12,855

Winchester County, VA Homes

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  • /17

    $199,900

    $15K PRICE DROP
    • Land
    • 15,681 Sq Ft
    • $555,278 per Acre

    506 Fairmont Ave, Winchester, VA 22601

    NEW CITY LOT! This newly configured lot in the heart of downtown Winchester has been expanded and is ready for you to build your dream home. Featuring a width of approximately 100 feet, you have plenty of space to accommodate nearly any home of your choice. As a bonus, the driveway will be on the neighboring lot, which allows even more buildable space. Additionally, you do not have to worry about

    Dan Whitacre Colony Realty

    506 Fairmont Ave, Winchester, VA 22601
  • /20

    $2,495

    Total Monthly Price

    • 4 Beds
    • 2 Baths
    • 1,585 Sq Ft
    • House for Rent

    332 Shawnee Ave, Winchester, VA 22601

    Updated Photos Coming Soon Don't miss this beautiful 4 Bedroom 2 Bath home nestled on a quite street just minutes from everything. This home offers spacious rooms, large bedroom on the main level, washer and dryer hook up, full unfinished basement, large yard and an alley that offers off street parking. New kitchen cabinets, counter tops, appliances, hardwood floors throughout the main

    332 Shawnee Ave, Winchester, VA 22601
  • /47

    $555,000

    Sold Dec 22, 2025

    2307 Stoneridge Rd, Winchester, VA 22601

    • 5 Beds
    • 3.5 Baths
    • 3,280 Sq Ft
    • Built 2016

    Last Sold Summary

    • $169/SF
    • 5 Days On Market

    Current Estimated Value $583,045

    Last Listing Agent Dave Spence RE/MAX Roots

    2307 Stoneridge Rd, Winchester, VA 22601
    • /26

      Est $423,156

      Not Listed For Sale

      444 Superior Ave, Winchester, VA 22601

      • 3 Beds
      • 2 Baths
      • 1,632 Sq Ft
      • Built 2008
      444 Superior Ave, Winchester, VA 22601

      Last Sold Summary

      • 28 Days On Market

      Last Listing Agent Kathryn Symenow CENTURY 21 New Millennium

  • /127

    $3,175,000

    • 6 Beds
    • 7 Baths
    • 8,593 Sq Ft

    730 Merrimans Ln, Winchester, VA 22601

    A Once-in-a-Generation Opportunity: 1765 Heritage Meets Modern LuxuryRarely does a property of this caliber, history, and scale become available within Winchester city limits. Perfectly positioned on 5.49 acres of breathtaking, park-like grounds, this historic masterpiece is a true private oasis. Painstakingly and lovingly renovated, the estate offers an unparalleled blend of 18th-century

    Justin Mistretta Berkshire Hathaway HomeServices PenFed Realty

    730 Merrimans Ln, Winchester, VA 22601
  • /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
  • /44

    $438,000

    Sold May 08, 2026

    21 W Pall Mall St, Winchester, VA 22601

    • 4 Beds
    • 2.5 Baths
    • 1,805 Sq Ft
    • Built 1930

    Last Sold Summary

    • 3% Above List Price
    • $243/SF
    • 10 Days On Market

    Current Estimated Value $421,230

    Last Listing Agent Allyson Lenz Compass

    21 W Pall Mall St, Winchester, VA 22601
    • /24

      Est $428,233

      Not Listed For Sale

      428 Superior Ave, Winchester, VA 22601

      • 4 Beds
      • 3 Baths
      • 2,288 Sq Ft
      • Built 1967
      428 Superior Ave, Winchester, VA 22601

      Last Sold Summary

      • 4 Days On Market

      Last Listing Agent Devin Moore Innovation Properties, LLC

  • /52

    $530,000

    • 5 Beds
    • 3.5 Baths
    • 2,417 Sq Ft

    1605 Fort Braddock Ct, Winchester, VA 22601

    Fort Braddock Heights (Winchester City) - Detached Two-Level Home with Five (5) Bedrooms + Three (3) Full Bathrooms + One (1) Half Bathroom *Approx. 2,417 Finished Square Feet Across Two (2) Levels *Built 1992 *0.23 Acre Lot (Approx. 10,019 Square Feet) *One (1) Car Attached Front-Loading Garage + Paved Driveway *Second Garage Bay Converted to Oversized Main Level Laundry and Storage with Bonus

    Timothy Kotlowski Long & Foster Real Estate, Inc.

