Active-adult community discovery

55+ communities in Winchester, VA

Compare community-level facts such as age restrictions, home types, community size, HOA information, amenities, and source freshness. Communities are classified by rental or home-sale offering; individual home listings are not included.

Current inventory

8 communities

Communities with verified coordinates are ordered by distance from Winchester city center.

Willow Lawn Cottages community photo 1

55+ community

Willow Lawn Cottages

1828 Tilghman Lane, Winchester, VA, 22601

6 photos14 amenities1.6 miles from city center
Active adultHomes for sale

Housing offering

Homes for sale

Checked August 5, 2026

Abrams Chase community photo 1

55+ community

Abrams Chase

Winchester, VA

2 photos2 amenities3.1 miles from city center
Active adultHomes for sale

Housing offering

Homes for sale

Checked August 5, 2026

Woodbrook Village community photo 1

55+ community

Woodbrook Village

Winchester, VA, 20906

2 photos10 amenities3.7 miles from city center
Active adultHomes for sale

Housing offering

Homes for sale

Checked August 5, 2026

Cross Creek Village community photo 1

55+ community

Cross Creek Village

Winchester, VA, 20906

6 photos13 amenities3.8 miles from city center
Active adultHomes for sale

Housing offering

Homes for sale

Checked August 5, 2026

Cottage Glen community photo 1

55+ community

Cottage Glen

Winchester, VA

2 photos2 amenities3.9 miles from city center
Active adultHomes for sale

Housing offering

Homes for sale

Checked August 5, 2026

Willow Run community photo 1

55+ community

Willow Run

Winchester, VA

6 photos9 amenities
Active adultHomes for sale

Housing offering

Homes for sale

Checked August 5, 2026

Explore nearby

Nearby 55+ communities around Winchester, VA

55+ communities

Winchester 55+ communities statistics

A summary of currently published community profiles—not individual homes for sale.

8All communities
0For rent
8Homes for sale
0Sale and rent

Published HOA range

$85–$265/monthBased on 5 community profiles

Published purchase ranges

  • Woodbrook VillageMid $200ks - Mid $300ks
  • Cross Creek VillageLow $300ks - High $300ks
  • Willow Lawn CottagesLow $300ks - Mid $300ks
  • Abrams ChaseMid $400ks - Mid $500ks

Common home types

  • Single-Family7 of 8
  • Attached3 of 8
  • Condos1 of 8

Published age restrictions

  • 55+7 of 8
  • No Age Restrictions1 of 8

Common amenities

  • Common Grounds7 of 8
  • Walking & Biking Trails5 of 8
  • Clubhouse4 of 8
  • Multipurpose Room4 of 8
  • Retirement Community4 of 8
  • Community Center3 of 8