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

129 homes near Winchester Area

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5 rating (2 reviews) Trilogy® at Lake Frederic...
$400Ks - $800Ks
Trilogy® at Lake Frederic..., Lake Frederick, VA
New and Resale | 55+ age-restricted | Built 2006 - present | 950 homes
No reviews yet Cedar Meadows
$400Ks - $400Ks
Cedar Meadows, White Post, VA
Resale Only | 55+ age-restricted | Built 2010 - 2022 | 129 homes
5 rating (1 reviews) Willow Lawn Cottages
$300Ks - $300Ks
Willow Lawn Cottages, Winchester, VA
Resale Only | 55+ age-restricted | Built 1999 - 2004 | 120 homes
No reviews yet Cross Creek Village
$400Ks - $400Ks
Cross Creek Village, Winchester, VA
Resale Only | 55+ age-restricted | Built 2001 - 2004 | 90 homes
No reviews yet The Village at Harvest Ri...
$500Ks - $500Ks
The Village at Harvest Ri..., Winchester, VA
Resale Only | 55+ age-restricted | Built 2005 - 2016 | 82 homes
Want to learn more about 55+ communities in Winchester Area? 55places can help!
Questions? Call us: (540) 452-4199
No reviews yet Woodbrook Village
$300Ks - $300Ks
Woodbrook Village, Winchester, VA
Resale Only | 55+ age-restricted | Built 1999 - 2001 | 81 homes
No reviews yet Heritage Highlands
$300Ks - $400Ks
Heritage Highlands, Lovettsville, VA
Resale Only | 55+ age-restricted | Built 2017 - 2020 | 80 homes
No reviews yet 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
No reviews yet Cottage Glen
$400Ks - $400Ks
Cottage Glen, Winchester, VA
New and Resale | Age-targeted | Built 2018 - present | 25 homes
No reviews yet Abrams Chase
$500Ks - $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
$300Ks - $800Ks
Heritage Hunt, Gainesville, VA
Resale Only | 55+ age-restricted | Built 1998 - 2009 | 1,863 homes
2 rating (1 reviews) Birchwood at Brambleton
$400Ks - $900Ks
Birchwood at Brambleton, Ashburn, VA
New and Resale | 55+ age-restricted | Built 2016 - present | 1,502 homes
5 rating (2 reviews) Potomac Green
$300Ks - $900Ks
Potomac Green, Ashburn, VA
Resale Only | 55+ age-restricted | Built 2005 - 2016 | 1,400 homes
5 rating (31 reviews) Lansdowne Woods of Virgin...
$300Ks - $500Ks
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 - $800Ks
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
No reviews yet The Woodlands of Urbana
$400Ks - $900Ks
The Woodlands of Urbana, Urbana, MD
New Construction | 55+ age-restricted | Built 2019 - present | 565 homes
5 rating (1 reviews) Crestwood Village
$300Ks - $300Ks
Crestwood Village, Frederick, MD
Resale Only | 55+ age-restricted | Built 1979 - 1999 | 550 homes
No reviews yet Carter's Mill
$400Ks - $700Ks
Carter's Mill, Haymarket, VA
New Construction | 55+ age-restricted | Built 2020 - present | 480 homes
1 rating (1 reviews) Dunbarton
$600Ks - $600Ks
Dunbarton, Bristow, VA
Resale Only | 55+ age-restricted | Built 2000 - 2009 | 479 homes
No reviews yet 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.
No reviews yet Regency at Ashburn
$600Ks - $600Ks
Regency at Ashburn, Ashburn, VA
Resale Only | 55+ age-restricted | Built 2013 - 2020 | 268 homes
No reviews yet Emerald Pointe
$300Ks - $400Ks
Emerald Pointe, Hagerstown, MD
New and Resale | 55+ age-restricted | Built 2008 - present | 250 homes
No reviews yet The Retreat at Poland Hil...
$700Ks - $900Ks
The Retreat at Poland Hil..., Chantilly, VA
Resale Only | 55+ age-restricted | Built 2020 - 2022 | 219 homes
No reviews yet Regency at Creekside
$900Ks - $900Ks
Regency at Creekside, Gainesville, VA
Resale Only | 55+ age-restricted | Built 2016 - 2020 | 208 homes
No reviews yet Central Parke at Lowes Is...
$400Ks - $500Ks
Central Parke at Lowes Is..., Sterling, VA
Resale Only | 55+ age-restricted | Built 2003 - 2005 | 181 homes
Want to learn more about 55+ communities in Winchester Area? 55places can help!
Questions? Call us: (540) 452-4199
No reviews yet Regency at Belmont
$900Ks - $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
No reviews yet Vistas at Lansdowne
$500Ks - $800Ks
Vistas at Lansdowne, Lansdowne, VA
Resale Only | 55+ age-restricted | Built 2015 - 2020 | 120 homes
No reviews yet Lexington 7
$700Ks - $900Ks
Lexington 7, Ashburn, VA
Resale Only | 55+ age-restricted | Built 2017 - 2020 | 113 homes
No reviews yet Suffield Meadows
$400Ks - $500Ks
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.
No reviews yet JerMae Estates
$300Ks - $400Ks
JerMae Estates, Thurmont, MD
Resale Only | 55+ age-restricted | Built 2003 - 2008 | 108 homes
5 rating (1 reviews) Four Seasons at Vint Hill
$600Ks - $600Ks
Four Seasons at Vint Hill, Warrenton, VA
Resale Only | 55+ age-restricted | Built 2004 - 2006 | 100 homes
No reviews yet Albert Courts
$100Ks - $200Ks
Albert Courts, Thurmont, MD
Resale Only | 55+ age-restricted | Built 1991 - 2001 | 100 homes
No reviews yet Boxwood Villas
$500Ks - $600Ks
Boxwood Villas, Urbana, MD
Resale Only | 55+ age-restricted | Built 2019 - 2021 | 92 homes
No reviews yet The Village at Foxfield
$300Ks - $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 - $400Ks
Four Seasons at Ashburn V..., Ashburn, VA
Resale Only | 55+ age-restricted | Built 2005 - 2005 | 80 homes
No reviews yet The Villages at Broadland...
$400Ks - $400Ks
The Villages at Broadland..., Ashburn, VA
New and Resale | 55+ age-restricted | Built 2013 - present | 78 homes
No reviews yet Cadence at Lansdowne
$700Ks - $700Ks
Cadence at Lansdowne, Lansdowne, VA
Resale Only | 55+ age-restricted | Built 2020 - 2024 | 74 homes
No reviews yet The Village at Freedom Hi...
$300Ks - $300Ks
The Village at Freedom Hi..., Hagerstown, MD
New and Resale | 55+ age-restricted | Built 2007 - present | 66 homes
No reviews yet CobbleStone Estates
$400Ks - $500Ks
CobbleStone Estates, Hagerstown, MD
New and Resale | 55+ age-restricted | Built 2015 - present | 66 homes
1...2
Lexington Square 44486 LOWESTOFT SQ, ASHBURN, VA, 20147, Ashburn, VA 20147
$827,046

