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

82 communities near Winchester

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5 rating (1 reviews) Willow Lawn Cottages
$300Ks - $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
Woodbrook Village
$300Ks - $300Ks
Woodbrook Village, Winchester, VA
Resale Only | 55+ age-restricted | Built 1999 - 2001 | 81 homes
Cottage Glen
$400Ks - $400Ks
Cottage Glen, Winchester, VA
New and Resale | Age-targeted | Built 2018 - present | 25 homes
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Abrams Chase
$500Ks - $500Ks
Abrams Chase, Winchester, VA
New Construction | 55+ age-restricted | Built 2020 - present | 13 homes
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
$600Ks - $900Ks
Potomac Green, Ashburn, VA
Resale Only | 55+ age-restricted | Built 2005 - 2016 | 1,400 homes
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
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.
3.1 rating (7 reviews) Celebrate
$300Ks - $600Ks
Celebrate, Fredericksburg, VA
New and Resale | 55+ age-restricted | Built 2008 - present | 1,100 homes
Penn National
$200Ks - $800Ks
Penn National, Fayetteville, PA
New and Resale | Age-targeted | Built 1968 - present | 1,100 homes
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
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
5 rating (1 reviews) Four Seasons at Historic ...
$600Ks - $700Ks
Four Seasons at Historic ..., Dumfries, VA
Resale Only | 55+ age-restricted | Built 2002 - 2010 | 801 homes
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4.4 rating (5 reviews) Virginia Heritage at Lee'...
$500Ks - $600Ks
Virginia Heritage at Lee'..., Fredericksburg, VA
Resale Only | 55+ age-restricted | Built 2005 - 2021 | 795 homes
4.3 rating (3 reviews) Falls Run
$300Ks - $400Ks
Falls Run, Fredericksburg, VA
Resale Only | 55+ age-restricted | Built 2002 - 2005 | 781 homes
The Woodlands of Urbana
$600Ks - $600Ks
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
Carter's Mill
$400Ks - $700Ks
Carter's Mill, Haymarket, VA
New Construction | 55+ age-restricted | Built 2020 - present | 480 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.
3 rating (2 reviews) Dunbarton
$600Ks - $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
Twin Lake Villas
$300Ks - $400Ks
Twin Lake Villas, Locust Grove, VA
New Construction | 55+ age-restricted | Built 2021 - present | 340 homes
Spring Hill
$500Ks - $800Ks
Spring Hill, Lorton, VA
Resale Only | 55+ age-restricted | Built 2006 - 2014 | 282 homes
Four Seasons at Charlotte...
$400Ks - $500Ks
Four Seasons at Charlotte..., Ruckersville, VA
Resale Only | 55+ age-restricted | Built 2005 - present | 275 homes
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Questions? Call us: (540) 773-2470
Regency at Ashburn
$500Ks - $600Ks
Regency at Ashburn, Ashburn, VA
Resale Only | 55+ age-restricted | Built 2013 - 2020 | 268 homes
ThreeOaksâ„¢
$400Ks - $800Ks
ThreeOaksâ„¢, Culpeper, VA
New Construction | 55+ age-restricted | Built 2024 - present | 268 homes
Emerald Pointe
$300Ks - $400Ks
Emerald Pointe, Hagerstown, MD
New and Resale | 55+ age-restricted | Built 2008 - present | 250 homes
River Ridge
$500Ks - $700Ks
River Ridge, Woodbridge, VA
Resale Only | 55+ age-restricted | Built 1998 - 2002 | 238 homes
Signature Club at Greenvi...
$400Ks - $900Ks
Signature Club at Greenvi..., New Market, MD
Resale Only | 55+ age-restricted | Built 2003 - 2013 | 233 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 Chancellorsvil...
$400Ks - $400Ks
Regency at Chancellorsvil..., Fredericksburg, VA
Resale Only | 55+ age-restricted | Built 2004 - 2019 | 225 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 - $900Ks
Regency at Creekside, Gainesville, VA
Resale Only | 55+ age-restricted | Built 2016 - 2020 | 208 homes
The Atrium at MetroWest
$700Ks - $700Ks
The Atrium at MetroWest, Fairfax, VA
New Construction | 55+ age-restricted | Built 2018 - present | 206 homes
Four Seasons at Virginia ...
$400Ks - $600Ks
Four Seasons at Virginia ..., Woodbridge, VA
New Construction | 55+ age-restricted | Built 2021 - present | 185 homes
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Questions? Call us: (540) 773-2470
Central Parke at Lowes Is...
$400Ks - $700Ks
Central Parke at Lowes Is..., Sterling, VA
Resale Only | 55+ age-restricted | Built 2003 - 2005 | 181 homes
Summerlake
$300Ks - $300Ks
Summerlake, Fredericksburg, VA
Resale Only | 55+ age-restricted | Built 1987 - 1997 | 161 homes
Belmont Bay
$300Ks - $800Ks
Belmont Bay, Woodbridge, VA
New and Resale | Age-targeted | Built 2007 - present | 155 homes
Regency at Belmont
$900Ks - $900Ks
Regency at Belmont, Ashburn, VA
New Construction | 55+ age-restricted | Built 2021 - present | 145 homes
Courts of Clarksburg
$600Ks - $700Ks
Courts of Clarksburg, Clarksburg, MD
Resale Only | 55+ age-restricted | Built 2016 - 2020 | 140 homes
Signature Club at Greenview 5948 JACOBEAN PL, NEW MARKET, MD, 21774, New Market, MD 21774
$660,000

