12,855

Winchester County, VA Homes

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  • /52

    $569,000

    Open Sun 1PM - 3PM
    • 4 Beds
    • 4 Baths
    • 2,489 Sq Ft

    687 Woodland Ave, Winchester, VA 22601

    ONE-OF-A-KIND HOME WITH INCREDIBLE FLEXIBILITY! This custom all-brick Winchester home offers a layout you simply don't find every day—4 bedrooms, 4 full baths, two main-level bedrooms, flexible private living spaces, a detached 2-car garage and NO HOA!Step inside to a bright, welcoming floor plan featuring beautiful hardwood floors, abundant natural light, custom built-ins and a cozy gas

    Katy Donovan Keller Williams Realty

    687 Woodland Ave, Winchester, VA 22601
  • /16

    $1,975 Per Month

    • 3 Beds
    • 2.5 Baths
    • 1,788 Sq Ft
    • Townhouse for Rent

    2040 Stoneleigh Dr, Winchester, VA 22601

    Charming Orchard Hill subdivision, twin/semi-detached Colonial residence offers a blend of elegance and comfort. Built in 2005, this home is in excellent condition, showcasing high-end features that cater to a refined lifestyle. Discover a warm and inviting interior with rich hardwood flooring that flows seamlessly throughout the main living areas. The spacious layout includes three generously

    Susan Raburn Long & Foster Real Estate, Inc.

    2040 Stoneleigh Dr, Winchester, VA 22601
  • /67

    $549,000

    Sold Jun 26, 2026

    1930 Harvest Dr, Winchester, VA 22601

    • 3 Beds
    • 2.5 Baths
    • 2,450 Sq Ft
    • Built 2003

    Last Sold Summary

    • 4% Below List Price
    • $224/SF
    • 37 Days On Market

    Current Estimated Value $550,328

    Last Listing Agent Dan Whitacre Colony Realty

    1930 Harvest Dr, Winchester, VA 22601
    • /53

      Est $478,629

      Not Listed For Sale

      102 Russelcroft Rd, Winchester, VA 22601

      • 4 Beds
      • 3.5 Baths
      • 3,518 Sq Ft
      • Built 1971
      102 Russelcroft Rd, Winchester, VA 22601

      Last Sold Summary

      • 7 Days On Market

      Last Listing Agent Sheila Pack RE/MAX Roots

  • /15

    $399,480

    New Construction Pending
    • 3 Beds
    • 4 Baths
    • 1,966 Sq Ft

    103 Marlow Ct, Winchester, VA 22602

    Rossum Crossing is Winchester's newest townhome community, which is located near shopping and dining. The St. Paul Townhome features 3 bedrooms, 2 1/2 baths, and a one-car garage. The main floor has an open-concept floorplan with a spacious family room that leads to a fully equipped kitchen. The kitchen has an island, pantry closet, and breakfast nook. This level also has a powder room. You can

    Dick Bryan New Home Star Virginia, LLC

    103 Marlow Ct, Winchester, VA 22602
  • /17

    $1,575 Per Month

    • 2 Beds
    • 2 Baths
    • 910 Sq Ft
    • Townhouse for Rent

    26 E Pall Mall St, Winchester, VA 22601

    Discover the charm of this beautifully renovated townhome, set to impress with major updates completed in 2024. This inviting residence features one large bedroom and one smaller bedroom, with 2 modern bathrooms, perfect for comfortable living. The cozy kitchen boasts granite countertops with stainless steel appliances, including a built-in microwave, dishwasher, and electric oven/range, making

    Shane Price Long & Foster Real Estate, Inc.

    26 E Pall Mall St, Winchester, VA 22601
  • /58

    $285,000

    Sold May 13, 2026

    301 Shawnee Ave, Winchester, VA 22601

    • 4 Beds
    • 1.5 Baths
    • 1,449 Sq Ft
    • Built 1940

    Last Sold Summary

    • 2% Above List Price
    • $197/SF
    • 4 Days On Market

    Current Estimated Value $284,991

    Last Listing Agent Barton Chasler Realty ONE Group Old Towne

    301 Shawnee Ave, Winchester, VA 22601
    • /27

      Est $337,443

      Not Listed For Sale

      2939 S Pleasant Valley Rd, Winchester, VA 22601

      • 3 Beds
      • 1.5 Baths
      • 1,199 Sq Ft
      • Built 1986
      2939 S Pleasant Valley Rd, Winchester, VA 22601

