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

205 homes near Winchester Area

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5 rating (2 reviews)

Trilogy® at Lake Frederic...

- $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

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

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

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

Questions? Call us: (540) 452-4199

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

Emerald Pointe

$300ks - $500ks

Emerald Pointe, Hagerstown, MD

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

5 rating (2 reviews)

Potomac Green

$400ks - $800ks

Potomac Green, Ashburn, VA

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

The Woodlands of Urbana

$500ks - $700ks

The Woodlands of Urbana, Urbana, MD

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

Bloomfields 55+

$700ks - $800ks

Bloomfields 55+, Frederick, MD

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

5 rating (1 reviews)

Gatherings at Wellington

$300ks - $400ks

Gatherings at Wellington, Manassas, VA

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

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

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

Questions? Call us: (540) 452-4199

5 rating (1 reviews)

Crestwood Village

$200ks - $500ks

Crestwood Village, Frederick, MD

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

Winchester Landing

$300ks - $400ks

Winchester Landing, Winchester, VA

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

Robinson Manor

$600ks - $700ks

Robinson Manor, Gainesville, VA

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

Lexington Square

$800ks - $1Ms

Lexington Square, Ashburn, VA

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

Montebello

$500ks - $900ks

Montebello, Sterling, VA

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

Woodbrook Village

$200ks - $300ks

Woodbrook Village, Winchester, VA

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

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

Questions? Call us: (540) 452-4199

The Village at Harvest Ri...

$400ks - $500ks

The Village at Harvest Ri..., Winchester, VA

Resale Only | 55+ age-restricted | Built 2005 - 2016 | 82 homes

Cross Creek Village

$300ks

Cross Creek Village, Winchester, VA

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

Cedar Meadows

$300ks - $400ks

Cedar Meadows, White Post, VA

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

Regency at Ashburn

$300ks - $800ks

Regency at Ashburn, Ashburn, VA

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

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+ communities in Winchester Area? 55places can help!

