37,023

Winchester, VA Homes

Section Image Section Image
  • /23

    $127,750

    • Land
    • 8.11 Acres
    • $15,752 per Acre

    0 Wolf Spring Trail Unit LotWP001, Winchester, VA 22602

    Rare opportunity to own three adjoining fully wooded parcels in the quiet and peaceful Shawneeland community. Numerous residential and recreational possibilities exist with ownership of these tracts. Located just a few miles west of Winchester in the Rosenberger area of the county. Access is secured via extensive road frontage on paved Wolf Spring Trail. Utilities are close by, making for easy

    Chad Pangle Whitetail Properties Real Estate

    0 Wolf Spring Trail Unit LotWP001, Winchester, VA 22602
  • /29

    $2,650 Per Month

    • 4 Beds
    • 2.5 Baths
    • 1,303 Sq Ft
    • House for Rent

    1517 Caroline St, Winchester, VA 22601

    Welcome to this charming split foyer home in Winchester, VA!The upper level offers a generous sized living room/dining room combo, and eat-in kitchen with stainless steel appliances. Completing this level is a primary suite with full bath, two additional bedrooms, and additional full bath.Additional living space in the lower level includes a rec room, additional bedroom, half bath

    Patrick Blood Blackwell Property Mangement, LLC

    1517 Caroline St, Winchester, VA 22601
  • /38

    $489,000

    Sold Feb 12, 2026

    107 Tucks Cir, Winchester, VA 22602

    • 4 Beds
    • 2 Baths
    • 2,401 Sq Ft
    • Built 1992

    Last Sold Summary

    • $204/SF
    • 10 Days On Market

    Current Estimated Value $494,101

    Last Listing Agent Katy Donovan Keller Williams Realty

    107 Tucks Cir, Winchester, VA 22602
    • /7

      Est $193,101

      Not Listed For Sale

      130 Lilac Ln, Winchester, VA 22602

      130 Lilac Ln, Winchester, VA 22602

      Last Sold Summary

      • 504 Days On Market

      Last Listing Agent Gillian Greenfield Coldwell Banker Premier

  • /19

    $131,500

    $10K PRICE DROP
    • Land
    • 11.1 Acres
    • $11,847 per Acre

    0 Hodges Ln Unit LotWP014, Winchester, VA 22603

    Own a piece of the beautiful Back Creek Heights community in Cross Junction. Located just minutes north of Winchester in the Dehaven part of the county. Access is secured via road frontage on Hodges Lane. Experience exciting hunting as many types of wildlife call this property home, including deer, turkey, and many small game species. This tract is currently being used for recreation and hunting.

    Chad Pangle Whitetail Properties Real Estate

    0 Hodges Ln Unit LotWP014, Winchester, VA 22603
  • /15

    $1,495

    Total Monthly Price

    • 2 Beds
    • 1 Bath
    • 880 Sq Ft
    • Townhouse for Rent

    502 N Loudoun St, Winchester, VA 22601

    2 Bedroom 1 Bath Great downtown location! Close enough to indulge in all they hustle and bustle Downtown Winchester is loved for but tucked away on a quiet street so you can just sit and relax on the porch or enjoy the spacious back yard. Gas hot water heater and furnace- water/sewer split and cats welcome with approval and additional fees. 2 Bedroom 1 Bath

    502 N Loudoun St, Winchester, VA 22601
  • /47

    $512,000

    Sold Feb 27, 2026

    216 Fairmont Ave, Winchester, VA 22601

    • 3 Beds
    • 1.5 Baths
    • 2,177 Sq Ft
    • Built 1911

    Last Sold Summary

    • $235/SF
    • 81 Days On Market

    Current Estimated Value $545,213

    Last Listing Agent Dave Spence RE/MAX Roots

    216 Fairmont Ave, Winchester, VA 22601
    • /14

      Not Listed For Sale

      611 Laurelwood Cir, Winchester, VA 22601

      • 3 Beds
      • 2.5 Baths
      • 1,442 Sq Ft
      611 Laurelwood Cir, Winchester, VA 22601

