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

51 communities near Winchester Area

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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

5 rating (2 reviews)

Trilogy® at Lake Frederic...

$400ks - $1Ms

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

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

5 rating (3 reviews)

Heritage Hunt

$400ks - $600ks

Heritage Hunt, Gainesville, VA

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

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

The Village at Freedom Hi...

$300ks

The Village at Freedom Hi..., Hagerstown, MD

New and Resale | 55+ age-restricted | Built 2007 - present | 66 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

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.

5 rating (1 reviews)

Willow Lawn Cottages

$300ks

Willow Lawn Cottages, Winchester, VA

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

Rosehill Manor Villas

$300ks

Rosehill Manor Villas, Hagerstown, MD

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

3 rating (2 reviews)

Dunbarton

$300ks - $500ks

Dunbarton, Bristow, VA

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

5 rating (2 reviews)

Potomac Green

$400ks - $800ks

Potomac Green, Ashburn, VA

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

Regency at Belmont

$600ks - $900ks

Regency at Belmont, Ashburn, VA

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

Winchester Landing

$300ks - $400ks

Winchester Landing, Winchester, VA

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

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

Questions? Call us: (540) 452-4199

Willow Run

$500ks - $600ks

Willow Run, Winchester, VA

New Construction | 55+ age-restricted | 300 homes

Cadence at Lansdowne

$600ks

Cadence at Lansdowne, Lansdowne, VA

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

Heritage Highlands

$300ks - $400ks

Heritage Highlands, Lovettsville, VA

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

Emerald Pointe

$300ks - $500ks

Emerald Pointe, Hagerstown, MD

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

Montebello

$300ks - $600ks

Montebello, Sterling, VA

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

Liberty Grove

$200ks - $300ks

Liberty Grove, Manassas, VA

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

Suffield Meadows

$400ks

Suffield Meadows, Warrenton, VA

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

Cedar Meadows

$300ks - $400ks

Cedar Meadows, White Post, VA

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

Vistas at Lansdowne

$800ks

Vistas at Lansdowne, Lansdowne, VA

Resale Only | 55+ age-restricted | Built 2015 - 2020 | 120 homes

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

Questions? Call us: (540) 452-4199

Woodbrook Village

$200ks - $300ks

Woodbrook Village, Winchester, VA

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

Gatherings at Potomac Sta...

$400ks - $500ks

Gatherings at Potomac Sta..., Leesburg, VA

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

Ballenger Run

$300ks - $400ks

Ballenger Run, Frederick, MD

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

Lexington 7

$600ks - $700ks

Lexington 7, Ashburn, VA

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

The Signature at Broadlan...

