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 12 | 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

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

Hide 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. 106 Oleander Ct — photoPrice Reduced49Active

    $509,990

    3 bd · 3 ba · 2,264 sqft

    106 Oleander Ct, Winchester, VA

    Elizabeth Ellis · Brookfield Mid-Atlantic Brokerage, LLC

  2. 117 Glen Ridge Rd — photoPrice Reduced56Active

    $599,000

    3 bd · 4 ba · 2,646 sqft

    117 Glen Ridge Rd, Winchester, VA

    Joanne Cembrook · Coldwell Banker Premier

  3. 118 Nepal Ct — photo22Active

    $399,999

    4 bd · 4 ba · 2,000 sqft

    118 Nepal Ct, Winchester, VA

    James Thomas · New Home Star Virginia, LLC

  4. 1116 Woodstock Ln — photoPrice Reduced14Active

    $4,900,000

    1 bd · 1 ba · 44,000 sqft

    1116 Woodstock Ln, Winchester, VA

    Meridee A Powars · Link Realty Services LLC

  5. 601 Gray Ave — photo27Active

    $359,900

    3 bd · 2 ba · 1,743 sqft

    601 Gray Ave, Winchester, VA

    Walther Edgardo Vasquez Johnson · Samson Properties

  6. 1048 Woodland Ave — photoPrice Reduced1Active

    $335,000

    3 bd · 2 ba · 1,507 sqft

    1048 Woodland Ave, Winchester, VA

    Shane Bowman · Re/Max Roots

  7. 654 Treys Dr — photoPrice Reduced25Active

    $459,000

    3 bd · 2 ba · 2,025 sqft

    654 Treys Dr, Winchester, VA

    Donald A Butler · Virginia Property Group, Inc.

  8. 527 Grouse Dr — photoPrice Reduced31Active

    $379,900

    3 bd · 3 ba · 1,909 sqft

    527 Grouse Dr, Winchester, VA

    Amanda Lee Magana · RE/MAX Roots

  9. 230 Tranquil Wood Ln — photoPrice Reduced67Active

    $729,000

    3 bd · 3 ba · 3,129 sqft

    230 Tranquil Wood Ln, Winchester, VA

    Monique Rodriguez · Pearson Smith Realty LLC

  10. 300 Tavistock Dr — photoPrice Reduced79Active

    $894,900

    4 bd · 4 ba · 3,803 sqft

    300 Tavistock Dr, Winchester, VA

    Pamela Baber · Coldwell Banker Premier

  11. 3105 Apple Pie Ridge Rd — photoPrice Reduced37Active

    $674,999

    4 bd · 2 ba · 2,952 sqft

    3105 Apple Pie Ridge Rd, Winchester, VA

    Michael I Putnam · EXP Realty, LLC

  12. 303 Pembridge Dr — photoPrice Reduced37Active

    $377,000

    5 bd · 3 ba · 2,387 sqft

    303 Pembridge Dr, Winchester, VA

    Rebecca Sims · Century 21 Redwood Realty

  13. 3336 Hunting Ridge Rd — photoPrice Reduced50Active

    $539,000

    4 bd · 3 ba · 3,414 sqft

    3336 Hunting Ridge Rd, Winchester, VA

    Leslie O Carter · Carter Real Estate, Inc.

  14. 159 Lauck Dr — photoPrice Reduced40Active

    $415,000

    3 bd · 3 ba · 1,408 sqft

    159 Lauck Dr, Winchester, VA

    Jeanne Mezzatesta · Colony Realty

  15. 123 Kinross Dr — photoPrice Reduced56Active

    $599,999

    4 bd · 3 ba · 2,722 sqft

    123 Kinross Dr, Winchester, VA

    Sharon Farinholt · Realty ONE Group Old Towne

  16. 540 Bellview Ave — photo30Active

    $385,000

    3 bd · 1 ba · 1,280 sqft

    540 Bellview Ave, Winchester, VA

    Heloisa P Amar · Samson Properties

  17. 116 Swansong Pl — photo22Active

    $399,990

    3 bd · 4 ba · 2,026 sqft

    116 Swansong Pl, Winchester, VA

    Elizabeth Ellis · Brookfield Mid-Atlantic Brokerage, LLC

  18. Lot 39 Rossmann Blvd — photoPrice Reduced39Active

    $474,900

    4 bd · 3 ba · 2,023 sqft

    Lot 39 Rossmann Blvd, Winchester, VA

    Marisa L Varley · ERA Oakcrest Realty, Inc.

  19. 419 Summit Ave — photoPrice Reduced96Active

    $449,999

    5 bd · 3 ba · 1,887 sqft

    419 Summit Ave, Winchester, VA

    Waqas A Abbasi · Lifestyle Realty, LLC.

  20. 126 Marple Rd — photoPrice Reduced39Active

    $275,000

    3 bd · 2 ba · 1,170 sqft

    126 Marple Rd, Winchester, VA

    Roxanna D Grimes · RE/MAX Roots

  21. 11 W Germain St — photoPrice Reduced29Active

    $265,000

    2 bd · 1 ba · 1,734 sqft

    11 W Germain St, Winchester, VA

    Magnolia L Halkowitz · ERA Oakcrest Realty, Inc.

  22. 163 Margaret Ln — photoPrice Reduced37Active

    $389,000

    3 bd · 2 ba · 1,176 sqft

    163 Margaret Ln, Winchester, VA

    Michael Lee Sprague · Samson Properties

  23. 1856 Melvor Ln — photoPrice Reduced37Active

    $349,900

    2 bd · 2 ba · 1,219 sqft

    1856 Melvor Ln, Winchester, VA

    Natasha Roberts · Realty ONE Group Old Towne

  24. 136-8 Brookland Ct #8 — photoPrice Reduced27Active

    $244,900

    2 bd · 2 ba · 1,173 sqft

    136-8 Brookland Ct #8, Winchester, VA

    Amy A Longerbeam · Re/Max Roots

1…111213…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: 2026-10-01 12:23:39 UTC
  • Your local brokerage

    TO

    Thomas O'Leary

    Realty.com

    Lic. #0225245042

    Call Thomas

    Nearby areas

    ZIP codes

    • 22602 (193)
    • 22630 (168)
    • 22601 (96)
    • 22655 (63)
    • 22603 (62)
    • 22664 (45)
    • 22657 (44)
    • 22642 (41)

    Cities

    • Front Royal (144)
    • Stephens City (63)
    • Strasburg (45)
    • Woodstock (45)
    • Linden (41)
    • Berryville (34)
    • Cross Junction (32)
    • Stephenson (28)

    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

    September 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 · 77 sales · as of Sep 28, 2026

    Homes that sold · County records, as of Sep 11, 2026

    Median sale price
    $386,773$287,500–$523,750 typical range
    Price per sq. ft.
    $255
    Sales
    34
    Paid in cash
    29.4%

    Homes on the market · MLS, as of Sep 27, 2026–Sep 28, 2026

    Median list price
    $422,495
    Homes for sale
    334
    Median days on market
    28 days

    Price trend · Assessor repeat sales, as of Sep 30, 2026

    Year-over-year
    -12.1%

    Housing stock — every home in the area, not only the ones selling or listed · Assessor records, as of Sep 2, 2026

    Median home size
    1,620 sq. ft.