Winchester County, VA Homes

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  $430,000

  • 4 Beds
  • 2 Baths
  • 2,100 Sq Ft

  17 E Leicester St, Winchester, VA 22601

  Classic 2100 square foot brick “American Foursquare” house in Winchester’s historic district. This very well maintained 1928 home was designed and built by “ole time” craftsmen who had an appreciation for solid, quality construction. What better way to spend wonderful lazy evenings or morning coffee than on the expansive 23-foot long front porch with a ceiling fan. This 4 bedroom, 2 bath home is

  Roger Lamborne MarketPlace REALTY

  17 E Leicester St, Winchester, VA 22601
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  $1,600 per month

  • 3 Beds
  • 1,040 Sq Ft
  • House for Rent

  209 Shenandoah Ave, Winchester, VA 22601

  Good Credit Score 650+/ Copy Credit Report must be provided by tenant. $40 per adult application processing fee.Deposit $1600 required.NO-PETS / NO SMOKERS Allowed. Lawn Care Included. Nice one floor ranch home 3 bedrooms and 1 bath walk-in shower fully remodeled. New heatpump installed 2025

  Barbara Gaul Jim Barb Realty, Inc.

  209 Shenandoah Ave, Winchester, VA 22601
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  $412,000 Sold Jul 23, 2025

  2320 Tower Ave, Winchester, VA 22601

  • 4 Beds
  • 2 Baths
  • 1,762 Sq Ft
  • Built 2006

  Last Sold Summary

  • $234/SF
  • 136 Days On Market

  Current Estimated Value $412,312

  Last Listing Agent Alex Adomako-Acheampong Samson Properties

  2320 Tower Ave, Winchester, VA 22601
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  Not Listed For Sale

  • 4 Beds
  • 3.5 Baths
  • 1,916 Sq Ft

  644 Hemsworth Ln, Winchester, VA 22601

  644 Hemsworth Ln, Winchester, VA 22601
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  $519,900 Under Contract

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

  216 Fairmont Ave, Winchester, VA 22601

  Classy colonial on the stately Fairmont Avenue with million dollar homes nearby, walking mall in close proximity with a plethora of boutique shops and eateries. The 2000 square feet is designed for comfort and coziness accented by 9ft ceilings, sunlit formal rooms, a well appointed kitchen, spacious bedrooms, adorable loft on 3rd level for a playroom/den/office, and the best part is entering your

  Dave Spence RE/MAX Roots

  216 Fairmont Ave, Winchester, VA 22601
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  $1,595 - $1,795 per month

  Fort Collier Terrace

  1 - 3 Beds

  900-1024 N Braddock St, Winchester, VA 22601

  Welcome to Fort Collier Terrace, an inviting community youll love being part of. Our apartments in Winchester, VA, come in one, two, and three-bedroom layouts that range from 800 to 1,000 square feet. Aside from the generous living quarters, youll find everything you need to feel right at home. Located near N Cameron Street and Martinsburg Pike, youre a stones throw away from the top dining,

  900-1024 N Braddock St, Winchester, VA 22601
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  $1,025,000 Sold Aug 01, 2025

  331 N Braddock St, Winchester, VA 22601

  • 5 Beds
  • 6 Baths
  • 6,517 Sq Ft
  • Built 1863

  Last Sold Summary

  • $157/SF
  • 36 Days On Market

  Last Listing Agent John Schroth Colony Realty

  331 N Braddock St, Winchester, VA 22601
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  Not Listed For Sale

  • 3 Beds
  • 2.5 Baths
  • 1,916 Sq Ft

  3138 Eton Place, Winchester, VA 22601

  3138 Eton Place, Winchester, VA 22601
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  $589,000

  • 3 Beds
  • 2 Baths
  • 1,974 Sq Ft

  832 Winder Ct, Winchester, VA 22601

  All-brick rancher located in the sought-after Early’s Green at Meadow Branch community, offering 1,974 finished square feet with 9-foot ceilings and true one-level living. The open floor plan provides excellent flow and is ideal for both everyday living and entertaining. Recent interior updates include new hardwood flooring in the main living room, new carpet in all bedrooms, and fresh interior

  Barton Chasler Realty ONE Group Old Towne

  832 Winder Ct, Winchester, VA 22601
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  $1,900 per month

  • 3 Beds
  • 3 Baths
  • 897 Sq Ft
  • Condo for Rent

  25 W Boscawen St Unit 2, Winchester, VA 22601

  High ceilings, light filled rooms, gorgeous wood floors, spacious rooms - and it's located in the heart of downtown. The walking mall is 1/2 block away and the parking garage around the corner. The second floor is all yours - you have to see this unit in person to really appreciate it.

