Winchester Homes For Sale By Owner (588 Homes)

  • Home For Sale $189,000
    • 3Bed
    • 1Baths
    • 1,452Sq ft
    336 OPEQUON AVENUE , Winchester, Virginia

    Fantastic one level living with open concept. large family room off the back of the home flows... Read More

  • Home For Sale $192,000
    • 3Bed
    • 1Baths
    • 1,033Sq ft
    620 BUTLER AVENUE , Winchester, Virginia

    Three bedroom one full bath ranch home. fenced rear yard, newer roof, close to shopping,... Read More

  • Home For Sale $2,500,000
    • 2Bed
    • 2Baths
    690 SHADY ELM ROAD , Winchester, Virginia

    Don't miss out on this extremely rare opportunity for your family or business to own this amazing... Read More

  • Home For Sale $319,900
    • 3Bed
    • 3.5Baths
    • 2,250Sq ft
    115 BISCANE COURT , Winchester, Virginia

    Perfectly appointed end unit is truly better than new! completely move in ready, the current... Read More

  • Home For Sale $329,900
    • 3Bed
    • 1.5Baths
    • 1,726Sq ft
    306 W WHITLOCK AVENUE , Winchester, Virginia

    Anne of green gables style of home in winchester with a modern interior flair! stunning kitchen... Read More

  • Home For Sale $269,900
    • 2Bed
    • 2Baths
    • 1,647Sq ft
    1806 TILGHMAN LANE , Winchester, Virginia

    You won't find a home that has been so well taken care of! adult community 55+, one floor living,... Read More

  • Home For Sale $189,900
    • 3Bed
    • 2Baths
    • 1,458Sq ft
    312 RACCOON DRIVE , Winchester, Virginia

    Quaint rancher with lots to offer! this spacious 3 bed 2 bath home has been well cared for. new... Read More

  • No Image
    Home For Sale $169,900
    • 5Bed
    • 2.5Baths
    • 2,198Sq ft
    368 NATIONAL AVENUE , Winchester, Virginia

    Large home has some interesting features. recently painted throughout.

  • Home For Sale $225,000
    • 2Bed
    • 2Baths
    • 1,161Sq ft
    1815 S LOUDOUN STREET , Winchester, Virginia

    Location for business or residential. massive garage on busy intersection on south part of town.... Read More

  • Home For Sale $279,900
    • 4Bed
    • 3Baths
    173 MASON STREET , Winchester, Virginia

    Brand new split foyer home conveniently located east of winchester off senseny road. 4 bedrooms... Read More

  • Home For Sale $399,999
    • 2Bed
    • 2Baths
    • 2,001Sq ft
    420 CANYON ROAD , Winchester, Virginia

    Turn key, new home in meticulous condition! master on the main! all one level living in an... Read More

  • Home For Sale $315,000
    • 4Bed
    • 2.5Baths
    • 2,344Sq ft
    202 SENTINEL DRIVE , Winchester, Virginia

    Lovely colonial in sought after star fort. situated just outside the city limits you're still... Read More

  • Home For Sale $176,500
    • 2Bed
    • 2.5Baths
    • 1,448Sq ft
    118 TUDOR DRIVE , Winchester, Virginia

    Rare opportunity to own in this conveniently located neighborhood close to downtown winchester,... Read More

  • Home For Sale $194,900
    • 3Bed
    • 1.5Baths
    • 1,196Sq ft
    213 WEST STREET , Winchester, Virginia

    A finer location in winchester city would be very hard to find! totally remodeled & shines like... Read More

  • Home For Sale $519,999
    • 7Bed
    • 5Baths
    2703 CASSIDY COURT , Winchester, Virginia

    You'll love this stunning 3-story, 7 bedroom home located 2 blocks from frederick douglass... Read More

  • Home For Sale $194,500
    • 2Bed
    • 2.5Baths
    • 1,534Sq ft
    509 BRAEBURN DRIVE , Winchester, Virginia

    Check out this beautiful townhouse in huntington meadows. great commuter location and close to... Read More

  • Home For Sale $228,900
    • 3Bed
    • 2.5Baths
    • 1,960Sq ft
    214 MONTICELLO SQUARE , Winchester, Virginia

    If you are looking for an updated townhouse on the east side of town in pristine condition, look... Read More

  • Home For Sale $889,000
    • 5Bed
    • 5.5Baths
    • 6,603Sq ft
    613 STONYMEADE DRIVE , Winchester, Virginia

    Turn key ready with fresh paint and refinished floors. grand home includes 1st floor suite.... Read More

  • Home For Sale $199,900
    • 3Bed
    • 2Baths
    594 MAHLON DRIVE , Winchester, Virginia

    Remodeled home on 5 acres 10 minutes from the hospital. this home boasts ceramic tile floors in... Read More

  • Home For Sale $400,000
    • 4Bed
    • 3Baths
    • 2,552Sq ft
    489 BROOKNEIL DRIVE , Winchester, Virginia

    Beautiful colonial on 5 peaceful acres in frederick county. enjoy the privacy and watch the deer... Read More

Winchester - Statistics and Home Trends

Actives Activity Chart


$ 321,624




$ 238

Average Price
Land in WINCHESTER (252) $ 341,322


$ 324,438




$ N/A

Learn More About Winchester, Virginia

Currently there are 332 homes for sale and 252 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 588 properties on the market for sale. The inventory was last updated 08/22/2019. Of these properties, 332 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 $326,298, the average condo price in Winchester, is $321,624. The average price per square foot of the active inventory is $150. This is based the living area square footage.

Over the last year, there have been 10,332 of properties sold in Winchester. Of these properties, 9,572 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 $239,494. Single family homes have been selling for 145 per square foot of living area. The average sales price of the condos for sale in Winchester, is $277,488. Condos have been selling for 138 per square foot of living area.

The most active subdivisions with listings for sale in Winchester, are: Shawneeland (29 For Sale), Wilde Acres (23 For Sale), None Available (12 For Sale), Wilde Acres (11 For Sale), Sovereign Village (10 For Sale), The Oaks At Braddock Crossing (8 For Sale), Stoneymeade (7 For Sale), Flint Ridge (7 For Sale), Abrams Pointe (7 For Sale), Fieldstone (6 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 08/22/2019