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Homes for Sale In Winchester

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Viewing 1-12 of 391 listings
  • 1
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    • Open House
    • Price Reduced
    • New Listing
    • Virtual Tour
    • Active
    1657 Boswell Rd, Winchester, TN, 37398
    $3,800,000
    MLS# 2746411Single Family
    6 Beds8 Baths
    8,002 Sq. Ft.
    Courtesy of: Parks Compass
    Request Info Similar Properties
    Details
    1657 Boswell Rd https://choosecapstone.com/single-family/rlt/2746411/1657-boswell-rd-winchester-tn-37398 https://cdn.datafloat.com/ARC_PUBLIC/MLSPhotos/RLTCMN/2746411_1.jpg
    3800000 USD
    Winchester CA 37398
    35.23682 -86.24059
    982692
    5 1
    1657 Boswell Rd https://cdn.datafloat.com/ARC_PUBLIC/MLSPhotos/RLTCMN/2746411_1.jpg No data available
    3800000 USD http://schema.org/InStock 08/28/2024
    1657 Boswell Rd, Winchester, TN, 37398 Winchester TN 37398
    35.23682 -86.24059
    https://choosecapstone.com/single-family/rlt/2746411/1657-boswell-rd-winchester-tn-37398
    No Name Nil Nil Nil
    5 0 0
    Parks Compass Davey Hackett
      • Open House
      • Price Reduced
      • New Listing
      • Virtual Tour
      • Pending
      374 Ridgefield Cir, Winchester, TN, 37398
      $2,199,999
      MLS# 3186471Single Family
      4 Beds4 Baths
      3,684 Sq. Ft.
      Courtesy of: Keller Williams Realty Nashville/Franklin
      Request Info Similar Properties
      Details
      374 Ridgefield Cir https://choosecapstone.com/single-family/rlt/3186471/374-ridgefield-cir-winchester-tn-37398 https://cdn.datafloat.com/ARC_PUBLIC/MLSPhotos/RLTCMN/3186471_1.jpg
      2199999 USD
      Winchester CA 37398
      35.21512 -86.18156
      1083801
      5 1
      374 Ridgefield Cir https://cdn.datafloat.com/ARC_PUBLIC/MLSPhotos/RLTCMN/3186471_1.jpg No data available
      2199999 USD http://schema.org/InStock 04/28/2026
      374 Ridgefield Cir, Winchester, TN, 37398 Winchester TN 37398
      35.21512 -86.18156
      https://choosecapstone.com/single-family/rlt/3186471/374-ridgefield-cir-winchester-tn-37398
      No Name Nil Nil Nil
      5 0 0
      Keller Williams Realty Nashville/Franklin Derrick Foster
        • Open House
        • Price Reduced
        • New Listing
        • Virtual Tour
        • Active
        1376 Old Mansford Rd, Winchester, TN, 37398
        $2,095,000
        MLS# 3169953Single Family
        3 Beds5 Baths
        5,404 Sq. Ft.
        Courtesy of: Sam Hatfield Realty, Inc.
        Request Info Similar Properties
        Details
        1376 Old Mansford Rd https://choosecapstone.com/single-family/rlt/3169953/1376-old-mansford-rd-winchester-tn-37398 https://cdn.datafloat.com/ARC_PUBLIC/MLSPhotos/RLTCMN/3169953_1.jpg
        2095000 USD
        Winchester CA 37398
        35.20231 -86.23767
        1064261
        5 1
        1376 Old Mansford Rd https://cdn.datafloat.com/ARC_PUBLIC/MLSPhotos/RLTCMN/3169953_1.jpg No data available
        2095000 USD http://schema.org/InStock 03/31/2026
        1376 Old Mansford Rd, Winchester, TN, 37398 Winchester TN 37398
        35.20231 -86.23767
        https://choosecapstone.com/single-family/rlt/3169953/1376-old-mansford-rd-winchester-tn-37398
        No Name Nil Nil Nil
        5 0 0
        Sam Hatfield Realty, Inc. Sam Hatfield
          • Open House
          • Price Reduced
          • New Listing
          • Virtual Tour
          • Active
          7542 Chestnut Ridge Rd, Winchester, TN, 37398
          $2,000,000
          MLS# 3058553Lots/Land
          0 Beds0 Baths
          Sq. Ft.
