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

46 communities near Winchester Area

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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
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
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
Want to learn more about 55+ communities in Winchester Area? 55places can help!
Questions? Call us: (540) 452-4199
Woodbrook Village
$300Ks - $300Ks
Woodbrook Village, Winchester, VA
Resale Only | 55+ age-restricted | Built 1999 - 2001 | 81 homes
Heritage Highlands
$300Ks - $400Ks
Heritage Highlands, Lovettsville, VA
Resale Only | 55+ age-restricted | Built 2017 - 2020 | 80 homes
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
Cottage Glen
$400Ks - $400Ks
Cottage Glen, Winchester, VA
New and Resale | Age-targeted | Built 2018 - present | 25 homes
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
$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
$800Ks - $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
5 rating (1 reviews) Regency at Dominion Valle...
$400Ks - $700Ks
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
The Woodlands of Urbana
$600Ks - $600Ks
The Woodlands of Urbana, Urbana, MD
New Construction | 55+ age-restricted | Built 2019 - present | 565 homes
5 rating (1 reviews) Crestwood Village
$300Ks - $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
3 rating (2 reviews) Dunbarton
$600Ks - $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
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 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
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 - $900Ks
Regency at Creekside, Gainesville, VA
Resale Only | 55+ age-restricted | Built 2016 - 2020 | 208 homes
Central Parke at Lowes Is...
$400Ks - $700Ks
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
Regency at Belmont
$900Ks - $900Ks
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
Vistas at Lansdowne
$500Ks - $800Ks
Vistas at Lansdowne, Lansdowne, VA
Resale Only | 55+ age-restricted | Built 2015 - 2020 | 120 homes
Lexington 7
$800Ks - $800Ks
Lexington 7, Ashburn, VA
Resale Only | 55+ age-restricted | Built 2017 - 2020 | 113 homes
Suffield Meadows
$300Ks - $400Ks
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.
JerMae Estates
$400Ks - $500Ks
JerMae Estates, Thurmont, MD
Resale Only | 55+ age-restricted | Built 2003 - 2008 | 108 homes
Albert Courts
$100Ks - $200Ks
Albert Courts, Thurmont, MD
Resale Only | 55+ age-restricted | Built 1991 - 2001 | 100 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
Boxwood Villas
$500Ks - $600Ks
Boxwood Villas, Urbana, MD
Resale Only | 55+ age-restricted | Built 2019 - 2021 | 92 homes
The Village at Foxfield
$500Ks - $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
The Villages at Broadland...
$400Ks - $400Ks
The Villages at Broadland..., Ashburn, VA
New and Resale | 55+ age-restricted | Built 2013 - present | 78 homes
Cadence at Lansdowne
$700Ks - $700Ks
Cadence at Lansdowne, Lansdowne, VA
Resale Only | 55+ age-restricted | Built 2020 - 2024 | 74 homes
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
CobbleStone Estates
$400Ks - $500Ks
CobbleStone Estates, Hagerstown, MD
New and Resale | 55+ age-restricted | Built 2015 - present | 66 homes
1...2
Emerald Pointe 19554 TURQUOISE DR V219, HAGERSTOWN, MD,..., Hagerstown, MD 21742
$484,900

2 beds

|

2 baths

19554 TURQUOISE DR V219, HAGERSTOWN, MD,...
Community: Emerald Pointe
CobbleStone Estates 9616 COBBLE STONE CT, HAGERSTOWN, MD, 21..., Hagerstown, MD 21740
$395,000

2 beds

|

2 baths

|

1,561 sq ft

9616 COBBLE STONE CT, HAGERSTOWN, MD, 21...
Community: CobbleStone Estates
Crestwood Village 5722 BOX ELDER CT, FREDERICK, MD, 21703, Frederick, MD 21703
$349,000

2 beds

|

2 baths

|

1,264 sq ft

5722 BOX ELDER CT, FREDERICK, MD, 21703
Community: Crestwood Village
The Village at Freedom Hills 13946 PATRIOT WAY, HAGERSTOWN, MD, 21740, Hagerstown, MD 21740
$399,900

2 beds

|

2 baths

|

1,484 sq ft

13946 PATRIOT WAY, HAGERSTOWN, MD, 21740
The Woodlands of Urbana 3207 THORNAPPLE DR, FREDERICK, MD, 21704, Frederick, MD 21704
$609,900

