MD 21620 - Photo 26 226 S Water St, Chestertown, MD 21620 - Photo 27 226 S Water St, Chestertown, MD 21620 - Photo 28 226 S Water St, Chestertown, MD 21620 - Photo 29 226 S Water St, Chestertown, MD 21620 - Photo 30 226 S Water St, Chestertown, MD 21620 - Photo 31 226 S Water St, Chestertown, MD 21620 - Photo 32
      Just Listed

      1/32

      226 S Water St  Chestertown, MD 21620

      $898,000
      • Townhouse
      • Active
      • MLS # MDKE2006354
      • Updated 6 days ago
      • 3
        Beds
      • 3
        Full Baths
      • 1
        Partial Bath
      • 4
        Total Baths
      • 2,172
        Sq. Ft.
      Listed by Gunther-McClary Real Estate, John J Burke and Gunther-McClary Real Estate, Julia Hilfiker

      Use previous and next buttons to navigate

      25475 Turnberry Ct, Chestertown, MD 21620 - Photo 1 25475 Turnberry Ct, Chestertown, MD 21620 - Photo 2 25475 Turnberry Ct, Chestertown, MD 21620 - Photo 3 25475 Turnberry Ct, Chestertown, MD 21620 - Photo 4 25475 Turnberry Ct, Chestertown, MD 21620 - Photo 5 25475 Turnberry Ct, Chestertown, MD 21620 - Photo 6 25475 Turnberry Ct, Chestertown, MD 21620 - Photo 7 25475 Turnberry Ct, Chestertown, MD 21620 - Photo 8 25475 Turnberry Ct, Chestertown, MD 21620 - Photo 9 25475 Turnberry Ct, Chestertown, MD 21620 - Photo 10 25475 Turnberry Ct, Chestertown, MD 21620 - Photo 11
      Coming Soon

      1/11

      Open House
      Sat4/1811-1

      25475 Turnberry Ct  Chestertown, MD 21620

      $867,000
      • Single Family
      • Coming Soon
      • MLS # MDKE2006350
      • Updated 7 days ago
      • 4
        Beds
      • 3
        Full Baths
      • 3
        Total Baths
      • 5,290
        Sq. Ft.
      • 5
        Car Garage
      Listed by Taylor Properties, Lona Sue Todd

      Use previous and next buttons to navigate

      720 Deep Landing Rd, Chestertown, MD 21620 - Photo 1 720 Deep Landing Rd, Chestertown, MD 21620 - Photo 2 720 Deep Landing Rd, Chestertown, MD 21620 - Photo 3 720 Deep Landing Rd, Chestertown, MD 21620 - Photo 4 720 Deep Landing Rd, Chestertown, MD 21620 - Photo 5 720 Deep Landing Rd, Chestertown, MD 21620 - Photo 6 720 Deep Landing Rd, Chestertown, MD 21620 - Photo 7 720 Deep Landing Rd, Chestertown, MD 21620 - Photo 8 720 Deep Landing Rd, Chestertown, MD 21620 - Photo 9 720 Deep Landing Rd, Chestertown, MD 21620 - Photo 10 720 Deep Landing Rd, Chestertown, MD 21620 - Photo 11 720 Deep Landing Rd, Chestertown, MD 21620 - Photo 12 720 Deep Landing Rd, Chestertown, MD 21620 - Photo 13 720 Deep Landing Rd, Chestertown, MD 21620 - Photo 14 720 Deep Landing Rd, Chestertown, MD 21620 - Photo 15 720 Deep Landing Rd, Chestertown, MD 21620 - Photo 16 720 Deep Landing Rd, Chestertown, MD 21620 - Photo 17 720 Deep Landing Rd, Chestertown, MD 21620 - Photo 18 720 Deep Landing Rd, Chestertown, MD 21620 - Photo 19 720 Deep Landing Rd, Chestertown, MD 21620 - Photo 20 720 Deep Landing Rd, Chestertown, MD 21620 - Photo 21 720 Deep Landing Rd, Chestertown, MD 21620 - Photo 22 720 Deep Landing Rd, Chestertown, MD 21620 - Photo 23 720 Deep Landing Rd, Chestertown, MD 21620 - Photo 24 720 Deep Landing Rd, Chestertown, MD 21620 - Photo 25 720 Deep Landing Rd, Chestertown, MD 21620 - Photo 26 720 Deep Landing Rd, Chestertown, MD 21620 - Photo 27 720 Deep Landing Rd, Chestertown, MD 21620 - Photo 28 720 Deep Landing Rd, Chestertown, MD 21620 - Photo 29 720 Deep Landing Rd, Chestertown, MD 21620 - Photo 30 720 Deep Landing Rd, Chestertown, MD 21620 - Photo 31 720 Deep Landing Rd, Chestertown, MD 21620 - Photo 32 720 Deep Landing Rd, Chestertown, MD 21620 - Photo 33 720 Deep Landing Rd, Chestertown, MD 21620 - Photo 34 720 Deep Landing Rd, Chestertown, MD 21620 - Photo 35 720 Deep Landing Rd, Chestertown, MD 21620 - Photo 36 720 Deep Landing Rd, Chestertown, MD 21620 - Photo 37 720 Deep Landing Rd, Chestertown, MD 21620 - Photo 38 720 Deep Landing Rd, Chestertown, MD 21620 - Photo 39 720 Deep Landing Rd, Chestertown, MD 21620 - Photo 40 720 Deep Landing Rd, Chestertown, MD 21620 - Photo 41 720 Deep Landing Rd, Chestertown, MD 21620 - Photo 42

