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

50 communities near Winchester Area

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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 (2 reviews)

Trilogy® at Lake Frederic...

$300ks - $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

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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)

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

5 rating (1 reviews)

Crestwood Village

$200ks - $500ks

Crestwood Village, Frederick, MD

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

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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

Cadence at Lansdowne

$600ks

Cadence at Lansdowne, Lansdowne, VA

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

The Woodlands of Urbana

$500ks - $700ks

The Woodlands of Urbana, Urbana, MD

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

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Questions? Call us: (540) 452-4199

5 rating (1 reviews)

Gatherings at Wellington

$300ks - $400ks

Gatherings at Wellington, Manassas, VA

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

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

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

Questions? Call us: (540) 452-4199

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

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

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

Questions? Call us: (540) 452-4199

Woodbrook Village

$200ks - $300ks

Woodbrook Village, Winchester, VA

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

5 rating (1 reviews)

Willow Lawn Cottages

$300ks

Willow Lawn Cottages, Winchester, VA

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

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

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

Questions? Call us: (540) 452-4199

Cottage Glen

$400ks

Cottage Glen, Winchester, VA

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

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

Questions? Call us: (540) 452-4199

Regency at Ashburn

$300ks - $800ks

Regency at Ashburn, Ashburn, VA

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

Suffield Meadows

$400ks

Suffield Meadows, Warrenton, VA

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

3 rating (2 reviews)

Dunbarton

$300ks - $500ks

Dunbarton, Bristow, VA

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

Carter's Mill

$400ks - $700ks

Carter's Mill, Haymarket, VA

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

JerMae Estates

$300ks - $400ks

JerMae Estates, Thurmont, MD

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

Albert Courts

$100ks - $200ks

Albert Courts, Thurmont, MD

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

Heritage Highlands

$300ks - $400ks

Heritage Highlands, Lovettsville, VA

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

The Villages at Broadland...

$400ks

The Villages at Broadland..., Ashburn, VA

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

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

Questions? Call us: (540) 452-4199

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

6052 SUNSTONE LN, HAYMARKET, VA, 20169

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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Questions? Call us: (540) 452-4199

New Birchwood at Brambleton

23631 HAVELOCK WALK TER 421, ASHBURN, VA..., Ashburn, VA 20148

$555,000

3 beds

2 baths

1,906 sq ft

Condo

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

Community: Birchwood at Brambleton

New Heritage Hunt

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

2 beds

2 baths

1,345 sq ft

Condo

5800 MOONSTONE WAY 2, HAYMARKET, VA, 201...

Community: The Flats at Heathcote Village by Del Webb

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Questions? Call us: (540) 452-4199

New The Flats at Heathcote Village by Del Webb

5800 MOONSTONE WAY 1, HAYMARKET, VA, 201..., Haymarket, VA 20169

$494,990

2 beds

2 baths

1,475 sq ft

Condo

5800 MOONSTONE WAY 1, HAYMARKET, VA, 201...

Community: The Flats at Heathcote Village by Del Webb

New The Village at Foxfield

1 KELLER LN, MIDDLETOWN, MD, 21769, Middletown, MD 21769

$564,900

3 beds

3 baths

3,161 sq ft

1 KELLER LN, MIDDLETOWN, MD, 21769

Community: The Village at Foxfield

New The Woodlands of Urbana

3315 FIREFLY LN UNIT 304, FREDERICK, MD,..., Frederick, MD 21704

$469,900

2 beds

2 baths

1,517 sq ft

Condo

3315 FIREFLY LN UNIT 304, FREDERICK, MD,...

Community: The Woodlands of Urbana

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Questions? Call us: (540) 452-4199

