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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
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
Woodbrook Village, Winchester, VA
Resale Only | 55+ age-restricted | Built 1999 - 2001 | 81 homes
Cottage Glen
$400Ks
Cottage Glen, Winchester, VA
New and Resale | Age-targeted | Built 2018 - present | 25 homes
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Abrams Chase
$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
$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
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 - $600Ks
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'...
$400Ks - $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 - $500Ks
Falls Run, Fredericksburg, VA
Resale Only | 55+ age-restricted | Built 2002 - 2005 | 781 homes
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
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
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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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
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
Regency at Creekside, Gainesville, VA
Resale Only | 55+ age-restricted | Built 2016 - 2020 | 208 homes
The Atrium at MetroWest
$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
Summerlake, Fredericksburg, VA
Resale Only | 55+ age-restricted | Built 1987 - 1997 | 161 homes
Belmont Bay
$400Ks - $800Ks
Belmont Bay, Woodbridge, VA
New and Resale | Age-targeted | Built 2007 - present | 155 homes
Regency at Belmont
$900Ks
Regency at Belmont, Ashburn, VA
New Construction | 55+ age-restricted | Built 2021 - present | 145 homes
Spring Valley Estates
$300Ks
Spring Valley Estates, Waynesboro, PA
New Construction | 55+ age-restricted | Built 2019 - present | 140 homes
Cascades at Embrey Mill 241 SMOKEBUSH DR, STAFFORD, VA, 22554, Stafford, VA 22554
$643,000

4 beds

|

4 baths

|

3,291 sq ft

|

Condo

241 SMOKEBUSH DR, STAFFORD, VA, 22554
Heritage Hunt 13746 HERITAGE VALLEY WAY, GAINESVILLE, ..., Gainesville, VA 20155
$729,000

3 beds

|

3 baths

|

2,640 sq ft

13746 HERITAGE VALLEY WAY, GAINESVILLE, ...
Community: Heritage Hunt
Barley Woods 12211 GLEN OAKS DR, FREDERICKSBURG, VA, ..., Fredericksburg, VA 22407
$499,900

2 beds

|

2 baths

|

1,981 sq ft

12211 GLEN OAKS DR, FREDERICKSBURG, VA, ...
Community: Barley Woods
Heritage Hunt 6868 SADDLE RUN WAY, GAINESVILLE, VA, 20..., Gainesville, VA 20155
$675,000

3 beds

|

3 baths

|

2,528 sq ft

6868 SADDLE RUN WAY, GAINESVILLE, VA, 20...
Community: Heritage Hunt
Heritage Hunt 6880 SADDLE RUN WAY, GAINESVILLE, VA, 20..., Gainesville, VA 20155
$749,000

2 beds

|

3 baths

|

3,087 sq ft

6880 SADDLE RUN WAY, GAINESVILLE, VA, 20...
Community: Heritage Hunt
Want to learn more about 55+ communities in Winchester, VA? 55places can help!
Questions? Call us: (540) 773-2470
New Celebrate 20 FENWICK DR, FREDERICKSBURG, VA, 22406, Fredericksburg, VA 22406
$449,900

2 beds

|

2 baths

|

1,445 sq ft

20 FENWICK DR, FREDERICKSBURG, VA, 22406
Community: Celebrate
Gatherings at Wellington 10273 FOUNTAIN CIR 306, MANASSAS, VA, 20..., Manassas, VA 20110
$375,000

2 beds

|

2 baths

|

1,558 sq ft

|

Condo

10273 FOUNTAIN CIR 306, MANASSAS, VA, 20...
Central Parke at Lowes Island 20810 NOBLE TER 205, STERLING, VA, 20165, Sterling, VA 20165
$494,000

3 beds

|

2 baths

|

1,989 sq ft

|

Condo

20810 NOBLE TER 205, STERLING, VA, 20165
Potomac Green 20432 ISLAND WEST SQ, ASHBURN, VA, 20147, Ashburn, VA 20147
$739,999

