Winchester Area, VA 55+ active adult communities & homes for sale - Page 2

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

13703 CURRANT LOOP, GAINESVILLE, VA, 201...

2,168 sq ft

122 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

Trilogy® at Lake Frederick

118 TWINLEAF WAY, LAKE FREDERICK, VA, 22..., Lake Frederick, VA 22630

$399,900

3 beds

3 baths

1,848 sq ft

118 TWINLEAF WAY, LAKE FREDERICK, VA, 22...

Community: Trilogy® at Lake Frederick

Heritage Hunt

6344 AVINGTON PL, GAINESVILLE, VA, 20155, Gainesville, VA 20155

$749,900

3 beds

3 baths

3,495 sq ft

6344 AVINGTON PL, GAINESVILLE, VA, 20155

Community: Heritage Hunt

Four Seasons at Vint Hill

6854 AVERBACH CT, WARRENTON, VA, 20187, Warrenton, VA 20187

$674,980

3 beds

4 baths

4,277 sq ft

6854 AVERBACH CT, WARRENTON, VA, 20187

Community: Four Seasons at Vint Hill

Heritage Hunt

6369 AVINGTON PL, GAINESVILLE, VA, 20155, Gainesville, VA 20155

$790,000

3 beds

3 baths

2,856 sq ft

6369 AVINGTON PL, GAINESVILLE, VA, 20155

Community: Heritage Hunt

Lansdowne Woods of Virginia

19360 MAGNOLIA GROVE SQ 108, LEESBURG, V..., Leesburg, VA 20176

$359,500

2 beds

2 baths

1,170 sq ft

Condo

19360 MAGNOLIA GROVE SQ 108, LEESBURG, V...

Community: Lansdowne Woods of Virginia

Emerald Pointe

19553 TURQUOISE DR V222, HAGERSTOWN, MD,..., Hagerstown, MD 21742

$484,900

2 beds

2 baths

1,850 sq ft

19553 TURQUOISE DR V222, HAGERSTOWN, MD,...

Community: Emerald Pointe

Lansdowne Woods of Virginia

19355 CYPRESS RIDGE TER 422, LEESBURG, V..., Leesburg, VA 20176

$370,000

2 beds

2 baths

1,038 sq ft

Condo

19355 CYPRESS RIDGE TER 422, LEESBURG, V...

Community: Lansdowne Woods of Virginia

Trilogy® at Lake Frederick

121 CHECKERSPOT, LAKE FREDERICK, VA, 226..., Lake Frederick, VA 22630

$425,000

4 beds

4 baths

2,205 sq ft

121 CHECKERSPOT, LAKE FREDERICK, VA, 226...

Community: Trilogy® at Lake Frederick

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

Questions? Call us: (540) 452-4199

Potomac Green

20500 CASABLANCA DR, ASHBURN, VA, 20147, Ashburn, VA 20147

$739,000

3 beds

3 baths

2,447 sq ft

20500 CASABLANCA DR, ASHBURN, VA, 20147

Community: Potomac Green

Lansdowne Woods of Virginia

19375 CYPRESS RIDGE TER 409, LEESBURG, V..., Leesburg, VA 20176

$289,000

1 beds

1 baths

874 sq ft

Condo

19375 CYPRESS RIDGE TER 409, LEESBURG, V...

Community: Lansdowne Woods of Virginia

Heritage Hunt

6230 SETTLERS TRAIL PL, GAINESVILLE, VA,..., Gainesville, VA 20155

$738,000

4 beds

3 baths

3,082 sq ft

6230 SETTLERS TRAIL PL, GAINESVILLE, VA,...

Community: Heritage Hunt

Potomac Green

44367 ADARE MANOR SQ, ASHBURN, VA, 20147, Ashburn, VA 20147

$675,000

2 beds

3 baths

2,060 sq ft

44367 ADARE MANOR SQ, ASHBURN, VA, 20147

Community: Potomac Green

Dunbarton

9709 SEAFIELD PL, BRISTOW, VA, 20136, Bristow, VA 20136

$750,000

4 beds

4 baths

4,435 sq ft

9709 SEAFIELD PL, BRISTOW, VA, 20136

Community: Dunbarton

Birchwood at Brambleton

42970 TRUMAN TER, ASHBURN, VA, 20148, Ashburn, VA 20148

$882,206

3 beds

4 baths

2,742 sq ft

42970 TRUMAN TER, ASHBURN, VA, 20148

Community: Birchwood at Brambleton

Trilogy® at Lake Frederick

123 COWBIRD ST, LAKE FREDERICK, VA, 2263..., Lake Frederick, VA 22630

$640,000

3 beds

3 baths

2,721 sq ft

123 COWBIRD ST, LAKE FREDERICK, VA, 2263...

Community: Trilogy® at Lake Frederick

Trilogy® at Lake Frederick

118 VICEROY WAY, LAKE FREDERICK, VA, 226..., Lake Frederick, VA 22630

$550,000

3 beds

3 baths

2,523 sq ft

118 VICEROY WAY, LAKE FREDERICK, VA, 226...

