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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
$800Ks - $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 - $500Ks
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
$400Ks - $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
$800Ks - $900Ks
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
Spring Valley Estates
$300Ks - $300Ks
Spring Valley Estates, Waynesboro, PA
New Construction | 55+ age-restricted | Built 2019 - present | 140 homes
Country Manor 84 LANTERN LN, SHIPPENSBURG, PA, 17257, Shippensburg, PA 17257
$184,900

2 beds

|

2 baths

|

1,438 sq ft

84 LANTERN LN, SHIPPENSBURG, PA, 17257
Community: Country Manor
New Regency at Dominion Valley 15251 ROYAL CREST DR APT 103, HAYMARKET,..., Haymarket, VA 20169
$470,000

2 beds

|

2 baths

|

1,499 sq ft

|

Condo

15251 ROYAL CREST DR APT 103, HAYMARKET,...
New Four Seasons at Historic Virginia 17401 FOUR SEASONS DR, DUMFRIES, VA, 220..., Dumfries, VA 22025
$625,000

3 beds

|

2 baths

|

2,453 sq ft

17401 FOUR SEASONS DR, DUMFRIES, VA, 220...
New Celebrate 9 MONTERA AVE, FREDERICKSBURG, VA, 22406, Fredericksburg, VA 22406
$633,000

3 beds

|

3 baths

|

2,060 sq ft

9 MONTERA AVE, FREDERICKSBURG, VA, 22406
Community: Celebrate
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
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Questions? Call us: (540) 773-2470
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
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 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,...
River Ridge 12221 SEAFORD CT, WOODBRIDGE, VA, 22192, Woodbridge, VA 22192
$584,900

3 beds

|

3 baths

|

1,962 sq ft

12221 SEAFORD CT, WOODBRIDGE, VA, 22192
Community: River Ridge
New Regency at Dominion Valley 5484 RODRIQUEZ LN, HAYMARKET, VA, 20169, Haymarket, VA 20169
$745,000

3 beds

|

3 baths

|

2,598 sq ft

5484 RODRIQUEZ LN, 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.
New Lansdowne Woods of Virginia 19385 CYPRESS RIDGE TER UNIT 404, LEESBU..., Leesburg, VA 20176
$340,000

2 beds

|

2 baths

|

1,038 sq ft

|

Condo

19385 CYPRESS RIDGE TER UNIT 404, LEESBU...
New The Retreat at Poland Hill 43441 BETTYS FARM DR, CHANTILLY, VA, 201..., Chantilly, VA 20152
$945,000

4 beds

|

4 baths

|

3,553 sq ft

43441 BETTYS FARM DR, CHANTILLY, VA, 201...
Cascades at Embrey Mill 241 SMOKEBUSH DR, STAFFORD, VA, 22554, Stafford, VA 22554
$644,000

4 beds

|

4 baths

|

3,291 sq ft

|

Condo

241 SMOKEBUSH DR, STAFFORD, VA, 22554
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
Regency at Chancellorsville 12524 REGIMENT LN, FREDERICKSBURG, VA, 2..., Fredericksburg, VA 22407
$427,500

2 beds

|

2 baths

|

1,802 sq ft

12524 REGIMENT LN, FREDERICKSBURG, VA, 2...
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...
Celebrate 270 LONG POINT DR, FREDERICKSBURG, VA, 2..., Fredericksburg, VA 22406
$389,900

2 beds

|

2 baths

|

1,386 sq ft

270 LONG POINT DR, FREDERICKSBURG, VA, 2...
Community: Celebrate
Heritage Hunt 13963 CHELMSFORD DR, GAINESVILLE, VA, 20..., Gainesville, VA 20155
$630,000

3 beds

|

3 baths

|

2,090 sq ft

13963 CHELMSFORD DR, GAINESVILLE, VA, 20...
Community: Heritage Hunt
New Lansdowne Woods of Virginia 19375 CYPRESS RIDGE TER 601, LEESBURG, V..., Leesburg, VA 20176
$529,900

3 beds

|

2 baths

|

1,534 sq ft

|

Condo

19375 CYPRESS RIDGE TER 601, LEESBURG, V...
New Regency at Ashburn 20862 SABER JET PL, ASHBURN, VA, 20147, Ashburn, VA 20147
$915,000

