37,092

Winchester, VA Homes

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  • /30

    $349,900

    Under Contract
    • 3 Beds
    • 2 Baths
    • 1,412 Sq Ft

    2561 Apple Pie Ridge Rd, Winchester, VA 22603

    Welcome home to this beautifully updated rambler, offering comfort, character, and room to grow. The spacious front living room features gleaming hardwood floors and a large picture window that fills the space with natural light.Just off the garage, the remodeled den provides versatile living space perfect for a family room, home office, or recreation area. Recent updates include new drywall,

    Agent Photo

    Brock Harris

    Samson Properties

    2561 Apple Pie Ridge Rd, Winchester, VA 22603
  • /74

    Starting at $1,700 Plus Fees

    • 1 - 4 Beds

    230 Spring St, Winchester, VA 22601

    Modern designs, elegant finishes, and the most desirable amenities await you at the area's newest apartment home living destination, the Local. Our Winchester apartments come in one, two, three, and four-bedroom floorplans, each featuring spacious and adaptable layouts. Various interior extras adorn them including an open floorplan concept, walk-in closets, in-unit washers/dryers, and more. As a

    The Local

    230 Spring St, Winchester, VA 22601
  • /4

    $190,000

    Sold Nov 25, 2025

    303 Barrington Ln, Winchester, VA 22601

    • 2 Beds
    • 1 Bath
    • 894 Sq Ft
    • Built 1994

    Last Sold Summary

    • $213/SF
    • 86 Days On Market

    Current Estimated Value $199,768

    Last Listing Agent Jim Stafford ERA Oakcrest Realty, Inc.

    303 Barrington Ln, Winchester, VA 22601
    • /29

      Not Listed For Sale

      709 Panther Dr, Winchester, VA 22602

      • 3 Beds
      • 2 Baths
      • 1,217 Sq Ft
      • Built 2025
      709 Panther Dr, Winchester, VA 22602

      Last Sold Summary

      • 4 Days On Market

      Last Listing Agent Lisa Gill ERA Oakcrest Realty, Inc.

  • /3

    $675,000

    Coming Soon
    • 5 Beds
    • 3 Baths
    • 4,030 Sq Ft

    146 Stonebrook Rd, Winchester, VA 22602

    Spacious ranch home on a beautiful 1-acre lot in the highly desirable Stonebrook Farms community! Surrounded by mature trees and offering a peaceful setting, this home combines the space of country living with the convenience of being just minutes from shopping, dining, medical facilities, and all that Winchester has to offer. Designed with flexibility in mind, this home features 5 bedrooms and 3

    Agent Photo

    Bradley Comstock

    ERA Oakcrest Realty, Inc.

    146 Stonebrook Rd, Winchester, VA 22602
  • /12

    $1,500 Per Month

    • 1 Bed
    • 1 Bath
    • 9,518 Sq Ft
    • Condo for Rent

    44 S Loudoun St Unit 7, Winchester, VA 22601

    Historically charming one-bedroom apartment located on the famous downtown walking mall. Enjoy stylish living amongst shops, restaurants, museums, and parks. Only minutes to Winchester Medical Center, Shenandoah University and commuter routes

    Agent Photo

    Brock Harris

    Samson Properties

    44 S Loudoun St Unit 7, Winchester, VA 22601
  • /51

    $425,000

    Sold Jun 10, 2026

    104 Van Buren Place, Winchester, VA 22602

    • 4 Beds
    • 2.5 Baths
    • 1,714 Sq Ft
    • Built 1990

    Last Sold Summary

    • 1% Above List Price
    • $248/SF
    • 6 Days On Market

    Current Estimated Value $420,528

    Last Listing Agent Leah Marabella Realty ONE Group Old Towne

    104 Van Buren Place, Winchester, VA 22602
    • /52

      Not Listed For Sale

      170 Munsee Cir, Winchester, VA 22602

      • 4 Beds
      • 3.5 Baths
      • 1,889 Sq Ft
      • Built 2025
      170 Munsee Cir, Winchester, VA 22602

      Last Sold Summary

      • 20 Days On Market

      Last Listing Agent Brooks Sears Pearson Smith Realty, LLC

  • /48

    $399,900

    $15K PRICE DROP
    • 3 Beds
    • 2.5 Baths
    • 1,970 Sq Ft

    105 Tye Ct, Winchester, VA 22602

    Enjoy townhouse living with a view at 105 Tye Ct.! This desirable end-unit townhouse overlooks the neighborhood instead of facing rows of neighboring townhomes, offering a more open and private feel. Only 3 years old, this former model home features upgraded finishes and custom touches not found in many of the other units. Featuring 3 bedrooms, 2.5 bathrooms, and a finished basement, this home

