Winchester Area, VA 55+ active adult communities & homes for sale - Page 3

219 homes near Winchester Area

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5 rating (2 reviews)

Trilogy® at Lake Frederic...

$300ks - $1Ms

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

Willow Run

$500ks - $600ks

Willow Run, Winchester, VA

New Construction | 55+ age-restricted | 300 homes

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

Questions? Call us: (540) 452-4199

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

The Woodlands of Urbana

$500ks - $700ks

The Woodlands of Urbana, Urbana, MD

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

5 rating (1 reviews)

Crestwood Village

$200ks - $500ks

Crestwood Village, Frederick, MD

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

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

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.

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

Cedar Meadows

$300ks - $400ks

Cedar Meadows, White Post, VA

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

Regency at Dominion Valle...

$300ks - $1Ms

Regency at Dominion Valle..., Haymarket, VA

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

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

Questions? Call us: (540) 452-4199

Liberty Grove

$200ks - $300ks

Liberty Grove, Manassas, VA

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

Regency at Belmont

$600ks - $900ks

Regency at Belmont, Ashburn, VA

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

Montebello

$500ks - $700ks

Montebello, Sterling, VA

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

Suffield Meadows

$400ks

Suffield Meadows, Warrenton, VA

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

5 rating (1 reviews)

Willow Lawn Cottages

$300ks

Willow Lawn Cottages, Winchester, VA

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

3 rating (2 reviews)

Dunbarton

$300ks - $500ks

Dunbarton, Bristow, VA

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

5 rating (1 reviews)