3 beds

|

3 baths

|

3,123 sq ft

|

Condo

5948 JACOBEAN PL, NEW MARKET, MD, 21774
Saintsbury Plaza 2905 SAINTSBURY PLZ 315, FAIRFAX, VA, 22..., Fairfax, VA 22031
$419,900

2 beds

|

2 baths

|

1,264 sq ft

|

Condo

2905 SAINTSBURY PLZ 315, FAIRFAX, VA, 22...
Community: Saintsbury Plaza
Four Seasons at Historic Virginia 3758 BLOWING LEAF PL, DUMFRIES, VA, 2202..., Dumfries, VA 22025
$659,999

5 beds

|

3 baths

|

3,465 sq ft

3758 BLOWING LEAF PL, DUMFRIES, VA, 2202...
New Lansdowne Woods of Virginia 19360 MAGNOLIA GROVE SQ UNIT 316, LEESBU..., Leesburg, VA 20176
$575,000

2 beds

|

2 baths

|

1,642 sq ft

|

Condo

19360 MAGNOLIA GROVE SQ UNIT 316, LEESBU...
Celebrate 91 DENISON ST, FREDERICKSBURG, VA, 22406, Fredericksburg, VA 22406
$528,000

3 beds

|

3 baths

|

2,588 sq ft

91 DENISON ST, FREDERICKSBURG, VA, 22406
Community: Celebrate
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Questions? Call us: (540) 773-2470
New Woodbrook Village 105 TANGLEWOOD LN, WINCHESTER, VA, 22602, Winchester, VA 22602
$375,000

2 beds

|

2 baths

|

1,372 sq ft

105 TANGLEWOOD LN, WINCHESTER, VA, 22602
Community: Woodbrook Village
Heritage Hunt 13753 TUSCARORA CT, GAINESVILLE, VA, 201..., Gainesville, VA 20155
$750,000

3 beds

|

3 baths

|

3,338 sq ft

13753 TUSCARORA CT, GAINESVILLE, VA, 201...
Community: Heritage Hunt
Falls Run 18 CHANTILLY PL, FREDERICKSBURG, VA, 224..., Fredericksburg, VA 22406
$425,000

3 beds

|

3 baths

|

2,560 sq ft

18 CHANTILLY PL, FREDERICKSBURG, VA, 224...
Community: Falls Run
Regency at Dominion Valley 5124 FALDO DR, HAYMARKET, VA, 20169, Haymarket, VA 20169
$750,000

2 beds

|

3 baths

|

3,249 sq ft

5124 FALDO DR, HAYMARKET, VA, 20169
Potomac Green 20763 CRESCENT POINTE PL, ASHBURN, VA, 2..., Ashburn, VA 20147
$865,000

3 beds

|

3 baths

|

2,810 sq ft

20763 CRESCENT POINTE PL, ASHBURN, VA, 2...
Community: Potomac Green
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 Potomac Green 20742 ADAMS MILL PL, ASHBURN, VA, 20147, Ashburn, VA 20147
$800,000

3 beds

|

2 baths

|

1,670 sq ft

20742 ADAMS MILL PL, ASHBURN, VA, 20147
Community: Potomac Green
Four Seasons at Vint Hill 3607 MAUCHLEY CT, WARRENTON, VA, 20187, Warrenton, VA 20187
$624,950

2 beds

|

2 baths

|

2,156 sq ft

3607 MAUCHLEY CT, WARRENTON, VA, 20187
Celebrate 130 LONG POINT DR, FREDERICKSBURG, VA, 2..., Fredericksburg, VA 22406
$489,000

3 beds

|

3 baths

|

3,056 sq ft

130 LONG POINT DR, FREDERICKSBURG, VA, 2...
Community: Celebrate
Celebrate 56 BATTERY POINT DR, FREDERICKSBURG, VA,..., Fredericksburg, VA 22406
$598,000

3 beds

|

3 baths

|

2,864 sq ft

56 BATTERY POINT DR, FREDERICKSBURG, VA,...
Community: Celebrate
New 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...
Want to learn more about 55+ communities in Winchester? 55places can help!
Questions? Call us: (540) 773-2470
Celebrate 187 DENISON ST, FREDERICKSBURG, VA, 2240..., Fredericksburg, VA 22406
$540,000

3 beds

|

3 baths

|

2,177 sq ft

187 DENISON ST, FREDERICKSBURG, VA, 2240...
Community: Celebrate
Regency at Dominion Valley 5320 TREVINO DR, HAYMARKET, VA, 20169, Haymarket, VA 20169
$875,000

4 beds

|

3 baths

|

3,082 sq ft

5320 TREVINO DR, HAYMARKET, VA, 20169
Celebrate 5 MONTAUK AVE, FREDERICKSBURG, VA, 22406, Fredericksburg, VA 22406
$639,900

