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

51 communities near Winchester Area

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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

5 rating (2 reviews)

Trilogy® at Lake Frederic...

$400ks - $1Ms

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

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

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

5 rating (3 reviews)

Heritage Hunt

$400ks - $600ks

Heritage Hunt, Gainesville, VA

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

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

Questions? Call us: (540) 452-4199

5 rating (1 reviews)

Crestwood Village

$200ks - $500ks

Crestwood Village, Frederick, MD

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

The Woodlands of Urbana

$500ks - $700ks

The Woodlands of Urbana, Urbana, MD

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

Bloomfields 55+

$700ks - $800ks

Bloomfields 55+, Frederick, MD

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

5 rating (2 reviews)

Potomac Green

$400ks - $800ks

Potomac Green, Ashburn, VA

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

Regency at Belmont

$600ks - $900ks

Regency at Belmont, Ashburn, VA

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

Winchester Landing

$300ks - $400ks

Winchester Landing, Winchester, VA

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

Willow Run

$500ks - $600ks

Willow Run, Winchester, VA

New Construction | 55+ age-restricted | 300 homes

Rosehill Manor Villas

$300ks

Rosehill Manor Villas, Hagerstown, MD

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

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

Questions? Call us: (540) 452-4199

Emerald Pointe

$300ks - $500ks

Emerald Pointe, Hagerstown, MD

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

5 rating (1 reviews)

Gatherings at Wellington

$300ks - $400ks

Gatherings at Wellington, Manassas, VA

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

Cedar Meadows

$300ks - $400ks

Cedar Meadows, White Post, VA

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

Suffield Meadows

$400ks

Suffield Meadows, Warrenton, VA

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

Vistas at Lansdowne

$800ks

Vistas at Lansdowne, Lansdowne, VA

Resale Only | 55+ age-restricted | Built 2015 - 2020 | 120 homes

Heritage Highlands

$300ks - $400ks

Heritage Highlands, Lovettsville, VA

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

3 rating (2 reviews)

Dunbarton

$300ks - $500ks

Dunbarton, Bristow, VA

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

Liberty Grove

$200ks - $300ks

Liberty Grove, Manassas, VA

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

Montebello

$300ks - $600ks

Montebello, Sterling, VA

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

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

Questions? Call us: (540) 452-4199

JerMae Estates

$300ks - $400ks

JerMae Estates, Thurmont, MD

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

Boxwood Villas

$500ks - $600ks

Boxwood Villas, Urbana, MD

Resale Only | 55+ age-restricted | Built 2019 - 2021 | 92 homes

Woodbrook Village

$200ks - $300ks

Woodbrook Village, Winchester, VA

Resale Only | 55+ age-restricted | Built 1999 - 2001 | 81 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

Cross Creek Village

$300ks

Cross Creek Village, Winchester, VA

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

Central Parke at Lowes Is...

$300ks - $600ks

Central Parke at Lowes Is..., Sterling, VA

Resale Only | 55+ age-restricted | Built 2003 - 2005 | 181 homes

Regency at Ashburn

$300ks - $800ks

Regency at Ashburn, Ashburn, VA

Resale Only | 55+ age-restricted | Built 2013 - 2020 | 268 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

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

Lexington 7

$600ks - $700ks

Lexington 7, Ashburn, VA

Resale Only | 55+ age-restricted | Built 2017 - 2020 | 113 homes

The Signature at Broadlan...

