12,854

Winchester County, VA Homes

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  • /26

    $429,000

    Open Sat 11AM - 1PM
    • 4 Beds
    • 2 Baths
    • 1,844 Sq Ft

    1310 Whittier Ave, Winchester, VA 22601

    Turn-key and move-in ready! This beautifully updated 4-bedroom, 2-bath home features a modern kitchen with recently updated appliances, a new HVAC system, and a new hot water heater for added peace of mind. Enjoy the spacious backyard, perfect for outdoor entertaining, along with convenient off-street parking and the freedom of no HOA. Nestled in an established neighborhood with large yards and a

    Sarah Hott Realty ONE Group Old Towne

    1310 Whittier Ave, 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 2

    305 S Kent St, Winchester, VA 22601
  • /55

    $675,000

    Sold Feb 12, 2026

    800 Lake Dr, Winchester, VA 22601

    • 5 Beds
    • 4 Baths
    • 4,576 Sq Ft
    • Built 2010

    Last Sold Summary

    • $148/SF
    • 87 Days On Market

    Current Estimated Value $706,827

    Last Listing Agent Lisa Behr Hunt Country Sotheby's International Realty

    800 Lake Dr, Winchester, VA 22601
    • /6

      Est $294,534

      Not Listed For Sale

      3037 Papermill Rd, Winchester, VA 22601

      • 3 Beds
      • 1 Bath
      • 1,008 Sq Ft
      • Built 1960
      3037 Papermill Rd, Winchester, VA 22601

      Last Sold Summary

      • 21 Days On Market

      Last Listing Agent Brett Sowder RE/MAX Roots

  • /64

    $375,000

    Coming Soon
    • 3 Beds
    • 1 Bath
    • 1,474 Sq Ft

    805 Pennsylvania Ave, Winchester, VA 22601

    Lovingly maintained, this charming brick rancher is the perfect starter home or investment opportunity! The main level offers three comfortable bedrooms, one full bath, a bright eat-in kitchen, and a spacious living room filled with natural light. The full unfinished basement provides endless potential for additional finished living space, while an existing hobby room is already in place—perfect

    Sherry Santmyer Hunt Country Sotheby's International Realty

    805 Pennsylvania Ave, Winchester, VA 22601
  • /20

    $2,000 Per Month

    • 3 Beds
    • 2.5 Baths
    • 1,896 Sq Ft
    • Townhouse for Rent

    921 Orchard Hill Dr, Winchester, VA 22601

    Great location, newly renovated. Big home boating 3 be3drroms ( none small !!), 2baths and laundry upstairs.Freshly painted with large sun room addition downstairs. Outbuilding for storage. Repairs may be completed sooner than 7/31. Property will go on the market immediately after repairs are completed. Don't miss chance on this great home.

    Jeff Webber Long & Foster Real Estate, Inc.

    921 Orchard Hill Dr, Winchester, VA 22601
  • /53

    $435,000

    Sold Jul 06, 2026

    25 W Southwerk St, Winchester, VA 22601

    • 3 Beds
    • 2.5 Baths
    • 1,904 Sq Ft
    • Built 1936

    Last Sold Summary

    • 3% Below List Price
    • $228/SF
    • 76 Days On Market

    Current Estimated Value $426,281

    Last Listing Agent Dan Whitacre Colony Realty

    25 W Southwerk St, Winchester, VA 22601
    • /24

      Est $337,716

      Not Listed For Sale

      2959 S Pleasant Valley Rd, Winchester, VA 22601

      • 3 Beds
      • 1.5 Baths
      • 1,199 Sq Ft
      • Built 1989
      2959 S Pleasant Valley Rd, Winchester, VA 22601

