Winchester Area, VA 55+ active adult communities & homes for sale - Page 2

229 homes near Winchester Area

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5 rating (2 reviews)

Trilogy® at Lake Frederic...

$400ks - $900ks

Trilogy® at Lake Frederic..., Lake Frederick, VA

New and Resale | 55+ age-restricted | Built 2006 - present | 950 homes

5 rating (31 reviews)

Lansdowne Woods of Virgin...

$200ks - $500ks

Lansdowne Woods of Virgin..., Lansdowne, VA

Resale Only | 55+ age-restricted | Built 1998 - 2017 | 1,200 homes

The Flats at Heathcote Vi...

$300ks - $500ks

The Flats at Heathcote Vi..., Haymarket, VA

New Construction | 55+ age-restricted | Built 2026 - present | 500 homes

5 rating (3 reviews)

Heritage Hunt

$400ks - $600ks

Heritage Hunt, Gainesville, VA

Resale Only | 55+ age-restricted | Built 1998 - 2009 | 1,863 homes

2 rating (1 reviews)

Birchwood at Brambleton

$400ks - $1Ms

Birchwood at Brambleton, Ashburn, VA

New and Resale | 55+ age-restricted | Built 2016 - present | 1,502 homes

Want to learn more about 55+ communities in Winchester Area? 55places can help!

Questions? Call us: (540) 452-4199

The Woodlands of Urbana

$500ks - $700ks

The Woodlands of Urbana, Urbana, MD

Resale Only | 55+ age-restricted | Built 2019 - 2025 | 565 homes

Emerald Pointe

$300ks - $500ks

Emerald Pointe, Hagerstown, MD

New and Resale | 55+ age-restricted | Built 2008 - present | 250 homes

5 rating (1 reviews)

Regency at Dominion Valle...

$300ks - $1Ms

Regency at Dominion Valle..., Haymarket, VA

Resale Only | 55+ age-restricted | Built 2001 - 2017 | 855 homes

Willow Run

$500ks - $600ks

Willow Run, Winchester, VA

New Construction | 55+ age-restricted | 300 homes

The Village at Freedom Hi...

$300ks

The Village at Freedom Hi..., Hagerstown, MD

New and Resale | 55+ age-restricted | Built 2007 - present | 66 homes

Download the Ultimate 55+ Homebuying Guide Whether you’re searching for a 55+ community, downsizing, or exploring other housing options, our free-to-download guide will assist you in finding the ideal home for your needs.

Bloomfields 55+

$700ks - $800ks

Bloomfields 55+, Frederick, MD

New Construction | 55+ age-restricted | Built 2026 - present

Rosehill Manor Villas

$300ks

Rosehill Manor Villas, Hagerstown, MD

New Construction | 55+ age-restricted | Built 2022 - present | 177 homes

Winchester Landing

$300ks - $400ks

Winchester Landing, Winchester, VA

Resale Only | 55+ age-restricted | Built 2023 - 2025

Montebello

$300ks - $600ks

Montebello, Sterling, VA

New and Resale | 55+ age-restricted | Built 2022 - present | 450 homes

5 rating (2 reviews)

Potomac Green

$400ks - $800ks

Potomac Green, Ashburn, VA

Resale Only | 55+ age-restricted | Built 2005 - 2016 | 1,400 homes

3 rating (2 reviews)

Dunbarton

$300ks - $500ks

Dunbarton, Bristow, VA

Resale Only | 55+ age-restricted | Built 2000 - 2009 | 479 homes

Want to learn more about 55+ communities in Winchester Area? 55places can help!

Questions? Call us: (540) 452-4199

5 rating (1 reviews)

Gatherings at Wellington

$300ks - $400ks

Gatherings at Wellington, Manassas, VA

Resale Only | 55+ age-restricted | Built 2011 - 2016 | 135 homes

5 rating (1 reviews)

Willow Lawn Cottages

$300ks

Willow Lawn Cottages, Winchester, VA

Resale Only | 55+ age-restricted | Built 1999 - 2004 | 120 homes

Cadence at Lansdowne

$600ks

Cadence at Lansdowne, Lansdowne, VA

Resale Only | 55+ age-restricted | Built 2020 - 2024 | 74 homes

Regency at Belmont

$600ks - $900ks

Regency at Belmont, Ashburn, VA

New Construction | 55+ age-restricted | Built 2021 - present | 145 homes

Suffield Meadows

$400ks

Suffield Meadows, Warrenton, VA

Resale Only | 55+ age-restricted | Built 2005 - 2011 | 112 homes

Ballenger Run

$300ks - $400ks

Ballenger Run, Frederick, MD

Resale Only | 55+ age-restricted | Built 2019 - 2020 | 36 homes

5 rating (1 reviews)

Crestwood Village

$200ks - $500ks

Crestwood Village, Frederick, MD

Resale Only | 55+ age-restricted | Built 1979 - 1999 | 550 homes

Liberty Grove

$200ks - $300ks

Liberty Grove, Manassas, VA

Resale Only | 55+ age-restricted | Built 2005 - 2005 | 61 homes

The Signature at Broadlan...

