Winchester Area, VA 55+ active adult communities & homes for sale - Page 3

238 homes 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 - $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

2 rating (1 review)

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

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Questions? Call us: (540) 452-4199

5 rating (1 review)

Crestwood Village

$200ks - $500ks

Crestwood Village, Frederick, MD

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

5 rating (1 review)

Regency at Dominion Valle...

$300ks - $1Ms

Regency at Dominion Valle..., Haymarket, VA

Resale Only | 55+ age-restricted | Built 2001 - 2017 | 855 homes

The Woodlands of Urbana

$500ks - $700ks

The Woodlands of Urbana, Urbana, MD

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

Bloomfields 55+

$700ks - $800ks

Bloomfields 55+, Frederick, MD

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

Regency at Belmont

$600ks - $900ks

Regency at Belmont, Ashburn, VA

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

Willow Lawn Cottages

$300ks

Willow Lawn Cottages, Winchester, VA

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

5 rating (2 reviews)

Potomac Green

$400ks - $800ks

Potomac Green, Ashburn, VA

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

Emerald Pointe

$300ks - $500ks

Emerald Pointe, Hagerstown, MD

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

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

The Village at Freedom Hi...

$300ks

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

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

Heritage Highlands

$300ks - $400ks

Heritage Highlands, Lovettsville, VA

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

Cedar Meadows

$300ks - $400ks

Cedar Meadows, White Post, VA

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

Suffield Meadows

$400ks

Suffield Meadows, Warrenton, VA

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

Winchester Landing

$300ks - $400ks

Winchester Landing, Winchester, VA

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

Rosehill Manor Villas

$300ks

Rosehill Manor Villas, Hagerstown, MD

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

Liberty Grove

$200ks - $300ks

Liberty Grove, Manassas, VA

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

5 rating (1 review)

Gatherings at Wellington

$300ks - $400ks

Gatherings at Wellington, Manassas, VA

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

Vistas at Lansdowne

$800ks

Vistas at Lansdowne, Lansdowne, VA

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

3 rating (2 reviews)

Dunbarton

$300ks - $500ks

Dunbarton, Bristow, VA

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

The Signature at Broadlan...

$300ks - $400ks

The Signature at Broadlan..., Ashburn, VA

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

5 rating (1 review)

Four Seasons at Vint Hill

$600ks

Four Seasons at Vint Hill, Warrenton, VA

Resale Only | 55+ age-restricted | Built 2004 - 2006 | 100 homes

Woodbrook Village

$200ks - $300ks

Woodbrook Village, Winchester, VA

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

Boxwood Villas

$500ks - $600ks

Boxwood Villas, Urbana, MD

Resale Only | 55+ age-restricted | Built 2019 - 2021 | 92 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

Lexington 7

$600ks - $700ks

Lexington 7, Ashburn, VA

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

Regency at Ashburn

$300ks - $800ks

Regency at Ashburn, Ashburn, VA

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

Cross Creek Village

$300ks

Cross Creek Village, Winchester, VA

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

Gatherings at Potomac Sta...

$400ks - $500ks

Gatherings at Potomac Sta..., Leesburg, VA

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

Montebello

$300ks - $600ks

Montebello, Sterling, VA

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

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

Questions? Call us: (540) 452-4199

Robinson Manor

$600ks - $700ks

Robinson Manor, Gainesville, VA

New Construction | 55+ age-restricted | Built 2023 - present | 50 homes

The Villages at Broadland...

$400ks

The Villages at Broadland..., Ashburn, VA

New and Resale | 55+ age-restricted | Built 2013 - present | 78 homes

1...2

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

Heritage Hunt

6563 BULLEN BLUFF TER, GAINESVILLE, VA, ..., Gainesville, VA 20155

$540,000

2 beds

2 baths

1,676 sq ft

6563 BULLEN BLUFF TER, GAINESVILLE, VA, ...

Community: Heritage Hunt

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

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

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...

