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    • Forest Knolls West at Ragged Mountain Resort
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    • Waterscapes at Owl's Nest Resort
  • Regions
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      • Lake Sunapee Region
      • Lakes Region
      • Monadnock Region
      • Southern New Hampshire
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      • The Adirondacks
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      • Southface Village at Okemo
      • Stonewall Glen at Windham Mountain Club
      • Waterscapes at Owl's Nest Resort
    • Regions
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        • Lake Sunapee Region
        • Lakes Region
        • Monadnock Region
        • Southern New Hampshire
        • Upper Valley of New Hampshire
        • White Mountains
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        • The Adirondacks
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Properties for Sale In Chestertown NY

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Viewing 13-24 of 48 listings
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    • Open House
    • Price Reduced
    • New Listing
    • Pending
    • Coming Soon
    • virtual Tour
    • Sold
    • Leased
    16 B Evergreen Road, Chestertown, NY
    $275,000
    $275,000
    MLS# 202514261Condo/Townhouse
    1,248 Sq. Ft.
     
    3 BEDS 2 BATH 2 BATHS
    Request Info
    Details
    View Photos of 16 B Evergreen Road, Chestertown, NY 12817
    16 B Evergreen Road https://selectsothebysrealty.com/condo-townhouse/glb/202514261/16-b-evergreen-road-chestertown-ny-12817 https://cdn.datafloat.com/FOS_PUBLIC/MLSPhotos/GLBCMN/202514261_1.jpg
    275000 USD
    Chestertown VT 12817
    43.5962 -73.79231
      • Open House
      • Price Reduced
      • New Listing
      • Pending
      • Coming Soon
      • virtual Tour
      • Sold
      • Leased
      64 Carriage Knolls Road, Chestertown, NY
      $70,000
      $70,000
      MLS# 202514265Land
      Sq. Ft.
       
      0 BEDS BATH BATHS
      Request Info
      Details
      View Photos of 64 Carriage Knolls Road, Chestertown, NY 12817
      64 Carriage Knolls Road https://selectsothebysrealty.com/land/glb/202514265/64-carriage-knolls-road-chestertown-ny-12817 https://cdn.datafloat.com/FOS_PUBLIC/MLSPhotos/GLBCMN/202514265_1.jpg
      70000 USD
      Chestertown VT 12817
      43.66867 -73.79417
        • Open House
        • Price Reduced $24,900
        • New Listing
        • Pending
        • Coming Soon
        • virtual Tour
        • Sold
        • Leased
        51 Mountain Lane, Chestertown, NY
        $275,000
        $275,000
        MLS# 202513647Land
        Sq. Ft.
         
        0 BEDS BATH BATHS
        Request Info
        Details
        View Photos of 51 Mountain Lane, Chestertown, NY 12885
        51 Mountain Lane https://selectsothebysrealty.com/land/glb/202513647/51-mountain-lane-chestertown-ny-12885 https://cdn.datafloat.com/FOS_PUBLIC/MLSPhotos/GLBCMN/202513647_1.jpg
        275000 USD
        Chestertown VT 12885
        43.60011 -73.79509
          • Open House
          • Price Reduced
          • New Listing
          • Pending
          • Coming Soon
          • virtual Tour
          • Sold
          • Leased
          4785 NY-8, Chestertown, NY
          $374,900
          $374,900
          MLS# 202512867Residential
          1,196 Sq. Ft.
           
          3 BEDS 2 BATH 2 BATHS
          Request Info
          Details
          View Photos of 4785 NY-8, Chestertown, NY 12817
          4785 NY-8 https://selectsothebysrealty.com/residential/glb/202512867/4785-ny-8-chestertown-ny-12817 https://cdn.datafloat.com/FOS_PUBLIC/MLSPhotos/GLBCMN/202512867_1.jpg
          374900 USD
          Chestertown VT 12817
          43.66178 -73.8888
            • Open House
            • Price Reduced $10,000
            • New Listing
            • Pending
            • Coming Soon
            • virtual Tour
            • Sold
            • Leased
            5127 State Route 8, Chestertown, NY
            $105,000
            $105,000
            MLS# 202512224Land
            Sq. Ft.
             
            0 BEDS BATH BATHS
            Request Info
            Details
            View Photos of 5127 State Route 8, Chestertown, NY 12817
            5127 State Route 8 https://selectsothebysrealty.com/land/glb/202512224/5127-state-route-8-chestertown-ny-12817 https://cdn.datafloat.com/FOS_PUBLIC/MLSPhotos/GLBCMN/202512224_1.jpg
            105000 USD
            Chestertown VT 12817
            43.66811 -73.86042
              • Open House
              • Price Reduced $4,000
              • New Listing
              • Pending
              • Coming Soon
              • virtual Tour
              • Sold
              • Leased
              6404 Route 9, Chestertown, NY
              $245,900
              $245,900
              MLS# 202510964Residential
              1,500 Sq. Ft.
               
