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

238 homes 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 - $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

2 rating (1 review)

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

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Questions? Call us: (540) 452-4199

5 rating (1 review)

Crestwood Village

$200ks - $500ks

Crestwood Village, Frederick, MD

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

5 rating (1 review)

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

Regency at Belmont

$600ks - $900ks

Regency at Belmont, Ashburn, VA

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

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5 rating (1 review)

Willow Lawn Cottages

$300ks

Willow Lawn Cottages, Winchester, VA

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

5 rating (2 reviews)

Potomac Green

$400ks - $800ks

Potomac Green, Ashburn, VA

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

Emerald Pointe

$300ks - $500ks

Emerald Pointe, Hagerstown, MD

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

Willow Run

$500ks - $600ks

Willow Run, Winchester, VA

New Construction | 55+ age-restricted | 300 homes

Cadence at Lansdowne

$600ks

Cadence at Lansdowne, Lansdowne, VA

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

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

Heritage Highlands

$300ks - $400ks

Heritage Highlands, Lovettsville, VA

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

Winchester Landing

$300ks - $400ks

Winchester Landing, Winchester, VA

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

Rosehill Manor Villas

$300ks

Rosehill Manor Villas, Hagerstown, MD

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

Liberty Grove

$200ks - $300ks

Liberty Grove, Manassas, VA

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

5 rating (1 review)

Gatherings at Wellington

$300ks - $400ks

Gatherings at Wellington, Manassas, VA

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

Vistas at Lansdowne

$800ks

Vistas at Lansdowne, Lansdowne, VA

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

3 rating (2 reviews)

Dunbarton

$300ks - $500ks

Dunbarton, Bristow, VA

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

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 review)

Four Seasons at Vint Hill

$600ks

Four Seasons at Vint Hill, Warrenton, VA

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

Woodbrook Village

$200ks - $300ks

Woodbrook Village, Winchester, VA

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

Boxwood Villas

$500ks - $600ks

Boxwood Villas, Urbana, MD

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

Lexington 7

$600ks - $700ks

Lexington 7, Ashburn, VA

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

Regency at Ashburn

$300ks - $800ks

Regency at Ashburn, Ashburn, VA

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

Cross Creek Village

$300ks

Cross Creek Village, Winchester, VA

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

Gatherings at Potomac Sta...

$400ks - $500ks

Gatherings at Potomac Sta..., Leesburg, VA

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

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

Robinson Manor

$600ks - $700ks

Robinson Manor, Gainesville, VA

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

The Villages at Broadland...

