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

Save search

Map layers

Safety

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 | 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

350 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
Save search
3 bedsNew construction

Homes for Sale in Winchester, VA

Homes for Sale in Winchester, VA

Show Map
24 of 350 Listings
Map

Homes for Sale in Winchester, VA

24 of 350 Listings

Your local brokerage

TO

Thomas O'Leary

Realty.com

Lic. #0225245042

Call Thomas
  1. Homesite 1 Monteith Dr — photoNew27Active

    $384,990

    3 bd · 4 ba · 1,756 sqft

    Homesite 1 Monteith Dr, Winchester, VA

    Brittany Newman · DRB Group Realty, LLC

  2. 112 Killaney Ct — photoNew56Active

    $620,000

    4 bd · 4 ba · 3,700 sqft

    112 Killaney Ct, Winchester, VA

    David K Spence · RE/MAX Roots

  3. 134 Wilkins Dr — photo67Active

    $399,900

    4 bd · 2 ba · 2,886 sqft

    134 Wilkins Dr, Winchester, VA

    Justin Mistretta · Berkshire Hathaway HomeServices PenFed Realty

  4. 2631 Jones Rd — photo1Active

    $352,000

    3 bd · 2 ba · 1,192 sqft

    2631 Jones Rd, Winchester, VA

    Karen M O'Hare · Colony Realty

  5. 15 W Germain St — photo15Active

    $219,000

    4 bd · 2 ba · 1,251 sqft

    15 W Germain St, Winchester, VA

    Minh-Thieng T. Le · Levi Clarke, LLC

  6. 602 Patterson Ave — photo12Active

    $295,000

    3 bd · 1 ba · 1,066 sqft

    602 Patterson Ave, Winchester, VA

    Steven Koleno · BEYCOME BROKERAGE REALTY LLC

  7. 2691 Senseny Rd — photo46Active

    $359,900

    3 bd · 1 ba · 1,120 sqft

    2691 Senseny Rd, Winchester, VA

    Daniel J Whitacre · Colony Realty

  8. 18 Williamson Rd — photo25Active

    $598,990

    3 bd · 2 ba · 3,056 sqft

    18 Williamson Rd, Winchester, VA

    Cindy Lorena Gomez · New Home Star Virginia, LLC

  9. 694 Round Hill Rd — photo49Active

    $300,000

    3 bd · 1 ba · 816 sqft

    694 Round Hill Rd, Winchester, VA

    Cynthia Lee · RE/MAX Roots

  10. 113 Malbec Ct — photo28Active

    $677,130

    4 bd · 3 ba · 3,397 sqft

    113 Malbec Ct, Winchester, VA

    Cindy Lorena Gomez · New Home Star Virginia, LLC

  11. 29 Williamson Rd — photo21Active

    $549,990

    4 bd · 3 ba · 3,747 sqft

    29 Williamson Rd, Winchester, VA

    Cindy Lorena Gomez · New Home Star Virginia, LLC

  12. 230 Crinoline Ln — photo13Active

    $479,777

    3 bd · 2 ba · 1,232 sqft

    230 Crinoline Ln, Winchester, VA

    Leo J Smith · CENTURY 21 New Millennium

  13. 250 Monteith Dr — photo4Active

    $374,990

    3 bd · 4 ba · 1,790 sqft

    250 Monteith Dr, Winchester, VA

    Brittany Newman · DRB Group Realty, LLC

  14. 508 Lanny Dr — photo40Active

    $400,000

    3 bd · 2 ba · 2,185 sqft

    508 Lanny Dr, Winchester, VA

    Marcella S Cantatore · Corcoran McEnearney

  15. Homesite 90 Shuoner Ct — photo25Active

    $389,990

    4 bd · 5 ba · 2,250 sqft

    Homesite 90 Shuoner Ct, Winchester, VA

    James Thomas · New Home Star Virginia, LLC

  16. 942 Beehive Way — photo1Active

    $359,900

    3 bd · 3 ba · 2,000 sqft

    942 Beehive Way, Winchester, VA

