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

81 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
No reviews yet Cross Creek Village
$300Ks - $300Ks
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
No reviews yet Woodbrook Village
$300Ks - $300Ks
Woodbrook Village, Winchester, VA
Resale Only | 55+ age-restricted | Built 1999 - 2001 | 81 homes
No reviews yet Cottage Glen
$400Ks - $400Ks
Cottage Glen, Winchester, VA
New and Resale | Age-targeted | Built 2018 - present | 25 homes
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No reviews yet Abrams Chase
$500Ks - $500Ks
Abrams Chase, Winchester, VA
New Construction | 55+ age-restricted | Built 2020 - present | 13 homes
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
$500Ks - $1Ms
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
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.
2.8 rating (6 reviews) Celebrate
$300Ks - $600Ks
Celebrate, Fredericksburg, VA
New and Resale | 55+ age-restricted | Built 2008 - present | 1,100 homes
No reviews yet Penn National
$300Ks - $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 - $900Ks
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 - $400Ks
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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Questions? Call us: (540) 773-2470
4.4 rating (5 reviews) Virginia Heritage at Lee'...
$500Ks - $700Ks
Virginia Heritage at Lee'..., Fredericksburg, VA
Resale Only | 55+ age-restricted | Built 2005 - 2021 | 795 homes
4.3 rating (3 reviews) Falls Run
$300Ks - $500Ks
Falls Run, Fredericksburg, VA
Resale Only | 55+ age-restricted | Built 2002 - 2005 | 781 homes
No reviews yet The Woodlands of Urbana
$400Ks - $800Ks
The Woodlands of Urbana, Urbana, MD
New Construction | 55+ age-restricted | Built 2019 - present | 565 homes
5 rating (1 reviews) Crestwood Village
$300Ks - $400Ks
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
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.
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
No reviews yet Twin Lake Villas
$300Ks - $400Ks
Twin Lake Villas, Locust Grove, VA
New Construction | 55+ age-restricted | Built 2021 - present | 340 homes
No reviews yet Spring Hill
$500Ks - $500Ks
Spring Hill, Lorton, VA
Resale Only | 55+ age-restricted | Built 2006 - 2014 | 282 homes
No reviews yet Regency at Ashburn
$500Ks - $700Ks
Regency at Ashburn, Ashburn, VA
Resale Only | 55+ age-restricted | Built 2013 - 2020 | 268 homes
Want to learn more about 55+ communities in Winchester? 55places can help!
Questions? Call us: (540) 773-2470
No reviews yet ThreeOaksâ„¢
$400Ks - $600Ks
ThreeOaksâ„¢, Culpeper, VA
New Construction | 55+ age-restricted | Built 2024 - present | 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 River Ridge
$600Ks - $600Ks
River Ridge, Woodbridge, VA
Resale Only | 55+ age-restricted | Built 1998 - 2002 | 238 homes
No reviews yet Signature Club at Greenvi...
$500Ks - $600Ks
Signature Club at Greenvi..., New Market, MD
Resale Only | 55+ age-restricted | Built 2003 - 2013 | 233 homes
No reviews yet Regency at Chancellorsvil...
$500Ks - $500Ks
Regency at Chancellorsvil..., Fredericksburg, VA
Resale Only | 55+ age-restricted | Built 2004 - 2019 | 225 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 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 The Atrium at MetroWest
$700Ks - $700Ks
The Atrium at MetroWest, Fairfax, VA
New Construction | 55+ age-restricted | Built 2018 - present | 206 homes
No reviews yet Four Seasons at Virginia ...
$400Ks - $600Ks
Four Seasons at Virginia ..., Woodbridge, VA
New Construction | 55+ age-restricted | Built 2021 - present | 185 homes
No reviews yet Central Parke at Lowes Is...
$400Ks - $400Ks
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? 55places can help!
Questions? Call us: (540) 773-2470
No reviews yet Summerlake
$300Ks - $300Ks
Summerlake, Fredericksburg, VA
Resale Only | 55+ age-restricted | Built 1987 - 1997 | 161 homes
No reviews yet Belmont Bay
$300Ks - $800Ks
Belmont Bay, Woodbridge, VA
New and Resale | Age-targeted | Built 2007 - present | 155 homes
No reviews yet Regency at Belmont
$1Ms - $1Ms
Regency at Belmont, Ashburn, VA
New Construction | 55+ age-restricted | Built 2021 - present | 145 homes
No reviews yet Four Seasons at Charlotte...
$500Ks - $500Ks
Four Seasons at Charlotte..., Ruckersville, VA
New and Resale | 55+ age-restricted | Built 2005 - present | 144 homes
No reviews yet Spring Valley Estates
$300Ks - $300Ks
Spring Valley Estates, Waynesboro, PA
New Construction | 55+ age-restricted | Built 2019 - present | 140 homes
Signature Club at Greenview 10576 EDWARDIAN LN 132, NEW MARKET, MD, ..., New Market, MD 21774
$615,000

