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

50 communities near Winchester Area

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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 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 (2 reviews)

Trilogy® at Lake Frederic...

$400ks - $800ks

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

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

Willow Run

$500ks - $600ks

Willow Run, Winchester, VA

New Construction | 55+ age-restricted | 300 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

Want to learn more about 55+ rental 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

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)

Crestwood Village

$200ks - $500ks

Crestwood Village, Frederick, MD

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

Winchester Landing

$300ks - $400ks

Winchester Landing, Winchester, VA

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

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5 rating (2 reviews)

Potomac Green

$400ks - $800ks

Potomac Green, Ashburn, VA

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

Rosehill Manor Villas

$300ks

Rosehill Manor Villas, Hagerstown, MD

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

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

The Woodlands of Urbana

$500ks - $700ks

The Woodlands of Urbana, Urbana, MD

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

Lexington 7

$600ks - $700ks

Lexington 7, Ashburn, VA

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

Cadence at Lansdowne

$600ks

Cadence at Lansdowne, Lansdowne, VA

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

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

Questions? Call us: (540) 452-4199

Montebello

$500ks - $600ks

Montebello, Sterling, VA

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

Lexington Square

$800ks - $1Ms

Lexington Square, Ashburn, VA

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

Liberty Grove

$200ks - $300ks

Liberty Grove, Manassas, VA

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

Regency at Creekside

$700ks - $800ks

Regency at Creekside, Gainesville, VA

Resale Only | 55+ age-restricted | Built 2016 - 2020 | 208 homes

5 rating (1 reviews)

Willow Lawn Cottages

$300ks

Willow Lawn Cottages, Winchester, VA

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

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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

Cottage Glen

$400ks

Cottage Glen, Winchester, VA

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

Robinson Manor

$600ks - $700ks

Robinson Manor, Gainesville, VA

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

Heritage Highlands

$300ks - $400ks

Heritage Highlands, Lovettsville, VA

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

Suffield Meadows

$400ks

Suffield Meadows, Warrenton, VA

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

Abrams Chase

$400ks - $500ks

Abrams Chase, Winchester, VA

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

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

Questions? Call us: (540) 452-4199

Regency at Belmont

$600ks - $900ks

Regency at Belmont, Ashburn, VA

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

The Retreat at Poland Hil...

$800ks

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

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

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

Questions? Call us: (540) 452-4199

The Village at Freedom Hi...

$300ks

The Village at Freedom Hi..., Hagerstown, MD

New and Resale | 55+ age-restricted | Built 2007 - present | 66 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

3 rating (2 reviews)

Dunbarton

$300ks - $500ks

Dunbarton, Bristow, VA

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

Gatherings at Potomac Sta...

$400ks - $500ks

Gatherings at Potomac Sta..., Leesburg, VA

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

Carter's Mill

$400ks - $700ks

Carter's Mill, Haymarket, VA

New Construction | 55+ age-restricted | Built 2020 - present | 480 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

Want to learn more about 55+ rental 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

