Winchester Area, VA 55+ active adult communities & homes for sale - Page 5

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

Heritage Hunt

13963 CHELMSFORD DR, GAINESVILLE, VA, 20..., Gainesville, VA 20155

$530,000

3 beds

3 baths

2,090 sq ft

13963 CHELMSFORD DR, GAINESVILLE, VA, 20...

Community: Heritage Hunt

Willow Lawn Cottages

1845 ROSSER LN, WINCHESTER, VA, 22601, Winchester, VA 22601

3 beds

3 baths

3,557 sq ft

110 PIPIT CT, LAKE FREDERICK, VA, 22630

Community: Trilogy® at Lake Frederick

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

Questions? Call us: (540) 452-4199

Cadence at Lansdowne

19006 CORAL REEF SQ, LEESBURG, VA, 20176, Leesburg, VA 20176

$939,900

3 beds

5 baths

3,679 sq ft

19006 CORAL REEF SQ, LEESBURG, VA, 20176

Community: Cadence at Lansdowne

Trilogy® at Lake Frederick

145 COWBIRD, LAKE FREDERICK, VA, 22630, Lake Frederick, VA 22630

$558,900

3 beds

2 baths

1,771 sq ft

145 COWBIRD, LAKE FREDERICK, VA, 22630

Community: Trilogy® at Lake Frederick

Cindy Certified

46270 MOUNT ALLEN TER 101, STERLING, VA,..., Sterling, VA 20164

$499,900

2 beds

2 baths

1,524 sq ft

Condo

46270 MOUNT ALLEN TER 101, STERLING, VA,...

Cindy Certified

21913 DURBERRY RD, SMITHSBURG, MD, 21783, Smithsburg, MD 21783

$475,025

3 beds

2 baths

1,518 sq ft

21913 DURBERRY RD, SMITHSBURG, MD, 21783

Suffield Meadows

6708 STREAM VIEW LN, WARRENTON, VA, 2018..., Warrenton, VA 20187

$600,000

3 beds

3 baths

3,701 sq ft

Condo

6708 STREAM VIEW LN, WARRENTON, VA, 2018...

Community: Suffield Meadows

Birchwood at Brambleton

23640 BOLTON CRESCENT TER 403, ASHBURN, ..., Ashburn, VA 20148

$724,900

$699,990

3 beds

3 baths

2,915 sq ft

2613 BROADLEAF, FREDERICK, MD, 21702

Community: Bloomfields 55+

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

Questions? Call us: (540) 452-4199

Trilogy® at Lake Frederick

134 ATLANTIS LN, LAKE FREDERICK, VA, 226..., Lake Frederick, VA 22630

$565,000

3 beds

3 baths

2,173 sq ft

134 ATLANTIS LN, LAKE FREDERICK, VA, 226...

Community: Trilogy® at Lake Frederick

Four Seasons at Ashburn Village

21007 ROCKY KNOLL SQ 205, ASHBURN, VA, 2..., Ashburn, VA 20147

$500,000

2 beds

2 baths

1,491 sq ft

Condo

21007 ROCKY KNOLL SQ 205, ASHBURN, VA, 2...

Community: Four Seasons at Ashburn Village

Rosehill Manor Villas

19601 LAVENDER LN, HAGERSTOWN, MD, 21742, Hagerstown, MD 21742

$374,900

3 beds

2 baths

1,735 sq ft

19601 LAVENDER LN, HAGERSTOWN, MD, 21742

Community: Rosehill Manor Villas

Lansdowne Woods of Virginia

19385 CYPRESS RIDGE TER 519, LEESBURG, V..., Leesburg, VA 20176

$319,990

2 beds

4 beds

3 baths

2,270 sq ft

LOT 4 GRAY MEADOW CT, WARRENTON, VA, 201...

Cindy Certified

LOT 5 GRAY MEADOW CT, WARRENTON, VA, 201..., Warrenton, VA 20187

$799,850

3 beds

2 baths

1,768 sq ft

LOT 5 GRAY MEADOW CT, WARRENTON, VA, 201...