  Teri Domanski Corcoran McEnearney

  25 W Boscawen St Unit 2, Winchester, VA 22601
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  $529,000 Sold Dec 04, 2025

  121 N Washington St, Winchester, VA 22601

  • 3 Beds
  • 2.5 Baths
  • 3,100 Sq Ft
  • Built 1807

  Last Sold Summary

  • $171/SF
  • 69 Days On Market

  Last Listing Agent M. Kelly Walker RE/MAX Roots

  121 N Washington St, Winchester, VA 22601
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  Est $967,668 Not Listed For Sale

  601 W Jubal Early Dr, Winchester, VA 22601

  601 W Jubal Early Dr, Winchester, VA 22601
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  $399,000 Pending

  • 4 Beds
  • 1.5 Baths
  • 1,953 Sq Ft

  318 E Piccadilly St, Winchester, VA 22601

  This delightful brick Colonial, perfectly situated in the heart of downtown Winchester, combines classic architecture with modern updates and an unbeatable location close to every downtown amenity, including restaurants, schools, shopping, parks, and major commuter routes. The home welcomes you with a large foyer featuring newly refinished hardwood floors that extend throughout the entire

  Dan Whitacre Colony Realty

  318 E Piccadilly St, Winchester, VA 22601
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  /22

  $1,450 - $1,800 per month

  Blue Ridge Apartments

  2 - 4 Beds

  2260 Wilson Blvd, Winchester, VA 22601

  Discover the perfect blend of comfort and convenience at Blue Ridge Apartments in Winchester, VA. Our recently updated homes feature a variety of floor plans. Nestled in a pet-friendly community, you're just minutes away from Winchester's scenic spots, historic downtown, Apple Blossom Mall, and major employers. With easy access to I-81 and Route 7, the best of Winchester is always within reach.

  2260 Wilson Blvd, Winchester, VA 22601
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  $110,000 Sold Sep 08, 2025

  116-118 W Leicester St, Winchester, VA 22601

  • Land
  • 0.12 Acre
  • $916,667 per Acre

  Last Sold Summary

  • 309 Days On Market

  Current Estimated Value $107,000

  Last Listing Agent Kim Hurst MarketPlace REALTY

  116-118 W Leicester St, Winchester, VA 22601
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  Not Listed For Sale

  • 3 Beds
  • 2.5 Baths
  • 1,918 Sq Ft

  3136 Eton Place, Winchester, VA 22601

  3136 Eton Place, Winchester, VA 22601
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  $469,999

  • 5 Beds
  • 3 Baths
  • 2,080 Sq Ft

  419 Summit Ave, Winchester, VA 22601

  Welcome Home!This beautifully renovated single-family home offers everything you need and more. Featuring hardwood floors throughout the main level, custom cabinets, and granite countertops in the kitchen, this home combines style and functionality. A new roof adds peace of mind, and the fully finished lower level provides additional living space for relaxation or entertainment. With 5

  Waqas Abbasi Lifestyle Realty, LLC.

  419 Summit Ave, Winchester, VA 22601
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  $2,500 per month

  • 4 Beds
  • 3.5 Baths
  • 1,920 Sq Ft
  • Townhouse for Rent

  1829 Harvest Dr, Winchester, VA 22601

  Brand new, pristine townhome, spacious end unit. Security system, featuring remote keyless entry and a video doorbell. Kitchen with stainless appliances and large island, opens to dining deck. Conveniently located with easy access to schools, hospital, shopping, services and major commuting thoroughfares. Landscaping maintenance and snow removal provided, city trash pick-up.

