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

46 communities near Winchester Area

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5 rating (2 reviews) Trilogy® at Lake Frederic...
$400Ks - $1Ms
Trilogy® at Lake Frederic..., Lake Frederick, VA
New and Resale | 55+ age-restricted | Built 2006 - present | 950 homes
Cedar Meadows
$400Ks
Cedar Meadows, White Post, VA
Resale Only | 55+ age-restricted | Built 2010 - 2022 | 129 homes
5 rating (1 reviews) Willow Lawn Cottages
$300Ks
Willow Lawn Cottages, Winchester, VA
Resale Only | 55+ age-restricted | Built 1999 - 2004 | 120 homes
Cross Creek Village
$300Ks - $400Ks
Cross Creek Village, Winchester, VA
Resale Only | 55+ age-restricted | Built 2001 - 2004 | 90 homes
The Village at Harvest Ri...
$500Ks - $600Ks
The Village at Harvest Ri..., Winchester, VA
Resale Only | 55+ age-restricted | Built 2005 - 2016 | 82 homes
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Questions? Call us: (540) 452-4199
Woodbrook Village
$300Ks
Woodbrook Village, Winchester, VA
Resale Only | 55+ age-restricted | Built 1999 - 2001 | 81 homes
Heritage Highlands
$300Ks - $400Ks
Heritage Highlands, Lovettsville, VA
Resale Only | 55+ age-restricted | Built 2017 - 2020 | 80 homes
The Highlands at Blue Rid...
$400Ks - $700Ks
The Highlands at Blue Rid..., Front Royal, VA
Resale Only | 55+ age-restricted | Built 2017 - 2019 | 42 homes
Cottage Glen
$400Ks
Cottage Glen, Winchester, VA
New and Resale | Age-targeted | Built 2018 - present | 25 homes
Abrams Chase
$500Ks
Abrams Chase, Winchester, VA
New Construction | 55+ age-restricted | Built 2020 - present | 13 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 (3 reviews) Heritage Hunt
$400Ks - $800Ks
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
5 rating (2 reviews) Potomac Green
$700Ks - $800Ks
Potomac Green, Ashburn, VA
Resale Only | 55+ age-restricted | Built 2005 - 2016 | 1,400 homes
5 rating (31 reviews) Lansdowne Woods of Virgin...
$200Ks - $400Ks
Lansdowne Woods of Virgin..., Lansdowne, VA
Resale Only | 55+ age-restricted | Built 1998 - 2017 | 1,200 homes
5 rating (1 reviews) Regency at Dominion Valle...
$400Ks - $700Ks
Regency at Dominion Valle..., Haymarket, VA
Resale Only | 55+ age-restricted | Built 2001 - 2017 | 855 homes
Want to learn more about 55+ communities in Winchester Area? 55places can help!
Questions? Call us: (540) 452-4199
The Woodlands of Urbana
$600Ks
The Woodlands of Urbana, Urbana, MD
New Construction | 55+ age-restricted | Built 2019 - present | 565 homes
5 rating (1 reviews) Crestwood Village
$300Ks
Crestwood Village, Frederick, MD
Resale Only | 55+ age-restricted | Built 1979 - 1999 | 550 homes
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
$600Ks
Dunbarton, Bristow, VA
Resale Only | 55+ age-restricted | Built 2000 - 2009 | 479 homes
Montebello
$600Ks - $1Ms
Montebello, Sterling, VA
New and Resale | 55+ age-restricted | Built 2022 - present | 450 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.
Regency at Ashburn
$800Ks - $900Ks
Regency at Ashburn, Ashburn, VA
Resale Only | 55+ age-restricted | Built 2013 - 2020 | 268 homes
Emerald Pointe
$300Ks - $400Ks
Emerald Pointe, Hagerstown, MD
New and Resale | 55+ age-restricted | Built 2008 - present | 250 homes
The Retreat at Poland Hil...
$700Ks - $900Ks
The Retreat at Poland Hil..., Chantilly, VA
Resale Only | 55+ age-restricted | Built 2020 - 2022 | 219 homes
Regency at Creekside
$900Ks
Regency at Creekside, Gainesville, VA
Resale Only | 55+ age-restricted | Built 2016 - 2020 | 208 homes
Central Parke at Lowes Is...
$400Ks - $700Ks
Central Parke at Lowes Is..., Sterling, VA
Resale Only | 55+ age-restricted | Built 2003 - 2005 | 181 homes
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Questions? Call us: (540) 452-4199
Regency at Belmont
$900Ks
Regency at Belmont, Ashburn, VA
New Construction | 55+ age-restricted | Built 2021 - present | 145 homes
5 rating (1 reviews) Gatherings at Wellington
$300Ks - $400Ks
Gatherings at Wellington, Manassas, VA
Resale Only | 55+ age-restricted | Built 2011 - 2016 | 135 homes
Vistas at Lansdowne
$500Ks - $800Ks
Vistas at Lansdowne, Lansdowne, VA
Resale Only | 55+ age-restricted | Built 2015 - 2020 | 120 homes
Lexington 7
$800Ks
Lexington 7, Ashburn, VA
Resale Only | 55+ age-restricted | Built 2017 - 2020 | 113 homes
Suffield Meadows
$300Ks - $400Ks
Suffield Meadows, Warrenton, VA
Resale Only | 55+ age-restricted | Built 2005 - 2011 | 112 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.
JerMae Estates
$400Ks - $500Ks
JerMae Estates, Thurmont, MD
Resale Only | 55+ age-restricted | Built 2003 - 2008 | 108 homes
Albert Courts
$100Ks - $200Ks
Albert Courts, Thurmont, MD
Resale Only | 55+ age-restricted | Built 1991 - 2001 | 100 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
Boxwood Villas
$500Ks - $600Ks
Boxwood Villas, Urbana, MD
Resale Only | 55+ age-restricted | Built 2019 - 2021 | 92 homes
The Village at Foxfield
$500Ks
The Village at Foxfield, Middletown, MD
Resale Only | 55+ age-restricted | Built 2003 - 2012 | 81 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...
$400Ks
Four Seasons at Ashburn V..., Ashburn, VA
Resale Only | 55+ age-restricted | Built 2005 - 2005 | 80 homes
The Villages at Broadland...
$400Ks
The Villages at Broadland..., Ashburn, VA
New and Resale | 55+ age-restricted | Built 2013 - present | 78 homes
Cadence at Lansdowne
$700Ks
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
CobbleStone Estates
$400Ks - $500Ks
CobbleStone Estates, Hagerstown, MD
New and Resale | 55+ age-restricted | Built 2015 - present | 66 homes
1...2
New Albert Courts 215 STULL CT, THURMONT, MD, 21788, Thurmont, MD 21788
$305,000