    Bridget V Aikens · Colony Realty

  17. Homesite 91 Shuoner Ct — photo25Active

    $374,990

    4 bd · 5 ba · 2,250 sqft

    Homesite 91 Shuoner Ct, Winchester, VA

    James Thomas · New Home Star Virginia, LLC

  18. 381 Hidden Valley Ln — photo98Active

    $699,000

    3 bd · 2 ba · 1,778 sqft

    381 Hidden Valley Ln, Winchester, VA

    Daniel J Whitacre · Colony Realty

  19. 2018 Colin Dr — photo54Active

    $499,000

    3 bd · 3 ba · 2,510 sqft

    2018 Colin Dr, Winchester, VA

    Angela R. Duncan · MarketPlace REALTY

  20. 134 Hudson Ave — photo52Active

    $375,000

    4 bd · 2 ba · 2,322 sqft

    134 Hudson Ave, Winchester, VA

    Cara L Wilkins · MarketPlace REALTY

  21. 1785 Berryville Pike — photo7Active

    $199,000

    2 bd · 1 ba · 718 sqft

    1785 Berryville Pike, Winchester, VA

    Meridee A Powars · Link Realty Services LLC

  22. 117 Amberfield Ct — photo18Active

    $493,000

    3 bd · 2 ba · 1,784 sqft

    117 Amberfield Ct, Winchester, VA

    Verria Hairston · Open Door Brokerage, LLC

  23. 1281 Merrimans Ln — photo107Active

    $2,500,000

    4 bd · 7 ba · 6,219 sqft

    1281 Merrimans Ln, Winchester, VA

    Dallas D Croft · Samson Properties

  24. 460 Cattail Rd — photo78Active

    $624,000

    4 bd · 4 ba · 3,290 sqft

    460 Cattail Rd, Winchester, VA

    Ned S Stock · Berkshire Hathaway HomeServices PenFed Realty

12…15

Explore Winchester homes

By price

  • Homes Under $300K
  • Homes Under $400K
  • Homes Under $500K
  • Homes Under $600K
  • Homes Under $700K

By bedrooms

  • 2 Bedroom Homes
  • 3 Bedroom Homes
  • 4 Bedroom Homes
  • 5 Bedroom Homes

By type

  • Single-Family Homes
  • Townhomes

By feature

  • New Construction Homes
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: 2026-11-01 19:51:15 UTC
  • Your local brokerage

    TO

    Thomas O'Leary

    Realty.com

    Lic. #0225245042

    Call Thomas

    Nearby areas

    ZIP codes

    • 22602 (181)
    • 22630 (173)
    • 22601 (99)
    • 22603 (73)
    • 22655 (71)
    • 22642 (48)
    • 22657 (40)
    • 22664 (38)

    Cities

    • Front Royal (147)
    • Stephens City (71)
    • Linden (48)
    • Strasburg (40)
    • Woodstock (38)
    • Berryville (34)
    • Cross Junction (30)
    • Stephenson (24)

    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

    October 2026 · This period is still settling

    Winchester 12-month median sale price trend

    Selling at 100.0% of asking price

    Sales here are closing essentially at asking. MLS · 76 sales · as of Oct 30, 2026

    Homes that sold · County records, as of Oct 13, 2026

    Median sale price
    $508,579$325,000–$720,000 typical range
    Price per sq. ft.
    $242
    Sales
    41
    Paid in cash
    48.8%

    Homes on the market · MLS, as of Oct 25, 2026–Oct 30, 2026

    Median list price
    $425,000
    Homes for sale
    343
    Median days on market
    29 days

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

    Year-over-year
    29.4%

    Housing stock — every home in the area, not only the ones selling or listed · Assessor records, as of Sep 30, 2026

    Median home size
    1,620 sq. ft.