          Courtesy of: SimpliHOM
          Request Info Similar Properties
          Details
          7542 Chestnut Ridge Rd https://choosecapstone.com/lots-land/rlt/3058553/7542-chestnut-ridge-rd-winchester-tn-37398 https://cdn.datafloat.com/ARC_PUBLIC/MLSPhotos/RLTCMN/3058553_1.jpg
          2000000 USD
          Winchester CA 37398
          35.26094 -86.27601
          981912
          5 1
          7542 Chestnut Ridge Rd https://cdn.datafloat.com/ARC_PUBLIC/MLSPhotos/RLTCMN/3058553_1.jpg No data available
          2000000 USD http://schema.org/InStock 11/14/2025
          7542 Chestnut Ridge Rd, Winchester, TN, 37398 Winchester TN 37398
          35.26094 -86.27601
          https://choosecapstone.com/lots-land/rlt/3058553/7542-chestnut-ridge-rd-winchester-tn-37398
          No Name Nil Nil Nil
          5 0 0
          SimpliHOM Dena Abbott
            • Open House
            • Price Reduced
            • New Listing
            • Virtual Tour
            • Active
            912 Dinah Shore Blvd, Winchester, TN, 37398
            $1,900,000
            MLS# 3179543Commercial
            0 Beds0 Baths
            Sq. Ft.
            Courtesy of: PCG Commercial, Inc
            Request Info Similar Properties
            Details
            912 Dinah Shore Blvd https://choosecapstone.com/commercial/rlt/3179543/912-dinah-shore-blvd-winchester-tn-37398 https://cdn.datafloat.com/ARC_PUBLIC/MLSPhotos/RLTCMN/3179543_1.jpg
            1900000 USD
            Winchester CA 37398
            35.19196 -86.10173
            1074154
            5 1
            912 Dinah Shore Blvd https://cdn.datafloat.com/ARC_PUBLIC/MLSPhotos/RLTCMN/3179543_1.jpg No data available
            1900000 USD http://schema.org/InStock 04/17/2026
            912 Dinah Shore Blvd, Winchester, TN, 37398 Winchester TN 37398
            35.19196 -86.10173
            https://choosecapstone.com/commercial/rlt/3179543/912-dinah-shore-blvd-winchester-tn-37398
            No Name Nil Nil Nil
            5 0 0
            PCG Commercial, Inc Adrian Del Rio
              • Open House
              • Price Reduced
              • New Listing
              • Virtual Tour
              • Pending
              55 Narrows Cir, Winchester, TN, 37398
              $1,900,000
              MLS# 3183656Single Family
              2 Beds3 Baths
              3,156 Sq. Ft.
              Courtesy of: Sam Hatfield Realty, Inc.
              Request Info Similar Properties
              Details
              55 Narrows Cir https://choosecapstone.com/single-family/rlt/3183656/55-narrows-cir-winchester-tn-37398 https://cdn.datafloat.com/ARC_PUBLIC/MLSPhotos/RLTCMN/3183656_1.jpg
              1900000 USD
              Winchester CA 37398
              35.19942 -86.26881
              1080144
              5 1
              55 Narrows Cir https://cdn.datafloat.com/ARC_PUBLIC/MLSPhotos/RLTCMN/3183656_1.jpg No data available
              1900000 USD http://schema.org/InStock 04/23/2026
              55 Narrows Cir, Winchester, TN, 37398 Winchester TN 37398
              35.19942 -86.26881
              https://choosecapstone.com/single-family/rlt/3183656/55-narrows-cir-winchester-tn-37398
              No Name Nil Nil Nil
              5 0 0
              Sam Hatfield Realty, Inc. Sam Hatfield
                • Open House
                • Price Reduced
                • New Listing
                • Virtual Tour
                • Active
                3819 Tullahoma Hwy, Winchester, TN, 37398
                $1,800,000
                MLS# 3000595Lots/Land
                0 Beds0 Baths
                Sq. Ft.