3 beds

|

3 baths

|

1,532 sq ft

215 STULL CT, THURMONT, MD, 21788
Community: Albert Courts
The Village at Freedom Hills 13946 PATRIOT WAY, HAGERSTOWN, MD, 21740, Hagerstown, MD 21740
$379,900

2 beds

|

2 baths

|

1,484 sq ft

13946 PATRIOT WAY, HAGERSTOWN, MD, 21740
Emerald Pointe 13336 MARQUISE DR, HAGERSTOWN, MD, 21742, Hagerstown, MD 21742
$424,900

2 beds

|

2 baths

|

2,615 sq ft

13336 MARQUISE DR, HAGERSTOWN, MD, 21742
Community: Emerald Pointe
The Woodlands of Urbana 3207 THORNAPPLE DR, FREDERICK, MD, 21704, Frederick, MD 21704
$609,900

3 beds

|

3 baths

|

1,677 sq ft

3207 THORNAPPLE DR, FREDERICK, MD, 21704
New Crestwood Village 6905 CHOKEBERRY CT, FREDERICK, MD, 21703, Frederick, MD 21703
$334,900

2 beds

|

1 baths

|

1,160 sq ft

6905 CHOKEBERRY CT, FREDERICK, MD, 21703
Community: Crestwood Village
Want to learn more about 55+ communities in Winchester Area? 55places can help!
Questions? Call us: (540) 452-4199
The Woodlands of Urbana 3225 THORNAPPLE DR, FREDERICK, MD, 21704, Frederick, MD 21704
$615,000

3 beds

|

3 baths

|

1,816 sq ft

3225 THORNAPPLE DR, FREDERICK, MD, 21704
Crestwood Village 5722 BOX ELDER CT, FREDERICK, MD, 21703, Frederick, MD 21703
$349,000

2 beds

|

2 baths

|

1,264 sq ft

5722 BOX ELDER CT, FREDERICK, MD, 21703
Community: Crestwood Village
CobbleStone Estates 9616 COBBLE STONE CT, HAGERSTOWN, MD, 21..., Hagerstown, MD 21740
$395,000

2 beds

|

2 baths

|

1,561 sq ft

9616 COBBLE STONE CT, HAGERSTOWN, MD, 21...
Community: CobbleStone Estates
The Village at Foxfield 1 KELLER LN, MIDDLETOWN, MD, 21769, Middletown, MD 21769
$574,900

3 beds

|

3 baths

|

3,161 sq ft

1 KELLER LN, MIDDLETOWN, MD, 21769
Crestwood Village 7043 BASSWOOD RD, FREDERICK, MD, 21703, Frederick, MD 21703
$339,999