      Last Sold Summary

      • 5 Days On Market

      Last Listing Agent Anna Fox NextHome Realty Select

  • /45

    $334,900

    $15K 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
  • /17

    $2,400

    Total Monthly Price

    • 3 Beds
    • 2.5 Baths
    • House for Rent

    2066 Honeysuckle Ln, Winchester, VA 22601

    Immaculate home now available for rent in sought after ORCHARD HILL SUBDIVISION! 3 spacious bedrooms, ample storage space with several walk in closets, all appliances convey including washer/dryer. Sun room with cathedral ceilings and atrium doors to exit onto the rear brick patio, storage shed, small garden, and so much more! VAR or NVAR rental application with $50 per person application fee

    2066 Honeysuckle Ln, Winchester, VA 22601
  • /2

    $335,000

    Sold Jun 18, 2026

    120 Worsham Terrace, Winchester, VA 22602

    • 3 Beds
    • 4 Baths
    • 1,336 Sq Ft
    • Built 2011

    Last Sold Summary

    • $251/SF
    • 22 Days On Market

    Current Estimated Value $331,559

    Last Listing Agent Marielle Thoburn Keller Williams Realty

    120 Worsham Terrace, Winchester, VA 22602
    • /21

      Est $333,320

      Not Listed For Sale

      121 Summit Ave, Winchester, VA 22601

      • 3 Beds
      • 1.5 Baths
      • 1,020 Sq Ft
      • Built 1981
      121 Summit Ave, Winchester, VA 22601

      Last Sold Summary

      • 9 Days On Market

      Last Listing Agent Heloisa Amar Samson 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
  • /8

    $1,300 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
  • /87

    $650,000

    Sold Sep 16, 2025

    504 Old Fort Rd, Winchester, VA 22601

    • 5 Beds
    • 6 Baths
    • 3,824 Sq Ft
    • Built 2003

    Last Sold Summary

    • $170/SF
    • 74 Days On Market

    Current Estimated Value $709,421

    Last Listing Agent Dallas Croft Samson Properties

    504 Old Fort Rd, Winchester, VA 22601
    • /43

      Est $346,460

      Not Listed For Sale

      2924 Grace St, Winchester, VA 22601

      • 4 Beds
      • 2 Baths
      • 1,285 Sq Ft
      • Built 1975
      2924 Grace St, Winchester, VA 22601

      Last Sold Summary

      • 5 Days On Market

      Last Listing Agent Kristen Kerns Roberts Realty Group, LLC

  • /63

    $330,000

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

    805 S Kent St, Winchester, VA 22601

    Very well-maintained 2-level home offering 4 bedrooms and 2 full baths in the heart of Winchester. This home features a functional layout with a blend of classic charm and thoughtful updates throughout. Pride of ownership shows inside and out, with comfortable living spaces, a fully fenced yard, and a private driveway for off-street parking. Conveniently located near downtown, shopping, and

    Carolina Mosquera Weichert, REALTORS

    805 S Kent St, 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 SoonDon'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 level.

    332 Shawnee Ave, Winchester, VA 22601
  • /47

    $425,000

    Sold Mar 11, 2026

    431 Jefferson St, Winchester, VA 22601

    • 3 Beds
    • 1.5 Baths
    • 1,632 Sq Ft
    • Built 1956

    Last Sold Summary

    • 1% Above List Price
    • $260/SF
    • 4 Days On Market

    Current Estimated Value $436,408

    Last Listing Agent Dan Whitacre Colony Realty

    431 Jefferson St, Winchester, VA 22601
    • /25

      Est $381,259

      Not Listed For Sale

      2921 Second St, Winchester, VA 22601

      • 4 Beds
      • 3 Baths
      • 1,147 Sq Ft
      • Built 1955
      2921 Second St, Winchester, VA 22601

      Last Sold Summary

      • 39 Days On Market

      Last Listing Agent Joelle Graham Weichert, REALTORS

  • /17

    $295,000

    • 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
  • /19

    $1,500 Per Month

    • 2 Beds
    • 1.5 Baths
    • 1,106 Sq Ft
    • Townhouse for Rent

    544 Allston Cir, Winchester, VA 22601

    NO PETS. 2bedroom 1.5 bath townhouse located minutes to shops and dining in Winchester. Central heating and AC. Large primary bedroom. Unfinished walkout basement. Requirements: (1) Minium household annual income $67k, (2) Good Credit, (3) Good Landlord Reference. $47 application fee per applicant. Contact listing agent for application

    Courtney Spaid Crum Realty, Inc.

