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

51 communities near Winchester Area

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5 rating (2 reviews)

Trilogy® at Lake Frederic...

- $900ks

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

Willow Run

$500ks - $600ks

Willow Run, Winchester, VA

New Construction | 55+ age-restricted | 300 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 (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

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Questions? Call us: (540) 452-4199

5 rating (3 reviews)

Heritage Hunt

$400ks - $600ks

Heritage Hunt, Gainesville, VA

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

Emerald Pointe

$300ks - $500ks

Emerald Pointe, Hagerstown, MD

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

Rosehill Manor Villas

$300ks

Rosehill Manor Villas, Hagerstown, MD

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

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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 (2 reviews)

Potomac Green

$400ks - $800ks

Potomac Green, Ashburn, VA

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

Cadence at Lansdowne

$600ks

Cadence at Lansdowne, Lansdowne, VA

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

5 rating (1 reviews)

Crestwood Village

$200ks - $500ks

Crestwood Village, Frederick, MD

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

Liberty Grove

$200ks - $300ks

Liberty Grove, Manassas, VA

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

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

Questions? Call us: (540) 452-4199

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

Robinson Manor

$600ks - $700ks

Robinson Manor, Gainesville, VA

New Construction | 55+ age-restricted | Built 2023 - present | 50 homes

Montebello

$500ks - $800ks

Montebello, Sterling, VA

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

Cedar Meadows

$300ks - $400ks

Cedar Meadows, White Post, VA

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

Cottage Glen

$400ks

Cottage Glen, Winchester, VA

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

CobbleStone Estates

$400ks - $500ks

CobbleStone Estates, Hagerstown, MD

New and Resale | 55+ age-restricted | Built 2015 - present | 66 homes

The Village at Foxfield

$300ks - $500ks

The Village at Foxfield, Middletown, MD

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

Lexington Square

$800ks - $1Ms

Lexington Square, Ashburn, VA

New Construction | 55+ age-restricted | Built 2024 - present | 23 homes

Winchester Landing

$300ks - $400ks

Winchester Landing, Winchester, VA

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

The Village at Harvest Ri...

$400ks - $500ks

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

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

5 rating (1 reviews)

Willow Lawn Cottages

$300ks

Willow Lawn Cottages, Winchester, VA

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

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

Questions? Call us: (540) 452-4199

3 rating (2 reviews)

Dunbarton

$300ks - $500ks

Dunbarton, Bristow, VA

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

Regency at Creekside

$700ks - $800ks

Regency at Creekside, Gainesville, VA

Resale Only | 55+ age-restricted | Built 2016 - 2020 | 208 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 Highlands at Blue Rid...

$400ks - $600ks

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

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

Lexington 7

$600ks - $700ks

Lexington 7, Ashburn, VA

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

The Retreat at Poland Hil...

$800ks

The Retreat at Poland Hil..., Chantilly, VA

Resale Only | 55+ age-restricted | Built 2020 - 2022 | 219 homes

Abrams Chase

$400ks - $500ks

Abrams Chase, Winchester, VA

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

Vistas at Lansdowne

$800ks

Vistas at Lansdowne, Lansdowne, VA

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

Woodbrook Village

$200ks - $300ks

Woodbrook Village, Winchester, VA

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

Gatherings at Potomac Sta...