3 beds

|

4 baths

|

2,549 sq ft

|

Condo

10576 EDWARDIAN LN 132, NEW MARKET, MD, ...
The Woodlands of Urbana 2916 HERB GARDEN DR, FREDERICK, MD, 2170..., Frederick, MD 21704
$675,000

3 beds

|

3 baths

|

2,508 sq ft

2916 HERB GARDEN DR, FREDERICK, MD, 2170...
Gatherings at Cabin Branch 13210 PETREL ST UNIT 3304, CLARKSBURG, M..., Clarksburg, MD 20871
$479,990

2 beds

|

2 baths

|

1,529 sq ft

|

Condo

13210 PETREL ST UNIT 3304, CLARKSBURG, M...
The Village at Cabin Branch 13210 PETREL ST UNIT 3304, CLARKSBURG, M..., Clarksburg, MD 20871
$479,990

2 beds

|

2 baths

|

1,529 sq ft

|

Condo

13210 PETREL ST UNIT 3304, CLARKSBURG, M...
Gatherings at Cabin Branch 13240 PETREL ST # 106, CLARKSBURG, MD, 2..., Clarksburg, MD 20871
$399,990

1 beds

|

1 baths

|

1,203 sq ft

|

Condo

13240 PETREL ST # 106, CLARKSBURG, MD, 2...
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Questions? Call us: (540) 773-2470
The Village at Cabin Branch 13240 PETREL ST # 106, CLARKSBURG, MD, 2..., Clarksburg, MD 20871
$399,990

1 beds

|

1 baths

|

1,203 sq ft

|

Condo

13240 PETREL ST # 106, CLARKSBURG, MD, 2...
The Village at Cabin Branch 13210 PETREL ST UNIT 3305, CLARKSBURG, M..., Clarksburg, MD 20871
$489,990

2 beds

|

2 baths

|

1,529 sq ft

|

Condo

13210 PETREL ST UNIT 3305, CLARKSBURG, M...
The Village at Cabin Branch 13230 PETREL ST # 2207, CLARKSBURG, MD, ..., Clarksburg, MD 20871
$639,990

3 beds

|

2 baths

|

2,031 sq ft

|

Condo

13230 PETREL ST # 2207, CLARKSBURG, MD, ...
Gatherings at Cabin Branch 13230 PETREL ST # 2207, CLARKSBURG, MD, ..., Clarksburg, MD 20871
$639,990

3 beds

|

2 baths

|

2,031 sq ft

|

Condo

13230 PETREL ST # 2207, CLARKSBURG, MD, ...
Gatherings at Cabin Branch 13210 PETREL ST UNIT 3305, CLARKSBURG, M..., Clarksburg, MD 20871
$489,990

2 beds

|

2 baths

|

1,529 sq ft

|

Condo

13210 PETREL ST UNIT 3305, CLARKSBURG, M...
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.
CobbleStone Estates 9616 COBBLE STONE CT, HAGERSTOWN, MD, 21..., Hagerstown, MD 21740
$450,000