$300ks - $400ks

The Signature at Broadlan..., Ashburn, VA

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

Cross Creek Village

$300ks

Cross Creek Village, Winchester, VA

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

The Village at Foxfield

$300ks - $500ks

The Village at Foxfield, Middletown, MD

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

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

Carter's Mill

$400ks - $700ks

Carter's Mill, Haymarket, VA

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

1...2

Trilogy® at Lake Frederick

100 SCOTER CT, LAKE FREDERICK, VA, 22630, Lake Frederick, VA 22630

$1,049,900

3 beds

4 baths

4,247 sq ft

100 SCOTER CT, LAKE FREDERICK, VA, 22630

Community: Trilogy® at Lake Frederick

Heritage Hunt

$399,900

2 beds

2 baths

1,292 sq ft

Condo

7065 HERITAGE HUNT DR 108, GAINESVILLE, ...

Community: Heritage Hunt

Trilogy® at Lake Frederick

109 EMPEROR DR, LAKE FREDERICK, VA, 2263..., Lake Frederick, VA 22630

$589,900

4 beds

4 baths

3,859 sq ft

109 EMPEROR DR, LAKE FREDERICK, VA, 2263...

Community: Trilogy® at Lake Frederick

New Crestwood Village

7016 BASSWOOD RD, FREDERICK, MD, 21703, Frederick, MD 21703

$349,900

2 beds

2 baths

1,128 sq ft

7016 BASSWOOD RD, FREDERICK, MD, 21703

Community: Crestwood Village

Regency at Belmont

19820 BODMER DR, ASHBURN, VA, 20147, Ashburn, VA 20147

$1,075,000

3 beds

4 baths

3,255 sq ft

19820 BODMER DR, ASHBURN, VA, 20147

Community: Regency at Belmont

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

Questions? Call us: (540) 452-4199

Crestwood Village

5746 BOX ELDER CT, FREDERICK, MD, 21703, Frederick, MD 21703

$358,500

2 beds

2 baths

1,225 sq ft

5746 BOX ELDER CT, FREDERICK, MD, 21703

Community: Crestwood Village

Birchwood at Brambleton

42849 LITTLEHALES TER, ASHBURN, VA, 2014..., Ashburn, VA 20148

$565,000

3 beds

3 baths

2,412 sq ft

Condo

42849 LITTLEHALES TER, ASHBURN, VA, 2014...

Community: Birchwood at Brambleton

Regency at Dominion Valley

15231 ROYAL CREST DR 101, HAYMARKET, VA,..., Haymarket, VA 20169

$459,900

2 beds

2 baths

1,538 sq ft

Condo

15231 ROYAL CREST DR 101, HAYMARKET, VA,...

Community: Regency at Dominion Valley

Cindy Certified

22145 HEADWATER TER 400, ASHBURN, VA, 20..., Ashburn, VA 20148

$960,000

3 beds

3 baths

2,285 sq ft

Condo

22145 HEADWATER TER 400, ASHBURN, VA, 20...

Lansdowne Woods of Virginia

19350 MAGNOLIA GROVE SQ 201, LEESBURG, V..., Leesburg, VA 20176

$409,000

2 beds

2 baths

1,387 sq ft

Condo

19350 MAGNOLIA GROVE SQ 201, LEESBURG, V...

Community: Lansdowne Woods of Virginia

Dunbarton

$649,900

4 beds

4 baths

3,345 sq ft

12840 DUNBARTON DR, BRISTOW, VA, 20136

Community: Dunbarton

Regency at Belmont

43929 NORMAN NEWS TER, ASHBURN, VA, 2014..., Ashburn, VA 20147

$1,050,000

3 beds

4 baths

3,255 sq ft

43929 NORMAN NEWS TER, ASHBURN, VA, 2014...

Community: Regency at Belmont

Crestwood Village

5714 TAMARACK AVE, FREDERICK, MD, 21703, Frederick, MD 21703

$404,900

2 beds

2 baths

1,297 sq ft

5714 TAMARACK AVE, FREDERICK, MD, 21703

Community: Crestwood Village

The Flats at Heathcote Village by Del Webb

5810 MOONSTONE WAY 101, HAYMARKET, VA, 2..., Haymarket, VA 20169

$429,095

2 beds

2 baths

1,175 sq ft

Condo

5810 MOONSTONE WAY 101, HAYMARKET, VA, 2...