$400ks

The Villages at Broadland..., Ashburn, VA

New and Resale | 55+ age-restricted | Built 2013 - present | 78 homes

1...2

Cindy Certified

20122 REGENT CIR, HAGERSTOWN, MD, 21742, Hagerstown, MD 21742

$399,990

3 beds

2 baths

1,368 sq ft

20122 REGENT CIR, HAGERSTOWN, MD, 21742

Cindy Certified

20127 REGENT CIR, HAGERSTOWN, MD, 21742, Hagerstown, MD 21742

$499,990

3 beds

2 baths

1,988 sq ft

20127 REGENT CIR, HAGERSTOWN, MD, 21742

Four Seasons at Ashburn Village

44465 CHAMBERLAIN TER 102, ASHBURN, VA, ..., Ashburn, VA 20147

$535,000

2 beds

2 baths

1,710 sq ft

Condo

44465 CHAMBERLAIN TER 102, ASHBURN, VA, ...

Community: Four Seasons at Ashburn Village

Cindy Certified

24637 WOOLLY MAMMOTH TER 205, ALDIE, VA,..., Aldie, VA 20105

$495,000

3 beds

2 baths

1,712 sq ft

Condo

24637 WOOLLY MAMMOTH TER 205, ALDIE, VA,...

Gatherings at Wellington

9202 CHARLESTON DR 207, MANASSAS, VA, 20..., Manassas, VA 20110

$419,950

3 beds

2 baths

2,006 sq ft

Condo

9202 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

Central Parke at Lowes Island

20816 NOBLE TER 210, STERLING, VA, 20165, Sterling, VA 20165

$485,000

3 beds

2 baths

1,989 sq ft

Condo

20816 NOBLE TER 210, STERLING, VA, 20165

Community: Central Parke at Lowes Island

Trilogy® at Lake Frederick

109 WALLEYE CT, LAKE FREDERICK, VA, 2263..., Lake Frederick, VA 22630

$589,900

2 beds

2 baths

1,839 sq ft

109 WALLEYE CT, LAKE FREDERICK, VA, 2263...

Community: Trilogy® at Lake Frederick

Trilogy® at Lake Frederick

106 FRINGETREE CT, LAKE FREDERICK, VA, 2..., Lake Frederick, VA 22630

$650,000

5 beds

3 baths

4,047 sq ft

106 FRINGETREE CT, LAKE FREDERICK, VA, 2...

Community: Trilogy® at Lake Frederick

Cindy Certified

6295 VIRGINIA BLUEBELL LN, HAYMARKET, VA..., Haymarket, VA 20169

$599,975

2 beds

2 baths

1,593 sq ft

6295 VIRGINIA BLUEBELL LN, HAYMARKET, VA...

Regency at Dominion Valley

15233 BRIER CREEK DR, HAYMARKET, VA, 201..., Haymarket, VA 20169

$775,000

3 beds

3 baths

3,023 sq ft

15233 BRIER CREEK DR, HAYMARKET, VA, 201...

Community: Regency at Dominion Valley

Lansdowne Woods of Virginia

19370 MAGNOLIA GROVE SQ 212, LEESBURG, V..., Leesburg, VA 20176

$430,000

2 beds

2 baths

1,444 sq ft

Condo

19370 MAGNOLIA GROVE SQ 212, LEESBURG, V...

Community: Lansdowne Woods of Virginia

The Woodlands of Urbana

3519 STARLIGHT ST 401, FREDERICK, MD, 21..., Frederick, MD 21704

$484,900

2 beds

2 baths

1,734 sq ft

Condo

3519 STARLIGHT ST 401, FREDERICK, MD, 21...

Community: The Woodlands of Urbana

Boxwood Villas

9247 BEALLS FARM RD, FREDERICK, MD, 2170..., Frederick, MD 21704

$795,000

3 beds

4 baths

4,173 sq ft

9247 BEALLS FARM RD, FREDERICK, MD, 2170...

Community: Boxwood Villas

Birchwood at Brambleton

42841 CUMULUS TER, ASHBURN, VA, 20148, Ashburn, VA 20148

$959,900

3 beds

3 baths

2,832 sq ft

42841 CUMULUS TER, ASHBURN, VA, 20148

Community: Birchwood at Brambleton

Regency at Dominion Valley

15584 LEGACY WAY, HAYMARKET, VA, 20169, Haymarket, VA 20169

$750,000

3 beds

3 baths

2,515 sq ft

15584 LEGACY WAY, HAYMARKET, VA, 20169

Community: Regency at Dominion Valley

Regency at Ashburn

44589 YORK CREST TER 405, ASHBURN, VA, 2..., Ashburn, VA 20147

$520,000

2 beds

2 baths

1,491 sq ft

Condo

44589 YORK CREST TER 405, ASHBURN, VA, 2...

Community: Regency at Ashburn

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