3 beds

|

3 baths

|

3,128 sq ft

44486 LOWESTOFT SQ, ASHBURN, VA, 20147
Community: Lexington Square
Birchwood at Brambleton 42788 MACBETH TER, ASHBURN, VA, 20148, Ashburn, VA 20148
$849,990

3 beds

|

3 baths

|

2,669 sq ft

42788 MACBETH TER, ASHBURN, VA, 20148
Lansdowne Woods of Virginia 19355 CYPRESS RIDGE TER 903, LEESBURG, V..., Leesburg, VA 20176
$449,000

2 beds

|

2 baths

|

1,251 sq ft

|

Condo

19355 CYPRESS RIDGE TER 903, LEESBURG, V...
Potomac Green 20580 HOPE SPRING TER UNIT 406, ASHBURN,..., Ashburn, VA 20147
$495,000

2 beds

|

2 baths

|

1,586 sq ft

|

Condo

20580 HOPE SPRING TER UNIT 406, ASHBURN,...
Community: Potomac Green
Woodbrook Village 101 ROSEWOOD LN, WINCHESTER, VA, 22602, Winchester, VA 22602
$390,000

2 beds

|

2 baths

|

1,692 sq ft

101 ROSEWOOD LN, WINCHESTER, VA, 22602
Community: Woodbrook Village
Want to learn more about 55+ communities in Winchester Area? 55places can help!
Questions? Call us: (540) 452-4199
Trilogy® at Lake Frederick 116 GROSBEAK CT, LAKE FREDERICK, VA, 226..., Lake Frederick, VA 22630
$574,000

2 beds

|

2 baths

|

2,047 sq ft

116 GROSBEAK CT, LAKE FREDERICK, VA, 226...
Four Seasons at Vint Hill 3680 OSBORNE DR, WARRENTON, VA, 20187, Warrenton, VA 20187
$650,000

4 beds

|

3 baths

|

3,562 sq ft

3680 OSBORNE DR, WARRENTON, VA, 20187
Regency at Dominion Valley 15201 ROYAL CREST DR APT 303, HAYMARKET,..., Haymarket, VA 20169
$445,000

