Call us at (540) 452-4199 to learn more about active adult communities in Winchester Area

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

159 homes near Winchester Area

Sort by:

Relevance

Relevance

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
No reviews yet Cedar Meadows
$400Ks - $400Ks
Cedar Meadows, White Post, VA
Resale Only | 55+ age-restricted | Built 2010 - 2022 | 129 homes
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
Want to learn more about 55+ communities in Winchester Area? 55places can help!
Questions? Call us: (540) 452-4199
No reviews yet Woodbrook Village
$300Ks - $300Ks
Woodbrook Village, Winchester, VA
Resale Only | 55+ age-restricted | Built 1999 - 2001 | 81 homes
No reviews yet Heritage Highlands
$300Ks - $400Ks
Heritage Highlands, Lovettsville, VA
Resale Only | 55+ age-restricted | Built 2017 - 2020 | 80 homes
No reviews yet The Highlands at Blue Rid...
$400Ks - $700Ks
The Highlands at Blue Rid..., Front Royal, VA
Resale Only | 55+ age-restricted | Built 2017 - 2019 | 42 homes
No reviews yet Cottage Glen
$400Ks - $400Ks
Cottage Glen, Winchester, VA
New and Resale | Age-targeted | Built 2018 - present | 25 homes
No reviews yet Abrams Chase
$500Ks - $500Ks
Abrams Chase, Winchester, VA
New Construction | 55+ age-restricted | Built 2020 - present | 13 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.
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
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
Want to learn more about 55+ communities in Winchester Area? 55places can help!
Questions? Call us: (540) 452-4199
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
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
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 Regency at Ashburn
$500Ks - $700Ks
Regency at Ashburn, Ashburn, VA
Resale Only | 55+ age-restricted | Built 2013 - 2020 | 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 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 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 Area? 55places can help!
Questions? Call us: (540) 452-4199
No reviews yet Regency at Belmont
$1Ms - $1Ms
Regency at Belmont, Ashburn, VA
New Construction | 55+ age-restricted | Built 2021 - present | 145 homes
5 rating (1 reviews) Gatherings at Wellington
$300Ks - $400Ks
Gatherings at Wellington, Manassas, VA
Resale Only | 55+ age-restricted | Built 2011 - 2016 | 135 homes
No reviews yet Vistas at Lansdowne
$500Ks - $800Ks
Vistas at Lansdowne, Lansdowne, VA
Resale Only | 55+ age-restricted | Built 2015 - 2020 | 120 homes
No reviews yet Lexington 7
$700Ks - $900Ks
Lexington 7, Ashburn, VA
Resale Only | 55+ age-restricted | Built 2017 - 2020 | 113 homes
No reviews yet Suffield Meadows
$400Ks - $500Ks
Suffield Meadows, Warrenton, VA
Resale Only | 55+ age-restricted | Built 2005 - 2011 | 112 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 JerMae Estates
$300Ks - $400Ks
JerMae Estates, Thurmont, MD
Resale Only | 55+ age-restricted | Built 2003 - 2008 | 108 homes
5 rating (1 reviews) Four Seasons at Vint Hill
$600Ks - $600Ks
Four Seasons at Vint Hill, Warrenton, VA
Resale Only | 55+ age-restricted | Built 2004 - 2006 | 100 homes
No reviews yet Albert Courts
$100Ks - $200Ks
Albert Courts, Thurmont, MD
Resale Only | 55+ age-restricted | Built 1991 - 2001 | 100 homes
No reviews yet Boxwood Villas
$500Ks - $600Ks
Boxwood Villas, Urbana, MD
Resale Only | 55+ age-restricted | Built 2019 - 2021 | 92 homes
No reviews yet The Village at Foxfield
$300Ks - $500Ks
The Village at Foxfield, Middletown, MD
Resale Only | 55+ age-restricted | Built 2003 - 2012 | 81 homes
Want to learn more about 55+ communities in Winchester Area? 55places can help!
Questions? Call us: (540) 452-4199
3.7 rating (3 reviews) Four Seasons at Ashburn V...
$400Ks - $400Ks
Four Seasons at Ashburn V..., Ashburn, VA
Resale Only | 55+ age-restricted | Built 2005 - 2005 | 80 homes
No reviews yet The Villages at Broadland...
$400Ks - $400Ks
The Villages at Broadland..., Ashburn, VA
New and Resale | 55+ age-restricted | Built 2013 - present | 78 homes
No reviews yet Cadence at Lansdowne
$700Ks - $700Ks
Cadence at Lansdowne, Lansdowne, VA
Resale Only | 55+ age-restricted | Built 2020 - 2024 | 74 homes
No reviews yet CobbleStone Estates
$400Ks - $500Ks
CobbleStone Estates, Hagerstown, MD
New and Resale | 55+ age-restricted | Built 2015 - present | 66 homes
No reviews yet The Village at Freedom Hi...
$300Ks - $300Ks
The Village at Freedom Hi..., Hagerstown, MD
New and Resale | 55+ age-restricted | Built 2007 - present | 66 homes
Four Seasons at Ashburn Village 21025 ROCKY KNOLL SQ 103, ASHBURN, VA, 2..., Ashburn, VA 20147
$459,000

