Winchester Homes For Sale By Owner (425 Homes)

  • Home For Sale $250,000
    • 3Bed
    • 2Baths
    • 1,842Sq ft
    130 SONGBIRD LANE , Winchester, Virginia

    Priced to sell. listed below 2019 assessed value of $271,200. no hoa. stone home with... Read More

  • Home For Sale $414,900
    • 4Bed
    • 2.5Baths
    • 2,485Sq ft
    244 PLOW RUN LANE , Winchester, Virginia

    This beautiful move-in-ready property is located in the prestigious flint ridge neighborhood. no... Read More

  • Home For Sale $389,000
    • 3Bed
    • 1.5Baths
    • 2,246Sq ft
    509 W FAIRMONT AVENUE S, Winchester, Virginia

    1910 victorian with unique architectural features full of history and less than a mile from... Read More

  • Vacant Land For Sale $249,900
    • 75,794Sq ft
    2750 FRONT ROYAL PIKE , Winchester, Virginia

    1.74 acre located on front royal pike near tasker road intersection. presently zoned ra, but... Read More

  • Home For Sale $249,900
    • 4Bed
    • 2.5Baths
    • 1,040Sq ft
    1410 S BRADDOCK STREET , Winchester, Virginia

    This braddock street home just redefined adorable. quaint space and postage stamp lot make for... Read More

  • Vacant Land For Sale $675,000
    • 87,120Sq ft
    JUBAL EARLY DRIVE , Winchester, Virginia

    Price reduced for immediate sale! development opportunity along the jubal early corridor of... Read More

  • Home For Sale $196,000
    • 3Bed
    • 2Baths
    • 1,696Sq ft
    109 PINTO TRAIL , Winchester, Virginia

    Cozy & spacious home situated on a private lot. oversized 27 x 27 garage with automatic door... Read More

  • Home For Sale $419,000
    • 4Bed
    • 4Baths
    1633 VAN COUVER STREET , Winchester, Virginia

    Welcome home to the character and charm you would expect in downtown winchester. the finishes and... Read More

  • Home For Sale $429,900
    • 5Bed
    • 3.5Baths
    • 4,766Sq ft
    214 FARMINGTON BOULEVARD , Winchester,...

    Perfect house for extended family! this home features 3 finished levels 5 bedrooms, 3.5... Read More

  • Home For Sale $349,900
    • 4Bed
    • 3Baths
    • 1,408Sq ft
    384 PERRY ROAD , Winchester, Virginia

    There are country mountain views from this mostly level 1.46 +/- level lot on perry road. trees... Read More

  • Home For Sale $400,000
    • 4Bed
    • 3.5Baths
    • 2,806Sq ft
    119 DARBY DRIVE , Winchester, Virginia

    Tons of room inside this home with 3 fully finished levels! welcoming foyer, huge home office... Read More

  • Home For Sale $239,900
    • 3Bed
    • 2.5Baths
    • 1,377Sq ft
    503 DUWAMISH TRAIL , Winchester, Virginia

    **open house sunday (3/1) 1-3pm.**welcome home! this beautiful ranch home includes 3 bedrooms,... Read More

  • Home For Sale $249,900
    • 3Bed
    • 2.5Baths
    H-29 HURON TRAIL , Winchester, Virginia

    New colonial home to be completed 120 day delivery from contract! nice private street. 3 bed, 2.5... Read More

  • Vacant Land For Sale $3,000
    • 0Sq ft
    507 GROUSE DRIVE , Winchester, Virginia

    This quarter acre lot is treed and slightly sloping

  • Home For Sale $259,500
    • 3Bed
    • 3Baths
    • 2,148Sq ft
    26 RIFLEMEN LANE , Winchester, Virginia

    Spacious 3 bed/3 bath split foyer in the city limits of winchester. enjoy the jim barnett park... Read More

  • Home For Sale $399,890
    • 3Bed
    • 2Baths
    • 1,992Sq ft
    161 MORNING GLORY DRIVE , Winchester,...

