12,855

Winchester County, VA Homes

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  • /46

    $325,000

    • 4 Beds
    • 2 Baths
    • 1,592 Sq Ft

    805 S Kent St, Winchester, VA 22601

    Welcome home! This beautifully maintained two-level home offers 4 bedrooms and 2 full bathrooms in the heart of Winchester. Warm and inviting, the home features a comfortable, functional layout with classic charm and thoughtful updates throughout. Pride of ownership is evident in every detail, both inside and out. Enjoy spacious living areas, a fully fenced yard perfect for relaxing or

    Carolina Mosquera Weichert, REALTORS

    805 S Kent St, Winchester, VA 22601
  • /17

    $2,100

    Total Monthly Price

    • 3 Beds
    • 2.5 Baths
    • House for Rent

    2051 Stoneleigh Dr, Winchester, VA 22601

    3 bed, 2.5 bath Duplex with Excellent in town location! , Garage, Fenced-In yard, Rear deck, Gas heat/hot water heater, Central A/C, Kitchen w/stove, refrigerator, and dishwasher, Washer & Dryer hookup, Ceiling fans though out. City Water/Sewer. Only one neighbor, great views off back porch, very close to shopping, fuel, and several city amenities Washer/Dryer are not warranted if located in

    2051 Stoneleigh Dr, Winchester, VA 22601
  • /57

    $648,900

    Sold Jun 12, 2026

    930 Wayne Dr, Winchester, VA 22601

    • 4 Beds
    • 3.5 Baths
    • 4,188 Sq Ft
    • Built 2003

    Last Sold Summary

    • 1% Above List Price
    • $155/SF
    • 24 Days On Market

    Current Estimated Value $643,283

    Last Listing Agent Elizabeth Flood Keller Williams Realty

    930 Wayne Dr, Winchester, VA 22601
    • /15

      Not Listed For Sale

      3138 Eton Place, Winchester, VA 22601

      • 3 Beds
      • 2.5 Baths
      • 1,916 Sq Ft
      • Built 2024
      3138 Eton Place, Winchester, VA 22601

      Last Sold Summary

      • 220 Days On Market

      Last Listing Agent Brittany Newman DRB Group Realty, LLC

  • /9

    $308,000

    • 2 Beds
    • 2 Baths
    • 800 Sq Ft

    2519 Hockman Ave, Winchester, VA 22601

    This charming cottage in the heart of the City of Winchester is poised for a remarkable transformation with major renovations slated for 2026. Built in 1950, this detached home offers a unique opportunity for investors seeking to capitalize on a revitalized property in a desirable location. With two spacious bedrooms and two full bathrooms, the layout is perfect for modern living. The full

    Meridee Powars Link Realty Services LLC

    2519 Hockman Ave, Winchester, VA 22601
  • /23

    $2,500 Per Month

    • 2 Beds
    • 2 Baths
    • 1,150 Sq Ft
    • Condo for Rent

    210 E Boscawen St Unit 200, Winchester, VA 22601

    This two bedroom and two bath apartment has lots of natural light with windows spanning two sides of the building (window treatments already installed). The convenient location is just two blocks from the old town walking mall! Easy to clean and maintain LVP flooring has been installed throughout. The kitchen features ample cabinet space with plenty of drawers for easy organizing, and stainless

    Katie Landi Jordan Samson Properties

    210 E Boscawen St Unit 200, Winchester, VA 22601
  • /2

    $585,000

    Sold May 04, 2026

    328 Sheridan Ave, Winchester, VA 22601

    • 4 Beds
    • 2.5 Baths
    • 2,909 Sq Ft
    • Built 1958

    Last Sold Summary

    • $201/SF
    • 3 Days On Market

    Current Estimated Value $568,368

    Last Listing Agent Mary Casselano Dream Real Estate

    328 Sheridan Ave, Winchester, VA 22601
    • /63

      Not Listed For Sale

      327 Russellcroft Rd, Winchester, VA 22601

      • 3 Beds
      • 3 Baths
      • 3,873 Sq Ft
      • Built 1968
      327 Russellcroft Rd, Winchester, VA 22601

