View 111 Barrington Lane Winchester, VA MLS# VAFV2043864
    Save 111 Barrington Lane Winchester, VA MLS# VAFV2043864
    1 of 19
    $1,800
    2

    Beds

    1.1

    Baths

    1,134

    Sq.Ft.

    111 Barrington Lane

    Winchester, VA

    Bright
    Courtesy of EXP REALTY, LLC
    View 3044 N Frederick Pike Winchester, VA MLS# VAFV2044204
      Save 3044 N Frederick Pike Winchester, VA MLS# VAFV2044204
      1 of 42
      $1,800
      3

      Beds

      1.1

      Baths

      1,326

      Sq.Ft.

      3044 N Frederick Pike

      Winchester, VA

      Bright
      Courtesy of COLONY REALTY
      View 128 Parkside Drive Winchester, VA MLS# VAFV2043756
        Save 128 Parkside Drive Winchester, VA MLS# VAFV2043756
        1 of 17
        $1,800
        3

        Beds

        1.1

        Baths

        1,200

        Sq.Ft.

        128 Parkside Drive

        Winchester, VA

        Bright
        Courtesy of RE/MAX ROOTS
        The time to sell is now! THE TIME TO SELL IS NOW!
        View 122 N Loudoun Street # 204 Winchester, VA MLS# VAWI2011472
        • Recently Listed
        Save 122 N Loudoun Street # 204 Winchester, VA MLS# VAWI2011472
        $1,800
        1

        Beds

        1.0

        Baths

        826

        Sq.Ft.

        122 N Loudoun Street # 204

        Winchester, VA

        Bright
        Courtesy of RE/MAX ROOTS
        View 328 Tudor Drive Winchester, VA MLS# VAFV2042572
          Save 328 Tudor Drive Winchester, VA MLS# VAFV2042572
          1 of 17
          $1,850
          2

          Beds

          2.1

          Baths

          1,374

          Sq.Ft.

          328 Tudor Drive

          Winchester, VA

          Bright
          Courtesy of CAMBRIDGE PREMIER REALTY, LLC.
          View 21 S Stewart Street # 4 Winchester, VA MLS# VAWI2007836
            Save 21 S Stewart Street # 4 Winchester, VA MLS# VAWI2007836
            1 of 12
            $1,900
            2

            Beds

            2.0

            Baths

            1,600

            Sq.Ft.

            21 S Stewart Street # 4

            Winchester, VA

            Bright
            Courtesy of COLONY REALTY
            View 125 Longstreet Avenue Winchester, VA MLS# VAFV2038398
              Save 125 Longstreet Avenue Winchester, VA MLS# VAFV2038398
              1 of 16
              $1,900
              3

              Beds

              1.1

              Baths

              1,004

              Sq.Ft.

              125 Longstreet Avenue

              Winchester, VA

              Bright
              Courtesy of CRUM REALTY, INC.
              View 105 Fay Street Winchester, VA MLS# VAFV2041472
                Save 105 Fay Street Winchester, VA MLS# VAFV2041472
                1 of 18
                $1,900
                3

                Beds

                1.1

                Baths

                1,636

                Sq.Ft.

                105 Fay Street

                Winchester, VA

                Bright
                Courtesy of ERA OAKCREST REALTY, INC.
                View 2325 Wilson Boulevard Winchester, VA MLS# VAWI2011364
                • Recently Listed
                Save 2325 Wilson Boulevard Winchester, VA MLS# VAWI2011364
                1 of 26
                $1,900
                3

                Beds

                1.0

                Baths

                1,073

                Sq.Ft.

                2325 Wilson Boulevard

                Winchester, VA

                Bright
                Courtesy of TETRA CORPORATION
                View 19 E Gerrard Street Winchester, VA MLS# VAWI2009514
                  Save 19 E Gerrard Street Winchester, VA MLS# VAWI2009514
                  1 of 6
                  $1,906

                  19 E Gerrard Street

                  Winchester, VA

                  Bright
                  Courtesy of VIRGINIA PROPERTY GROUP, INC.
                  View 321 N Kent Street Winchester, VA MLS# VAWI2010558
                    Save 321 N Kent Street Winchester, VA MLS# VAWI2010558
                    1 of 22
                    $1,950
                    3

                    Beds

                    1.1

                    Baths

                    1,280

                    Sq.Ft.

                    321 N Kent Street

                    Winchester, VA

                    Bright
                    Courtesy of MARKETPLACE REALTY
                    View 553 Highland Avenue Winchester, VA MLS# VAWI2011226
                      Save 553 Highland Avenue Winchester, VA MLS# VAWI2011226
                      1 of 20
                      $1,950
                      3

                      Beds

                      2.0

                      Baths

                      1,362

                      Sq.Ft.

                      553 Highland Avenue

                      Winchester, VA

                      Bright
                      Courtesy of SAMSON PROPERTIES
                      View 107-A Morgan Street Winchester, VA MLS# VAWI2011322
                      • Recently Listed
                      Save 107-A Morgan Street Winchester, VA MLS# VAWI2011322
                      1 of 12
                      $1,950
                      3

                      Beds

                      1.0

                      Baths

                      1,537

                      Sq.Ft.