    1605 Fort Braddock Ct, Winchester, VA 22601
  • /5

    $1,295

    Total Monthly Price

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

    129 Holiday Dr Unit 1, Winchester, VA 22601

    BEST DEAL IN TOWN!! Get your application in today, these apartments don't last long! You get one level living with 2 bedroom and 1 full bathroom. This apartment will have a fully updated kitchen, complete with new cabinets and countertops, above the range microwave, new vinyl in the kitchen and bath and new carpet in the bedrooms. There is an onsite coin operated laundry facility, off street

    129 Holiday Dr Unit 1, Winchester, VA 22601
  • /46

    $506,000

    Sold May 13, 2026

    312 W Cecil St, Winchester, VA 22601

    • 3 Beds
    • 1.5 Baths
    • 1,698 Sq Ft
    • Built 1915

    Last Sold Summary

    • 3% Above List Price
    • $298/SF
    • 5 Days On Market

    Current Estimated Value $487,995

    Last Listing Agent Jeanne Mezzatesta Colony Realty

    312 W Cecil St, Winchester, VA 22601
    • /43

      Est $433,543

      Not Listed For Sale

      441 Superior Ave, Winchester, VA 22601

      • 2 Beds
      • 2 Baths
      • 1,672 Sq Ft
      • Built 1998
      441 Superior Ave, Winchester, VA 22601

      Last Sold Summary

      • 1 Day On Market

      Last Listing Agent Curtis Siever NextHome Realty Select

  • /26

    $325,000

    • 3 Beds
    • 1.5 Baths
    • 1,248 Sq Ft

    2817 Papermill Rd, Winchester, VA 22601

    Welcome to 2817 Papermill Road, a beautifully maintained home that reflects true pride of ownership from the moment you arrive. Situated on an impressive approximately 0.35-acre lot, this property offers a wonderful combination of space, comfort, and convenience all while being just minutes from everything Winchester has to offer. The home has been thoughtfully cared for and kept in excellent

    Kevin Rodriguez Weichert, REALTORS

    2817 Papermill Rd, Winchester, VA 22601
  • /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
  • /48

    $580,000

    Sold Aug 20, 2026

    608 Bellview Ave, Winchester, VA 22601

    • 4 Beds
    • 2.5 Baths
    • 3,328 Sq Ft
    • Built 1974

    Last Sold Summary

    • $174/SF
    • 3 Days On Market

    Current Estimated Value $584,815

    Last Listing Agent Kevin LaRue Century 21 Redwood Realty

    608 Bellview Ave, Winchester, VA 22601
    • /39

      Est $379,633

      Not Listed For Sale

      417 Superior Ave, Winchester, VA 22601

      • 3 Beds
      • 1.5 Baths
      • 1,747 Sq Ft
      • Built 1964
      417 Superior Ave, Winchester, VA 22601

      Last Sold Summary

      • 79 Days On Market

      Last Listing Agent Bruce Elsey Long & Foster Real Estate, Inc.

  • /96

    $459,999

    $30K PRICE DROP
    • 5 Beds
    • 3 Baths
    • 1,887 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 spacious

    Waqas Abbasi Lifestyle Realty, LLC.

    419 Summit Ave, Winchester, VA 22601
  • /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
  • /31

    $325,000

    Sold Dec 30, 2025

    414 Elm St, Winchester, VA 22601

    • 4 Beds
    • 2 Baths
    • 915 Sq Ft
    • Built 1960

    Last Sold Summary

    • $355/SF
    • 109 Days On Market

    Current Estimated Value $322,454

    Last Listing Agent Aracely Rivera First Decision Realty LLC

    414 Elm St, Winchester, VA 22601
    • /54

      Est $365,032

      Not Listed For Sale

      444 Imperial St, Winchester, VA 22601

      • 3 Beds
      • 2 Baths
      • 1,221 Sq Ft
      • Built 1959
      444 Imperial St, Winchester, VA 22601

      Last Sold Summary

      • 43 Days On Market

      Last Listing Agent Alexandra Brown Spring Hill Real Estate, LLC.