3 beds

|

4 baths

|

4,150 sq ft

20862 SABER JET PL, ASHBURN, VA, 20147
Community: Regency at Ashburn
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 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...
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
Summerlake 11471 CHARLESTON CT, FREDERICKSBURG, VA,..., Fredericksburg, VA 22407
$379,900

3 beds

|

3 baths

|

1,969 sq ft

11471 CHARLESTON CT, FREDERICKSBURG, VA,...
Community: Summerlake
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...
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
Want to learn more about 55+ communities in Winchester? 55places can help!
Questions? Call us: (540) 773-2470
New Trilogy® at Lake Frederick 129 TOWHEE DR, LAKE FREDERICK, VA, 22630, Lake Frederick, VA 22630
$675,000

3 beds

|

2 baths

|

2,089 sq ft

129 TOWHEE DR, LAKE FREDERICK, VA, 22630
Legacy Woods 11917 LEGACY WOODS DR, FREDERICKSBURG, V..., Fredericksburg, VA 22407
$589,000

5 beds

|

3 baths

|

3,311 sq ft

11917 LEGACY WOODS DR, FREDERICKSBURG, V...
Community: Legacy Woods
Trilogy® at Lake Frederick 118 VICEROY WAY, LAKE FREDERICK, VA, 226..., Lake Frederick, VA 22630
$650,000

3 beds

|

3 baths

|

2,523 sq ft

118 VICEROY WAY, LAKE FREDERICK, VA, 226...
New 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...
Celebrate 125 DENISON ST, FREDERICKSBURG, VA, 2240..., Fredericksburg, VA 22406
$589,000

3 beds

|

3 baths

|

2,736 sq ft

125 DENISON ST, FREDERICKSBURG, VA, 2240...
Community: Celebrate
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.
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
Spring Hill 8970 FASCINATION CT APT 315, LORTON, VA,..., Lorton, VA 22079
$525,000

2 beds

|

2 baths

|

1,558 sq ft

|

Condo

8970 FASCINATION CT APT 315, LORTON, VA,...
Community: Spring Hill
Celebrate 14 PENSACOLA ST, FREDERICKSBURG, VA, 224..., Fredericksburg, VA 22406
$463,000

2 beds

|

2 baths

|

1,445 sq ft

14 PENSACOLA ST, FREDERICKSBURG, VA, 224...
Community: Celebrate
New Falls Run 15 HARTFORD WAY # 40-1, FREDERICKSBURG, ..., Fredericksburg, VA 22406
$399,000

3 beds

|

3 baths

|

1,657 sq ft

|

Condo

15 HARTFORD WAY # 40-1, FREDERICKSBURG, ...
Community: Falls Run
Trilogy® at Lake Frederick 153 LEATHER FLOWER DR, LAKE FREDERICK, V..., Lake Frederick, VA 22630
$499,900

4 beds

|

4 baths

|

2,719 sq ft

153 LEATHER FLOWER DR, LAKE FREDERICK, V...
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Questions? Call us: (540) 773-2470
Keswick Villas 8824 SELBY CT, SPOTSYLVANIA, VA, 22551, Spotsylvania, VA 22551
$445,325

3 beds

|

4 baths

|

2,145 sq ft

8824 SELBY CT, SPOTSYLVANIA, VA, 22551
Community: Keswick Villas
Keswick Villas 8816 SELBY CT, SPOTSYLVANIA, VA, 22551, Spotsylvania, VA 22551
$425,625

3 beds

|

4 baths

|

2,145 sq ft

8816 SELBY CT, SPOTSYLVANIA, VA, 22551
Community: Keswick Villas
Keswick Villas 7722 HARLOW CIR, SPOTSYLVANIA, VA, 22551, Spotsylvania, VA 22551
$458,800

3 beds

|

4 baths

|

2,189 sq ft

7722 HARLOW CIR, SPOTSYLVANIA, VA, 22551
Community: Keswick Villas
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 130 AMBROSE LN, FREDERICKSBURG, VA, 2240..., Fredericksburg, VA 22406
$425,000

2 beds

|

2 baths

|

1,505 sq ft

130 AMBROSE LN, FREDERICKSBURG, VA, 2240...
Community: Celebrate
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82 communities near Winchester
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