              1 BEDS 2 BATH 2 BATHS
              Request Info
              Details
              View Photos of 6404 Route 9, Chestertown, NY 12817
              6404 Route 9 https://selectsothebysrealty.com/residential/glb/202510964/6404-route-9-chestertown-ny-12817 https://cdn.datafloat.com/FOS_PUBLIC/MLSPhotos/GLBCMN/202510964_1.jpg
              245900 USD
              Chestertown VT 12817
              43.65541 -73.8009
                • Open House
                • Price Reduced $25,000
                • New Listing
                • Pending
                • Coming Soon
                • virtual Tour
                • Sold
                • Leased
                1007 Friends Lake Road, Chestertown, NY
                $350,000
                $350,000
                MLS# 202430393Residential
                1,166 Sq. Ft.
                 
                5 BEDS 3 BATH 3 BATHS
                Request Info
                Details
                View Photos of 1007 Friends Lake Road, Chestertown, NY 12817
                1007 Friends Lake Road https://selectsothebysrealty.com/residential/glb/202430393/1007-friends-lake-road-chestertown-ny-12817 https://cdn.datafloat.com/FOS_PUBLIC/MLSPhotos/GLBCMN/202430393_1.jpg
                350000 USD
                Chestertown VT 12817
                43.64206 -73.84827
                  • Open House
                  • Price Reduced $5,000
                  • New Listing
                  • Pending
                  • Coming Soon
                  • virtual Tour
                  • Sold
                  • Leased
                  68 Woodridge Road, Chestertown, NY
                  $364,900
                  $364,900
                  MLS# 202430157Residential
                  1,120 Sq. Ft.
                   
                  2 BEDS 1 BATH 1 BATHS
                  Request Info
                  Details
                  View Photos of 68 Woodridge Road, Chestertown, NY 12817
                  68 Woodridge Road https://selectsothebysrealty.com/residential/glb/202430157/68-woodridge-road-chestertown-ny-12817 https://cdn.datafloat.com/FOS_PUBLIC/MLSPhotos/GLBCMN/202430157_1.jpg
                  364900 USD
                  Chestertown VT 12817
                  43.64288 -73.79575
                    • Open House
                    • Price Reduced
                    • New Listing
                    • Pending
                    • Coming Soon
                    • virtual Tour
                    • Sold
                    • Leased
                    L37 Blue Bay Road #Lakeview Pt. Lot 40, Chestertown, NY
                    $57,500
                    $57,500
                    MLS# 202429475Land
                    Sq. Ft.
                     
                    0 BEDS BATH BATHS
                    Request Info
                    Details
                    View Photos of L37 Blue Bay Road #Lakeview Pt. Lot 40, Chestertown, NY 12817
                    L37 Blue Bay Road #Lakeview Pt. Lot 40 https://selectsothebysrealty.com/land/glb/202429475/l37-blue-bay-road-lakeview-pt.-lot-40-chestertown-ny-12817 https://cdn.datafloat.com/FOS_PUBLIC/MLSPhotos/GLBCMN/202429475_1.jpg
                    57500 USD
                    Chestertown VT 12817
                    43.67115 -73.86167
                      • Open House
                      • Price Reduced $14,000
                      • New Listing
                      • Pending
                      • Coming Soon
                      • virtual Tour
                      • Sold
                      • Leased
                      106 Carriage Knoll Road, Chestertown, NY
                      $78,900
                      $78,900
                      MLS# 202427760Land
                      Sq. Ft.
                       
                      0 BEDS BATH BATHS
                      Request Info
                      Details
                      View Photos of 106 Carriage Knoll Road, Chestertown, NY 12817
                      106 Carriage Knoll Road https://selectsothebysrealty.com/land/glb/202427760/106-carriage-knoll-road-chestertown-ny-12817 https://cdn.datafloat.com/FOS_PUBLIC/MLSPhotos/GLBCMN/202427760_1.jpg
                      78900 USD
                      Chestertown VT 12817
                      43.66629 -73.79453
                        • Open House
                        • Price Reduced $14,400
                        • New Listing
                        • Pending
                        • Coming Soon
                        • virtual Tour
                        • Sold
                        • Leased
                        112 Carriage Knoll Road, Chestertown, NY
                        $76,900
                        $76,900
                        MLS# 202427761Land
                        Sq. Ft.
                         
                        0 BEDS BATH BATHS
                        Request Info
                        Details
                        View Photos of 112 Carriage Knoll Road, Chestertown, NY 12817
                        112 Carriage Knoll Road https://selectsothebysrealty.com/land/glb/202427761/112-carriage-knoll-road-chestertown-ny-12817 https://cdn.datafloat.com/FOS_PUBLIC/MLSPhotos/GLBCMN/202427761_1.jpg
                        76900 USD
                        Chestertown VT 12817
                        43.6669 -73.79353
                          • Open House
                          • Price Reduced $18,900
                          • New Listing
                          • Pending
                          • Coming Soon
                          • virtual Tour
                          • Sold
                          • Leased
                          102 Carriage Knoll Road, Chestertown, NY
                          $74,900
                          $74,900
                          MLS# 202427758Land
                          Sq. Ft.
                           
                          0 BEDS BATH BATHS
                          Request Info
                          Details
                          View Photos of 102 Carriage Knoll Road, Chestertown, NY 12817
                          102 Carriage Knoll Road https://selectsothebysrealty.com/land/glb/202427758/102-carriage-knoll-road-chestertown-ny-12817 https://cdn.datafloat.com/FOS_PUBLIC/MLSPhotos/GLBCMN/202427758_1.jpg
                          74900 USD
                          Chestertown VT 12817
                          43.66599 -73.79497
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