Community: The Flats at Heathcote Village by Del Webb

The Flats at Heathcote Village by Del Webb

5800 MOONSTONE WAY 107, HAYMARKET, VA, 2..., Haymarket, VA 20169

$411,080

1 beds

2 baths

1,175 sq ft

Condo

5800 MOONSTONE WAY 107, HAYMARKET, VA, 2...

Community: The Flats at Heathcote Village by Del Webb

Lansdowne Woods of Virginia

19375 CYPRESS RIDGE TER 702, LEESBURG, V..., Leesburg, VA 20176

$354,900

2 beds

2 baths

1,038 sq ft

Condo

19375 CYPRESS RIDGE TER 702, LEESBURG, V...

Community: Lansdowne Woods of Virginia

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

Questions? Call us: (540) 452-4199

Cedar Meadows

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

$495,000

3 beds

2 baths

1,634 sq ft

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

Community: Cedar Meadows

Potomac Green

20429 ISLAND W SQ, ASHBURN, VA, 20147, Ashburn, VA 20147

$745,000

3 beds

3 baths

2,253 sq ft

20429 ISLAND W SQ, ASHBURN, VA, 20147

Community: Potomac Green

Potomac Green

20594 GOLDEN RIDGE DR, ASHBURN, VA, 2014..., Ashburn, VA 20147

$910,000

3 beds

4 baths

2,973 sq ft

20594 GOLDEN RIDGE DR, ASHBURN, VA, 2014...

Community: Potomac Green

Trilogy® at Lake Frederick

130 EMPEROR DR, LAKE FREDERICK, VA, 2263..., Lake Frederick, VA 22630

$599,999

4 beds

4 baths

3,232 sq ft

130 EMPEROR DR, LAKE FREDERICK, VA, 2263...

Community: Trilogy® at Lake Frederick

Woodbrook Village

102 BUCKWOOD LN, WINCHESTER, VA, 22602, Winchester, VA 22602

$368,000

2 beds

2 baths

1,424 sq ft

102 BUCKWOOD LN, WINCHESTER, VA, 22602

Community: Woodbrook Village

Potomac Green

20759 CRESCENT POINTE PL, ASHBURN, VA, 2..., Ashburn, VA 20147

$949,900

3 beds

4 baths

2,973 sq ft

20759 CRESCENT POINTE PL, ASHBURN, VA, 2...

Community: Potomac Green

Cindy Certified

LOT 12 REGENT CIR, HAGERSTOWN, MD, 21742, Hagerstown, MD 21742

$399,990

3 beds

2 baths

1,368 sq ft

LOT 12 REGENT CIR, HAGERSTOWN, MD, 21742

Trilogy® at Lake Frederick

127 PIMPERNEL PL, LAKE FREDERICK, VA, 22..., Lake Frederick, VA 22630

$1,099,000

3 beds

4 baths

4,220 sq ft

127 PIMPERNEL PL, LAKE FREDERICK, VA, 22...

Community: Trilogy® at Lake Frederick

Heritage Hunt

13465 VICTORY GALLOP WAY, GAINESVILLE, V..., Gainesville, VA 20155

$630,000

2 beds

3 baths

1,987 sq ft

13465 VICTORY GALLOP WAY, GAINESVILLE, V...

Community: Heritage Hunt

Lansdowne Woods of Virginia

19375 CYPRESS RIDGE TER 916, LEESBURG, V..., Leesburg, VA 20176

$395,000

2 beds

2 baths

1,315 sq ft

Condo

19375 CYPRESS RIDGE TER 916, LEESBURG, V...

Community: Lansdowne Woods of Virginia

Heritage Hunt

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

$750,000

4 beds

4 baths

3,113 sq ft

13972 REAL QUITE CT, 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

Cindy Certified

2319 FIELD POINT RD 203, OAK HILL, VA, 2..., Oak Hill, VA 20171

$519,900

2 beds

2 baths

1,275 sq ft

Condo

2319 FIELD POINT RD 203, OAK HILL, VA, 2...

The Flats at Heathcote Village by Del Webb

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

$769,871

3 beds

4 baths

2,763 sq ft

5928 SUNSTONE LN, HAYMARKET, VA, 20169

Community: The Flats at Heathcote Village by Del Webb

Dunbarton

9716 SEAFIELD PL, BRISTOW, VA, 20136, Bristow, VA 20136

$625,000

3 beds

3 baths

2,760 sq ft

9716 SEAFIELD PL, BRISTOW, VA, 20136

