Winchester Area, VA 55+ active adult communities & homes for sale - Page 2

51 communities near Winchester Area

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Lexington Square

Lexington Square

$800ks - $1Ms

Lexington Square, Ashburn, VA

New Construction | 55+ age-restricted | Built 2024 - present | 23 homes

Winchester Landing

Winchester Landing

$300ks - $400ks

Winchester Landing, Winchester, VA

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

The Highlands at Blue Rid...

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

Heritage Highlands

$300ks - $400ks

Heritage Highlands, Lovettsville, VA

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

Lexington 7

Lexington 7

$600ks - $700ks

Lexington 7, Ashburn, VA

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

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

Questions? Call us: (540) 452-4199

The Signature at Broadlan...

The Signature at Broadlan...

$300ks - $400ks

The Signature at Broadlan..., Ashburn, VA

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

Regency at Ashburn

Regency at Ashburn

$300ks - $800ks

Regency at Ashburn, Ashburn, VA

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

Carter's Mill

Carter's Mill

$400ks - $700ks

Carter's Mill, Haymarket, VA

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

3 rating (2 reviews)

Dunbarton

Dunbarton

$300ks - $500ks

Dunbarton, Bristow, VA

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

Cross Creek Village

Cross Creek Village

$300ks

Cross Creek Village, Winchester, VA

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

Woodbrook Village

Woodbrook Village

$200ks - $300ks

Woodbrook Village, Winchester, VA

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

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New Regency at Dominion Valley

15110 HEATHER MILL LN 404, HAYMARKET, VA..., Haymarket, VA 20169

$475,000

2 beds

|

2 baths

|

1,499 sq ft

|

Condo

15110 HEATHER MILL LN 404, HAYMARKET, VA...

Community: Regency at Dominion Valley

New Trilogy® at Lake Frederick

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

$639,900

4 beds

|

4 baths

|

3,859 sq ft

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

Community: Trilogy® at Lake Frederick

New Heritage Hunt

6901 SADDLE RUN WAY, GAINESVILLE, VA, 20..., Gainesville, VA 20155

$700,000

3 beds

|

3 baths

|

2,618 sq ft

6901 SADDLE RUN WAY, GAINESVILLE, VA, 20...

Community: Heritage Hunt

New Potomac Green

44360 SUNSET MAPLE DR, ASHBURN, VA, 2014..., Ashburn, VA 20147

$649,999

2 beds

|

3 baths

|

2,060 sq ft

44360 SUNSET MAPLE DR, ASHBURN, VA, 2014...

Community: Potomac Green

New The Village at Freedom Hills

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

$385,000

2 beds

|

2 baths

|

1,663 sq ft

13928 PATRIOT WAY, HAGERSTOWN, MD, 21740

Community: The Village at Freedom Hills

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

Questions? Call us: (540) 452-4199

New The Flats at Heathcote Village by Del Webb

5800 MOONSTONE WAY 7, HAYMARKET, VA, 201..., Haymarket, VA 20169

$474,990

2 beds

|

2 baths

|

1,445 sq ft

|

Condo

5800 MOONSTONE WAY 7, HAYMARKET, VA, 201...

Community: The Flats at Heathcote Village by Del Webb

New The Flats at Heathcote Village by Del Webb

5800 MOONSTONE WAY 6, HAYMARKET, VA, 201..., Haymarket, VA 20169

$374,990

1 beds

|

2 baths

|

995 sq ft

|

Condo

5800 MOONSTONE WAY 6, HAYMARKET, VA, 201...

Community: The Flats at Heathcote Village by Del Webb

New The Flats at Heathcote Village by Del Webb

5800 MOONSTONE WAY 5, HAYMARKET, VA, 201..., Haymarket, VA 20169

$589,990

3 beds

|

2 baths

|

1,850 sq ft

|

Condo

5800 MOONSTONE WAY 5, HAYMARKET, VA, 201...

Community: The Flats at Heathcote Village by Del Webb

New The Flats at Heathcote Village by Del Webb

5800 MOONSTONE WAY 4, HAYMARKET, VA, 201..., Haymarket, VA 20169

$539,990

2 beds

|

2 baths

|

1,520 sq ft

|

Condo

5800 MOONSTONE WAY 4, HAYMARKET, VA, 201...

Community: The Flats at Heathcote Village by Del Webb

New The Flats at Heathcote Village by Del Webb

5800 MOONSTONE WAY 3, HAYMARKET, VA, 201..., Haymarket, VA 20169

$574,990

3 beds

|

2 baths

|

1,735 sq ft

|

Condo

5800 MOONSTONE WAY 3, HAYMARKET, VA, 201...

Community: The Flats at Heathcote Village by Del Webb

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.