    Agent Photo

    Frank Armstrong, IV

    Colony Realty

    105 Tye Ct, Winchester, VA 22602
  • /38

    Starting at $1,837 Plus Fees

    • 1 - 3 Beds

    424 Ridgewood Ln, Winchester, VA 22601

    Welcome to Meadow Branch, where luxury and convenience are standard. Our community offers beautiful 1,2 and 3 bedroom apartment homes. Community means convenience and at Meadow Branch, everything you need is nearby. We conveniently located adjacent to Winchester Medical Center and 2 miles from Old Town Winchester.

    Denstock Meadow Branch LLC

    424 Ridgewood Ln, Winchester, VA 22601
  • /57

    $625,000

    Sold Oct 31, 2025

    101 Arthur Ln, Winchester, VA 22602

    • 5 Beds
    • 3.5 Baths
    • 4,787 Sq Ft
    • Built 2007

    Last Sold Summary

    • $131/SF
    • 5 Days On Market

    Current Estimated Value $633,932

    Last Listing Agent Scotti Sellers Compass

    101 Arthur Ln, Winchester, VA 22602
    • /12

      Not Listed For Sale

      124 Powhatan Trail, Winchester, VA 22602

      • 3 Beds
      • 3 Baths
      • 1,850 Sq Ft
      • Built 2025
      124 Powhatan Trail, Winchester, VA 22602

      Last Sold Summary

      • 197 Days On Market

      Last Listing Agent Jim Thomson Realty ONE Group Old Towne

  • /32

    $375,000

    $15K PRICE DROP Under Contract
    • 2 Beds
    • 2 Baths
    • 1,554 Sq Ft

    151 Mccormick Cir Unit 201, Winchester, VA 22602

    Experience Effortless 55+ Living at Winchester Landing – The Sapphire by Ryan Homes Discover the perfect blend of comfort and convenience in the Sapphire model, a spacious single-level condo offering over 1,500 sq. ft. of thoughtfully designed living space. The open-concept layout seamlessly connects a modern kitchen, large island, and bright great room, creating an inviting space ideal for

    Agent Photo

    Rhonda Shade

    ERA Oakcrest Realty, Inc.

    151 Mccormick Cir Unit 201, Winchester, VA 22602
  • /12

    $1,900 Per Month

    • 2 Beds
    • 2 Baths
    • 1,600 Sq Ft
    • Condo for Rent

    21 S Stewart St Unit 4, Winchester, VA 22601

    Charming Remodeled 2-Bedroom Apartment Near Old Town Winchester!Enjoy the perfect mix of comfort and convenience in this beautifully remodeled 2 bedroom, 2 bathroom apartment located just steps from historic Old Town Winchester. This spacious unit features modern updates, in-unit laundry, and a fully fenced private yard—ideal for relaxing or entertaining. You'll also love the generous storage

    Agent Photo

    Frank Armstrong, IV

    Colony Realty

    21 S Stewart St Unit 4, Winchester, VA 22601
  • /70

    $535,000

    Sold Jun 05, 2026

    3691 Green Spring Rd, Winchester, VA 22603

    • 4 Beds
    • 2 Baths
    • 1,612 Sq Ft
    • Built 1970

    Last Sold Summary

    • 7% Above List Price
    • $332/SF
    • 1 Day On Market

    Current Estimated Value $526,817

    Last Listing Agent Bailey Cooper RE/MAX Gateway

    3691 Green Spring Rd, Winchester, VA 22603
    • /14

      Est $473,999

      Not Listed For Sale

      2620 Stonegate Dr, Winchester, VA 22601

      • 5 Beds
      • 3 Baths
      • 2,974 Sq Ft
      • Built 1995
      2620 Stonegate Dr, Winchester, VA 22601

      Last Sold Summary

      • 10 Days On Market

      Last Listing Agent Anthony Adamovich Key Move Properties, LLC.