$300ks - $400ks

The Signature at Broadlan..., Ashburn, VA

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

The Village at Foxfield

$300ks - $500ks

The Village at Foxfield, Middletown, MD

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

1...2

Heritage Hunt

$399,900

2 beds

2 baths

1,292 sq ft

Condo

7065 HERITAGE HUNT DR 108, GAINESVILLE, ...

Community: Heritage Hunt

Trilogy® at Lake Frederick

109 EMPEROR DR, LAKE FREDERICK, VA, 2263..., Lake Frederick, VA 22630

$569,900

4 beds

4 baths

3,859 sq ft

109 EMPEROR DR, LAKE FREDERICK, VA, 2263...

Community: Trilogy® at Lake Frederick

New Crestwood Village

5594 TEAKWOOD CT, FREDERICK, MD, 21703, Frederick, MD 21703

$359,900

2 beds

2 baths

1,227 sq ft

5594 TEAKWOOD CT, FREDERICK, MD, 21703

Community: Crestwood Village

New Regency at Dominion Valley

5133 CURRAN CREEK DR, HAYMARKET, VA, 201..., Haymarket, VA 20169

$520,000

3 beds

3 baths

2,374 sq ft

5133 CURRAN CREEK DR, HAYMARKET, VA, 201...

Community: Regency at Dominion Valley

New Vistas at Lansdowne

44241 SILVERPALM GROVE TER, LEESBURG, VA..., Leesburg, VA 20176

$999,900

3 beds

4 baths

3,990 sq ft

44241 SILVERPALM GROVE TER, LEESBURG, VA...

Community: Vistas at Lansdowne

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

Questions? Call us: (540) 452-4199

New Heritage Hunt

13729 HERITAGE VALLEY WAY, GAINESVILLE, ..., Gainesville, VA 20155

$642,500

2 beds

3 baths

1,668 sq ft

Condo

23650 HAVELOCK WALK TER 308, ASHBURN, VA...

Community: Birchwood at Brambleton

Cindy Certified

12875 MOSAIC PARK WAY 4-D, HERNDON, VA, ..., Herndon, VA 20171

$539,900

2 beds

2 baths

1,333 sq ft

Condo

12875 MOSAIC PARK WAY 4-D, HERNDON, VA, ...

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

Questions? Call us: (540) 452-4199

Heritage Hunt

6900 SADDLE RUN WAY, GAINESVILLE, VA, 20..., Gainesville, VA 20155

3 beds

3 baths

2,751 sq ft

Condo

210 E SECOND ST 401, FREDERICK, MD, 2170...

Cindy Certified

3927 FAIR RIDGE DR 207, FAIRFAX, VA, 220..., Fairfax, VA 22033

$549,999

2 beds

2 baths

1,301 sq ft

Condo

3927 FAIR RIDGE DR 207, FAIRFAX, VA, 220...

The Flats at Heathcote Village by Del Webb

5988 SUNSTONE LN, HAYMARKET, VA, 20169, Haymarket, VA 20169

$702,616

3 beds

3 baths

2,625 sq ft

5988 SUNSTONE LN, HAYMARKET, VA, 20169

Community: The Flats at Heathcote Village by Del Webb

Lansdowne Woods of Virginia

19385 CYPRESS RIDGE TER 604, LEESBURG, V..., Leesburg, VA 20176

$374,900

2 beds

2 baths

1,038 sq ft

Condo

19385 CYPRESS RIDGE TER 604, LEESBURG, V...

Community: Lansdowne Woods of Virginia

Crestwood Village

6874 BUTTONWOOD CT, FREDERICK, MD, 21703, Frederick, MD 21703

$349,900

2 beds

2 baths

1,164 sq ft

6874 BUTTONWOOD CT, FREDERICK, MD, 21703

Community: Crestwood Village

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

Birchwood at Brambleton

42724 CUSHING TER, ASHBURN, VA, 20148, Ashburn, VA 20148

$960,000

3 beds

4 baths

3,735 sq ft

42724 CUSHING TER, ASHBURN, VA, 20148

Community: Birchwood at Brambleton

Regency at Dominion Valley

15508 HAGEN WAY, HAYMARKET, VA, 20169, Haymarket, VA 20169

$849,000

3 beds

3 baths

4,050 sq ft

15508 HAGEN WAY, HAYMARKET, VA, 20169

Community: Regency at Dominion Valley

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