Questions? Call us: (540) 452-4199

Heritage Hunt

13439 FIELDSTONE WAY, GAINESVILLE, VA, 2..., Gainesville, VA 20155

$910,000

4 beds

4 baths

4,293 sq ft

13439 FIELDSTONE WAY, GAINESVILLE, VA, 2...

Community: Heritage Hunt

Emerald Pointe

13332 MARQUISE DR, HAGERSTOWN, MD, 21742, Hagerstown, MD 21742

$399,900

2 beds

2 baths

2,615 sq ft

13332 MARQUISE DR, HAGERSTOWN, MD, 21742

Community: Emerald Pointe

Crestwood Village

7016 BASSWOOD RD, FREDERICK, MD, 21703, Frederick, MD 21703

$349,900

2 beds

2 baths

1,128 sq ft

7016 BASSWOOD RD, FREDERICK, MD, 21703

Community: Crestwood Village

Heritage Hunt

6912 BIRKENHEAD PL, GAINESVILLE, VA, 201..., Gainesville, VA 20155

$734,000

3 beds

4 baths

3,415 sq ft

6912 BIRKENHEAD PL, GAINESVILLE, VA, 201...

Community: Heritage Hunt

Potomac Green

20523 CRESCENT POINTE PL, ASHBURN, VA, 2..., Ashburn, VA 20147

$895,000

3 beds

3 baths

2,707 sq ft

20523 CRESCENT POINTE PL, ASHBURN, VA, 2...

Community: Potomac Green

Dunbarton

12868 ARNOT LN, BRISTOW, VA, 20136, Bristow, VA 20136

$585,000

2 beds

2 baths

1,924 sq ft

12868 ARNOT LN, BRISTOW, VA, 20136

Community: Dunbarton

Regency at Belmont

19820 BODMER DR, ASHBURN, VA, 20147, Ashburn, VA 20147

$1,075,000

3 beds

4 baths

3,255 sq ft

19820 BODMER DR, ASHBURN, VA, 20147

Community: Regency at Belmont

Crestwood Village

5746 BOX ELDER CT, FREDERICK, MD, 21703, Frederick, MD 21703

$358,500

2 beds

2 baths

1,225 sq ft

5746 BOX ELDER CT, FREDERICK, MD, 21703

Community: Crestwood Village

Birchwood at Brambleton

42849 LITTLEHALES TER, ASHBURN, VA, 2014..., Ashburn, VA 20148

$565,000

3 beds

3 baths

2,412 sq ft

Condo

42849 LITTLEHALES TER, ASHBURN, VA, 2014...

Community: Birchwood at Brambleton

Regency at Dominion Valley

15231 ROYAL CREST DR 101, HAYMARKET, VA,..., Haymarket, VA 20169

$459,900

2 beds

2 baths

1,538 sq ft

Condo

15231 ROYAL CREST DR 101, HAYMARKET, VA,...

Community: Regency at Dominion Valley

Cindy Certified

22145 HEADWATER TER 400, ASHBURN, VA, 20..., Ashburn, VA 20148

$960,000

3 beds

3 baths

2,285 sq ft

Condo

22145 HEADWATER TER 400, ASHBURN, VA, 20...

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

Questions? Call us: (540) 452-4199

Lansdowne Woods of Virginia

19350 MAGNOLIA GROVE SQ 201, LEESBURG, V..., Leesburg, VA 20176

$409,000

2 beds

2 baths

1,387 sq ft

Condo

19350 MAGNOLIA GROVE SQ 201, LEESBURG, V...

Community: Lansdowne Woods of Virginia

Heritage Hunt

6322 ANOKA WAY, GAINESVILLE, VA, 20155, Gainesville, VA 20155

$625,000

3 beds

3 baths

2,139 sq ft

6322 ANOKA WAY, GAINESVILLE, VA, 20155

Community: Heritage Hunt

Regency at Belmont

43929 NORMAN NEWS TER, ASHBURN, VA, 2014..., Ashburn, VA 20147

$1,050,000

3 beds

4 baths

3,255 sq ft

43929 NORMAN NEWS TER, ASHBURN, VA, 2014...

Community: Regency at Belmont

Crestwood Village

5714 TAMARACK AVE, FREDERICK, MD, 21703, Frederick, MD 21703

$404,900

2 beds

2 baths

1,297 sq ft

5714 TAMARACK AVE, FREDERICK, MD, 21703

Community: Crestwood Village

The Flats at Heathcote Village by Del Webb

5810 MOONSTONE WAY 101, HAYMARKET, VA, 2..., Haymarket, VA 20169

$429,095

2 beds

2 baths

1,175 sq ft

Condo

5810 MOONSTONE WAY 101, HAYMARKET, VA, 2...

Community: The Flats at Heathcote Village by Del Webb

The Flats at Heathcote Village by Del Webb

5800 MOONSTONE WAY 107, HAYMARKET, VA, 2..., Haymarket, VA 20169