      Last Sold Summary

      • 2 Days On Market

      Last Listing Agent Anna Fox NextHome Realty Select

  • /33

    $348,000

    $12K PRICE DROP
    • 3 Beds
    • 2 Baths
    • 1,554 Sq Ft

    302 Wentworth Dr, Winchester, VA 22601

    Enjoy one-level living in this spectacularly located brick rambler, nestled in a quiet residential neighborhood while remaining conveniently close to Route 11 with easy access to I-81. The property currently has a long term month-to-month tenant paying under market value, offering flexibility for an owner-occupant or an investor seeking rental income with potential for increased rent. Situated on

    Heloisa Amar Samson Properties

    302 Wentworth Dr, Winchester, VA 22601
  • /16

    $1,700 Per Month

    • 2 Beds
    • 1 Bath
    • 936 Sq Ft
    • House for Rent

    380 Shawnee Ave, Winchester, VA 22601

    Charming 2-bedroom, 1-bath ranch home centrally located in the heart of Winchester. Hardwood floors inliving room and bedrooms. Fenced-in backyard with deck and storage shed. Minutes from ShenandoahUniversity, Old Town Winchester, Public Park, Shopping, and Restaurants. Minimum credit and income requirements. No past evictions.

    Marisa Varley ERA Oakcrest Realty, Inc.

    380 Shawnee Ave, Winchester, VA 22601
  • /2

    $625,000

    Sold Jun 15, 2026

    1416 Gordon Place, Winchester, VA 22601

    • 3 Beds
    • 2 Baths
    • 2,153 Sq Ft
    • Built 1998

    Last Sold Summary

    • $290/SF
    • 2 Days On Market

    Current Estimated Value $623,967

    Last Listing Agent Michele Gibson Samson Properties

    1416 Gordon Place, Winchester, VA 22601
    • /22

      Est $325,100

      Not Listed For Sale

      2935 S Pleasant Valley Rd, Winchester, VA 22601

      • 3 Beds
      • 1.5 Baths
      • 1,199 Sq Ft
      • Built 1986
      2935 S Pleasant Valley Rd, Winchester, VA 22601

      Last Sold Summary

      • 66 Days On Market

      Last Listing Agent Anna Fox NextHome Realty Select

  • /35

    $675,000

    • 3 Beds
    • 2.5 Baths
    • 1,650 Sq Ft

    112 W Germain St, Winchester, VA 22601

    100-Year-Old Downtown Winchester Charmer – Fully Reimagined in 2025!This stunning, fully restored century-old home seamlessly blends historic charm with high-end modern upgrades in the heart of downtown Winchester. Completely taken down to the studs and rebuilt in 2025, every detail was thoughtfully executed—nothing was overlooked. Proudly recognized with the 2025 Preservation of Historic

    Amanda Magana RE/MAX Roots

    112 W Germain St, Winchester, VA 22601
  • /63

    $2,400 Per Month

    • 3 Beds
    • 2.5 Baths
    • Townhouse for Rent

    646 Hemsworth Ln, Winchester, VA 22601

    Tucked within The Lofts at Creekside, the Upton II floor plan invites you to experience refined townhouse living at its finest. This three-bedroom, two-bath rental blends sophisticated design with everyday practicality, offering a lifestyle that feels both polished and effortlessly comfortable.Inside, high-end finishes set the tone from the moment you arrive. Stainless-steel appliances

    Vikas Goel Fairfax Realty of Tysons

    646 Hemsworth Ln, Winchester, VA 22601
  • /2

    $450,000

    Sold Jul 15, 2026

    320 Virginia Ave, Winchester, VA 22601

    • 3 Beds
    • 2.5 Baths
    • 1,549 Sq Ft
    • Built 1926

    Last Sold Summary

    • 3% Above List Price
    • $291/SF
    • 3 Days On Market

    Current Estimated Value $433,474

    Last Listing Agent Cindy Greenya Keller Williams Realty

    320 Virginia Ave, Winchester, VA 22601
    • /19

      Est $338,099

      Not Listed For Sale

      2927 S Pleasant Valley Rd, Winchester, VA 22601

      • 3 Beds
      • 1.5 Baths
      • 1,199 Sq Ft
      • Built 1983
      2927 S Pleasant Valley Rd, Winchester, VA 22601

