Winchester, VA Real Estate & Homes For Sale

237 homes

  • 225 Susquehanna Trl, Winchester, VA 22602
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    NEWCOMING SOON 4/50.5 ACRES
    $284,900
    3bd
    2ba
    1,528 sqft (on 0.50 acres)
    225 Susquehanna Trl,
    Winchester, VA 22602
    Blue Valley Real Estate
  • 521 Monticello St, Winchester, VA 22601
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    NEWCOMING SOON 4/12
    Berkshire Hathaway HomeServices PenFed Realty
  • 147 Brookland Ct #6, Winchester, VA 22602
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    NEWCOMING SOON 3/29
    Keller Williams Realty/Lee Beaver & Assoc.
  • 106 Marlise Ln, Winchester, VA 22602
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    0.28 ACRES
    $630,000
    4bd
    3ba
    4,570 sqft (on 0.28 acres)
    106 Marlise Ln,
    Winchester, VA 22602
    Samson Properties
  • Lot-31A Fishel Rd, Winchester, VA 22602
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    NEW - 57 MIN AGO22.48 ACRES
    ICON Real Estate, LLC
  • 412 Spring Valley Dr, Winchester, VA 22603
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    NEW - 1 DAY AGO3.24 ACRES
    $429,900
    4bd
    2ba
    2,740 sqft (on 3.24 acres)
    412 Spring Valley Dr,
    Winchester, VA 22603
    Colony Realty
  • 111 Emily Ln, Winchester, VA 22602
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    NEW - 2 DAYS AGO
    $249,900
    3bd
    2ba
    1,320 sqft
    111 Emily Ln,
    Winchester, VA 22602
    RE/MAX Distinctive Real Estate
  • 117 Woodys Pl, Winchester, VA 22602
    NEWCOMING SOON 3/300.28 ACRES
    $429,900
    5bd
    3ba
    2,398 sqft (on 0.28 acres)
    117 Woodys Pl,
    Winchester, VA 22602
    Realty ONE Group Old Towne
  • 120 Meeting House Dr, Winchester, VA 22602
    NEWCOMING SOON 4/13 ACRES
    $635,000
    4bd
    3ba
    3,762 sqft (on 3 acres)
    120 Meeting House Dr,
    Winchester, VA 22602
    Coldwell Banker Premier
  • 2081 Cidermill Ln, Winchester, VA 22601
    NEW - 1 DAY AGO
    ERA Oakcrest Realty, Inc.
  • 2428 Massanutten Ter, Winchester, VA 22601
    0.46 ACRES
    $319,900
    3bd
    1ba
    1,676 sqft (on 0.46 acres)
    2428 Massanutten Ter,
    Winchester, VA 22601
    RE/MAX Roots
  • 204 Hawk Trl, Winchester, VA 22602
    0.46 ACRES
    $300,000
    3bd
    2ba
    1,288 sqft (on 0.46 acres)
    204 Hawk Trl,
    Winchester, VA 22602
    RE/MAX Roots
  • 118 Meadow Way, Winchester, VA 22602
    NEW - 15 HRS AGONEW CONSTRUCTION0.7 ACRES
    $439,900
    4bd
    3ba
    2,351 sqft (on 0.70 acres)
    118 Meadow Way,
    Winchester, VA 22602
    CENTURY 21 New Millennium
  • 109 Stribling Way, Winchester, VA 22602
    NEWCOMING SOON 4/5
    MAP Property Solutions, LLC.
  • 308 Colin Ct, Winchester, VA 22601
    $525,000
    4bd
    3ba
    2,953 sqft
    308 Colin Ct,
    Winchester, VA 22601
    Funkhouser Real Estate Group
  • 1742 Back Mountain Rd, Winchester, VA 22602
    NEW - 1 DAY AGOFORECLOSURE6.75 ACRES
    $380,000
    3bd
    2ba
    1,527 sqft (on 6.75 acres)
    1742 Back Mountain Rd,
    Winchester, VA 22602
    ERA Oakcrest Realty, Inc.
  • 138 Merlot Dr, Stephenson, VA 22656
    NEW - 1 DAY AGO0.35 ACRES
    $550,000
    3bd
    3ba
    2,441 sqft (on 0.35 acres)
    138 Merlot Dr,
    Stephenson, VA 22656
    Long & Foster Real Estate, Inc.
  • 292 Marple Rd, Winchester, VA 22603