      Last Sold Summary

      • 5 Days On Market

      Last Listing Agent Matt Kilmer Samson Properties

  • /44

    $319,900

    • 3 Beds
    • 1 Bath
    • 1,050 Sq Ft

    12 N Purcell Ave, Winchester, VA 22601

    Welcome to 12 N Purcell Ave, a classic white bungalow offering standout curb appeal, a well-kept lawn and landscaping, and an unbeatable central location. Relax on the covered front porch before stepping inside to a bright and inviting main level featuring rich hardwood floors and a spacious eat-in kitchen with plentiful cabinet space. Two sizable bedrooms and a full bath round out the main floor

    Dan Whitacre Colony Realty

    12 N Purcell Ave, Winchester, VA 22601
  • /8

    $1,495

    Total Monthly Price

    • 3 Beds
    • 1.5 Baths
    • 1,144 Sq Ft
    • Townhouse for Rent

    1110 Allen Dr, Winchester, VA 22601

    Lovely 3 Bedroom 1.5 Bath, recently updated with new carpet, vinyl and finished hardwood floors on the upper level. Great commuter location! This one won't last long so get your application in now. Gas heat Washer and dryer hook ups Pet friendly (up to 40lbs) with additional fee of $400 per pet

    1110 Allen Dr, Winchester, VA 22601
  • /28

    $580,000

    Sold Oct 24, 2025

    230 W Boscawen St, Winchester, VA 22601

    • 7,650 Sq Ft
    • Built 1891

    Last Sold Summary

    • $76/SF
    • 284 Days On Market

    Current Estimated Value $597,445

    Last Listing Agent Gillian Greenfield Coldwell Banker Premier

    230 W Boscawen St, Winchester, VA 22601
    • /15

      Not Listed For Sale

      3136 Eton Place, Winchester, VA 22601

      • 3 Beds
      • 2.5 Baths
      • 1,918 Sq Ft
      • Built 2024
      3136 Eton Place, Winchester, VA 22601

      Last Sold Summary

      • 148 Days On Market

      Last Listing Agent Brittany Newman DRB Group Realty, LLC

  • /63

    $699,000

    • 7 Beds
    • 5 Baths
    • 4,736 Sq Ft

    2700 Loyalty Ct, Winchester, VA 22601

    Welcome to 2700 Loyalty Court—a beautifully maintained showcase home offering nearly 5,000 square feet of unmatched versatility in one of Winchester City’s most coveted locations. Commanding a prime corner lot on a peaceful cul-de-sac, this residence immediately captivates with its timeless stone-and-vinyl exterior, inviting covered front porch, and unmistakable curb appeal. Step inside to a

    Dan Whitacre Colony Realty

    2700 Loyalty Ct, Winchester, VA 22601
  • /13

    $1,900 Per Month

    • 800 Sq Ft
    • Condo for Rent

    2971 Valley Ave, Winchester, VA 22601

    Fully furnished loft style apartments. Lower level consists of living room, dining room, kitchen and bath. The bedroom is on the second level. These are full furnished units that allow pets. Perfect all inclusive rental. Owners pays for everything to include cable and internet. These units can be rented weekly also

    Meridee Powars Link Realty Services LLC

    2971 Valley Ave, Winchester, VA 22601
  • /30

    $325,000

    Sold Oct 20, 2025

    966 Woodstock Ln, Winchester, VA 22601

    • 3 Beds
    • 2 Baths
    • 1,529 Sq Ft
    • Built 1980

    Last Sold Summary

    • $213/SF
    • 31 Days On Market

    Current Estimated Value $335,017

    Last Listing Agent Anselm Tamasang Weichert Realtors - Blue Ribbon

    966 Woodstock Ln, Winchester, VA 22601
    • /15

      Not Listed For Sale

      3142 Eton Place, Winchester, VA 22601

      • 3 Beds
      • 2.5 Baths
      • 1,916 Sq Ft
      • Built 2024
      3142 Eton Place, Winchester, VA 22601