      Last Sold Summary

      • 28 Days On Market

  • /32

    $299,900

    Under Contract
    • 3 Beds
    • 2 Baths
    • 1,290 Sq Ft

    352 Woodchuck Ln, Winchester, VA 22602

    Welcome to 352 Woodchuck Lane in Winchester, VA! This charming 3-bedroom, 2-bath home sits on .92 flat acres, offering plenty of room to create the small homestead you’ve been dreaming of. The level lot provides an ideal setting for gardens, outdoor entertaining, pets, chickens, or simply enjoying the peace and privacy of your own land.Inside, you’ll find a comfortable and flowing layout with

    Emiley Boggs Samson Properties

    352 Woodchuck Ln, Winchester, VA 22602
  • /18

    $1,425 Per Month

    • 2 Beds
    • 1 Bath
    • 1,022 Sq Ft
    • Townhouse for Rent

    219 Baker St, Winchester, VA 22601

    Welcome to this charming twin home conveniently located in the heart of the City of Winchester. Offering approximately 1,022 square feet of comfortable living space, this well-maintained residence features 2 spacious bedrooms and 1 full bathroom, making it an inviting home for those seeking comfort, convenience, and a great location.Just approximately one minute from downtown Winchester,

    Elna Brown Pearson Smith Realty, LLC

    219 Baker St, Winchester, VA 22601
  • /70

    $375,000

    Sold Feb 23, 2026

    313 Beaver Trail, Winchester, VA 22602

    • 3 Beds
    • 2.5 Baths
    • 1,631 Sq Ft
    • Built 2018

    Last Sold Summary

    • 1% Below List Price
    • $230/SF
    • 39 Days On Market

    Current Estimated Value $384,795

    Last Listing Agent Dana Durr CENTURY 21 New Millennium

    313 Beaver Trail, Winchester, VA 22602
    • /28

      Not Listed For Sale

      201 Winchester Dr, Winchester, VA 22602

      • 3 Beds
      • 2 Baths
      • 2,075 Sq Ft
      • Built 2025
      201 Winchester Dr, Winchester, VA 22602

      Last Sold Summary

      • 4 Days On Market

      Last Listing Agent Sheila Pack RE/MAX Roots

  • /42

    $289,900

    Under Contract
    • 3 Beds
    • 3.5 Baths
    • 1,906 Sq Ft

    114 Tudor Dr, Winchester, VA 22603

    Spacious three-level townhome in a desirable Winchester community, conveniently located near Sunnyside and Old Town Winchester! Offering generously sized bedrooms, three and a half baths, and flexible living space across three levels, this home has room for everyone.The main level features a comfortable family room, dining area, kitchen, and convenient powder room, with access to the

    Bradley Comstock ERA Oakcrest Realty, Inc.

    114 Tudor Dr, Winchester, VA 22603
  • /28

    $4,500

    Total Monthly Price

    • 5 Beds
    • 4 Baths
    • 4,231 Sq Ft
    • Condo for Rent

    181 Williamson Rd, Winchester, VA 22602

    Available November 1, 2026! Welcome to 181 Williamson Road, an exceptional five-bedroom, four-bath custom home for rent in Winchester, Virginia. Built in 2023, this impressive property offers 4,231 square feet of modern living space, energy-efficient upgrades, and premium indoor and outdoor amenities.The open-concept main level features hard-surface flooring, an expansive living room,

    181 Williamson Rd, Winchester, VA 22602
  • /53

    $750,000

    Sold Sep 22, 2025

    977 W Parkins Mill Rd, Winchester, VA 22602

    • 5 Beds
    • 3.5 Baths
    • 3,928 Sq Ft
    • Built 1975

    Last Sold Summary

    • $191/SF
    • 68 Days On Market

    Current Estimated Value $720,713

    Last Listing Agent Nicole Renzetti EXP Realty, LLC

    977 W Parkins Mill Rd, Winchester, VA 22602
    • /14

      Not Listed For Sale

      629 Laurelwood Cir, Winchester, VA 22601

      • 3 Beds
      • 2.5 Baths
      • 1,442 Sq Ft
      629 Laurelwood Cir, Winchester, VA 22601

