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

205 homes near Winchester Area

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5 rating (2 reviews)

Trilogy® at Lake Frederic...

- $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

Willow Run

$500ks - $600ks

Willow Run, Winchester, VA

New Construction | 55+ age-restricted | 300 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

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

Emerald Pointe

$300ks - $500ks

Emerald Pointe, Hagerstown, MD

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

5 rating (2 reviews)

Potomac Green

$400ks - $800ks

Potomac Green, Ashburn, VA

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

The Woodlands of Urbana

$500ks - $700ks

The Woodlands of Urbana, Urbana, MD

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

5 rating (1 reviews)

Gatherings at Wellington

$300ks - $400ks

Gatherings at Wellington, Manassas, VA

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

Rosehill Manor Villas

$300ks

Rosehill Manor Villas, Hagerstown, MD

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

Cadence at Lansdowne

$600ks

Cadence at Lansdowne, Lansdowne, VA

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

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

Questions? Call us: (540) 452-4199

5 rating (1 reviews)

Crestwood Village

$200ks - $500ks

Crestwood Village, Frederick, MD

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

Liberty Grove

$200ks - $300ks

Liberty Grove, Manassas, VA

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

Winchester Landing

$300ks - $400ks

Winchester Landing, Winchester, VA

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

Robinson Manor

$600ks - $700ks

Robinson Manor, Gainesville, VA

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

Lexington Square

$800ks - $1Ms

Lexington Square, Ashburn, VA

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

Montebello

$500ks - $900ks

Montebello, Sterling, VA

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

Woodbrook Village

$200ks - $300ks

Woodbrook Village, Winchester, VA

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

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

Questions? Call us: (540) 452-4199

The Village at Harvest Ri...

$400ks - $500ks

The Village at Harvest Ri..., Winchester, VA

Resale Only | 55+ age-restricted | Built 2005 - 2016 | 82 homes

Cross Creek Village

$300ks

Cross Creek Village, Winchester, VA

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

Cedar Meadows

$300ks - $400ks

Cedar Meadows, White Post, VA

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

Regency at Ashburn

$300ks - $800ks

Regency at Ashburn, Ashburn, VA

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

5 rating (1 reviews)

Willow Lawn Cottages

$300ks

Willow Lawn Cottages, Winchester, VA

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

3 rating (2 reviews)

Dunbarton

$300ks - $500ks

Dunbarton, Bristow, VA

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

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

Questions? Call us: (540) 452-4199

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

Cottage Glen

$400ks

Cottage Glen, Winchester, VA

New and Resale | Age-targeted | Built 2018 - present | 25 homes

Lexington 7

$600ks - $700ks

Lexington 7, Ashburn, VA

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

The Retreat at Poland Hil...

