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

52 communities near Winchester Area

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5 rating (31 reviews) Lansdowne Woods of Virgin...
$200ks - $500ks
Lansdowne Woods of Virgin..., Lansdowne, VA
Resale Only | 55+ age-restricted | Built 1998 - 2017 | 1,200 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
The Flats at Heathcote Vi...
$300ks - $500ks
The Flats at Heathcote Vi..., Haymarket, VA
New Construction | 55+ age-restricted | Built 2026 - present | 500 homes
5 rating (3 reviews) Heritage Hunt
$400ks - $600ks
Heritage Hunt, Gainesville, VA
Resale Only | 55+ age-restricted | Built 1998 - 2009 | 1,863 homes
2 rating (1 review) Birchwood at Brambleton
$400ks - $1Ms
Birchwood at Brambleton, Ashburn, VA
New and Resale | 55+ age-restricted | Built 2016 - present | 1,502 homes
Want to learn more about 55+ communities in Winchester Area? 55places can help!
Questions? Call us: (540) 452-4199
5 rating (1 review) Regency at Dominion Valle...
$300ks - $1Ms
Regency at Dominion Valle..., Haymarket, VA
Resale Only | 55+ age-restricted | Built 2001 - 2017 | 855 homes
Hiatt Pointe at Snowden B...
$300ks - $600ks
Hiatt Pointe at Snowden B..., Winchester, VA
New Construction | 55+ age-restricted | Built 2024 - present | 740 homes
5 rating (1 review) Crestwood Village
$200ks - $500ks
Crestwood Village, Frederick, MD
Resale Only | 55+ age-restricted | Built 1979 - 1999 | 550 homes
5 rating (2 reviews) Potomac Green
$400ks - $800ks
Potomac Green, Ashburn, VA
Resale Only | 55+ age-restricted | Built 2005 - 2016 | 1,400 homes
The Woodlands of Urbana
$500ks - $700ks
The Woodlands of Urbana, Urbana, MD
Resale Only | 55+ age-restricted | Built 2019 - 2025 | 565 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.
Emerald Pointe
$300ks - $500ks
Emerald Pointe, Hagerstown, MD
New and Resale | 55+ age-restricted | Built 2008 - present | 250 homes
Bloomfields 55+
$700ks - $800ks
Bloomfields 55+, Frederick, MD
New Construction | 55+ age-restricted | Built 2026 - present
Willow Run
$500ks - $600ks
Willow Run, Winchester, VA
New Construction | 55+ age-restricted | 300 homes
5 rating (1 review) Willow Lawn Cottages
$300ks
Willow Lawn Cottages, Winchester, VA
Resale Only | 55+ age-restricted | Built 1999 - 2004 | 120 homes
Rosehill Manor Villas
$300ks
Rosehill Manor Villas, Hagerstown, MD
New Construction | 55+ age-restricted | Built 2022 - present | 177 homes
3 rating (2 reviews) Dunbarton
$300ks - $500ks
Dunbarton, Bristow, VA
Resale Only | 55+ age-restricted | Built 2000 - 2009 | 479 homes
Want to learn more about 55+ communities in Winchester Area? 55places can help!
Questions? Call us: (540) 452-4199
Regency at Belmont
$600ks - $900ks
Regency at Belmont, Ashburn, VA
New Construction | 55+ age-restricted | Built 2021 - present | 145 homes
5 rating (1 review) Gatherings at Wellington
$300ks - $400ks
Gatherings at Wellington, Manassas, VA
Resale Only | 55+ age-restricted | Built 2011 - 2016 | 135 homes
Woodbrook Village
$200ks - $300ks
Woodbrook Village, Winchester, VA
Resale Only | 55+ age-restricted | Built 1999 - 2001 | 81 homes
Cedar Meadows
$300ks - $400ks
Cedar Meadows, White Post, VA
Resale Only | 55+ age-restricted | Built 2010 - 2022 | 129 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.
Central Parke at Lowes Is...
$300ks - $600ks
Central Parke at Lowes Is..., Sterling, VA
Resale Only | 55+ age-restricted | Built 2003 - 2005 | 181 homes
Liberty Grove