$300ks - $400ks

The Signature at Broadlan..., Ashburn, VA

Resale Only | 55+ age-restricted | Built 2018 - 2020 | 45 homes

The Highlands at Blue Rid...

$400ks - $600ks

The Highlands at Blue Rid..., Front Royal, VA

Resale Only | 55+ age-restricted | Built 2017 - 2019 | 42 homes

5 rating (1 reviews)

Four Seasons at Vint Hill

$600ks

Four Seasons at Vint Hill, Warrenton, VA

Resale Only | 55+ age-restricted | Built 2004 - 2006 | 100 homes

Want to learn more about 55+ communities in Winchester Area? 55places can help!

Questions? Call us: (540) 452-4199

Gatherings at Potomac Sta...

$400ks - $500ks

Gatherings at Potomac Sta..., Leesburg, VA

New Construction | 55+ age-restricted | Built 2023 - 2024 | 55 homes

JerMae Estates

$300ks - $400ks

JerMae Estates, Thurmont, MD

Resale Only | 55+ age-restricted | Built 2003 - 2008 | 108 homes

The Village at Harvest Ri...

$400ks - $500ks

The Village at Harvest Ri..., Winchester, VA

Resale Only | 55+ age-restricted | Built 2005 - 2016 | 82 homes

3.7 rating (3 reviews)

Four Seasons at Ashburn V...

$300ks - $400ks

Four Seasons at Ashburn V..., Ashburn, VA

Resale Only | 55+ age-restricted | Built 2005 - 2005 | 80 homes

The Village at Foxfield

$300ks - $500ks

The Village at Foxfield, Middletown, MD

Resale Only | 55+ age-restricted | Built 2003 - 2012 | 81 homes

Cedar Meadows

$300ks - $400ks

Cedar Meadows, White Post, VA

Resale Only | 55+ age-restricted | Built 2010 - 2022 | 129 homes

Heritage Highlands

$300ks - $400ks

Heritage Highlands, Lovettsville, VA

Resale Only | 55+ age-restricted | Built 2017 - 2020 | 80 homes

Albert Courts

$100ks - $200ks

Albert Courts, Thurmont, MD

Resale Only | 55+ age-restricted | Built 1991 - 2001 | 100 homes

Cross Creek Village

$300ks

Cross Creek Village, Winchester, VA

Resale Only | 55+ age-restricted | Built 2001 - 2004 | 90 homes

Regency at Creekside

$700ks - $800ks

Regency at Creekside, Gainesville, VA

Resale Only | 55+ age-restricted | Built 2016 - 2020 | 208 homes

Cottage Glen

$400ks

Cottage Glen, Winchester, VA

New and Resale | Age-targeted | Built 2018 - present | 25 homes

Want to learn more about 55+ communities in Winchester Area? 55places can help!

Questions? Call us: (540) 452-4199

Carter's Mill

$400ks - $700ks

Carter's Mill, Haymarket, VA

New Construction | 55+ age-restricted | Built 2020 - present | 480 homes

Abrams Chase

$400ks - $500ks

Abrams Chase, Winchester, VA

New Construction | 55+ age-restricted | Built 2020 - present | 13 homes

1...2

The Village at Freedom Hills

13874 PATRIOT WAY, HAGERSTOWN, MD, 21740, Hagerstown, MD 21740

Cindy Certified

5 STATIONMASTER ST 200, LEESBURG, VA, 20..., Leesburg, VA 20175

$950,000

2 beds

2 baths

1,666 sq ft

Condo

5 STATIONMASTER ST 200, LEESBURG, VA, 20...

Birchwood at Brambleton

42920 FIREFLY SONATA TER 101, ASHBURN, V..., Ashburn, VA 20148

$550,000

2 beds

2 baths

1,625 sq ft

Condo

42920 FIREFLY SONATA TER 101, ASHBURN, V...

Community: Birchwood at Brambleton

Want to learn more about 55+ communities in Winchester Area? 55places can help!

