Call us at (540) 773-2470 to learn more about active adult communities in Winchester

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

278 homes near Winchester

Sort by:

Relevance

Relevance

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
Want to learn more about 55+ communities in Winchester? 55places can help!
Questions? Call us: (540) 773-2470
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.
No reviews yet Penn National
$300Ks - $500Ks
Penn National, Fayetteville, PA
New and Resale | Age-targeted | Built 1968 - present | 1,100 homes
2.8 rating (6 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 - $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
Want to learn more about 55+ communities in Winchester? 55places can help!
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
Potomac Green 20458 VALLEY FALLS SQ, ASHBURN, VA, 2014..., Ashburn, VA 20147
$650,000

2 beds

|

3 baths

|

2,060 sq ft

20458 VALLEY FALLS SQ, ASHBURN, VA, 2014...
Community: Potomac Green
Birchwood at Brambleton 43244 GREELEY SQ, ASHBURN, VA, 20148, Ashburn, VA 20148
$965,000

3 beds

|

4 baths

|

2,908 sq ft

43244 GREELEY SQ, ASHBURN, VA, 20148
Potomac Green 20515 LITTLE CREEK TER UNIT 101, ASHBURN..., Ashburn, VA 20147
$435,000

2 beds

|

2 baths

|

1,347 sq ft

|

Condo

20515 LITTLE CREEK TER UNIT 101, ASHBURN...
Community: Potomac Green
Summerlake 11611 HAMPSHIRE CT, FREDERICKSBURG, VA, ..., Fredericksburg, VA 22407
$389,900

3 beds

|

3 baths

|

1,969 sq ft

11611 HAMPSHIRE CT, FREDERICKSBURG, VA, ...
Community: Summerlake
New Celebrate 9 BRANT CT, FREDERICKSBURG, VA, 22406, Fredericksburg, VA 22406
$548,750

3 beds

|

3 baths

|

2,656 sq ft

9 BRANT CT, FREDERICKSBURG, VA, 22406
Community: Celebrate
Want to learn more about 55+ communities in Winchester? 55places can help!
Questions? Call us: (540) 773-2470
Four Seasons at Vint Hill 3599 SUTHERLAND CT, WARRENTON, VA, 20187, Warrenton, VA 20187
$624,900

3 beds

|

2 baths

|

1,942 sq ft

3599 SUTHERLAND CT, WARRENTON, VA, 20187
New Trilogy® at Lake Frederick 112 VICEROY WAY, LAKE FREDERICK, VA, 226..., Lake Frederick, VA 22630
$739,000

3 beds

|

3 baths

|

3,564 sq ft

112 VICEROY WAY, LAKE FREDERICK, VA, 226...
Trilogy® at Lake Frederick 172 TROUT LILY DR, LAKE FREDERICK, VA, 2..., Lake Frederick, VA 22630
$411,900

3 beds

|

3 baths

|

2,175 sq ft

172 TROUT LILY DR, LAKE FREDERICK, VA, 2...
New Twin Lake Villas 3611 TWIN LAKE BLVD, ORANGE, VA, 22960, Orange, VA 22960
$449,500

3 beds

|

2 baths

|

1,396 sq ft

3611 TWIN LAKE BLVD, ORANGE, VA, 22960
Community: Twin Lake Villas
Potomac Green 20600 HOPE SPRING TER 202, ASHBURN, VA, ..., Ashburn, VA 20147
$445,000

2 beds

|

2 baths

|

1,347 sq ft

|

Condo

20600 HOPE SPRING TER 202, ASHBURN, VA, ...
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.
Keswick Villas 7809 BEXLEY LN, SPOTSYLVANIA, VA, 22551, Spotsylvania, VA 22551
$649,800

5 beds

|

3 baths

|

3,735 sq ft

7809 BEXLEY LN, SPOTSYLVANIA, VA, 22551
Community: Keswick Villas
Falls Run 21 BUCHANAN CT, FREDERICKSBURG, VA, 2240..., Fredericksburg, VA 22406
$455,000

3 beds

|

3 baths

|

2,229 sq ft

21 BUCHANAN CT, FREDERICKSBURG, VA, 2240...
Community: Falls Run
Trilogy® at Lake Frederick 114 CHOKE CHERRY CT, LAKE FREDERICK, VA,..., Lake Frederick, VA 22630
$499,900

4 beds

|

4 baths

|

2,567 sq ft

114 CHOKE CHERRY CT, LAKE FREDERICK, VA,...
New Birchwood at Brambleton 43089 GREELEY SQ, ASHBURN, VA, 20148, Ashburn, VA 20148
$983,060

3 beds

|

3 baths

|

2,491 sq ft

43089 GREELEY SQ, ASHBURN, VA, 20148
Liberty Grove 8600 LIBERTY TRL 102, MANASSAS, VA, 2011..., Manassas, VA 20110
$320,000

1 beds

|

2 baths

|

1,131 sq ft

|

Condo

8600 LIBERTY TRL 102, MANASSAS, VA, 2011...
Community: Liberty Grove
Want to learn more about 55+ communities in Winchester? 55places can help!
Questions? Call us: (540) 773-2470
New Birchwood at Brambleton 23640 BOLTON CRESCENT TER # 13-306, ASHB..., Ashburn, VA 20148
$579,990

2 beds

|

2 baths

|

1,413 sq ft

|

Condo

23640 BOLTON CRESCENT TER # 13-306, ASHB...
New Birchwood at Brambleton 23640 BOLTON CRESCENT TER # 13-304, ASHB..., Ashburn, VA 20148
$579,990