      Last Sold Summary

      • 21 Days On Market

      Last Listing Agent Anna Fox NextHome Realty Select

  • /32

    $399,900

    $29K PRICE DROP
    • 2 Beds
    • 2 Baths
    • 1,419 Sq Ft

    118 1/2 E Cork St, Winchester, VA 22601

    Seeking the perfect blend of historic character and modern urban living? This exceptional Urban Lofts Condominium is just one and a half blocks from Old Town Winchester Walking Mall, offering easy access to restaurants, boutiques, entertainment, and vibrant downtown living. Originally built in the early 1900s, this beautifully updated home showcases exposed brick walls, timeless architectural

    Janet Flaherty Keller Williams Realty

    118 1/2 E Cork St, Winchester, VA 22601
  • /20

    $1,500 Per Month

    • 2 Beds
    • 1.5 Baths
    • 1,120 Sq Ft
    • Townhouse for Rent

    19 Jigsaw Place, Winchester, VA 22601

    Welcome to your new home! This cozy townhome was partially renovated this month to include new flooring, paint and other upgrades. Easy walk to several restaurants, shopping and very soon.....Publix! Off street parking, quiet and peaceful back yard to entertain with a deck.

    Joseph Clotzman Cambridge Premier Realty, LLC.

    19 Jigsaw Place, Winchester, VA 22601
  • /8

    $225,000

    Sold Oct 17, 2025

    Lot 6 Cedar Creek Grade, Winchester, VA

    • Land
    • 5.99 Acres
    • $37,563 per Acre

    Last Sold Summary

    • 40 Days On Market

    Last Listing Agent Lori Bales Keller Williams Realty

    Lot 6 Cedar Creek Grade, Winchester, VA
    • /21

      Est $322,254

      Not Listed For Sale

      2922 S Pleasant Valley Rd, Winchester, VA 22601

      • 3 Beds
      • 1.5 Baths
      • 1,060 Sq Ft
      • Built 1986
      2922 S Pleasant Valley Rd, Winchester, VA 22601

      Last Sold Summary

      • 12 Days On Market

      Last Listing Agent Anna Fox NextHome Realty Select

  • /33

    $429,000

    • 3 Beds
    • 2 Baths
    • 1,544 Sq Ft

    1412 S Loudoun St, Winchester, VA 22601

    Awesome Interior Photo's Coming Soon! Step inside this tastefully renovated brick ranch and feel instantly at home. Offering three comfortable bedrooms and two full baths, this property blends classic charm with thoughtful updates throughout. The main level features a bright, welcoming layout perfect for everyday living, while the lower level opens the door to exceptional flexibility — complete

    LESLIE WEBB Long & Foster Real Estate, Inc.

    1412 S Loudoun St, Winchester, VA 22601
  • /18

    $1,999 Per Month

    • 3 Beds
    • 2.5 Baths
    • 1,504 Sq Ft
    • Townhouse for Rent

    413 Tevis St, Winchester, VA 22601

    NEWER UNIT HAS AN OPEN KITCHEN WITH GRANITE COUNTERTOPS, STAINLESS STEEL APPLIANCES, LED LIGHTING AND 1 USB/OUTLET COMBO IN KITCHEN. WHOLE HOUSE WINDOW TREATMENTS INCLUDED, WASHER/DRYER AND PROGRAMABLE THERMOSTAT. RENT INCLUDES EXTERIOR LAWN CARE AND SNOW REMOVAL. WASHER AND DRYER INCLUDED. VERY NEAR TO 1-81 AND ALL SHOPPING

    Rajesh Cheruku FAB Realty LLC

    413 Tevis St, Winchester, VA 22601
  • /41

    $372,500

    Sold Jul 31, 2026

    1851 Melvor Ln, Winchester, VA 22601

    • 2 Beds
    • 2 Baths
    • 1,405 Sq Ft
    • Built 2004

    Last Sold Summary

    • 7% Below List Price
    • $265/SF
    • 117 Days On Market

    Current Estimated Value $382,767

    Last Listing Agent RoxAnn Grimes RE/MAX Roots

    1851 Melvor Ln, Winchester, VA 22601
    • /19

      Est $337,106

      Not Listed For Sale

      2951 S Pleasant Valley Rd, Winchester, VA 22601

      • 3 Beds
      • 1.5 Baths
      • 1,199 Sq Ft
      • Built 1989
      2951 S Pleasant Valley Rd, Winchester, VA 22601