New Crestwood Village

7058 CATALPA RD, FREDERICK, MD, 21703, Frederick, MD 21703

$337,000

2 beds

2 baths

1,232 sq ft

7058 CATALPA RD, FREDERICK, MD, 21703

Community: Crestwood Village

New Heritage Hunt

7055 HERITAGE HUNT DR 311, GAINESVILLE, ..., Gainesville, VA 20155

$440,000

2 beds

2 baths

1,421 sq ft

Condo

7055 HERITAGE HUNT DR 311, GAINESVILLE, ...

Community: Heritage Hunt

New Potomac Green

20763 CRESCENT POINTE PL, ASHBURN, VA, 2..., Ashburn, VA 20147

$849,999

3 beds

3 baths

2,810 sq ft

20763 CRESCENT POINTE PL, ASHBURN, VA, 2...

Community: Potomac Green

Heritage Highlands

77 HARPERS MILL WAY, LOVETTSVILLE, VA, 2..., Lovettsville, VA 20180

$540,000

3 beds

3 baths

2,119 sq ft

77 HARPERS MILL WAY, LOVETTSVILLE, VA, 2...

Community: Heritage Highlands

Willow Lawn Cottages

1885 ROSSER LN, WINCHESTER, VA, 22601, Winchester, VA 22601

$389,900

2 beds

2 baths

1,550 sq ft

1885 ROSSER LN, WINCHESTER, VA, 22601

Community: Willow Lawn Cottages

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

Questions? Call us: (540) 452-4199

Regency at Dominion Valley

15110 HEATHER MILL LN APT 402, HAYMARKET..., Haymarket, VA 20169

$480,000

2 beds

2 baths

1,551 sq ft

Condo

15110 HEATHER MILL LN APT 402, HAYMARKET...

Community: Regency at Dominion Valley

Regency at Dominion Valley

5112 FALDO DR, HAYMARKET, VA, 20169, Haymarket, VA 20169

$800,000

3 beds

3 baths

2,754 sq ft

5112 FALDO DR, HAYMARKET, VA, 20169

Community: Regency at Dominion Valley

Birchwood at Brambleton

23631 HAVELOCK WALK TER UNIT 302, ASHBUR..., Ashburn, VA 20148

$449,900

2 beds

2 baths

1,244 sq ft

Condo

23631 HAVELOCK WALK TER UNIT 302, ASHBUR...

Community: Birchwood at Brambleton

Rosehill Manor Villas

19604 LAVENDER LN, HAGERSTOWN, MD, 21742, Hagerstown, MD 21742

$384,900

2 beds

2 baths

1,767 sq ft

19604 LAVENDER LN, HAGERSTOWN, MD, 21742

Community: Rosehill Manor Villas

Potomac Green

44397 OAKMONT MANOR SQ, ASHBURN, VA, 201..., Ashburn, VA 20147

$725,000

3 beds

3 baths

2,118 sq ft

44397 OAKMONT MANOR SQ, ASHBURN, VA, 201...

Community: Potomac Green

Willow Run

121 SCENTED ROSE WAY, WINCHESTER, VA, 22..., Winchester, VA 22602

$604,990

4 beds

3 baths

2,818 sq ft

121 SCENTED ROSE WAY, WINCHESTER, VA, 22...

Community: Willow Run

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Willow Run

117 SCENTED ROSE WAY, WINCHESTER, VA, 22..., Winchester, VA 22602

$604,990

4 beds

3 baths

2,865 sq ft

117 SCENTED ROSE WAY, WINCHESTER, VA, 22...

Community: Willow Run

Trilogy® at Lake Frederick

109 BAYHILL TER, LAKE FREDERICK, VA, 226..., Lake Frederick, VA 22630

$425,000

3 beds

4 baths

2,304 sq ft

109 BAYHILL TER, LAKE FREDERICK, VA, 226...

Community: Trilogy® at Lake Frederick

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Cadence at Lansdowne

18989 CORAL REEF SQ, LEESBURG, VA, 20176, Leesburg, VA 20176

$747,800

3 beds

3 baths

2,649 sq ft

18989 CORAL REEF SQ, LEESBURG, VA, 20176

Community: Cadence at Lansdowne

Willow Run

119 SCENTED ROSE WAY, WINCHESTER, VA, 22..., Winchester, VA 22602