Community: Trilogy® at Lake Frederick

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

Questions? Call us: (540) 452-4199

Crestwood Village

5661 CRABAPPLE DR, FREDERICK, MD, 21703, Frederick, MD 21703

$435,000

2 beds

2 baths

1,297 sq ft

5661 CRABAPPLE DR, FREDERICK, MD, 21703

Community: Crestwood Village

The Flats at Heathcote Village by Del Webb

6091 AZURITE WAY, HAYMARKET, VA, 20169, Haymarket, VA 20169

$782,540

3 beds

3 baths

2,625 sq ft

6091 AZURITE WAY, HAYMARKET, VA, 20169

Community: The Flats at Heathcote Village by Del Webb

The Flats at Heathcote Village by Del Webb

6093 AZURITE WAY, HAYMARKET, VA, 20169, Haymarket, VA 20169

$820,756

3 beds

4 baths

2,625 sq ft

6093 AZURITE WAY, HAYMARKET, VA, 20169

Community: The Flats at Heathcote Village by Del Webb

The Flats at Heathcote Village by Del Webb

6099 AZURITE WAY, HAYMARKET, VA, 20169, Haymarket, VA 20169

$737,083

3 beds

3 baths

2,763 sq ft

6099 AZURITE WAY, HAYMARKET, VA, 20169

Community: The Flats at Heathcote Village by Del Webb

The Flats at Heathcote Village by Del Webb

5917 SUNSTONE LN, HAYMARKET, VA, 20169, Haymarket, VA 20169

$841,207

4 beds

4 baths

4,034 sq ft

5917 SUNSTONE LN, HAYMARKET, VA, 20169

Community: The Flats at Heathcote Village by Del Webb

Lansdowne Woods of Virginia

19385 CYPRESS RIDGE TER 508, LEESBURG, V..., Leesburg, VA 20176

$379,900

2 beds

2 baths

1,196 sq ft

Condo

19385 CYPRESS RIDGE TER 508, LEESBURG, V...

Community: Lansdowne Woods of Virginia

CobbleStone Estates

9724 COBBLE STONE CT 58, HAGERSTOWN, MD,..., Hagerstown, MD 21740

$459,900

2 beds

2 baths

2,220 sq ft

9724 COBBLE STONE CT 58, HAGERSTOWN, MD,...

Community: CobbleStone Estates

Trilogy® at Lake Frederick

101 TROUT LILY DR, LAKE FREDERICK, VA, 2..., Lake Frederick, VA 22630

$400,000

4 beds

4 baths

2,327 sq ft

101 TROUT LILY DR, LAKE FREDERICK, VA, 2...

Community: Trilogy® at Lake Frederick

The Retreat at Poland Hill

25612 PRESTON PARK TER, CHANTILLY, VA, 2..., Chantilly, VA 20152

$755,000

3 beds

3 baths

2,410 sq ft

25612 PRESTON PARK TER, CHANTILLY, VA, 2...

Community: The Retreat at Poland Hill

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

Questions? Call us: (540) 452-4199

Emerald Pointe

13301 MARQUISE DR, HAGERSTOWN, MD, 21742, Hagerstown, MD 21742

$419,900

2 beds

2 baths

1,726 sq ft

13301 MARQUISE DR, HAGERSTOWN, MD, 21742

Community: Emerald Pointe

Trilogy® at Lake Frederick

105 CABBAGE WHITE DR, LAKE FREDERICK, VA..., Lake Frederick, VA 22630

$659,000

3 beds

4 baths

2,910 sq ft

105 CABBAGE WHITE DR, LAKE FREDERICK, VA...

Community: Trilogy® at Lake Frederick

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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 2

51 communities near Winchester Area

205 homes near Winchester Area

3 beds

4 baths

3,191 sq ft

3 beds

3 baths

2,860 sq ft

3 beds

3 baths

4,629 sq ft

4 beds

3 baths

2,341 sq ft

3 beds

3 baths

2,050 sq ft

4 beds

3 baths

2,909 sq ft

4 beds

3 baths

2,865 sq ft

4 beds

3 baths

2,712 sq ft

4 beds

3 baths

2,168 sq ft

3 beds

2 baths

1,492 sq ft

4 beds

3 baths

2,168 sq ft

3 beds

2 baths

1,492 sq ft

4 beds

3 baths

2,168 sq ft

3 beds

3 baths

1,848 sq ft

3 beds

3 baths

3,495 sq ft

3 beds

4 baths

4,277 sq ft

3 beds

3 baths

2,856 sq ft

2 beds

2 baths

1,170 sq ft

Condo

2 beds

2 baths

1,850 sq ft

2 beds

2 baths

1,038 sq ft

Condo

4 beds

4 baths

2,205 sq ft

3 beds

3 baths

2,447 sq ft

1 beds

1 baths

874 sq ft

Condo

4 beds

3 baths

3,082 sq ft

2 beds

3 baths