Winchester Area, VA 55+ active adult communities & homes for sale - Page 4

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

Cedar Meadows

111 BLUETS DR, WHITE POST, VA, 22663, White Post, VA 22663

$469,900

3 beds

2 baths

1,619 sq ft

111 BLUETS DR, WHITE POST, VA, 22663

Community: Cedar Meadows

Trilogy® at Lake Frederick

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

$629,000

3 beds

3 baths

2,173 sq ft

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

Community: Trilogy® at Lake Frederick

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

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

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

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

Questions? Call us: (540) 452-4199

Lexington Square

44508 LOWESTOFT SQ, ASHBURN, VA, 20147, Ashburn, VA 20147

$784,936

3 beds

3 baths

3,036 sq ft

44508 LOWESTOFT SQ, ASHBURN, VA, 20147

Community: Lexington Square

Lexington 7

$784,936

3 beds

3 baths

3,036 sq ft

44508 LOWESTOFT SQ, ASHBURN, VA, 20147

Community: Lexington 7

Potomac Green

20726 CRESCENT POINTE PL, ASHBURN, VA, 2..., Ashburn, VA 20147

$850,000

3 beds

3 baths

2,798 sq ft

20726 CRESCENT POINTE PL, ASHBURN, VA, 2...

Community: Potomac Green

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

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

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

Robinson Manor

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

$699,000

3 beds

3 baths

2,270 sq ft

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

Community: Robinson Manor

Abrams Chase

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

$515,000

2 beds

2 baths

1,800 sq ft

105 AMBERFIELD CT, WINCHESTER, VA, 22602

Community: Abrams Chase

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

Questions? Call us: (540) 452-4199

Dunbarton

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

$639,999

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

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

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

Trilogy® at Lake Frederick

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

$625,000

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

13170 TRIPLE CROWN LOOP, GAINESVILLE, VA..., Gainesville, VA 20155

$779,900

3 beds

3 baths

2,848 sq ft

13170 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

Heritage Hunt

14025 BREEDERS CUP DR, GAINESVILLE, VA, ..., Gainesville, VA 20155

$699,000

3 beds

3 baths

2,714 sq ft

14025 BREEDERS CUP DR, GAINESVILLE, VA, ...

Community: Heritage Hunt

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

Heritage Hunt

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

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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The Flats at Heathcote Village by Del Webb

5800 MOONSTONE WAY 2, HAYMARKET, VA, 201..., Haymarket, VA 20169

$429,990

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

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

Bloomfields 55+

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

$809,990

3 beds

3 baths

4,034 sq ft

2619 BROADLEAF DR, FREDERICK, MD, 21702

Community: Bloomfields 55+

Bloomfields 55+

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

$779,990

3 beds

3 baths

3,591 sq ft

2617 BROADLEAF DR, FREDERICK, MD, 21702

Community: Bloomfields 55+

Bloomfields 55+

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

$729,990

2 beds

2 baths

3,357 sq ft

2615 BROADLEAF DR, FREDERICK, MD, 21702

Community: Bloomfields 55+

Bloomfields 55+

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

$699,990

2 beds

2 baths

2,915 sq ft

2613 BROADLEAF DR, FREDERICK, MD, 21702

Community: Bloomfields 55+

Potomac Green

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

$850,000

3 beds

3 baths

2,810 sq ft

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

Community: Potomac Green

Regency at Dominion Valley

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

$465,000

2 beds

2 baths

1,551 sq ft

Condo

15110 HEATHER MILL LN 402, HAYMARKET, VA...

Community: Regency at Dominion Valley

Birchwood at Brambleton

23631 HAVELOCK WALK TER 302, ASHBURN, VA..., Ashburn, VA 20148

$449,900

2 beds

2 baths

1,244 sq ft

Condo

23631 HAVELOCK WALK TER 302, 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

Rosehill Manor Villas

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

$374,900

2 beds

2 baths

1,767 sq ft

19604 LAVENDER LN, HAGERSTOWN, MD, 21742

Community: Rosehill Manor Villas

Willow Run

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

$609,990

4 beds

3 baths

2,818 sq ft

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

Community: Willow Run

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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
Instant new home alerts
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 - Page 4

51 communities near Winchester Area

205 homes near Winchester Area

3 beds

2 baths

1,619 sq ft

3 beds

3 baths

2,173 sq ft

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

3,036 sq ft

3 beds

3 baths

3,036 sq ft

3 beds

3 baths

2,798 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

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

1,372 sq ft

Condo

2 beds

2 baths

1,148 sq ft

2 beds

2 baths

2,089 sq ft

3 beds

2 baths

1,748 sq ft

3 beds

2 baths

1,865 sq ft

3 beds

3 baths

2,848 sq ft

3 beds

3 baths

2,714 sq ft

3 beds

2 baths

1,906 sq ft

Condo

4 beds

3 baths

2,126 sq ft

2 beds