New The Flats at Heathcote Village by Del Webb

5800 MOONSTONE WAY 2, HAYMARKET, VA, 201..., Haymarket, VA 20169

$429,990

2 beds

|

2 baths

|

1,345 sq ft

|

Condo

5800 MOONSTONE WAY 2, HAYMARKET, VA, 201...

Community: The Flats at Heathcote Village by Del Webb

New The Flats at Heathcote Village by Del Webb

5800 MOONSTONE WAY 1, HAYMARKET, VA, 201..., Haymarket, VA 20169

$494,990

2 beds

|

2 baths

|

1,475 sq ft

|

Condo

5800 MOONSTONE WAY 1, HAYMARKET, VA, 201...

Community: The Flats at Heathcote Village by Del Webb

New Trilogy® at Lake Frederick

110 SWITCHGRASS WAY, LAKE FREDERICK, VA,..., Lake Frederick, VA 22663

$570,000

2 beds

|

2 baths

|

1,791 sq ft

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

Community: Trilogy® at Lake Frederick

New Trilogy® at Lake Frederick

117 PINTAIL WAY, LAKE FREDERICK, VA, 226..., Lake Frederick, VA 22630

$842,900

4 beds

|

4 baths

|

4,804 sq ft

117 PINTAIL WAY, LAKE FREDERICK, VA, 226...

Community: Trilogy® at Lake Frederick

New Heritage Hunt

13455 BRIGHTVIEW WAY, GAINESVILLE, VA, 2..., Gainesville, VA 20155

$899,000

3 beds

|

3 baths

|

3,080 sq ft

13455 BRIGHTVIEW WAY, GAINESVILLE, VA, 2...

Community: Heritage Hunt

New The Woodlands of Urbana

3224 IVY MEADOW DR, FREDERICK, MD, 21704, Frederick, MD 21704

$915,000

2 beds

|

3 baths

|

2,812 sq ft

3224 IVY MEADOW DR, FREDERICK, MD, 21704

Community: The Woodlands of Urbana

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

Questions? Call us: (540) 452-4199

New Gatherings at Wellington

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

$409,900

2 beds

|

2 baths

|

2,006 sq ft

|

Condo

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

Community: Gatherings at Wellington

New Lansdowne Woods of Virginia

19355 CYPRESS RIDGE TER 1022, LEESBURG, ..., Leesburg, VA 20176

$380,000

2 beds

|

2 baths

|

1,038 sq ft

|

Condo

19355 CYPRESS RIDGE TER 1022, LEESBURG, ...

Community: Lansdowne Woods of Virginia

New Gatherings at Wellington

9204 CHARLESTON DR 303, MANASSAS, VA, 20..., Manassas, VA 20110

$385,000

2 beds

|

2 baths

|

1,558 sq ft

|

Condo

9204 CHARLESTON DR 303, MANASSAS, VA, 20...

Community: Gatherings at Wellington

Regency at Belmont

43917 MERCER RUN TER, ASHBURN, VA, 20147, Ashburn, VA 20147

$1,025,000

3 beds

|

4 baths

|

3,243 sq ft

43917 MERCER RUN TER, ASHBURN, VA, 20147

Community: Regency at Belmont

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.