2 beds

|

2 baths

|

1,359 sq ft

|

Condo

21025 ROCKY KNOLL SQ 103, ASHBURN, VA, 2...
Trilogy® at Lake Frederick 130 GROSBEAK CT, LAKE FREDERICK, VA, 226..., Lake Frederick, VA 22630
$939,900

4 beds

|

4 baths

|

4,921 sq ft

130 GROSBEAK CT, LAKE FREDERICK, VA, 226...
Trilogy® at Lake Frederick 110 FRITILLARY CT, LAKE FREDERICK, VA, 2..., Lake Frederick, VA 22630
$430,000

3 beds

|

4 baths

|

2,325 sq ft

110 FRITILLARY CT, LAKE FREDERICK, VA, 2...
Trilogy® at Lake Frederick 111 WAKE ROBIN CT, LAKE FREDERICK, VA, 2..., Lake Frederick, VA 22630
$450,000

4 beds

|

4 baths

|

2,248 sq ft

111 WAKE ROBIN CT, LAKE FREDERICK, VA, 2...
Lansdowne Woods of Virginia 19370 MAGNOLIA GROVE SQ 208, LEESBURG, V..., Leesburg, VA 20176
$420,000

2 beds

|

2 baths

|

1,440 sq ft

|

Condo

19370 MAGNOLIA GROVE SQ 208, LEESBURG, V...
Want to learn more about 55+ communities in Winchester Area? 55places can help!
Questions? Call us: (540) 452-4199
Heritage Hunt 6046 GALLANT FOX CT, GAINESVILLE, VA, 20..., Gainesville, VA 20155
$643,000

4 beds

|

3 baths

|

1,943 sq ft

6046 GALLANT FOX CT, GAINESVILLE, VA, 20...
Community: Heritage Hunt
Heritage Hunt 13882 CINCH LN, GAINESVILLE, VA, 20155, Gainesville, VA 20155
$835,000

3 beds

|

4 baths

|

3,192 sq ft

13882 CINCH LN, GAINESVILLE, VA, 20155
Community: Heritage Hunt
Vistas at Lansdowne 44251 SILVERPALM GROVE TER, LEESBURG, VA..., Leesburg, VA 20176
$865,000

3 beds

|

4 baths

|

3,974 sq ft

44251 SILVERPALM GROVE TER, LEESBURG, VA...
Community: Vistas at Lansdowne
Heritage Hunt 6848 TRED AVON PL, GAINESVILLE, VA, 2015..., Gainesville, VA 20155
$769,000

3 beds

|

3 baths

|

2,520 sq ft

6848 TRED AVON PL, GAINESVILLE, VA, 2015...
Community: Heritage Hunt
Trilogy® at Lake Frederick 142 RUFFED GROUSE CT, LAKE FREDERICK, VA..., Lake Frederick, VA 22630
$799,999

3 beds

|

3 baths

|

2,937 sq ft

142 RUFFED GROUSE CT, LAKE FREDERICK, VA...
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.
Lansdowne Woods of Virginia 19375 CYPRESS RIDGE TER UNIT 206, LEESBU..., Leesburg, VA 20176
$424,900