$400ks - $500ks

Gatherings at Potomac Sta..., Leesburg, VA

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

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

Questions? Call us: (540) 452-4199

Albert Courts

$100ks - $200ks

Albert Courts, Thurmont, MD

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

Suffield Meadows

$400ks

Suffield Meadows, Warrenton, VA

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

1...2

New Regency at Dominion Valley

15471 CHAMPIONSHIP DR, HAYMARKET, VA, 20..., Haymarket, VA 20169

$985,000

3 beds

3 baths

3,160 sq ft

15471 CHAMPIONSHIP DR, HAYMARKET, VA, 20...

Community: Regency at Dominion Valley

New Trilogy® at Lake Frederick

117 MALLARD DR, LAKE FREDERICK, VA, 2263..., Lake Frederick, VA 22630

$780,000

3 beds

4 baths

3,601 sq ft

117 MALLARD DR, LAKE FREDERICK, VA, 2263...

Community: Trilogy® at Lake Frederick

New Gatherings at Potomac Station

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

$609,000

2 beds

2 baths

1,809 sq ft

Condo

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

Community: Gatherings at Potomac Station

New The Woodlands of Urbana

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

$870,000

3 beds

3 baths

2,712 sq ft

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

Community: The Woodlands of Urbana

New Lansdowne Woods of Virginia

19365 CYPRESS RIDGE TER 907, LEESBURG, V..., Leesburg, VA 20176

$585,000

3 beds

3 baths

1,720 sq ft

Condo

19365 CYPRESS RIDGE TER 907, LEESBURG, V...

Community: Lansdowne Woods of Virginia

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

Questions? Call us: (540) 452-4199

New Crestwood Village

5811 BOX ELDER CT B, FREDERICK, MD, 2170..., Frederick, MD 21703

$265,000

2 beds

1 baths

Condo

5811 BOX ELDER CT B, FREDERICK, MD, 2170...

Community: Crestwood Village

New Trilogy® at Lake Frederick

128 TURNSTONE LN, LAKE FREDERICK, VA, 22..., Lake Frederick, VA 22630

$680,000

2 beds

4 baths

3,696 sq ft

128 TURNSTONE LN, LAKE FREDERICK, VA, 22...

Community: Trilogy® at Lake Frederick

New Trilogy® at Lake Frederick

152 MILKWEED DR, LAKE FREDERICK, VA, 226..., Lake Frederick, VA 22630

$530,000

3 beds

2 baths

1,804 sq ft

152 MILKWEED DR, LAKE FREDERICK, VA, 226...

Community: Trilogy® at Lake Frederick

New Rosehill Manor Villas

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

$479,990

3 beds

3 baths

1,895 sq ft

19704 OLEANDER CT, HAGERSTOWN, MD, 21742

Community: Rosehill Manor Villas

New Rosehill Manor Villas

19702 OLEANDER CT, HAGERSTOWN, MD, 21742, Hagerstown, MD 21742

$419,990

2 beds

2 baths

1,819 sq ft

19702 OLEANDER CT, HAGERSTOWN, MD, 21742

Community: Rosehill Manor Villas

New CobbleStone Estates

18208 WISTERIA WAY, HAGERSTOWN, MD, 2174..., Hagerstown, MD 21740

$389,900

2 beds

2 baths

1,432 sq ft

18208 WISTERIA WAY, HAGERSTOWN, MD, 2174...

Community: CobbleStone Estates

New Lansdowne Woods of Virginia

19355 CYPRESS RIDGE TER 103, LEESBURG, V..., Leesburg, VA 20176

$374,999

2 beds

2 baths

1,251 sq ft

Condo

19355 CYPRESS RIDGE TER 103, LEESBURG, V...

Community: Lansdowne Woods of Virginia

New Regency at Dominion Valley

15231 ROYAL CREST DR 204, HAYMARKET, VA,..., Haymarket, VA 20169

$460,000

2 beds

2 baths

1,499 sq ft

Condo

15231 ROYAL CREST DR 204, HAYMARKET, VA,...

Community: Regency at Dominion Valley

Suffield Meadows

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

$585,000

3 beds

4 baths

3,350 sq ft

Condo

6715 HOLLY FARM LN, WARRENTON, VA, 20187

Community: Suffield Meadows

Regency at Dominion Valley

15550 ALDERBROOK DR, HAYMARKET, VA, 2016..., Haymarket, VA 20169

$800,000

2 beds

3 baths

3,741 sq ft

15550 ALDERBROOK DR, HAYMARKET, VA, 2016...

Community: Regency at Dominion Valley

Potomac Green

20789 ADAMS MILL PL, ASHBURN, VA, 20147, Ashburn, VA 20147

$745,000

3 beds

3 baths

2,447 sq ft

20789 ADAMS MILL PL, ASHBURN, VA, 20147

Community: Potomac Green

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