2 beds

|

2 baths

|

1,561 sq ft

9616 COBBLE STONE CT, HAGERSTOWN, MD, 21...
Community: CobbleStone Estates
The Woodlands of Urbana 3315 FIREFLY LN UNIT 203, FREDERICK, MD,..., Frederick, MD 21704
$450,000

2 beds

|

2 baths

|

1,456 sq ft

|

Condo

3315 FIREFLY LN UNIT 203, FREDERICK, MD,...
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
JerMae Estates 31 TOCATI ST, THURMONT, MD, 21788, Thurmont, MD 21788
$540,000

4 beds

|

3 baths

|

2,402 sq ft

31 TOCATI ST, THURMONT, MD, 21788
Community: JerMae Estates
Emerald Pointe 13342 MARQUISE DR, HAGERSTOWN, MD, 21742, Hagerstown, MD 21742
$399,900

2 beds

|

2 baths

|

1,865 sq ft

13342 MARQUISE DR, HAGERSTOWN, MD, 21742
Community: Emerald Pointe
Want to learn more about 55+ communities in Winchester? 55places can help!
Questions? Call us: (540) 773-2470
Ballenger Run 5303 CRAPE MYRTLE DR, FREDERICK, MD, 217..., Frederick, MD 21703
$525,000

3 beds

|

3 baths

|

2,536 sq ft

5303 CRAPE MYRTLE DR, FREDERICK, MD, 217...
Community: Ballenger Run
Signature Club at Greenview 5808 HOLLYS WAY # 71, NEW MARKET, MD, 21..., New Market, MD 21774
$599,900

3 beds

|

3 baths

|

2,413 sq ft

5808 HOLLYS WAY # 71, NEW MARKET, MD, 21...
The Woodlands of Urbana 2954 CARAWAY DR, FREDERICK, MD, 21704, Frederick, MD 21704
$835,000

2 beds

|

3 baths

|

2,952 sq ft

2954 CARAWAY DR, FREDERICK, MD, 21704
Emerald Pointe 19409 MOONSTONE DR, HAGERSTOWN, MD, 2174..., Hagerstown, MD 21742
$499,900

2 beds

|

3 baths

|

2,673 sq ft

19409 MOONSTONE DR, HAGERSTOWN, MD, 2174...
Community: Emerald Pointe
The Woodlands of Urbana 3050 IVY MEADOW DR, FREDERICK, MD, 21704, Frederick, MD 21704
$925,000

2 beds

|

3 baths

|

2,826 sq ft

3050 IVY MEADOW DR, FREDERICK, MD, 21704
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.
Emerald Pointe 19443 SAPPHIRE DR, HAGERSTOWN, MD, 21742, Hagerstown, MD 21742
$399,000

2 beds

|

2 baths

|

1,566 sq ft

19443 SAPPHIRE DR, HAGERSTOWN, MD, 21742
Community: Emerald Pointe
Courts of Clarksburg 21822 BONESET WAY, GERMANTOWN, MD, 20876, Germantown, MD 20876
$649,999

2 beds

|

2 baths

|

1,540 sq ft

21822 BONESET WAY, GERMANTOWN, MD, 20876
Crestwood Village 5734 BOX ELDER CT, FREDERICK, MD, 21703, Frederick, MD 21703
$365,000

2 beds

|

2 baths

|

1,264 sq ft

5734 BOX ELDER CT, FREDERICK, MD, 21703
Community: Crestwood Village
Emerald Pointe 13430 MARQUISE DR # 80, HAGERSTOWN, MD, ..., Hagerstown, MD 21742
$499,900

2 beds

|

3 baths

|

2,739 sq ft

13430 MARQUISE DR # 80, HAGERSTOWN, MD, ...
Community: Emerald Pointe
Emerald Pointe 13348 DIAMOND POINTE DR # V228, HAGERSTO..., Hagerstown, MD 21742
$484,900

