Realty.com
Buy

Start here

  • Homes for sale by state
  • Home buying tips
  • Before you start looking
  • The buying timeline

Afford it

  • Today's mortgage rates
  • Mortgage calculator
  • How much can I afford?
  • Get pre-approved

Make the deal

  • Writing a winning offer
  • Inspections & appraisals
  • Closing costs, itemized
  • Find a buyer's agent
Sell

Selling Options

  • What's my home worth?
  • Compare selling options
  • Get an instant cash offer
  • Buy before you sell

Resources

  • How selling works
  • When should I sell?
  • Home selling tips
  • Pricing your home
  • What's worth fixing first
  • Find a seller's agent
Home Loans
Find an Agent
Save searchAdvertiseSign In
Saved homesSaved searchesYour toursYour inquiriesRecently viewedAccount settings

Registered offenders on the map

Save search

Registered offenders on the map

Safety & registry resources

Review official public-safety information for any area from these government sources:

  • U.S. Dept. of Justice National Sex Offender Public Website (NSOPW)
  • FBI: state sex-offender registry directory
Winchester, VA Homes for Sale — Page 8 | Realty.com
Realty.com
Buy

Start here

  • Homes for sale by state
  • Home buying tips
  • Before you start looking
  • The buying timeline

Afford it

  • Today's mortgage rates
  • Mortgage calculator
  • How much can I afford?
  • Get pre-approved

Make the deal

  • Writing a winning offer
  • Inspections & appraisals
  • Closing costs, itemized
  • Find a buyer's agent
Save searchAdvertiseSign In
Saved homesSaved searchesYour toursYour inquiriesRecently viewedAccount settings
  • Rentals
  • Commercial

Registered offenders on the map

Save search
3 beds
334 listings
Sell

Selling Options

  • What's my home worth?
  • Compare selling options
  • Get an instant cash offer
  • Buy before you sell

Resources

  • How selling works
  • When should I sell?
  • Home selling tips
  • Pricing your home
  • What's worth fixing first
  • Find a seller's agent
Home Loans
Find an Agent
New construction
With a pool

Homes for Sale in Winchester, VA

Homes for Sale in Winchester, VA

Hide Map
24 of 334 Listings
Map

Homes for Sale in Winchester, VA

24 of 334 Listings

Your local brokerage

TO

Thomas O'Leary

Realty.com

Lic. #0225245042

Call Thomas
  1. 609 Quartzite Cir — photo41Active

    $500,900

    4 bd · 3 ba · 2,312 sqft

    609 Quartzite Cir, Winchester, VA

    Walther Edgardo Vasquez Johnson · Samson Properties

  2. 159 Williamson Rd — photoPrice Reduced11Active

    $579,990

    2 bd · 2 ba · 2,658 sqft

    159 Williamson Rd, Winchester, VA

    Greta Mirly Fernandez · New Home Star Virginia, LLC

  3. 1310 Whittier Ave — photoPrice Reduced26Active

    $400,000

    4 bd · 2 ba · 1,844 sqft

    1310 Whittier Ave, Winchester, VA

    sarah r hott · Realty ONE Group Old Towne

  4. 420 W Cork St — photo42Active

    $449,000

    4 bd · 2 ba · 1,932 sqft

    420 W Cork St, Winchester, VA

    Daniel J Whitacre · Colony Realty

  5. 1314 S Braddock St — photoPrice Reduced17Active

    $289,000

    3 bd · 1 ba · 960 sqft

    1314 S Braddock St, Winchester, VA

    Verria Hairston · Open Door Brokerage, LLC

  6. 913 Orchard Hill Dr — photoPrice Reduced45Active

    $315,000

    3 bd · 3 ba · 1,728 sqft

    913 Orchard Hill Dr, Winchester, VA

    Dallas D Croft · Samson Properties

  7. 135 Tye — photoPrice Reduced47Active

    $395,000

    3 bd · 3 ba · 1,970 sqft

    135 Tye, Winchester, VA

    Leah R REALTOR · Re/Max Roots

  8. 582 Miller Rd — photo76Active

    $1,650,000

    4 bd · 5 ba · 6,183 sqft

    582 Miller Rd, Winchester, VA

    Elizabeth Anne Cossette · ERA Oakcrest Realty, Inc.

  9. 336 Apple Valley Rd — photo34Active

    $715,000

    3 bd · 4 ba · 2,931 sqft

    336 Apple Valley Rd, Winchester, VA

    Sandra D Brill · Century 21 Redwood Realty

  10. 139 Poe Dr — photoPrice Reduced51Active

    $579,990

    4 bd · 3 ba · 2,442 sqft

    139 Poe Dr, Winchester, VA

    Sheila R Pack · RE/MAX Roots

  11. 342 Canyon Rd — photoPrice Reduced95Active

    $699,900

    5 bd · 4 ba · 4,264 sqft

    342 Canyon Rd, Winchester, VA

    Michele L Gibson · Samson Properties

  12. 111 Sovereign Ct — photo37Active

    $539,000

    4 bd · 4 ba · 2,884 sqft

    111 Sovereign Ct, Winchester, VA

    Kerry S Stinson · Berkshire Hathaway HomeServices PenFed Realty

  13. 204 Cochise Trl — photo32Active

    $310,000

    3 bd · 2 ba · 1,532 sqft

    204 Cochise Trl, Winchester, VA

    David K Spence · RE/MAX Roots

  14. 1311 Handley Ave — photo59Active

    $600,000

    3 bd · 2 ba · 3,483 sqft

    1311 Handley Ave, Winchester, VA

    Kimberly D Hurst · MarketPlace REALTY

  15. Light Rd — photo79Active

    $959,000

    3 bd · 3 ba · 2,000 sqft

    Light Rd, Winchester, VA

    Melissa A Johnston · ERA Oakcrest Realty, Inc.