  Dallas Croft Samson Properties

  1829 Harvest Dr, Winchester, VA 22601
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  $600,000 Sold Mar 25, 2025

  229 S Pleasant Valley Rd, Winchester, VA 22601

  • Land
  • 3.69 Acres
  • $162,602 per Acre

  Last Sold Summary

  • 629 Days On Market

  Current Estimated Value $493,393

  Last Listing Agent Gillian Greenfield Coldwell Banker Premier

  229 S Pleasant Valley Rd, Winchester, VA 22601
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  Not Listed For Sale

  • 3 Beds
  • 2.5 Baths
  • 1,916 Sq Ft

  3142 Eton Place, Winchester, VA 22601

  3142 Eton Place, Winchester, VA 22601
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  $474,000

  • 3 Beds
  • 3 Baths
  • 2,805 Sq Ft

  407 Jefferson St, Winchester, VA 22601

  A TURN KEY classic colonial, fully UPDATED, and WALKABLE to downtown! *3 LEVELS totalling 2568 SF* Stroll to the restaurants in Old Town, enjoy the activities at Handley, or walk to the trails at MSV! NEW roof, HVAC, privacy fencing, custom paint and built-in cabinetry, plus new stainless steel appliances, including washer/dryer. Get creative in the FINISHED LOWER LEVEL with walk-out! Perhaps a

  Gillian Greenfield Coldwell Banker Premier

  407 Jefferson St, Winchester, VA 22601
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  $1,150 - $1,300 per month

  North Winchester Apartments

  1 - 2 Beds

  800 Thomas Ct, Winchester, VA 22601

  Now Leasing: 1 & 2 Bedroom Apartments Available Now! In-unit washer and dryerWater and garbage includedEnjoy a serene, peaceful settingDon't miss out—these are first come, first serve!

  800 Thomas Ct, Winchester, VA 22601
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  $400,000 Sold Oct 09, 2025

  225 Parkway St, Winchester, VA 22601

  • 4 Beds
  • 2 Baths
  • 2,256 Sq Ft
  • Built 1928

  Last Sold Summary

  • $177/SF
  • 13 Days On Market

  Current Estimated Value $401,436

  Last Listing Agent Tracy Jewell Samson Properties

  225 Parkway St, Winchester, VA 22601
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  /22

  Not Listed For Sale

  • 3 Beds
  • 2.5 Baths
  • 1,928 Sq Ft

  3146 Eton Place, Winchester, VA 22601

  3146 Eton Place, Winchester, VA 22601
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  $384,990 New Construction

  • 3 Beds
  • 4 Baths
  • 1,989 Sq Ft

  105 Boone Ct, Winchester, VA 22602

  Move in ready at Rossum Crossing townhome community, conveniently located near shopping and dining options. The St. Paul Townhome features three bedrooms, two and a half baths, and a one-car garage. The main floor boasts an open-concept floor plan, with a spacious family room that flows into a fully equipped kitchen. The kitchen includes an island, a pantry closet, and a breakfast nook. This

  Holly Horne Poole New Home Star Virginia, LLC

  105 Boone Ct, Winchester, VA 22602
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  $995 per month

  • 500 Sq Ft
  • Condo for Rent

  1816 Valley Ave Unit 3, Winchester, VA 22601

  We are okay with 6 months or Yearly lease.Freshly Remodeled Studio Apartment available. Centered in the heart of Winchester, walking distance to shops, restaurants, and entertainment. Utilities and WIFI are included at no charge. No pets allowed. Come and enjoy all of what Winchester has to offer. $995 per Month or $275 per Week. Handicap Ramp for easily access to the unit. On-site

  Raj Patel Ikon Realty - Ashburn

  1816 Valley Ave Unit 3, Winchester, VA 22601
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  $370,000 Sold Nov 14, 2025

  613 Laurelwood Cir, Winchester, VA 22601

  • 3 Beds
  • 2.5 Baths
  • Built 2025

  Last Sold Summary

  • 35 Days On Market

  Last Listing Agent Dev Patel Samson Properties

  613 Laurelwood Cir, Winchester, VA 22601
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  /22

  Not Listed For Sale

  • 3 Beds
  • 2.5 Baths
  • 2,074 Sq Ft

  3132 Eton Place, Winchester, VA 22601

  3132 Eton Place, Winchester, VA 22601
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  $429,900

  • 3 Beds
  • 2 Baths
  • 2,219 Sq Ft

  945 Allen Dr, Winchester, VA 22601

  945 Allen Drive sits on a rare extra-wide double lot and showcases an in-ground swimming pool designed for both fun and relaxation. The pool features a brand-new liner, solar-powered heater to help keep the water comfortably warm, a sun shelf for lounging in shallow water, and a diving board for classic summer fun. The backyard is fully enclosed with a 6-foot vinyl privacy fence, creating a