2 beds

|

2 baths

|

1,850 sq ft

13348 DIAMOND POINTE DR # V228, HAGERSTO...
Community: Emerald Pointe
Want to learn more about 55+ communities in Winchester? 55places can help!
Questions? Call us: (540) 773-2470
CobbleStone Estates 18210 WISTERIA WAY, HAGERSTOWN, MD, 2174..., Hagerstown, MD 21740
$415,000

3 beds

|

3 baths

|

2,098 sq ft

18210 WISTERIA WAY, HAGERSTOWN, MD, 2174...
Community: CobbleStone Estates
Emerald Pointe 19446 SAPPHIRE DR, HAGERSTOWN, MD, 21742, Hagerstown, MD 21742
$395,000

2 beds

|

2 baths

|

2,574 sq ft

19446 SAPPHIRE DR, HAGERSTOWN, MD, 21742
Community: Emerald Pointe
Gatherings at Potomac Station 750 MOUNT AIRY TER NE UNIT 104, LEESBURG..., Leesburg, VA 20176
$518,776

2 beds

|

2 baths

|

1,532 sq ft

|

Condo

750 MOUNT AIRY TER NE UNIT 104, LEESBURG...
Gatherings at Potomac Station 700 MOUNT AIRY TER NE UNIT 403, LEESBURG..., Leesburg, VA 20176
$494,999

2 beds

|

2 baths

|

1,410 sq ft

|

Condo

700 MOUNT AIRY TER NE UNIT 403, LEESBURG...
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.
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
Gatherings at Potomac Station 750 MOUNT AIRY TER NE UNIT 206, LEESBURG..., Leesburg, VA 20176
$474,999

2 beds

|

2 baths

|

1,532 sq ft

|

Condo

750 MOUNT AIRY TER NE UNIT 206, LEESBURG...
Montebello 46410 BLACKROCK SUMMIT TER, STERLING, VA..., Sterling, VA 20164
$850,000

3 beds

|

3 baths

|

2,521 sq ft

46410 BLACKROCK SUMMIT TER, STERLING, VA...
Community: Montebello
Cascades at Embrey Mill 157 SMOKEBUSH DR, STAFFORD, VA, 22554, Stafford, VA 22554
$554,999

3 beds

|

3 baths

|

2,296 sq ft

157 SMOKEBUSH DR, STAFFORD, VA, 22554
Lansdowne Woods of Virginia 19365 CYPRESS RIDGE TER UNIT 401, LEESBU..., Leesburg, VA 20176
$479,000

3 beds

|

2 baths

|

1,534 sq ft

|

Condo

19365 CYPRESS RIDGE TER UNIT 401, LEESBU...
Want to learn more about 55+ communities in Winchester? 55places can help!
Questions? Call us: (540) 773-2470
Lexington 7 44490 COALPORT TER, ASHBURN, VA, 20147, Ashburn, VA 20147
$954,990

4 beds

|

4 baths

|

4,109 sq ft

44490 COALPORT TER, ASHBURN, VA, 20147
Community: Lexington 7
Celebrate 117 HYANNIS PL, FREDERICKSBURG, VA, 2240..., Fredericksburg, VA 22406
$414,990

2 beds

|

2 baths

|

1,505 sq ft

117 HYANNIS PL, FREDERICKSBURG, VA, 2240...
Community: Celebrate
Country Manor 46 LANTERN LN, SHIPPENSBURG, PA, 17257, Shippensburg, PA 17257
$199,000

3 beds

|

2 baths

|

1,778 sq ft

46 LANTERN LN, SHIPPENSBURG, PA, 17257
Community: Country Manor
New Country Manor 38 COLONIAL CT, SHIPPENSBURG, PA, 17257, Shippensburg, PA 17257
$96,900

3 beds

|

2 baths

|

1,152 sq ft

38 COLONIAL CT, SHIPPENSBURG, PA, 17257
Community: Country Manor
Penn National 4581 RANGE RUNNER DR, FAYETTEVILLE, PA, ..., Fayetteville, PA 17222
$385,000

2 beds

|

2 baths

|

1,408 sq ft

4581 RANGE RUNNER DR, FAYETTEVILLE, PA, ...
Community: Penn National

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81 communities near Winchester
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