      1/42

      720 Deep Landing Rd  Chestertown, MD 21620

      $369,999
      • Single Family
      • Active
      • MLS # MDQA2016758
      • Updated 4 days ago
      • 3
        Beds
      • 2
        Full Baths
      • 2
        Total Baths
      • 1,271
        Sq. Ft.
      • 2
        Car Garage
      Listed by Coldwell Banker Waterman Realty, Cornelia Fallon

      Use previous and next buttons to navigate

      136 Hilltop Dr, Chestertown, MD 21620 - Photo 1 136 Hilltop Dr, Chestertown, MD 21620 - Photo 2 136 Hilltop Dr, Chestertown, MD 21620 - Photo 3 136 Hilltop Dr, Chestertown, MD 21620 - Photo 4 136 Hilltop Dr, Chestertown, MD 21620 - Photo 5 136 Hilltop Dr, Chestertown, MD 21620 - Photo 6 136 Hilltop Dr, Chestertown, MD 21620 - Photo 7 136 Hilltop Dr, Chestertown, MD 21620 - Photo 8
      Coming Soon

      1/8

      136 Hilltop Dr  Chestertown, MD 21620

      $366,000
      • Single Family
      • Coming Soon
      • MLS # MDQA2016782
      • Updated 1 day ago
      • 3
        Beds
      • 2
        Full Baths
      • 2
        Total Baths
      • 1,432
        Sq. Ft.
      • 1
        Car Garage
      Listed by Northrop Realty, Joie L White

      Use previous and next buttons to navigate

      103 Sutton Way, Chestertown, MD 21620 - Photo 1 103 Sutton Way, Chestertown, MD 21620 - Photo 2 103 Sutton Way, Chestertown, MD 21620 - Photo 3 103 Sutton Way, Chestertown, MD 21620 - Photo 4 103 Sutton Way, Chestertown, MD 21620 - Photo 5 103 Sutton Way, Chestertown, MD 21620 - Photo 6 103 Sutton Way, Chestertown, MD 21620 - Photo 7 103 Sutton Way, Chestertown, MD 21620 - Photo 8 103 Sutton Way, Chestertown, MD 21620 - Photo 9 103 Sutton Way, Chestertown, MD 21620 - Photo 10 103 Sutton Way, Chestertown, MD 21620 - Photo 11 103 Sutton Way, Chestertown, MD 21620 - Photo 12 103 Sutton Way, Chestertown, MD 21620 - Photo 13 103 Sutton Way, Chestertown, MD 21620 - Photo 14 103 Sutton Way, Chestertown, MD 21620 - Photo 15 103 Sutton Way, Chestertown, MD 21620 - Photo 16 103 Sutton Way, Chestertown, MD 21620 - Photo 17 103 Sutton Way, Chestertown, MD 21620 - Photo 18 103 Sutton Way, Chestertown, MD 21620 - Photo 19 103 Sutton Way, Chestertown, MD 21620 - Photo 20 103 Sutton Way, Chestertown, MD 21620 - Photo 21 103 Sutton Way, Chestertown, MD 21620 - Photo 22 103 Sutton Way, Chestertown, MD 21620 - Photo 23 103 Sutton Way, Chestertown, MD 21620 - Photo 24 103 Sutton Way, Chestertown, MD 21620 - Photo 25 103 Sutton Way, Chestertown, MD 21620 - Photo 26 103 Sutton Way, Chestertown, MD 21620 - Photo 27 103 Sutton Way, Chestertown, MD 21620 - Photo 28 103 Sutton Way, Chestertown, MD 21620 - Photo 29 103 Sutton Way, Chestertown, MD 21620 - Photo 30 103 Sutton Way, Chestertown, MD 21620 - Photo 31 103 Sutton Way, Chestertown, MD 21620 - Photo 32 103 Sutton Way, Chestertown, MD 21620 - Photo 33 103 Sutton Way, Chestertown, MD 21620 - Photo 34 103 Sutton Way, Chestertown, MD 21620 - Photo 35 103 Sutton Way, Chestertown, MD 21620 - Photo 36 103 Sutton Way, Chestertown, MD 21620 - Photo 37 103 Sutton Way, Chestertown, MD 21620 - Photo 38 103 Sutton Way, Chestertown, MD 21620 - Photo 39 103 Sutton Way, Chestertown, MD 21620 - Photo 40 103 Sutton Way, Chestertown, MD 21620 - Photo 41 103 Sutton Way, Chestertown, MD 21620 - Photo 42 103 Sutton Way, Chestertown, MD 21620 - Photo 43 103 Sutton Way, Chestertown, MD 21620 - Photo 44 103 Sutton Way, Chestertown, MD 21620 - Photo 45 103 Sutton Way, Chestertown, MD 21620 - Photo 46 103 Sutton Way, Chestertown, MD 21620 - Photo 47 103 Sutton Way, Chestertown, MD 21620 - Photo 48 103 Sutton Way, Chestertown, MD 21620 - Photo 49 103 Sutton Way, Chestertown, MD 21620 - Photo 50 103 Sutton Way, Chestertown, MD 21620 - Photo 51 103 Sutton Way, Chestertown, MD 21620 - Photo 52 103 Sutton Way, Chestertown, MD 21620 - Photo 53