  • /2

    $500,900

    • 4 Beds
    • 3 Baths
    • 2,312 Sq Ft

    609 Quartzite Cir, Winchester, VA 22601

    Welcome to 609 Quartzite Circle! A beautifully maintained 4-bedroom, 3-bath home offering a spacious and functional layout designed for modern living. The main level features inviting living spaces, hardwood flooring, and an open kitchen with ample cabinetry and table space. The primary suite includes a walk-in closet and a private bath with a soaking tub, while the finished lower level provides

    Agent Photo

    Walther Vasquez Johnson

    Samson Properties

    609 Quartzite Cir, Winchester, VA 22601
  • /44

    Starting at $1,682

    Total Monthly Price

    • 2 - 3 Beds

    121 Fay St, Winchester, VA 22602

    Live on your own terms with Fay Street Apartments. Find the comfort and convenience you crave among our one, two, and three-bedroom residences, on our well-kept premises, and in the nearby, city of Winchester, VA in the Shenandoah Valley. The property is conveniently located near top employers like Shenandoah University and Valley Health System. Our apartments open doors to a myriad of

    Fay Street Apartments

    121 Fay St, Winchester, VA 22602
  • /20

    $388,990

    Sold Jul 29, 2026

    110 Sioux Loop, Winchester, VA 22602

    • 4 Beds
    • 3.5 Baths
    • 1,889 Sq Ft
    • Built 2026

    Move in Ready Sold Summary

    • 6% Below List Price
    • $206/SF
    • 35 Days On Market

    D.R. Horton Retreat at Winding Creek - Townhomes

    110 Sioux Loop, Winchester, VA 22602
    • /68

      Est $652,647

      Not Listed For Sale

      800 Kennedy Dr, Winchester, VA 22601

      • 5 Beds
      • 4 Baths
      • 2,639 Sq Ft
      • Built 2009
      800 Kennedy Dr, Winchester, VA 22601

      Last Sold Summary

      • 22 Days On Market

      Last Listing Agent Cindy Greenya Keller Williams Realty

  • /2

    $195,000

    • 3 Beds
    • 1 Bath
    • 932 Sq Ft

    150 Cedar Grove Rd, Winchester, VA 22603

    This property is being sold strictly as-is, where-is. The mobile home on the property is believed to date back to the 1960s and is in need of significant renovation. Previous occupants began updating the home but did not complete the work. The property also features a garage-style building with a work bay and office space equipped with air conditioning, offering excellent potential for storage,

    Agent Photo

    Frank Armstrong, IV

    Colony Realty

    150 Cedar Grove Rd, Winchester, VA 22603
  • /13

    $1,500 Per Month

    • 2 Beds
    • 1 Bath
    • 1,100 Sq Ft
    • House for Rent

    21 S Stewart St Unit 2, Winchester, VA 22601

    2 Bedroom Apartment for Rent – Downtown Winchester Great 2nd-floor apartment located in downtown Winchester with 2 bedrooms and 1 bathroom. This home is just a short walk from Old Town Winchester, giving you easy access to local restaurants, shops, and entertainment. The apartment features very spacious bedrooms, a comfortable family room, and a fully enclosed back porch, perfect for relaxing or

    Agent Photo

    Frank Armstrong, IV

    Colony Realty

    21 S Stewart St Unit 2, Winchester, VA 22601
  • /89

    $595,000

    Sold Aug 08, 2025

    121 Carnmore Dr, Winchester, VA 22602

    • 5 Beds
    • 4 Baths
    • 3,086 Sq Ft
    • Built 2005

    Last Sold Summary

    • $193/SF
    • 103 Days On Market

    Current Estimated Value $608,928

    Last Listing Agent Angela Duncan MarketPlace REALTY

    121 Carnmore Dr, Winchester, VA 22602
    • /34

      Est $604,988

      Not Listed For Sale

      720 Beehive Way, Winchester, VA 22601

      • 4 Beds
      • 3.5 Baths
      • 2,571 Sq Ft
      • Built 2006
      720 Beehive Way, Winchester, VA 22601

      Last Sold Summary

      • 53 Days On Market

      Last Listing Agent Amy Emerson-Kerns Beltway Realty, LLC.