    OPEN SAT, 10-1PMCOMING SOON 3/303.07 ACRES
    $390,000
    3bd
    2ba
    1,633 sqft (on 3.07 acres)
    292 Marple Rd,
    Winchester, VA 22603
    Atoka Properties
  • 504 Marion St, Winchester, VA 22601
    NEWCOMING SOON 4/51.03 ACRES
    $799,900
    5bd
    5ba
    5,453 sqft (on 1.03 acres)
    504 Marion St,
    Winchester, VA 22601
    ERA Oakcrest Realty, Inc.
  • 133 Fortress Dr, Winchester, VA 22603
    0.39 ACRES
    $539,000
    5bd
    4ba
    3,460 sqft (on 0.39 acres)
    133 Fortress Dr,
    Winchester, VA 22603
    Coldwell Banker Premier
  • 141 Rappahannock Trl, Winchester, VA 22602
    0.66 ACRES
    $245,000
    2bd
    1ba
    660 sqft (on 0.66 acres)
    141 Rappahannock Trl,
    Winchester, VA 22602
    Pearson Smith Realty, LLC
  • 255 White Rd, Winchester, VA 22602
    30 ACRES
    $1,499,000
    6bd
    5ba
    5,900 sqft (on 30 acres)
    255 White Rd,
    Winchester, VA 22602
    Nova Home Hunters Realty
  • Lot 11 Buttonwood Ln, Winchester, VA 22602
    3.29 ACRES
    Long & Foster Real Estate, Inc.
  • Amherst Plan in Abrams Pointe, Winchester, VA 22602
    NEW CONSTRUCTION
  • 151 Brookland Ter #6, Winchester, VA 22602
    RE/MAX Distinctive Real Estate, Inc.
  • 312 Wood Ave, Winchester, VA 22601
    0.34 ACRES
    $475,000
    3bd
    4ba
    3,069 sqft (on 0.34 acres)
    312 Wood Ave,
    Winchester, VA 22601
    Samson Properties
  • 2316 Tower Ave, Winchester, VA 22601
    COMING SOON 4/40.26 ACRES
    $430,000
    4bd
    3ba
    2,095 sqft (on 0.26 acres)
    2316 Tower Ave,
    Winchester, VA 22601
    Realty ONE Group Old Towne
  • 152 Denny Ln, Winchester, VA 22603
    COMING SOON 3/290.47 ACRES
    $310,000
    2bd
    1ba
    915 sqft (on 0.47 acres)
    152 Denny Ln,
    Winchester, VA 22603
    Coldwell Banker Premier
  • 139 Country Park Dr, Winchester, VA 22602
    0.25 ACRES
    $270,000
    3bd
    1ba
    960 sqft (on 0.25 acres)
    139 Country Park Dr,
    Winchester, VA 22602
    Coldwell Banker Premier
  • 339 Lanny Dr, Winchester, VA 22601
    0.4 ACRES
    $419,999
    3bd
    3ba
    2,716 sqft (on 0.40 acres)
    339 Lanny Dr,
    Winchester, VA 22601
    Colony Realty
  • 541 Gray Ave, Winchester, VA 22601
    $180,000
    2bd
    2ba
    1,024 sqft
    541 Gray Ave,
    Winchester, VA 22601
    Century 21 Redwood Realty
  • 112 W  Pall Mall St, Winchester, VA 22601
    OPEN SAT, 12-2PM
    MarketPlace REALTY
  • 101 Sovereign Ct, Winchester, VA 22602
    COMING SOON 4/5
    Metro House
  • 307 Fawn Dr, Winchester, VA 22602
    0.76 ACRES
    $345,900
    3bd
    2ba
    1,620 sqft (on 0.76 acres)
    307 Fawn Dr,
    Winchester, VA 22602
    Pearson Smith Realty, LLC
  • 168 Amoco Ln, Winchester, VA 22603
    COMING SOON 4/40.54 ACRES
    $275,000
    2bd
    2ba
    1,360 sqft (on 0.54 acres)
    168 Amoco Ln,
    Winchester, VA 22603
    RE/MAX Roots
  • 308 Miller St, Winchester, VA 22601
    OPEN SAT, 11-2PMCOMING SOON 3/29
    $375,000
    3bd
    2ba
    1,815 sqft
    308 Miller St,
    Winchester, VA 22601
    Keller Williams Realty
  • 1815 Melvor Ln, Winchester, VA 22601
    $365,000
    2bd
    2ba
    1,419 sqft
    1815 Melvor Ln,
    Winchester, VA 22601
    RE/MAX Roots
  • 100 Lenore Ln, Winchester, VA 22602
    NEW CONSTRUCTION
    $544,568
    3bd
    2ba
    1,326 sqft
    100 Lenore Ln,
    Winchester, VA 22602
    LPT Realty, LLC