      1/53

      103 Sutton Way  Chestertown, MD 21620

      $550,000
      • Single Family
      • Active
      • MLS # MDKE2006344
      • Updated 11 days ago
      • 4
        Beds
      • 3
        Full Baths
      • 1
        Partial Bath
      • 4
        Total Baths
      • 4,170
        Sq. Ft.
      • 2
        Car Garage
      Listed by TTR Sotheby's International Realty, Liddy Campbell

      Use previous and next buttons to navigate

      107 Longfellow Dr, Chestertown, MD 21620 - Photo 1 107 Longfellow Dr, Chestertown, MD 21620 - Photo 2 107 Longfellow Dr, Chestertown, MD 21620 - Photo 3 107 Longfellow Dr, Chestertown, MD 21620 - Photo 4 107 Longfellow Dr, Chestertown, MD 21620 - Photo 5 107 Longfellow Dr, Chestertown, MD 21620 - Photo 6 107 Longfellow Dr, Chestertown, MD 21620 - Photo 7 107 Longfellow Dr, Chestertown, MD 21620 - Photo 8 107 Longfellow Dr, Chestertown, MD 21620 - Photo 9 107 Longfellow Dr, Chestertown, MD 21620 - Photo 10 107 Longfellow Dr, Chestertown, MD 21620 - Photo 11 107 Longfellow Dr, Chestertown, MD 21620 - Photo 12 107 Longfellow Dr, Chestertown, MD 21620 - Photo 13 107 Longfellow Dr, Chestertown, MD 21620 - Photo 14 107 Longfellow Dr, Chestertown, MD 21620 - Photo 15 107 Longfellow Dr, Chestertown, MD 21620 - Photo 16 107 Longfellow Dr, Chestertown, MD 21620 - Photo 17 107 Longfellow Dr, Chestertown, MD 21620 - Photo 18 107 Longfellow Dr, Chestertown, MD 21620 - Photo 19 107 Longfellow Dr, Chestertown, MD 21620 - Photo 20 107 Longfellow Dr, Chestertown, MD 21620 - Photo 21 107 Longfellow Dr, Chestertown, MD 21620 - Photo 22 107 Longfellow Dr, Chestertown, MD 21620 - Photo 23 107 Longfellow Dr, Chestertown, MD 21620 - Photo 24 107 Longfellow Dr, Chestertown, MD 21620 - Photo 25 107 Longfellow Dr, Chestertown, MD 21620 - Photo 26 107 Longfellow Dr, Chestertown, MD 21620 - Photo 27 107 Longfellow Dr, Chestertown, MD 21620 - Photo 28 107 Longfellow Dr, Chestertown, MD 21620 - Photo 29 107 Longfellow Dr, Chestertown, MD 21620 - Photo 30 107 Longfellow Dr, Chestertown, MD 21620 - Photo 31 107 Longfellow Dr, Chestertown, MD 21620 - Photo 32 107 Longfellow Dr, Chestertown, MD 21620 - Photo 33 107 Longfellow Dr, Chestertown, MD 21620 - Photo 34 107 Longfellow Dr, Chestertown, MD 21620 - Photo 35 107 Longfellow Dr, Chestertown, MD 21620 - Photo 36 107 Longfellow Dr, Chestertown, MD 21620 - Photo 37

      1/37

      107 Longfellow Dr  Chestertown, MD 21620

      $295,000
      • Single Family
      • Under Contract
      • MLS # MDQA2016720
      • Updated 5 hours ago
      • 3
        Beds
      • 1
        Full Bath
      • 1
        Total Bath
      • 3
        Car Garage
      Listed by Doug Ashley Realtors, LLC, Douglas J Ashley