$800ks

The Retreat at Poland Hil..., Chantilly, VA

Resale Only | 55+ age-restricted | Built 2020 - 2022 | 219 homes

Abrams Chase

$400ks - $500ks

Abrams Chase, Winchester, VA

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

The Village at Foxfield

$300ks - $500ks

The Village at Foxfield, Middletown, MD

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

Boxwood Villas

$500ks - $600ks

Boxwood Villas, Urbana, MD

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

Suffield Meadows

$400ks

Suffield Meadows, Warrenton, VA

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

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

Questions? Call us: (540) 452-4199

Heritage Highlands

$300ks - $400ks

Heritage Highlands, Lovettsville, VA

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

JerMae Estates

$300ks - $400ks

JerMae Estates, Thurmont, MD

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

1...2

Cedar Meadows

108 TRUMPET VINE DR, WHITE POST, VA, 226..., White Post, VA 22663

$464,900

3 beds

2 baths

1,639 sq ft

108 TRUMPET VINE DR, WHITE POST, VA, 226...

Community: Cedar Meadows

The Highlands at Blue Ridge Shadows

18 ALBATROSS CT, FRONT ROYAL, VA, 22630, Front Royal, VA 22630

$689,900

4 beds

4 baths

3,861 sq ft

18 ALBATROSS CT, FRONT ROYAL, VA, 22630

Community: The Highlands at Blue Ridge Shadows

Winchester Landing

101 MAURY, WINCHESTER, VA, 22602, Winchester, VA 22602

$385,000

3 beds

3 baths

1,505 sq ft

101 MAURY, WINCHESTER, VA, 22602

Community: Winchester Landing

The Village at Freedom Hills

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

$499,900

4 beds

2 baths

3,107 sq ft

13862 PATRIOT WAY, HAGERSTOWN, MD, 21740

Community: The Village at Freedom Hills

The Woodlands of Urbana

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

$430,000

2 beds

2 baths

Condo

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

Community: The Woodlands of Urbana

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

Questions? Call us: (540) 452-4199

Rosehill Manor Villas

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

$384,900

2 beds

2 baths

1,735 sq ft

19601 LAVENDER LN, HAGERSTOWN, MD, 21742

Community: Rosehill Manor Villas

Birchwood at Brambleton

43059 GREELEY SQ, ASHBURN, VA, 20148, Ashburn, VA 20148

$1,050,000

3 beds

3 baths

2,570 sq ft

43059 GREELEY SQ, ASHBURN, VA, 20148

Community: Birchwood at Brambleton

Lansdowne Woods of Virginia

19365 CYPRESS RIDGE TER 510, LEESBURG, V..., Leesburg, VA 20176

$435,000

2 beds

2 baths

1,251 sq ft

Condo

19365 CYPRESS RIDGE TER 510, LEESBURG, V...

Community: Lansdowne Woods of Virginia

Cadence at Lansdowne

43887 SIREN SONG TER, LEESBURG, VA, 2017..., Leesburg, VA 20176

$739,900

4 beds

4 baths

2,642 sq ft

43887 SIREN SONG TER, LEESBURG, VA, 2017...

Community: Cadence at Lansdowne

Cadence at Lansdowne

19006 CORAL REEF SQ, LEESBURG, VA, 20176, Leesburg, VA 20176

$959,900

3 beds

5 baths

3,679 sq ft

19006 CORAL REEF SQ, LEESBURG, VA, 20176

Community: Cadence at Lansdowne

Gatherings at Wellington

9200 CHARLESTON DR 404, MANASSAS, VA, 20..., Manassas, VA 20110

$389,000

2 beds

2 baths

1,504 sq ft

Condo

9200 CHARLESTON DR 404, MANASSAS, VA, 20...

Community: Gatherings at Wellington

Montebello

46337 REDDISH KNOB DR, STERLING, VA, 201..., Sterling, VA 20164

$935,000

2 beds

2 baths

2,212 sq ft

46337 REDDISH KNOB DR, STERLING, VA, 201...

Community: Montebello

The Woodlands of Urbana

3520 STARLIGHT ST 302, FREDERICK, MD, 21..., Frederick, MD 21704

$424,900

2 beds

2 baths

1,489 sq ft

Condo

3520 STARLIGHT ST 302, FREDERICK, MD, 21...

Community: The Woodlands of Urbana