      Last Sold Summary

      • 4 Days On Market

      Last Listing Agent Anna Fox NextHome Realty Select

  • /4

    $750,000

    Pending
    • Land
    • 1.33 Acres
    • $563,910 per Acre

    903 N Loudoun St, Winchester, VA 22601

    Lot 2 is half in Winchester City (tax ID # 134003-35) at 903 N. Loudoun St., & half in Frederick County (tax ID #54-A-50.) Mixed use zoning HR & B2. The county side has a brick residential structure, address 909 Martinsburg Pk, and city half is cleared land/ lot. The total sq ftg is 108,325 (2 & half acres.) Road frontage on Loudoun & Martinsburg PIke is 250 feet. The rear of lot is North

    Wendy Longerbeam Coldwell Banker Elite

    903 N Loudoun St, Winchester, VA 22601
  • /2

    $1,395 Per Month

    • 3 Beds
    • 1 Bath
    • 1,100 Sq Ft
    • Townhouse for Rent

    346 Gray Ave, Winchester, VA 22601

    This charming Colonial townhouse, built in 1930 and set for a major renovation in 2026, offers a unique blend of historic character and modern comfort. With three spacious bedrooms and a full bathroom, this home is perfect for those seeking a cozy retreat. The inviting hardwood and luxury vinyl plank flooring throughout enhances the warmth of the space. Located in a vibrant neighborhood, you'll

    Brandon Pifer Pifer Realty, LLC

    346 Gray Ave, Winchester, VA 22601
  • /38

    $315,000

    Sold Apr 24, 2026

    1610 S Loudoun St, Winchester, VA 22601

    • 4 Beds
    • 2 Baths
    • 1,344 Sq Ft
    • Built 1950

    Last Sold Summary

    • 2% Below List Price
    • $234/SF
    • 20 Days On Market

    Current Estimated Value $313,122

    Last Listing Agent Heloisa Amar Samson Properties

    1610 S Loudoun St, Winchester, VA 22601
    • /19

      Est $335,768

      Not Listed For Sale

      2947 S Pleasant Valley Rd, Winchester, VA 22601

      • 3 Beds
      • 1.5 Baths
      • 1,199 Sq Ft
      • Built 1986
      2947 S Pleasant Valley Rd, Winchester, VA 22601

      Last Sold Summary

      • 1 Day On Market

      Last Listing Agent Anna Fox NextHome Realty Select

  • /19

    $393,495

    New Construction
    • 4 Beds
    • 3.5 Baths
    • 1,889 Sq Ft

    652 Arden Ct, Winchester, VA 22601

    652 Arden Court is an attractive new 3 level townhome with brick backing to trees in Winchester's premier Meadow Branch community for September move-in. Our modern Adams floorplan features a 1-car garage, and a bedroom and full bathroom on the first floor. The main level with LVP Floors features a kitchen equipped with beautiful Quartz countertops, white cabinets, and stainless-steel appliances.

    D.R. Horton Builder
    652 Arden Ct, Winchester, VA 22601
  • /9

    $1,750 Per Month

    • 1 Bed
    • 1 Bath
    • 750 Sq Ft
    • Condo for Rent

    519 Amherst St Unit 201, Winchester, VA 22601

    Brand-new apartments in the heart of Winchester City! Just a few steps from the lovely Museum of the Shenandoah Valley and Old Town Mall. There are six newly constructed apartments, all located on the second floor and accessible by stairs. The apartments are situated above Boxwell Pharmacy, The Adult Care Center, and Stix & Stones. This apartment features one bedroom and one full bathroom and is

    Cara Wilkins MarketPlace REALTY

    519 Amherst St Unit 201, Winchester, VA 22601
  • /50

    $415,000

    Sold Dec 01, 2025

    290 Green St, Winchester, VA 22601

    • 4 Beds
    • 3 Baths
    • 2,255 Sq Ft
    • Built 2002

    Last Sold Summary

    • $184/SF
    • 13 Days On Market

    Current Estimated Value $423,808

    Last Listing Agent Angela Duncan MarketPlace REALTY

    290 Green St, Winchester, VA 22601
    • /28

      Est $335,879

      Not Listed For Sale

      2943 S Pleasant Valley Rd, Winchester, VA 22601

      • 3 Beds
      • 2 Baths
      • 1,479 Sq Ft
      • Built 1962
      2943 S Pleasant Valley Rd, Winchester, VA 22601