      Use previous and next buttons to navigate

      106 Queen Street S, Chestertown, MD 21620 - Photo 1 106 Queen Street S, Chestertown, MD 21620 - Photo 2 106 Queen Street S, Chestertown, MD 21620 - Photo 3 106 Queen Street S, Chestertown, MD 21620 - Photo 4 106 Queen Street S, Chestertown, MD 21620 - Photo 5 106 Queen Street S, Chestertown, MD 21620 - Photo 6 106 Queen Street S, Chestertown, MD 21620 - Photo 7 106 Queen Street S, Chestertown, MD 21620 - Photo 8 106 Queen Street S, Chestertown, MD 21620 - Photo 9 106 Queen Street S, Chestertown, MD 21620 - Photo 10 106 Queen Street S, Chestertown, MD 21620 - Photo 11 106 Queen Street S, Chestertown, MD 21620 - Photo 12 106 Queen Street S, Chestertown, MD 21620 - Photo 13 106 Queen Street S, Chestertown, MD 21620 - Photo 14 106 Queen Street S, Chestertown, MD 21620 - Photo 15 106 Queen Street S, Chestertown, MD 21620 - Photo 16 106 Queen Street S, Chestertown, MD 21620 - Photo 17 106 Queen Street S, Chestertown, MD 21620 - Photo 18 106 Queen Street S, Chestertown, MD 21620 - Photo 19 106 Queen Street S, Chestertown, MD 21620 - Photo 20 106 Queen Street S, Chestertown, MD 21620 - Photo 21 106 Queen Street S, Chestertown, MD 21620 - Photo 22 106 Queen Street S, Chestertown, MD 21620 - Photo 23 106 Queen Street S, Chestertown, MD 21620 - Photo 24 106 Queen Street S, Chestertown, MD 21620 - Photo 25 106 Queen Street S, Chestertown, MD 21620 - Photo 26 106 Queen Street S, Chestertown, MD 21620 - Photo 27 106 Queen Street S, Chestertown, MD 21620 - Photo 28 106 Queen Street S, Chestertown, MD 21620 - Photo 29 106 Queen Street S, Chestertown, MD 21620 - Photo 30 106 Queen Street S, Chestertown, MD 21620 - Photo 31 106 Queen Street S, Chestertown, MD 21620 - Photo 32 106 Queen Street S, Chestertown, MD 21620 - Photo 33 106 Queen Street S, Chestertown, MD 21620 - Photo 34 106 Queen Street S, Chestertown, MD 21620 - Photo 35 106 Queen Street S, Chestertown, MD 21620 - Photo 36 106 Queen Street S, Chestertown, MD 21620 - Photo 37 106 Queen Street S, Chestertown, MD 21620 - Photo 38 106 Queen Street S, Chestertown, MD 21620 - Photo 39 106 Queen Street S, Chestertown, MD 21620 - Photo 40 106 Queen Street S, Chestertown, MD 21620 - Photo 41 106 Queen Street S, Chestertown, MD 21620 - Photo 42 106 Queen Street S, Chestertown, MD 21620 - Photo 43 106 Queen Street S, Chestertown, MD 21620 - Photo 44 106 Queen Street S, Chestertown, MD 21620 - Photo 45 106 Queen Street S, Chestertown, MD 21620 - Photo 46 106 Queen Street S, Chestertown, MD 21620 - Photo 47 106 Queen Street S, Chestertown, MD 21620 - Photo 48 106 Queen Street S, Chestertown, MD 21620 - Photo 49 106 Queen Street S, Chestertown, MD 21620 - Photo 50 106 Queen Street S, Chestertown, MD 21620 - Photo 51 106 Queen Street S, Chestertown, MD 21620 - Photo 52 106 Queen Street S, Chestertown, MD 21620 - Photo 53 106 Queen Street S, Chestertown, MD 21620 - Photo 54 106 Queen Street S, Chestertown, MD 21620 - Photo 55 106 Queen Street S, Chestertown, MD 21620 - Photo 56 106 Queen Street S, Chestertown, MD 21620 - Photo 57 106 Queen Street S, Chestertown, MD 21620 - Photo 58 106 Queen Street S, Chestertown, MD 21620 - Photo 59 106 Queen Street S, Chestertown, MD 21620 - Photo 60 106 Queen Street S, Chestertown, MD 21620 - Photo 61 106 Queen Street S, Chestertown, MD 21620 - Photo 62 106 Queen Street S, Chestertown, MD 21620 - Photo 63 106 Queen Street S, Chestertown, MD 21620 - Photo 64 106 Queen Street S, Chestertown, MD 21620 - Photo 65 106 Queen Street S, Chestertown, MD 21620 - Photo 66 106 Queen Street S, Chestertown, MD 21620 - Photo 67 106 Queen Street S, Chestertown, MD 21620 - Photo 68 106 Queen Street S, Chestertown, MD 21620 - Photo 69 106 Queen Street S, Chestertown, MD 21620 - Photo 70

      1/70

      106 Queen Street S  Chestertown, MD 21620

      $865,000
      • Single Family
      • Active
      • MLS # MDKE2006152
      • Updated 12 days ago
      • 3
        Beds
      • 3
        Full Baths
      • 1
        Partial Bath
      • 4
        Total Baths
      • 2,472
        Sq. Ft.
      • 1
        Car Garage
      Listed by Chesapeake Real Estate Associates, LLC, Maryn J. LeClair