1...2

New Gatherings at Wellington

9204 CHARLESTON DR 206, MANASSAS, VA, 20..., Manassas, VA 20110

$399,900

2 beds

2 baths

1,558 sq ft

Condo

9204 CHARLESTON DR 206, MANASSAS, VA, 20...

Community: Gatherings at Wellington

New Birchwood at Brambleton

23603 GOLDEN EMBERS SQ, ASHBURN, VA, 201..., Ashburn, VA 20148

$919,900

4 beds

4 baths

4,071 sq ft

23603 GOLDEN EMBERS SQ, ASHBURN, VA, 201...

Community: Birchwood at Brambleton

New Emerald Pointe

13428 MARQUISE DR, HAGERSTOWN, MD, 21742, Hagerstown, MD 21742

$434,000

2 beds

2 baths

1,953 sq ft

13428 MARQUISE DR, HAGERSTOWN, MD, 21742

Community: Emerald Pointe

New Lexington Square

44508 LOWESOFT SQ, ASHBURN, VA, 20147, Ashburn, VA 20147

$794,236

3 beds

3 baths

3,132 sq ft

44508 LOWESOFT SQ, ASHBURN, VA, 20147

Community: Lexington Square

New Lexington 7

$794,236

3 beds

3 baths

3,132 sq ft

44508 LOWESOFT SQ, ASHBURN, VA, 20147

Community: Lexington 7

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2,053 sq ft

Condo

23639 GOLDEN EMBERS SQ 105, ASHBURN, VA,...

Community: Birchwood at Brambleton

New Regency at Belmont

19899 HARRISON TRACE TER, ASHBURN, VA, 2..., Ashburn, VA 20147

$1,024,990

3 beds

4 baths

3,243 sq ft

19899 HARRISON TRACE TER, ASHBURN, VA, 2...

Community: Regency at Belmont

New Gatherings at Wellington

9204 CHARLESTON DR 202, MANASSAS, VA, 20..., Manassas, VA 20110

$415,000

3 beds

2 baths

2,006 sq ft

Condo

9204 CHARLESTON DR 202, MANASSAS, VA, 20...

Community: Gatherings at Wellington

New Trilogy® at Lake Frederick

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

$849,900

4 beds

4 baths

5,247 sq ft

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

Community: Trilogy® at Lake Frederick

New Willow Run

124 TRELLIS VIEW LN, WINCHESTER, VA, 226..., Winchester, VA 22602

$449,990

3 beds

2 baths

1,492 sq ft

124 TRELLIS VIEW LN, WINCHESTER, VA, 226...

Community: Willow Run

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

Questions? Call us: (540) 452-4199

New Trilogy® at Lake Frederick

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

$829,990

3 beds

4 baths

3,931 sq ft

108 RHODODENDRON CT, LAKE FREDERICK, VA,...

Community: Trilogy® at Lake Frederick

New Regency at Dominion Valley

5417 ZOYSIA CT, HAYMARKET, VA, 20169, Haymarket, VA 20169

$920,000

4 beds

4 baths

4,036 sq ft

5417 ZOYSIA CT, HAYMARKET, VA, 20169

Community: Regency at Dominion Valley

Robinson Manor

14712 GRAND CRU LOOP, GAINESVILLE, VA, 2..., Gainesville, VA 20155

$715,000

3 beds

3 baths

2,270 sq ft

14712 GRAND CRU LOOP, GAINESVILLE, VA, 2...

Community: Robinson Manor

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

Questions? Call us: (540) 452-4199

Abrams Chase

105 AMBERFIELD CT, WINCHESTER, VA, 22602, Winchester, VA 22602

$529,900

2 beds

2 baths

1,800 sq ft

105 AMBERFIELD CT, WINCHESTER, VA, 22602

Community: Abrams Chase

Dunbarton

9513 MOONEN BAY LN, BRISTOW, VA, 20136, Bristow, VA 20136

$650,000

4 beds

3 baths

2,711 sq ft

9513 MOONEN BAY LN, BRISTOW, VA, 20136

Community: Dunbarton

Heritage Hunt

6595 ALDERWOOD WAY, GAINESVILLE, VA, 201..., Gainesville, VA 20155

$625,000

3 beds

3 baths

2,311 sq ft

6595 ALDERWOOD WAY, GAINESVILLE, VA, 201...

Community: Heritage Hunt

Regency at Dominion Valley

15251 ROYAL CREST DR APT 103, HAYMARKET,..., Haymarket, VA 20169

$455,000

2 beds

2 baths

1,499 sq ft

Condo

15251 ROYAL CREST DR APT 103, HAYMARKET,...

Community: Regency at Dominion Valley

Suffield Meadows

6696 CLUB HOUSE LN 206, WARRENTON, VA, 2..., Warrenton, VA 20187

$375,000

2 beds

2 baths

1,372 sq ft

Condo

6696 CLUB HOUSE LN 206, 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

Crestwood Village

5693 CRABAPPLE DR, FREDERICK, MD, 21703, Frederick, MD 21703

$364,900

2 beds

2 baths

1,148 sq ft

5693 CRABAPPLE DR, FREDERICK, MD, 21703

Community: Crestwood Village

The Flats at Heathcote Village by Del Webb

5907 SUNSTONE LN, HAYMARKET, VA, 20169, Haymarket, VA 20169

$833,536

3 beds

3 baths

3,734 sq ft

5907 SUNSTONE LN, HAYMARKET, VA, 20169

Community: The Flats at Heathcote Village by Del Webb

Trilogy® at Lake Frederick

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

$630,000

2 beds

2 baths

2,089 sq ft

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

Community: Trilogy® at Lake Frederick

Willow Run

LOT 0057 HYDRANGEA WAY, WINCHESTER, VA, ..., Winchester, VA 22602

$564,990

3 beds

2 baths

1,748 sq ft

LOT 0057 HYDRANGEA WAY, WINCHESTER, VA, ...

Community: Willow Run

Willow Run

LOT 0055 HYDRANGEA WAY, WINCHESTER, VA, ..., Winchester, VA 22602

$576,990

3 beds

2 baths

1,865 sq ft

LOT 0055 HYDRANGEA WAY, WINCHESTER, VA, ...

