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...

$300ks - $1Ms

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

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

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

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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

Bloomfields 55+

$700ks - $800ks

Bloomfields 55+, Frederick, MD

New Construction | 55+ age-restricted | Built 2026 - present

The Woodlands of Urbana

$500ks - $700ks

The Woodlands of Urbana, Urbana, MD

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

Rosehill Manor Villas

$300ks

Rosehill Manor Villas, Hagerstown, MD

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

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

Cedar Meadows

$300ks - $400ks

Cedar Meadows, White Post, VA

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

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

Questions? Call us: (540) 452-4199

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

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

5 rating (1 reviews)

Willow Lawn Cottages

$300ks

Willow Lawn Cottages, Winchester, VA

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

Regency at Creekside

$700ks - $800ks

Regency at Creekside, Gainesville, VA

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

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

CobbleStone Estates

$400ks - $500ks

CobbleStone Estates, Hagerstown, MD

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

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

Questions? Call us: (540) 452-4199

The Village at Foxfield

$300ks - $500ks

The Village at Foxfield, Middletown, MD

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

Central Parke at Lowes Is...

$300ks - $600ks

Central Parke at Lowes Is..., Sterling, VA

Resale Only | 55+ age-restricted | Built 2003 - 2005 | 181 homes

5 rating (2 reviews)

Potomac Green

$400ks - $800ks

Potomac Green, Ashburn, VA

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

Cross Creek Village

$300ks

Cross Creek Village, Winchester, VA

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

3 rating (2 reviews)

Dunbarton

$300ks - $500ks

Dunbarton, Bristow, VA

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

Heritage Highlands

$300ks - $400ks

Heritage Highlands, Lovettsville, VA

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

Lexington 7

$600ks - $700ks

Lexington 7, Ashburn, VA

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

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

Questions? Call us: (540) 452-4199

The Signature at Broadlan...

$300ks - $400ks

The Signature at Broadlan..., Ashburn, VA

Resale Only | 55+ age-restricted | Built 2018 - 2020 | 45 homes

Carter's Mill

$400ks - $700ks

Carter's Mill, Haymarket, VA

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

1...2

New Suffield Meadows

6708 STREAM VIEW LN, WARRENTON, VA, 2018..., Warrenton, VA 20187

$619,900

3 beds

3 baths

3,701 sq ft

Condo

6708 STREAM VIEW LN, WARRENTON, VA, 2018...

Community: Suffield Meadows

New Regency at Dominion Valley

15508 HAGEN WAY, HAYMARKET, VA, 20169, Haymarket, VA 20169

$929,900

3 beds

3 baths

3,810 sq ft

15508 HAGEN WAY, HAYMARKET, VA, 20169

Community: Regency at Dominion Valley

New Heritage Hunt

13749 HERITAGE VALLEY WAY, GAINESVILLE, ..., Gainesville, VA 20155

$730,000

3 beds

3 baths

2,626 sq ft

13749 HERITAGE VALLEY WAY, GAINESVILLE, ...

Community: Heritage Hunt

New Birchwood at Brambleton

23640 BOLTON CRESCENT TER 403, ASHBURN, ..., Ashburn, VA 20148

$759,900

3 beds

2 baths

1,908 sq ft

Condo

23640 BOLTON CRESCENT TER 403, ASHBURN, ...

Community: Birchwood at Brambleton

New Potomac Green

44480 BLUERIDGE MEADOWS DR, ASHBURN, VA,..., Ashburn, VA 20147

$885,000

3 beds

3 baths

2,817 sq ft

44480 BLUERIDGE MEADOWS DR, ASHBURN, VA,...

Community: Potomac Green

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Questions? Call us: (540) 452-4199