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

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

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

$650,000

2 beds

2 baths

1,667 sq ft

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

Community: Potomac Green

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

$339,900

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

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

Cross Creek Village

100 GOOSEBERRY DR, WINCHESTER, VA, 22602, Winchester, VA 22602

$499,000

2 beds

3 baths

2,679 sq ft

100 GOOSEBERRY DR, WINCHESTER, VA, 22602

Community: Cross Creek Village

Heritage Highlands

56 HARPERS MILL WAY, LOVETTSVILLE, VA, 2..., Lovettsville, VA 20180

$589,000

3 beds

3 baths

2,119 sq ft

56 HARPERS MILL WAY, LOVETTSVILLE, VA, 2...

Community: Heritage Highlands

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

Questions? Call us: (540) 452-4199

Gatherings at Potomac Station

700 MOUNT AIRY TER 202, LEESBURG, VA, 20..., Leesburg, VA 20176

$520,000

2 beds

2 baths

1,574 sq ft

Condo

700 MOUNT AIRY TER 202, LEESBURG, VA, 20...

Community: Gatherings at Potomac Station

Lexington 7

44537 FIERY SKIPPER TER, ASHBURN, VA, 20..., Ashburn, VA 20147

$845,000

3 beds

3 baths

2,608 sq ft

44537 FIERY SKIPPER TER, ASHBURN, VA, 20...

Community: Lexington 7

Cindy Certified

3925 FAIR RIDGE DR 303, FAIRFAX, VA, 220..., Fairfax, VA 22033

$549,900

2 beds

2 baths

1,301 sq ft

Condo

3925 FAIR RIDGE DR 303, FAIRFAX, VA, 220...

Crestwood Village

6861 SNOWBERRY CT, FREDERICK, MD, 21703, Frederick, MD 21703

$325,000

2 beds

2 baths

1,164 sq ft

6861 SNOWBERRY CT, FREDERICK, MD, 21703

Community: Crestwood Village

Dunbarton

13199 ORMOND DR, BRISTOW, VA, 20136, Bristow, VA 20136

$649,900

4 beds

4 baths

3,216 sq ft

13199 ORMOND DR, BRISTOW, VA, 20136

Community: Dunbarton

Liberty Grove

8600 LIBERTY TRL 102, MANASSAS, VA, 2011..., Manassas, VA 20110

$259,000

1 beds

2 baths

1,131 sq ft

Condo

8600 LIBERTY TRL 102, MANASSAS, VA, 2011...

Community: Liberty Grove

Heritage Hunt

13217 TRIPLE CROWN LOOP, GAINESVILLE, VA..., Gainesville, VA 20155

$714,000

3 beds

3 baths

2,520 sq ft

13217 TRIPLE CROWN LOOP, GAINESVILLE, VA...

Community: Heritage Hunt

Lansdowne Woods of Virginia

19350 MAGNOLIA GROVE SQ 208, LEESBURG, V..., Leesburg, VA 20176

$465,000

2 beds

2 baths

1,444 sq ft

Condo

19350 MAGNOLIA GROVE SQ 208, LEESBURG, V...

Community: Lansdowne Woods of Virginia

Lansdowne Woods of Virginia

19365 CYPRESS RIDGE TER 821, LEESBURG, V..., Leesburg, VA 20176

$459,000

3 beds

2 baths

1,509 sq ft

Condo

19365 CYPRESS RIDGE TER 821, LEESBURG, V...

Community: Lansdowne Woods of Virginia

Birchwood at Brambleton

23688 BOLTON CRESCENT TER 304, ASHBURN, ..., Ashburn, VA 20148

$489,990

2 beds

2 baths

1,280 sq ft

Condo

23688 BOLTON CRESCENT TER 304, ASHBURN, ...

Community: Birchwood at Brambleton

Regency at Belmont

19818 BODMER DR, ASHBURN, VA, 20147, Ashburn, VA 20147

$1,045,000

4 beds

4 baths

3,255 sq ft

19818 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

Heritage Hunt

13225 FIELDSTONE WAY, GAINESVILLE, VA, 2..., Gainesville, VA 20155

$800,500

3 beds

4 baths

3,460 sq ft

13225 FIELDSTONE WAY, GAINESVILLE, VA, 2...

Community: Heritage Hunt

Cindy Certified

21950 GARGANEY TER 407, ASHBURN, VA, 201..., Ashburn, VA 20147

$465,000

2 beds

2 baths

1,301 sq ft

Condo

21950 GARGANEY TER 407, ASHBURN, VA, 201...

Lansdowne Woods of Virginia

19355 CYPRESS RIDGE TER 310, LEESBURG, V..., Leesburg, VA 20176

$468,900

2 beds

2 baths

1,500 sq ft

Condo

19355 CYPRESS RIDGE TER 310, LEESBURG, V...

Community: Lansdowne Woods of Virginia

Cindy Certified

