12,855

Winchester County, VA Homes

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  • /45

    $315,000

    $35K PRICE DROP
    • 3 Beds
    • 2.5 Baths
    • 1,728 Sq Ft

    913 Orchard Hill Dr, Winchester, VA 22601

    New roof, new windows, all brick exterior, wood burning fireplace, screened porch. Perfect opportunity for buyers to bring the interior of the property to neighborhood standards and enhance the value through sweat equity. This home has a great floor plan and an enviable location in beautifully maintained, established area. Located with easy access to amenities, shopping and commuter

    Dallas Croft Samson Properties

    913 Orchard Hill Dr, Winchester, VA 22601
  • /2

    $1,695

    Total Monthly Price

    • 3 Beds
    • 1 Bath
    • 1,300 Sq Ft
    • Townhouse for Rent

    668 Virginia Ave, Winchester, VA 22601

    Pictures coming soon, *photo of similar unit* Beautiful 3 Bedroom 1 Bath townhouse in the perfect LOCATION!!! So close to rt7, and I81 and still within walking distance to all the small town charm Winchester is known for. This townhouse has beautiful hardwood floors throughout, large rooms, a full unfinished basement with washer and dryer hook ups and so much more. It is an end unit and has

    668 Virginia Ave, 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 $315,217

    Last Listing Agent Anna Fox NextHome Realty Select

    2923 S Pleasant Valley Rd, Winchester, VA 22601
    • /46

      Est $529,592

      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

  • /2

    $199,900

    • Land
    • 6,969 Sq Ft
    • $1,249,375 per Acre

    1415 Ramseur Ln, Winchester, VA 22601

    Steve DuBrueler Coldwell Banker Premier

    1415 Ramseur Ln, Winchester, VA 22601
  • /42

    $2,250 Per Month

    • 3 Beds
    • 1.5 Baths
    • 1,456 Sq Ft
    • House for Rent

    6 W Cecil St, Winchester, VA 22601

    Located just off the south end of the Old Town mall minutes from the shops and restaurants. Lovely three bedroom unit with full bath on the second floor and half bath on the main floor. Fully renovated in 2019 with all new systems and appliances under historic tax credit standards. Beautifully refinished wood floors. Full width sun room on the rear second floor. Exclusive access to attic for

    Richard Bell Adams-Nelson & Associates Inc

    6 W Cecil St, 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 $299,319

    Last Listing Agent Susan Caulfield Pearson Smith Realty, LLC

    501 Battle Ave, Winchester, VA 22601
    • /38

      Est $531,892

      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

    $240,000

    Under Contract
    • 2 Beds
    • 1 Bath
    • 757 Sq Ft

    17 Glaize Ave, Winchester, VA 22601

    Welcome to this charming Winchester home, coming soon!This adorable 2-bedroom, 1-bath property offers 757 square feet of cozy living space and plenty of character. Enjoy the inviting front porch, spacious yard, and convenient location. Whether you’re a first-time buyer, downsizing, or looking for an investment opportunity, this home is worth a look. More details and professional photos coming

    Tina Purcell Pearson Smith Realty, LLC

    17 Glaize Ave, Winchester, VA 22601
  • /8

    $1,250 Per Month

    • 1 Bed
    • 1 Bath
    • 2,058 Sq Ft
    • Condo for Rent

    36 S Cameron St Unit 2, Winchester, VA 22601

    Charming 1-bedroom, 1-bath apartment located in the heart of historic downtown Winchester! This inviting home features a bright living room with beautiful built-in shelving and passthrough openings to the kitchen, creating an open and connected feel. The updated kitchen includes stainless steel appliances, a stylish tiled backsplash, granite countertops, and crisp white cabinetry. Enjoy the

    James King RE/MAX Roots

    36 S Cameron St Unit 2, 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 $326,330

    Last Listing Agent Jim Stafford ERA Oakcrest Realty, Inc.