    544 Allston Cir, Winchester, VA 22601
  • /2

    $560,000

    Sold Jul 28, 2026

    813 Chelsea Dr, Winchester, VA 22601

    • 5 Beds
    • 3 Baths
    • 2,182 Sq Ft
    • Built 2003

    Last Sold Summary

    • 19% Below List Price
    • $257/SF
    • 76 Days On Market

    Current Estimated Value $603,841

    Last Listing Agent Teresa Strohmeyer ERA Oakcrest Realty, Inc.

    813 Chelsea Dr, Winchester, VA 22601
    • /22

      Est $299,277

      Not Listed For Sale

      313 Summit Ave, Winchester, VA 22601

      • 2 Beds
      • 1 Bath
      • 954 Sq Ft
      • Built 1951
      313 Summit Ave, Winchester, VA 22601

      Last Sold Summary

      • 25 Days On Market

      Last Listing Agent Susan Wathen 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
  • /23

    $2,350

    Total Monthly Price

    • 3 Beds
    • 2.5 Baths
    • 1,200 Sq Ft
    • August Only: 1st Month Free with Move-in by 8/30: Downtown Winchester Living – Fully Renovated 3-...

    213 N Kent St, Winchester, VA 22601

    Experience the best of downtown living in this beautifully remodeled upper-level apartment located at 213 N. Kent Street in the heart of Historic Downtown Winchester. Offering over 1,200 square feet of thoughtfully updated living space, this spacious home features 3 bedrooms, 3 bathrooms, and durable hard-surface flooring throughout.The modern kitchen features updated finishes and

    213 N Kent St, Winchester, VA 22601
  • /34

    $375,000

    Sold Feb 06, 2026

    318 E Piccadilly St, Winchester, VA 22601

    • 4 Beds
    • 1.5 Baths
    • 1,953 Sq Ft
    • Built 1929

    Last Sold Summary

    • 6% Below List Price
    • $192/SF
    • 40 Days On Market

    Current Estimated Value $390,798

    Last Listing Agent Dan Whitacre Colony Realty

    318 E Piccadilly St, Winchester, VA 22601
    • /19

      Est $336,540

      Not Listed For Sale

      2928 First St, Winchester, VA 22601

      • 3 Beds
      • 1.5 Baths
      • 1,472 Sq Ft
      • Built 1972
      2928 First St, Winchester, VA 22601

      Last Sold Summary

      • 11 Days On Market

      Last Listing Agent Kimberly Schroeder Long & Foster Real Estate, Inc.

  • /6

    $370,000

    • 2 Beds
    • 2 Baths
    • 1,200 Sq Ft

    1845 Rosser Ln, Winchester, VA 22601

    Beautifully maintained 2-bedroom, 2-bath Ranch home in the desirable Willow Lawn Cottages 55+Community. The main-level features an open floor plan, vaulted ceiling, ceiling fan, gas fireplace, largeconcrete patio, and 1-car garage. 2026 updates include a new HVAC system. The primary suite offers awalk-in closet, private full bath, and laundry. Low maintenance living includes lawn and

    Derek Greene The Greene Realty Group

    1845 Rosser Ln, Winchester, VA 22601
  • /21

    $1,550 Per Month

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

    443 N Loudoun St Unit 2, Winchester, VA 22601

    Beautiful 2 bedroom apartment just blocks from Old Town walking mall! Hardwood floors throughout, beautiful woodwork, nice size kitchen with stainless appliances, huge bathroom, and washer/dryer in unit! Upstairs are two bedrooms with wood floors, and parking is included in the rear! MUST have at least $3875 in monthly income and GOOD credit! One pet, case by case, must be up to date on vaccines

    Misty Weaver Samson Properties

    443 N Loudoun St Unit 2, Winchester, VA 22601
  • /64

    $615,900

    Sold Jan 05, 2026

    400 Handley Ave, Winchester, VA 22601

    • 3 Beds
    • 2.5 Baths
    • 2,575 Sq Ft
    • Built 1928

    Last Sold Summary

    • $239/SF
    • 12 Days On Market

    Current Estimated Value $624,998

    Last Listing Agent Jeff Boppe Long & Foster Real Estate, Inc.