      Last Sold Summary

      • 141 Days On Market

      Last Listing Agent Brittany Newman DRB Group Realty, LLC

  • /52

    $369,000

    $56K PRICE DROP Under Contract
    • 2 Beds
    • 2 Baths
    • 1,799 Sq Ft

    437 Beechcroft Rd, Winchester, VA 22601

    PRICE REDUCED! BRICK BEAUTY ON A CORNER LOT WITH AN ATTACHED CARPORT AND A FULL BASEMENT. This remodeled and freshly painted 2-bedroom, 2-bath rancher with newly refinished hardwood floors is move-in ready. In-town convenience with nearby shopping, restaurants and services. A short drive to commuter routes 81, 37 and 50, downtown and Winchester Medical Center. Perfect for those who are downsizing

    Teresa Strohmeyer ERA Oakcrest Realty, Inc.

    437 Beechcroft Rd, Winchester, VA 22601
  • /32

    $1,495

    Total Monthly Price

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

    2549 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

    2549 Bradford Ct, Winchester, VA 22601
  • /36

    $635,500

    Sold Nov 19, 2025

    315 W Leicester St, Winchester, VA 22601

    • 4 Beds
    • 4 Baths
    • 3,100 Sq Ft
    • Built 1923

    Last Sold Summary

    • $205/SF
    • 5 Days On Market

    Current Estimated Value $651,955

    Last Listing Agent Leigh Phillips MarketPlace REALTY

    315 W Leicester St, Winchester, VA 22601
    • /22

      Not Listed For Sale

      3146 Eton Place, Winchester, VA 22601

      • 3 Beds
      • 2.5 Baths
      • 1,928 Sq Ft
      • Built 2024
      3146 Eton Place, Winchester, VA 22601

      Last Sold Summary

      • 51 Days On Market

      Last Listing Agent Brittany Newman DRB Group Realty, LLC

  • /30

    $409,000

    • 4 Beds
    • 1 Bath
    • 1,768 Sq Ft

    322 E Piccadilly St, Winchester, VA 22601

    Welcome to a Mid‑Century Modern Home Where Timeless Character Meets Modern Sophistication. This beautifully updated 3–4 bedroom mid‑century modern home, where timeless character meets modern sophistication in one of Winchester’s most convenient and walkable locations. The large covered front porch immediately sets the tone—an inviting space for morning coffee or relaxed evening

    LESLIE WEBB Long & Foster Real Estate, Inc.

    322 E Piccadilly St, Winchester, VA 22601
  • /12

    $2,400 Per Month

    • 3 Beds
    • 3 Baths
    • 2,050 Sq Ft
    • Townhouse for Rent

    3144 Eton Place, Winchester, VA 22601

    Welcome to this beautiful unit , light filled, 2 car garage Town home in the center of the Lofts at creekside Shopping center.As you enter, featuring stylish LVP flooring Foyer , with a recreation room that can be used as media room , office room, Play roomThe second floor is open floor model featuring Kitchen, Family, Dining and a deckThird floor featuing 3 comfortable

    sreerekha challapalli Alluri Realty, Inc.

    3144 Eton Place, Winchester, VA 22601
  • /116

    $537,500

    Sold Jan 08, 2026

    510 S Washington St, Winchester, VA 22601

    • 3 Beds
    • 1.5 Baths
    • 2,874 Sq Ft
    • Built 1920

    Last Sold Summary

    • $187/SF
    • 14 Days On Market

    Current Estimated Value $596,283

    Last Listing Agent Laurie Webber Century 21 Modern Realty Results

    510 S Washington St, Winchester, VA 22601
    • /22

      Not Listed For Sale

      3132 Eton Place, Winchester, VA 22601

      • 3 Beds
      • 2.5 Baths
      • 2,074 Sq Ft
      • Built 2024
      3132 Eton Place, Winchester, VA 22601