      Last Sold Summary

      • 8 Days On Market

  • /2

    $383,000

    Coming Soon Sep 24
    • 3 Beds
    • 2 Baths
    • 1,486 Sq Ft

    208 Lauck Dr, Winchester, VA 22603

    COMING SOON – 208 Lauck Drive, Winchester, VA! This is one you won’t want to miss. This inviting 3-bedroom, 2-bath ranch offers comfortable one-level living, a large, beautifully landscaped yard, and several important updates, including a new roof, newer HVAC system, and newer water heater. Priced to sell and full of potential, this home is expected to attract plenty of attention. Property will

    Rick Guthrie Keller Williams Realty

    208 Lauck Dr, Winchester, VA 22603
  • /8

    $1,800 Per Month

    • 3 Beds
    • 1 Bath
    • 1,480 Sq Ft
    • House for Rent

    120 W Whitlock Ave, Winchester, VA 22601

    Home is clean and in excellent condition., Walking distance to downtown and Handley High School. Hardwood floors throughout. Fenced in yard and off street parking. Washer and dryer included. This is a pet free and smoke free home.

    Meridee Powars Link Realty Services LLC

    120 W Whitlock Ave, Winchester, VA 22601
  • /25

    $575,990

    Sold Jul 07, 2026

    131 Wappinger Terrace, Winchester, VA 22602

    • 5 Beds
    • 4 Baths
    • 2,511 Sq Ft
    • Built 2026

    Move in Ready Sold Summary

    • $229/SF
    • 17 Days On Market

    D.R. Horton Retreat at Winding Creek - Single Family

    131 Wappinger Terrace, Winchester, VA 22602
    • /68

      Est $457,849

      Not Listed For Sale

      103 Woodbury Ct, Winchester, VA 22602

      • 3 Beds
      • 2.5 Baths
      • 2,268 Sq Ft
      • Built 1998
      103 Woodbury Ct, Winchester, VA 22602

      Last Sold Summary

      • 0 Days On Market

      Last Listing Agent Lane McIntosh Mclntosh Realty Group

  • /54

    $459,900

    • 3 Beds
    • 2 Baths
    • 1,834 Sq Ft

    991 Front Royal Pike, Winchester, VA 22602

    Enjoy easy one-level living in this well-maintained ranch home conveniently located in Winchester, close to commuter routes, shopping, restaurants, and everyday amenities. The inviting front porch is the perfect spot to relax and enjoy warm evenings. Inside, hardwood floors flow through the living room, kitchen, and dining area, while the bedrooms feature comfortable carpeting. A dedicated

    James King RE/MAX Roots

    991 Front Royal Pike, Winchester, VA 22602
  • /11

    $1,150

    Total Monthly Price

    • 2 Beds
    • 1 Bath
    • Condo for Rent

    22 Peyton St Unit 3, Winchester, VA 22601

    Spacious 2 bedroom 1 bath 2nd floor apartment ready for occupancy! No smoking no animals please. $50 application fee per person, NVAR or VAR rental application ok or can apply thru listers website. Water/sewer/trash included. Tenant pays electric. Max 3 person occupancy.