2 beds

|

2 baths

|

1,419 sq ft

|

Condo

23640 BOLTON CRESCENT TER # 13-304, ASHB...
New Birchwood at Brambleton 23640 BOLTON CRESCENT TER # 13-305, ASHB..., Ashburn, VA 20148
$724,990

3 beds

|

2 baths

|

1,969 sq ft

|

Condo

23640 BOLTON CRESCENT TER # 13-305, ASHB...
Virginia Heritage at Lee's Parke 6020 E GREENBRIER RIVER RD, FREDERICKSBU..., Fredericksburg, VA 22407
$610,000

4 beds

|

3 baths

|

3,317 sq ft

6020 E GREENBRIER RIVER RD, FREDERICKSBU...
Heritage Hunt 13404 FIELDSTONE WAY, GAINESVILLE, VA, 2..., Gainesville, VA 20155
$875,000

4 beds

|

4 baths

|

4,069 sq ft

13404 FIELDSTONE WAY, GAINESVILLE, VA, 2...
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.
Celebrate 43 BATTERY POINT DR, FREDERICKSBURG, VA,..., Fredericksburg, VA 22406
$560,000

3 beds

|

3 baths

|

2,192 sq ft

43 BATTERY POINT DR, FREDERICKSBURG, VA,...
Community: Celebrate
Cascades at Embrey Mill 225 SMOKEBUSH DR, STAFFORD, VA, 22554, Stafford, VA 22554
$649,900

4 beds

|

4 baths

|

3,000 sq ft

225 SMOKEBUSH DR, STAFFORD, VA, 22554
Central Parke at Lowes Island 20745 ROYAL PALACE SQ 102, STERLING, VA,..., Sterling, VA 20165
$425,000

2 beds

|

2 baths

|

1,692 sq ft

|

Condo

20745 ROYAL PALACE SQ 102, STERLING, VA,...
New Four Seasons at Charlottesville 452 MISTLAND TRL, RUCKERSVILLE, VA, 2296..., Ruckersville, VA 22968
$548,000

2 beds

|

2 baths

|

2,585 sq ft

452 MISTLAND TRL, RUCKERSVILLE, VA, 2296...
Cedar Meadows 124 BLUETS DR, WHITE POST, VA, 22663, White Post, VA 22663
$432,000

2 beds

|

2 baths

|

1,613 sq ft

124 BLUETS DR, WHITE POST, VA, 22663
Community: Cedar Meadows
Want to learn more about 55+ communities in Winchester? 55places can help!
Questions? Call us: (540) 773-2470
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
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...
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.
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...
Lansdowne Woods of Virginia 19375 CYPRESS RIDGE TER 620, LEESBURG, V..., Leesburg, VA 20176
$385,000

2 beds

|

2 baths

|

1,038 sq ft

|

Condo

19375 CYPRESS RIDGE TER 620, LEESBURG, V...
Potomac Green 44365 ADARE MANOR SQ, ASHBURN, VA, 20147, Ashburn, VA 20147
$669,990

2 beds

|

3 baths

|

2,060 sq ft

44365 ADARE MANOR SQ, ASHBURN, VA, 20147
Community: Potomac Green
Want to learn more about 55+ communities in Winchester? 55places can help!
Questions? Call us: (540) 773-2470
Potomac Green 20620 HOPE SPRING TER 206, ASHBURN, VA, ..., Ashburn, VA 20147
$464,989

2 beds

|

2 baths

|

1,586 sq ft

|

Condo

20620 HOPE SPRING TER 206, ASHBURN, VA, ...
Community: Potomac Green
Keswick Villas 7816 BEXLEY LN, SPOTSYLVANIA, VA, 22551, Spotsylvania, VA 22551
$679,999

5 beds

|

4 baths

|

4,134 sq ft

7816 BEXLEY LN, SPOTSYLVANIA, VA, 22551
Community: Keswick Villas
Keswick Villas 8720 AFTON DR, SPOTSYLVANIA, VA, 22551, Spotsylvania, VA 22551
$669,999

4 beds

|

3 baths

|

2,683 sq ft

8720 AFTON DR, SPOTSYLVANIA, VA, 22551
Community: Keswick Villas
Lansdowne Woods of Virginia 19385 CYPRESS RIDGE TER 621, LEESBURG, V..., Leesburg, VA 20176
$369,000

2 beds

|

2 baths

|

1,246 sq ft

|

Condo

19385 CYPRESS RIDGE TER 621, LEESBURG, V...
Vistas at Lansdowne 19400 LANSDOWNE WOODS BLVD 110, LEESBURG..., Leesburg, VA 20176
$550,000

2 beds

|

2 baths

|

1,680 sq ft

|

Condo

19400 LANSDOWNE WOODS BLVD 110, LEESBURG...
Community: Vistas at Lansdowne

Frequently Asked Questions


Want more information about active adult communities around Winchester?

Global - Lead Form - Buyer or Renter

*55places does not provide or maintain community HOA information.
By requesting more information, you agree that 55places may call, text, or email you about your inquiry, which may be made with automated means (including recorded voice messages, SMS, or text messages). You understand that your consent is not a prerequisite for buying, selling or renting a property. You may revoke your consent at any time by contacting [email protected]. Message/data rates may apply. You also agree to 55places.com’s Privacy Policy and Terms of Use.

278 homes near Winchester
Remove Boundaries ×
Map Satellite

Want to learn more about 55+ communities in Winchester?

Call us: (540) 773-2470

Call Us Call Us
Scroll to Top