Lansdowne Woods of Virginia

19355 CYPRESS RIDGE TER 404, LEESBURG, V..., Leesburg, VA 20176

$358,500

2 beds

|

2 baths

|

1,105 sq ft

|

Condo

19355 CYPRESS RIDGE TER 404, LEESBURG, V...

Community: Lansdowne Woods of Virginia

Central Parke at Lowes Island

20745 ROYAL PALACE SQ 209, STERLING, VA,..., Sterling, VA 20165

$489,900

3 beds

|

2 baths

|

1,816 sq ft

|

Condo

20745 ROYAL PALACE SQ 209, STERLING, VA,...

Community: Central Parke at Lowes Island

Birchwood at Brambleton

42863 BEAVER CROSSING SQ, ASHBURN, VA, 2..., Ashburn, VA 20148

$1,079,900

3 beds

|

3 baths

|

2,830 sq ft

42863 BEAVER CROSSING SQ, ASHBURN, VA, 2...

Community: Birchwood at Brambleton

Heritage Hunt

13191 TRIPLE CROWN LOOP, GAINESVILLE, VA..., Gainesville, VA 20155

$785,000

4 beds

|

5 baths

|

4,664 sq ft

13191 TRIPLE CROWN LOOP, GAINESVILLE, VA...

Community: Heritage Hunt

Regency at Dominion Valley

5117 FALDO DR, HAYMARKET, VA, 20169, Haymarket, VA 20169

$925,000

4 beds

|

3 baths

|

3,428 sq ft

5117 FALDO DR, HAYMARKET, VA, 20169

Community: Regency at Dominion Valley

Birchwood at Brambleton

42760 LITTLEHALES TER, ASHBURN, VA, 2014..., Ashburn, VA 20148

$1,200,000

4 beds

|

4 baths

|

3,838 sq ft

42760 LITTLEHALES TER, ASHBURN, VA, 2014...

Community: Birchwood at Brambleton

Lansdowne Woods of Virginia

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

$334,990

2 beds

|

2 baths

|

1,038 sq ft

|

Condo

19355 CYPRESS RIDGE TER 314, 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

The Woodlands of Urbana

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

$525,000

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

102 PEREGRINE CT, LAKE FREDERICK, VA, 22..., Lake Frederick, VA 22630

$775,000

3 beds

|

3 baths

|

3,051 sq ft

102 PEREGRINE CT, LAKE FREDERICK, VA, 22...

Community: Trilogy® at Lake Frederick

Heritage Hunt

13001 TRIPLE CROWN LOOP, GAINESVILLE, VA..., Gainesville, VA 20155

$850,000

4 beds

|

3 baths

|

4,074 sq ft

13001 TRIPLE CROWN LOOP, GAINESVILLE, VA...

Community: Heritage Hunt

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.

Birchwood at Brambleton

42729 AUTUMN DAY TER, ASHBURN, VA, 20148, Ashburn, VA 20148

$1,050,000

3 beds

|

3 baths

|

2,802 sq ft

42729 AUTUMN DAY TER, ASHBURN, VA, 20148

Community: Birchwood at Brambleton

Rosehill Manor Villas

19642 LAVENDER LN, HAGERSTOWN, MD, 21742, Hagerstown, MD 21742

$399,900

3 beds

|

2 baths

|

1,712 sq ft

19642 LAVENDER LN, HAGERSTOWN, MD, 21742

Community: Rosehill Manor Villas

Suffield Meadows

6704 HOLLY FARM LN 112, WARRENTON, VA, 2..., Warrenton, VA 20187

$440,000

2 beds

|

2 baths

|

1,754 sq ft

|

Condo

6704 HOLLY FARM LN 112, WARRENTON, VA, 2...

Community: Suffield Meadows

Heritage Hunt

13520 NORWICK PL, GAINESVILLE, VA, 20155, Gainesville, VA 20155

$687,500

3 beds

|

3 baths

|

2,153 sq ft

13520 NORWICK PL, GAINESVILLE, VA, 20155

Community: Heritage Hunt

Trilogy® at Lake Frederick

105 TROUT LILY DR, LAKE FREDERICK, VA, 2..., Lake Frederick, VA 22630

$409,900

3 beds

|

4 baths

|

2,327 sq ft

105 TROUT LILY DR, LAKE FREDERICK, VA, 2...

Community: Trilogy® at Lake Frederick

Trilogy® at Lake Frederick

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

$445,000

3 beds

|

4 baths

|

2,202 sq ft

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

Community: Trilogy® at Lake Frederick

Regency at Ashburn

44605 YORK CREST TER 300, ASHBURN, VA, 2..., Ashburn, VA 20147

$615,000

3 beds

|

2 baths

|

1,825 sq ft

|

Condo

44605 YORK CREST TER 300, ASHBURN, VA, 2...

Community: Regency at Ashburn

Lansdowne Woods of Virginia

19365 CYPRESS RIDGE TER 306, LEESBURG, V..., Leesburg, VA 20176

$365,000

2 beds

|

2 baths

|

1,315 sq ft

|

Condo

19365 CYPRESS RIDGE TER 306, 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

Trilogy® at Lake Frederick

109 TUTELO LN, LAKE FREDERICK, VA, 22630, Lake Frederick, VA 22630

$589,900

2 beds

|

3 baths

|

3,505 sq ft

109 TUTELO LN, LAKE FREDERICK, VA, 22630

Community: Trilogy® at Lake Frederick

The Village at Harvest Ridge

152 HARVEST RIDGE DR, WINCHESTER, VA, 22..., Winchester, VA 22601

$625,000

3 beds

|

2 baths

|

2,444 sq ft

152 HARVEST RIDGE DR, WINCHESTER, VA, 22...

Community: The Village at Harvest Ridge

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.

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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 9 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 161 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 Abrams Chase, Cottage Glen, The Highlands at Blue Ridge Shadows. There are also 3 communities in the Winchester Area that offer new construction homes, including Abrams Chase, Trilogy® at Lake Frederick, Cottage Glen.

Are there gated 55+ communities in the Winchester Area?

Yes, there are gated 55+ communities in the Winchester Area. Approximately 30.0% of 55+ communities in the area are gated. For instance, Cedar Meadows is a gated communities with 129 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 602 days. The average price of homes for sale in these communities is approximately $484,040, though prices can range widely based on the size, location, and amenities of the communities. For example, homes in The Highlands at Blue Ridge Shadows average around $615,000, while homes in Cottage Glen average around $479,500.

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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 11, 2026.
This application does not include information on all of the properties available for sale at this time.

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