Community: Dunbarton

The Flats at Heathcote Village by Del Webb

15497 EMERALD WAY, HAYMARKET, VA, 20169, Haymarket, VA 20169

$804,847

3 beds

4 baths

2,775 sq ft

15497 EMERALD WAY, HAYMARKET, VA, 20169

Community: The Flats at Heathcote Village by Del Webb

Heritage Hunt

5976 PINEY GROVE WAY, GAINESVILLE, VA, 2..., Gainesville, VA 20155

$839,000

4 beds

5 baths

4,373 sq ft

5976 PINEY GROVE WAY, GAINESVILLE, VA, 2...

Community: Heritage Hunt

Potomac Green

20577 ROSEWOOD MANOR SQ, ASHBURN, VA, 20..., Ashburn, VA 20147

$690,000

2 beds

2 baths

1,667 sq ft

20577 ROSEWOOD MANOR SQ, ASHBURN, VA, 20...

Community: Potomac Green

Trilogy® at Lake Frederick

122 TURNSTONE LN, LAKE FREDERICK, VA, 22..., Lake Frederick, VA 22630

$675,000

3 beds

4 baths

3,300 sq ft

122 TURNSTONE LN, LAKE FREDERICK, VA, 22...

Community: Trilogy® at Lake Frederick

Crestwood Village

6879 SNOWBERRY CT, FREDERICK, MD, 21703, Frederick, MD 21703

$389,900

2 beds

2 baths

1,404 sq ft

6879 SNOWBERRY CT, FREDERICK, MD, 21703

Community: Crestwood Village

Willow Lawn Cottages

1847 MELVOR LN, WINCHESTER, VA, 22601, Winchester, VA 22601

$355,000

2 beds

2 baths

1,234 sq ft

1847 MELVOR LN, WINCHESTER, VA, 22601

Community: Willow Lawn Cottages

Lansdowne Woods of Virginia

19355 CYPRESS RIDGE TER 314, LEESBURG, V..., Leesburg, VA 20176

$330,000

2 beds

2 baths

1,038 sq ft

Condo

19355 CYPRESS RIDGE TER 314, LEESBURG, V...

Community: Lansdowne Woods of Virginia

Trilogy® at Lake Frederick

100 WALLEYE CT, LAKE FREDERICK, VA, 2263..., Lake Frederick, VA 22630

$620,000

3 beds

3 baths

3,513 sq ft

100 WALLEYE CT, LAKE FREDERICK, VA, 2263...

Community: Trilogy® at Lake Frederick

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

Questions? Call us: (540) 452-4199

The Woodlands of Urbana

3411 ANGELICA WAY 203, FREDERICK, MD, 21..., Frederick, MD 21704

$415,000

2 beds

2 baths

1,456 sq ft

Condo

3411 ANGELICA WAY 203, FREDERICK, MD, 21...

Community: The Woodlands of Urbana

Trilogy® at Lake Frederick

132 BURKWOOD TER, LAKE FREDERICK, VA, 22..., Lake Frederick, VA 22630

$415,000

4 beds

4 baths

2,439 sq ft

132 BURKWOOD TER, LAKE FREDERICK, VA, 22...

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 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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51 communities

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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 29, 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

238 homes near Winchester Area

3 beds

4 baths

4,247 sq ft

2 beds

2 baths

1,292 sq ft

Condo

4 beds

4 baths

3,859 sq ft

2 beds

2 baths

1,128 sq ft

3 beds

4 baths

3,255 sq ft

2 beds

2 baths

1,225 sq ft

3 beds

3 baths

2,412 sq ft

Condo

2 beds

2 baths

1,538 sq ft

Condo

3 beds

3 baths

2,285 sq ft

Condo

2 beds

2 baths

1,387 sq ft

Condo

4 beds

4 baths

3,345 sq ft

3 beds

4 baths

3,255 sq ft

2 beds

2 baths

1,297 sq ft

2 beds

2 baths

1,175 sq ft

Condo

1 beds

2 baths

1,175 sq ft

Condo

2 beds

2 baths

1,038 sq ft

Condo

3 beds

2 baths

1,634 sq ft

3 beds

3 baths

2,253 sq ft

3 beds

4 baths

2,973 sq ft

4 beds

4 baths

3,232 sq ft

2 beds

2 baths

1,424 sq ft

3 beds

4 baths

2,973 sq ft

3 beds

2 baths

1,368 sq ft