Questions? Call us: (540) 452-4199

Dunbarton

$550,000

2 beds

2 baths

1,884 sq ft

12984 DUNBARTON DR, BRISTOW, VA, 20136

Community: Dunbarton

The Village at Foxfield

7 DERR LN, MIDDLETOWN, MD, 21769, Middletown, MD 21769

$675,000

3 beds

3 baths

2,208 sq ft

7 DERR LN, MIDDLETOWN, MD, 21769

Community: The Village at Foxfield

Heritage Hunt

6922 WALNUT HILL DR, GAINESVILLE, VA, 20..., Gainesville, VA 20155

$535,000

2 beds

2 baths

1,432 sq ft

6922 WALNUT HILL DR, GAINESVILLE, VA, 20...

Community: Heritage Hunt

The Flats at Heathcote Village by Del Webb

5800 MOONSTONE WAY 202, HAYMARKET, VA, 2..., Haymarket, VA 20169

$622,140

3 beds

2 baths

1,850 sq ft

Condo

5800 MOONSTONE WAY 202, HAYMARKET, VA, 2...

Community: The Flats at Heathcote Village by Del Webb

The Flats at Heathcote Village by Del Webb

5800 MOONSTONE WAY 203, HAYMARKET, VA, 2..., Haymarket, VA 20169

$520,005

2 beds

2 baths

1,445 sq ft

Condo

5800 MOONSTONE WAY 203, HAYMARKET, VA, 2...

Community: The Flats at Heathcote Village by Del Webb

The Flats at Heathcote Village by Del Webb

5800 MOONSTONE WAY 104, HAYMARKET, VA, 2..., Haymarket, VA 20169

$456,065

2 beds

2 baths

1,345 sq ft

Condo

5800 MOONSTONE WAY 104, HAYMARKET, VA, 2...

Community: The Flats at Heathcote Village by Del Webb

Heritage Hunt

17657 GLASS RIDGE PL, GAINESVILLE, VA, 2..., Gainesville, VA 20155

$585,000

4 beds

3 baths

2,156 sq ft

17657 GLASS RIDGE PL, GAINESVILLE, VA, 2...

Community: Heritage Hunt

Heritage Hunt

$400,000

2 beds

2 baths

1,292 sq ft

Condo

7065 HERITAGE HUNT DR 208, GAINESVILLE, ...

Community: Heritage Hunt

Robinson Manor

14714 GRAND CRU LOOP, GAINESVILLE, VA, 2..., Gainesville, VA 20155

$750,000

4 beds

4 baths

2,651 sq ft

14714 GRAND CRU LOOP, GAINESVILLE, VA, 2...

Community: Robinson Manor

Heritage Hunt

$435,000

3 beds

2 baths

1,424 sq ft

Condo

7055 HERITAGE HUNT DR 210, GAINESVILLE, ...

Community: Heritage Hunt

Regency at Ashburn

44568 GRANITE RUN TER, ASHBURN, VA, 2014..., Ashburn, VA 20147

$895,000

2 beds

3 baths

3,392 sq ft

44568 GRANITE RUN TER, ASHBURN, VA, 2014...

Community: Regency at Ashburn

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

Questions? Call us: (540) 452-4199

Woodbrook Village

200 CRESTWOOD LN, WINCHESTER, VA, 22602, Winchester, VA 22602

$415,000

2 beds

2 baths

1,692 sq ft

200 CRESTWOOD LN, WINCHESTER, VA, 22602

Community: Woodbrook Village

Birchwood at Brambleton

42734 CUMULUS TER, ASHBURN, VA, 20148, Ashburn, VA 20148

$895,000

4 beds

4 baths

3,026 sq ft

42734 CUMULUS TER, ASHBURN, VA, 20148

Community: Birchwood at Brambleton

Regency at Dominion Valley

15296 WESTHAM CT, HAYMARKET, VA, 20169, Haymarket, VA 20169

$570,000

3 beds

4 baths

2,133 sq ft

Condo

15296 WESTHAM CT, HAYMARKET, VA, 20169

Community: Regency at Dominion Valley

Dunbarton

$525,000

2 beds

2 baths

1,896 sq ft

12974 DUNBARTON DR, BRISTOW, VA, 20136

Community: Dunbarton

Heritage Hunt

6921 NETHERSTONE CT, GAINESVILLE, VA, 20..., Gainesville, VA 20155

$719,999

3 beds

3 baths

2,520 sq ft

6921 NETHERSTONE CT, GAINESVILLE, VA, 20...

Community: Heritage Hunt

Regency at Creekside

6202 CHANCELLORSVILLE DR, GAINESVILLE, V..., Gainesville, VA 20155

$1,125,000

3 beds

3 baths

3,510 sq ft

6202 CHANCELLORSVILLE DR, GAINESVILLE, V...

Community: Regency at Creekside

Lansdowne Woods of Virginia

19385 CYPRESS RIDGE TER 514, LEESBURG, V..., Leesburg, VA 20176

$515,000

2 beds

2 baths

1,509 sq ft

Condo

19385 CYPRESS RIDGE TER 514, LEESBURG, V...

Community: Lansdowne Woods of Virginia

Lansdowne Woods of Virginia

19375 CYPRESS RIDGE TER 604, LEESBURG, V..., Leesburg, VA 20176

$340,000

2 beds

2 baths

1,038 sq ft

Condo

19375 CYPRESS RIDGE TER 604, LEESBURG, V...

Community: Lansdowne Woods of Virginia

Heritage Hunt

13972 REAL QUITE CT, GAINESVILLE, VA, 20..., Gainesville, VA 20155

$810,000

4 beds

4 baths

3,256 sq ft

13972 REAL QUITE CT, GAINESVILLE, VA, 20...

Community: Heritage Hunt

