12,854

Winchester County, VA Homes

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  • /15

    $399,480

    New Construction Pending
    • 3 Beds
    • 4 Baths
    • 1,966 Sq Ft

    103 Marlow Ct, Winchester, VA 22602

    Rossum Crossing is Winchester's newest townhome community, which is located near shopping and dining. The St. Paul Townhome features 3 bedrooms, 2 1/2 baths, and a one-car garage. The main floor has an open-concept floorplan with a spacious family room that leads to a fully equipped kitchen. The kitchen has an island, pantry closet, and breakfast nook. This level also has a powder room. You can

    Dick Bryan New Home Star Virginia, LLC

    103 Marlow Ct, Winchester, VA 22602
  • /16

    $2,099

    Total Monthly Price

    • 3 Beds
    • 2.5 Baths
    • 1,464 Sq Ft
    • Townhouse for Rent

    2027 Harvest Dr, Winchester, VA 22601

    Discover comfort and convenience in this beautifully updated 3-bedroom, 2.5-bathroom townhome, ideally situated on a desirable corner lot. This home offers a spacious layout perfect for modern living. Enjoy the privacy of a fenced backyard, ideal for relaxing or entertaining. With two driveways and a garage, parking is never an issue. The large laundry room adds extra functionality, while the

    2027 Harvest Dr, Winchester, VA 22601
  • /28

    $304,900

    Sold Oct 02, 2025

    2923 S Pleasant Valley Rd, Winchester, VA 22601

    • 3 Beds
    • 1 Bath
    • 858 Sq Ft
    • Built 1961

    Last Sold Summary

    • $355/SF
    • 3 Days On Market

    Current Estimated Value $319,947

    Last Listing Agent Anna Fox NextHome Realty Select

    2923 S Pleasant Valley Rd, Winchester, VA 22601
    • /71

      Est $341,476

      Not Listed For Sale

      517 Armour Dale, Winchester, VA 22601

      • 4 Beds
      • 2.5 Baths
      • 1,600 Sq Ft
      • Built 1935
      517 Armour Dale, Winchester, VA 22601

      Last Sold Summary

      • 3 Days On Market

      Last Listing Agent John Ashton Equity Realty

  • /33

    $348,000

    $12K PRICE DROP
    • 3 Beds
    • 2 Baths
    • 1,554 Sq Ft

    302 Wentworth Dr, Winchester, VA 22601

    Enjoy one-level living in this spectacularly located brick rambler, nestled in a quiet residential neighborhood while remaining conveniently close to Route 11 with easy access to I-81. The property currently has a long term month-to-month tenant paying under market value, offering flexibility for an owner-occupant or an investor seeking rental income with potential for increased rent. Situated on

    Heloisa Amar Samson Properties

    302 Wentworth Dr, Winchester, VA 22601
  • /6

    $1,350 Per Month

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

    4 W Cork St Unit 1, Winchester, VA 22601

    Welcome to Apt. 1 at 4 W. Cork Street, a beautifully located residence in the heart of historic downtown Winchester. This inviting apartment offers the perfect blend of character, convenience, and city living. Enjoy easy access to local restaurants, coffee shops, boutiques, entertainment, and the vibrant Old Town walking mall—all just steps from your front door.

    Patrick Slate Keller Williams Realty

    4 W Cork St Unit 1, Winchester, VA 22601
  • /28

    $300,000

    Sold Mar 26, 2026

    501 Battle Ave, Winchester, VA 22601

    • 3 Beds
    • 1 Bath
    • 1,789 Sq Ft
    • Built 1946

    Last Sold Summary

    • $168/SF
    • 28 Days On Market

    Current Estimated Value $307,791

    Last Listing Agent Susan Caulfield Pearson Smith Realty, LLC

    501 Battle Ave, Winchester, VA 22601
    • /46

      Est $531,975

      Not Listed For Sale

      605 Kernstown Ct, Winchester, VA 22601

      • 4 Beds
      • 2.5 Baths
      • 2,568 Sq Ft
      • Built 1997
      605 Kernstown Ct, Winchester, VA 22601