  • /13

    $274,999

    Under Contract
    • 2 Beds
    • 2.5 Baths
    • 1,080 Sq Ft

    206 Kimberly Way, Winchester, VA 22601

    Beautifully remodeled 2-bedroom, 2.5-bath townhouse that's ready for you to move right in! This home features a stunning updated kitchen with granite countertops and stainless steel appliances, along with modern finishes throughout. Major improvements include a new roof and heat pump installed in 2023, providing added comfort and peace of mind. Spacious living areas, updated bathrooms, and

    Agent Photo

    Frank Armstrong, IV

    Colony Realty

    206 Kimberly Way, Winchester, VA 22601
  • /55

    Starting at $1,795 Plus Fees

    • 1 - 3 Beds

    1981 Randolph Place, Winchester, VA 22601

    Welcome to Stuart Hill Apartments — comfortable living in scenic Winchester, VA. Nestled in the picturesque Shenandoah Valley and just minutes from Historic Downtown Winchester, dining, shopping, Shenandoah University, and Winchester Medical Center, this well-maintained community offers spacious 1-, 2-, and 3-bedroom homes with full-size in-unit washers and dryers, generous closet space, and

    Stuart Hill

    1981 Randolph Place, Winchester, VA 22601
  • /18

    $644,990

    Sold Sep 04, 2025

    126 Wagtail Ln, Winchester, VA 22603

    • 3 Beds
    • 2 Baths
    • 3,122 Sq Ft
    • Built 2025

    Move in Ready Sold Summary

    • $207/SF
    • 0 Days On Market

    Brookfield Residential Hiatt Pointe at Snowden Bridge - 55+ Single Family Homes Collection

    126 Wagtail Ln, Winchester, VA 22603
    • /36

      Est $376,994

      Not Listed For Sale

      511 S Kent St, Winchester, VA 22601

      • 3 Beds
      • 2.5 Baths
      • 1,800 Sq Ft
      • Built 1900
      511 S Kent St, Winchester, VA 22601

      Last Sold Summary

      • 4 Days On Market

      Last Listing Agent Lawrence Lessin Homes By Owner, Inc.

  • /54

    $610,000

    $20K PRICE DROP
    • 4 Beds
    • 3.5 Baths
    • 4,120 Sq Ft

    211 Flanagan Dr, Winchester, VA 22602

    Pictures coming soon. Prime Location in Raven Wing!This beautiful Colonial home offers the perfect combination of comfort, convenience, and modern updates. Located in the desirable Raven Wing community, you'll enjoy easy access to schools, shopping, restaurants, and commuter routes.Recent improvements include a new roof (2025), hot water heater (3 years old), sump pump (1.5 years old),

    Agent Photo

    Ned Stock

    Berkshire Hathaway HomeServices PenFed Realty

    211 Flanagan Dr, Winchester, VA 22602
  • /22

    $2,225 Per Month

    • 3 Beds
    • 1.5 Baths
    • 1,260 Sq Ft
    • Townhouse for Rent

    314 E Piccadilly St, Winchester, VA 22601

    Freshly updated and just two blocks from the Old Town Pedestrian Mall — this charming downtown duplex is the perfect blend of historic character and modern comfort. Recently renovated, this 3-bedroom, 1.5-bath home features gleaming hardwood floors, beautifully updated tile bathrooms, stainless steel appliances, abundant natural light, and timeless architectural details throughout. Enjoy relaxing

    Agent Photo

    Jeanne Mezzatesta

    Colony Realty

    314 E Piccadilly St, Winchester, VA 22601
  • /15

    $509,990

    Sold Mar 11, 2026

    108 Carnation Way, Winchester, VA 22603

    • 3 Beds
    • 2 Baths
    • 2,050 Sq Ft
    • Built 2026

    Move in Ready Sold Summary

    • $249/SF
    • 9 Days On Market

    Brookfield Residential Hiatt Pointe at Snowden Bridge - 55+ Garden Homes Collection

    108 Carnation Way, Winchester, VA 22603
    • /47

      Est $530,067

      Not Listed For Sale

      336 Miller St, Winchester, VA 22601

      • 3 Beds
      • 2.5 Baths
      • 1,865 Sq Ft
      • Built 1941
      336 Miller St, Winchester, VA 22601

      Last Sold Summary

      • 42 Days On Market

      Last Listing Agent Julie Teets ERA Oakcrest Realty, Inc.