      Last Sold Summary

      • 21 Days On Market

      Last Listing Agent Brittany Newman DRB Group Realty, LLC

  • /26

    $364,990

    New Construction $3K PRICE DROP
    • 3 Beds
    • 3.5 Baths
    • 1,756 Sq Ft

    11 Monteith Dr, Winchester, VA 22601

    3 Level Townhome with Lower Level Bathroom! This beautifully upgraded home features an open-concept layout with spacious living areas and a stunning kitchen complete with oversized island seating for four; perfect for entertaining and everyday living. The third level offers conveniently located laundry near the bedrooms for added convenience. Enjoy outdoor living on the 10x16 maintenance-free

    DRB Homes Builder
    11 Monteith Dr, Winchester, VA 22601
  • /8

    $1,395

    Total Monthly Price

    • 2 Beds
    • 1 Bath
    • 1,115 Sq Ft
    • Townhouse for Rent

    305 S Kent St, Winchester, VA 22601

    Pictures coming soon Great historic duplex with 2 bedrooms 1 bath, large rooms, a bonus room, warm gas heat, partial unfinished basement and a deck with a small yard all in the heart of downtown Winchester. Walk to take in all the rich history Winchester has to offer, The Handley Library, museums, the walking mall and all the great shops, cafes, pubs. Gas heat, water split with 307

    305 S Kent St, Winchester, VA 22601
  • /47

    $295,000

    Sold Nov 03, 2025

    2964 Grace St, Winchester, VA 22601

    • 2 Beds
    • 1 Bath
    • 780 Sq Ft
    • Built 1955

    Last Sold Summary

    • $378/SF
    • 22 Days On Market

    Current Estimated Value $299,529

    Last Listing Agent Jane Norton United Real Estate Premier

    2964 Grace St, Winchester, VA 22601
    • /41

      Est $498,808

      Not Listed For Sale

      2060 Taylor Grace Ct, Winchester, VA 22601

      • 4 Beds
      • 2.5 Baths
      • 1,776 Sq Ft
      • Built 2011
      2060 Taylor Grace Ct, Winchester, VA 22601

      Last Sold Summary

      • 22 Days On Market

      Last Listing Agent Paul Gallagher Colony Realty

  • /7

    $1,100,000

    Under Contract
    • Land
    • 2.3 Acres
    • $478,261 per Acre

    0 S Pleasant Valley Rd Unit VAFV2039602, Winchester, VA 22601

    2.3 Acre Outparcel on Pleasant Valley Road for Sale Neighbors include Walmart, Ross, Target, Panera Bread, Olive Garden, Petco, and the list goes on! Zoned CM1, ideal for auto sales, offices, retail, and flex development. All utilities to site. Outstanding proximity to massive commercial and multifamily growth. VA's fastest growing City in it's fastest growing commercial district. Almost 500'

    Gillian Greenfield Coldwell Banker Premier

    0 S Pleasant Valley Rd Unit VAFV2039602, Winchester, VA 22601
  • /15

    $1,250 Per Month

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

    204 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 updated eat-in kitchen has durable vinyl flooring. Exceptional closet space throughout the home provides

    Meghan Pachas MAP Property Solutions, LLC.

    204 E Whitlock Ave, Winchester, VA 22601
  • /45

    $500,000

    Sold Oct 15, 2025

    436 W Leicester St, Winchester, VA 22601

    • 3 Beds
    • 1.5 Baths
    • 1,592 Sq Ft
    • Built 1925

    Last Sold Summary

    • $314/SF

    Current Estimated Value $504,290

    Last Listing Agent Jeanne Mezzatesta Colony Realty

    436 W Leicester St, Winchester, VA 22601
    • /43

      Est $560,973

      Not Listed For Sale

      2044 Taylor Grace Ct, Winchester, VA 22601

      • 4 Beds
      • 3.5 Baths
      • 3,568 Sq Ft
      • Built 2011
      2044 Taylor Grace Ct, Winchester, VA 22601