    2225 Harrison St, Winchester, VA 22601
    • /59

      Est $561,988

      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

    $625,000

    Coming Soon Oct 2
    • Studio
    • 4,146 Sq Ft

    25 W Boscawen St, Winchester, VA 22601

    Awesome income-producing multi-unit property in the heart of downtown Winchester. This stately red brick building delivers immediate cash flow with a great documented CAP rate and all three units currently occupied with tenants paying all utilities. High ceilings and abundant natural light create desirable living spaces. Located just a half-block from the Winchester walking mall, residents enjoy

    Teri Domanski Your Home Sold Guaranteed Realty - East LLC

    25 W Boscawen St, Winchester, VA 22601
  • /7

    $1,500 Per Month

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

    115 S Loudoun St, Winchester, VA 22601

    Charming 1 bedroom 1 bath apartment downtown Winchester. Cozy 2nd floor apartment is freshly painted and offers a prime spot with views overlooking the Walking mail, just steps away from shopping, dining and entertainment.

    Meridee Powars Link Realty Services LLC

    115 S Loudoun St, Winchester, VA 22601
  • /52

    $360,000

    Sold Aug 17, 2026

    824 Appleseed Ct, Winchester, VA 22601

    • 3 Beds
    • 3 Baths
    • 2,052 Sq Ft
    • Built 1981

    Last Sold Summary

    • 1% Below List Price
    • $175/SF
    • 16 Days On Market

    Current Estimated Value $364,390

    Last Listing Agent Laura White ERA Oakcrest Realty, Inc.

    824 Appleseed Ct, Winchester, VA 22601
    • /37

      Est $459,311

      Not Listed For Sale

      2824 Broadview St, Winchester, VA 22601

      • 3 Beds
      • 2 Baths
      • Built 2024
      2824 Broadview St, Winchester, VA 22601

      Last Sold Summary

      • 68 Days On Market

      Last Listing Agent Elizabeth Flood Keller Williams Realty

  • /17

    $289,000

    $6K PRICE DROP
    • 3 Beds
    • 1 Bath
    • 960 Sq Ft

    1314 S Braddock St, Winchester, VA 22601

    1314 S Braddock St is a one-story Winchester single-family home with a functional single-level layout. The kitchen is equipped with stainless steel appliances for everyday cooking and cleanup. The bathroom includes a tub and shower for daily use, and a dedicated laundry area with a stacked washer and dryer keeps utility tasks out of the main living space. Multiple bedrooms provide flexible room

    Jacqueline Moore Open Door Brokerage, LLC

    1314 S Braddock St, Winchester, VA 22601
  • /23

    $1,800 Per Month

    • 2 Beds
    • 2 Baths
    • 1,650 Sq Ft
    • Townhouse for Rent

    445 Royal St, Winchester, VA 22601

    This charming duplex in the WEA-VILLA community offers a delightful garden view, perfect for enjoying peaceful mornings or relaxing evenings. Built in 1965, this well-maintained ranch-style home features 2 spacious bedrooms and 2 full bathrooms, providing ample space for comfort. The fully finished basement adds versatility, ideal for a cozy retreat or extra storage. With a generous lot size of

    Dave Spence RE/MAX Roots

    445 Royal St, 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 $736,969

    Last Listing Agent Dave Spence RE/MAX Roots

    2530 Goldenfield Ln, Winchester, VA 22601
    • /33

      Est $420,915

      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

  • /77

    $999,000

    Pending
    • 4 Beds
    • 2.5 Baths
    • 4,246 Sq Ft

    517 Merrimans Ln, Winchester, VA 22601

    John Schroth Colony Realty

    517 Merrimans Ln, 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
  • /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
    • /35

      Est $378,645

      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

  • /2

    $225,000

    Pending
    • 3 Beds
    • 1 Bath
    • 925 Sq Ft

    411 Shenandoah Place, Winchester, VA 22601

    Exceptional investor opportunity! This solid 3 bed 1 bath home tucked into the desirable Winchester city limits is ready for you! An easy addition to any portfolio, so bring your vision, this is your diamond in the rough!