Questions? Call us: (540) 452-4199

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

Cottage Glen

$400ks

Cottage Glen, Winchester, VA

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

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

Abrams Chase

$400ks - $500ks

Abrams Chase, Winchester, VA

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

The Village at Foxfield

$300ks - $500ks

The Village at Foxfield, Middletown, MD

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

Boxwood Villas

$500ks - $600ks

Boxwood Villas, Urbana, MD

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

Suffield Meadows

$400ks

Suffield Meadows, Warrenton, VA

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

Heritage Highlands

$300ks - $400ks

Heritage Highlands, Lovettsville, VA

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

JerMae Estates

$300ks - $400ks

JerMae Estates, Thurmont, MD

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

1...2

New Liberty Grove

8600 LIBERTY TRL 204, MANASSAS, VA, 2011..., Manassas, VA 20110

$322,700

2 beds

3 baths

1,743 sq ft

Condo

8600 LIBERTY TRL 204, MANASSAS, VA, 2011...

Community: Liberty Grove

New Heritage Hunt

6907 BROADLEAF TER, GAINESVILLE, VA, 201..., Gainesville, VA 20155

$775,000

3 beds

3 baths

2,653 sq ft

6907 BROADLEAF TER, GAINESVILLE, VA, 201...

Community: Heritage Hunt

New Birchwood at Brambleton

23665 HAVELOCK WALK TER 406, ASHBURN, VA..., Ashburn, VA 20148

$525,000

1 beds

2 baths

1,229 sq ft

Condo

23665 HAVELOCK WALK TER 406, ASHBURN, VA...

Community: Birchwood at Brambleton

New Potomac Green

44351 OAKMONT MANOR SQ, ASHBURN, VA, 201..., Ashburn, VA 20147

$675,000

2 beds

3 baths

2,060 sq ft

44351 OAKMONT MANOR SQ, ASHBURN, VA, 201...

Community: Potomac Green

New Potomac Green

44435 CRUDEN BAY DR, ASHBURN, VA, 20147, Ashburn, VA 20147

$725,000

3 beds

3 baths

2,255 sq ft

44435 CRUDEN BAY DR, 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

New The Retreat at Poland Hill

25614 PRESTON PARK TER, CHANTILLY, VA, 2..., Chantilly, VA 20152

$785,000

3 beds

3 baths

2,450 sq ft

25614 PRESTON PARK TER, CHANTILLY, VA, 2...

Community: The Retreat at Poland Hill

New The Flats at Heathcote Village by Del Webb

6156 AMBER LN, HAYMARKET, VA, 20169, Haymarket, VA 20169

$684,990

3 beds

3 baths

2,625 sq ft

6156 AMBER LN, HAYMARKET, VA, 20169

Community: The Flats at Heathcote Village by Del Webb

New The Flats at Heathcote Village by Del Webb

6156 AMBER LN 2, HAYMARKET, VA, 20169, Haymarket, VA 20169

$719,990

3 beds

3 baths

3,424 sq ft

6156 AMBER LN 2, HAYMARKET, VA, 20169

Community: The Flats at Heathcote Village by Del Webb

New The Flats at Heathcote Village by Del Webb

6152 AMBER LN, HAYMARKET, VA, 20169, Haymarket, VA 20169

$694,990

3 beds

3 baths

2,763 sq ft

6152 AMBER LN, HAYMARKET, VA, 20169

Community: The Flats at Heathcote Village by Del Webb

New The Flats at Heathcote Village by Del Webb

6152 AMBER LN 2, HAYMARKET, VA, 20169, Haymarket, VA 20169

$729,990

3 beds

3 baths

3,531 sq ft

6152 AMBER LN 2, HAYMARKET, VA, 20169

Community: The Flats at Heathcote Village by Del Webb

New Regency at Creekside

6198 CHANCELLORSVILLE DR, GAINESVILLE, V..., Gainesville, VA 20155

$1,075,000

3 beds

3 baths

3,247 sq ft

6198 CHANCELLORSVILLE DR, GAINESVILLE, V...

Community: Regency at Creekside

New Crestwood Village

5738 BOX ELDER CT, FREDERICK, MD, 21703, Frederick, MD 21703

$336,000

2 beds

2 baths

1,264 sq ft

5738 BOX ELDER CT, FREDERICK, MD, 21703

Community: Crestwood Village

New Heritage Hunt