New Potomac Green

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

$760,000

3 beds

3 baths

2,118 sq ft

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

Community: Potomac Green

New Boxwood Villas

3816 FULHAM RD, FREDERICK, MD, 21704, Frederick, MD 21704

$759,900

3 beds

4 baths

3,383 sq ft

3816 FULHAM RD, FREDERICK, MD, 21704

Community: Boxwood Villas

New Regency at Belmont

43927 HURLEYS HUNT TER, ASHBURN, VA, 201..., Ashburn, VA 20147

$1,099,000

3 beds

4 baths

3,255 sq ft

43927 HURLEYS HUNT TER, ASHBURN, VA, 201...

Community: Regency at Belmont

New Bloomfields 55+

2644 BLAZING STAR ST, FREDERICK, MD, 217..., Frederick, MD 21702

$665,990

2 beds

2 baths

2,915 sq ft

2644 BLAZING STAR ST, FREDERICK, MD, 217...

Community: Bloomfields 55+

New Bloomfields 55+

2619 BROADLEAF DR, FREDERICK, MD, 21702, Frederick, MD 21702

$809,990

4 beds

4 baths

4,034 sq ft

2619 BROADLEAF DR, FREDERICK, MD, 21702

Community: Bloomfields 55+

New Bloomfields 55+

2617 BROADLEAF DR, FREDERICK, MD, 21702, Frederick, MD 21702

$779,990

4 beds

4 baths

3,591 sq ft

2617 BROADLEAF DR, FREDERICK, MD, 21702

Community: Bloomfields 55+

New Bloomfields 55+

2615 BROADLEAF DR, FREDERICK, MD, 21702, Frederick, MD 21702

$729,990

3 beds

3 baths

3,357 sq ft

2615 BROADLEAF DR, FREDERICK, MD, 21702

Community: Bloomfields 55+

New Bloomfields 55+

2613 BROADLEAF, FREDERICK, MD, 21702, Frederick, MD 21702

$699,990

3 beds

3 baths

2,915 sq ft

2613 BROADLEAF, FREDERICK, MD, 21702

Community: Bloomfields 55+

New Montebello

21914 HAWKSBILL HIGH CIR 204, STERLING, ..., Sterling, VA 20164

$599,999

2 beds

2 baths

1,419 sq ft

Condo

21914 HAWKSBILL HIGH CIR 204, STERLING, ...

Community: Montebello

New Montebello

21630 HAWKSBILL HIGH CIR 202, STERLING, ..., Sterling, VA 20164

$735,999

3 beds

2 baths

1,940 sq ft

Condo

21630 HAWKSBILL HIGH CIR 202, STERLING, ...

Community: Montebello

New Heritage Hunt

13191 TRIPLE CROWN LOOP, GAINESVILLE, VA..., Gainesville, VA 20155

$785

4 beds

5 baths

4,664 sq ft

13191 TRIPLE CROWN LOOP, GAINESVILLE, VA...

Community: Heritage Hunt

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

Questions? Call us: (540) 452-4199

Trilogy® at Lake Frederick

134 ATLANTIS LN, LAKE FREDERICK, VA, 226..., Lake Frederick, VA 22630

$635,000

3 beds

3 baths

2,173 sq ft

134 ATLANTIS LN, LAKE FREDERICK, VA, 226...

Community: Trilogy® at Lake Frederick

Rosehill Manor Villas

19536 COSMOS ST, HAGERSTOWN, MD, 21742, Hagerstown, MD 21742

$399,900

2 beds

2 baths

1,819 sq ft

19536 COSMOS ST, HAGERSTOWN, MD, 21742

Community: Rosehill Manor Villas

Crestwood Village

5686 CRABAPPLE DR, FREDERICK, MD, 21703, Frederick, MD 21703

$365,000

2 beds

2 baths

1,164 sq ft

5686 CRABAPPLE DR, FREDERICK, MD, 21703

Community: Crestwood Village

The Woodlands of Urbana

3282 PINE NEEDLE CIR 301, FREDERICK, MD,..., Frederick, MD 21704

$450,000

2 beds

2 baths

1,489 sq ft

Condo

3282 PINE NEEDLE CIR 301, FREDERICK, MD,...

Community: The Woodlands of Urbana

Regency at Creekside

6010 TROTTERS POINT LN, GAINESVILLE, VA,..., Gainesville, VA 20155

$1,100,000

3 beds

3 baths

3,969 sq ft

6010 TROTTERS POINT LN, GAINESVILLE, VA,...

Community: Regency at Creekside

Four Seasons at Ashburn Village

21007 ROCKY KNOLL SQ 205, ASHBURN, VA, 2..., Ashburn, VA 20147

$529,900

2 beds

2 baths

1,491 sq ft

Condo

21007 ROCKY KNOLL SQ 205, ASHBURN, VA, 2...

Community: Four Seasons at Ashburn Village

JerMae Estates

4 MAE WAY, THURMONT, MD, 21788, Thurmont, MD 21788

$500,000

3 beds

3 baths

3,073 sq ft

4 MAE WAY, THURMONT, MD, 21788

Community: JerMae Estates

Heritage Hunt

13293 FIELDSTONE WAY, GAINESVILLE, VA, 2..., Gainesville, VA 20155

$724,989

3 beds

3 baths

2,520 sq ft

13293 FIELDSTONE WAY, GAINESVILLE, VA, 2...

Community: Heritage Hunt

Cross Creek Village

203 CRANBERRY CT, WINCHESTER, VA, 22602, Winchester, VA 22602

$389,000

2 beds

2 baths

1,658 sq ft

203 CRANBERRY CT, WINCHESTER, VA, 22602

Community: Cross Creek Village

Rosehill Manor Villas

19601 LAVENDER LN, HAGERSTOWN, MD, 21742, Hagerstown, MD 21742

$374,900

3 beds

2 baths

1,735 sq ft

19601 LAVENDER LN, HAGERSTOWN, MD, 21742

Community: Rosehill Manor Villas

Birchwood at Brambleton

23630 HAVELOCK WALK TER 200, ASHBURN, VA..., Ashburn, VA 20148