2 beds

|

2 baths

|

1,225 sq ft

7043 BASSWOOD RD, FREDERICK, MD, 21703
Community: Crestwood Village
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.
The Woodlands of Urbana 2928 HERB GARDEN DR, FREDERICK, MD, 2170..., Frederick, MD 21704
$725,000

3 beds

|

4 baths

|

3,634 sq ft

2928 HERB GARDEN DR, FREDERICK, MD, 2170...
Emerald Pointe 19446 SAPPHIRE DR, HAGERSTOWN, MD, 21742, Hagerstown, MD 21742
$359,900

2 beds

|

2 baths

|

1,834 sq ft

19446 SAPPHIRE DR, HAGERSTOWN, MD, 21742
Community: Emerald Pointe
Emerald Pointe 13430 MARQUISE DR # 80, HAGERSTOWN, MD, ..., Hagerstown, MD 21742
$429,000

2 beds

|

3 baths

|

2,739 sq ft

13430 MARQUISE DR # 80, HAGERSTOWN, MD, ...
Community: Emerald Pointe
Emerald Pointe 19554 TURQUOISE DR V219, HAGERSTOWN, MD,..., Hagerstown, MD 21742
$484,900

2 beds

|

2 baths

19554 TURQUOISE DR V219, HAGERSTOWN, MD,...
Community: Emerald Pointe
New Regency at Dominion Valley 15110 HEATHER MILL LN APT 201, HAYMARKET..., Haymarket, VA 20169
$469,000

2 beds

|

2 baths

|

1,551 sq ft

|

Condo

15110 HEATHER MILL LN APT 201, HAYMARKET...
Want to learn more about 55+ communities in Winchester Area? 55places can help!
Questions? Call us: (540) 452-4199
Birchwood at Brambleton 43011 DEBONAIR TER, ASHBURN, VA, 20148, Ashburn, VA 20148
$881,202

3 beds

|

4 baths

|

2,742 sq ft

43011 DEBONAIR TER, ASHBURN, VA, 20148
Birchwood at Brambleton 43016 DEBONAIR TER, ASHBURN, VA, 20148, Ashburn, VA 20148
$881,457

3 beds

|

4 baths

|

2,742 sq ft

43016 DEBONAIR TER, ASHBURN, VA, 20148
Birchwood at Brambleton 43089 GREELEY SQ, ASHBURN, VA, 20148, Ashburn, VA 20148
$969,990

3 beds

|

3 baths

|

2,491 sq ft

43089 GREELEY SQ, ASHBURN, VA, 20148
Birchwood at Brambleton 1 HARDESTY TER, ASHBURN, VA, 20148, Ashburn, VA 20148
$734,990

3 beds

|

3 baths

|

2,742 sq ft

1 HARDESTY TER, ASHBURN, VA, 20148
Birchwood at Brambleton 42972 TRUMAN TER, ASHBURN, VA, 20148, Ashburn, VA 20148
$853,586

4 beds

|

4 baths

|

2,742 sq ft

42972 TRUMAN TER, ASHBURN, VA, 20148
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 15691 ALDERBROOK DR, HAYMARKET, VA, 2016..., Haymarket, VA 20169
$849,900

2 beds

|

3 baths

|

4,124 sq ft

15691 ALDERBROOK DR, HAYMARKET, VA, 2016...
Cadence at Lansdowne 43899 SIREN SONG TER, LEESBURG, VA, 2017..., Leesburg, VA 20176
$785,000

3 beds

|

4 baths

|

2,780 sq ft

43899 SIREN SONG TER, LEESBURG, VA, 2017...
Regency at Dominion Valley 15428 CHAMPIONSHIP DR, HAYMARKET, VA, 20..., Haymarket, VA 20169
$750,000

3 beds

|

3 baths

|

3,309 sq ft

15428 CHAMPIONSHIP DR, HAYMARKET, VA, 20...
New Birchwood at Brambleton 23606 HAVELOCK WALK TER, ASHBURN, VA, 20..., Ashburn, VA 20148
$585,000

3 beds

|

3 baths

|

2,592 sq ft

|

Condo

23606 HAVELOCK WALK TER, ASHBURN, VA, 20...
Lansdowne Woods of Virginia 19375 CYPRESS RIDGE TER UNIT 708, LEESBU..., Leesburg, VA 20176
$419,900

2 beds

|

2 baths

|

1,315 sq ft

|

Condo

19375 CYPRESS RIDGE TER UNIT 708, LEESBU...
Want to learn more about 55+ communities in Winchester Area? 55places can help!
Questions? Call us: (540) 452-4199
Lansdowne Woods of Virginia 19375 CYPRESS RIDGE TER 207, LEESBURG, V..., Leesburg, VA 20176
$419,900