2 beds

|

2 baths

|

1,441 sq ft

|

Condo

19375 CYPRESS RIDGE TER UNIT 206, LEESBU...
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
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 7 44480 LOWESTOFT SQ, ASHBURN, VA, 20147, Ashburn, VA 20147
$794,990

3 beds

|

3 baths

|

3,088 sq ft

44480 LOWESTOFT SQ, ASHBURN, VA, 20147
Community: Lexington 7
Lexington Square 44480 LOWESTOFT SQ, ASHBURN, VA, 20147, Ashburn, VA 20147
$794,990

3 beds

|

3 baths

|

3,088 sq ft

44480 LOWESTOFT SQ, ASHBURN, VA, 20147
Community: Lexington Square
Want to learn more about 55+ communities in Winchester Area? 55places can help!
Questions? Call us: (540) 452-4199
Abrams Chase 112 AMBERFIELD CT, WINCHESTER, VA, 22602, Winchester, VA 22602
$499,500

2 beds

|

2 baths

|

1,609 sq ft

112 AMBERFIELD CT, WINCHESTER, VA, 22602
Community: Abrams Chase
Lansdowne Woods of Virginia 19355 CYPRESS RIDGE TER UNIT 921, LEESBU..., Leesburg, VA 20176
$495,000

2 beds

|

2 baths

|

1,509 sq ft

|

Condo

19355 CYPRESS RIDGE TER UNIT 921, LEESBU...
Heritage Hunt 13685 PADDOCK CT, GAINESVILLE, VA, 20155, Gainesville, VA 20155
$775,000

3 beds

|

3 baths

|

2,951 sq ft

13685 PADDOCK CT, GAINESVILLE, VA, 20155
Community: Heritage Hunt
Gatherings at Wellington 9200 CHARLESTON DR 408, MANASSAS, VA, 20..., Manassas, VA 20110
$375,000

2 beds

|

2 baths

|

1,417 sq ft

|

Condo

9200 CHARLESTON DR 408, MANASSAS, VA, 20...
Lexington Square 44470 COALPORT TER, ASHBURN, VA, 20147, Ashburn, VA 20147
$977,626

4 beds

|

4 baths

|

4,089 sq ft

44470 COALPORT TER, 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.
Lexington 7 44470 COALPORT TER, ASHBURN, VA, 20147, Ashburn, VA 20147
$977,626

4 beds

|

4 baths

|

4,089 sq ft

44470 COALPORT TER, ASHBURN, VA, 20147
Community: Lexington 7
Regency at Dominion Valley 15130 HEATHER MILL LN 102, HAYMARKET, VA..., Haymarket, VA 20169
$415,000

2 beds

|

2 baths

|

1,499 sq ft

|

Condo

15130 HEATHER MILL LN 102, HAYMARKET, VA...
Regency at Dominion Valley 15120 HEATHER MILL LN APT 304, HAYMARKET..., Haymarket, VA 20169
$465,000

2 beds

|

2 baths

|

1,499 sq ft

|

Condo

15120 HEATHER MILL LN APT 304, HAYMARKET...
Woodbrook Village 201 ROSEWOOD LN, WINCHESTER, VA, 22602, Winchester, VA 22602
$375,000

2 beds

|

2 baths

|

1,692 sq ft

201 ROSEWOOD LN, WINCHESTER, VA, 22602
Community: Woodbrook Village
Trilogy® at Lake Frederick 120 BAYHILL TER, LAKE FREDERICK, VA, 226..., Lake Frederick, VA 22630
$434,900

3 beds

|

3 baths

|

2,311 sq ft

120 BAYHILL TER, LAKE FREDERICK, VA, 226...
Want to learn more about 55+ communities in Winchester Area? 55places can help!
Questions? Call us: (540) 452-4199
Heritage Hunt 6805 TRED AVON PL, GAINESVILLE, VA, 2015..., Gainesville, VA 20155
$875,000