13891 CHELMSFORD DR, GAINESVILLE, VA, 20..., Gainesville, VA 20155

$435,000

3 beds

2 baths

1,424 sq ft

Condo

13891 CHELMSFORD DR, GAINESVILLE, VA, 20...

Community: Heritage Hunt

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

Questions? Call us: (540) 452-4199

New Cedar Meadows

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

$475,000

3 beds

2 baths

1,493 sq ft

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

Community: Cedar Meadows

New Heritage Hunt

6828 DERBY RUN WAY, GAINESVILLE, VA, 201..., Gainesville, VA 20155

$745,000

4 beds

3 baths

2,270 sq ft

6828 DERBY RUN WAY, GAINESVILLE, VA, 201...

Community: Heritage Hunt

New The Woodlands of Urbana

3234 STARLIGHT ST, FREDERICK, MD, 21704, Frederick, MD 21704

$649,990

3 beds

4 baths

2,276 sq ft

3234 STARLIGHT ST, FREDERICK, MD, 21704

Community: The Woodlands of Urbana

New Potomac Green

44348 SUNSET MAPLE DR, ASHBURN, VA, 2014..., Ashburn, VA 20147

$649,999

2 beds

3 baths

2,060 sq ft

44348 SUNSET MAPLE DR, ASHBURN, VA, 2014...

Community: Potomac Green

New Potomac Green

44345 SUNSET MAPLE DR, ASHBURN, VA, 2014..., Ashburn, VA 20147

$749,999

2 beds

2 baths

1,591 sq ft

44345 SUNSET MAPLE DR, ASHBURN, VA, 2014...

Community: Potomac Green

New The Village at Harvest Ridge

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

$629,900

3 beds

2 baths

2,834 sq ft

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

Community: The Village at Harvest Ridge

New Trilogy® at Lake Frederick

104 GROSBEAK CT, LAKE FREDERICK, VA, 226..., Lake Frederick, VA 22630

$637,800

3 beds

3 baths

2,933 sq ft

104 GROSBEAK CT, LAKE FREDERICK, VA, 226...

Community: Trilogy® at Lake Frederick

New CobbleStone Estates

9723 COBBLE STONE CT, HAGERSTOWN, MD, 21..., Hagerstown, MD 21740

$439,900

2 beds

2 baths

1,828 sq ft

9723 COBBLE STONE CT, HAGERSTOWN, MD, 21...

Community: CobbleStone Estates

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

Questions? Call us: (540) 452-4199

New Heritage Hunt

13520 NORWICK PL, GAINESVILLE, VA, 20155, Gainesville, VA 20155

$700,000

3 beds

3 baths

2,153 sq ft

13520 NORWICK PL, GAINESVILLE, VA, 20155

Community: Heritage Hunt

New The Woodlands of Urbana

3225 THORNAPPLE DR, FREDERICK, MD, 21704, Frederick, MD 21704

$580,000

3 beds

3 baths

1,816 sq ft

3225 THORNAPPLE DR, FREDERICK, MD, 21704

Community: The Woodlands of Urbana

New Heritage Hunt

6852 TRED AVON PL, GAINESVILLE, VA, 2015..., Gainesville, VA 20155

$850,600

4 beds

4 baths

3,761 sq ft

6852 TRED AVON PL, GAINESVILLE, VA, 2015...

Community: Heritage Hunt

New Potomac Green

20598 CRESCENT POINTE PL, ASHBURN, VA, 2..., Ashburn, VA 20147

$740,000

2 beds

2 baths

1,605 sq ft

20598 CRESCENT POINTE PL, ASHBURN, VA, 2...

Community: Potomac Green

New The Highlands at Blue Ridge Shadows

48 HICKORY SHAFT CT, FRONT ROYAL, VA, 22..., Front Royal, VA 22630

$550,000

3 beds

2 baths

1,763 sq ft

48 HICKORY SHAFT CT, FRONT ROYAL, VA, 22...

Community: The Highlands at Blue Ridge Shadows

New Ballenger Run

6443 AUTUMN OLIVE DR, FREDERICK, MD, 217..., Frederick, MD 21703

$519,900

3 beds

3 baths

2,252 sq ft

6443 AUTUMN OLIVE DR, FREDERICK, MD, 217...

Community: Ballenger Run

New Lansdowne Woods of Virginia

19355 CYPRESS RIDGE TER 219, LEESBURG, V..., Leesburg, VA 20176

$470,000

2 beds

2 baths

1,500 sq ft

Condo

19355 CYPRESS RIDGE TER 219, LEESBURG, V...

Community: Lansdowne Woods of Virginia

New Heritage Hunt

13700 FIELDSTONE WAY, GAINESVILLE, VA, 2..., Gainesville, VA 20155

$889,000

4 beds

4 baths

4,388 sq ft