    Lisa Behr Hunt Country Sotheby's International Realty

    411 Shenandoah Place, Winchester, VA 22601
  • /14

    $1,250 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
  • /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 $442,722

    Last Listing Agent Shannon Jones Pearson Smith Realty, LLC

    413 George St, Winchester, VA 22601
    • /20

      Est $411,003

      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

  • /52

    $369,990

    New Construction
    • 3 Beds
    • 3.5 Baths
    • 1,756 Sq Ft

    229 Monteith Dr, Winchester, VA 22601

    The most affordable townhomes in Winchester City! Luxury 3-level, 3-bedroom townhome with 1-car garage located in the heart of Winchester! Possibility of 4th bedroom or flex space in the finished lower level with private full bath and walk-in shower; ideal for guests, home office, or recreation room. ***OFFERING UP TO $5K IN CLOSING COST ASSISTANCE FOR PRIMARY RESIDENCE WITH USE OF APPROVED

    Brittany Newman DRB Group Realty, LLC

    229 Monteith Dr, Winchester, VA 22601
  • /43

    $2,495 Per Month

    • 4 Beds
    • 3.5 Baths
    • 1,889 Sq Ft
    • Townhouse for Rent

    656 Arden Ct, Winchester, VA 22601

    656 Arden Ct is an attractive new 3 level townhome with full brick front in Winchester, VA. Ready to move-in LEASE! Our modern Adams floorplan features a 1-car garage, and a bedroom and full bathroom on the first floor. Main level with LVP Floors. The kitchen is equipped with beautiful quartz countertops, white cabinets, and stainless-steel appliances. The upper floor offers 3 bedrooms including

    Swaminathan Nithiyanandham Maram Realty, LLC

    656 Arden Ct, Winchester, VA 22601
  • /42

    $285,000

    Sold Aug 13, 2026

    102 N Purcell Ave, Winchester, VA 22601

    • 2 Beds
    • 1 Bath
    • 1,458 Sq Ft
    • Built 1948

    Last Sold Summary

    • 2% Below List Price
    • $195/SF
    • 0 Days On Market

    Current Estimated Value $289,113

    Last Listing Agent Bradley Comstock ERA Oakcrest Realty, Inc.

    102 N Purcell Ave, Winchester, VA 22601
    • /80

      Est $435,480

      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

  • /23

    $127,750

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

    0 Wolf Spring Trail Unit VAFV2043748, 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 and

    Chad Pangle Whitetail Properties Real Estate, LLC

    0 Wolf Spring Trail Unit VAFV2043748, Winchester, VA 22602
  • /23

    $2,500 Per Month

    • 2 Beds
    • 2 Baths
    • 1,123 Sq Ft
    • Condo for Rent

    210 E Boscawen St Unit 201, Winchester, VA 22601

    This two bedroom and two bath apartment overlooks Vibrissa's beautiful courtyard and mural. Easy to clean and maintain LVP flooring has been installed throughout. The kitchen features an island, tons of cabinet space, plenty of drawers for organizing, and stainless appliances. The living area is complete with a 77" 4K Smart TV. The building has closed circuit video security with easy app access

    Katie Landi Jordan Samson Properties

    210 E Boscawen St Unit 201, 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 $462,579

    Last Listing Agent Tiffany Hunter ERA Oakcrest Realty, Inc.

    609 Crystal Ct, Winchester, VA 22601
    • /71

      Est $967,794

      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

  • /29

    $299,500

    • 3 Beds
    • 1.5 Baths
    • 1,138 Sq Ft

    621 Watson Ave, Winchester, VA 22601

    Fresh, stylish, and move-in ready! Welcome to 621 Watson Avenue, a beautifully refreshed 3-bedroom, 1.5-bath duplex offering a wonderful blend of classic character and modern updates. Step inside to find freshly painted walls and beautiful hardwood floors that create a bright, inviting atmosphere throughout the main living areas.The updated kitchen features new cabinetry and stainless steel

    Caleb Fowler Samson Properties

    621 Watson Ave, Winchester, VA 22601
  • /9

    $1,690 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 $643,533

    Last Listing Agent Jeanne Mezzatesta Colony Realty

    501 Jefferson St, Winchester, VA 22601
    • /49

      Est $540,115

      Not Listed For Sale

      2853 Packer St, Winchester, VA 22601

      • 5 Beds
      • 3.5 Baths
      • 3,284 Sq Ft
      • Built 2007
      2853 Packer St, Winchester, VA 22601

      Last Sold Summary

      • 209 Days On Market

      Last Listing Agent Robert Adams Weichert Realtors - Blue Ribbon

Showing Results 241 - 280, Page 7 of 18

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