Questions? Call us: (540) 452-4199

Ballenger Run

5312 CRAPE MYRTLE DR, FREDERICK, MD, 217..., Frederick, MD 21703

$525,000

3 beds

4 baths

3,944 sq ft

5312 CRAPE MYRTLE DR, FREDERICK, MD, 217...

Community: Ballenger Run

Cindy Certified

12850 MOSAIC PARK WAY 2B, HERNDON, VA, 2..., Herndon, VA 20171

$585,000

3 baths

3,031 sq ft

225 HYDRANGEA WAY, WINCHESTER, VA, 22602

Community: Willow Run

Potomac Green

44473 BLUERIDGE MEADOWS DR, ASHBURN, VA,..., Ashburn, VA 20147

$909,500

3 beds

3 baths

2,817 sq ft

44473 BLUERIDGE MEADOWS DR, ASHBURN, VA,...

Community: Potomac Green

Bloomfields 55+

2641 BROADLEAF DR, FREDERICK, MD, 21702, Frederick, MD 21702

$899,990

3 beds

4 baths

4,501 sq ft

2641 BROADLEAF DR, FREDERICK, MD, 21702

Community: Bloomfields 55+

Bloomfields 55+

2603 - C BLAZING STAR ST, FREDERICK, MD,..., Frederick, MD 21702

$804,990

4 beds

4 baths

4,062 sq ft

2603 - C BLAZING STAR ST, FREDERICK, MD,...

Community: Bloomfields 55+

Bloomfields 55+

2603 - D BLAZING STAR ST, FREDERICK, MD,..., Frederick, MD 21702

$834,990

4 beds

4 baths

4,501 sq ft

2603 - D BLAZING STAR ST, FREDERICK, MD,...

Community: Bloomfields 55+

Bloomfields 55+

2603 - B BLAZING STAR ST, FREDERICK, MD,..., Frederick, MD 21702

$754,990

3 beds

3 baths

3,821 sq ft

2603 - B BLAZING STAR ST, FREDERICK, MD,...

Community: Bloomfields 55+

Bloomfields 55+

2603 - A BLAZING STAR ST, FREDERICK, MD,..., Frederick, MD 21702

$724,990

3 beds

3 baths

3,387 sq ft

2603 - A BLAZING STAR ST, FREDERICK, MD,...

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

121 FOAM FLOWER DR, LAKE FREDERICK, VA, ..., Lake Frederick, VA 22630

$619,900

3 beds

2 baths

2,089 sq ft

121 FOAM FLOWER DR, LAKE FREDERICK, VA, ...

Community: Trilogy® at Lake Frederick

Birchwood at Brambleton

23630 HAVELOCK WALK TER 410, ASHBURN, VA..., Ashburn, VA 20148

$465,000

2 beds

2 baths

1,212 sq ft

Condo

23630 HAVELOCK WALK TER 410, ASHBURN, VA...

Community: Birchwood at Brambleton

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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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51 communities

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REIN updates its listings on a daily basis. Data last updated: Oct 13, 2026.
This application does not include information on all of the properties available for sale at this time.

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

51 communities near Winchester Area

241 homes near Winchester Area

2 beds

2 baths

1,292 sq ft

Condo

4 beds

4 baths

3,859 sq ft

2 beds

2 baths

1,227 sq ft

3 beds

3 baths

2,374 sq ft

3 beds

4 baths

3,990 sq ft

4 beds

3 baths

2,758 sq ft

2 beds

2 baths

1,550 sq ft

Condo

2 beds

2 baths

1,445 sq ft

Condo

3 beds

2 baths

1,850 sq ft

Condo

2 beds

2 baths

1,345 sq ft

Condo

3 beds

3 baths

2,625 sq ft

3 beds

3 baths

3,424 sq ft

3 beds

3 baths

2,763 sq ft

3 beds

3 baths

3,531 sq ft

2 beds

3 baths

1,668 sq ft

Condo

2 beds

2 baths

1,333 sq ft

Condo

2 beds

2 baths

2,058 sq ft

1 beds

2 baths

874 sq ft

Condo

2 beds

2 baths

1,347 sq ft

Condo

3 beds

3 baths

2,751 sq ft

Condo

2 beds

2 baths

1,301 sq ft

Condo

3 beds

3 baths

2,625 sq ft