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2 Bedroom Homes in Winchester, VA
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3 bedsNew constructionWith a pool

2 Bedroom Homes in Winchester, VA

2 Bedroom Homes in Winchester, VA

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24 of 37 Listings
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2 Bedroom Homes in Winchester, VA

24 of 37 Listings

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TO

Thomas O'Leary

Realty.com

Lic. #0225245042

Call Thomas
  1. 161 Brookland Ct #2 — photoNew10Active

    $235,000

    2 bd · 2 ba · 1,257 sqft

    161 Brookland Ct #2, Winchester, VA

    Misty A Miller · OliveTree Property Group

  2. 159 Aspen Trl — photo54Active

    $295,000

    2 bd · 3 ba · 2,148 sqft

    159 Aspen Trl, Winchester, VA

    Kimberly C Baggett · EXP Realty, LLC

  3. 531 Cedar Grove Rd — photo83Active

    $675,000

    2 bd · 1 ba · 1,540 sqft

    531 Cedar Grove Rd, Winchester, VA

    Tyler Franklin Hazelwood · Virginia Real Estate

  4. 1414 S Braddock St — photo33Active

    $379,900

    2 bd · 2 ba · 1,578 sqft

    1414 S Braddock St, Winchester, VA

    Richard A. Kozlowski · Long & Foster Real Estate, Inc.

  5. 214 Molden Dr — photo6Active

    $230,000

    2 bd · 1 ba · 1,112 sqft

    214 Molden Dr, Winchester, VA

    Peter B Knapp · Real Broker, LLC

  6. 1125 Conway St — photo25Active

    $250,000

    2 bd · 1 ba · 870 sqft

    1125 Conway St, Winchester, VA

    Curtis W Siever · NextHome Realty Select

  7. 101 Delaware Trl — photo28Active

    $399,000

    2 bd · 2 ba · 2,094 sqft

    101 Delaware Trl, Winchester, VA

    Katherine Landi Jordan · Samson Properties

  8. 187 Valley Mill Rd — photo17Active

    $240,000

    2 bd · 1 ba · 997 sqft

    187 Valley Mill Rd, Winchester, VA

    Heloisa P Amar · Samson Properties

  9. 103 E Germain St — photo78Active

    $260,000

    2 bd · 2 ba · 1,068 sqft

    103 E Germain St, Winchester, VA

    Roxanna D Grimes · RE/MAX Roots

  10. 2640 Limestone Ct — photo8Active

    $289,900

    2 bd · 2 ba · 1,024 sqft

    2640 Limestone Ct, Winchester, VA

    Meridee A Powars · Link Realty Services LLC

  11. 2519 Hockman Ave — photo9Active

    $308,000

    2 bd · 2 ba · 800 sqft

    2519 Hockman Ave, Winchester, VA

    Meridee A Powars · Link Realty Services LLC

  12. 151 McCormick #203 — photoPrice Reduced36Active

    $319,900

    2 bd · 2 ba · 1,156 sqft

    151 McCormick #203, Winchester, VA

    Roxanna D Grimes · RE/MAX Roots

  13. 711 Fawn Dr — photo28Active

    $301,000

    2 bd · 3 ba · 920 sqft

    711 Fawn Dr, Winchester, VA

    Steve A DuBrueler · Coldwell Banker Premier

  14. 1024 Front Royal Pike — photo27Active

    $239,000

    2 bd · 1 ba · 1,014 sqft

    1024 Front Royal Pike, Winchester, VA

    Daniel J Whitacre · Colony Realty

  15. 212 Falcon Trl — photo25Active

    $324,900

    2 bd · 3 ba · 1,152 sqft

    212 Falcon Trl, Winchester, VA

    Jim Thomson · Realty ONE Group Old Towne

  16. 101 Tonto Trl — photo22Active

    $349,900

    2 bd · 1 ba · 1,140 sqft

    101 Tonto Trl, Winchester, VA

    Jim Thomson · Realty ONE Group Old Towne

  17. 1853 Rosser Ln — photo24Active

    $400,000

    2 bd · 2 ba · 1,186 sqft

    1853 Rosser Ln, Winchester, VA

    Sarena Baker · Realty FC

  18. 120 Scirocco Ln — photoPrice Reduced81Active

    $339,999

    2 bd · 2 ba · 1,824 sqft

    120 Scirocco Ln, Winchester, VA

    Nicole Leigh Mongold · Mountains Edge Realty LLC

  19. 211 Marple Rd — photoPrice Reduced45Active

    $399,900

    2 bd · 2 ba · 1,200 sqft

    211 Marple Rd, Winchester, VA

    Scott Wachtel · Century 21 Redwood Realty

  20. 207 Banbury Ter — photoPrice Reduced24Active

    $285,000

    2 bd · 2 ba · 1,200 sqft

    207 Banbury Ter, Winchester, VA

    Kristen Kerns · Roberts Realty Group, LLC

  21. 114 Inca Trl — photoPrice Reduced19Active

    $224,000

    2 bd · 2 ba · 1,566 sqft

    114 Inca Trl, Winchester, VA

    Marisa L Varley · ERA Oakcrest Realty, Inc.

  22. 107 Lawford Way — photoPrice Reduced47Active

    $459,990

    2 bd · 2 ba · 1,564 sqft

    107 Lawford Way, Winchester, VA

    Elizabeth Ellis · Brookfield Mid-Atlantic Brokerage, LLC

  23. 1826 Kershaw Ln — photo37Active

    $420,000

    2 bd · 2 ba · 1,431 sqft

    1826 Kershaw Ln, Winchester, VA

    Roxanna D Grimes · RE/MAX Roots

  24. 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

12

Explore Winchester homes

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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: 2026-09-05 16:31:40 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 · 78 sales · as of Aug 28, 2026

    Homes that sold · County records, as of Aug 12, 2026

    Median sale price
    $436,660$322,000–$559,900 typical range
    Price per sq. ft.
    $237
    Sales
    33
    Paid in cash
    30.3%

    Homes on the market · MLS, as of Aug 28, 2026–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
    3.8%

    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.