      Last Sold Summary

      • 14 Days On Market

      Last Listing Agent Omar Gonzalez RLAH @properties

  • /35

    $675,000

    • 3 Beds
    • 2.5 Baths
    • 1,650 Sq Ft

    112 W Germain St, Winchester, VA 22601

    100-Year-Old Downtown Winchester Charmer – Fully Reimagined in 2025!This stunning, fully restored century-old home seamlessly blends historic charm with high-end modern upgrades in the heart of downtown Winchester. Completely taken down to the studs and rebuilt in 2025, every detail was thoughtfully executed—nothing was overlooked. Proudly recognized with the 2025 Preservation of Historic

    Amanda Magana RE/MAX Roots

    112 W Germain St, Winchester, VA 22601
  • /17

    $1,995

    Total Monthly Price

    • 3 Beds
    • 1 Bath
    • 1,296 Sq Ft
    • House for Rent

    712 S Cameron St, Winchester, VA 22601

    Nice home just a few blocks from downtown Winchester! This 3 bedroom 1 bath has spacious rooms, refinished hardwood floors throughout, a full basement with W/D hookups and extra storage, warm gas heat and window ac units, nice front and back porch and large backyard. This home is pet friendly (under 40lbs with additional fee per pet). Get your application in today on this great little home in the

    712 S Cameron St, Winchester, VA 22601
  • /35

    $334,900

    Sold Nov 25, 2025

    2225 Harrison St, Winchester, VA 22601

    • 3 Beds
    • 2 Baths
    • 1,300 Sq Ft
    • Built 1955

    Last Sold Summary

    • $258/SF
    • 42 Days On Market

    Current Estimated Value $333,116

    Last Listing Agent Jim Stafford ERA Oakcrest Realty, Inc.

    2225 Harrison St, Winchester, VA 22601
    • /38

      Est $530,725

      Not Listed For Sale

      3022 Saratoga Dr, Winchester, VA 22601

      • 4 Beds
      • 3 Baths
      • 2,312 Sq Ft
      • Built 2000
      3022 Saratoga Dr, Winchester, VA 22601

      Last Sold Summary

      • 42 Days On Market

      Last Listing Agent Brett Sowder RE/MAX Roots

  • /32

    $399,900

    $29K PRICE DROP
    • 2 Beds
    • 2 Baths
    • 1,419 Sq Ft

    118 1/2 E Cork St, Winchester, VA 22601

    Seeking the perfect blend of historic character and modern urban living? This exceptional Urban Lofts Condominium is just one and a half blocks from Old Town Winchester Walking Mall, offering easy access to restaurants, boutiques, entertainment, and vibrant downtown living. Originally built in the early 1900s, this beautifully updated home showcases exposed brick walls, timeless architectural

    Janet Flaherty Keller Williams Realty

    118 1/2 E Cork St, Winchester, VA 22601
  • /14

    $1,350 Per Month

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

    220 E Whitlock Ave, Winchester, VA 22601

    Conveniently located near Downtown Winchester, Shenandoah University, shopping, restaurants, and other everyday amenities, this well-maintained 2-bedroom, 1-bath townhome offers comfortable living with plenty of functional space. The main and upper levels feature hardwood flooring, while the eat-in kitchen has durable vinyl flooring. Exceptional closet space throughout the home provides abundant

    Meghan Pachas MAP Property Solutions, LLC.

    220 E Whitlock Ave, Winchester, VA 22601
  • /66

    $685,000

    Sold Oct 29, 2025

    2530 Goldenfield Ln, Winchester, VA 22601

    • 4 Beds
    • 5 Baths
    • 5,903 Sq Ft
    • Built 2005

    Last Sold Summary

    • $116/SF
    • 21 Days On Market

    Current Estimated Value $745,652

    Last Listing Agent Dave Spence RE/MAX Roots

    2530 Goldenfield Ln, Winchester, VA 22601
    • /59

      Est $584,521

      Not Listed For Sale

      3026 Saratoga Dr, Winchester, VA 22601

      • 4 Beds
      • 2.5 Baths
      • 3,379 Sq Ft
      • Built 1998
      3026 Saratoga Dr, Winchester, VA 22601