3 beds

|

3 baths

|

2,586 sq ft

5 MONTAUK AVE, FREDERICKSBURG, VA, 22406
Community: Celebrate
New Four Seasons at Historic Virginia 16529 SPARKLING BROOK LOOP, DUMFRIES, VA..., Dumfries, VA 22025
$610,500

2 beds

|

2 baths

|

2,391 sq ft

16529 SPARKLING BROOK LOOP, DUMFRIES, VA...
New Regency at Dominion Valley 15463 LEGACY WAY, HAYMARKET, VA, 20169, Haymarket, VA 20169
$749,000

3 beds

|

3 baths

|

3,814 sq ft

15463 LEGACY WAY, HAYMARKET, VA, 20169
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 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
New River Ridge 12165 EDDYSTONE CT, WOODBRIDGE, VA, 2219..., Woodbridge, VA 22192
$749,900

4 beds

|

4 baths

|

4,695 sq ft

12165 EDDYSTONE CT, WOODBRIDGE, VA, 2219...
Community: River Ridge
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 13141 TRIPLE CROWN LOOP, GAINESVILLE, VA..., Gainesville, VA 20155
$799,900

2 beds

|

4 baths

|

3,494 sq ft

13141 TRIPLE CROWN LOOP, GAINESVILLE, VA...
Community: Heritage Hunt
New Birchwood at Brambleton 42789 MACBETH TER, ASHBURN, VA, 20148, Ashburn, VA 20148
$895,000

4 beds

|

3 baths

|

3,026 sq ft

42789 MACBETH TER, ASHBURN, VA, 20148
Want to learn more about 55+ communities in Winchester? 55places can help!
Questions? Call us: (540) 773-2470
Cascades at Embrey Mill 241 SMOKEBUSH DR, STAFFORD, VA, 22554, Stafford, VA 22554
$645,000

4 beds

|

4 baths

|

3,291 sq ft

|

Condo

241 SMOKEBUSH DR, STAFFORD, VA, 22554
Gatherings at Wellington 9204 CHARLESTON DR UNIT 404, MANASSAS, V..., Manassas, VA 20110
$379,000

2 beds

|

2 baths

|

1,504 sq ft

|

Condo

9204 CHARLESTON DR UNIT 404, MANASSAS, V...
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
Birchwood at Brambleton 43044 GREELEY SQ, ASHBURN, VA, 20148, Ashburn, VA 20148
$1,050,000

4 beds

|

3 baths

|

3,753 sq ft

43044 GREELEY SQ, ASHBURN, VA, 20148
The Retreat at Poland Hill 43441 BETTYS FARM DR, CHANTILLY, VA, 201..., Chantilly, VA 20152
$949,950

4 beds

|

4 baths

|

3,553 sq ft

43441 BETTYS FARM DR, CHANTILLY, VA, 201...
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 Woodbrook Village 222 CRESTWOOD LN, WINCHESTER, VA, 22602, Winchester, VA 22602
$379,000

2 beds

|

2 baths

|

1,260 sq ft

222 CRESTWOOD LN, WINCHESTER, VA, 22602
Community: Woodbrook Village
New Potomac Green 44529 BLUERIDGE MEADOWS DR, ASHBURN, VA,..., Ashburn, VA 20147
$913,000

4 beds

|

4 baths

|

2,709 sq ft

44529 BLUERIDGE MEADOWS DR, ASHBURN, VA,...
Community: Potomac Green
Twin Lake Villas 35049 MANSOURS DR, LOCUST GROVE, VA, 225..., Locust Grove, VA 22508
$396,000

3 beds

|

2 baths

|

1,369 sq ft

35049 MANSOURS DR, LOCUST GROVE, VA, 225...
Community: Twin Lake Villas
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...
Montebello 46434 ROSE RIVER TER, STERLING, VA, 2016..., Sterling, VA 20164
$799,900

3 beds

|

3 baths

|

2,521 sq ft

46434 ROSE RIVER TER, STERLING, VA, 2016...
Community: Montebello
Want to learn more about 55+ communities in Winchester? 55places can help!
Questions? Call us: (540) 773-2470
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...
Woodbrook Village 221 CRESTWOOD LN, WINCHESTER, VA, 22602, Winchester, VA 22602
$379,000

2 beds

|

2 baths

|

1,384 sq ft

221 CRESTWOOD LN, WINCHESTER, VA, 22602
Community: Woodbrook Village
Birchwood at Brambleton 42788 MACBETH TER, ASHBURN, VA, 20148, Ashburn, VA 20148
$799,000

3 beds

|

3 baths

|

2,669 sq ft

42788 MACBETH TER, ASHBURN, VA, 20148
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...
Celebrate 9 BRANT CT, FREDERICKSBURG, VA, 22406, Fredericksburg, VA 22406
$499,000

3 beds

|

3 baths

|

2,656 sq ft

9 BRANT CT, FREDERICKSBURG, VA, 22406
Community: Celebrate
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82 communities near Winchester
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