3 beds

|

3 baths

|

1,677 sq ft

3207 THORNAPPLE DR, FREDERICK, MD, 21704
Want to learn more about 55+ communities in Winchester Area? 55places can help!
Questions? Call us: (540) 452-4199
The Village at Foxfield 1 KELLER LN, MIDDLETOWN, MD, 21769, Middletown, MD 21769
$574,900

3 beds

|

3 baths

|

3,161 sq ft

1 KELLER LN, MIDDLETOWN, MD, 21769
The Woodlands of Urbana 3225 THORNAPPLE DR, FREDERICK, MD, 21704, Frederick, MD 21704
$615,000

3 beds

|

3 baths

|

1,816 sq ft

3225 THORNAPPLE DR, FREDERICK, MD, 21704
Crestwood Village 7043 BASSWOOD RD, FREDERICK, MD, 21703, Frederick, MD 21703
$339,999

2 beds

|

2 baths

|

1,225 sq ft

7043 BASSWOOD RD, FREDERICK, MD, 21703
Community: Crestwood Village
The Woodlands of Urbana 2928 HERB GARDEN DR, FREDERICK, MD, 2170..., Frederick, MD 21704
$725,000

3 beds

|

4 baths

|

3,634 sq ft

2928 HERB GARDEN DR, FREDERICK, MD, 2170...
Emerald Pointe 19446 SAPPHIRE DR, HAGERSTOWN, MD, 21742, Hagerstown, MD 21742
$359,900

2 beds

|

2 baths

|

1,834 sq ft

19446 SAPPHIRE DR, HAGERSTOWN, MD, 21742
Community: Emerald Pointe
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 13336 MARQUISE DR, HAGERSTOWN, MD, 21742, Hagerstown, MD 21742
$449,900

2 beds

|

2 baths

|

2,615 sq ft

13336 MARQUISE DR, HAGERSTOWN, MD, 21742
Community: Emerald Pointe
Emerald Pointe 13430 MARQUISE DR # 80, HAGERSTOWN, MD, ..., Hagerstown, MD 21742
$429,000

2 beds

|

3 baths

|

2,739 sq ft

13430 MARQUISE DR # 80, HAGERSTOWN, MD, ...
Community: Emerald Pointe
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
Heritage Hunt 13963 CHELMSFORD DR, GAINESVILLE, VA, 20..., Gainesville, VA 20155
$630,000

3 beds

|

3 baths

|

2,090 sq ft

13963 CHELMSFORD DR, GAINESVILLE, VA, 20...
Community: Heritage Hunt
Gatherings at Wellington 10273 FOUNTAIN CIR 202, MANASSAS, VA, 20..., Manassas, VA 20110
$415,000

3 beds

|

2 baths

|

2,006 sq ft

|

Condo

10273 FOUNTAIN CIR 202, MANASSAS, VA, 20...
Want to learn more about 55+ communities in Winchester Area? 55places can help!
Questions? Call us: (540) 452-4199
Potomac Green 20742 ADAMS MILL PL, ASHBURN, VA, 20147, Ashburn, VA 20147
$800,000

3 beds

|

2 baths

|

1,670 sq ft

20742 ADAMS MILL PL, ASHBURN, VA, 20147
Community: Potomac Green
New Trilogy® at Lake Frederick 103 PLANETREE CT, LAKE FREDERICK, VA, 22..., Lake Frederick, VA 22630
$825,000

3 beds

|

3 baths

|

3,589 sq ft

103 PLANETREE CT, LAKE FREDERICK, VA, 22...
Four Seasons at Ashburn Village 44485 CHAMBERLAIN TER UNIT 200, ASHBURN,..., Ashburn, VA 20147
$450,000

2 beds

|

2 baths

|

1,763 sq ft

|

Condo

44485 CHAMBERLAIN TER UNIT 200, ASHBURN,...
Regency at Dominion Valley 15428 CHAMPIONSHIP DR, HAYMARKET, VA, 20..., Haymarket, VA 20169
$750,000

3 beds

|

3 baths

|

3,309 sq ft

15428 CHAMPIONSHIP DR, HAYMARKET, VA, 20...
Regency at Dominion Valley 5484 RODRIQUEZ LN, HAYMARKET, VA, 20169, Haymarket, VA 20169
$745,000