  16. 102 Julie Ct — photoPrice Reduced101Active

    $829,900

    5 bd · 5 ba · 5,226 sqft

    102 Julie Ct, Winchester, VA

    Charles Witt · Nova Home Hunters Realty

  17. 135 S Kent St #202 — photoPrice Reduced18Active

    $250,000

    1 bd · 1 ba · 740 sqft

    135 S Kent St #202, Winchester, VA

    Sharon Farinholt · Realty ONE Group Old Towne

  18. 226 Summerfield Dr — photo106Active

    $849,000

    6 bd · 5 ba · 4,714 sqft

    226 Summerfield Dr, Winchester, VA

    Jeffrey Stack · CENTURY 21 New Millennium

  19. 503 Grouse — photoPrice Reduced16Active

    $345,000

    3 bd · 2 ba · 1,381 sqft

    503 Grouse, Winchester, VA

    Lisa S Gill · ERA Oakcrest Realty, Inc.

  20. 1826 Kershaw Ln — photoPrice Reduced37Active

    $400,000

    2 bd · 2 ba · 1,431 sqft

    1826 Kershaw Ln, Winchester, VA

    Roxanna D Grimes · RE/MAX Roots

  21. 404 Granite Ridge Dr — photo35Active

    $369,990

    3 bd · 3 ba · 1,893 sqft

    404 Granite Ridge Dr, Winchester, VA

    Elizabeth Ellis · Brookfield Mid-Atlantic Brokerage, LLC

  22. 687 Woodland Ave — photo52Active

    $569,000

    4 bd · 4 ba · 2,489 sqft

    687 Woodland Ave, Winchester, VA

    Kathrin Donovan · Keller Williams Realty

  23. 136-6 Brookland Ct #6 — photoPrice Reduced28Active

    $244,900

    2 bd · 2 ba · 1,173 sqft

    136-6 Brookland Ct #6, Winchester, VA

    Jeffrey W Konrady · Realty ONE Group Old Towne

  24. 108 Morgan St — photoPrice Reduced32Active

    $495,000

    3 bd · 2 ba · 1,505 sqft

    108 Morgan St, Winchester, VA

    Stacey S. Rowe · Real Broker LLC- Winchester

1…789…14

Explore Winchester homes

By price

  • Under $300K
  • Under $500K
  • Under $700K
  • Luxury

By bedrooms

  • 2 beds
  • 3 beds
  • 4 beds
  • 5 beds

By type

  • Single family
  • Townhomes
  • Condos
  • Manufactured homes
  • Multi-family homes
  • Co-ops
Realty.com

L. Custen Realty, Inc. d/b/a Realty.com/L. Custen Realty CT, LLC d/b/a Realty.com (Tom O’Leary-Broker)(CT properties only), 8323 Southwest Freeway, Suite 900, Houston, Texas 77074

Equal Housing OpportunityEqual Housing Lender

The information provided by this website is for the personal, non-commercial use of consumers and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Listing data is derived from various Multiple Listing Services; each source MLS and its required disclaimer are shown with the listings on the applicable page. Realty.com is an independently owned and operated brokerage.

© 2026 Realty.com. All rights reserved.·Privacy·Terms·California Privacy Rights·Accessibility·Licensing

Listing data & MLS disclosures

Bright MLS
The data relating to real estate for sale on this website appears in part through the BRIGHT Internet Data Exchange program, a voluntary cooperative exchange of property listing data between licensed real estate brokerage firms in which Realty.com participates, and is provided by BRIGHT through a licensing agreement. The information provided by this website is for the personal, non-commercial use of consumers and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Some properties which appear for sale on this website may no longer be available because they are under contract, have Closed or are no longer being offered for sale.
Listing information ©2026 BRIGHT MLS®. All Rights Reserved, Information deemed reliable but not guaranteed. Data Last Updated: 2026-09-15 15:21:16 UTC
  • By feature

    • New construction
    • With a pool

    Your local brokerage

    TO

    Thomas O'Leary

    Realty.com

    Lic. #0225245042

    Call Thomas

    Winchester, VA community profile

    Population
    27,805
    Median income
    $66,091
    Housing units
    12,270
    People per sq. mi.
    128.8
    Area
    215.8 sq. mi.

    Source: HJN community data

    Winchester housing market

    August 2026 · This period is still settling

    Winchester 12-month median sale price trend

    Selling at 99.0% of asking price

    Buyers here are paying below asking. MLS · 86 sales · as of Aug 31, 2026

    Homes that sold · County records, as of Aug 26, 2026

    Median sale price
    $387,990$285,000–$541,000 typical range
    Price per sq. ft.
    $236
    Sales
    85
    Paid in cash
    31.8%

    Homes on the market · MLS, as of Aug 31, 2026

    Median list price
    $429,450
    Homes for sale
    326
    Median days on market
    37 days

    Price trend · Assessor repeat sales, as of Aug 31, 2026

    Year-over-year
    -2.5%

    Housing stock — every home in the area, not only the ones selling or listed · Assessor records, as of Jul 29, 2026

    Median home size
    1,620 sq. ft.

    Nearby areas

    ZIP codes

    • 22602 (185)
    • 22630 (166)
    • 22601 (87)
    • 22603 (62)
    • 22655 (60)
    • 22657 (47)
    • 22664 (43)
    • 22642 (39)

    Cities

    • Front Royal (139)
    • Stephens City (60)
    • Strasburg (48)
    • Woodstock (43)
    • Linden (39)
    • Berryville (29)
    • Cross Junction (28)
    • Lake Frederick (27)