    A beautifully maintained 2-year-old home is ready for a new owner. one floor living has 3... Read More

  • Home For Sale $359,900
    • 3Bed
    • 3Baths
    • 3,314Sq ft
    101 MCCLURE WAY , Winchester, Virginia

    Soundly built rancher in outstanding location. not only are you in a cul-de-sac, you get a large,... Read More

  • Home For Sale $218,500
    • 3Bed
    • 1Baths
    • 1,487Sq ft
    436 N LOUDOUN STREET , Winchester, Virginia

    Come in & enjoy yesteryear with a tad touch of modern. fresh paint, new carpet, and the floors... Read More

  • Home For Sale $239,000
    • 3Bed
    • 1Baths
    • 1,725Sq ft
    119 E CLIFFORD STREET , Winchester, Virginia

    Located just a couple of blocks from the heart of old town winchester, this great house built in... Read More

  • Home For Sale $267,900
    • 3Bed
    • 2.5Baths
    • 1,455Sq ft
    106 MESQUITE COURT , Winchester, Virginia

    House features 3 bed 2.5 baths with central air/heat situated on a cul de sac in move in ready... Read More

Winchester - Statistics and Home Trends

Actives Activity Chart


$ 534,964




$ 3,298

Average Price
Land in WINCHESTER (191) $ 357,810


$ 509,656




$ N/A

Learn More About Winchester, Virginia

Currently there are 231 homes for sale and 191 vacant land for sale in Winchester

Background on Winchester, Virginia
Winchester is an Independent city that is in the Northwestern portion of the Commonwealth of Virginia. Winchester is the county seat of Frederick County. Winchester is also the principal city of the Winchester, Virginia – West Virginia Metro Statistical Area. The population here as of 2017 was just under 28,000, up from just over 26,000 in 2010. According to the United States Census Bureau, Winchester is approximately 9 square miles in size. The climate here is characterized as humid subtropical. The summers here tend to be warm and humid, hence the name “humid subtropical.” The winters here tend to be very cold. The coldest part of the year here is from the very end of November until the beginning of March when the daily average high is just 50 degrees. The average low for this time of year is just 26 degrees. So it does tend to get cold here but the summer months definitely make up for that. The hottest part of the year here is from the tail end of May until mid September. During this time the daily average high is just around 80 degrees. The average low for this time time is a very comfortable 67 degrees. As previously mentioned the weather here varies from season to season but it rarely goes below 12 degrees here during the winter or about 95 during the summer.

Apple Blossom
Here in Winchester you will find something called the “Shenandoah Apple Blossom Festival” which is a festival that has been in existence since the year 1924. This event typically takes place during the first weekend of May. This festival is truly incredible with all of its activities. There is a firework show, carnival, parades and a coronation where the Apple Blossom Queen is crowned. This event sounds like something right out of a Hallmark movie. This festival is such a big deal here in Winchester that many businesses and schools close on the Friday before the event to prepare for it. If you live in the Winchester area, this event is something you need to experience at least once!

Winchester and the Civil War
Winchester was the site of several battles that took place during the American Civil War. So that means that Winchester is mentioned in history textbooks all over the United States. Crazy to think about, right? Here are the battles that took place here in Winchester between the years 1862 through 1864. “The First Battle of Kernstown” took place on March 23rd, 1862. “The First Battle of Winchester” took place on May 25th, 1862. “The Second Battle of Winchester” took place on June 13th through the 15th of 1863. “The Second Battle of Kernstown” took place on July 24th, 1864 and “The Third Battle of Winchester” took place here on September 19th, 1864. There are also several other battles that took place in nearby areas between the months of July and October of 1864.

