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

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    Courtesy of VIRGINIA PROPERTY GROUP, INC.
    View 178 Sioux Loop Winchester, VA MLS# VAFV2043044
      Save 178 Sioux Loop Winchester, VA MLS# VAFV2043044
      1 of 15
      $2,195
      4

      Beds

      3.1

      Baths

      1,889

      Sq.Ft.

      178 Sioux Loop

      Winchester, VA

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      Courtesy of PARTNERS REAL ESTATE
      View 544 Allston Circle Winchester, VA MLS# VAFV2043018
        Save 544 Allston Circle Winchester, VA MLS# VAFV2043018
        1 of 19
        $1,500
        2

        Beds

        1.1

        Baths

        1,106

        Sq.Ft.

        544 Allston Circle

        Winchester, VA

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        Courtesy of CRUM REALTY, INC.
        The time to sell is now! THE TIME TO SELL IS NOW!
        View 317 S Kent Street Winchester, VA MLS# VAWI2011060
          Save 317 S Kent Street Winchester, VA MLS# VAWI2011060
          1 of 18
          $2,100
          4

          Beds

          1.1

          Baths

          1,800

          Sq.Ft.

          317 S Kent Street

          Winchester, VA

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          Courtesy of SAMSON PROPERTIES
          View 128 Wappinger Terrace Winchester, VA MLS# VAFV2042982
          • New Construction
          Save 128 Wappinger Terrace Winchester, VA MLS# VAFV2042982
          1 of 12
          $2,700
          4

          Beds

          2.1

          Baths

          1,953

          Sq.Ft.

          128 Wappinger Terrace

          Winchester, VA

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          Courtesy of SAMSON PROPERTIES
          View 131 Frogale Court Winchester, VA MLS# VAFV2042848
            Save 131 Frogale Court Winchester, VA MLS# VAFV2042848
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            $36,167
            37,690

            Sq.Ft.

            131 Frogale Court

            Winchester, VA

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            Courtesy of KELLER WILLIAMS REALTY
            View Route 37 and Shady Elm Road Winchester, VA MLS# VAFV2038418
            • New Construction
            Save Route 37 and Shady Elm Road Winchester, VA MLS# VAFV2038418
            1 of 5
            $2,500
            48,000

            Sq.Ft.

            Route 37 and Shady Elm Road

            Winchester, VA

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            Courtesy of KELLER WILLIAMS REALTY
            View 117 Stribling Winchester, VA MLS# VAFV2042706
              Save 117 Stribling Winchester, VA MLS# VAFV2042706
              1 of 25
              $2,195
              3

              Beds

              2.1

              Baths

              2,420

              Sq.Ft.

              117 Stribling

              Winchester, VA

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              Courtesy of KELLER WILLIAMS REALTY
              View 621 Patterson Avenue Winchester, VA MLS# VAWI2010988
                Save 621 Patterson Avenue Winchester, VA MLS# VAWI2010988
                1 of 25
                $2,200
                3

                Beds

                2.1

                Baths

                2,053

                Sq.Ft.

                621 Patterson Avenue

                Winchester, VA

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                Courtesy of LONG & FOSTER REAL ESTATE, INC.
                View 350 Sage Circle Winchester, VA MLS# VAFV2042562
                  Save 350 Sage Circle Winchester, VA MLS# VAFV2042562
                  1 of 32
                  $2,345
                  3

                  Beds

                  2.1

                  Baths

                  1,800

                  Sq.Ft.

                  350 Sage Circle

                  Winchester, VA

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                  Courtesy of PEARSON SMITH REALTY, LLC
                  View 703 S Loudoun Street Winchester, VA MLS# VAWI2010928
                    Save 703 S Loudoun Street Winchester, VA MLS# VAWI2010928
                    1 of 32
                    $2,500
                    3

                    Beds

                    2.1

                    Baths

                    1,992

                    Sq.Ft.