Trilogy® at Lake Frederick

110 SWITCHGRASS WAY, LAKE FREDERICK, VA,..., Lake Frederick, VA 22630

$545,000

2 beds

2 baths

1,791 sq ft

110 SWITCHGRASS WAY, LAKE FREDERICK, VA,...

Community: Trilogy® at Lake Frederick

Gatherings at Wellington

9204 CHARLESTON DR 207, MANASSAS, VA, 20..., Manassas, VA 20110

$399,900

2 beds

2 baths

2,006 sq ft

Condo

9204 CHARLESTON DR 207, MANASSAS, VA, 20...

Community: Gatherings at Wellington

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

Questions? Call us: (540) 452-4199

Cindy Certified

640 ARMSTRONG AVE, HAGERSTOWN, MD, 21740, Hagerstown, MD 21740

$389,990

2,250 sq ft

120 LEATHER FLOWER DR, LAKE FREDERICK, V...

Community: Trilogy® at Lake Frederick

Gatherings at Potomac Station

700 MOUNT AIRY TER 301, LEESBURG, VA, 20..., Leesburg, VA 20176

$549,999

2 beds

2 baths

1,809 sq ft

Condo

700 MOUNT AIRY TER 301, LEESBURG, VA, 20...

Community: Gatherings at Potomac Station

The Woodlands of Urbana

2913 HERB GARDEN DR, FREDERICK, MD, 2170..., Frederick, MD 21704

$849,000

3 beds

3 baths

3,070 sq ft

2913 HERB GARDEN DR, FREDERICK, MD, 2170...

Community: The Woodlands of Urbana

Rosehill Manor Villas

19704 OLEANDER CT, HAGERSTOWN, MD, 21742, Hagerstown, MD 21742

$449,990

3 beds

3 baths

1,895 sq ft

19704 OLEANDER CT, HAGERSTOWN, MD, 21742

Community: Rosehill Manor Villas

Suffield Meadows

6715 HOLLY FARM LN, WARRENTON, VA, 20187, Warrenton, VA 20187

$560,000

3 beds

4 baths

3,350 sq ft

Condo

6715 HOLLY FARM LN, WARRENTON, VA, 20187

Community: Suffield Meadows

Crestwood Village

5738 BOX ELDER CT, FREDERICK, MD, 21703, Frederick, MD 21703

$325,000

2 beds

2 baths

1,264 sq ft

5738 BOX ELDER CT, FREDERICK, MD, 21703

Community: Crestwood Village

Heritage Hunt

13891 CHELMSFORD DR 110, GAINESVILLE, VA..., Gainesville, VA 20155

$425,000

3 beds

2 baths

1,424 sq ft

Condo

13891 CHELMSFORD DR 110, GAINESVILLE, VA...

Community: Heritage Hunt

Cedar Meadows

103 BLEEDING HEART DR, WHITE POST, VA, 2..., White Post, VA 22663

$460,000

3 beds

2 baths

1,493 sq ft

103 BLEEDING HEART DR, WHITE POST, VA, 2...

Community: Cedar Meadows

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

Questions? Call us: (540) 452-4199

Lansdowne Woods of Virginia

19375 CYPRESS RIDGE TER 1111, LEESBURG, ..., Leesburg, VA 20176

$469,900

3 beds

2 baths

1,475 sq ft

Condo

19375 CYPRESS RIDGE TER 1111, LEESBURG, ...

Community: Lansdowne Woods of Virginia

Trilogy® at Lake Frederick

104 RHODODENDRON CT, LAKE FREDERICK, VA,..., Lake Frederick, VA 22630

$729,990

3 beds

3 baths

2,457 sq ft

104 RHODODENDRON CT, LAKE FREDERICK, VA,...

Community: Trilogy® at Lake Frederick

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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 5

51 communities near Winchester Area

229 homes near Winchester Area

3 beds

3 baths

2,090 sq ft

2 beds

2 baths

1,200 sq ft

2 beds

2 baths

1,499 sq ft

Condo

2 beds

2 baths

1,168 sq ft

Condo

3 beds

3 baths

3,557 sq ft

3 beds

5 baths

3,679 sq ft

3 beds

2 baths

1,771 sq ft

2 beds

2 baths

1,524 sq ft

Condo

3 beds

2 baths

1,518 sq ft

3 beds

3 baths

3,701 sq ft

Condo

3 beds

2 baths

1,908 sq ft

Condo

2 beds

2 baths

2,915 sq ft

4 beds

4 baths

4,034 sq ft

4 beds

4 baths

3,591 sq ft

3 beds

3 baths

3,357 sq ft

3 beds

3 baths

2,915 sq ft

3 beds

3 baths

2,173 sq ft

2 beds

2 baths

1,491 sq ft

Condo

3 beds

2 baths

1,735 sq ft

2 beds

2 baths

1,038 sq ft

Condo

2 beds

2 baths

1,219 sq ft

2 beds

2 baths

1,451 sq ft

Condo

2 beds

2 baths

1,663 sq ft