Subdivisions Here in Winchester
There are many subdivisions here for you to pick from when moving or relocating to Winchester. If you are looking for an adult community (55 and over) look no further than “Cottage Glen.” This new community offers homes with open floor plans and high-end finishes like granite countertops and stainless steel appliances. If you are looking for a more established neighborhood there is “Fieldstone.” This subdivision offers single family homes as well as townhomes. The townhomes here are quite large and are just as big as some of the single family homes here with three bedrooms and three and a half bathrooms. These are just a couple of the amazing subdivisions available here in Winchester for you to check out.

Major Highways and Transportation in Winchester
Here in Winchester there are a few roads that serve the area. There is U.S Route 11, U.S Route 50, U.S Route 17 and U.S Route 522. If you prefer to not drive, there is “Winchester Transit” which runs six days a week. It makes stops at Valley Ave, Apple Blossom Mall, Berryville Ave, Northside – Salvation Army, South Loudoun, Trolley, Amherst Street as well as Northside – Westminister Canterbury. Since Winchester is relatively small having a transit system that operates six days a week really helps people get around who do not have access to a car.

Winchester is a wonder, small city that has so much to offer potential homebuyers. There is an abundant amount of real estate available here as well as a rich history that can be found in any middle or high school textbook. Make sure to check out Winchester when thinking of moving to Virginia! offers For Sale By Owner listing services throughout the country. By posting home with ByOwner your property will get the same exposure you’d receive from a traditional real estate company. Our Winchester, Virginia Flat Fee MLS listing Service saves you from paying the traditional 6% commission charged by most real estate offices, but gives you the same worldwide exposure.

Your home will be found on the local MLS, plus all the major search engines and popular real estate portal sites, including: Trulia, Zillow,, MSN, AOL, Bing, Yahoo, and of course Google. Additionally when your home gets added to the MLS, your FSBO listing will listed alongside of the homes listed by ReMax, C-21, Coldwell Banker, ERA, Redfin, Movoto, Keller Williams and all the other nationwide brokerage sites. These sites often display “all” of the MLS postings, not just their own, which means your home will be on these sites also.

The average seller who uses our Flat Rate MLS Listing, will save over $15,000. We give you the tools and exposure you need as a ForSaleByOwner to compete with every other listing in the MLS. But you are in control of the savings and the fees you pay.

Currently Winchester has 425 properties on the market for sale. The inventory was last updated 02/22/2020. Of these properties, 231 single family homes are for sale by their owners in Winchester, and 0 condos are for sale by their owners in Winchester. The average price of the single family homes for sale in Winchester, is $303,630, the average condo price in Winchester, is $534,964. The average price per square foot of the active inventory is $86. This is based the living area square footage.

Over the last year, there have been 9,956 of properties sold in Winchester. Of these properties, 9,167 single family homes have sold by their owners in Winchester, and 0 condos have sold by their owners in Winchester. The average sales price of the single family homes sold in Winchester, is $244,671. Single family homes have been selling for 148 per square foot of living area. The average sales price of the condos for sale in Winchester, is $280,827. Condos have been selling for 142 per square foot of living area.

The most active subdivisions with listings for sale in Winchester, are: Shawneeland (19 For Sale), None Available (15 For Sale), Wilde Acres (15 For Sale), Freedom Manor (13 For Sale), Roscommon (8 For Sale), Stoneymeade (7 For Sale), Winchester City (7 For Sale), The Oaks At Braddock Crossing (7 For Sale), Sovereign Village (6 For Sale), Wilde Acres (5 For Sale)

If you are thinking of selling your Winchester home, try our flat fee listing service, Our list fees start at $449, and may save you $15,000 in real estate commissions. Click here to start saving.

Disclaimer: Listing broker has attempted to offer accurate data, but buyers/lessees are advised to confirm all information IDX information is provided exclusively for consumers' personal, non-commercial use that it may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing, and that data is deemed reliable but is not guaranteed accurate by the MLS. The MLS may, at its discretion, require use of other disclaimers as necessary to protect Participants and/or the MLS from liability.
This data up-to-date as of 02/22/2020