    22 Peyton St Unit 3, Winchester, VA 22601
  • /13

    $325,000

    Sold Aug 25, 2026

    632 Watson Ave, Winchester, VA 22601

    • 3 Beds
    • 2 Baths
    • 1,465 Sq Ft
    • Built 1940

    Last Sold Summary

    • $222/SF
    • 51 Days On Market

    Current Estimated Value $314,565

    Last Listing Agent Jennifer Sacco RE/MAX Roots

    632 Watson Ave, Winchester, VA 22601
    • /10

      Not Listed For Sale

      0 Oak Ridge Ln Unit VAFV2035504, Winchester, VA 22602

      0 Oak Ridge Ln Unit VAFV2035504, Winchester, VA 22602

      Last Sold Summary

      • 15 Days On Market

      Last Listing Agent Sarah Abderrazzaq Realty ONE Group Old Towne

  • /2

    $394,990

    New Construction
    • 3 Beds
    • 2.5 Baths
    • 1,893 Sq Ft

    404 Granite Ridge Dr, Winchester, VA 22603

    Main-level living at its best in Hiatt Pointe at Snowden Bridge—a gated 55+ active adult community.This low-maintenance villa features a primary bedroom and laundry on the entry level, a screened rear porch, and a one-car garage. Upstairs offers two spacious bedrooms with walk-in closets and a full bath, plus a finished storage area! Enjoy a stylish kitchen with quartz counters, stainless

    Brookfield Residential Builder
    404 Granite Ridge Dr, Winchester, VA 22603
  • /15

    $1,750 Per Month

    • 1 Bed
    • 1 Bath
    • 778 Sq Ft
    • Condo for Rent

    517 Amherst St, Winchester, VA 22601

    Brand-new apartments in the heart of Winchester City! Just a few steps from the lovely Museum of the Shenandoah Valley and Old Town Mall.There are six newly constructed apartments, all located on the second floor and accessible by stairs. The apartments are situated above Boxwell Pharmacy, The Adult Care Center, and Stix & Stones.This apartment features one bedroom and one full

    Cara Wilkins MarketPlace REALTY

    517 Amherst St, Winchester, VA 22601
  • /41

    $300,000

    Sold Dec 18, 2025

    2294 Front Royal Pike, Winchester, VA 22602

    • 3 Beds
    • 1 Bath
    • 1,974 Sq Ft
    • Built 1968

    Last Sold Summary

    • $152/SF
    • 29 Days On Market

    Current Estimated Value $341,479

    Last Listing Agent Sarah Hott Realty ONE Group Old Towne

    2294 Front Royal Pike, Winchester, VA 22602
    • /50

      Not Listed For Sale

      107 Lakota St, Winchester, VA 22602

      • 4 Beds
      • 3.5 Baths
      • 1,889 Sq Ft
      • Built 2024
      107 Lakota St, Winchester, VA 22602

      Last Sold Summary

      • 3 Days On Market

      Last Listing Agent Brooks Sears Pearson Smith Realty, LLC

  • /3

    $225,000

    • 3 Beds
    • 1 Bath
    • 1,008 Sq Ft

    310 Crest Cir, Winchester, VA 22602

    Charming rambler waiting for your personal touches. New roof installed 2026

    Jamie Weiss M.O. Wilson Properties

    310 Crest Cir, Winchester, VA 22602
  • /6

    $1,295

    Total Monthly Price

    • 1 Bed
    • 1 Bath
    • 600 Sq Ft
    • Townhouse for Rent

    714 S Cameron St, Winchester, VA 22601

    Great upper level apartment close to downtown Winchester. Just a short walk to Handley library, government offices, museums, the Old Town Walking Mall and all the charming shops, pubs and food. This apartment has spacious rooms, a full kitchen and bathroom, full hardwood floors throughout and a fresh coat of paint to brighten it up! Don't feel like taking a walk, just sit on your side porch while

    714 S Cameron St, Winchester, VA 22601
  • /36

    $335,000

    Sold Nov 21, 2025

    614 Remington Dr, Winchester, VA 22602

    • 3 Beds
    • 2 Baths
    • 1,232 Sq Ft
    • Built 2009

    Last Sold Summary

    • $272/SF
    • 26 Days On Market

    Current Estimated Value $337,075

    Last Listing Agent Michael Sprague Samson Properties

    614 Remington Dr, Winchester, VA 22602
    • /18

      Not Listed For Sale

      106 Manasquan Way, Winchester, VA 22602

      • 3 Beds
      • 2.5 Baths
      • 1,665 Sq Ft
      • Built 2025
      106 Manasquan Way, Winchester, VA 22602