2 beds

|

2 baths

|

1,499 sq ft

|

Condo

15201 ROYAL CREST DR APT 303, HAYMARKET,...
Liberty Grove 8600 LIBERTY TRL 206, MANASSAS, VA, 2011..., Manassas, VA 20110
$357,770

2 beds

|

3 baths

|

1,743 sq ft

|

Condo

8600 LIBERTY TRL 206, MANASSAS, VA, 2011...
Community: Liberty Grove
Birchwood at Brambleton 23640 BOLTON CRESCENT TER # 13-304, ASHB..., Ashburn, VA 20148
$549,990

2 beds

|

2 baths

|

1,419 sq ft

|

Condo

23640 BOLTON CRESCENT TER # 13-304, ASHB...
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.
Potomac Green 44516 BLUERIDGE MEADOWS DR, ASHBURN, VA,..., Ashburn, VA 20147
$920,000

3 beds

|

3 baths

|

2,703 sq ft

44516 BLUERIDGE MEADOWS DR, ASHBURN, VA,...
Community: Potomac Green
The Village at Harvest Ridge 143 HARVEST RIDGE DR, WINCHESTER, VA, 22..., Winchester, VA 22601
$575,000

3 beds

|

2 baths

|

2,233 sq ft

143 HARVEST RIDGE DR, WINCHESTER, VA, 22...
Birchwood at Brambleton 42785 CUMULUS TER, ASHBURN, VA, 20148, Ashburn, VA 20148
$799,900

3 beds

|

3 baths

|

2,669 sq ft

42785 CUMULUS TER, ASHBURN, VA, 20148
Four Seasons at Ashburn Village 44485 CHAMBERLAIN TER UNIT 205, ASHBURN,..., Ashburn, VA 20147
$435,000

2 beds

|

2 baths

|

1,612 sq ft

|

Condo

44485 CHAMBERLAIN TER UNIT 205, ASHBURN,...
Montebello 21729 HAWKSBILL HIGH CIR, STERLING, VA, ..., Sterling, VA 20164
$950,000

2 beds

|

3 baths

|

2,302 sq ft

21729 HAWKSBILL HIGH CIR, STERLING, VA, ...
Community: Montebello
Want to learn more about 55+ communities in Winchester Area? 55places can help!
Questions? Call us: (540) 452-4199
Potomac Green 20610 HOPE SPRING TER 205, ASHBURN, VA, ..., Ashburn, VA 20147
$525,000

2 beds

|

2 baths

|

1,632 sq ft

|

Condo

20610 HOPE SPRING TER 205, ASHBURN, VA, ...
Community: Potomac Green
Heritage Hunt 6769 ARTHUR HILLS DR, GAINESVILLE, VA, 2..., Gainesville, VA 20155
$849,900

4 beds

|

4 baths

|

5,410 sq ft

6769 ARTHUR HILLS DR, GAINESVILLE, VA, 2...
Community: Heritage Hunt
Trilogy® at Lake Frederick 102 PHACELIA WAY, LAKE FREDERICK, VA, 22..., Lake Frederick, VA 22630
$410,000

3 beds

|

4 baths

|

2,200 sq ft

102 PHACELIA WAY, LAKE FREDERICK, VA, 22...
Lexington Square 44494 COALPORT TER, ASHBURN, VA, 20147, Ashburn, VA 20147
$976,316

4 beds

|

4 baths

|

4,109 sq ft

44494 COALPORT TER, ASHBURN, VA, 20147
Community: Lexington Square
Lexington 7 44494 COALPORT TER, ASHBURN, VA, 20147, Ashburn, VA 20147
$976,316

4 beds

|

4 baths

|

4,109 sq ft

44494 COALPORT TER, ASHBURN, VA, 20147
Community: Lexington 7
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.
Cedar Meadows 124 BLUETS DR, WHITE POST, VA, 22663, White Post, VA 22663
$415,000

2 beds

|

2 baths

|

1,509 sq ft

124 BLUETS DR, WHITE POST, VA, 22663
Community: Cedar Meadows
Cedar Meadows 109 BLEEDING HEART DR, WHITE POST, VA, 2..., White Post, VA 22663
$450,000

3 beds

|

2 baths

|

1,765 sq ft

109 BLEEDING HEART DR, WHITE POST, VA, 2...
Community: Cedar Meadows
Abrams Chase 112 AMBERFIELD CT, WINCHESTER, VA, 22602, Winchester, VA 22602
$479,500

2 beds

|

2 baths

|

1,609 sq ft

112 AMBERFIELD CT, WINCHESTER, VA, 22602
Community: Abrams Chase
Regency at Dominion Valley 15209 BRIER CREEK DR, HAYMARKET, VA, 201..., Haymarket, VA 20169
$730,000