  • /29

    $325,000

    • 3 Beds
    • 2.5 Baths
    • 1,220 Sq Ft

    280 Sage Cir, Winchester, VA 22603

    Rare end-unit townhome situated on one of the community's desirable homesites, backing to mature trees for exceptional privacy. This spacious three-level home offers an open-concept main level featuring a bright living room, an expansive kitchen with center island, stainless steel appliances, abundant cabinetry, and a dining area with direct access to an oversized composite deck overlooking the

    Agent Photo

    Charlotte Trux

    KW Metro Center

    280 Sage Cir, Winchester, VA 22603
  • /50

    Starting at $1,722

    Total Monthly Price

    • 2 - 3 Beds

    900-1024 N Braddock St, Winchester, VA 22601

    Welcome to Fort Collier Terrace, an inviting community you'll love being part of. Our apartments in Winchester, VA, come in one, two, and three-bedroom layouts that range from 800 to 1,000 square feet. Aside from the generous living quarters, you'll find everything you need to feel right at home. Located near N Cameron Street and Martinsburg Pike, you're a stone's throw away from the top dining,

    Fort Collier Terrace

    900-1024 N Braddock St, Winchester, VA 22601
  • /84

    $618,000

    Sold Jun 08, 2026

    891 Payne Rd, Winchester, VA 22603

    • 4 Beds
    • 3.5 Baths
    • 2,849 Sq Ft
    • Built 1973

    Last Sold Summary

    • 12% Below List Price
    • $217/SF
    • 33 Days On Market

    Current Estimated Value $637,257

    Last Listing Agent Angela Duncan MarketPlace REALTY

    891 Payne Rd, Winchester, VA 22603
    • /28

      Est $285,477

      Not Listed For Sale

      946 Franklin St, Winchester, VA 22601

      • 3 Beds
      • 1 Bath
      • 1,440 Sq Ft
      • Built 1955
      946 Franklin St, Winchester, VA 22601

      Last Sold Summary

      • 34 Days On Market

      Last Listing Agent Stan Dull The Wiley Companies, Inc.

  • /2

    $300,000

    Coming Soon
    • 3 Beds
    • 1 Bath
    • 1,386 Sq Ft

    361 E Piccadilly St, Winchester, VA 22601

    In the heart of Winchester with 3 bedrooms and 1 full bath. Hardwood floors, fresh paint, kitchen with granite countertops, appliances, including full-sized washer and dryer. Lots of storage and private fenced backyard. Close to amenities. You don't want to miss this one!

    Agent Photo

    Stacy Martin

    Keller Williams Realty/Lee Beaver & Assoc.

    361 E Piccadilly St, Winchester, VA 22601
  • /10

    $1,700 Per Month

    • 1 Bed
    • 1 Bath
    • 9,518 Sq Ft
    • Condo for Rent

    44 S Loudoun St Unit 12, Winchester, VA 22601

    Charming one-bedroom apartment in the heart of historic downtown Winchester! Located right on the Walking Mall, you’ll be surrounded by local shops, restaurants, and entertainment. This inviting apartment features a spacious living room, an updated kitchen with newer cabinets and stainless steel appliances, convenient in-unit laundry, and one assigned parking space in a private lot. Enjoy

    Agent Photo

    Brock Harris

    Samson Properties

    44 S Loudoun St Unit 12, Winchester, VA 22601
  • /11

    $272,900

    Sold Nov 13, 2025

    852 Butler Ave, Winchester, VA 22601

    • 3 Beds
    • 1.5 Baths
    • 1,010 Sq Ft
    • Built 1994

    Last Sold Summary

    • $270/SF
    • 5 Days On Market

    Current Estimated Value $294,117

    Last Listing Agent LESLIE WEBB Long & Foster Real Estate, Inc.

    852 Butler Ave, Winchester, VA 22601
    • /43

      Est $355,327

      Not Listed For Sale

      205 Parkway St, Winchester, VA 22601

      • 3 Beds
      • 2.5 Baths
      • 1,008 Sq Ft
      • Built 1971
      205 Parkway St, Winchester, VA 22601

      Last Sold Summary

      • 86 Days On Market

      Last Listing Agent Agustin Martinez Spring Hill Real Estate, LLC.

Showing Results 1 - 40, Page 1 of 18

Home Price Trends

Median Sale Price
$415,000
Median Single Family Sale Price
$449,900
Median Townhouse Sale Price
$399,990
Median 2 Bedroom Sale Price
$295,500
Median 1 Bedroom Sale Price
$219,000
Average Price Per Sq Ft
$205
Number of Homes for Sale
319
Last 12 months Home Sales
1,208
Months of Supply
3.20
Median List Price
$430,000
Median Change From 1st List Price
0%
Median Home Sale Price YoY Change
3%
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