2 beds

|

2 baths

|

1,380 sq ft

|

Condo

19375 CYPRESS RIDGE TER 207, LEESBURG, V...
Trilogy® at Lake Frederick 108 BUNTING CT, LAKE FREDERICK, VA, 2263..., Lake Frederick, VA 22630
$745,000

3 beds

|

4 baths

|

5,284 sq ft

108 BUNTING CT, LAKE FREDERICK, VA, 2263...
Trilogy® at Lake Frederick 102 PHOEBE CT, LAKE FREDERICK, VA, 22630, Lake Frederick, VA 22630
$915,000

5 beds

|

4 baths

|

4,267 sq ft

102 PHOEBE CT, LAKE FREDERICK, VA, 22630
Trilogy® at Lake Frederick 103 PLANETREE CT, LAKE FREDERICK, VA, 22..., Lake Frederick, VA 22630
$825,000

3 beds

|

3 baths

|

3,589 sq ft

103 PLANETREE CT, LAKE FREDERICK, VA, 22...
Lansdowne Woods of Virginia 19385 CYPRESS RIDGE TER UNIT 907, LEESBU..., Leesburg, VA 20176
$285,000

1 beds

|

1 baths

|

874 sq ft

|

Condo

19385 CYPRESS RIDGE TER UNIT 907, LEESBU...
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.
Heritage Hunt 13612 RYTON RIDGE LN, GAINESVILLE, VA, 2..., Gainesville, VA 20155
$864,997

4 beds

|

3 baths

|

4,486 sq ft

13612 RYTON RIDGE LN, GAINESVILLE, VA, 2...
Community: Heritage Hunt
Regency at Ashburn 44557 GRANITE RUN TER, ASHBURN, VA, 2014..., Ashburn, VA 20147
$845,000

3 beds

|

3 baths

|

4,208 sq ft

44557 GRANITE RUN TER, ASHBURN, VA, 2014...
Community: Regency at Ashburn
Heritage Hunt 13154 TRIPLE CROWN LOOP, GAINESVILLE, VA..., Gainesville, VA 20155
$725,000

3 beds

|

4 baths

|

3,195 sq ft

13154 TRIPLE CROWN LOOP, GAINESVILLE, VA...
Community: Heritage Hunt
Heritage Hunt 6159 FERRIER CT, GAINESVILLE, VA, 20155, Gainesville, VA 20155
$800,000

3 beds

|

3 baths

|

2,846 sq ft

6159 FERRIER CT, GAINESVILLE, VA, 20155
Community: Heritage Hunt
Birchwood at Brambleton 42783 FIREFLY SONATA TER, ASHBURN, VA, 2..., Ashburn, VA 20148
$760,000

2 beds

|

3 baths

|

2,406 sq ft

42783 FIREFLY SONATA TER, ASHBURN, VA, 2...
Want to learn more about 55+ communities in Winchester Area? 55places can help!
Questions? Call us: (540) 452-4199
Potomac Green 44420 SUNSET MAPLE DR, ASHBURN, VA, 2014..., Ashburn, VA 20147
$749,000

3 beds

|

3 baths

|

2,447 sq ft

44420 SUNSET MAPLE DR, ASHBURN, VA, 2014...
Community: Potomac Green
Four Seasons at Ashburn Village 44465 CHAMBERLAIN TER UNIT 103, ASHBURN,..., Ashburn, VA 20147
$429,900

2 beds

|

2 baths

|

1,612 sq ft

|

Condo

44465 CHAMBERLAIN TER UNIT 103, ASHBURN,...
Heritage Hunt 17680 GLASS RIDGE PL, GAINESVILLE, VA, 2..., Gainesville, VA 20155
$650,000

3 beds

|

3 baths

|

2,920 sq ft

17680 GLASS RIDGE PL, GAINESVILLE, VA, 2...
Community: Heritage Hunt
Regency at Dominion Valley 15100 HEATHER MILL LN APT 407, HAYMARKET..., Haymarket, VA 20169
$450,000

2 beds

|

2 baths

|

1,538 sq ft

|

Condo

15100 HEATHER MILL LN APT 407, HAYMARKET...
Birchwood at Brambleton 23688 BOLTON CRESCENT TER APT 204, ASHBU..., Ashburn, VA 20148
$470,000

2 beds

|

2 baths

|

1,280 sq ft

|

Condo

23688 BOLTON CRESCENT TER APT 204, ASHBU...



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46 communities near Winchester Area
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