4 beds

|

4 baths

|

2,653 sq ft

6805 TRED AVON PL, GAINESVILLE, VA, 2015...
Community: Heritage Hunt
Lansdowne Woods of Virginia 19355 CYPRESS RIDGE TER UNIT 414, LEESBU..., Leesburg, VA 20176
$299,900

2 beds

|

2 baths

|

1,038 sq ft

|

Condo

19355 CYPRESS RIDGE TER UNIT 414, LEESBU...
The Retreat at Poland Hill 43453 BETTYS FARM DR, CHANTILLY, VA, 201..., Chantilly, VA 20152
$949,900

4 beds

|

4 baths

|

4,063 sq ft

43453 BETTYS FARM DR, CHANTILLY, VA, 201...
Lansdowne Woods of Virginia 19355 CYPRESS RIDGE TER 203, LEESBURG, V..., Leesburg, VA 20176
$399,000

2 beds

|

2 baths

|

1,251 sq ft

|

Condo

19355 CYPRESS RIDGE TER 203, LEESBURG, V...
Heritage Hunt 13891 CHELMSFORD DR APT 201, GAINESVILLE..., Gainesville, VA 20155
$389,000

2 beds

|

2 baths

|

1,206 sq ft

|

Condo

13891 CHELMSFORD DR APT 201, GAINESVILLE...
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 121 COWBIRD ST, LAKE FREDERICK, VA, 2263..., Lake Frederick, VA 22630
$625,000

3 beds

|

3 baths

|

2,457 sq ft

121 COWBIRD ST, LAKE FREDERICK, VA, 2263...
Birchwood at Brambleton 42788 MACBETH TER, ASHBURN, VA, 20148, Ashburn, VA 20148
$849,990

3 beds

|

3 baths

|

2,669 sq ft

42788 MACBETH TER, ASHBURN, VA, 20148
Lansdowne Woods of Virginia 19375 CYPRESS RIDGE TER 212, LEESBURG, V..., Leesburg, VA 20176
$465,000

3 beds

|

2 baths

|

1,475 sq ft

|

Condo

19375 CYPRESS RIDGE TER 212, LEESBURG, V...
Regency at Dominion Valley 15201 WEISKOPF CT, HAYMARKET, VA, 20169, Haymarket, VA 20169
$850,000

4 beds

|

3 baths

|

3,140 sq ft

15201 WEISKOPF CT, HAYMARKET, VA, 20169
Four Seasons at Ashburn Village 44485 CHAMBERLAIN TER UNIT 205, ASHBURN,..., Ashburn, VA 20147
$450,000

2 beds

|

2 baths

|

1,612 sq ft

|

Condo

44485 CHAMBERLAIN TER UNIT 205, ASHBURN,...
Want to learn more about 55+ communities in Winchester Area? 55places can help!
Questions? Call us: (540) 452-4199
Birchwood at Brambleton 23606 HAVELOCK WALK TER, ASHBURN, VA, 20..., Ashburn, VA 20148
$579,999

3 beds

|

3 baths

|

2,592 sq ft

|

Condo

23606 HAVELOCK WALK TER, ASHBURN, VA, 20...
Lansdowne Woods of Virginia 19355 CYPRESS RIDGE TER 521, LEESBURG, V..., Leesburg, VA 20176
$475,000

2 beds

|

2 baths

|

1,509 sq ft

|

Condo

19355 CYPRESS RIDGE TER 521, LEESBURG, V...
Central Parke at Lowes Island 20751 ROYAL PALACE SQ UNIT 104, STERLING..., Sterling, VA 20165
$465,000

3 beds

|

2 baths

|

1,816 sq ft

|

Condo

20751 ROYAL PALACE SQ UNIT 104, STERLING...
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
Heritage Hunt 13890 CHELMSFORD DR APT 313, GAINESVILLE..., Gainesville, VA 20155
$379,900

2 beds

|

2 baths

|

1,206 sq ft

|

Condo

13890 CHELMSFORD DR APT 313, GAINESVILLE...
Community: Heritage Hunt



Frequently Asked Questions


159 homes near Winchester Area
Remove Boundaries ×
Map Satellite

Want to learn more about 55+ communities in Winchester Area?

Call us: (540) 452-4199

Call Us Call Us
Scroll to Top