      Last Sold Summary

      • 14 Days On Market

      Last Listing Agent Anna Fox NextHome Realty Select

  • /88

    $639,900

    $10K PRICE DROP
    • 4 Beds
    • 3.5 Baths
    • 4,179 Sq Ft

    1529 Dalton Place, Winchester, VA 22601

    Roof 2017 - Water Heater 2017 - HVAC 2023. Welcome to 1529 Dalton Place, an exceptional home tucked away on a quiet cul-de-sac in one of Winchester's most desirable locations. Offering 4 spacious bedrooms, 3.5 bathrooms, and an expansive floor plan, this beautifully designed residence delivers the perfect blend of comfort, style, and functionality. From the moment you enter, you'll appreciate the

    RoxAnn Grimes RE/MAX Roots

    1529 Dalton Place, Winchester, VA 22601
  • /19

    $1,950 Per Month

    • 2 Beds
    • 2 Baths
    • 998 Sq Ft
    • Condo for Rent

    515 Amherst St, Winchester, VA 22601

    Brand-new apartments in the heart of Winchester City! Just a few steps from the lovely Museum of the Shenandoah Valley and Old Town Mall.There are six newly constructed apartments, all located on the second floor and accessible by stairs. The apartments are situated above Boxwell Pharmacy, The Adult Care Center, and Stix & Stones.This apartment features two bedrooms and two full

    Cara Wilkins MarketPlace REALTY

    515 Amherst St, Winchester, VA 22601
  • /83

    $650,000

    Sold Jan 21, 2026

    2708 Cassidy Ct, Winchester, VA 22601

    • 5 Beds
    • 3.5 Baths
    • 3,552 Sq Ft
    • Built 2010

    Last Sold Summary

    • $183/SF
    • 28 Days On Market

    Current Estimated Value $670,413

    Last Listing Agent Geri Deane Hunt Country Sotheby's International Realty

    2708 Cassidy Ct, Winchester, VA 22601
    • /39

      Est $335,282

      Not Listed For Sale

      2938 S Pleasant Valley Rd, Winchester, VA 22601

      • 3 Beds
      • 1.5 Baths
      • 1,376 Sq Ft
      • Built 1960
      2938 S Pleasant Valley Rd, Winchester, VA 22601

      Last Sold Summary

      • 3 Days On Market

      Last Listing Agent Danielle Snapp Coldwell Banker Premier

  • /89

    $539,000

    $71K PRICE DROP Under Contract
    • 3 Beds
    • 3.5 Baths
    • 3,140 Sq Ft

    1202 Handley Ave, Winchester, VA 22601

    Nestled on one of Winchester's most sought-after streets, this distinctive mid-century contemporary home offers a rare blend of character, space, and convenience just moments from downtown dining, shopping, and entertainment. Designed for comfortable main-level living, the home combines timeless architectural appeal with thoughtful functionality. The main level features a spacious primary suite

    Leah Marabella Realty ONE Group Old Towne

    1202 Handley Ave, Winchester, VA 22601
  • /8

    $1,395 Per Month

    • 3 Beds
    • 1 Bath
    • 900 Sq Ft
    • Townhouse for Rent

    1001 1/2 S Cameron St, Winchester, VA 22601

    This charming Colonial townhouse, built in 1930 and set for a major renovation in 2024, offers a unique blend of historic character and modern comfort. With three spacious bedrooms and a full bathroom, this home is perfect for those seeking a cozy retreat. The end-of-row design provides added privacy and natural light, enhancing the inviting atmosphere. Located in a vibrant neighborhood, you'll

    Brandon Pifer Pifer Realty, LLC

    1001 1/2 S Cameron St, Winchester, VA 22601
  • /47

    $289,900

    Sold Apr 28, 2026

    2963 Sorrell Ct, Winchester, VA 22601

    • 4 Beds
    • 2.5 Baths
    • 1,530 Sq Ft
    • Built 1990

    Last Sold Summary

    • $189/SF
    • 11 Days On Market

    Current Estimated Value $286,312

    Last Listing Agent Renzo Falla RE/MAX Real Estate Connections

    2963 Sorrell Ct, Winchester, VA 22601
    • /19

      Est $337,558

      Not Listed For Sale

      2918 S Pleasant Valley Rd, Winchester, VA 22601

      • 3 Beds
      • 1.5 Baths
      • 1,199 Sq Ft
      • Built 1981
      2918 S Pleasant Valley Rd, Winchester, VA 22601

      Last Sold Summary

      • 67 Days On Market

      Last Listing Agent Anna Fox NextHome Realty Select

Showing Results 281 - 320, Page 8 of 18

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