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
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

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
2 Bedroom Homes in Winchester, VA
41 listings

2 Bedroom Homes in Winchester, VA

2 Bedroom Homes in Winchester, VA

Hide Map
24 of 41 Listings
Map

2 Bedroom Homes in Winchester, VA

24 of 41 Listings

  1. 133 Blackfeet Trl — photo52Active

Your local brokerage

TO

Thomas O'Leary

Realty.com

Lic. #0225245042

Call Thomas

$249,000

2 bd · 1 ba · 756 sqft

133 Blackfeet Trl, Winchester, VA

Stephanie Feltner · Realty ONE Group Old Towne

  • 121 Lighthouse Ln — photo34Active

    $299,900

    2 bd · 2 ba · 1,254 sqft

    121 Lighthouse Ln, Winchester, VA

    Daniel J Whitacre · Colony Realty

  • 23 Jigsaw Pl — photo21Active

    $229,000

    2 bd · 2 ba · 1,160 sqft

    23 Jigsaw Pl, Winchester, VA

    Wendy R Longerbeam · Coldwell Banker Elite

  • 611 Fawn Dr — photo31Active

    $289,900

    2 bd · 1 ba · 1,577 sqft

    611 Fawn Dr, Winchester, VA

    Kathrin Donovan · Keller Williams Realty

  • 451 Lake Serene Dr — photoPrice Reduced102Active

    $759,000

    2 bd · 4 ba · 3,900 sqft

    451 Lake Serene Dr, Winchester, VA

    John S Scully IV · Colony Realty

  • 606 Elk Trl — photo59Active

    $289,000

    2 bd · 2 ba · 1,580 sqft

    606 Elk Trl, Winchester, VA

    Philip Virgil Asper · Keller Williams Realty/Lee Beaver & Assoc.

  • 316 Crow Dr — photo16Active

    $240,000

    2 bd · 1 ba · 906 sqft

    316 Crow Dr, Winchester, VA

    Matthew Peter Streiff · Keller Williams Realty

  • 3016 Siler Rd — photo80Active

    $649,900

    2 bd · 1 ba · 825 sqft

    3016 Siler Rd, Winchester, VA

    Edward L Beightol III · Cedar Creek Real Estate

  • 828 Woodland Ave — photo40Active

    $298,900

    2 bd · 2 ba · 1,079 sqft

    828 Woodland Ave, Winchester, VA

    Sylvia R Stoneberger · Samson Properties

  • 136-9 Brookland Ct #9 — photo32Active

    $249,900

    2 bd · 2 ba · 1,173 sqft

    136-9 Brookland Ct #9, Winchester, VA

    Daniel J Whitacre · Colony Realty

  • 2660 Daniel Ter — photo20Active

    $335,000

    2 bd · 2 ba · 1,352 sqft

    2660 Daniel Ter, Winchester, VA

    Elizabeth P Boxwell · MarketPlace REALTY

  • 5 E Hart St — photo29Active

    $284,900

    2 bd · 3 ba · 1,540 sqft

    5 E Hart St, Winchester, VA

    Leah Stafford Marabella · Realty ONE Group Old Towne

  • 302 Doe Trl Trl SW — photo15Active

    $235,000

    2 bd · 1 ba · 2,335 sqft

    302 Doe Trl Trl SW, Winchester, VA

    Avis Drummond · Long & Foster Real Estate, Inc.

  • 310 Bellview Ave — photo26Active

    $300,000

    2 bd · 1 ba · 1,097 sqft

    310 Bellview Ave, Winchester, VA

    Cynthia K. Greenya · Keller Williams Realty

  • 102 Buckwood Ln — photo24Active

    $368,000

    2 bd · 2 ba · 1,424 sqft

    102 Buckwood Ln, Winchester, VA

    Kathryn A Symenow · CENTURY 21 New Millennium

  • 107 Little River Dr — photoPrice Reduced23Active

    $250,000

    2 bd · 1 ba · 900 sqft

    107 Little River Dr, Winchester, VA

    Erin M Kavanagh · EXP Realty, LLC

  • 100 Gooseberry Dr — photoPrice Reduced30Active

    $499,000

    2 bd · 3 ba · 2,679 sqft

    100 Gooseberry Dr, Winchester, VA

    Lisa A Behr · Hunt Country Sotheby's International Realty

  • 531 Cedar Grove Rd — photoPrice Reduced83Active

    $659,900

    2 bd · 1 ba · 1,540 sqft

    531 Cedar Grove Rd, Winchester, VA

    Tyler Franklin Hazelwood · Virginia Real Estate

  • 1847 Melvor Ln — photoPrice Reduced98Active

    $339,900

    2 bd · 2 ba · 1,234 sqft

    1847 Melvor Ln, Winchester, VA

    Lisette B. Turner · Century 21 Redwood Realty

  • 1125 Conway St — photo25Active

    $250,000

    2 bd · 1 ba · 870 sqft

    1125 Conway St, Winchester, VA

    Curtis W Siever · NextHome Realty Select

  • 187 Valley Mill Rd — photoPrice Reduced17Active

    $220,000

    2 bd · 1 ba · 997 sqft

    187 Valley Mill Rd, Winchester, VA

    Heloisa P Amar · Samson Properties

  • 103 E Germain St — photoPrice Reduced78Active

    $240,000

    2 bd · 2 ba · 1,068 sqft

    103 E Germain St, Winchester, VA

    Roxanna D Grimes · RE/MAX Roots

  • 123 Harvest Ridge Dr — photoPrice Reduced62Active

    $549,000

    2 bd · 2 ba · 2,205 sqft

    123 Harvest Ridge Dr, Winchester, VA

    Brian Keith Yoder · Realty ONE Group Old Towne

  • 2519 Hockman Ave — photoPrice Reduced9Active

    $299,900

    2 bd · 2 ba · 800 sqft

    2519 Hockman Ave, Winchester, VA

    Meridee A Powars · Link Realty Services LLC

  • 12

    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

    Your local brokerage

    TO

    Thomas O'Leary

    Realty.com

    Lic. #0225245042

    Call Thomas

    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: 2026-10-22 17:21:54 UTC

    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

    Winchester 12-month median sale price trend

    Selling at 100.0% of asking price

    Sales here are closing essentially at asking. MLS · 91 sales · as of Sep 30, 2026

    Homes that sold · County records, as of Sep 30, 2026

    Median sale price
    $399,000$306,725–$581,250 typical range
    Price per sq. ft.
    $252
    Sales
    119
    Paid in cash
    36.1%

    Homes on the market · MLS, as of Sep 27, 2026–Sep 30, 2026

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

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

    Year-over-year
    -6.3%

    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.