  • /17

    $396,190

    New Construction
    • 4 Beds
    • 3.5 Baths
    • 1,889 Sq Ft

    660 Arden Ct, Winchester, VA 22601

    660 Arden Court is an attractive new 3 level townhome with brick backing to trees in Winchester's premier Meadow Branch community for September move-in. Our modern Adams floorplan features a 1-car garage, and a bedroom and full bathroom on the first floor. The main level with LVP Floors features a kitchen equipped with beautiful Quartz countertops, white cabinets, and stainless-steel appliances.

    D.R. Horton Builder
    660 Arden Ct, Winchester, VA 22601
  • /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
  • /33

    $220,000

    Sold Aug 27, 2026

    554 N Kent St, Winchester, VA 22601

    • 3 Beds
    • 1 Bath
    • 924 Sq Ft
    • Built 1964

    Last Sold Summary

    • 4% Below List Price
    • $238/SF
    • 8 Days On Market

    Current Estimated Value $229,319

    Last Listing Agent Leah Clowser RE/MAX Roots

    554 N Kent St, Winchester, VA 22601
    • /14

      Est $405,561

      Not Listed For Sale

      3128 Papermill Rd, Winchester, VA 22601

      • 3 Beds
      • 3 Baths
      • 1,970 Sq Ft
      • Built 2002
      3128 Papermill Rd, Winchester, VA 22601

      Last Sold Summary

      • 9 Days On Market

      Last Listing Agent Natalie Dalecky ERA Oakcrest Realty, Inc.

  • /71

    $735,000

    • 3 Beds
    • 2.5 Baths
    • 2,572 Sq Ft

    1748 Handley Ave, Winchester, VA 22601

    Exceptional space, thoughtful updates, and tremendous future potential come together in this impressive home! With a brand-new HVAC system, freshly painted interior and exterior, a freshly painted deck, and beautifully refreshed hardwood floors in the living room, much of the work has already been done for the next owner. Seller has obtained a recent professional appraisal; contact listing agent

    Barbara Smith RE/MAX Real Estate Connections

    1748 Handley Ave, Winchester, VA 22601
  • /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
  • /26

    $369,000

    Sold Sep 03, 2026

    614 Sherlock Trace, Winchester, VA 22601

    • 3 Beds
    • 2.5 Baths
    • 1,737 Sq Ft
    • Built 2003

    Last Sold Summary

    • $212/SF
    • 56 Days On Market

    Current Estimated Value $374,013

    Last Listing Agent Carlos Soares Samson Properties

    614 Sherlock Trace, Winchester, VA 22601
    • /68

      Est $411,273

      Not Listed For Sale

      3020 Papermill Rd, Winchester, VA 22601

      • 4 Beds
      • 2 Baths
      • 2,902 Sq Ft
      • Built 1961
      3020 Papermill Rd, Winchester, VA 22601

      Last Sold Summary

      • 68 Days On Market

      Last Listing Agent Dave Spence RE/MAX Roots

  • /28

    $400,000

    $29K PRICE DROP
    • 4 Beds
    • 2 Baths
    • 1,432 Sq Ft

    115 E Monmouth St, Winchester, VA 22601

    Welcome to this 2 level house, the spacious patio backyard will be the perfect spot to relax and enjoy a relaxing day. Located near multiple stores and parks. Schedule your showing today!