3 beds

|

3 baths

|

2,598 sq ft

5484 RODRIQUEZ LN, HAYMARKET, VA, 20169
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.
Potomac Green 44420 SUNSET MAPLE DR, ASHBURN, VA, 2014..., Ashburn, VA 20147
$749,000

3 beds

|

3 baths

|

2,447 sq ft

44420 SUNSET MAPLE DR, ASHBURN, VA, 2014...
Community: Potomac Green
New Birchwood at Brambleton 23606 HAVELOCK WALK TER, ASHBURN, VA, 20..., Ashburn, VA 20148
$585,000

3 beds

|

3 baths

|

2,592 sq ft

|

Condo

23606 HAVELOCK WALK TER, ASHBURN, VA, 20...
Regency at Ashburn 44557 GRANITE RUN TER, ASHBURN, VA, 2014..., Ashburn, VA 20147
$845,000

3 beds

|

3 baths

|

4,208 sq ft

44557 GRANITE RUN TER, ASHBURN, VA, 2014...
Community: Regency at Ashburn
Regency at Dominion Valley 15691 ALDERBROOK DR, HAYMARKET, VA, 2016..., Haymarket, VA 20169
$849,900

2 beds

|

3 baths

|

4,124 sq ft

15691 ALDERBROOK DR, HAYMARKET, VA, 2016...
Lansdowne Woods of Virginia 19385 CYPRESS RIDGE TER UNIT 907, LEESBU..., Leesburg, VA 20176
$285,000

1 beds

|

1 baths

|

874 sq ft

|

Condo

19385 CYPRESS RIDGE TER UNIT 907, LEESBU...
Want to learn more about 55+ communities in Winchester Area? 55places can help!
Questions? Call us: (540) 452-4199
Lansdowne Woods of Virginia 19375 CYPRESS RIDGE TER 601, LEESBURG, V..., Leesburg, VA 20176
$529,900

3 beds

|

2 baths

|

1,534 sq ft

|

Condo

19375 CYPRESS RIDGE TER 601, LEESBURG, V...
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...
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
Regency at Dominion Valley 15100 HEATHER MILL LN APT 407, HAYMARKET..., Haymarket, VA 20169
$450,000

2 beds

|

2 baths

|

1,538 sq ft

|

Condo

15100 HEATHER MILL LN APT 407, HAYMARKET...
Birchwood at Brambleton 23630 HAVELOCK WALK TER UNIT 405, ASHBUR..., Ashburn, VA 20148
$445,000

2 beds

|

2 baths

|

1,059 sq ft

|

Condo

23630 HAVELOCK WALK TER UNIT 405, ASHBUR...
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 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...
New Regency at Dominion Valley 15110 HEATHER MILL LN APT 201, HAYMARKET..., Haymarket, VA 20169
$469,000

2 beds

|

2 baths

|

1,551 sq ft

|

Condo

15110 HEATHER MILL LN APT 201, HAYMARKET...
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...
Lexington Square 44486 LOWESTOFT SQ, ASHBURN, VA, 20147, Ashburn, VA 20147
$827,046

3 beds

|

3 baths

|

3,128 sq ft

44486 LOWESTOFT SQ, ASHBURN, VA, 20147
Community: Lexington Square
Lexington 7 44486 LOWESTOFT SQ, ASHBURN, VA, 20147, Ashburn, VA 20147
$827,046

3 beds

|

3 baths

|

3,128 sq ft

44486 LOWESTOFT SQ, ASHBURN, VA, 20147
Community: Lexington 7
Want to learn more about 55+ communities in Winchester Area? 55places can help!
Questions? Call us: (540) 452-4199
Trilogy® at Lake Frederick 108 BUNTING CT, LAKE FREDERICK, VA, 2263..., Lake Frederick, VA 22630
$745,000

3 beds

|

4 baths

|

5,284 sq ft

108 BUNTING CT, LAKE FREDERICK, VA, 2263...
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
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
Regency at Dominion Valley 5411 TREVINO DR, HAYMARKET, VA, 20169, Haymarket, VA 20169
$725,000

3 beds

|

3 baths

|

2,672 sq ft

5411 TREVINO DR, HAYMARKET, VA, 20169
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



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46 communities near Winchester Area
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