                      107-A Morgan Street

                      Winchester, VA

                      Bright
                      Courtesy of SAMSON PROPERTIES
                      View 420 Royal Street Winchester, VA MLS# VAWI2011436
                      • Recently Listed
                      Save 420 Royal Street Winchester, VA MLS# VAWI2011436
                      1 of 7
                      $1,950
                      3

                      Beds

                      1.0

                      Baths

                      858

                      Sq.Ft.

                      420 Royal Street

                      Winchester, VA

                      Bright
                      Courtesy of VAZE REALTY
                      View 209 Boscawen Street E Winchester, VA MLS# VAWI2011272
                        Save 209 Boscawen Street E Winchester, VA MLS# VAWI2011272
                        1 of 9
                        $1,995

                        209 Boscawen Street E

                        Winchester, VA

                        Bright
                        Courtesy of COLDWELL BANKER PREMIER
                        View 2971 Valley Avenue Winchester, VA MLS# VAWI2010118
                          Save 2971 Valley Avenue Winchester, VA MLS# VAWI2010118
                          1 of 13
                          $2,000
                          Studio

                          Beds

                          0.0

                          Baths

                          800

                          Sq.Ft.

                          2971 Valley Avenue

                          Winchester, VA

                          Bright
                          Courtesy of LINK REALTY SERVICES LLC
                          View 2141 Valley Avenue Winchester, VA MLS# VAWI2011182
                            Save 2141 Valley Avenue Winchester, VA MLS# VAWI2011182
                            1 of 26
                            $2,000
                            3

                            Beds

                            2.0

                            Baths

                            1,725

                            Sq.Ft.

                            2141 Valley Avenue

                            Winchester, VA

                            Bright
                            Courtesy of RE/MAX ROOTS
                            View 112 Chatham Square Winchester, VA MLS# VAFV2044296
                            • Recently Listed
                            Save 112 Chatham Square Winchester, VA MLS# VAFV2044296
                            1 of 26
                            $2,000
                            4

                            Beds

                            2.1

                            Baths

                            1,754

                            Sq.Ft.

                            112 Chatham Square

                            Winchester, VA

                            Bright
                            Courtesy of KELLER WILLIAMS REALTY
                            View 122 Morningside Drive Winchester, VA MLS# VAWI2010590
                            • Virtual Tour
                            Save 122 Morningside Drive Winchester, VA MLS# VAWI2010590
                            1 of 12
                            $2,095
                            3

                            Beds

                            1.0

                            Baths

                            1,248

                            Sq.Ft.

                            122 Morningside Drive

                            Winchester, VA

                            Bright
                            Courtesy of COLDWELL BANKER PREMIER
                            View 108 Monticello Square Winchester, VA MLS# VAFV2043082
                              Save 108 Monticello Square Winchester, VA MLS# VAFV2043082
                              1 of 18
                              $2,095
                              3

                              Beds

                              2.2

                              Baths

                              1,740

                              Sq.Ft.

                              108 Monticello Square

                              Winchester, VA

                              Bright
                              Courtesy of VIRGINIA PROPERTY GROUP, INC.

                              About Winchester

                              Listings in Winchester, VA

                              645

                              Estimated median home price

                              $435,000
                              Winchester VA Homes for Sale & Properties

                              Weichert Realtors is one of the nation's leading providers of Winchester, Virginia real estate for sale and home ownership services. Contact Weichert today to buy or sell real estate in Winchester, VA.

                              Homes for Sale by Price in Winchester, VA

                              PriceCount
                              $0 - 100K44
                              $100K - 200K30
                              $200K - 300K57
                              $300K - 400K159
                              $400K - 500K94
                              $500K - 600K67
                              $600K - 700K59
                              $700K - 800K33
                              $800K - 900K19
                              $900K - 1M19
                              $1M - Max64

                              Homes for Sale by Type in Winchester, VA

                              Property TypeCount
                              Single Family371
                              Townhouse74
                              Condo26
                              Commercial51
                              Rental147
                              Lots and Land115
                              Condo/Town/CoOp0
                              CoOp0
                              Multi Family6
                              Mobile Home0
                              Farms2

                              (Data as of 8/25/2026)

                              Browse Neighborhoods

                              Find Properties in Winchester, VA

                              Winchester, VA Information

                              Find Properties by Zip

                              Information deemed reliable but not guaranteed.

                              Information Deemed Reliable But Not Guaranteed. The data relating to real estate for sale on this website appears in part through the BrightMLS Broker ReciprocitySM program, a voluntary cooperative exchange of property listing data between licensed real estate brokerage firms in which Weichert, Realtors® participates, and is provided by BrightMLS through a licensing agreement.

                              Real estate listings held by brokerage firms other than Weichert, Realtors® are marked with the Broker Reciprocity icon (a little black house) and detailed information about each listing includes the name of the listing broker.

                              The information provided by this website is for the personal, non-commercial use of consumers and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing.

                              Some properties which appear for sale on this website may no longer be available because they are under contract, have sold or are no longer being offered for sale.

                              © 2026 BrightMLS. All Rights Reserved.