    Mafe Zambrano Inmobiliaria De Las Casas LLC

    115 E Monmouth St, Winchester, VA 22601
  • /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
  • /47

    $349,990

    Sold Aug 17, 2026

    519 Fairmont Ave, Winchester, VA 22601

    • 3 Beds
    • 1 Bath
    • 2,102 Sq Ft
    • Built 1900

    Last Sold Summary

    • 10% Below List Price
    • $167/SF
    • 43 Days On Market

    Current Estimated Value $356,792

    Last Listing Agent Hannah Won Samson Properties

    519 Fairmont Ave, Winchester, VA 22601
    • /29

      Est $310,344

      Not Listed For Sale

      3141 Papermill Rd, Winchester, VA 22601

      • 3 Beds
      • 1 Bath
      • 1,183 Sq Ft
      • Built 1950
      3141 Papermill Rd, Winchester, VA 22601

      Last Sold Summary

      • 10 Days On Market

      Last Listing Agent Dalton Stem LPT Realty, LLC

  • /113

    $629,000

    • 4 Beds
    • 2.5 Baths
    • 2,810 Sq Ft

    507 S Stewart St, Winchester, VA 22601

    If you've been waiting for a home that offers both character and modern convenience, this one deserves a close look. This all-brick, charming Cape Cod is located on a beautiful tree-lined street in the heart of Winchester with more space & versatility than meets the eye. Cross the threshold into the large, welcoming foyer and let your gaze take it all in...Large living room, large dining room,

    Angela Duncan MarketPlace REALTY

    507 S Stewart St, Winchester, VA 22601
  • /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
  • /48

    $574,900

    Sold Oct 17, 2025

    1629 Pondview Dr, Winchester, VA 22601

    • 4 Beds
    • 3.5 Baths
    • 2,602 Sq Ft
    • Built 1995

    Last Sold Summary

    • $221/SF
    • 83 Days On Market

    Current Estimated Value $597,858

    Last Listing Agent Kerry & Ed Stinson Berkshire Hathaway HomeServices PenFed Realty

    1629 Pondview Dr, Winchester, VA 22601
    • /20

      Est $308,242

      Not Listed For Sale

      3113 Papermill Rd, Winchester, VA 22601

      • 3 Beds
      • 1 Bath
      • 895 Sq Ft
      • Built 1956
      3113 Papermill Rd, Winchester, VA 22601

      Last Sold Summary

      • 11 Days On Market

      Last Listing Agent Marcy Cantatore Corcoran McEnearney

  • /10

    $399,000

    • Land
    • 3,920 Sq Ft
    • $4,433,333 per Acre

    1 N Braddock St, Winchester, VA 22601

    Make Offer! Excellent Development Opportunity! Downtown Winchester, VA! APPROVED (!) Mixed Use site plan for multi-story building consisting of 1st floor commercial space (1,340 SF) with 6x spacious luxury condos/apartments (potential for seven) with rooftop patio above (for total of 8 rental units)! Legacy development opportunity! One North is located in the second historical district and

    Gillian Greenfield Coldwell Banker Premier

    1 N Braddock St, Winchester, VA 22601
  • /2

    $1,425 Per Month

    • 2 Beds
    • 1 Bath
    • 1,036 Sq Ft
    • House for Rent

    131 S Purcell Ave, Winchester, VA 22601

    This charming Colonial-style home, built in 1920, offers 2 spacious bedrooms and 1 full bathroom, this detached residence is perfect for those seeking a cozy yet functional living space. The property features durable vinyl siding, ensuring low maintenance while maintaining its classic appeal. On-street parking available. Conveniently located near a variety of local amenities. Residents can enjoy

    Rebecca Sims Century 21 Redwood Realty

    131 S Purcell Ave, Winchester, VA 22601
  • /87

    $578,000

    Sold Nov 18, 2025

    107 Roszel Rd, Winchester, VA 22601

    • 4 Beds
    • 2.5 Baths
    • 3,232 Sq Ft
    • Built 1960

    Last Sold Summary

    • $179/SF
    • 59 Days On Market

    Current Estimated Value $607,659

    Last Listing Agent John Scully Colony Realty

    107 Roszel Rd, Winchester, VA 22601
    • /37

      Est $338,927

      Not Listed For Sale

      2905 First St, Winchester, VA 22601

      • 3 Beds
      • 2 Baths
      • 1,584 Sq Ft
      • Built 1968
      2905 First St, Winchester, VA 22601

      Last Sold Summary

      • 11 Days On Market

      Last Listing Agent Melissa Johnston ERA Oakcrest Realty, Inc.

Showing Results 161 - 200, Page 5 of 18

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