      Last Sold Summary

      • 3 Days On Market

      Last Listing Agent Stephanie Ryall Realty ONE Group Old Towne

  • /2

    $180,000

    • 3 Beds
    • 1 Bath
    • 1,054 Sq Ft

    309 Liberty Ave, Winchester, VA 22601

    Opportunity awaits at 309 Liberty Avenue in Winchester City. This classic Cape Cod offers the chance to create something truly special in an area experiencing continued growth, infrastructure improvements, and neighborhood investment. The property does require substantial work, making cash financing the most likely option; however, the potential is significant for a buyer with the vision to

    Rick Guthrie Keller Williams Realty

    309 Liberty Ave, Winchester, VA 22601
  • /31

    $1,995

    Total Monthly Price

    • 2 Beds
    • 2 Baths
    • 850 Sq Ft
    • Condo for Rent

    2253 Papermill Rd, Winchester, VA 22601

    Modern Luxury Meets Ultimate Convenience! Welcome to this sophisticated 2BR/2BA main-level apartment for a premium living experience. The heart of the home is a stunning, open-concept chef’s kitchen featuring crisp white cabinetry, elegant white quartz countertops, and a massive kitchen island.Designed for effortless living, the entire unit is situated on a single level (no stairs!), including

    2253 Papermill Rd, Winchester, VA 22601
  • /97

    $1,014,300

    Sold Jul 17, 2026

    217 W Boscawen St, Winchester, VA 22601

    • 6 Beds
    • 5 Baths
    • 6,682 Sq Ft
    • Built 1840

    Last Sold Summary

    • 15% Below List Price
    • $152/SF
    • 57 Days On Market

    Current Estimated Value $1,153,063

    Last Listing Agent Gillian Greenfield Coldwell Banker Premier

    217 W Boscawen St, Winchester, VA 22601
    • /43

      Est $446,378

      Not Listed For Sale

      2817 Broadview St, Winchester, VA 22601

      • 3 Beds
      • 2 Baths
      • 2,355 Sq Ft
      • Built 1955
      2817 Broadview St, Winchester, VA 22601

      Last Sold Summary

      • 47 Days On Market

      Last Listing Agent LESLIE WEBB Long & Foster Real Estate, Inc.

  • /70

    $735,000

    $15K PRICE DROP Under Contract
    • 6 Beds
    • 4 Baths
    • 4,672 Sq Ft

    817 Chelsea Dr, Winchester, VA 22601

    Spacious 5-6-bedroom, 4-bath brick-front rancher with a fully finished basement, offering flexible living space for today’s needs. The main level features a welcoming living room with a tray ceiling & a gas fireplace, a formal dining room with crown molding & chair rail, and a well-appointed kitchen with Corian countertops and a walk-in pantry. The primary suite is conveniently located on the

    Sheila Pack RE/MAX Roots

    817 Chelsea Dr, Winchester, VA 22601
  • /21

    $1,350 Per Month

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

    116 N Indian Aly Unit 102, Winchester, VA 22601

    Live, work, and play in the heart of Historic Downtown Winchester! Be the first to enjoy this beautifully renovated lower-level 1-bedroom, 1-bathroom apartment, ideally located on Indian Alley directly across from the Braddock Street Parking Garage and just steps from the Old Town Walking Mall's shops, restaurants, breweries, and entertainment. Freshly updated throughout, this apartment features

    Chris Roszko Colony Realty

    116 N Indian Aly Unit 102, Winchester, VA 22601
  • /54

    $445,000

    Sold Jun 11, 2026

    413 George St, Winchester, VA 22601

    • 3 Beds
    • 2.5 Baths
    • 1,938 Sq Ft
    • Built 1989

    Last Sold Summary

    • $230/SF
    • 27 Days On Market

    Current Estimated Value $446,147

    Last Listing Agent Shannon Jones Pearson Smith Realty, LLC

    413 George St, Winchester, VA 22601
    • /33

      Est $428,474

      Not Listed For Sale

      417 Circle Dr, Winchester, VA 22601

      • 3 Beds
      • 2 Baths
      • 1,366 Sq Ft
      • Built 2023
      417 Circle Dr, Winchester, VA 22601