Winchester, VA Real Estate Trends

Learn about the Winchester, VA housing market through trends and averages.

Affordability of Living in Winchester, VA

The median home value is $361,749
MonthMedian home value
March 2023$348k
April 2023$349k
May 2023$351k
June 2023$354k
July 2023$356k
August 2023$357k
September 2023$359k
October 2023$360k
November 2023$361k
December 2023$361k
January 2024$361k
February 2024$362k
View as a graph
Trends and affordability stats are provided by third party data sources.

Average Home Value in Winchester, VA, by Home Size

Currently, there are 41 new listings and 237 homes for sale in Winchester.
Home SizeHome Value*
1 bedroom (1 home)$219,755
2 bedrooms (25 homes)$248,587
3 bedrooms (68 homes)$335,115
4 bedrooms (64 homes)$487,018
*Home value over the past month

What Locals Say about Winchester

  • Kelrendon83
    "Great community for live , safe and good for raise kids and the family can have a good place to visit , some good festivals "
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  • 7seymours
    "Lived here for 22 yrs. Beautiful, spacious, quiet and good neighbors! We feel safe here with a lot of privacy. Neighbors look out for each other & help each other "
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  • Gfbzc98z9n
    "It is Quiet and safe while still being just a short trip to the big city. Beautiful downtown walking mall. Great outdoors all around in the Blue Ridge Mountains."
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  • 7seymours
    "Apple Blossom Festival which is held annually with parades, celebrities, dances, music & arts & crafts. A beautiful weekend during Apple Blossom time with over 250,000 visitors attending this special event in the Shenandoah Valley "
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  • Trulia User
    "Everyone I have ran into has been nice. Definitely a very family friendly neighborhood. Feels very cozy "
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  • Morganva
    "Dog friendly, plenty of green space, and lots of dog bag dispensers for cleaning up after the pooch. "
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  • Bridgetdefoe
    "It’s easy to get around Winchester. Roads are well maintained. Traffic is minimal. You can get about anywhere in Winchester is less than 20 minutes. Rt 7 has become busy as an exception due to people commuting to Loudoun County "
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  • Isabelle M.
    "Is a nice ride and no traffic in the area, many shopping centers, great area to visit, one of the great hospital in the nation."
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  • Alliav11%40gmail.com
    "A lot of people have dogs here and they are always waking them. There are a lot of stray cats so if dogs don’t like them beware"
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  • Gina A.
    "It's just a nice neighborhood to walk. People are always waving and stopping to chat. And they clean up after their dogs"
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  • Cooda K.
    "It’s a lot It’s a lot I can say I honestly feel like it’s a beautiful place I mean the cabs suck But other than that I feel like it’s a nice expensive place to live 😁 "
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  • Topeye
    "Very good schools, low crime rate, good jobs. Civic pride. Great long-running annual community festival. Many churches and civic organizations are active. Historic preservation. "
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  • Rob R.
    "My commute to downtown is usually fairly quick, not too much traffic. Public transportation is not very popular."
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  • Nickruiz270
    "The commute into Winchester is fairly light but around 5pm it’s when it gets heavy. I would try to avoid all small roads as much as possible and use the highway as much as possible. "
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  • Careliza81
    "We are just walking distance to the walking mall which has tons of activities throughout the year. There are festivals for most major holidays and apple blossom. "
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  • Nick A.
    "There is a great community of people here and it’s very welcoming. Living here is home for me and I would recommend moving here if you want to be close to major metropolis and still be near countryside"
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  • Nellycordon
    "The neighborhood is great plus shopping center are very close. Also. Friendly people. So I feel safe "
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  • Chels J.
    "Great safe place for kids no strange people more of a older group of people live here. It’s out of the way of the city but seconds from town"
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  • Brock M.
    "Great area to live and raise a family. Good earnings potential. Great university. Awesome private and public school system."