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

Questions? Call us: (540) 452-4199

Trilogy® at Lake Frederick

107 CABBAGE WHITE DR, LAKE FREDERICK, VA..., Lake Frederick, VA 22630

$669,500

4 beds

4 baths

3,190 sq ft

107 CABBAGE WHITE DR, LAKE FREDERICK, VA...

Community: Trilogy® at Lake Frederick

Trilogy® at Lake Frederick

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

$769,990

2 beds

2 baths

2,058 sq ft

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

Community: Trilogy® at Lake Frederick

The Village at Freedom Hills

13880 PATRIOT WAY, HAGERSTOWN, MD, 21740, Hagerstown, MD 21740

$390,000

2 beds

2 baths

1,543 sq ft

13880 PATRIOT WAY, HAGERSTOWN, MD, 21740

Community: The Village at Freedom Hills

Trilogy® at Lake Frederick

103 CLOAK LN, LAKE FREDERICK, VA, 22630, Lake Frederick, VA 22630

$624,900

3 beds

3 baths

2,486 sq ft

103 CLOAK LN, LAKE FREDERICK, VA, 22630

Community: Trilogy® at Lake Frederick

Willow Lawn Cottages

1851 MELVOR LN, WINCHESTER, VA, 22601, Winchester, VA 22601

$399,900

2 beds

2 baths

1,405 sq ft

1851 MELVOR LN, WINCHESTER, VA, 22601

Community: Willow Lawn Cottages

Lansdowne Woods of Virginia

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

$539,000

3 beds

2 baths

1,475 sq ft

Condo

19365 CYPRESS RIDGE TER 1115, LEESBURG, ...

Community: Lansdowne Woods of Virginia

Bloomfields 55+

2605 BROADLEAF DR, FREDERICK, MD, 21702, Frederick, MD 21702

$849,900

3 beds

4 baths

3,462 sq ft

2605 BROADLEAF DR, FREDERICK, MD, 21702

Community: Bloomfields 55+

Regency at Dominion Valley

15517 LEGACY WAY, HAYMARKET, VA, 20169, Haymarket, VA 20169

$840,000

3 beds

3 baths

3,056 sq ft

15517 LEGACY WAY, HAYMARKET, VA, 20169

Community: Regency at Dominion Valley

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

Questions? Call us: (540) 452-4199

Gatherings at Wellington

9202 CHARLESTON DR 405, MANASSAS, VA, 20..., Manassas, VA 20110

$355,000

2 beds

2 baths

1,504 sq ft

Condo

9202 CHARLESTON DR 405, MANASSAS, VA, 20...

Community: Gatherings at Wellington

Crestwood Village

5798 BOX ELDER CT, FREDERICK, MD, 21703, Frederick, MD 21703

$469,500

2 beds

2 baths

2,044 sq ft

5798 BOX ELDER CT, FREDERICK, MD, 21703

Community: Crestwood Village

Birchwood at Brambleton

23716 SEPTEMBER SUN SQ, ASHBURN, VA, 201..., Ashburn, VA 20148

$719,900

3 beds

3 baths

2,258 sq ft

23716 SEPTEMBER SUN SQ, ASHBURN, VA, 201...

Community: Birchwood at Brambleton

The Village at Harvest Ridge

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

$642,900

4 beds

3 baths

3,157 sq ft

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

Community: The Village at Harvest Ridge

Lansdowne Woods of Virginia

19385 CYPRESS RIDGE TER 510, LEESBURG, V..., Leesburg, VA 20176

$490,000

3 beds

2 baths

1,475 sq ft

Condo

19385 CYPRESS RIDGE TER 510, LEESBURG, V...

Community: Lansdowne Woods of Virginia

Birchwood at Brambleton

23669 GOLDEN EMBERS SQ 204, ASHBURN, VA,..., Ashburn, VA 20148

$485,000

2 beds

2 baths

1,280 sq ft

Condo

23669 GOLDEN EMBERS SQ 204, ASHBURN, VA,...

Community: Birchwood at Brambleton

Lansdowne Woods of Virginia

19355 CYPRESS RIDGE TER 802, LEESBURG, V..., Leesburg, VA 20176

$495,000

3 beds

2 baths

1,560 sq ft

Condo

19355 CYPRESS RIDGE TER 802, LEESBURG, V...

Community: Lansdowne Woods of Virginia

Birchwood at Brambleton

23695 HARDESTY TER, ASHBURN, VA, 20148, Ashburn, VA 20148

$994,990

2 beds

3 baths

2,742 sq ft

23695 HARDESTY TER, ASHBURN, VA, 20148

Community: Birchwood at Brambleton

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

Questions? Call us: (540) 452-4199