                Courtesy of: Horizon Realty Group dba Keller Williams Horizon
                Request Info Similar Properties
                Details
                3819 Tullahoma Hwy https://choosecapstone.com/lots-land/rlt/3000595/3819-tullahoma-hwy-winchester-tn-37398 https://cdn.datafloat.com/ARC_PUBLIC/MLSPhotos/RLTCMN/3000595_1.jpg
                1800000 USD
                Winchester CA 37398
                35.23191 -86.11124
                1082752
                5 1
                3819 Tullahoma Hwy https://cdn.datafloat.com/ARC_PUBLIC/MLSPhotos/RLTCMN/3000595_1.jpg No data available
                1800000 USD http://schema.org/InStock 09/22/2025
                3819 Tullahoma Hwy, Winchester, TN, 37398 Winchester TN 37398
                35.23191 -86.11124
                https://choosecapstone.com/lots-land/rlt/3000595/3819-tullahoma-hwy-winchester-tn-37398
                No Name Nil Nil Nil
                5 0 0
                Horizon Realty Group dba Keller Williams Horizon Jennifer W. Murdock
                  • Open House
                  • Price Reduced
                  • New Listing
                  • Virtual Tour
                  • Active
                  959 Fanning Bend Dr, Winchester, TN, 37398
                  $1,699,000
                  MLS# 3183045Single Family
                  6 Beds8 Baths
                  4,678 Sq. Ft.
                  Courtesy of: Legacy South Brokerage
                  Request Info Similar Properties
                  Details
                  959 Fanning Bend Dr https://choosecapstone.com/single-family/rlt/3183045/959-fanning-bend-dr-winchester-tn-37398 https://cdn.datafloat.com/ARC_PUBLIC/MLSPhotos/RLTCMN/3183045_1.jpg
                  1699000 USD
                  Winchester CA 37398
                  35.22283 -86.20969
                  1079336
                  5 1
                  959 Fanning Bend Dr https://cdn.datafloat.com/ARC_PUBLIC/MLSPhotos/RLTCMN/3183045_1.jpg No data available
                  1699000 USD http://schema.org/InStock 04/27/2026
                  959 Fanning Bend Dr, Winchester, TN, 37398 Winchester TN 37398
                  35.22283 -86.20969
                  https://choosecapstone.com/single-family/rlt/3183045/959-fanning-bend-dr-winchester-tn-37398
                  No Name Nil Nil Nil
                  5 0 0
                  Legacy South Brokerage Brandon Bubis
                    • Open House
                    • Price Reduced
                    • New Listing
                    • Virtual Tour
                    • Active
                    1485 Water Tank Rd, Winchester, TN, 37398
                    $1,575,000
                    MLS# 3183871Single Family
                    3 Beds5 Baths
                    6,300 Sq. Ft.
                    Courtesy of: Swaffords Property Shop
                    Request Info Similar Properties
                    Details
                    1485 Water Tank Rd https://choosecapstone.com/single-family/rlt/3183871/1485-water-tank-rd-winchester-tn-37398 https://cdn.datafloat.com/ARC_PUBLIC/MLSPhotos/RLTCMN/3183871_1.jpg
                    1575000 USD
                    Winchester CA 37398
                    35.14519 -86.03472
                    1080441
                    5 1
                    1485 Water Tank Rd https://cdn.datafloat.com/ARC_PUBLIC/MLSPhotos/RLTCMN/3183871_1.jpg No data available
                    1575000 USD http://schema.org/InStock 04/17/2026
                    1485 Water Tank Rd, Winchester, TN, 37398 Winchester TN 37398
                    35.14519 -86.03472
                    https://choosecapstone.com/single-family/rlt/3183871/1485-water-tank-rd-winchester-tn-37398
                    No Name Nil Nil Nil
                    5 0 0
                    Swaffords Property Shop Sharon Swafford
                      • Open House
                      • Price Reduced
                      • New Listing
                      • Virtual Tour
                      • Active
                      405 Sharp Springs Rd, Winchester, TN, 37398
                      $1,500,000
                      MLS# 3056561Lots/Land
                      0 Beds0 Baths
                      Sq. Ft.