      Use previous and next buttons to navigate

      704 Truslow Rd, Chestertown, MD 21620 - Photo 1 704 Truslow Rd, Chestertown, MD 21620 - Photo 2 704 Truslow Rd, Chestertown, MD 21620 - Photo 3 704 Truslow Rd, Chestertown, MD 21620 - Photo 4 704 Truslow Rd, Chestertown, MD 21620 - Photo 5 704 Truslow Rd, Chestertown, MD 21620 - Photo 6 704 Truslow Rd, Chestertown, MD 21620 - Photo 7 704 Truslow Rd, Chestertown, MD 21620 - Photo 8 704 Truslow Rd, Chestertown, MD 21620 - Photo 9 704 Truslow Rd, Chestertown, MD 21620 - Photo 10 704 Truslow Rd, Chestertown, MD 21620 - Photo 11 704 Truslow Rd, Chestertown, MD 21620 - Photo 12 704 Truslow Rd, Chestertown, MD 21620 - Photo 13 704 Truslow Rd, Chestertown, MD 21620 - Photo 14 704 Truslow Rd, Chestertown, MD 21620 - Photo 15 704 Truslow Rd, Chestertown, MD 21620 - Photo 16 704 Truslow Rd, Chestertown, MD 21620 - Photo 17 704 Truslow Rd, Chestertown, MD 21620 - Photo 18 704 Truslow Rd, Chestertown, MD 21620 - Photo 19 704 Truslow Rd, Chestertown, MD 21620 - Photo 20 704 Truslow Rd, Chestertown, MD 21620 - Photo 21 704 Truslow Rd, Chestertown, MD 21620 - Photo 22 704 Truslow Rd, Chestertown, MD 21620 - Photo 23 704 Truslow Rd, Chestertown, MD 21620 - Photo 24 704 Truslow Rd, Chestertown, MD 21620 - Photo 25 704 Truslow Rd, Chestertown, MD 21620 - Photo 26 704 Truslow Rd, Chestertown, MD 21620 - Photo 27 704 Truslow Rd, Chestertown, MD 21620 - Photo 28 704 Truslow Rd, Chestertown, MD 21620 - Photo 29 704 Truslow Rd, Chestertown, MD 21620 - Photo 30 704 Truslow Rd, Chestertown, MD 21620 - Photo 31 704 Truslow Rd, Chestertown, MD 21620 - Photo 32 704 Truslow Rd, Chestertown, MD 21620 - Photo 33 704 Truslow Rd, Chestertown, MD 21620 - Photo 34 704 Truslow Rd, Chestertown, MD 21620 - Photo 35 704 Truslow Rd, Chestertown, MD 21620 - Photo 36 704 Truslow Rd, Chestertown, MD 21620 - Photo 37 704 Truslow Rd, Chestertown, MD 21620 - Photo 38 704 Truslow Rd, Chestertown, MD 21620 - Photo 39 704 Truslow Rd, Chestertown, MD 21620 - Photo 40 704 Truslow Rd, Chestertown, MD 21620 - Photo 41 704 Truslow Rd, Chestertown, MD 21620 - Photo 42 704 Truslow Rd, Chestertown, MD 21620 - Photo 43

      1/43

      704 Truslow Rd  Chestertown, MD 21620

      $440,000
      • Single Family
      • Active
      • MLS # MDQA2016632
      • Updated 8 days ago
      • 3
        Beds
      • 2
        Full Baths
      • 1
        Partial Bath
      • 3
        Total Baths
      • 2,060
        Sq. Ft.
      • 2
        Car Garage
      Listed by RE/MAX Executive, Crystal M Smith

      Use previous and next buttons to navigate

      104 Flying Cloud Dr, Chestertown, MD 21620 - Photo 1 104 Flying Cloud Dr, Chestertown, MD 21620 - Photo 2 104 Flying Cloud Dr, Chestertown, MD 21620 - Photo 3 104 Flying Cloud Dr, Chestertown, MD 21620 - Photo 4 104 Flying Cloud Dr, Chestertown, MD 21620 - Photo 5 104 Flying Cloud Dr, Chestertown, MD 21620 - Photo 6 104 Flying Cloud Dr, Chestertown, MD 21620 - Photo 7 104 Flying Cloud Dr, Chestertown, MD 21620 - Photo 8 104 Flying Cloud Dr, Chestertown, MD 21620 - Photo 9 104 Flying Cloud Dr, Chestertown, MD 21620 - Photo 10 104 Flying Cloud Dr, Chestertown, MD 21620 - Photo 11 104 Flying Cloud Dr, Chestertown, MD 21620 - Photo 12 104 Flying Cloud Dr, Chestertown, MD 21620 - Photo 13 104 Flying Cloud Dr, Chestertown, MD 21620 - Photo 14 104 Flying Cloud Dr, Chestertown, MD 21620 - Photo 15 104 Flying Cloud Dr, Chestertown, MD 21620 - Photo 16 104 Flying Cloud Dr, Chestertown, MD 21620 - Photo 17 104 Flying Cloud Dr, Chestertown, MD 21620 - Photo 18 104 Flying Cloud Dr, Chestertown, MD 21620 - Photo 19 104 Flying Cloud Dr, Chestertown, MD 21620 - Photo 20 104 Flying Cloud Dr, Chestertown, MD 21620 - Photo 21 104 Flying Cloud Dr, Chestertown, MD 21620 - Photo 22 104 Flying Cloud Dr, Chestertown, MD 21620 - Photo 23 104 Flying Cloud Dr, Chestertown, MD 21620 - Photo 24 104 Flying Cloud Dr, Chestertown, MD 21620 - Photo 25 104 Flying Cloud Dr, Chestertown, MD 21620 - Photo 26 104 Flying Cloud Dr, Chestertown, MD 21620 - Photo 27 104 Flying Cloud Dr, Chestertown, MD 21620 - Photo 28 104 Flying Cloud Dr, Chestertown, MD 21620 - Photo 29 104 Flying Cloud Dr, Chestertown, MD 21620 - Photo 30 104 Flying Cloud Dr, Chestertown, MD 21620 - Photo 31

      1/31

      104 Flying Cloud Dr  Chestertown, MD 21620

      $399,900
      • Single Family
      • Active
      • MLS # MDKE2006212
      • Updated 12 days ago
      • 5
        Beds
      • 3
        Full Baths
      • 1
        Partial Bath
      • 4
        Total Baths
      • 2,535
        Sq. Ft.
      Listed by Real Broker, LLC, David J. J Moore

