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

219 homes near Winchester Area

Sort by:

Relevance

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

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

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 (3 reviews)

Heritage Hunt

$400ks - $600ks

Heritage Hunt, Gainesville, VA

Resale Only | 55+ age-restricted | Built 1998 - 2009 | 1,863 homes

Willow Run

$500ks - $600ks

Willow Run, Winchester, VA

New Construction | 55+ age-restricted | 300 homes

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

Questions? Call us: (540) 452-4199

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

The Woodlands of Urbana

$500ks - $700ks

The Woodlands of Urbana, Urbana, MD

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

5 rating (1 reviews)

Crestwood Village

$200ks - $500ks

Crestwood Village, Frederick, MD

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

Bloomfields 55+

$700ks - $800ks

Bloomfields 55+, Frederick, MD

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

Rosehill Manor Villas

$300ks

Rosehill Manor Villas, Hagerstown, MD

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

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

Cedar Meadows

$300ks - $400ks

Cedar Meadows, White Post, VA

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

5 rating (2 reviews)

Potomac Green

$400ks - $800ks

Potomac Green, Ashburn, VA

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

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

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

Questions? Call us: (540) 452-4199

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

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

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

The Village at Harvest Ri...

$400ks - $500ks

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

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

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

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

Questions? Call us: (540) 452-4199

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

Regency at Creekside

$700ks - $800ks

Regency at Creekside, Gainesville, VA

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

JerMae Estates

$300ks - $400ks

JerMae Estates, Thurmont, MD

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

Regency at Ashburn

$300ks - $800ks

Regency at Ashburn, Ashburn, VA

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

Lexington 7

$600ks - $700ks

Lexington 7, Ashburn, VA

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

Heritage Highlands

$300ks - $400ks

Heritage Highlands, Lovettsville, VA

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

Albert Courts

$100ks - $200ks

Albert Courts, Thurmont, MD

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

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

Questions? Call us: (540) 452-4199

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

Cross Creek Village

$300ks

Cross Creek Village, Winchester, VA

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

1...2

Lansdowne Woods of Virginia

19375 CYPRESS RIDGE TER 604, LEESBURG, V..., Leesburg, VA 20176

$340,000

2 beds

2 baths

1,038 sq ft

Condo

19375 CYPRESS RIDGE TER 604, LEESBURG, V...

Community: Lansdowne Woods of Virginia

Heritage Hunt

13972 REAL QUITE CT, GAINESVILLE, VA, 20..., Gainesville, VA 20155

$775,000

4 beds

4 baths

3,256 sq ft

13972 REAL QUITE CT, GAINESVILLE, VA, 20...

Community: Heritage Hunt

Liberty Grove

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

$315,000

2 beds

3 baths

1,743 sq ft

Condo

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

Community: Liberty Grove

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

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

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

Questions? Call us: (540) 452-4199

The Flats at Heathcote Village by Del Webb

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

$699,990

3 beds

3 baths

2,625 sq ft

6156 AMBER LN, HAYMARKET, VA, 20169

Community: The Flats at Heathcote Village by Del Webb

The Flats at Heathcote Village by Del Webb

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

$734,990

3 beds

3 baths

3,424 sq ft

6156 AMBER LN 2, HAYMARKET, VA, 20169

Community: The Flats at Heathcote Village by Del Webb

The Flats at Heathcote Village by Del Webb

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

$709,990

3 beds

3 baths

2,763 sq ft

6152 AMBER LN, HAYMARKET, VA, 20169

Community: The Flats at Heathcote Village by Del Webb

The Flats at Heathcote Village by Del Webb

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

$744,990

3 beds

3 baths

3,531 sq ft

6152 AMBER LN 2, HAYMARKET, VA, 20169

Community: The Flats at Heathcote Village by Del Webb

Crestwood Village

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

$329,900

2 beds

2 baths

1,264 sq ft

5738 BOX ELDER CT, FREDERICK, MD, 21703

Community: Crestwood Village

Heritage Hunt

13891 CHELMSFORD DR 110, GAINESVILLE, VA..., Gainesville, VA 20155

$425,000

3 beds

2 baths

1,424 sq ft

Condo