Gatherings at Wellington

$300ks - $400ks

Gatherings at Wellington, Manassas, VA

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

Robinson Manor

$600ks - $700ks

Robinson Manor, Gainesville, VA

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

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

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

Abrams Chase

$400ks - $500ks

Abrams Chase, Winchester, VA

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

JerMae Estates

$300ks - $400ks

JerMae Estates, Thurmont, MD

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

Lexington 7

$600ks - $700ks

Lexington 7, Ashburn, VA

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

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

Questions? Call us: (540) 452-4199

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

Cross Creek Village

$300ks

Cross Creek Village, Winchester, VA

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

1...2

Trilogy® at Lake Frederick

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

$842,900

4 beds

4 baths

4,804 sq ft

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

Community: Trilogy® at Lake Frederick

Heritage Hunt

13455 BRIGHTVIEW WAY, GAINESVILLE, VA, 2..., Gainesville, VA 20155

$899,000

3 beds

3 baths

3,080 sq ft

13455 BRIGHTVIEW WAY, GAINESVILLE, VA, 2...

Community: Heritage Hunt

The Woodlands of Urbana

3224 IVY MEADOW DR, FREDERICK, MD, 21704, Frederick, MD 21704

$915,000

2 beds

3 baths

2,812 sq ft

3224 IVY MEADOW DR, FREDERICK, MD, 21704

Community: The Woodlands of Urbana

Gatherings at Wellington

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

$409,900

2 beds

2 baths

2,006 sq ft

Condo

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

Community: Gatherings at Wellington

Lansdowne Woods of Virginia

19355 CYPRESS RIDGE TER 1022, LEESBURG, ..., Leesburg, VA 20176

$380,000

2 beds

2 baths

1,038 sq ft

Condo

19355 CYPRESS RIDGE TER 1022, LEESBURG, ...

Community: Lansdowne Woods of Virginia

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

Questions? Call us: (540) 452-4199

Regency at Belmont

43917 MERCER RUN TER, ASHBURN, VA, 20147, Ashburn, VA 20147

$1,025,000

3 beds

4 baths

3,243 sq ft

43917 MERCER RUN TER, ASHBURN, VA, 20147

Community: Regency at Belmont

Lansdowne Woods of Virginia

19355 CYPRESS RIDGE TER 404, LEESBURG, V..., Leesburg, VA 20176

$358,500

2 beds

2 baths

1,105 sq ft

Condo

19355 CYPRESS RIDGE TER 404, LEESBURG, V...

Community: Lansdowne Woods of Virginia

Central Parke at Lowes Island

20745 ROYAL PALACE SQ 209, STERLING, VA,..., Sterling, VA 20165

$475,000

3 beds

2 baths

1,816 sq ft

Condo

20745 ROYAL PALACE SQ 209, STERLING, VA,...

Community: Central Parke at Lowes Island

Birchwood at Brambleton

42863 BEAVER CROSSING SQ, ASHBURN, VA, 2..., Ashburn, VA 20148

$1,079,900

3 beds

3 baths

2,830 sq ft

42863 BEAVER CROSSING SQ, ASHBURN, VA, 2...

Community: Birchwood at Brambleton

Lansdowne Woods of Virginia

19355 CYPRESS RIDGE TER 314, LEESBURG, V..., Leesburg, VA 20176

$334,990

2 beds

2 baths

1,038 sq ft

Condo

19355 CYPRESS RIDGE TER 314, LEESBURG, V...

Community: Lansdowne Woods of Virginia

The Woodlands of Urbana

3411 ANGELICA WAY 401, FREDERICK, MD, 21..., Frederick, MD 21704

$525,000

2 beds

2 baths

1,785 sq ft

Condo

3411 ANGELICA WAY 401, FREDERICK, MD, 21...

Community: The Woodlands of Urbana

Trilogy® at Lake Frederick

102 PEREGRINE CT, LAKE FREDERICK, VA, 22..., Lake Frederick, VA 22630

$775,000

3 beds

3 baths

3,051 sq ft

102 PEREGRINE CT, LAKE FREDERICK, VA, 22...

Community: Trilogy® at Lake Frederick

Heritage Hunt

13001 TRIPLE CROWN LOOP, GAINESVILLE, VA..., Gainesville, VA 20155

$850,000

4 beds

3 baths

4,074 sq ft

13001 TRIPLE CROWN LOOP, GAINESVILLE, VA...

Community: Heritage Hunt

Birchwood at Brambleton

42729 AUTUMN DAY TER, ASHBURN, VA, 20148, Ashburn, VA 20148

$1,015,000

3 beds

3 baths

2,802 sq ft

42729 AUTUMN DAY TER, ASHBURN, VA, 20148

Community: Birchwood at Brambleton

Rosehill Manor Villas

19642 LAVENDER LN, HAGERSTOWN, MD, 21742, Hagerstown, MD 21742

$399,900

3 beds

2 baths

1,712 sq ft

19642 LAVENDER LN, HAGERSTOWN, MD, 21742

Community: Rosehill Manor Villas

Suffield Meadows

6704 HOLLY FARM LN 112, WARRENTON, VA, 2..., Warrenton, VA 20187

$430,000

2 beds

2 baths

1,754 sq ft

Condo

6704 HOLLY FARM LN 112, WARRENTON, VA, 2...

Community: Suffield Meadows

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

Questions? Call us: (540) 452-4199

Trilogy® at Lake Frederick

105 TROUT LILY DR, LAKE FREDERICK, VA, 2..., Lake Frederick, VA 22630

$399,900

3 beds

4 baths

2,327 sq ft

105 TROUT LILY DR, LAKE FREDERICK, VA, 2...

Community: Trilogy® at Lake Frederick

Trilogy® at Lake Frederick

120 LEATHER FLOWER DR, LAKE FREDERICK, V..., Lake Frederick, VA 22630

$420,000

3 beds

4 baths

2,250 sq ft

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

Community: Trilogy® at Lake Frederick

Lansdowne Woods of Virginia

19365 CYPRESS RIDGE TER 306, LEESBURG, V..., Leesburg, VA 20176

$365,000

2 beds

2 baths

1,315 sq ft

Condo

19365 CYPRESS RIDGE TER 306, LEESBURG, V...

Community: Lansdowne Woods of Virginia

Trilogy® at Lake Frederick

109 TUTELO LN, LAKE FREDERICK, VA, 22630, Lake Frederick, VA 22630

$589,900

2 beds

3 baths

3,505 sq ft

109 TUTELO LN, LAKE FREDERICK, VA, 22630

Community: Trilogy® at Lake Frederick

The Village at Harvest Ridge

152 HARVEST RIDGE DR, WINCHESTER, VA, 22..., Winchester, VA 22601

$625,000

3 beds

2 baths

2,444 sq ft

152 HARVEST RIDGE DR, WINCHESTER, VA, 22...

Community: The Village at Harvest Ridge

Trilogy® at Lake Frederick

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

$760,000

3 beds

4 baths

3,601 sq ft

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

Community: Trilogy® at Lake Frederick

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

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

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

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

Trilogy® at Lake Frederick

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

$514,500

3 beds

2 baths

1,804 sq ft

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

Community: Trilogy® at Lake Frederick

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

Questions? Call us: (540) 452-4199

Rosehill Manor Villas

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

$459,990

3 beds

3 baths

1,895 sq ft

19704 OLEANDER CT, HAGERSTOWN, MD, 21742

Community: Rosehill Manor Villas

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

Regency at Dominion Valley

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

$450,000

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

The Village at Foxfield

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

$650,000

3 beds

3 baths

2,208 sq ft

7 DERR LN, MIDDLETOWN, MD, 21769

Community: The Village at Foxfield

The Flats at Heathcote Village by Del Webb

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

$632,140

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

$515,005

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

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

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

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

Questions? Call us: (540) 452-4199

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

Lansdowne Woods of Virginia

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

$465,000

2 beds

2 baths

1,509 sq ft

Condo

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

Community: Lansdowne Woods of Virginia

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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 Trilogy® at Lake Frederick, Cottage Glen, Abrams Chase.

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, Trilogy® at Lake Frederick is a gated communities with 950 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 614 days. The average price of homes for sale in these communities is approximately $482,668, 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 $631,008, while homes in Cottage Glen average around $464,750.

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

219 homes

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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: May 31, 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 - Page 3

51 communities near Winchester Area

219 homes near Winchester Area

4 beds

4 baths

4,804 sq ft

3 beds

3 baths

3,080 sq ft

2 beds

3 baths

2,812 sq ft

2 beds

2 baths

2,006 sq ft

Condo

2 beds

2 baths

1,038 sq ft

Condo

3 beds

4 baths

3,243 sq ft

2 beds

2 baths

1,105 sq ft

Condo

3 beds

2 baths

1,816 sq ft

Condo

3 beds

3 baths

2,830 sq ft

2 beds

2 baths

1,038 sq ft

Condo

2 beds

2 baths

1,785 sq ft

Condo

3 beds

3 baths

3,051 sq ft

4 beds

3 baths

4,074 sq ft

3 beds

3 baths

2,802 sq ft

3 beds

2 baths

1,712 sq ft

2 beds

2 baths

1,754 sq ft

Condo

3 beds

4 baths

2,327 sq ft

3 beds

4 baths

2,250 sq ft

2 beds

2 baths

1,315 sq ft

Condo

2 beds

3 baths

3,505 sq ft

3 beds

2 baths

2,444 sq ft

3 beds

4 baths

3,601 sq ft

2 beds

2 baths

1,809 sq ft