$619,990

4 beds

3 baths

2,909 sq ft

119 SCENTED ROSE WAY, WINCHESTER, VA, 22...

Community: Willow Run

Birchwood at Brambleton

23642 WINTERDAY DR, ASHBURN, VA, 20148, Ashburn, VA 20148

$799,990

3 beds

4 baths

2,742 sq ft

23642 WINTERDAY DR, ASHBURN, VA, 20148

Community: Birchwood at Brambleton

Potomac Green

20655 HOPE SPRING TER 104, ASHBURN, VA, ..., Ashburn, VA 20147

$350,000

2 beds

2 baths

876 sq ft

Condo

20655 HOPE SPRING TER 104, ASHBURN, VA, ...

Community: Potomac Green

Crestwood Village

5798 BOX ELDER CT, FREDERICK, MD, 21703, Frederick, MD 21703

$526,000

2 beds

2 baths

2,044 sq ft

5798 BOX ELDER CT, FREDERICK, MD, 21703

Community: Crestwood Village

Crestwood Village

7046 CATALPA RD, FREDERICK, MD, 21703, Frederick, MD 21703

$339,900

2 beds

2 baths

1,226 sq ft

7046 CATALPA RD, FREDERICK, MD, 21703

Community: Crestwood Village

Trilogy® at Lake Frederick

116 CHAMOMILE CT, LAKE FREDERICK, VA, 22..., Lake Frederick, VA 22630

$360,000

3 beds

3 baths

2,350 sq ft

116 CHAMOMILE CT, LAKE FREDERICK, VA, 22...

Community: Trilogy® at Lake Frederick

Central Parke at Lowes Island

20816 NOBLE TER 312, STERLING, VA, 20165, Sterling, VA 20165

$485,000

2 beds

2 baths

1,989 sq ft

Condo

20816 NOBLE TER 312, STERLING, VA, 20165

Community: Central Parke at Lowes Island

Trilogy® at Lake Frederick

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

$880,000

4 beds

4 baths

4,804 sq ft

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

Community: Trilogy® at Lake Frederick

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

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Regency at Dominion Valley

5375 TREVINO DR, HAYMARKET, VA, 20169, Haymarket, VA 20169

$779,000

4 beds

4 baths

3,527 sq ft

5375 TREVINO DR, HAYMARKET, VA, 20169

Community: Regency at Dominion Valley

JerMae Estates

6 SYLVIA CIR, THURMONT, MD, 21788, Thurmont, MD 21788

$485,000

4 beds

3 baths

2,766 sq ft

6 SYLVIA CIR, THURMONT, MD, 21788

Community: JerMae Estates

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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?

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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 14, 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

154 homes near Winchester Area

4 beds

3 baths

3,026 sq ft

3 beds

3 baths

2,848 sq ft

3 beds

3 baths

2,714 sq ft

3 beds

3 baths

3,036 sq ft

3 beds

3 baths

2,763 sq ft

3 beds

2 baths

1,906 sq ft

Condo

4 beds

3 baths

2,126 sq ft

2 beds

2 baths

1,445 sq ft

Condo

1 beds

2 baths

995 sq ft

Condo

3 beds

2 baths

1,850 sq ft

Condo

2 beds

2 baths

1,520 sq ft

Condo

3 beds

2 baths

1,735 sq ft

Condo

2 beds

2 baths

1,345 sq ft

Condo

2 beds

2 baths

1,475 sq ft

Condo

3 beds

3 baths

3,161 sq ft

2 beds

2 baths

1,517 sq ft

Condo

2 beds

2 baths

1,232 sq ft

2 beds

2 baths

1,421 sq ft

Condo

3 beds

3 baths

2,810 sq ft

3 beds

3 baths

2,119 sq ft

2 beds

2 baths

1,550 sq ft

2 beds

2 baths

1,551 sq ft

Condo