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

229 homes near Winchester Area

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5 rating (2 reviews)

Trilogy® at Lake Frederic...

$400ks - $900ks

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

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

The Woodlands of Urbana

$500ks - $700ks

The Woodlands of Urbana, Urbana, MD

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

Emerald Pointe

$300ks - $500ks

Emerald Pointe, Hagerstown, MD

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

Willow Run

$500ks - $600ks

Willow Run, Winchester, VA

New Construction | 55+ age-restricted | 300 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

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

Rosehill Manor Villas

$300ks

Rosehill Manor Villas, Hagerstown, MD

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

Winchester Landing

$300ks - $400ks

Winchester Landing, Winchester, VA

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

Montebello

$300ks - $600ks

Montebello, Sterling, VA

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

5 rating (2 reviews)

Potomac Green

$400ks - $800ks

Potomac Green, Ashburn, VA

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

3 rating (2 reviews)

Dunbarton

$300ks - $500ks

Dunbarton, Bristow, VA

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

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

Questions? Call us: (540) 452-4199

5 rating (1 reviews)

Gatherings at Wellington

$300ks - $400ks

Gatherings at Wellington, Manassas, VA

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

5 rating (1 reviews)

Willow Lawn Cottages

$300ks

Willow Lawn Cottages, Winchester, VA

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

Cadence at Lansdowne

$600ks

Cadence at Lansdowne, Lansdowne, VA

Resale Only | 55+ age-restricted | Built 2020 - 2024 | 74 homes

Regency at Belmont

$600ks - $900ks

Regency at Belmont, Ashburn, VA

New Construction | 55+ age-restricted | Built 2021 - present | 145 homes

Suffield Meadows

$400ks

Suffield Meadows, Warrenton, VA

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

Ballenger Run

$300ks - $400ks

Ballenger Run, Frederick, MD

Resale Only | 55+ age-restricted | Built 2019 - 2020 | 36 homes

5 rating (1 reviews)

Crestwood Village

$200ks - $500ks

Crestwood Village, Frederick, MD

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

Liberty Grove

$200ks - $300ks

Liberty Grove, Manassas, VA

Resale Only | 55+ age-restricted | Built 2005 - 2005 | 61 homes

The Signature at Broadlan...

$300ks - $400ks

The Signature at Broadlan..., Ashburn, VA

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

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

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

Questions? Call us: (540) 452-4199

Gatherings at Potomac Sta...