$529,990

3 beds

2 baths

1,742 sq ft

Condo

23630 HAVELOCK WALK TER 200, ASHBURN, VA...

Community: Birchwood at Brambleton

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

Questions? Call us: (540) 452-4199

Cedar Meadows

104 POPPY DR, WHITE POST, VA, 22663, White Post, VA 22663

$470,000

3 beds

2 baths

1,633 sq ft

104 POPPY DR, WHITE POST, VA, 22663

Community: Cedar Meadows

Lansdowne Woods of Virginia

19385 CYPRESS RIDGE TER 519, LEESBURG, V..., Leesburg, VA 20176

$325,000

2 beds

2 baths

1,038 sq ft

Condo

19385 CYPRESS RIDGE TER 519, LEESBURG, V...

Community: Lansdowne Woods of Virginia

The Village at Harvest Ridge

407 MIKEY CT, WINCHESTER, VA, 22601, Winchester, VA 22601

$699,900

3 beds

3 baths

3,280 sq ft

407 MIKEY CT, WINCHESTER, VA, 22601

Community: The Village at Harvest Ridge

Heritage Hunt

6840 TRED AVON PL, GAINESVILLE, VA, 2015..., Gainesville, VA 20155

$750,000

3 beds

3 baths

2,626 sq ft

6840 TRED AVON PL, GAINESVILLE, VA, 2015...

Community: Heritage Hunt

Crestwood Village

7006 BASSWOOD RD, FREDERICK, MD, 21703, Frederick, MD 21703

$295,500

2 beds

1 baths

924 sq ft

7006 BASSWOOD RD, FREDERICK, MD, 21703

Community: Crestwood Village

Regency at Dominion Valley

5217 ADDLERFIELD WAY, HAYMARKET, VA, 201..., Haymarket, VA 20169

$824,500

3 beds

3 baths

3,179 sq ft

5217 ADDLERFIELD WAY, HAYMARKET, VA, 201...

Community: Regency at Dominion Valley

Lansdowne Woods of Virginia

19375 CYPRESS RIDGE TER 621, LEESBURG, V..., Leesburg, VA 20176

$449,900

2 beds

2 baths

1,509 sq ft

Condo

19375 CYPRESS RIDGE TER 621, LEESBURG, V...

Community: Lansdowne Woods of Virginia

Dunbarton

9716 SEAFIELD PL, BRISTOW, VA, 20136, Bristow, VA 20136

$675,000

3 beds

3 baths

2,760 sq ft

9716 SEAFIELD PL, BRISTOW, VA, 20136

Community: Dunbarton

Trilogy® at Lake Frederick

124 YELLOW BIRCH, LAKE FREDERICK, VA, 22..., Lake Frederick, VA 22630

$1,199,000

4 beds

5 baths

4,933 sq ft

124 YELLOW BIRCH, LAKE FREDERICK, VA, 22...

Community: Trilogy® at Lake Frederick

Trilogy® at Lake Frederick

122 FOAM FLOWER DR, LAKE FREDERICK, VA, ..., Lake Frederick, VA 22630

$575,000

3 beds

2 baths

1,980 sq ft

122 FOAM FLOWER DR, LAKE FREDERICK, VA, ...

Community: Trilogy® at Lake Frederick

JerMae Estates

5 GEOLEY CT, THURMONT, MD, 21788, Thurmont, MD 21788

$519,999

4 beds

3 baths

2,038 sq ft

5 GEOLEY CT, THURMONT, MD, 21788

Community: JerMae Estates

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

Questions? Call us: (540) 452-4199

Regency at Dominion Valley

15100 HEATHER MILL LN 301, HAYMARKET, VA..., Haymarket, VA 20169

$499,000

3 beds

2 baths

1,833 sq ft

Condo

15100 HEATHER MILL LN 301, HAYMARKET, VA...

Community: Regency at Dominion Valley

Regency at Dominion Valley

5416 ZOYSIA CT, HAYMARKET, VA, 20169, Haymarket, VA 20169

$915,000

4 beds

4 baths

3,962 sq ft

5416 ZOYSIA CT, HAYMARKET, VA, 20169

Community: Regency at Dominion Valley

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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 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 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 621 days. The average price of homes for sale in these communities is approximately $480,419, 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 $620,552, 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

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: May 25, 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

218 homes near Winchester Area

3 beds

3 baths

3,701 sq ft

Condo

3 beds

3 baths

3,810 sq ft

3 beds

3 baths

2,626 sq ft

3 beds

2 baths

1,908 sq ft

Condo

3 beds

3 baths

2,817 sq ft

3 beds

3 baths

2,118 sq ft

3 beds

4 baths

3,383 sq ft

3 beds

4 baths

3,255 sq ft

2 beds

2 baths

2,915 sq ft

4 beds

4 baths

4,034 sq ft

4 beds

4 baths

3,591 sq ft

3 beds

3 baths

3,357 sq ft

3 beds

3 baths

2,915 sq ft

2 beds

2 baths

1,419 sq ft

Condo

3 beds

2 baths

1,940 sq ft

Condo

4 beds

5 baths

4,664 sq ft

3 beds

3 baths

2,173 sq ft

2 beds

2 baths

1,819 sq ft

2 beds

2 baths

1,164 sq ft

2 beds

2 baths

1,489 sq ft

Condo

3 beds

3 baths

3,969 sq ft

2 beds

2 baths

1,491 sq ft

Condo

3 beds

3 baths

3,073 sq ft

3 beds

3 baths