Birchwood at Brambleton

23651 HAVELOCK WALK TER 304, ASHBURN, VA..., Ashburn, VA 20148

$469,900

2 beds

2 baths

1,229 sq ft

Condo

23651 HAVELOCK WALK TER 304, ASHBURN, VA...

Community: Birchwood at Brambleton

Liberty Grove

8600 LIBERTY TRL 204, MANASSAS, VA, 2011..., Manassas, VA 20110

$322,700

2 beds

3 baths

1,743 sq ft

Condo

8600 LIBERTY TRL 204, MANASSAS, VA, 2011...

Community: Liberty Grove

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

Questions? Call us: (540) 452-4199

Heritage Hunt

6907 BROADLEAF TER, GAINESVILLE, VA, 201..., Gainesville, VA 20155

$775,000

3 beds

3 baths

2,653 sq ft

6907 BROADLEAF TER, GAINESVILLE, VA, 201...

Community: Heritage Hunt

Birchwood at Brambleton

23665 HAVELOCK WALK TER 406, ASHBURN, VA..., Ashburn, VA 20148

$525,000

1 beds

2 baths

1,229 sq ft

Condo

23665 HAVELOCK WALK TER 406, 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 9 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 161 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 Abrams Chase, Cottage Glen, The Highlands at Blue Ridge Shadows. There are also 3 communities in the Winchester Area that offer new construction homes, including Abrams Chase, Trilogy® at Lake Frederick, Cottage Glen.

Are there gated 55+ communities in the Winchester Area?

Yes, there are gated 55+ communities in the Winchester Area. Approximately 30.0% of 55+ communities in the area are gated. For instance, Cedar Meadows is a gated communities with 129 homes, and Trilogy® at Lake Frederick is another gated communities with 950 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 602 days. The average price of homes for sale in these communities is approximately $484,040, though prices can range widely based on the size, location, and amenities of the communities. For example, homes in The Highlands at Blue Ridge Shadows average around $615,000, while homes in Cottage Glen average around $479,500.

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

Insights and market stats
Instant new home alerts
Answers from local 55+ experts

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

Call us: (540) 452-4199

51 communities

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The listings data displayed on this medium comes in part from the Real Estate Information Network Inc. (REIN) and has been authorized by participating listing Broker Members of REIN for display. REIN's listings are based upon Data submitted by its Broker Members, and REIN therefore makes no representation or warranty regarding the accuracy of the Data. All users of REIN's listings database should confirm the accuracy of the listing information directly with the listing agent.
© 2026 REIN. REIN's listings Data and information is protected under federal copyright laws. Federal law prohibits, among other acts, the unauthorized copying or alteration of, or preparation of derivative works from, all or any part of copyrighted materials, including certain compilations of Data and information. COPYRIGHT VIOLATORS MAY BE SUBJECT TO SEVERE FINES AND PENALTIES UNDER FEDERAL LAW.
REIN updates its listings on a daily basis. Data last updated: Apr 24, 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

210 homes near Winchester Area

3 beds

3 baths

3,160 sq ft

3 beds

4 baths

3,601 sq ft

2 beds

2 baths

1,809 sq ft

Condo

3 beds

3 baths

2,712 sq ft

3 beds

3 baths

1,720 sq ft

Condo

2 beds

1 baths

Condo

2 beds

4 baths

3,696 sq ft

3 beds

2 baths

1,804 sq ft

3 beds

3 baths

1,895 sq ft

2 beds

2 baths

1,819 sq ft

2 beds

2 baths

1,432 sq ft

2 beds

2 baths

1,251 sq ft

Condo

2 beds

2 baths

1,499 sq ft

Condo

3 beds

4 baths

3,350 sq ft

Condo

2 beds

3 baths

3,741 sq ft

3 beds

3 baths

2,447 sq ft

2 beds

2 baths

1,884 sq ft

3 beds

3 baths

2,208 sq ft

2 beds

2 baths

1,432 sq ft

3 beds

2 baths

1,850 sq ft

Condo

2 beds

2 baths

1,445 sq ft

Condo

2 beds

2 baths

1,345 sq ft

Condo

4 beds

3 baths

2,156 sq ft