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

51 communities near Winchester Area

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Vistas at Lansdowne
$800ks
Vistas at Lansdowne, Lansdowne, VA
Resale Only | 55+ age-restricted | Built 2015 - 2020 | 120 homes
Ballenger Run
$300ks - $400ks
Ballenger Run, Frederick, MD
Resale Only | 55+ age-restricted | Built 2019 - 2020 | 36 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 Villages at Broadland...
$400ks
The Villages at Broadland..., Ashburn, VA
New and Resale | 55+ age-restricted | Built 2013 - present | 78 homes
JerMae Estates
$300ks - $400ks
JerMae Estates, Thurmont, MD
Resale Only | 55+ age-restricted | Built 2003 - 2008 | 108 homes
Want to learn more about 55+ communities in Winchester Area? 55places can help!
Questions? Call us: (540) 452-4199
Want to learn more about 55+ rental communities in Winchester Area? 55places can help!
Questions? Call us: (540) 452-4199
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
Boxwood Villas
$500ks - $600ks
Boxwood Villas, Urbana, MD
Resale Only | 55+ age-restricted | Built 2019 - 2021 | 92 homes
Gatherings at Potomac Sta...
$400ks - $500ks
Gatherings at Potomac Sta..., Leesburg, VA
New Construction | 55+ age-restricted | Built 2023 - 2024 | 55 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.
Read the Ultimate 55+ Rental Guide Thinking about renting in a 55+ active adult community? Our free guide has all the must-know info and practical tips to help you navigate 55+ renting and find your ideal next home in a 55+ community.
Central Parke at Lowes Is...
$300ks - $600ks
Central Parke at Lowes Is..., Sterling, VA
Resale Only | 55+ age-restricted | Built 2003 - 2005 | 181 homes
Regency at Belmont
$600ks - $900ks
Regency at Belmont, Ashburn, VA
New Construction | 55+ age-restricted | Built 2021 - present | 145 homes
Want to learn more about 55+ rental communities in Winchester Area? 55places can help!
Questions? Call us: (540) 452-4199
Want to learn more about 55+ communities in Winchester Area? 55places can help!
Questions? Call us: (540) 452-4199
New 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
New 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
New Heritage Hunt 13490 RYTON RIDGE LN, GAINESVILLE, VA, 2..., Gainesville, VA 20155
$785,000

3 beds

|

3 baths

|

2,800 sq ft

13490 RYTON RIDGE LN, GAINESVILLE, VA, 2...
Community: Heritage Hunt
New 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
New 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
Want to learn more about 55+ communities in Winchester Area? 55places can help!
Questions? Call us: (540) 452-4199
Want to learn more about 55+ rental communities in Winchester Area? 55places can help!
Questions? Call us: (540) 452-4199
New 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...
New 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
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
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...
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.
Read the Ultimate 55+ Rental Guide Thinking about renting in a 55+ active adult community? Our free guide has all the must-know info and practical tips to help you navigate 55+ renting and find your ideal next home in a 55+ community.
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...
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
Gatherings at Wellington 9200 CHARLESTON DR 404, MANASSAS, VA, 20..., Manassas, VA 20110
$398,000

2 beds

|

2 baths

|

1,504 sq ft

|

Condo

9200 CHARLESTON DR 404, MANASSAS, VA, 20...
Montebello 46337 REDDISH KNOB DR, STERLING, VA, 201..., Sterling, VA 20164
$990,000

2 beds

|

2 baths

|

1,812 sq ft

46337 REDDISH KNOB DR, STERLING, VA, 201...
Community: Montebello
Want to learn more about 55+ communities in Winchester Area? 55places can help!
Questions? Call us: (540) 452-4199
The Woodlands of Urbana 3520 STARLIGHT ST 302, FREDERICK, MD, 21..., Frederick, MD 21704
$428,900

2 beds

|

2 baths

|

1,489 sq ft

|

Condo

3520 STARLIGHT ST 302, FREDERICK, MD, 21...
Trilogy® at Lake Frederick 107 CABBAGE WHITE DR, LAKE FREDERICK, VA..., Lake Frederick, VA 22630
$679,950

4 beds

|

4 baths

|

3,190 sq ft

107 CABBAGE WHITE DR, LAKE FREDERICK, VA...
Regency at Creekside 13712 LONG RIDGE DR, GAINESVILLE, VA, 20..., Gainesville, VA 20155
$1,125,000