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  • Coach_ramos
    "You must drive or carpool. There is a local bus/trolley, but only locally within the city. No rail or subway."
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  • Leslie H.
    "I commute to Northern Va and Loudoun Co. it’s more brutal each year, especially the return commute. "
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  • Brad M.
    "Old town feel and downtown is lively. We enjoy being able to walk in a safe environment and walk to restaurants and shops. A great place to live in a historic town. "
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  • Sarai D.
    "old town feeling with city vibes, great spots and food. historic and pleasurable to look at. community is a big deal in this town and very generous people as a whole. "
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  • Yesenia R.
    "The community center provides events for all. From all the holidays to special events for fundraisers along with also assisting the community with school supplies. There’s also playgrounds and pools."
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  • Danielle M.
    "There are no community events in my neighborhood...everyone mostly keeps to themselves with the exception of those of us who have lived here for over thirty years. "
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  • Yesenia R.
    "It’s a shared community and everyone takes care of it. The office is good about maintaining the facilities clean and safe. Maintenance is usually quick with repairs."
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  • Erin G. .
    "Nothing special, just a nice neighborhood. Nice and quiet. Friendly folks. Safe for kids to play. Convenient to shopping."
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  • Samantha F.
    "There is a large park just a few blocks away. Enough room to let a we trained dog off the leash. Walking distance to downtown dog friendly restaurants. "
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  • Topeye
    "The public library across the street and the pedestrian mall 2 blocks away frequently hold community events."
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  • Ritterma1026
    "Winchester is a beautiful historic city that continues to gentrify. beautiful old historic properties have become modern Oasis and close to northern Virginia amenities. lots of small businesses in boutique shops. farm to table restaurants and outstanding dining with a gorgeous pedestrian mall in the historic district. outstanding public schools in Frederick County and the city of Winchester. additionally, excellent public amenities like transit and libraries! wineries and breweries"
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  • Masonh885
    "OK I have been in this area where you don't have or see tick or treating. for hollween I agree to all the way "
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  • Juanita e
    "dog owners would love this area great place to live great county sitting quite schools stores dr.s hospital close malls shopping casinos horse racing car raises movies drive in s close tons restaurants parks city county parks swimming snow skiing within hour"
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  • Andrea
    "Nothing. Nice area not much for kid s to do no playgrounds or nearby parks but nice for adults "
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  • Destiny W.
    "There's a big Park perfect for taking your dog. Plus you'll see all kinds of dogs being walked downtown on the waking mall. A few businesses even put a water bowl out for the dogs that walk by"
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  • Debra T.
    "There is a bus stop only a few minutes from my front door. I know you can take the bus down town! I am not sure about long distance travel!"
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  • Jeanna C.
    "My commute is very quick! I live close to pretty much everywhere that I need to go regularly. I can even walk to convenience stores if I need to."
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  • Island4tj
    "The city is relatively safe and the schools are very good. Nice, clean town to live in that’s family-oriented. "
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  • Ruizy8329
    "The neighborhood provides many sidewalks and grassy areas for peaceful and well lit dog walking. People in the area mostly have pets and those who don’t are usually very good about it. "
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  • Ahammar051416
    "older kids play rough sometimes. some cars that drive through not very attentive to children...an interesting area for sure. "
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  • Britni P.
    "They need more room to run around. Like a fenced in yard and a dog park. Anywhere for a dog to be a dog"
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