Winchester Area, VA 55+ active adult communities & homes for sale - Page 6

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

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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

Rosehill Manor Villas

19601 LAVENDER LN, HAGERSTOWN, MD, 21742, Hagerstown, MD 21742

$374,900

3 beds

2 baths

1,735 sq ft

19601 LAVENDER LN, HAGERSTOWN, MD, 21742

Community: Rosehill Manor Villas

Lansdowne Woods of Virginia

19385 CYPRESS RIDGE TER 519, LEESBURG, V..., Leesburg, VA 20176

$319,990

2 beds

2 baths

1,038 sq ft

Condo

19385 CYPRESS RIDGE TER 519, LEESBURG, V...

Community: Lansdowne Woods of Virginia

Willow Lawn Cottages

1856 MELVOR LN, WINCHESTER, VA, 22601, Winchester, VA 22601

$349,900

2 beds

2 baths

1,219 sq ft

1856 MELVOR LN, WINCHESTER, VA, 22601

Community: Willow Lawn Cottages

Heritage Hunt

6877 SADDLE RUN WAY, GAINESVILLE, VA, 20..., Gainesville, VA 20155

$639,000

3 beds

2 baths

1,809 sq ft

6877 SADDLE RUN WAY, GAINESVILLE, VA, 20...

Community: Heritage Hunt

Cindy Certified

2319 FIELD POINT RD 102, HERNDON, VA, 20..., Herndon, VA 20171

$525,000

2 beds

2 baths

1,451 sq ft

Condo

2319 FIELD POINT RD 102, HERNDON, VA, 20...

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

Questions? Call us: (540) 452-4199

The Village at Freedom Hills

13928 PATRIOT WAY, HAGERSTOWN, MD, 21740, Hagerstown, MD 21740

$370,000

2 beds

2 baths

1,663 sq ft

13928 PATRIOT WAY, HAGERSTOWN, MD, 21740

Community: The Village at Freedom Hills

Cindy Certified

LOT 4 GRAY MEADOW CT, WARRENTON, VA, 201..., Warrenton, VA 20187

$980,000

4 beds

3 baths

2,270 sq ft

LOT 4 GRAY MEADOW CT, WARRENTON, VA, 201...

Cindy Certified

LOT 5 GRAY MEADOW CT, WARRENTON, VA, 201..., Warrenton, VA 20187

$799,850

3 beds

2 baths

1,768 sq ft

LOT 5 GRAY MEADOW CT, WARRENTON, VA, 201...