                    703 S Loudoun Street

                    Winchester, VA

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                    Courtesy of SAMSON PROPERTIES
                    View 703 S Loudoun Street Winchester, VA MLS# VAWI2010924
                      Save 703 S Loudoun Street Winchester, VA MLS# VAWI2010924
                      1 of 41
                      $3,700
                      3

                      Beds

                      2.1

                      Baths

                      1,992

                      Sq.Ft.

                      703 S Loudoun Street

                      Winchester, VA

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                      View 308 Gainesboro Road Winchester, VA MLS# VAFV2042308
                        Save 308 Gainesboro Road Winchester, VA MLS# VAFV2042308
                        1 of 17
                        $1,500
                        3

                        Beds

                        1.0

                        Baths

                        1,460

                        Sq.Ft.

                        308 Gainesboro Road

                        Winchester, VA

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                        Courtesy of OLIVETREE PROPERTY GROUP
                        View 4 W Cork Street # 1 Winchester, VA MLS# VAWI2010870
                          Save 4 W Cork Street # 1 Winchester, VA MLS# VAWI2010870
                          1 of 6
                          $1,350
                          1

                          Beds

                          1.0

                          Baths

                          400

                          Sq.Ft.

                          4 W Cork Street # 1

                          Winchester, VA

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                          View 210 E Boscawen St # 200 Winchester, VA MLS# VAWI2010872
                            Save 210 E Boscawen St # 200 Winchester, VA MLS# VAWI2010872
                            1 of 23
                            $2,500
                            2

                            Beds

                            2.0

                            Baths

                            1,150

                            Sq.Ft.

                            210 E Boscawen St # 200

                            Winchester, VA

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                            View 203 E Whitlock Avenue Winchester, VA MLS# VAWI2010812
                              Save 203 E Whitlock Avenue Winchester, VA MLS# VAWI2010812
                              1 of 9
                              $1,495
                              3

                              Beds

                              1.0

                              Baths

                              6,578

                              Sq.Ft.

                              203 E Whitlock Avenue

                              Winchester, VA

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                              Courtesy of CAMBRIDGE PREMIER REALTY, LLC.
                              View 207 E Whitlock Avenue Winchester, VA MLS# VAWI2010830
                                Save 207 E Whitlock Avenue Winchester, VA MLS# VAWI2010830
                                1 of 10
                                $1,395
                                3

                                Beds

                                1.0

                                Baths

                                6,578

                                Sq.Ft.

                                207 E Whitlock Avenue

                                Winchester, VA

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                                View 2261 Valley Avenue Winchester, VA MLS# VAWI2010836
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                                  1 of 2
                                  $15

                                  2261 Valley Avenue

                                  Winchester, VA

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                                  Courtesy of RE/MAX ROOTS
                                  View 2271 Valley Avenue Winchester, VA MLS# VAWI2010838
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                                    $18

                                    2271 Valley Avenue

                                    Winchester, VA

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                                    View 2446 Valley Avenue Winchester, VA MLS# VAWI2010820
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                                      $15

                                      2446 Valley Avenue

                                      Winchester, VA

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                                      About Winchester

                                      Listings in Winchester, VA

                                      640

                                      Estimated median home price

                                      $439,000
                                      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 - 100K43
                                      $100K - 200K31
                                      $200K - 300K56
                                      $300K - 400K152
                                      $400K - 500K93
                                      $500K - 600K65
                                      $600K - 700K61
                                      $700K - 800K32
                                      $800K - 900K21
                                      $900K - 1M19
                                      $1M - Max67

                                      Homes for Sale by Type in Winchester, VA

                                      Property TypeCount
                                      Single Family366
                                      Townhouse75
                                      Condo23
                                      Commercial52
                                      Rental158
                                      Lots and Land116
                                      Condo/Town/CoOp0
                                      CoOp0
                                      Multi Family6
                                      Mobile Home0
                                      Farms2

                                      (Data as of 8/29/2026)

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                                      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.

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