      Last Sold Summary

      • 13 Days On Market

  • /76

    $989,000

    • 4 Beds
    • 3.5 Baths
    • 4,152 Sq Ft

    137 Old Forest Cir, Winchester, VA 22602

    Nestled in the highly sought-after Stonebrook neighborhood, this incredibly quiet wooded property offers the perfect blend of privacy and convenience. This 2.6 acre estate provides a peaceful country setting while remaining close to modern amenities.Step inside and discover a thoughtfully updated home featuring 4 bedrooms and 3.5 bathrooms. The inviting living spaces include a warm and

    Melissa Perozich Century 21 Redwood Realty

    137 Old Forest Cir, Winchester, VA 22602
  • /18

    $2,100 Per Month

    • 4 Beds
    • 1.5 Baths
    • 1,800 Sq Ft
    • House for Rent

    317 S Kent St, Winchester, VA 22601

    Charming 1931 brick home available for rent! This spacious home features 4 bedrooms, 1 full bath and 1 half bath, and the convenience of a main-level washer and dryer. Each bedroom includes ample closet space. Relax on the welcoming front porch or enjoy the fenced in backyard. The home is located right next to the Ruth Jackson Memorial Park and the Green Circle entrance is right across the

    Danielle Spriggs Samson Properties

    317 S Kent St, Winchester, VA 22601
  • /51

    $1,100,000

    Sold Apr 27, 2026

    270 Sotheby Ct, Winchester, VA 22602

    • 4 Beds
    • 3.5 Baths
    • 3,945 Sq Ft
    • Built 2006

    Last Sold Summary

    • $279/SF
    • 13 Days On Market

    Current Estimated Value $1,085,194

    Last Listing Agent Paul Gallagher Colony Realty

    270 Sotheby Ct, Winchester, VA 22602
    • /19

      Not Listed For Sale

      136 Magpie, Winchester, VA 22603

      • 4 Beds
      • 3 Baths
      • 3,518 Sq Ft
      • Built 2025
      136 Magpie, Winchester, VA 22603

      Last Sold Summary

      • 47 Days On Market

      Last Listing Agent Elizabeth Ellis Brookfield Mid-Atlantic Brokerage, LLC

  • /20

    $399,990

    New Construction $5K PRICE DROP
    • 3 Beds
    • 4 Baths
    • 1,905 Sq Ft

    134 Swansong Place, Winchester, VA 22603

    The three-level Skyline model masterfully combines a traditional exterior with a contemporary, open-concept floor plan. On the main level, you’ll find an expansive living room, bathed in natural light from numerous windows, flows effortlessly into the dining area and kitchen. The kitchen is designed with an L-shaped countertop and an island that borders the dining room. A cozy nook serves as a

    Brookfield Residential Builder
    134 Swansong Place, Winchester, VA 22603
  • /11

    $2,500

    Total Monthly Price

    • 2 Beds
    • 2 Baths
    • Condo for Rent

    137 S Loudoun St Unit 201, Winchester, VA 22601

    137 S Loudoun St Unit 201, Winchester, VA 22601
  • /145

    $1,500,000

    Sold Oct 28, 2025

    731 Apple Pie Ridge Rd, Winchester, VA 22603

    • 4 Beds
    • 3.5 Baths
    • 4,304 Sq Ft
    • Built 1790

    Last Sold Summary

    • $349/SF
    • 5 Days On Market

    Current Estimated Value $1,220,479

    Last Listing Agent Ann Smith Berkshire Hathaway HomeServices PenFed Realty

    731 Apple Pie Ridge Rd, Winchester, VA 22603
    • /40

      Not Listed For Sale

      623 Shawnee Trail, Winchester, VA 22602

      • 3 Beds
      • 2.5 Baths
      • 1,608 Sq Ft
      • Built 2025
      623 Shawnee Trail, Winchester, VA 22602

      Last Sold Summary

      • 0 Days On Market

      Last Listing Agent RoxAnn Grimes RE/MAX Roots

Showing Results 201 - 240, Page 6 of 18

How to Buy a Home How to Finance a Home How to Sell a Home