Questions? Call us: (540) 452-4199

Lansdowne Woods of Virginia

19365 CYPRESS RIDGE TER 720, LEESBURG, V..., Leesburg, VA 20176

$314,900

1 beds

2 baths

874 sq ft

Condo

19365 CYPRESS RIDGE TER 720, LEESBURG, V...

Community: Lansdowne Woods of Virginia

Montebello

21610 HAWKSBILL HIGH CIR 102, STERLING, ..., Sterling, VA 20164

$365,000

1 beds

1 baths

964 sq ft

Condo

21610 HAWKSBILL HIGH CIR 102, STERLING, ...

Community: Montebello

Lansdowne Woods of Virginia

19355 CYPRESS RIDGE TER 307, LEESBURG, V..., Leesburg, VA 20176

$449,900

2 beds

2 baths

1,315 sq ft

Condo

19355 CYPRESS RIDGE TER 307, LEESBURG, V...

Community: Lansdowne Woods of Virginia

Four Seasons at Vint Hill

3571 SUTHERLAND CT, WARRENTON, VA, 20187, Warrenton, VA 20187

$599,000

2 beds

2 baths

1,936 sq ft

3571 SUTHERLAND CT, WARRENTON, VA, 20187

Community: Four Seasons at Vint Hill

Potomac Green

44382 CEDAR HEIGHTS DR, ASHBURN, VA, 201..., Ashburn, VA 20147

$879,000

3 beds

3 baths

2,304 sq ft

44382 CEDAR HEIGHTS DR, ASHBURN, VA, 201...

Community: Potomac Green

The Woodlands of Urbana

3510 STARLIGHT ST 401, FREDERICK, MD, 21..., Frederick, MD 21704

$514,900

2 beds

2 baths

1,783 sq ft

Condo

3510 STARLIGHT ST 401, FREDERICK, MD, 21...

Community: The Woodlands of Urbana

Dunbarton

9450 RAITH CT, BRISTOW, VA, 20136, Bristow, VA 20136

$800,000

5 beds

3 baths

4,124 sq ft

9450 RAITH CT, BRISTOW, VA, 20136

Community: Dunbarton

Trilogy® at Lake Frederick

113 PINTAIL WAY, LAKE FREDERICK, VA, 226..., Lake Frederick, VA 22630

$809,000

3 beds

4 baths

4,159 sq ft

113 PINTAIL WAY, LAKE FREDERICK, VA, 226...

Community: Trilogy® at Lake Frederick

Heritage Hunt

13984 CHELMSFORD DR, GAINESVILLE, VA, 20..., Gainesville, VA 20155

$600,000

3 beds

3 baths

2,153 sq ft

13984 CHELMSFORD DR, GAINESVILLE, VA, 20...

Community: Heritage Hunt

Regency at Dominion Valley

15140 HEATHER MILL LN 404, HAYMARKET, VA..., Haymarket, VA 20169

$470,000

2 beds

2 baths

1,499 sq ft

Condo

15140 HEATHER MILL LN 404, HAYMARKET, VA...

Community: Regency at Dominion Valley

Cindy Certified

12880 MOSAIC PARK WAY 1-B, HERNDON, VA, ..., Herndon, VA 20171

$569,000

2 beds

3 beds

3 baths

2,573 sq ft

108 VICEROY WAY, LAKE FREDERICK, VA, 226...

Community: Trilogy® at Lake Frederick

Liberty Grove

8605 LIBERTY TRL, MANASSAS, VA, 20110, Manassas, VA 20110

$549,900

$375,000

2 beds

2 baths

1,038 sq ft

Condo

19355 CYPRESS RIDGE TER 514, LEESBURG, V...

Community: Lansdowne Woods of Virginia

Regency at Dominion Valley

15100 HEATHER MILL LN 103, HAYMARKET, VA..., Haymarket, VA 20169

$449,980

2 beds

2 baths

1,499 sq ft

Condo

15100 HEATHER MILL LN 103, HAYMARKET, VA...

Community: Regency at Dominion Valley

Want to learn more about 55+ communities in Winchester Area? 55places can help!

