Winchester Area, VA 55+ Active Adult Retirement Communities

Nestled in the scenic Shenandoah Valley the Winchester area offers a peaceful and charming setting for those considering a 55+ active adult retirement community. Surrounded by rolling hills and historic charm, the area provides a welcoming environment for individuals in the 50-60 age range seeking a tranquil and engaging lifestyle. With its rich history and proximity to the Blue Ridge Mountains, Winchester provides a quaint backdrop for residents to explore local culture and outdoor activities.

Nestled in the scenic Shenandoah Valley the Winchester area offers a peaceful and charming setting for those considering a 55+ active adult retirement community. Surrounded by rolling hills and historic charm, the area provides a welcoming environment for individuals in the 50-60 age range seeking a tranquil and engaging lifestyle. With its rich history and proximity to the Blue Ridge Mountains, Winchester provides a quaint backdrop for residents to explore local culture and outdoor activities.

Cities in the area include Front Royal, known for its Civil War history, boasts a picturesque downtown and access to the scenic Skyline Drive. Strasburg, recognized for its well-preserved architecture, offers a glimpse into the past with its historic district. Stephens City, with its small-town charm, provides a laid-back atmosphere and convenient access to the surrounding natural beauty.

For local information and insights into the community, prospective residents can explore several helpful websites: 

Winchester Virginia Area Affordability and Cost of Living 

The Winchester area stands out as a relatively cost-effective location for retirees. The cost of housing is generally lower compared to larger metropolitan areas in the state, such as Arlington or Alexandria. While housing costs may vary within the region, the overall affordability of the area makes it an attractive option for those looking to stretch their retirement budget. Groceries and healthcare are slightly above the national average but utilities and transportation are significantly lower than the U.S. average. 

Virginia does not impose an estate or inheritance tax, providing financial flexibility for those planning their estates. Social security benefits are not taxed in the state, and while other retirement income is subject to taxation, Virginia offers a moderately favorable tax environment for retirees. For comprehensive information on state taxation, individuals can refer to the Virginia Department of Taxation.

Winchester Virginia Area Climate and Geography 

The Winchester area experiences a diverse climate with four distinct seasons, offering residents a taste of each season's beauty. Winters are characterized by cold temperatures, with average lows ranging from 20 to 25 degrees and highs between 35 and 40 degrees. The city typically receives around 20 inches of snow annually, turning Winchester into a winter wonderland. Summers bring warmer weather, with average lows of 60 to 65 degrees and highs ranging from 80 to 85 degrees. Humidity levels can be moderate, with a typical range of 50 to 60 percent. Annual rainfall averages around 39 inches. While severe weather events are relatively infrequent, residents may experience occasional thunderstorms in the summer and the possibility of winter storms during colder months.

The Winchester area is in the Shenandoah Valley, surrounded by the majestic Blue Ridge Mountains to the east and the Allegheny Mountains to the west. The Shenandoah River, known for its scenic beauty and recreational opportunities, meanders through the region. Residents can explore the Appalachian Trail, offering hiking enthusiasts stunning views of the valley. 

Recreation, Shopping, and Entertainment Near Winchester Virginia Area 

The Winchester area offers a diverse range of recreational activities, cultural events, and shopping opportunities. From lush parks and historic museums to vibrant festivals and engaging performing arts, the city provides a well-rounded experience for individuals looking for leisure and entertainment.

Golf and Racquet Sports Near Winchester VA

  • Rock Harbor Golf Course in Winchester
  • Blue Ridge Shadows Golf Club in Front Royal
  • Winchester Country Club in Winchester
  • Winchester Tennis Club in Winchester

Hiking, Biking, and Boating Near Winchester VA

  • Appalachian Trail in Winchester
  • Jim Barnett Park Trails in Winchester
  • Sky Meadows State Park in Delaplane
  • Shenandoah River State Park in Bentonville

Museums and Historical Sites Near Winchester VA

  • Museum of the Shenandoah Valley in Winchester
  • Stonewall Jackson's Headquarters in Winchester
  • Belle Grove Plantation in Middletown
  • Shenandoah Valley Civil War Museum in Winchester

Performing Arts Near Winchester VA

  • Bright Box Theater in Winchester
  • Shenandoah Conservatory in Winchester
  • Alamo Drafthouse Cinema in Winchester
  • Schultz Theatre and School of Performing Arts in New Market

Shopping Near Winchester VA

  • Old Town Winchester
  • Apple Blossom Mall in Winchester
  • Creekside Station in Winchester
  • Winchester Book Gallery in Winchester

Parks and Gardens Near Winchester VA

  • Glen Burnie Historic House and Gardens in Winchester
  • Wilkins Lake Park in Stephens City
  • Handley Regional Library Gardens in Winchester
  • Abram's Delight Gardens in Winchester

Festivals and Fairs Near Winchester VA

  • Shenandoah Apple Blossom Festival in Winchester
  • Frederick County Fair in Clear Brook
  • Hop Blossom Craft Beer Festival in Winchester
  • Shenandoah Valley Music Festival in Orkney Springs

Winchester VA Health and Wellness 

Winchester, VA, offers a robust support system for health and wellness, making it an ideal location for 55+ active adults. The area is near major medical centers, including the Winchester Medical Center, which provides comprehensive healthcare services. This medical facility is equipped with state-of-the-art technology and a range of specialized departments, ensuring that residents have access to high-quality medical care. Additionally, the Shenandoah Valley region hosts various healthcare practitioners, from specialists to general practitioners, contributing to a well-rounded healthcare network.