Community: Willow Run

Heritage Hunt

13663 HERITAGE VALLEY WAY, GAINESVILLE, ..., Gainesville, VA 20155

$735,000

3 beds

3 baths

2,520 sq ft

13663 HERITAGE VALLEY WAY, GAINESVILLE, ...

Community: Heritage Hunt

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Heritage Hunt

13986 CHELMSFORD DR, GAINESVILLE, VA, 20..., Gainesville, VA 20155

$594,999

2,165 sq ft

13986 CHELMSFORD DR, GAINESVILLE, VA, 20...

Community: Heritage Hunt

Birchwood at Brambleton

23630 HAVELOCK WALK TER 402, ASHBURN, VA..., Ashburn, VA 20148

$469,980

2 beds

2 baths

1,244 sq ft

Condo

23630 HAVELOCK WALK TER 402, ASHBURN, VA...

1,906 sq ft

Condo

23631 HAVELOCK WALK TER 421, ASHBURN, VA...

Community: Birchwood at Brambleton

Heritage Hunt

6932 WALNUT HILL DR, GAINESVILLE, VA, 20..., Gainesville, VA 20155

$600,000

4 beds

3 baths

2,126 sq ft

6932 WALNUT HILL DR, GAINESVILLE, VA, 20...

Community: Heritage Hunt

The Flats at Heathcote Village by Del Webb

5800 MOONSTONE WAY 7, HAYMARKET, VA, 201..., Haymarket, VA 20169

$474,990

2 beds

2 baths

1,445 sq ft

Condo

5800 MOONSTONE WAY 7, HAYMARKET, VA, 201...

Community: The Flats at Heathcote Village by Del Webb

The Flats at Heathcote Village by Del Webb

5800 MOONSTONE WAY 6, HAYMARKET, VA, 201..., Haymarket, VA 20169

$374,990

1 beds

2 baths

995 sq ft

Condo

5800 MOONSTONE WAY 6, HAYMARKET, VA, 201...

Community: The Flats at Heathcote Village by Del Webb

The Flats at Heathcote Village by Del Webb

5800 MOONSTONE WAY 5, HAYMARKET, VA, 201..., Haymarket, VA 20169

$589,990

3 beds

2 baths

1,850 sq ft

Condo

5800 MOONSTONE WAY 5, HAYMARKET, VA, 201...

Community: The Flats at Heathcote Village by Del Webb

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

Questions? Call us: (540) 452-4199

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The Flats at Heathcote Village by Del Webb

5800 MOONSTONE WAY 4, HAYMARKET, VA, 201..., Haymarket, VA 20169

$539,990

2 beds

2 baths

1,520 sq ft

Condo

5800 MOONSTONE WAY 4, HAYMARKET, VA, 201...

Community: The Flats at Heathcote Village by Del Webb

The Flats at Heathcote Village by Del Webb

5800 MOONSTONE WAY 3, HAYMARKET, VA, 201..., Haymarket, VA 20169

$574,990

3 beds

2 baths

1,735 sq ft

Condo

5800 MOONSTONE WAY 3, HAYMARKET, VA, 201...

Community: The Flats at Heathcote Village by Del Webb

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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
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Answers from local 55+ experts

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

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50 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: Feb 28, 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

50 communities near Winchester Area

153 homes near Winchester Area

2 beds

2 baths

1,558 sq ft

Condo

4 beds

4 baths

4,071 sq ft

2 beds

2 baths

1,953 sq ft

3 beds

3 baths

3,132 sq ft

3 beds

3 baths

3,132 sq ft

3 beds

3 baths

2,538 sq ft

3 beds

3 baths

2,798 sq ft

3 beds

3 baths

3,788 sq ft

3 beds

2 baths

2,053 sq ft

Condo

3 beds

4 baths

3,243 sq ft

3 beds

2 baths

2,006 sq ft

Condo

4 beds

4 baths

5,247 sq ft

3 beds

2 baths

1,492 sq ft

3 beds

4 baths

3,931 sq ft

4 beds

4 baths

4,036 sq ft

3 beds

3 baths

2,270 sq ft

2 beds

2 baths

1,800 sq ft

4 beds

3 baths

2,711 sq ft

3 beds

3 baths

2,311 sq ft

2 beds

2 baths

1,499 sq ft

Condo

2 beds

2 baths

1,372 sq ft

Condo

2 beds

2 baths

1,148 sq ft

3 beds

3 baths

3,734 sq ft

2 beds

2 baths

2,089 sq ft