3 beds

|

3 baths

|

2,253 sq ft

20432 ISLAND WEST SQ, ASHBURN, VA, 20147
Community: Potomac Green
Regency at Dominion Valley 15201 ROYAL CREST DR APT 407, HAYMARKET,..., Haymarket, VA 20169
$440,000

2 beds

|

2 baths

|

1,538 sq ft

|

Condo

15201 ROYAL CREST DR APT 407, HAYMARKET,...
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
$864,900

4 beds

|

3 baths

|

4,486 sq ft

13612 RYTON RIDGE LN, GAINESVILLE, VA, 2...
Community: Heritage Hunt
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
Lexington 7 19873 SILVERY BLUE TER, ASHBURN, VA, 201..., Ashburn, VA 20147
$899,000

4 beds

|

4 baths

|

3,711 sq ft

19873 SILVERY BLUE TER, ASHBURN, VA, 201...
Community: Lexington 7
New Virginia Heritage at Lee's Parke 5910 W CARNIFEX FERRY RD, FREDERICKSBURG..., Fredericksburg, VA 22407
$525,000

3 beds

|

3 baths

|

3,004 sq ft

5910 W CARNIFEX FERRY RD, FREDERICKSBURG...
Summerlake 11471 CHARLESTON CT, FREDERICKSBURG, VA,..., Fredericksburg, VA 22407
$374,000

3 beds

|

3 baths

|

1,969 sq ft

11471 CHARLESTON CT, FREDERICKSBURG, VA,...
Community: Summerlake
Want to learn more about 55+ communities in Winchester, VA? 55places can help!
Questions? Call us: (540) 773-2470
Lansdowne Woods of Virginia 19375 CYPRESS RIDGE TER 207, LEESBURG, V..., Leesburg, VA 20176
$399,900

2 beds

|

2 baths

|

1,380 sq ft

|

Condo

19375 CYPRESS RIDGE TER 207, LEESBURG, V...
Lexington 7 44506 LOWESTOFT SQ, ASHBURN, VA, 20147, Ashburn, VA 20147
$837,656

3 beds

|

3 baths

|

2,969 sq ft

44506 LOWESTOFT SQ, ASHBURN, VA, 20147
Community: Lexington 7
Lexington Square 44506 LOWESTOFT SQ, ASHBURN, VA, 20147, Ashburn, VA 20147
$837,656

3 beds

|

3 baths

|

2,969 sq ft

44506 LOWESTOFT SQ, ASHBURN, VA, 20147
Community: Lexington Square
Lexington 7 44508 LOWESTOFT SQ, ASHBURN, VA, 20147, Ashburn, VA 20147
$818,236

3 beds

|

3 baths

|

3,036 sq ft

44508 LOWESTOFT SQ, ASHBURN, VA, 20147
Community: Lexington 7
Lexington Square 44508 LOWESTOFT SQ, ASHBURN, VA, 20147, Ashburn, VA 20147
$818,236

3 beds

|

3 baths

|

3,036 sq ft

44508 LOWESTOFT SQ, ASHBURN, VA, 20147
Community: Lexington Square
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 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,...
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 Belmont Bay 680 WATERMANS DR APT 301, WOODBRIDGE, VA..., Woodbridge, VA 22191
$325,000

1 beds

|

2 baths

|

1,338 sq ft

|

Condo

680 WATERMANS DR APT 301, WOODBRIDGE, VA...
Community: Belmont Bay
Lansdowne Woods of Virginia 19355 CYPRESS RIDGE TER UNIT 503, LEESBU..., Leesburg, VA 20176
$379,900

2 beds

|

2 baths

|

1,251 sq ft

|

Condo

19355 CYPRESS RIDGE TER UNIT 503, LEESBU...
New Celebrate 12 PENSACOLA ST, FREDERICKSBURG, VA, 224..., Fredericksburg, VA 22406
$450,000

2 beds

|

2 baths

|

1,502 sq ft

12 PENSACOLA ST, FREDERICKSBURG, VA, 224...
Community: Celebrate
Want to learn more about 55+ communities in Winchester, VA? 55places can help!
Questions? Call us: (540) 773-2470
The Atrium at MetroWest 2960 VADEN DR # 2-312, FAIRFAX, VA, 2203..., Fairfax, VA 22031
$768,980