13891 CHELMSFORD DR 110, GAINESVILLE, VA...

Community: Heritage Hunt

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

The Woodlands of Urbana

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

$639,990

3 beds

4 baths

2,276 sq ft

3234 STARLIGHT ST, FREDERICK, MD, 21704

Community: The Woodlands of Urbana

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

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

Heritage Hunt

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

$839,990

4 beds

4 baths

3,761 sq ft

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

Community: Heritage Hunt

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

Questions? Call us: (540) 452-4199

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

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

Lansdowne Woods of Virginia

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

$449,900

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

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

Trilogy® at Lake Frederick

213 GREBE DR, LAKE FREDERICK, VA, 22630, Lake Frederick, VA 22630

$749,990

3 beds

4 baths

3,191 sq ft

213 GREBE DR, LAKE FREDERICK, VA, 22630

Community: Trilogy® at Lake Frederick

Trilogy® at Lake Frederick

110 COTTONTAIL DR, LAKE FREDERICK, VA, 2..., Lake Frederick, VA 22630

$575,000

3 beds

3 baths

2,860 sq ft

110 COTTONTAIL DR, LAKE FREDERICK, VA, 2...

Community: Trilogy® at Lake Frederick

Heritage Hunt

13703 CURRANT LOOP, GAINESVILLE, VA, 201..., Gainesville, VA 20155

$565,000

3 beds

3 baths

2,050 sq ft

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

Community: Heritage Hunt

Willow Run

232 HYDRANGEA WAY, WINCHESTER, VA, 22602, Winchester, VA 22602

$653,990

4 beds

3 baths

2,909 sq ft

232 HYDRANGEA WAY, WINCHESTER, VA, 22602

Community: Willow Run

Willow Run

234 HYDRANGEA WAY, WINCHESTER, VA, 22602, Winchester, VA 22602

$653,990

4 beds

3 baths

2,865 sq ft

234 HYDRANGEA WAY, WINCHESTER, VA, 22602

Community: Willow Run

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

Questions? Call us: (540) 452-4199

Willow Run

249 HYDRANGEA WAY, WINCHESTER, VA, 22602, Winchester, VA 22602

$649,990

4 beds

3 baths

2,712 sq ft

249 HYDRANGEA WAY, WINCHESTER, VA, 22602

Community: Willow Run

Willow Run

125 TRELLIS VIEW LN, WINCHESTER, VA, 226..., Winchester, VA 22602

$459,990

3 beds

2 baths

1,492 sq ft

125 TRELLIS VIEW LN, WINCHESTER, VA, 226...

Community: Willow Run

Willow Run

123 TRELLIS VIEW LN, WINCHESTER, VA, 226..., Winchester, VA 22602

$459,990

3 beds

2 baths

1,492 sq ft

123 TRELLIS VIEW LN, WINCHESTER, VA, 226...

Community: Willow Run

Willow Run

122 TRELLIS VIEW LN, WINCHESTER, VA, 226..., Winchester, VA 22602

$519,990

4 beds

3 baths

2,168 sq ft

122 TRELLIS VIEW LN, WINCHESTER, VA, 226...

Community: Willow Run

Trilogy® at Lake Frederick

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

$384,900

3 beds

3 baths

1,848 sq ft

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

Community: Trilogy® at Lake Frederick

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

Potomac Green

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

$729,000

3 beds

3 baths

2,447 sq ft

20500 CASABLANCA DR, ASHBURN, VA, 20147

Community: Potomac Green

Heritage Hunt

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

$725,000

4 beds

3 baths

3,082 sq ft

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

Community: Heritage Hunt

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

$604,900

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

$410,000

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

$797,540

3 beds

3 baths

2,625 sq ft

6091 AZURITE WAY, HAYMARKET, VA, 20169

Community: The Flats at Heathcote Village by Del Webb

1 2 3 4 5…6

Home
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 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 Trilogy® at Lake Frederick, Cottage Glen, Abrams Chase.

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 614 days. The average price of homes for sale in these communities is approximately $482,668, 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 $631,008, 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

219 homes

Remove Boundaries ×

Map Satellite

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 31, 2026.
This application does not include information on all of the properties available for sale at this time.

Call Us Call Us

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

51 communities near Winchester Area

219 homes near Winchester Area

2 beds

2 baths

1,038 sq ft

Condo

4 beds

4 baths

3,256 sq ft

2 beds

3 baths

1,743 sq ft

Condo

1 beds

2 baths

1,229 sq ft

Condo

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

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

3 beds

4 baths

2,276 sq ft

2 beds

2 baths

1,828 sq ft

3 beds

3 baths

1,816 sq ft

4 beds

4 baths

3,761 sq ft

2 beds

2 baths

1,605 sq ft

3 beds

3 baths

2,252 sq ft

3 beds

2 baths

1,475 sq ft

Condo

3 beds

3 baths

2,457 sq ft

2 beds

3 baths

1,518 sq ft

Condo

3 beds

4 baths

4,213 sq ft

3 beds

4 baths

3,191 sq ft

3 beds

3 baths