  Barton Chasler Realty ONE Group Old Towne

  945 Allen Dr, Winchester, VA 22601
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  $500 - $2,000 per month

  Brookfield Corporate Apartments

  1 - 2 Beds

  548 Brookfield Dr, Winchester, VA 22601

  We are excited to share that we are under new ownership and management, and we're eager to welcome new guests to our community.Located at 500 Brookfield Drive, Winchester, VA 22601, Brookfield Corporate Apartments offers spacious, fully furnished one and two-bedroom apartments. Each apartment is designed with your comfort in mind and comes equipped with linens, kitchenware, two TVs with

  548 Brookfield Dr, Winchester, VA 22601
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  $585,000 Sold Aug 07, 2025

  720 Beehive Way, Winchester, VA 22601

  • 4 Beds
  • 3.5 Baths
  • 2,571 Sq Ft
  • Built 2006

  Last Sold Summary

  • $228/SF
  • 53 Days On Market

  Current Estimated Value $591,567

  Last Listing Agent Amy Emerson-Kerns Cambridge Premier Realty, LLC.

  720 Beehive Way, Winchester, VA 22601
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  Est $474,591 Not Listed For Sale

  • 4 Beds
  • 2.5 Baths
  • 1,776 Sq Ft

  2060 Taylor Grace Ct, Winchester, VA 22601

  2060 Taylor Grace Ct, Winchester, VA 22601
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  $389,990 New Construction

  • 3 Beds
  • 4 Baths
  • 1,989 Sq Ft

  117 Boone Ct, Winchester, VA 22602

  Immediate Move-in at Rossum Crossing! Winchester's newest and most popular townhome community, conveniently located near shopping and dining options. The St. Paul Townhome features three bedrooms, two and a half baths, and a one-car garage. The main floor boasts an open-concept floor plan, with a spacious family room that flows into a fully equipped kitchen. The kitchen includes an island, a

  Holly Horne Poole New Home Star Virginia, LLC

  117 Boone Ct, Winchester, VA 22602
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  $1,400 per month

  • 2 Beds
  • 1 Bath
  • 600 Sq Ft
  • Condo for Rent

  447 N Loudoun St, Winchester, VA 22601

  Gorgeous two bedroom apartment 2 blocks from Old Town Winchester walking mall! Live the city lifestyle in an old Victorian set in a park-like atmosphere with picnic area and a private entrance to your space. The apartment features wide plank hardwood flooring and original trim throughout, a large living room with gas fireplace, and pocket doors. The largest bedroom has an en suite and huge

  Misty Weaver Samson Properties

  447 N Loudoun St, Winchester, VA 22601
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  $565,000 Sold May 21, 2025

  2532 Middle Rd, Winchester, VA 22601

  • 4 Beds
  • 3 Baths
  • 2,108 Sq Ft
  • Built 2022

  Last Sold Summary

  • $268/SF

  Current Estimated Value $588,617

  Last Listing Agent Sarah Reynolds Keller Williams Realty

  2532 Middle Rd, Winchester, VA 22601
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  Est $586,689 Not Listed For Sale

  • 4 Beds
  • 3.5 Baths
  • 3,568 Sq Ft

  2044 Taylor Grace Ct, Winchester, VA 22601

  2044 Taylor Grace Ct, Winchester, VA 22601
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  $375,900 Under Contract

  • 3 Beds
  • 2.5 Baths
  • 1,728 Sq Ft

  2116 Stoneleigh Dr, Winchester, VA 22601

  New roof and decking make this Orchard Hill town home a great buy—Hardwood floors, a fireplace in the family room, along with built-in cabinets and bookshelves: full walk-out basement and large yard.

  John Schroth Colony Realty

  2116 Stoneleigh Dr, Winchester, VA 22601
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  $1,600 - $1,800 per month

  Apartment for Rent

  1 - 2 Beds

  148 N Loudoun St, Winchester, VA 22601

  Beautiful 1 and 2 bedroom fully furnished apartments. Located directly on the old town walking mall. Washer dryer included in the unit. On site parking.

  148 N Loudoun St, Winchester, VA 22601
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  $420,000 Sold Nov 14, 2025

  2808 Saratoga Dr, Winchester, VA 22601

  • 3 Beds
  • 2 Baths
  • 2,018 Sq Ft
  • Built 2002

  Last Sold Summary

  • $208/SF
  • 24 Days On Market

  Last Listing Agent Dave Spence RE/MAX Roots

  2808 Saratoga Dr, Winchester, VA 22601
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  Est $392,798 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,632 Sq Ft

  444 Superior Ave, Winchester, VA 22601

  444 Superior Ave, Winchester, VA 22601

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