Trilogy® at Lake Frederick

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

$545,000

2 beds

2 baths

1,791 sq ft

110 SWITCHGRASS WAY, LAKE FREDERICK, VA,...

Community: Trilogy® at Lake Frederick

Gatherings at Wellington

9204 CHARLESTON DR 207, MANASSAS, VA, 20..., Manassas, VA 20110

$399,900

2 beds

2 baths

2,006 sq ft

Condo

9204 CHARLESTON DR 207, MANASSAS, VA, 20...

Community: Gatherings at Wellington

Cindy Certified

640 ARMSTRONG AVE, HAGERSTOWN, MD, 21740, Hagerstown, MD 21740

$386,088

4 beds

2 baths

1,698 sq ft

640 ARMSTRONG AVE, HAGERSTOWN, MD, 21740

The Woodlands of Urbana

3411 ANGELICA WAY 401, FREDERICK, MD, 21..., Frederick, MD 21704

$495,000

2 beds

2 baths

1,785 sq ft

Condo

3411 ANGELICA WAY 401, FREDERICK, MD, 21...

Community: The Woodlands of Urbana

Trilogy® at Lake Frederick

120 LEATHER FLOWER DR, LAKE FREDERICK, V..., Lake Frederick, VA 22630

$375,000

3 beds

4 baths

2,250 sq ft

120 LEATHER FLOWER DR, LAKE FREDERICK, V...

Community: Trilogy® at Lake Frederick

The Woodlands of Urbana

2913 HERB GARDEN DR, FREDERICK, MD, 2170..., Frederick, MD 21704

$825,000

3 beds

3 baths

3,070 sq ft

2913 HERB GARDEN DR, FREDERICK, MD, 2170...

Community: The Woodlands of Urbana

Rosehill Manor Villas

19704 OLEANDER CT, HAGERSTOWN, MD, 21742, Hagerstown, MD 21742

$449,990

3 beds

3 baths

1,895 sq ft

19704 OLEANDER CT, HAGERSTOWN, MD, 21742

Community: Rosehill Manor Villas

Suffield Meadows

6715 HOLLY FARM LN, WARRENTON, VA, 20187, Warrenton, VA 20187

$555,000

3 beds

4 baths

3,350 sq ft

Condo

6715 HOLLY FARM LN, WARRENTON, VA, 20187

Community: Suffield Meadows

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

Questions? Call us: (540) 452-4199

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

$449,000

3 beds

2 baths

1,493 sq ft

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

Community: Cedar Meadows

Trilogy® at Lake Frederick

104 RHODODENDRON CT, LAKE FREDERICK, VA,..., Lake Frederick, VA 22630

$729,990

3 beds

3 baths

2,457 sq ft

104 RHODODENDRON CT, LAKE FREDERICK, VA,...

Community: Trilogy® at Lake Frederick

Willow Run

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

$609,990

4 beds

3 baths

2,909 sq ft

232 HYDRANGEA WAY, WINCHESTER, VA, 22602

Community: Willow Run

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

Trilogy® at Lake Frederick

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

$580,000

3 beds

3 baths

2,721 sq ft

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

Community: Trilogy® at Lake Frederick

Emerald Pointe

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

$399,900

2 beds

2 baths

1,726 sq ft

13301 MARQUISE DR, HAGERSTOWN, MD, 21742

Community: Emerald Pointe

Cindy Certified

22171 SPRINGSIDE TER 300, ASHBURN, VA, 2..., Ashburn, VA 20148

$830,000

3 beds

3 baths

2,285 sq ft

Condo

22171 SPRINGSIDE TER 300, ASHBURN, VA, 2...

The Woodlands of Urbana

3422 ANGELICA WAY 103, FREDERICK, MD, 21..., Frederick, MD 21704

$399,000

2 beds

2 baths

1,489 sq ft

Condo

3422 ANGELICA WAY 103, FREDERICK, MD, 21...

Community: The Woodlands of Urbana

Trilogy® at Lake Frederick

106 RHODODENDRON CT, LAKE FREDERICK, VA,..., Lake Frederick, VA 22630

$745,990

2 beds

2 baths

2,058 sq ft

106 RHODODENDRON CT, LAKE FREDERICK, VA,...

Community: Trilogy® at Lake Frederick

Lansdowne Woods of Virginia

19365 CYPRESS RIDGE TER 1115, LEESBURG, ..., Leesburg, VA 20176

$470,000

3 beds

2 baths

1,475 sq ft

Condo

19365 CYPRESS RIDGE TER 1115, LEESBURG, ...

Community: Lansdowne Woods of Virginia

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

Questions? Call us: (540) 452-4199

Emerald Pointe

13226 ONYX DR S175, HAGERSTOWN, MD, 2174..., Hagerstown, MD 21742

$524,900

2 beds

2 baths

13226 ONYX DR S175, HAGERSTOWN, MD, 2174...

Community: Emerald Pointe

Trilogy® at Lake Frederick

107 YELLOW BIRCH CT, LAKE FREDERICK, VA,..., Lake Frederick, VA 22630

$969,999

3 beds

5 baths

4,465 sq ft

107 YELLOW BIRCH CT, LAKE FREDERICK, VA,...

Community: Trilogy® at Lake Frederick

Trilogy® at Lake Frederick

124 CHECKERSPOT WAY, LAKE FREDERICK, VA,..., Lake Frederick, VA 22630

$424,000

4 beds

4 baths

2,508 sq ft

124 CHECKERSPOT WAY, LAKE FREDERICK, VA,...

Community: Trilogy® at Lake Frederick

Cindy Certified

7816 FAIRPLAY RD, FAIRPLAY, MD, 21733, Fairplay, MD 21733

$519,900

3 beds

2 baths

2,000 sq ft

7816 FAIRPLAY RD, FAIRPLAY, MD, 21733

Willow Run

228 HYDRANGEA WAY, WINCHESTER, VA, 22602, Winchester, VA 22602

$646,045

4 beds

3 baths

3,031 sq ft

228 HYDRANGEA WAY, WINCHESTER, VA, 22602

Community: Willow Run

Birchwood at Brambleton

23631 HAVELOCK WALK TER 421, ASHBURN, VA..., Ashburn, VA 20148

$535,000

3 beds

2 baths

1,906 sq ft

Condo

23631 HAVELOCK WALK TER 421, ASHBURN, VA...

Community: Birchwood at Brambleton

Rosehill Manor Villas

19604 LAVENDER LN, HAGERSTOWN, MD, 21742, Hagerstown, MD 21742

$369,900

2 beds

2 baths

1,767 sq ft

19604 LAVENDER LN, HAGERSTOWN, MD, 21742

Community: Rosehill Manor Villas

Cindy Certified

10918 CLINTON AVE, HAGERSTOWN, MD, 21740, Hagerstown, MD 21740

$349,900

3 beds

2 baths

1,467 sq ft

10918 CLINTON AVE, HAGERSTOWN, MD, 21740

The Village at Freedom Hills

13948 PATRIOT WAY, HAGERSTOWN, MD, 21740, Hagerstown, MD 21740

$299,900

2 beds

2 baths

1,430 sq ft

13948 PATRIOT WAY, HAGERSTOWN, MD, 21740

Community: The Village at Freedom Hills

Cindy Certified

LOT 6 GRAY MEADOW CT, WARRENTON, VA, 201..., Warrenton, VA 20187

$1,080,800

4 beds

3 baths

2,270 sq ft

LOT 6 GRAY MEADOW CT, WARRENTON, VA, 201...

Lansdowne Woods of Virginia

19385 CYPRESS RIDGE TER 920, LEESBURG, V..., Leesburg, VA 20176

$450,000

3 beds

2 baths

1,475 sq ft

Condo

19385 CYPRESS RIDGE TER 920, 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

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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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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 6

51 communities near Winchester Area

238 homes near Winchester Area

3 beds

2 baths

1,735 sq ft

2 beds

2 baths

1,038 sq ft

Condo

2 beds

2 baths

1,219 sq ft

3 beds

2 baths

1,809 sq ft

2 beds

2 baths

1,451 sq ft

Condo

2 beds

2 baths

1,663 sq ft

4 beds

3 baths

2,270 sq ft

3 beds

2 baths

1,768 sq ft

2 beds

2 baths

1,791 sq ft

2 beds

2 baths

2,006 sq ft

Condo

4 beds

2 baths

1,698 sq ft

2 beds

2 baths

1,785 sq ft

Condo

3 beds

4 baths

2,250 sq ft

3 beds

3 baths

3,070 sq ft

3 beds

3 baths

1,895 sq ft

3 beds

4 baths

3,350 sq ft

Condo

3 beds

2 baths

1,424 sq ft

Condo

3 beds

2 baths

1,493 sq ft

3 beds

3 baths

2,457 sq ft

4 beds

3 baths

2,909 sq ft

2 beds

2 baths

1,850 sq ft

3 beds

3 baths

2,721 sq ft

2 beds

2 baths

1,726 sq ft

3 beds

3 baths