    400 Handley Ave, Winchester, VA 22601
    • /31

      Est $251,932

      Not Listed For Sale

      545 Armour Dale, Winchester, VA 22601

      • 2 Beds
      • 1 Bath
      • 780 Sq Ft
      • Built 1954
      545 Armour Dale, Winchester, VA 22601

      Last Sold Summary

      • 10 Days On Market

      Last Listing Agent Laura King MarketPlace REALTY

  • /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
  • /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 BathGreat 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
  • /30

    $285,000

    Sold Jan 30, 2026

    1116 Opequon Ave, Winchester, VA 22601

    • 3 Beds
    • 1 Bath
    • 1,176 Sq Ft
    • Built 1972

    Last Sold Summary

    • $242/SF
    • 19 Days On Market

    Current Estimated Value $289,765

    Last Listing Agent Bradley Comstock ERA Oakcrest Realty, Inc.

    1116 Opequon Ave, Winchester, VA 22601
    • /8

      Est $241,947

      Not Listed For Sale

      521 Monticello St, Winchester, VA 22601

      • 2 Beds
      • 1.5 Baths
      • 1,064 Sq Ft
      • Built 1981
      521 Monticello St, Winchester, VA 22601

      Last Sold Summary

      • 4 Days On Market

      Last Listing Agent Ned Stock Berkshire Hathaway HomeServices PenFed Realty

  • /53

    $569,000

    • 4 Beds
    • 4 Baths
    • 2,489 Sq Ft

    687 Woodland Ave, Winchester, VA 22601

    Exceptional opportunity to own this beautifully crafted custom all-brick home on Winchester's desirable east side, nestled in an established neighborhood just minutes from Route 7, downtown Winchester, schools, shopping, dining, hospitals, and major commuter routes.Designed for both everyday living and entertaining, this impressive residence features an open-concept floor plan with gleaming

    Katy Donovan Keller Williams Realty

    687 Woodland Ave, Winchester, VA 22601
  • /24

    $1,600 Per Month

    • 2 Beds
    • 1.5 Baths
    • 2,202 Sq Ft
    • Townhouse for Rent

    235 Millwood Ave, Winchester, VA 22601

    Beautiful apt right in Old Town - grab your coffee across the street each morning, and relax on your patio each evening! This 2 bedroom 1.5 bath duplex is well cared for, with a welcoming front porch that leads into the open living room and kitchen with bar seating area. The kitchen is fully stocked with stainless appliances and tons of cabinetry and counter space. There is even storage space

    Misty Weaver Samson Properties

    235 Millwood Ave, Winchester, VA 22601
  • /59

    $855,000

    Sold May 28, 2026

    1540 Meadow Branch Ave, Winchester, VA 22601

    • 5 Beds
    • 4.5 Baths
    • 4,957 Sq Ft
    • Built 1996

    Last Sold Summary

    • 4% Below List Price
    • $172/SF
    • 70 Days On Market

    Current Estimated Value $863,585

    Last Listing Agent John Schroth Colony Realty

    1540 Meadow Branch Ave, Winchester, VA 22601
    • /22

      Est $254,611

      Not Listed For Sale

      514 Armour Dale, Winchester, VA 22601

      • 2 Beds
      • 1 Bath
      • 765 Sq Ft
      • Built 1955
      514 Armour Dale, Winchester, VA 22601

      Last Sold Summary

      • 4 Days On Market

      Last Listing Agent Katy Kidwell Burch Real Estate Group, LLC

Showing Results 201 - 240, Page 6 of 18

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