13700 FIELDSTONE WAY, GAINESVILLE, VA, 2...

Community: Heritage Hunt

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

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Lansdowne Woods of Virginia

19350 MAGNOLIA GROVE SQ 403, LEESBURG, V..., Leesburg, VA 20176

$395,000

2 beds

2 baths

1,168 sq ft

Condo

19350 MAGNOLIA GROVE SQ 403, LEESBURG, V...

Community: Lansdowne Woods of Virginia

Birchwood at Brambleton

42920 FIREFLY SONATA TER 203, ASHBURN, V..., Ashburn, VA 20148

$585,000

3 beds

2 baths

1,712 sq ft

Condo

42920 FIREFLY SONATA TER 203, ASHBURN, V...

Community: Birchwood at Brambleton

Dunbarton

9684 CRAIGHILL DR, BRISTOW, VA, 20136, Bristow, VA 20136

$624,900

3 beds

2 baths

2,314 sq ft

9684 CRAIGHILL DR, BRISTOW, VA, 20136

Community: Dunbarton

Lansdowne Woods of Virginia

19375 CYPRESS RIDGE TER 1111, LEESBURG, ..., Leesburg, VA 20176

$525,000

3 beds

2 baths

1,475 sq ft

Condo

19375 CYPRESS RIDGE TER 1111, LEESBURG, ...

Community: Lansdowne Woods of Virginia

Trilogy® at Lake Frederick

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

$749,990

3 beds

3 baths

2,457 sq ft

104 RHODODENDRON CT, LAKE FREDERICK, VA,...

Community: Trilogy® at Lake Frederick

Liberty Grove

8610 LIBERTY TRL 305, MANASSAS, VA, 2011..., Manassas, VA 20110

$364,900

2 beds

3 baths

1,518 sq ft

Condo

8610 LIBERTY TRL 305, MANASSAS, VA, 2011...

Community: Liberty Grove

Vistas at Lansdowne

19400 LANSDOWNE WOODS BLVD 101, LEESBURG..., Leesburg, VA 20176

$670,000

2 beds

2 baths

2,041 sq ft

Condo

19400 LANSDOWNE WOODS BLVD 101, LEESBURG...

Community: Vistas at Lansdowne

Trilogy® at Lake Frederick

121 MILKWEED, LAKE FREDERICK, VA, 22630, Lake Frederick, VA 22630

$879,900

3 beds

4 baths

4,213 sq ft

121 MILKWEED, LAKE FREDERICK, VA, 22630

Community: Trilogy® at Lake Frederick

Birchwood at Brambleton

23608 HAVELOCK WALK TER, ASHBURN, VA, 20..., Ashburn, VA 20148

$569,999

3 beds

3 baths

2,516 sq ft

Condo

23608 HAVELOCK WALK TER, ASHBURN, VA, 20...

Community: Birchwood at Brambleton

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

Questions? Call us: (540) 452-4199

Regency at Ashburn

44589 YORK CREST TER 300, ASHBURN, VA, 2..., Ashburn, VA 20147

$615,000

3 beds

2 baths

1,886 sq ft

Condo

44589 YORK CREST TER 300, ASHBURN, VA, 2...

Community: Regency at Ashburn

Heritage Hunt

6318 RETRIEVER LN, GAINESVILLE, VA, 2015..., Gainesville, VA 20155

$550,000

3 beds

3 baths

1,953 sq ft

6318 RETRIEVER LN, GAINESVILLE, VA, 2015...

Community: Heritage Hunt

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Virginia
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?

Call us: (540) 452-4199

205 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: Apr 11, 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

205 homes near Winchester Area

2 beds

3 baths

1,743 sq ft

Condo

3 beds

3 baths

2,653 sq ft

1 beds

2 baths

1,229 sq ft

Condo

2 beds

3 baths

2,060 sq ft

3 beds

3 baths

2,255 sq ft

3 beds

3 baths

2,450 sq ft

3 beds

3 baths

2,625 sq ft

3 beds

3 baths

3,424 sq ft

3 beds

3 baths

2,763 sq ft

3 beds

3 baths

3,531 sq ft

3 beds

3 baths

3,247 sq ft

2 beds

2 baths

1,264 sq ft

3 beds

2 baths

1,424 sq ft

Condo

3 beds

2 baths

1,493 sq ft

4 beds

3 baths

2,270 sq ft

3 beds

4 baths

2,276 sq ft

2 beds

3 baths

2,060 sq ft

2 beds

2 baths

1,591 sq ft

3 beds

2 baths

2,834 sq ft

3 beds

3 baths

2,933 sq ft

2 beds

2 baths

1,828 sq ft

3 beds

3 baths

2,153 sq ft

3 beds

3 baths

1,816 sq ft

4 beds

4 baths

3,761 sq ft

2 beds

2 baths