      Last Sold Summary

      • 120 Days On Market

      Last Listing Agent Vihang Nair EXP Realty, LLC

  • /4

    $750,000

    Pending
    • Land
    • 1.33 Acres
    • $563,910 per Acre

    903 N Loudoun St, Winchester, VA 22601

    Lot 2 is half in Winchester City (tax ID # 134003-35) at 903 N. Loudoun St., & half in Frederick County (tax ID #54-A-50.) Mixed use zoning HR & B2. The county side has a brick residential structure, address 909 Martinsburg Pk, and city half is cleared land/ lot. The total sq ftg is 108,325 (2 & half acres.) Road frontage on Loudoun & Martinsburg PIke is 250 feet. The rear of lot is North

    Wendy Longerbeam Coldwell Banker Elite

    903 N Loudoun St, Winchester, VA 22601
  • /50

    $1,495

    Total Monthly Price

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

    2545 Bradford Ct, Winchester, VA 22601

    The Flats of Winchester is an SDF Residential community located in Winchester, VA, offering a blend of renovated 1- and 2-bedroom apartments. The property features front patio gardens throughout, along with a unique landscape that sets it apart from other apartment complexes while preserving the quaint charm of the surrounding communityYour new home comes freshly remodeled and equipped

    2545 Bradford Ct, Winchester, VA 22601
  • /51

    $450,000

    Sold Nov 21, 2025

    609 Crystal Ct, Winchester, VA 22601

    • 4 Beds
    • 2.5 Baths
    • 2,868 Sq Ft
    • Built 1990

    Last Sold Summary

    • $157/SF
    • 31 Days On Market

    Current Estimated Value $476,941

    Last Listing Agent Tiffany Hunter ERA Oakcrest Realty, Inc.

    609 Crystal Ct, Winchester, VA 22601
    • /35

      Est $382,116

      Not Listed For Sale

      416 Superior Ave, Winchester, VA 22601

      • 4 Beds
      • 1.5 Baths
      • 2,508 Sq Ft
      • Built 1965
      416 Superior Ave, Winchester, VA 22601

      Last Sold Summary

      • 6 Days On Market

      Last Listing Agent Jeanne Mezzatesta Colony Realty

  • /69

    $650,000

    Open Sat 11AM - 1PM
    • 4 Beds
    • 3.5 Baths
    • 4,179 Sq Ft

    1529 Dalton Place, Winchester, VA 22601

    Welcome to 1529 Dalton Place, an exceptional home tucked away on a quiet cul-de-sac in one of Winchester's most desirable locations. Offering 4 spacious bedrooms, 3.5 bathrooms, and an expansive floor plan, this beautifully designed residence delivers the perfect blend of comfort, style, and functionality. From the moment you enter, you'll appreciate the generous room sizes throughout, including

    RoxAnn Grimes RE/MAX Roots

    1529 Dalton Place, Winchester, VA 22601
  • /9

    $1,750 Per Month

    • 3 Beds
    • 1 Bath
    • 1,021 Sq Ft
    • House for Rent

    1112 Opequon Ave, Winchester, VA 22601

    Great home close to city park and recreation, Shenandoah University, gas station, post office, restaurants... This house is being freshly painted and ready for the new tenant. No smoking/vaping at the property. Required: tenant(s) to have 660+ credit score, job stability, tenant's monthly income equal to 4+ times the amount of monthly rent, RentSpree application required.

    Elcy Pereira Elcy & Co. Realty, LLC.

    1112 Opequon Ave, Winchester, VA 22601
  • /55

    $640,000

    Sold Mar 16, 2026

    501 Jefferson St, Winchester, VA 22601

    • 5 Beds
    • 2.5 Baths
    • 3,420 Sq Ft
    • Built 1988

    Last Sold Summary

    • 1% Below List Price
    • $187/SF
    • 16 Days On Market

    Current Estimated Value $664,653

    Last Listing Agent Jeanne Mezzatesta Colony Realty

    501 Jefferson St, Winchester, VA 22601
    • /20

      Est $421,711

      Not Listed For Sale

      2812 Baldwin St, Winchester, VA 22601

      • 3 Beds
      • 2 Baths
      • 2,262 Sq Ft
      • Built 1956
      2812 Baldwin St, Winchester, VA 22601

      Last Sold Summary

      • 93 Days On Market

      Last Listing Agent Jennifer Sacco RE/MAX Roots

  • /89

    $539,000

    Open Sat 11AM - 12PM $71K PRICE DROP
    • 3 Beds
    • 3.5 Baths
    • 3,140 Sq Ft