3 beds

|

3 baths

|

3,146 sq ft

13712 LONG RIDGE DR, GAINESVILLE, VA, 20...
Want to learn more about 55+ rental communities in Winchester Area? 55places can help!
Questions? Call us: (540) 452-4199
Suffield Meadows 6696 CLUB HOUSE LN 104, WARRENTON, VA, 2..., Warrenton, VA 20187
$440,000

3 beds

|

2 baths

|

1,994 sq ft

|

Condo

6696 CLUB HOUSE LN 104, WARRENTON, VA, 2...
Community: Suffield Meadows
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.
Regency at Dominion Valley 15564 LEGACY WAY, HAYMARKET, VA, 20169, Haymarket, VA 20169
$1,048,000

3 beds

|

3 baths

|

4,059 sq ft

15564 LEGACY WAY, HAYMARKET, VA, 20169
Read the Ultimate 55+ Rental Guide Thinking about renting in a 55+ active adult community? Our free guide has all the must-know info and practical tips to help you navigate 55+ renting and find your ideal next home in a 55+ community.
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,...
Trilogy® at Lake Frederick 110 RHODODENDRON CT, LAKE FREDERICK, VA,..., Lake Frederick, VA 22630
$859,990

3 beds

|

3 baths

|

3,725 sq ft

110 RHODODENDRON CT, LAKE FREDERICK, VA,...
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
Want to learn more about 55+ communities in Winchester Area? 55places can help!
Questions? Call us: (540) 452-4199
Trilogy® at Lake Frederick 103 CLOAK LN, LAKE FREDERICK, VA, 22630, Lake Frederick, VA 22630
$649,900

3 beds

|

3 baths

|

2,486 sq ft

103 CLOAK LN, LAKE FREDERICK, VA, 22630
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
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, ...
Potomac Green 44438 CRUDEN BAY DR, ASHBURN, VA, 20147, Ashburn, VA 20147
$739,900

3 beds

|

3 baths

|

2,255 sq ft

44438 CRUDEN BAY DR, ASHBURN, VA, 20147
Community: Potomac Green
Emerald Pointe 13226 ONYX DR, HAGERSTOWN, MD, 21742, Hagerstown, MD 21742
$524,900

2 beds

|

2 baths

13226 ONYX DR, HAGERSTOWN, MD, 21742
Community: Emerald Pointe
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+ 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+
Want to learn more about 55+ rental communities in Winchester Area? 55places can help!
Questions? Call us: (540) 452-4199
Read the Ultimate 55+ Rental Guide Thinking about renting in a 55+ active adult community? Our free guide has all the must-know info and practical tips to help you navigate 55+ renting and find your ideal next home in a 55+ community.
Regency at Dominion Valley 15517 LEGACY WAY, HAYMARKET, VA, 20169, Haymarket, VA 20169
$850,000

3 beds

|

3 baths

|

3,056 sq ft

15517 LEGACY WAY, HAYMARKET, VA, 20169
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...
Want to learn more about 55+ communities in Winchester Area? 55places can help!
Questions? Call us: (540) 452-4199
Crestwood Village 5798 BOX ELDER CT, FREDERICK, MD, 21703, Frederick, MD 21703
$514,950

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...
The Village at Harvest Ridge 153 HARVEST RIDGE DR, WINCHESTER, VA, 22..., Winchester, VA 22601
$649,999

4 beds

|

3 baths

|

3,157 sq ft

153 HARVEST RIDGE DR, WINCHESTER, VA, 22...
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...
Four Seasons at Ashburn Village 44485 CHAMBERLAIN TER 203, ASHBURN, VA, ..., Ashburn, VA 20147
$460,000

2 beds

|

2 baths

|

1,612 sq ft

|

Condo

44485 CHAMBERLAIN TER 203, ASHBURN, VA, ...
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 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,...
The Village at Freedom Hills 13918 PATRIOT WAY, HAGERSTOWN, MD, 21740, Hagerstown, MD 21740
$355,000

2 beds

|

2 baths

|

1,430 sq ft

13918 PATRIOT WAY, HAGERSTOWN, MD, 21740
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...
Read the Ultimate 55+ Rental Guide Thinking about renting in a 55+ active adult community? Our free guide has all the must-know info and practical tips to help you navigate 55+ renting and find your ideal next home in a 55+ community.
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
Want to learn more about 55+ communities in Winchester Area? 55places can help!
Questions? Call us: (540) 452-4199
Want to learn more about 55+ rental 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,...
Willow Run 115 TRELLIS VIEW LN, WINCHESTER, VA, 226..., Winchester, VA 22602
$499,990

4 beds

|

3 baths

|

2,168 sq ft

115 TRELLIS VIEW LN, WINCHESTER, VA, 226...
Community: Willow Run



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

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