      Use previous and next buttons to navigate

      108 Pine St, Chestertown, MD 21620 - Photo 1
      Sale Pending

      1/1

      108 Pine St  Chestertown, MD 21620

      $115,000
      • Single Family
      • Pending
      • MLS # MDKE2006322
      • Updated 6 days ago
      • 3
        Beds
      • 1
        Full Bath
      • 1
        Total Bath
      • 910
        Sq. Ft.
      Listed by Real Broker, LLC, David J. J Moore

      Use previous and next buttons to navigate

      217 Philosophers Terrace, Chestertown, MD 21620 - Photo 1 217 Philosophers Terrace, Chestertown, MD 21620 - Photo 2 217 Philosophers Terrace, Chestertown, MD 21620 - Photo 3 217 Philosophers Terrace, Chestertown, MD 21620 - Photo 4 217 Philosophers Terrace, Chestertown, MD 21620 - Photo 5 217 Philosophers Terrace, Chestertown, MD 21620 - Photo 6 217 Philosophers Terrace, Chestertown, MD 21620 - Photo 7 217 Philosophers Terrace, Chestertown, MD 21620 - Photo 8 217 Philosophers Terrace, Chestertown, MD 21620 - Photo 9 217 Philosophers Terrace, Chestertown, MD 21620 - Photo 10 217 Philosophers Terrace, Chestertown, MD 21620 - Photo 11 217 Philosophers Terrace, Chestertown, MD 21620 - Photo 12 217 Philosophers Terrace, Chestertown, MD 21620 - Photo 13 217 Philosophers Terrace, Chestertown, MD 21620 - Photo 14 217 Philosophers Terrace, Chestertown, MD 21620 - Photo 15 217 Philosophers Terrace, Chestertown, MD 21620 - Photo 16 217 Philosophers Terrace, Chestertown, MD 21620 - Photo 17 217 Philosophers Terrace, Chestertown, MD 21620 - Photo 18 217 Philosophers Terrace, Chestertown, MD 21620 - Photo 19 217 Philosophers Terrace, Chestertown, MD 21620 - Photo 20 217 Philosophers Terrace, Chestertown, MD 21620 - Photo 21 217 Philosophers Terrace, Chestertown, MD 21620 - Photo 22 217 Philosophers Terrace, Chestertown, MD 21620 - Photo 23 217 Philosophers Terrace, Chestertown, MD 21620 - Photo 24 217 Philosophers Terrace, Chestertown, MD 21620 - Photo 25

      1/25

      217 Philosophers Terrace  Chestertown, MD 21620

      $325,000
      • Single Family
      • Under Contract
      • MLS # MDKE2006332
      • Updated 10 days ago
      • 3
        Beds
      • 1
        Full Bath
      • 1
        Partial Bath
      • 2
        Total Baths
      • 1,404
        Sq. Ft.
      • 1
        Car Garage
      Listed by TTR Sotheby's International Realty, Courtney Chipouras

      Use previous and next buttons to navigate

      10584 Klamath Rd, Chestertown, MD 21620 - Photo 1 10584 Klamath Rd, Chestertown, MD 21620 - Photo 2 10584 Klamath Rd, Chestertown, MD 21620 - Photo 3 10584 Klamath Rd, Chestertown, MD 21620 - Photo 4 10584 Klamath Rd, Chestertown, MD 21620 - Photo 5 10584 Klamath Rd, Chestertown, MD 21620 - Photo 6 10584 Klamath Rd, Chestertown, MD 21620 - Photo 7 10584 Klamath Rd, Chestertown, MD 21620 - Photo 8 10584 Klamath Rd, Chestertown, MD 21620 - Photo 9 10584 Klamath Rd, Chestertown, MD 21620 - Photo 10 10584 Klamath Rd, Chestertown, MD 21620 - Photo 11 10584 Klamath Rd, Chestertown, MD 21620 - Photo 12 10584 Klamath Rd, Chestertown, MD 21620 - Photo 13 10584 Klamath Rd, Chestertown, MD 21620 - Photo 14 10584 Klamath Rd, Chestertown, MD 21620 - Photo 15 10584 Klamath Rd, Chestertown, MD 21620 - Photo 16 10584 Klamath Rd, Chestertown, MD 21620 - Photo 17 10584 Klamath Rd, Chestertown, MD 21620 - Photo 18 10584 Klamath Rd, Chestertown, MD 21620 - Photo 19 10584 Klamath Rd, Chestertown, MD 21620 - Photo 20
      Coming Soon

      1/20

      10584 Klamath Rd  Chestertown, MD 21620

      $319,900
      • Single Family
      • Coming Soon
      • MLS # MDKE2006328
      • Updated 1 day ago
      • 2
        Beds
      • 2
        Full Baths
      • 2
        Total Baths
      Listed by Real Broker, LLC, David J. J Moore