42284 TACKROOM TER, ALDIE, VA, 20105, Aldie, VA 20105

$424,900

2 beds

2 baths

1,438 sq ft

Condo

42284 TACKROOM TER, ALDIE, VA, 20105

Vistas at Lansdowne

44237 SILVERPALM GROVE TER, LEESBURG, VA..., Leesburg, VA 20176

$879,000

3 beds

4 baths

3,909 sq ft

44237 SILVERPALM GROVE TER, LEESBURG, VA...

Community: Vistas at Lansdowne

Trilogy® at Lake Frederick

120 NUTHATCH DR, LAKE FREDERICK, VA, 226..., Lake Frederick, VA 22630

$579,900

3 beds

2 baths

1,784 sq ft

120 NUTHATCH DR, LAKE FREDERICK, VA, 226...

Community: Trilogy® at Lake Frederick

Cindy Certified

41900 METAMORPHIC SQ 400, ALDIE, VA, 201..., Aldie, VA 20105

$480,000

3 beds

2 baths

1,516 sq ft

Condo

41900 METAMORPHIC SQ 400, ALDIE, VA, 201...

Potomac Green

20580 HOPE SPRING TER 204, ASHBURN, VA, ..., Ashburn, VA 20147

$499,990

2 beds

2 baths

1,515 sq ft

Condo

20580 HOPE SPRING TER 204, ASHBURN, VA, ...

Community: Potomac Green

Birchwood at Brambleton

42976 TRUMAN TER, ASHBURN, VA, 20148, Ashburn, VA 20148

$799,990

3 beds

4 baths

2,742 sq ft

42976 TRUMAN TER, ASHBURN, VA, 20148

Community: Birchwood at Brambleton

Trilogy® at Lake Frederick

116 IRONWEED DR, LAKE FREDERICK, VA, 226..., Lake Frederick, VA 22630

$575,000

3 beds

3 baths

2,733 sq ft

116 IRONWEED DR, LAKE FREDERICK, VA, 226...

Community: Trilogy® at Lake Frederick

Lansdowne Woods of Virginia

19385 CYPRESS RIDGE TER 520, LEESBURG, V..., Leesburg, VA 20176

$475,000

3 beds

2 baths

1,627 sq ft

Condo

19385 CYPRESS RIDGE TER 520, 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

Potomac Green

20611 GOLDEN RIDGE DR, ASHBURN, VA, 2014..., Ashburn, VA 20147

$850,000

3 beds

3 baths

2,243 sq ft

20611 GOLDEN RIDGE DR, ASHBURN, VA, 2014...

Community: Potomac Green

Birchwood at Brambleton

23630 HAVELOCK WALK 305, ASHBURN, VA, 20..., Ashburn, VA 20148

$425,000

2 beds

2 baths

1,059 sq ft

Condo

23630 HAVELOCK WALK 305, ASHBURN, VA, 20...

Community: Birchwood at Brambleton

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Winchester Area

Frequently Asked Questions

What size 55+ communities are there in the Winchester Area?

Of the 12 55+ communities in the Winchester Area, 12 are for sale and none are rentals. By size, 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 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 588 days. The average price of homes for sale in these communities is approximately $491,100, though prices can range widely based on the size, location, and amenities of the communities. For example, homes in Willow Run average around $623,623, while homes in Cottage Glen average around $464,750.

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

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238 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: Oct 22, 2026.
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Winchester Area, VA 55+ active adult communities & homes for sale - Page 3

51 communities near Winchester Area

238 homes near Winchester Area

2 beds

2 baths

1,424 sq ft

2 beds

2 baths

1,676 sq ft

3 beds

4 baths

4,220 sq ft

2 beds

2 baths

1,315 sq ft

Condo

2 beds

2 baths

1,275 sq ft

Condo

3 beds

4 baths

2,763 sq ft

3 beds

4 baths

2,775 sq ft

4 beds

5 baths

4,373 sq ft

2 beds

2 baths

1,667 sq ft

2 beds

2 baths

1,404 sq ft

2 beds

2 baths

1,234 sq ft

2 beds

2 baths

1,038 sq ft

Condo

2 beds

2 baths

1,456 sq ft

Condo

4 beds

4 baths

2,439 sq ft

2 beds

3 baths

2,679 sq ft

3 beds

3 baths

2,119 sq ft

2 beds

2 baths

1,574 sq ft

Condo

3 beds

3 baths

2,608 sq ft

2 beds

2 baths

1,301 sq ft

Condo

2 beds

2 baths

1,164 sq ft

4 beds

4 baths

3,216 sq ft

1 beds

2 baths

1,131 sq ft

Condo

3 beds

3 baths

2,520 sq ft

2 beds