2 beds

|

2 baths

|

1,546 sq ft

|

Condo

2960 VADEN DR # 2-312, FAIRFAX, VA, 2203...
Four Seasons at Historic Virginia 16837 FOUR SEASONS DR, DUMFRIES, VA, 220..., Dumfries, VA 22025
$674,900

3 beds

|

3 baths

|

3,734 sq ft

16837 FOUR SEASONS DR, DUMFRIES, VA, 220...
Heritage Hunt 6135 FERRIER CT, GAINESVILLE, VA, 20155, Gainesville, VA 20155
$835,000

4 beds

|

4 baths

|

3,965 sq ft

6135 FERRIER CT, GAINESVILLE, VA, 20155
Community: Heritage Hunt
Falls Run 2 TURTLE CREEK WAY # 10-4, FREDERICKSBUR..., Fredericksburg, VA 22406
$379,000

2 beds

|

2 baths

|

1,657 sq ft

|

Condo

2 TURTLE CREEK WAY # 10-4, FREDERICKSBUR...
Community: Falls Run
Barley Woods 12205 GLEN OAKS DR, FREDERICKSBURG, VA, ..., Fredericksburg, VA 22407
$540,000

3 beds

|

2 baths

|

2,437 sq ft

12205 GLEN OAKS DR, FREDERICKSBURG, VA, ...
Community: Barley Woods
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.
Virginia Heritage at Lee's Parke 5417 E RICH MOUNTAIN WAY, FREDERICKSBURG..., Fredericksburg, VA 22407
$599,900

3 beds

|

4 baths

|

3,465 sq ft

5417 E RICH MOUNTAIN WAY, FREDERICKSBURG...
Regency at Creekside 5966 BOWES CREEK PL, GAINESVILLE, VA, 20..., Gainesville, VA 20155
$1,320,000

4 beds

|

5 baths

|

5,614 sq ft

5966 BOWES CREEK PL, GAINESVILLE, VA, 20...
Celebrate 121 AMBROSE LN, FREDERICKSBURG, VA, 2240..., Fredericksburg, VA 22406
$459,000

3 beds

|

3 baths

|

2,680 sq ft

121 AMBROSE LN, FREDERICKSBURG, VA, 2240...
Community: Celebrate
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...
Celebrate 35 MONTAUK AVE, FREDERICKSBURG, VA, 2240..., Fredericksburg, VA 22406
$475,000

2 beds

|

2 baths

|

1,642 sq ft

35 MONTAUK AVE, FREDERICKSBURG, VA, 2240...
Community: Celebrate
Want to learn more about 55+ communities in Winchester, VA? 55places can help!
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Celebrate 125 DENISON ST, FREDERICKSBURG, VA, 2240..., Fredericksburg, VA 22406
$579,000

3 beds

|

3 baths

|

2,736 sq ft

125 DENISON ST, FREDERICKSBURG, VA, 2240...
Community: Celebrate
Lansdowne Woods of Virginia 19365 CYPRESS RIDGE TER UNIT 1022, LEESB..., Leesburg, VA 20176
$370,000

2 beds

|

2 baths

|

1,105 sq ft

|

Condo

19365 CYPRESS RIDGE TER UNIT 1022, LEESB...
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
River Crossing at Spring Arbor 5701 SPRING ARBOR CIR, FREDERICKSBURG, V..., Fredericksburg, VA 22407
$475,000

3 beds

|

4 baths

|

2,249 sq ft

5701 SPRING ARBOR CIR, FREDERICKSBURG, V...
Potomac Green 44529 BLUERIDGE MEADOWS DR, ASHBURN, VA,..., Ashburn, VA 20147
$895,500

4 beds

|

4 baths

|

2,709 sq ft

44529 BLUERIDGE MEADOWS DR, ASHBURN, VA,...
Community: Potomac Green
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82 communities near Winchester
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