      Use previous and next buttons to navigate

      201 Birch Run Rd, Chestertown, MD 21620 - Photo 1 201 Birch Run Rd, Chestertown, MD 21620 - Photo 2 201 Birch Run Rd, Chestertown, MD 21620 - Photo 3 201 Birch Run Rd, Chestertown, MD 21620 - Photo 4 201 Birch Run Rd, Chestertown, MD 21620 - Photo 5 201 Birch Run Rd, Chestertown, MD 21620 - Photo 6 201 Birch Run Rd, Chestertown, MD 21620 - Photo 7 201 Birch Run Rd, Chestertown, MD 21620 - Photo 8 201 Birch Run Rd, Chestertown, MD 21620 - Photo 9 201 Birch Run Rd, Chestertown, MD 21620 - Photo 10 201 Birch Run Rd, Chestertown, MD 21620 - Photo 11 201 Birch Run Rd, Chestertown, MD 21620 - Photo 12 201 Birch Run Rd, Chestertown, MD 21620 - Photo 13 201 Birch Run Rd, Chestertown, MD 21620 - Photo 14 201 Birch Run Rd, Chestertown, MD 21620 - Photo 15 201 Birch Run Rd, Chestertown, MD 21620 - Photo 16 201 Birch Run Rd, Chestertown, MD 21620 - Photo 17 201 Birch Run Rd, Chestertown, MD 21620 - Photo 18 201 Birch Run Rd, Chestertown, MD 21620 - Photo 19 201 Birch Run Rd, Chestertown, MD 21620 - Photo 20 201 Birch Run Rd, Chestertown, MD 21620 - Photo 21 201 Birch Run Rd, Chestertown, MD 21620 - Photo 22 201 Birch Run Rd, Chestertown, MD 21620 - Photo 23 201 Birch Run Rd, Chestertown, MD 21620 - Photo 24

      1/24

      201 Birch Run Rd  Chestertown, MD 21620

      $435,000
      • Single Family
      • Active
      • MLS # MDKE2006316
      • 3
        Beds
      • 2
        Full Baths
      • 2
        Total Baths
      • 1,588
        Sq. Ft.
      • 2
        Car Garage
      Listed by Coldwell Banker Chesapeake Real Estate Company, Michael ONeill

      Use previous and next buttons to navigate

      101 Coleman Dr, Chestertown, MD 21620 - Photo 1 101 Coleman Dr, Chestertown, MD 21620 - Photo 2 101 Coleman Dr, Chestertown, MD 21620 - Photo 3 101 Coleman Dr, Chestertown, MD 21620 - Photo 4 101 Coleman Dr, Chestertown, MD 21620 - Photo 5 101 Coleman Dr, Chestertown, MD 21620 - Photo 6 101 Coleman Dr, Chestertown, MD 21620 - Photo 7 101 Coleman Dr, Chestertown, MD 21620 - Photo 8 101 Coleman Dr, Chestertown, MD 21620 - Photo 9 101 Coleman Dr, Chestertown, MD 21620 - Photo 10 101 Coleman Dr, Chestertown, MD 21620 - Photo 11 101 Coleman Dr, Chestertown, MD 21620 - Photo 12 101 Coleman Dr, Chestertown, MD 21620 - Photo 13 101 Coleman Dr, Chestertown, MD 21620 - Photo 14 101 Coleman Dr, Chestertown, MD 21620 - Photo 15 101 Coleman Dr, Chestertown, MD 21620 - Photo 16 101 Coleman Dr, Chestertown, MD 21620 - Photo 17 101 Coleman Dr, Chestertown, MD 21620 - Photo 18 101 Coleman Dr, Chestertown, MD 21620 - Photo 19 101 Coleman Dr, Chestertown, MD 21620 - Photo 20 101 Coleman Dr, Chestertown, MD 21620 - Photo 21 101 Coleman Dr, Chestertown, MD 21620 - Photo 22 101 Coleman Dr, Chestertown, MD 21620 - Photo 23 101 Coleman Dr, Chestertown, MD 21620 - Photo 24 101 Coleman Dr, Chestertown, MD 21620 - Photo 25 101 Coleman Dr, Chestertown, MD 21620 - Photo 26 101 Coleman Dr, Chestertown, MD 21620 - Photo 27 101 Coleman Dr, Chestertown, MD 21620 - Photo 28 101 Coleman Dr, Chestertown, MD 21620 - Photo 29 101 Coleman Dr, Chestertown, MD 21620 - Photo 30 101 Coleman Dr, Chestertown, MD 21620 - Photo 31 101 Coleman Dr, Chestertown, MD 21620 - Photo 32 101 Coleman Dr, Chestertown, MD 21620 - Photo 33 101 Coleman Dr, Chestertown, MD 21620 - Photo 34 101 Coleman Dr, Chestertown, MD 21620 - Photo 35 101 Coleman Dr, Chestertown, MD 21620 - Photo 36 101 Coleman Dr, Chestertown, MD 21620 - Photo 37 101 Coleman Dr, Chestertown, MD 21620 - Photo 38 101 Coleman Dr, Chestertown, MD 21620 - Photo 39 101 Coleman Dr, Chestertown, MD 21620 - Photo 40 101 Coleman Dr, Chestertown, MD 21620 - Photo 41 101 Coleman Dr, Chestertown, MD 21620 - Photo 42 101 Coleman Dr, Chestertown, MD 21620 - Photo 43 101 Coleman Dr, Chestertown, MD 21620 - Photo 44 101 Coleman Dr, Chestertown, MD 21620 - Photo 45 101 Coleman Dr, Chestertown, MD 21620 - Photo 46 101 Coleman Dr, Chestertown, MD 21620 - Photo 47 101 Coleman Dr, Chestertown, MD 21620 - Photo 48 101 Coleman Dr, Chestertown, MD 21620 - Photo 49 101 Coleman Dr, Chestertown, MD 21620 - Photo 50 101 Coleman Dr, Chestertown, MD 21620 - Photo 51 101 Coleman Dr, Chestertown, MD 21620 - Photo 52 101 Coleman Dr, Chestertown, MD 21620 - Photo 53 101 Coleman Dr, Chestertown, MD 21620 - Photo 54 101 Coleman Dr, Chestertown, MD 21620 - Photo 55 101 Coleman Dr, Chestertown, MD 21620 - Photo 56