                      Courtesy of: Winton Auction & Realty Co.
                      Request Info Similar Properties
                      Details
                      405 Sharp Springs Rd https://choosecapstone.com/lots-land/rlt/3056561/405-sharp-springs-rd-winchester-tn-37398 https://cdn.datafloat.com/ARC_PUBLIC/MLSPhotos/RLTCMN/3056561_1.jpg
                      1500000 USD
                      Winchester CA 37398
                      35.19511 -86.10963
                      979683
                      5 1
                      405 Sharp Springs Rd https://cdn.datafloat.com/ARC_PUBLIC/MLSPhotos/RLTCMN/3056561_1.jpg No data available
                      1500000 USD http://schema.org/InStock 12/02/2025
                      405 Sharp Springs Rd, Winchester, TN, 37398 Winchester TN 37398
                      35.19511 -86.10963
                      https://choosecapstone.com/lots-land/rlt/3056561/405-sharp-springs-rd-winchester-tn-37398
                      No Name Nil Nil Nil
                      5 0 0
                      Winton Auction & Realty Co. Thomas Ore
                        • Open House
                        • Price Reduced$30,000
                        • New Listing
                        • Virtual Tour
                        • Active
                        71 Slalom Cir, Winchester, TN, 37398
                        $1,495,000
                        MLS# 3112698Single Family
                        4 Beds4 Baths
                        4,500 Sq. Ft.
                        Courtesy of: Swaffords Property Shop
                        Request Info Similar Properties
                        Details
                        71 Slalom Cir https://choosecapstone.com/single-family/rlt/3112698/71-slalom-cir-winchester-tn-37398 https://cdn.datafloat.com/ARC_PUBLIC/MLSPhotos/RLTCMN/3112698_1.jpg
                        1495000 USD
                        Winchester CA 37398
                        35.19212 -86.13396
                        1010635
                        5 1
                        71 Slalom Cir https://cdn.datafloat.com/ARC_PUBLIC/MLSPhotos/RLTCMN/3112698_1.jpg No data available
                        1495000 USD http://schema.org/InStock 01/15/2026
                        71 Slalom Cir, Winchester, TN, 37398 Winchester TN 37398
                        35.19212 -86.13396
                        https://choosecapstone.com/single-family/rlt/3112698/71-slalom-cir-winchester-tn-37398
                        No Name Nil Nil Nil
                        5 0 0
                        Swaffords Property Shop Kay Caldwell
                          • Open House
                          • Price Reduced$40,000
                          • New Listing
                          • Virtual Tour
                          • Active
                          644 Fanning Bend Dr, Winchester, TN, 37398
                          $1,485,000
                          MLS# 3156440Single Family
                          4 Beds4 Baths
                          3,922 Sq. Ft.
                          Courtesy of: eXp Realty
                          Request Info Similar Properties
                          Details
                          644 Fanning Bend Dr https://choosecapstone.com/single-family/rlt/3156440/644-fanning-bend-dr-winchester-tn-37398 https://cdn.datafloat.com/ARC_PUBLIC/MLSPhotos/RLTCMN/3156440_1.jpg
                          1485000 USD
                          Winchester CA 37398
                          35.21859 -86.20787
                          1053619
                          5 1
                          644 Fanning Bend Dr https://cdn.datafloat.com/ARC_PUBLIC/MLSPhotos/RLTCMN/3156440_1.jpg No data available
                          1485000 USD http://schema.org/InStock 03/20/2026
                          644 Fanning Bend Dr, Winchester, TN, 37398 Winchester TN 37398
                          35.21859 -86.20787
                          https://choosecapstone.com/single-family/rlt/3156440/644-fanning-bend-dr-winchester-tn-37398
                          No Name Nil Nil Nil
                          5 0 0
                          eXp Realty Clay Kelton | Kelton Group
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