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

258 homes 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...
$300Ks - $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.
Penn National
$200Ks - $600Ks
Penn National, Fayetteville, PA
New and Resale | Age-targeted | Built 1968 - present | 1,100 homes
3.1 rating (7 reviews) Celebrate
$300Ks - $600Ks
Celebrate, Fredericksburg, VA
New and Resale | 55+ age-restricted | Built 2008 - 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
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'...
$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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Questions? Call us: (540) 773-2470
ThreeOaksâ„¢
$400Ks - $800Ks
ThreeOaksâ„¢, Culpeper, VA
New Construction | 55+ age-restricted | Built 2024 - present | 268 homes
Regency at Ashburn
$800Ks - $900Ks
Regency at Ashburn, Ashburn, VA
Resale Only | 55+ age-restricted | Built 2013 - 2020 | 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
Want to learn more about 55+ communities in Winchester? 55places can help!
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
Virginia Heritage at Lee's Parke 5512 W RICH MOUNTAIN WAY, FREDERICKSBURG..., Fredericksburg, VA 22407
$499,900

3 beds

|

3 baths

|

2,481 sq ft

5512 W RICH MOUNTAIN WAY, FREDERICKSBURG...
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
Virginia Heritage at Lee's Parke 5105 SEWELLS POINTE DR, FREDERICKSBURG, ..., Fredericksburg, VA 22407
$619,000

4 beds

|

4 baths

|

4,189 sq ft

5105 SEWELLS POINTE DR, FREDERICKSBURG, ...
Heritage Hunt 13154 TRIPLE CROWN LOOP, GAINESVILLE, VA..., Gainesville, VA 20155
$725,000

3 beds

|

4 baths

|

3,195 sq ft

13154 TRIPLE CROWN LOOP, GAINESVILLE, VA...
Community: Heritage Hunt
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
Want to learn more about 55+ communities in Winchester? 55places can help!
Questions? Call us: (540) 773-2470
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...
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 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
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
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
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.
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
Lansdowne Woods of Virginia 19385 CYPRESS RIDGE TER UNIT 404, LEESBU..., Leesburg, VA 20176
$329,900

2 beds

|

2 baths

|

1,038 sq ft

|

Condo

19385 CYPRESS RIDGE TER UNIT 404, LEESBU...
Heritage Hunt 6920 NETHERSTONE CT, GAINESVILLE, VA, 20..., Gainesville, VA 20155
$625,000

2 beds

|

3 baths

|

2,745 sq ft

6920 NETHERSTONE CT, GAINESVILLE, VA, 20...
Community: Heritage Hunt
Lansdowne Woods of Virginia 19365 CYPRESS RIDGE TER UNIT 1102, LEESB..., Leesburg, VA 20176
$399,000

2 beds

|

2 baths

|

1,105 sq ft

|

Condo

19365 CYPRESS RIDGE TER UNIT 1102, LEESB...
Four Seasons at Virginia Crossing 13970 ENGLEFIELD DR UNIT 303, WOODBRIDGE..., Woodbridge, VA 22193
$530,000

2 beds

|

2 baths

|

1,801 sq ft

|

Condo

13970 ENGLEFIELD DR UNIT 303, WOODBRIDGE...
Want to learn more about 55+ communities in Winchester? 55places can help!
Questions? Call us: (540) 773-2470
Gatherings at Wellington 9200 CHARLESTON DR 407, MANASSAS, VA, 20..., Manassas, VA 20110
$438,000

3 beds

|

2 baths

|

2,006 sq ft

|

Condo

9200 CHARLESTON DR 407, MANASSAS, VA, 20...
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
Celebrate 196 DENISON ST, FREDERICKSBURG, VA, 2240..., Fredericksburg, VA 22406
$460,000

2 beds

|

2 baths

|

1,632 sq ft

196 DENISON ST, FREDERICKSBURG, VA, 2240...
Community: Celebrate
Lansdowne Woods of Virginia 19385 CYPRESS RIDGE TER UNIT 920, LEESBU..., Leesburg, VA 20176
$450,000

3 beds

|

2 baths

|

1,475 sq ft

|

Condo

19385 CYPRESS RIDGE TER UNIT 920, LEESBU...
Heritage Hunt 13879 CRABTREE WAY, GAINESVILLE, VA, 201..., Gainesville, VA 20155
$725,000

4 beds

|

3 baths

|

3,151 sq ft

13879 CRABTREE WAY, GAINESVILLE, VA, 201...
Community: Heritage Hunt
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.
Trilogy® at Lake Frederick 117 HARVESTER DR, LAKE FREDERICK, VA, 22..., Lake Frederick, VA 22630
$899,000

4 beds

|

5 baths

|

6,096 sq ft

117 HARVESTER DR, LAKE FREDERICK, VA, 22...
Gatherings at Potomac Station 750 MOUNT AIRY TER NE UNIT 304, LEESBURG..., Leesburg, VA 20176
$499,999