$400ks - $500ks

Gatherings at Potomac Sta..., Leesburg, VA

New Construction | 55+ age-restricted | Built 2023 - 2024 | 55 homes

JerMae Estates

$300ks - $400ks

JerMae Estates, Thurmont, MD

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

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

The Village at Foxfield

$300ks - $500ks

The Village at Foxfield, Middletown, MD

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

Cedar Meadows

$300ks - $400ks

Cedar Meadows, White Post, VA

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

Cross Creek Village

$300ks

Cross Creek Village, Winchester, VA

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

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

Questions? Call us: (540) 452-4199

Carter's Mill

$400ks - $700ks

Carter's Mill, Haymarket, VA

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

Abrams Chase

$400ks - $500ks

Abrams Chase, Winchester, VA

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

1...2

Cindy Certified

672 ARMSTRONG AVE, HAGERSTOWN, MD, 21740, Hagerstown, MD 21740

$385,000

4 beds

2 baths

1,705 sq ft

672 ARMSTRONG AVE, HAGERSTOWN, MD, 21740

Emerald Pointe

19419 AMETHYST DR, HAGERSTOWN, MD, 21742, Hagerstown, MD 21742

$379,000

2 beds

2 baths

2,394 sq ft

19419 AMETHYST DR, HAGERSTOWN, MD, 21742

Community: Emerald Pointe

Crestwood Village

5603 HONEYSUCKLE CT, FREDERICK, MD, 2170..., Frederick, MD 21703

$412,000

2 beds

1 baths

1,297 sq ft

5603 HONEYSUCKLE CT, FREDERICK, MD, 2170...

Community: Crestwood Village

Willow Lawn Cottages

1826 KERSHAW LN, WINCHESTER, VA, 22601, Winchester, VA 22601

$420,000

2 beds

2 baths

1,431 sq ft

1826 KERSHAW LN, WINCHESTER, VA, 22601

Community: Willow Lawn Cottages

Trilogy® at Lake Frederick

105 FRITILLARY CT, LAKE FREDERICK, VA, 2..., Lake Frederick, VA 22630

$425,000

3 beds

4 baths

1,888 sq ft

105 FRITILLARY CT, LAKE FREDERICK, VA, 2...

Community: Trilogy® at Lake Frederick

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

Questions? Call us: (540) 452-4199

Montebello

21630 HAWKSBILL HIGH CIR 204, STERLING, ..., Sterling, VA 20164

$527,590

2 beds

2 baths

1,640 sq ft

Condo

21630 HAWKSBILL HIGH CIR 204, STERLING, ...

Community: Montebello

Heritage Hunt

13886 CRABTREE WAY, GAINESVILLE, VA, 201..., Gainesville, VA 20155

$899,900

3 beds

4 baths

3,590 sq ft

13886 CRABTREE WAY, GAINESVILLE, VA, 201...

Community: Heritage Hunt

The Flats at Heathcote Village by Del Webb

5800 MOONSTONE WAY 203, HAYMARKET, VA, 2..., Haymarket, VA 20169

$515,005

2 beds

2 baths

1,445 sq ft

Condo

5800 MOONSTONE WAY 203, HAYMARKET, VA, 2...

Community: The Flats at Heathcote Village by Del Webb

The Flats at Heathcote Village by Del Webb

5800 MOONSTONE WAY 202, HAYMARKET, VA, 2..., Haymarket, VA 20169

$627,140

3 beds

2 baths

1,850 sq ft

Condo

5800 MOONSTONE WAY 202, HAYMARKET, VA, 2...

Community: The Flats at Heathcote Village by Del Webb

The Flats at Heathcote Village by Del Webb

5800 MOONSTONE WAY 104, HAYMARKET, VA, 2..., Haymarket, VA 20169

$456,065

$660,000

3 beds

2 baths

1,972 sq ft

Condo

23639 GOLDEN EMBERS SQ 302, ASHBURN, VA,...

Community: Birchwood at Brambleton

Cindy Certified

9910 ROULETTE DR, HAGERSTOWN, MD, 21740, Hagerstown, MD 21740

$380,000

3 beds

2 baths

1,527 sq ft

9910 ROULETTE DR, HAGERSTOWN, MD, 21740

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

Questions? Call us: (540) 452-4199

The Village at Freedom Hills

13862 PATRIOT WAY, HAGERSTOWN, MD, 21740, Hagerstown, MD 21740

$475,000

4 beds

2 baths

3,107 sq ft

13862 PATRIOT WAY, HAGERSTOWN, MD, 21740

Community: The Village at Freedom Hills

Trilogy® at Lake Frederick

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

$800,000

3 beds

4 baths

3,604 sq ft

117 MALLARD DR, LAKE FREDERICK, VA, 2263...

Community: Trilogy® at Lake Frederick

Heritage Hunt

6845 SADDLE RUN WAY, GAINESVILLE, VA, 20..., Gainesville, VA 20155

$739,000

4 beds

3 baths

2,068 sq ft

6845 SADDLE RUN WAY, GAINESVILLE, VA, 20...

Community: Heritage Hunt

Trilogy® at Lake Frederick

111 SWITCHGRASS WAY, LAKE FREDERICK, VA,..., Lake Frederick, VA 22630

$599,000

3 beds

3 baths

2,530 sq ft

111 SWITCHGRASS WAY, LAKE FREDERICK, VA,...

Community: Trilogy® at Lake Frederick

Ballenger Run

5307 CRAPE MYRTLE DR, FREDERICK, MD, 217..., Frederick, MD 21703

$529,900

3 beds

4 baths

2,669 sq ft

5307 CRAPE MYRTLE DR, FREDERICK, MD, 217...

Community: Ballenger Run

Lansdowne Woods of Virginia

19385 CYPRESS RIDGE TER 903, LEESBURG, V..., Leesburg, VA 20176

$439,900

2 beds

2 baths