    1202 Handley Ave, Winchester, VA 22601

    Nestled on one of Winchester's most sought-after streets, this distinctive mid-century contemporary home offers a rare blend of character, space, and convenience just moments from downtown dining, shopping, and entertainment. Designed for comfortable main-level living, the home combines timeless architectural appeal with thoughtful functionality. The main level features a spacious primary suite

    Leah Marabella Realty ONE Group Old Towne

    1202 Handley Ave, Winchester, VA 22601
  • /17

    $2,149

    Total Monthly Price

    • 3 Beds
    • 1 Bath
    • 1,648 Sq Ft
    • House for Rent

    122 Morningside Dr, Winchester, VA 22601

    This home Features 3 bedrooms - 1 full bath. Finished attic for possibility for an additional bedroom or use as office space or rec room. Unfinished basement for lots of storage. Rear deck. Off street parking. No Cats, Dogs case by case with non-refundable pet deposit.$50 application fee per applicant.Oil HeatApply online at None

    122 Morningside Dr, Winchester, VA 22601
  • /67

    $549,000

    Sold Jun 26, 2026

    1930 Harvest Dr, Winchester, VA 22601

    • 3 Beds
    • 2.5 Baths
    • 2,450 Sq Ft
    • Built 2003

    Last Sold Summary

    • 4% Below List Price
    • $224/SF
    • 37 Days On Market

    Current Estimated Value $551,657

    Last Listing Agent Dan Whitacre Colony Realty

    1930 Harvest Dr, Winchester, VA 22601
    • /80

      Est $462,941

      Not Listed For Sale

      2820 Baldwin St, Winchester, VA 22601

      • 5 Beds
      • 3 Baths
      • 3,128 Sq Ft
      • Built 1965
      2820 Baldwin St, Winchester, VA 22601

      Last Sold Summary

      • 9 Days On Market

      Last Listing Agent Carolina Mosquera Weichert, REALTORS

  • /50

    $380,000

    Pending
    • 4 Beds
    • 2 Baths
    • 1,785 Sq Ft

    419 van Fossen St, Winchester, VA 22601

    . Vintage 1950's Build, In The City of Winchester. Perfect City living, across from Virginia Avenue Elementary and Post Office! Walking Distance from Old Town Winchester VA!. Blocks from grocery stores, gas stations, bus stops, shopping, City transit and just of I 81 and Rt 7 for easy commuting ! This 4 Bedroom, 1 and half bath Cape Cod is spacious and ready for the new owner! The curb appeal is

    Tracy Link Coldwell Banker Premier

    419 van Fossen St, Winchester, VA 22601
  • /25

    $1,800 Per Month

    • 2 Beds
    • 2 Baths
    • 1,382 Sq Ft
    • House for Rent

    31 E Germain St, Winchester, VA 22601

    Nestled in the heart of Winchester City’s Historic District and walkable to shops and restaurants, this charming 2-bedroom, 2-bathroom gem is a rare find! The large front porch has great curb appeal and is the perfect place for outdoor lounging. The home is filled with natural light that illuminates the clean white walls and warm hardwood flooring. The living room flows into the dedicated dining

    Rachel Olsen Keller Williams Realty

    31 E Germain St, Winchester, VA 22601
  • /58

    $285,000

    Sold May 13, 2026

    301 Shawnee Ave, Winchester, VA 22601

    • 4 Beds
    • 1.5 Baths
    • 1,449 Sq Ft
    • Built 1940

    Last Sold Summary

    • 2% Above List Price
    • $197/SF
    • 4 Days On Market

    Current Estimated Value $284,991

    Last Listing Agent Barton Chasler Realty ONE Group Old Towne

    301 Shawnee Ave, Winchester, VA 22601
    • /71

      Est $988,161

      Not Listed For Sale

      304 Longview Ln, Winchester, VA 22602

      • 5 Beds
      • 3 Baths
      • 4,700 Sq Ft
      • Built 1993
      304 Longview Ln, Winchester, VA 22602

      Last Sold Summary

      • 10 Days On Market

      Last Listing Agent Pamela Foltz Realty ONE Group Old Towne

Showing Results 241 - 280, Page 7 of 18

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