Trilogy® at Lake Frederick

109 SONG SPARROW DR, LAKE FREDERICK, VA,..., Lake Frederick, VA 22630

$639,990

2 beds

2 baths

2,054 sq ft

109 SONG SPARROW DR, LAKE FREDERICK, VA,...

Community: Trilogy® at Lake Frederick

The Woodlands of Urbana

2821 CAMOMILE DR, FREDERICK, MD, 21704, Frederick, MD 21704

$900,000

3 beds

3 baths

2,762 sq ft

2821 CAMOMILE DR, FREDERICK, MD, 21704

Community: The Woodlands of Urbana

Cross Creek Village

105 CRANBERRY CT, WINCHESTER, VA, 22602, Winchester, VA 22602

$379,900

2 beds

2 baths

1,698 sq ft

105 CRANBERRY CT, WINCHESTER, VA, 22602

Community: Cross Creek Village

The Retreat at Poland Hill

25635 NOT FORGOTTEN TER, CHANTILLY, VA, ..., Chantilly, VA 20152

$775,000

3 beds

3 baths

2,442 sq ft

25635 NOT FORGOTTEN TER, CHANTILLY, VA, ...

Community: The Retreat at Poland Hill

Birchwood at Brambleton

42881 LITTLEHALES TER, ASHBURN, VA, 2014..., Ashburn, VA 20148

$589,000

3 beds

3 baths

2,580 sq ft

Condo

42881 LITTLEHALES TER, ASHBURN, VA, 2014...

Community: Birchwood at Brambleton

Heritage Hunt

6116 PINEY GROVE WAY, GAINESVILLE, VA, 2..., Gainesville, VA 20155

$764,000

4 beds

3 baths

2,806 sq ft

6116 PINEY GROVE WAY, GAINESVILLE, VA, 2...

Community: Heritage Hunt

Lansdowne Woods of Virginia

19355 CYPRESS RIDGE TER 1122, LEESBURG, ..., Leesburg, VA 20176

$375,000

2 beds

2 baths

1,038 sq ft

Condo

19355 CYPRESS RIDGE TER 1122, LEESBURG, ...

Community: Lansdowne Woods of Virginia

Trilogy® at Lake Frederick

107 YELLOW BIRCH, LAKE FREDERICK, VA, 22..., Lake Frederick, VA 22630

$969,999

3 beds

5 baths

4,465 sq ft

107 YELLOW BIRCH, LAKE FREDERICK, VA, 22...

Community: Trilogy® at Lake Frederick

Albert Courts

5 SPANGLER CT, THURMONT, MD, 21788, Thurmont, MD 21788

$329,900

3 beds

3 baths

1,720 sq ft

5 SPANGLER CT, THURMONT, MD, 21788

Community: Albert Courts

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

Questions? Call us: (540) 452-4199

Trilogy® at Lake Frederick

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

$435,000

4 beds

4 baths

2,508 sq ft

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

Community: Trilogy® at Lake Frederick

The Woodlands of Urbana

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

$567,000

3 beds

3 baths

1,817 sq ft

3264 STARLIGHT ST, FREDERICK, MD, 21704

Community: The Woodlands of Urbana

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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 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.

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

Insights and market stats
Instant new home alerts
Answers from local 55+ experts

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

Call us: (540) 452-4199

205 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: Apr 11, 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 3

51 communities near Winchester Area

205 homes near Winchester Area

3 beds

2 baths

1,639 sq ft

4 beds

4 baths

3,861 sq ft

3 beds

3 baths

1,505 sq ft

4 beds

2 baths

3,107 sq ft

2 beds

2 baths

Condo

2 beds

2 baths

1,735 sq ft

3 beds

3 baths

2,570 sq ft

2 beds

2 baths

1,251 sq ft

Condo

4 beds

4 baths

2,642 sq ft

3 beds

5 baths

3,679 sq ft

2 beds

2 baths

1,504 sq ft

Condo

2 beds

2 baths

2,212 sq ft

2 beds

2 baths

1,489 sq ft

Condo

4 beds

4 baths

3,190 sq ft

2 beds

2 baths

2,058 sq ft

2 beds

2 baths

1,543 sq ft

3 beds

3 baths

2,486 sq ft

2 beds

2 baths

1,405 sq ft

3 beds

2 baths

1,475 sq ft

Condo

3 beds

4 baths

3,462 sq ft

3 beds

3 baths

3,056 sq ft

2 beds

2 baths

1,504 sq ft

Condo

2 beds

2 baths

2,044 sq ft

3 beds

3 baths

2,258 sq ft