2 beds

|

2 baths

|

1,532 sq ft

|

Condo

750 MOUNT AIRY TER NE UNIT 304, LEESBURG...
Gatherings at Potomac Station 750 MOUNT AIRY TER NE UNIT 206A, LEESBUR..., Leesburg, VA 20176
$449,999

2 beds

|

2 baths

|

1,532 sq ft

|

Condo

750 MOUNT AIRY TER NE UNIT 206A, LEESBUR...
Gatherings at Potomac Station 750 MOUNT AIRY TER NE UNIT 403A, LEESBUR..., Leesburg, VA 20176
$484,999

2 beds

|

2 baths

|

1,410 sq ft

|

Condo

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

2 beds

|

2 baths

|

1,410 sq ft

|

Condo

700 MOUNT AIRY TER NE UNIT 403A, LEESBUR...
Want to learn more about 55+ communities in Winchester? 55places can help!
Questions? Call us: (540) 773-2470
Lansdowne Woods of Virginia 19385 CYPRESS RIDGE TER 815, LEESBURG, V..., Leesburg, VA 20176
$498,000

3 beds

|

2 baths

|

1,475 sq ft

|

Condo

19385 CYPRESS RIDGE TER 815, LEESBURG, V...
Liberty Grove 8600 LIBERTY TRL UNIT 303, MANASSAS, VA,..., Manassas, VA 20110
$329,900

2 beds

|

3 baths

|

1,743 sq ft

|

Condo

8600 LIBERTY TRL UNIT 303, MANASSAS, VA,...
Community: Liberty Grove
Birchwood at Brambleton 23640 BOLTON CRESCENT TER # 13-204, ASHB..., Ashburn, VA 20148
$484,990

2 beds

|

2 baths

|

1,431 sq ft

|

Condo

23640 BOLTON CRESCENT TER # 13-204, ASHB...
Lansdowne Woods of Virginia 19355 CYPRESS RIDGE TER 114, LEESBURG, V..., Leesburg, VA 20176
$350,000

2 beds

|

2 baths

|

1,038 sq ft

|

Condo

19355 CYPRESS RIDGE TER 114, LEESBURG, V...
Cadence at Lansdowne 43899 SIREN SONG TER, LEESBURG, VA, 2017..., Leesburg, VA 20176
$785,000

3 beds

|

4 baths

|

2,780 sq ft

43899 SIREN SONG TER, LEESBURG, VA, 2017...
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.
Belmont Bay 680 WATERMANS DR APT 505, WOODBRIDGE, VA..., Woodbridge, VA 22191
$419,900

2 beds

|

3 baths

|

1,457 sq ft

|

Condo

680 WATERMANS DR APT 505, WOODBRIDGE, VA...
Community: Belmont Bay
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
Trilogy® at Lake Frederick 103 BURKWOOD TER, LAKE FREDERICK, VA, 22..., Lake Frederick, VA 22630
$410,000

3 beds

|

3 baths

|

2,376 sq ft

103 BURKWOOD TER, LAKE FREDERICK, VA, 22...
Lansdowne Woods of Virginia 19385 CYPRESS RIDGE TER 914, LEESBURG, V..., Leesburg, VA 20176
$499,000

2 beds

|

2 baths

|

1,509 sq ft

|

Condo

19385 CYPRESS RIDGE TER 914, LEESBURG, V...
Trilogy® at Lake Frederick 105 BAYHILL TER, LAKE FREDERICK, VA, 226..., Lake Frederick, VA 22630
$369,900

3 beds

|

3 baths

|

1,962 sq ft

105 BAYHILL TER, LAKE FREDERICK, VA, 226...
Want to learn more about 55+ communities in Winchester? 55places can help!
Questions? Call us: (540) 773-2470
Keswick Villas 8859 MARLOW DR, SPOTSYLVANIA, VA, 22551, Spotsylvania, VA 22551
$410,000

3 beds

|

2 baths

|

1,388 sq ft

8859 MARLOW DR, SPOTSYLVANIA, VA, 22551
Community: Keswick Villas
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
Birchwood at Brambleton 43221 GREELEY SQ, ASHBURN, VA, 20148, Ashburn, VA 20148
$1,228,000

3 beds

|

4 baths

|

4,124 sq ft

43221 GREELEY SQ, ASHBURN, VA, 20148
Birchwood at Brambleton 23631 HAVELOCK WALK TER 220, ASHBURN, VA..., Ashburn, VA 20148
$529,999

3 beds

|

2 baths

|

1,971 sq ft

|

Condo

23631 HAVELOCK WALK TER 220, ASHBURN, VA...
River Crossing at Spring Arbor 5806 SPRING ARBOR LN, FREDERICKSBURG, VA..., Fredericksburg, VA 22407
$465,000

3 beds

|

3 baths

|

1,925 sq ft

5806 SPRING ARBOR LN, FREDERICKSBURG, VA...
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258 homes near Winchester
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