Questions? Call us: (540) 452-4199

Heritage Hunt

13281 FIELDSTONE WAY, GAINESVILLE, VA, 2..., Gainesville, VA 20155

$720,000

3 beds

3 baths

2,520 sq ft

13281 FIELDSTONE WAY, GAINESVILLE, VA, 2...

Community: Heritage Hunt

Willow Lawn Cottages

1853 ROSSER LN, WINCHESTER, VA, 22601, Winchester, VA 22601

$400,000

2 beds

2 baths

1,186 sq ft

1853 ROSSER LN, WINCHESTER, VA, 22601

Community: Willow Lawn Cottages

The Flats at Heathcote Village by Del Webb

15492 EMERALD WAY, HAYMARKET, VA, 20169, Haymarket, VA 20169

$837,496

3 beds

3 baths

2,763 sq ft

15492 EMERALD WAY, HAYMARKET, VA, 20169

Community: The Flats at Heathcote Village by Del Webb

Lansdowne Woods of Virginia

19365 CYPRESS RIDGE TER 615, LEESBURG, V..., Leesburg, VA 20176

$470,000

3 beds

2 baths

1,475 sq ft

Condo

19365 CYPRESS RIDGE TER 615, LEESBURG, V...

Community: Lansdowne Woods of Virginia

Cindy Certified

3 STATIONMASTER ST 201, LEESBURG, VA, 20..., Leesburg, VA 20175

$980,000

2 baths

1,345 sq ft

Condo

5800 MOONSTONE WAY 2, HAYMARKET, VA, 201...

Community: The Flats at Heathcote Village by Del Webb

Want to learn more about 55+ communities in Winchester Area? 55places can help!

Questions? Call us: (540) 452-4199

The Flats at Heathcote Village by Del Webb

5800 MOONSTONE WAY 1, HAYMARKET, VA, 201..., Haymarket, VA 20169

$494,990

2 beds

2 baths

1,475 sq ft

Condo

5800 MOONSTONE WAY 1, HAYMARKET, VA, 201...

Community: The Flats at Heathcote Village by Del Webb

Winchester Landing

120 MAURY WAY, WINCHESTER, VA, 22602, Winchester, VA 22602

$369,999

3 beds

3 baths

1,630 sq ft

120 MAURY WAY, WINCHESTER, VA, 22602

Community: Winchester Landing

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Winchester Area

Frequently Asked Questions

What size 55+ communities are there in the Winchester Area?

In the Winchester Area, there are no large communities, 1 medium community with 500-1000 homes, and 10 small communities with less than 500 homes.

How many homes are there in the smallest, largest, and average 55+ communities in the Winchester Area?

The smallest 55+ communities in the Winchester Area has 13 homes, the largest has 950 homes, and the average communities consists of 173 homes.

Are there new 55+ homes available in the Winchester Area?

Yes, there are new 55+ homes available in the Winchester Area. The most recent communities started in the Winchester Area include Winchester Landing, Abrams Chase, Cottage Glen. There are also 4 communities in the Winchester Area that offer new construction homes, including Cottage Glen, Trilogy® at Lake Frederick, Willow Run.

Are there gated 55+ communities in the Winchester Area?

Yes, there are gated 55+ communities in the Winchester Area. Approximately 33.3% of 55+ communities in the area are gated. For instance, Cottage Glen is a gated communities with 25 homes, and Cedar Meadows is another gated communities with 129 homes.

How long do listings in 55+ communities in the Winchester Area typically stay on the market, and what is the average price of homes for sale?

On average, listings in 55+ communities in the Winchester Area stay on the market for around 620 days. The average price of homes for sale in these communities is approximately $480,385, though prices can range widely based on the size, location, and amenities of the communities. For example, homes in The Village at Harvest Ridge average around $625,881, while homes in Cottage Glen average around $464,750.

Want to learn more about 55+ communities in the Winchester Area?

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229 homes

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REIN updates its listings on a daily basis. Data last updated: Sep 06, 2026.
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Winchester Area, VA 55+ active adult communities & homes for sale - Page 2

51 communities near Winchester Area

229 homes near Winchester Area

2 beds

2 baths

1,430 sq ft

3 beds

2 baths

1,554 sq ft

Condo

2 beds

2 baths

1,038 sq ft

Condo

2 beds

2 baths

1,666 sq ft

Condo

2 beds

2 baths

1,625 sq ft

Condo

1 beds

2 baths

874 sq ft

Condo

1 beds

1 baths

964 sq ft

Condo

2 beds

2 baths

1,315 sq ft

Condo

2 beds

2 baths

1,936 sq ft

3 beds

3 baths

2,304 sq ft

2 beds

2 baths

1,783 sq ft

Condo

5 beds

3 baths

4,124 sq ft

3 beds

4 baths

4,159 sq ft

3 beds

3 baths

2,153 sq ft

2 beds

2 baths

1,499 sq ft

Condo

2 beds

2 baths

1,333 sq ft

Condo

2 beds

2 baths

1,384 sq ft

Condo

2 beds

2 baths

1,101 sq ft

Condo

3 beds

3 baths

2,492 sq ft

Condo

2 beds

2 baths

1,181 sq ft

Condo

2 beds

2 baths

1,558 sq ft