$411,080

1 beds

2 baths

1,175 sq ft

Condo

5800 MOONSTONE WAY 107, HAYMARKET, VA, 2...

Community: The Flats at Heathcote Village by Del Webb

Crestwood Village

7011 BASSWOOD RD, FREDERICK, MD, 21703, Frederick, MD 21703

$365,000

2 beds

2 baths

1,227 sq ft

7011 BASSWOOD RD, FREDERICK, MD, 21703

Community: Crestwood Village

Lansdowne Woods of Virginia

19375 CYPRESS RIDGE TER 702, LEESBURG, V..., Leesburg, VA 20176

$354,900

2 beds

2 baths

1,038 sq ft

Condo

19375 CYPRESS RIDGE TER 702, LEESBURG, V...

Community: Lansdowne Woods of Virginia

Cedar Meadows

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

$495,000

3 beds

2 baths

1,634 sq ft

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

Community: Cedar Meadows

Trilogy® at Lake Frederick

118 HARVESTER DR, LAKE FREDERICK, VA, 22..., Lake Frederick, VA 22630

$650,000

3 beds

4 baths

3,889 sq ft

118 HARVESTER DR, LAKE FREDERICK, VA, 22...

Community: Trilogy® at Lake Frederick

Potomac Green

20429 ISLAND W SQ, ASHBURN, VA, 20147, Ashburn, VA 20147

$745,000

3 beds

3 baths

2,253 sq ft

20429 ISLAND W SQ, 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

Potomac Green

20594 GOLDEN RIDGE DR, ASHBURN, VA, 2014..., Ashburn, VA 20147

$910,000

3 beds

4 baths

2,973 sq ft

20594 GOLDEN RIDGE DR, ASHBURN, VA, 2014...

Community: Potomac Green

Trilogy® at Lake Frederick

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

$599,999

4 beds

4 baths

3,232 sq ft

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

Community: Trilogy® at Lake Frederick

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Winchester Area

Frequently Asked Questions

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

Of the 12 55+ communities in the Winchester Area, 12 are for sale and none are rentals. By size, 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 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 588 days. The average price of homes for sale in these communities is approximately $491,100, though prices can range widely based on the size, location, and amenities of the communities. For example, homes in Willow Run average around $623,623, while homes in Cottage Glen average around $464,750.

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

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238 homes

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© 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.
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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 2

51 communities near Winchester Area

238 homes near Winchester Area

3 beds

2 baths

1,368 sq ft

3 beds

2 baths

1,988 sq ft

2 beds

2 baths

1,710 sq ft

Condo

3 beds

2 baths

1,712 sq ft

Condo

3 beds

2 baths

2,006 sq ft

Condo

3 beds

2 baths

1,989 sq ft

Condo

2 beds

2 baths

1,839 sq ft

5 beds

3 baths

4,047 sq ft

2 beds

2 baths

1,593 sq ft

3 beds

3 baths

3,023 sq ft

2 beds

2 baths

1,444 sq ft

Condo

2 beds

2 baths

1,734 sq ft

Condo

3 beds

4 baths

4,173 sq ft

3 beds

3 baths

2,832 sq ft

3 beds

3 baths

2,515 sq ft

2 beds

2 baths

1,491 sq ft

Condo

4 beds

4 baths

4,293 sq ft

2 beds

2 baths

2,615 sq ft

2 beds

2 baths

1,128 sq ft

3 beds

4 baths

3,415 sq ft

3 beds

3 baths

2,707 sq ft

2 beds

2 baths

1,924 sq ft

3 beds

4 baths

3,255 sq ft

2 beds