1,509 sq ft

Condo

19385 CYPRESS RIDGE TER 903, LEESBURG, V...

Community: Lansdowne Woods of Virginia

Cindy Certified

6773 AZALEA GARDEN LN, HAYMARKET, VA, 20..., Haymarket, VA 20169

$785,000

3 baths

2,118 sq ft

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

Community: Potomac Green

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

Questions? Call us: (540) 452-4199

Cindy Certified

22127 HEADWATER TER 400, ASHBURN, VA, 20..., Ashburn, VA 20148

$920,000

3 beds

3 baths

2,217 sq ft

Condo

22127 HEADWATER TER 400, ASHBURN, VA, 20...

Ballenger Run

5311 CRAPE MYRTLE DR, FREDERICK, MD, 217..., Frederick, MD 21703

$500,000

3 beds

4 baths

2,868 sq ft

5311 CRAPE MYRTLE DR, FREDERICK, MD, 217...

Community: Ballenger Run

Cadence at Lansdowne

43865 CASTAWAY CAY TER, LEESBURG, VA, 20..., Leesburg, VA 20176

$815,000

3 beds

3 baths

3,868 sq ft

43865 CASTAWAY CAY TER, LEESBURG, VA, 20...

Community: Cadence at Lansdowne

Birchwood at Brambleton

23600 RAYTOWN TER, ASHBURN, VA, 20148, Ashburn, VA 20148

$846,046

3 beds

4 baths

2,742 sq ft

23600 RAYTOWN TER, ASHBURN, VA, 20148

Community: Birchwood at Brambleton

The Flats at Heathcote Village by Del Webb

5928 SUNSTONE LN, HAYMARKET, VA, 20169, Haymarket, VA 20169

$789,871

3 beds

4 baths

2,763 sq ft

5928 SUNSTONE LN, HAYMARKET, VA, 20169

Community: The Flats at Heathcote Village by Del Webb

Winchester Landing

120 GABRIEL CT, WINCHESTER, VA, 22602, Winchester, VA 22602

$499,900

3 beds

3 baths

2,072 sq ft

120 GABRIEL CT, WINCHESTER, VA, 22602

Community: Winchester Landing

Montebello

21630 HAWKSBILL HIGH CIR 405, STERLING, ..., Sterling, VA 20164

$520,000

2 beds

2 baths

1,296 sq ft

Condo

21630 HAWKSBILL HIGH CIR 405, STERLING, ...

Community: Montebello

The Woodlands of Urbana

3264 STARLIGHT ST, FREDERICK, MD, 21704, Frederick, MD 21704

$510,000

3 beds

3 baths

1,817 sq ft

3264 STARLIGHT ST, FREDERICK, MD, 21704

Community: The Woodlands of Urbana

Cadence at Lansdowne

43899 SIREN SONG TER, LEESBURG, VA, 2017..., Leesburg, VA 20176

$785,000

3 beds

4 baths

2,780 sq ft

43899 SIREN SONG TER, LEESBURG, VA, 2017...

Community: Cadence at Lansdowne

Lansdowne Woods of Virginia

19375 CYPRESS RIDGE TER 404, LEESBURG, V..., Leesburg, VA 20176

$330,000

2 beds

2 baths

1,038 sq ft

Condo

19375 CYPRESS RIDGE TER 404, LEESBURG, V...

Community: Lansdowne Woods of Virginia

Lansdowne Woods of Virginia

19385 CYPRESS RDG 515, LEESBURG, VA, 201..., Leesburg, VA 20176

$490,000

3 beds

2 baths

1,475 sq ft

Condo

19385 CYPRESS RDG 515, LEESBURG, VA, 201...

Community: Lansdowne Woods of Virginia

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

Questions? Call us: (540) 452-4199

Heritage Hunt

13484 FIELDSTONE WAY, GAINESVILLE, VA, 2..., Gainesville, VA 20155

$644,990

2 beds

2 baths

2,128 sq ft

13484 FIELDSTONE WAY, GAINESVILLE, VA, 2...

Community: Heritage Hunt

Dunbarton

12028 RUTHERGLEN PL, BRISTOW, VA, 20136, Bristow, VA 20136

$750,000

4 beds

3 baths

3,754 sq ft

12028 RUTHERGLEN PL, BRISTOW, VA, 20136

Community: Dunbarton

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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 Cottage Glen, Trilogy® at Lake Frederick, Willow Run.

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, Cottage Glen is a gated communities with 25 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 620 days. The average price of homes for sale in these communities is approximately $480,385, 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 $625,881, while homes in Cottage Glen average around $464,750.

Want to learn more about 55+ communities in the Winchester Area?

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229 homes

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© 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: Sep 06, 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

229 homes near Winchester Area

4 beds

2 baths

1,705 sq ft

2 beds

2 baths

2,394 sq ft

2 beds

1 baths

1,297 sq ft

2 beds

2 baths

1,431 sq ft

3 beds

4 baths

1,888 sq ft

2 beds

2 baths

1,640 sq ft

Condo

3 beds

4 baths

3,590 sq ft

2 beds

2 baths

1,445 sq ft

Condo

3 beds

2 baths

1,850 sq ft

Condo

2 beds

2 baths

1,345 sq ft

Condo

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

2 baths

1,972 sq ft

Condo

3 beds

2 baths

1,527 sq ft

4 beds

2 baths

3,107 sq ft

3 beds

4 baths

3,604 sq ft

4 beds

3 baths

2,068 sq ft

3 beds

3 baths

2,530 sq ft

3 beds

4 baths

2,669 sq ft

2 beds

2 baths

1,509 sq ft

Condo

3 beds

3 baths

1,927 sq ft

3 beds

3 baths