      Last Sold Summary

      • 10 Days On Market

      Last Listing Agent Cynthia Lee RE/MAX Roots

  • /33

    $300,000

    $20K PRICE DROP
    • 3 Beds
    • 3 Baths
    • 1,281 Sq Ft

    115 S Purcell Ave, Winchester, VA 22601

    Price Improvement!!! Don't miss this 3-bedroom, 3 full-bath bungalow in a prime location! Just minutes from vibrant downtown shopping and dining, and a short walk to Jim Barnett Park. The park includes a dog park, swimming pool, and pickleball courts. This home offers the ideal combination of convenience, charm, and access to outdoor amenities. New roof installed in 2018.

    Matthew Berry MarketPlace REALTY

    115 S Purcell Ave, Winchester, VA 22601
  • /33

    $1,995

    Total Monthly Price

    • 2 Beds
    • 2 Baths
    • 1,120 Sq Ft
    • Townhouse for Rent

    2249 Papermill Rd, Winchester, VA 22601

    Available for Rent: 2-Level Townhome at 2249 Papermill Rd Discover comfort and everyday convenience in this fantastic 2-bedroom, 2-full-bath rental townhome in Winchester, VA. Main Level: Open & Inviting Enjoy a bright, open floor plan designed for easy living. The spacious living room flows directly into the kitchen and dining area, creating a welcoming space to relax or entertain guests. Upper

    2249 Papermill Rd, Winchester, VA 22601
  • /35

    $270,000

    Sold Mar 03, 2026

    239 Chestnut St, Winchester, VA 22601

    • 2 Beds
    • 1 Bath
    • 1,176 Sq Ft
    • Built 1976

    Last Sold Summary

    • $230/SF
    • 100 Days On Market

    Current Estimated Value $278,776

    Last Listing Agent William Wertz Wildhawks Realty LLC

    239 Chestnut St, Winchester, VA 22601
    • /19

      Est $310,277

      Not Listed For Sale

      521 1/2 N Loudoun St, Winchester, VA 22601

      • 4 Beds
      • 1.5 Baths
      • 1,277 Sq Ft
      • Built 1936
      521 1/2 N Loudoun St, Winchester, VA 22601

      Last Sold Summary

      • 6 Days On Market

      Last Listing Agent Barton Chasler Realty ONE Group Old Towne

  • /46

    $499,999

    • 4 Beds
    • 3.5 Baths
    • 2,524 Sq Ft

    2643 Middle Rd, Winchester, VA 22601

    Location, Location, Location! NO HOA!!! Priced below assessed value! Hardwood floors on the main level. Formal living and dining room leads to the Family room with stone fireplace, breakfast nook and kitchen. Step out on to the deck to enjoy the views. Large fenced level backyard. Large Primary suite with sitting room and luxury bath. Good sized bedrooms, one with an attached bath. Lower level

    Lorraine Arora Berkshire Hathaway HomeServices PenFed Realty

    2643 Middle Rd, Winchester, VA 22601
  • /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
  • /36

    $525,000

    Sold Nov 14, 2025

    2723 Windwood Dr, Winchester, VA 22601

    • 3 Beds
    • 3 Baths
    • 2,726 Sq Ft
    • Built 1999

    Last Sold Summary

    • $193/SF
    • 38 Days On Market

    Current Estimated Value $540,673

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

    2723 Windwood Dr, Winchester, VA 22601
    • /24

      Est $369,535

      Not Listed For Sale

      456 Imperial St, Winchester, VA 22601

      • 3 Beds
      • 2 Baths
      • 1,722 Sq Ft
      • Built 1962
      456 Imperial St, Winchester, VA 22601

      Last Sold Summary

      • 76 Days On Market

      Last Listing Agent Holly Porter NewTown Realty

Showing Results 121 - 160, Page 4 of 18

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