For those prioritizing self-care and maintaining an active lifestyle, Winchester provides numerous opportunities. Residents can engage in activities like walking and biking in the city's parks, participating in local fitness classes, and exploring the scenic outdoors for both physical and mental well-being. The Winchester area is also home to farmers markets, such as the Old Town Farmers Market which offers fresh, locally sourced produce and not only promotes a healthy diet but also provides a vibrant community space for residents to connect.

Recommended Itinerary for Visiting Winchester VA Area 55+ Communities

Exploring the Winchester area as a potential retirement destination offers a delightful mix of cultural experiences, outdoor adventures, and opportunities to envision your ideal retirement lifestyle. This two-day itinerary is designed to help you get acquainted with the area's charm, engage in recreational activities, and meet with a local 55places expert retirement community partner agent to gain valuable insights into potential retirement communities.

Day One

Morning:

  • Start your day with a leisurely breakfast at Hideway Café in Old Town Winchester, enjoying their delightful coffee and diverse menu.
  • Explore Old Town Winchester's historic district, wandering through the pedestrian-friendly streets, and perhaps visit the Old Court House Civil War Museum.

Afternoon:

Evening:

Day Two

Morning:

Afternoon:

  • Enjoy lunch at Homespun in nearby Berryville, offering a charming atmosphere and farm to table menu.
  • Meet with your local 55places expert retirement community partner agent to explore potential retirement communities tailored to your preferences.

Evening:

  • Conclude your day with dinner at Village Square Restaurant in Winchester, known for its comfort food and welcoming atmosphere.

Getting to the Winchester, VA Area

The closest major airport to Winchester is Washington Dulles International Airport (IAD), located approximately 60 miles to the southeast. This airport serves as a hub for several major airlines, including United Airlines and offers a range of domestic and international flights. Visitors can rent a car at the airport or arrange ground transportation for the journey to Winchester. 

Winchester is easily accessible by car, situated at the intersection of major highways. If driving, consider:

  • From the north: I-81 South
  • From the south: I-81 North
  • From the east or west: Route 50 or Route 7

Other transportation options include Amtrak which provides rail service to nearby cities and Greyhound which has a station in Winchester.


Communities Near Winchester Area
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10 communities near Winchester Area

0 Homes for Sale

Trilogy® at Lake Frederick

For Sale
  • High $300ks - High $900ks
  • 950 Homes (21 for sale)
  • 55+ Age Restriction
  • New And Resale Homes
  • 2006 - Present
  • 2 reviews

Cedar Meadows

For Sale
  • Mid $300ks - Low $400ks
  • 129 Homes (4 for sale)
  • 55+ Age Restriction
  • Resale Homes Only
  • 2010 - 2022
  • 1 reviews

Willow Lawn Cottages

For Sale
  • Low $300ks - Mid $300ks
  • 120 Homes (1 for sale)
  • 55+ Age Restriction
  • Resale Homes Only
  • 1999 - 2004
  • 2 reviews

Cross Creek Village

For Sale
  • Low $300ks - High $300ks
  • 90 Homes
  • 55+ Age Restriction
  • Resale Homes Only
  • 2001 - 2004
  • 1 reviews

The Village at Harvest Ridge

For Sale
  • Mid $400ks - Mid $500ks
  • 82 Homes
  • 55+ Age Restriction
  • Resale Homes Only
  • 2005 - 2016
  • 1 reviews

Woodbrook Village

For Sale
  • Mid $200ks - Mid $300ks
  • 81 Homes
  • 55+ Age Restriction
  • Resale Homes Only
  • 1999 - 2001
  • No Reviews

Heritage Highlands

For Sale
  • High $300ks - Mid $400ks
  • 80 Homes
  • 55+ Age Restriction
  • Resale Homes Only
  • 2017 - 2020
  • No Reviews

The Highlands at Blue Ridge Shadows

For Sale
  • Low $400ks - High $600ks
  • 42 Homes
  • 55+ Age Restriction
  • Resale Homes Only
  • 2017 - 2019
  • No Reviews

Cottage Glen

For Sale
  • Low $400ks - High $400ks
  • 25 Homes (2 for sale)
  • No Age Restrictions
  • New And Resale Homes
  • 2018 - Present
  • No Reviews

Abrams Chase

For Sale
  • Mid $400ks - Mid $500ks
  • 13 Homes (1 for sale)
  • 55+ Age Restriction
  • New Homes Only
  • 2020 - Present
  • No Reviews

$369,000

1056 Southern Hills Drive, Banning, CA

Meadow Ranch Community

  • 3 bed
  • |
  • 3 bath
  • |
  • 2320 SqFt
MLS CV23099287
Call Us: (800) 928-2055

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