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Winchester, VA 55+ active adult communities & homes for sale
Living in Winchester
55+ active adults will enjoy Winchester’s abundant natural recreation areas and its many historical sites. Financially Winchester is appealing to seniors looking for…
55+ active adults will enjoy Winchester’s abundant natural recreation areas and its many historical sites. Financially Winchester is appealing to seniors looking for retirement communities due to its low sales tax rate and because social security income is not taxed.
Climate & Geography
Winchester is in a humid subtropical zone with humid warm summers and cold winters. The area sees about 30 inches of rain per year, much of it falling during the month of May. Winter temperatures average from 23° to 40° and snow accumulations average over 17 inches. Summer in Winchester is hot and humid with summer temperatures averaging 64° to 86° and 79% humidity.
Located 10 miles south of the Virginia/West Virginia state line Winchester is in the Shenandoah Valley nestled between the Blue Ridge and Allegheny Mountains.
Recreation, Culture & Entertainment
There are a variety of leisure options for active adults in the Winchester area, including:
Historical sites and museums
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- Museum of the Shenandoah Valley
- Stonewall Jackson’s Headquarters
- Shenandoah Valley Civil War Museum
- Kernstown Battlefield and Pritchard House
- Washington’s Office Museum
- Old Town Winchester
- Stonewall Confederate Cemetery
Outdoor activities
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- Rocking S Ranch horseback riding
- Abrams Creek Wetlands Preserve
- Shawnee Springs Preserve
- The Wagon Wheel Ranch horseback riding
- Magic Mountain Farms horseback riding
- Rock Harbor Golf Course
Other activities
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- Briede Family Vineyards
- James Charles Winery & Vineyard
- Ravenwood Faire
Cost of Living & Taxes
Virginia collects a personal income tax, sales tax, and food tax. The property tax is set and collected at a local level, which varies throughout Virginia. Social Security benefits are not taxed, and real estate is assessed at 100 percent of fair market value. The combined state, county and city taxes equals to a 5.3% sales tax on purchases in Winchester.
Health Care
Winchester Medical Center is the only hospital that is close to Winchester, the hospital has 495 beds and is a Level II trauma center. Warren Memorial Hospital and Jefferson Medical Center in Ranson, WV are both about 20 miles from Winchester. Warren Memorial Hospital has earned a grade A from the Leapfrog Group.
Frequently Asked Questions
Of the 8 55+ communities in Winchester, 8 are for sale and none are rentals. By size, there are no large communities, no medium communities, and 7 small communities with less than 500 homes.
The smallest 55+ communities in Winchester has 13 homes, the largest has 300 homes, and the average communities consists of 101 homes.
Yes, there are new 55+ homes available in Winchester. The most recent communities started in Winchester include Winchester Landing, Abrams Chase, Cottage Glen. There are also 3 communities in Winchester that offer new construction homes, including Cottage Glen, Willow Run, Abrams Chase.
Yes, there are gated 55+ communities in Winchester. Approximately 25.0% of 55+ communities in the area are gated. For instance, Cottage Glen is a gated communities with 25 homes, and Willow Run is another gated communities with 300 homes.
On average, listings in 55+ communities in Winchester stay on the market for around 503 days. The average price of homes for sale in these communities is approximately $463,934, though prices can range widely based on the size, location, and amenities of the communities. For example, homes in Willow Run average around $623,623, while homes in Cross Creek Village average around $427,167.
10 communities near Winchester
33 homes near Winchester
Relevance
3 beds
|3 baths
|3,203 sq ft
3 beds
|3 baths
|3,203 sq ft
2 beds
|2 baths
|1,642 sq ft
3 beds
|3 baths
|1,752 sq ft
4 beds
|3 baths
|4,385 sq ft
3 beds
|3 baths
|2,264 sq ft
3 beds
|3 baths
|1,752 sq ft
3 beds
|3 baths
|2,264 sq ft
2 beds
|3 baths
|2,679 sq ft
2 beds
|2 baths
|2,205 sq ft
2 beds
|2 baths
|1,564 sq ft
3 beds
|3 baths
|1,893 sq ft
3 beds
|3 baths
|2,264 sq ft
3 beds
|3 baths
|1,893 sq ft
3 beds
|3 baths
|1,752 sq ft
Frequently Asked Questions
Of the 8 55+ communities in Winchester, 8 are for sale and none are rentals. By size, there are no large communities, no medium communities, and 7 small communities with less than 500 homes.
The smallest 55+ communities in Winchester has 13 homes, the largest has 300 homes, and the average communities consists of 101 homes.
Yes, there are new 55+ homes available in Winchester. The most recent communities started in Winchester include Winchester Landing, Abrams Chase, Cottage Glen. There are also 3 communities in Winchester that offer new construction homes, including Cottage Glen, Willow Run, Abrams Chase.
Yes, there are gated 55+ communities in Winchester. Approximately 25.0% of 55+ communities in the area are gated. For instance, Cottage Glen is a gated communities with 25 homes, and Willow Run is another gated communities with 300 homes.
On average, listings in 55+ communities in Winchester stay on the market for around 503 days. The average price of homes for sale in these communities is approximately $463,934, though prices can range widely based on the size, location, and amenities of the communities. For example, homes in Willow Run average around $623,623, while homes in Cross Creek Village average around $427,167.
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REIN updates its listings on a daily basis. Data last updated: Nov 11, 2026.
This application does not include information on all of the properties available for sale at this time.