      1/56

      101 Coleman Dr  Chestertown, MD 21620

      $524,900
      • Single Family
      • Active
      • MLS # MDQA2016624
      • 3
        Beds
      • 2
        Full Baths
      • 1
        Partial Bath
      • 3
        Total Baths
      • 2,268
        Sq. Ft.
      • 2
        Car Garage
      Listed by Coldwell Banker Chesapeake Real Estate Company, Terri L Kulp

      Use previous and next buttons to navigate

      103 Flying Cloud Dr, Chestertown, MD 21620 - Photo 1
      Sale Pending

      1/1

      103 Flying Cloud Dr  Chestertown, MD 21620

      $339,900
      • Single Family
      • Pending
      • MLS # MDKE2006154
      • 3
        Beds
      • 2
        Full Baths
      • 1
        Partial Bath
      • 3
        Total Baths
      • 1,724
        Sq. Ft.
      Listed by American Premier Realty, LLC, Laura M Snyder

      Use previous and next buttons to navigate

      139 Prospect St, Chestertown, MD 21620 - Photo 1 139 Prospect St, Chestertown, MD 21620 - Photo 2 139 Prospect St, Chestertown, MD 21620 - Photo 3 139 Prospect St, Chestertown, MD 21620 - Photo 4 139 Prospect St, Chestertown, MD 21620 - Photo 5 139 Prospect St, Chestertown, MD 21620 - Photo 6 139 Prospect St, Chestertown, MD 21620 - Photo 7 139 Prospect St, Chestertown, MD 21620 - Photo 8 139 Prospect St, Chestertown, MD 21620 - Photo 9 139 Prospect St, Chestertown, MD 21620 - Photo 10 139 Prospect St, Chestertown, MD 21620 - Photo 11 139 Prospect St, Chestertown, MD 21620 - Photo 12 139 Prospect St, Chestertown, MD 21620 - Photo 13 139 Prospect St, Chestertown, MD 21620 - Photo 14 139 Prospect St, Chestertown, MD 21620 - Photo 15 139 Prospect St, Chestertown, MD 21620 - Photo 16 139 Prospect St, Chestertown, MD 21620 - Photo 17 139 Prospect St, Chestertown, MD 21620 - Photo 18 139 Prospect St, Chestertown, MD 21620 - Photo 19 139 Prospect St, Chestertown, MD 21620 - Photo 20 139 Prospect St, Chestertown, MD 21620 - Photo 21 139 Prospect St, Chestertown, MD 21620 - Photo 22 139 Prospect St, Chestertown, MD 21620 - Photo 23 139 Prospect St, Chestertown, MD 21620 - Photo 24 139 Prospect St, Chestertown, MD 21620 - Photo 25 139 Prospect St, Chestertown, MD 21620 - Photo 26 139 Prospect St, Chestertown, MD 21620 - Photo 27 139 Prospect St, Chestertown, MD 21620 - Photo 28

      1/28

      139 Prospect St  Chestertown, MD 21620

      $225,000
      • Single Family
      • Active
      • MLS # MDKE2006250
      • 3
        Beds
      • 1
        Full Bath
      • 1
        Total Bath
      • 1,200
        Sq. Ft.
      Listed by Redfin Corp, Barbara A McCaffrey

      Save this searchYou’ll get email updates when new properties matching this criteria go on the market. You can also run these searches quickly under “Properties & Searches” at the top of every page. and receive alerts when new properties are listed.

      Find Real Estate in Chestertown, MD

      Coldwell Banker Realty can help you find Chestertown homes for sale, rentals and open houses. Refine your Chestertown real estate search results by price, property type, bedrooms, baths and other features. Need more information? View our Chestertown real estate offices and let us help you find the perfect property.

      School attendance boundaries provided by ATTOM Data Solutions and are for reference only. Contact the school directly to verify enrollment eligibility.

      Assurant Home Warranty logo

      Protect your home and budget from life’s surprises with an Assurant Home Warranty, backed by a partner that supports you through every step of homeownership. Explore Plans

      Coldwell Banker Realty and Guaranteed Rate Affinity, LLC share common ownership and because of this relationship the brokerage may receive a financial or other benefit. You are not required to use Guaranteed Rate Affinity, LLC as a condition of purchase or sale of any real estate. Operating in the state of New York as GR Affinity, LLC in lieu of the legal name Guaranteed Rate Affinity, LLC.

      Real estate agents affiliated with Coldwell Banker are independent contractor sales associates and are not employees of Coldwell Banker.

      © 2026 Coldwell Banker. All Rights Reserved. Coldwell Banker and the Coldwell Banker logos are trademarks of Coldwell Banker Real Estate LLC. The Coldwell Banker® System is comprised of company owned offices which are owned by a subsidiary of Anywhere Advisors LLC and franchised offices which are independently owned and operated. The Coldwell Banker System fully supports the principles of the Fair Housing Act and the Equal Opportunity Act.

      Search options

      We can’t map any of the properties in your results.