2 beds

|

3 baths

|

2,842 sq ft

15209 BRIER CREEK DR, HAYMARKET, VA, 201...
Cedar Meadows 107 BLUETS DR, WHITE POST, VA, 22663, White Post, VA 22663
$450,000

3 beds

|

2 baths

|

1,609 sq ft

107 BLUETS DR, WHITE POST, VA, 22663
Community: Cedar Meadows
Want to learn more about 55+ communities in Winchester Area? 55places can help!
Questions? Call us: (540) 452-4199
Willow Lawn Cottages 1826 KERSHAW LN, WINCHESTER, VA, 22601, Winchester, VA 22601
$387,900

2 beds

|

2 baths

|

1,431 sq ft

1826 KERSHAW LN, WINCHESTER, VA, 22601
Lansdowne Woods of Virginia 19385 CYPRESS RIDGE TER 503, LEESBURG, V..., Leesburg, VA 20176
$435,000

2 beds

|

2 baths

|

1,509 sq ft

|

Condo

19385 CYPRESS RIDGE TER 503, LEESBURG, V...
Birchwood at Brambleton 42743 CUMULUS TER, ASHBURN, VA, 20148, Ashburn, VA 20148
$875,000

3 beds

|

3 baths

|

2,832 sq ft

42743 CUMULUS TER, ASHBURN, VA, 20148
Birchwood at Brambleton 23631 HAVELOCK WALK TER 220, ASHBURN, VA..., Ashburn, VA 20148
$550,000

3 beds

|

2 baths

|

1,971 sq ft

|

Condo

23631 HAVELOCK WALK TER 220, ASHBURN, VA...
Birchwood at Brambleton 23675 HARDESTY TER, ASHBURN, VA, 20148, Ashburn, VA 20148
$859,315

2 beds

|

4 baths

|

2,742 sq ft

23675 HARDESTY 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.
Lansdowne Woods of Virginia 19355 CYPRESS RIDGE TER 203, LEESBURG, V..., Leesburg, VA 20176
$399,000

2 beds

|

2 baths

|

1,251 sq ft

|

Condo

19355 CYPRESS RIDGE TER 203, LEESBURG, V...
Cadence at Lansdowne 18989 CORAL REEF SQ, LEESBURG, VA, 20176, Leesburg, VA 20176
$755,000

3 beds

|

3 baths

|

2,649 sq ft

18989 CORAL REEF SQ, LEESBURG, VA, 20176
Central Parke at Lowes Island 20804 NOBLE TER 208, STERLING, VA, 20165, Sterling, VA 20165
$455,000

2 beds

|

2 baths

|

1,692 sq ft

|

Condo

20804 NOBLE TER 208, STERLING, VA, 20165
Trilogy® at Lake Frederick 111 WAKE ROBIN CT, LAKE FREDERICK, VA, 2..., Lake Frederick, VA 22630
$450,000

4 beds

|

4 baths

|

2,248 sq ft

111 WAKE ROBIN CT, LAKE FREDERICK, VA, 2...
Crestwood Village 7054 BASSWOOD RD, FREDERICK, MD, 21703, Frederick, MD 21703
$199,000
|

1 baths

|

609 sq ft

7054 BASSWOOD RD, 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 3218 THORNAPPLE DR, FREDERICK, MD, 21704, Frederick, MD 21704
$925,000

2 beds

|

3 baths

|

3,058 sq ft

3218 THORNAPPLE DR, FREDERICK, MD, 21704
Emerald Pointe 19446 SAPPHIRE DR, HAGERSTOWN, MD, 21742, Hagerstown, MD 21742
$375,000

2 beds

|

2 baths

|

1,834 sq ft

19446 SAPPHIRE DR, HAGERSTOWN, MD, 21742
Community: Emerald Pointe
Crestwood Village 6908 CHOKEBERRY CT, FREDERICK, MD, 21703, Frederick, MD 21703
$335,000

2 beds

|

1 baths

|

1,300 sq ft

6908 CHOKEBERRY CT, FREDERICK, MD, 21703
Community: Crestwood Village
Albert Courts 117 EASY ST, THURMONT, MD, 21788, Thurmont, MD 21788
$304,500

2 beds

|

2 baths

|

Condo

117 EASY ST, THURMONT, MD, 21788
Community: Albert Courts
Crestwood Village 5671 CRABAPPLE DR, FREDERICK, MD, 21703, Frederick, MD 21703
$349,900

2 beds

|

2 baths

|

1,148 sq ft

5671 CRABAPPLE DR, FREDERICK, MD, 21703
Community: Crestwood Village



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129 homes near Winchester Area
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