$200ks - $300ks
Liberty Grove, Manassas, VA
Resale Only | 55+ age-restricted | Built 2005 - 2005 | 61 homes
3.7 rating (3 reviews) Four Seasons at Ashburn V...
$300ks - $400ks
Four Seasons at Ashburn V..., Ashburn, VA
Resale Only | 55+ age-restricted | Built 2005 - 2005 | 80 homes
Vistas at Lansdowne
$800ks
Vistas at Lansdowne, Lansdowne, VA
Resale Only | 55+ age-restricted | Built 2015 - 2020 | 120 homes
Suffield Meadows
$400ks
Suffield Meadows, Warrenton, VA
Resale Only | 55+ age-restricted | Built 2005 - 2011 | 112 homes
Heritage Highlands
$300ks - $400ks
Heritage Highlands, Lovettsville, VA
Resale Only | 55+ age-restricted | Built 2017 - 2020 | 80 homes
Winchester Landing
$300ks - $400ks
Winchester Landing, Winchester, VA
Resale Only | 55+ age-restricted | Built 2023 - 2025
Want to learn more about 55+ communities in Winchester Area? 55places can help!
Questions? Call us: (540) 452-4199
The Village at Foxfield
$300ks - $500ks
The Village at Foxfield, Middletown, MD
Resale Only | 55+ age-restricted | Built 2003 - 2012 | 81 homes
Abrams Chase
$400ks - $500ks
Abrams Chase, Winchester, VA
New Construction | 55+ age-restricted | Built 2020 - present | 13 homes
Albert Courts
$100ks - $200ks
Albert Courts, Thurmont, MD
Resale Only | 55+ age-restricted | Built 1991 - 2001 | 100 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
$300ks - $800ks
Regency at Ashburn, Ashburn, VA
Resale Only | 55+ age-restricted | Built 2013 - 2020 | 268 homes
Cross Creek Village
$300ks
Cross Creek Village, Winchester, VA
Resale Only | 55+ age-restricted | Built 2001 - 2004 | 90 homes
The Highlands at Blue Rid...
$400ks - $600ks
The Highlands at Blue Rid..., Front Royal, VA
Resale Only | 55+ age-restricted | Built 2017 - 2019 | 42 homes
Gatherings at Potomac Sta...
$400ks - $500ks
Gatherings at Potomac Sta..., Leesburg, VA
New Construction | 55+ age-restricted | Built 2023 - 2024 | 55 homes
Cadence at Lansdowne
$600ks
Cadence at Lansdowne, Lansdowne, VA
Resale Only | 55+ age-restricted | Built 2020 - 2024 | 74 homes
Boxwood Villas
$500ks - $600ks
Boxwood Villas, Urbana, MD
Resale Only | 55+ age-restricted | Built 2019 - 2021 | 92 homes
The Village at Harvest Ri...
$400ks - $500ks
The Village at Harvest Ri..., Winchester, VA
Resale Only | 55+ age-restricted | Built 2005 - 2016 | 82 homes
Lexington 7
$600ks - $700ks
Lexington 7, Ashburn, VA
Resale Only | 55+ age-restricted | Built 2017 - 2020 | 113 homes
Want to learn more about 55+ communities in Winchester Area? 55places can help!
Questions? Call us: (540) 452-4199
The Retreat at Poland Hil...
$800ks
The Retreat at Poland Hil..., Chantilly, VA
Resale Only | 55+ age-restricted | Built 2020 - 2022 | 219 homes
CobbleStone Estates
$400ks - $500ks
CobbleStone Estates, Hagerstown, MD
New and Resale | 55+ age-restricted | Built 2015 - present | 66 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...2
Trilogy® at Lake Frederick 109 EMPEROR DR, LAKE FREDERICK, VA, 2263..., Lake Frederick, VA 22630
$559,900

4 beds

|

4 baths

|

3,859 sq ft

109 EMPEROR DR, LAKE FREDERICK, VA, 2263...
New Dunbarton 13242 ORMOND DR, BRISTOW, VA, 20136, Bristow, VA 20136
$540,000

2 beds

|

2 baths

|

1,763 sq ft

13242 ORMOND DR, BRISTOW, VA, 20136
Community: Dunbarton
New Heritage Hunt 13733 CURRANT LOOP, GAINESVILLE, VA, 201..., Gainesville, VA 20155
$725,000

3 beds

|

4 baths

|

3,535 sq ft

13733 CURRANT LOOP, GAINESVILLE, VA, 201...
Community: Heritage Hunt
New Dunbarton 12000 RUTHERGLEN PL, BRISTOW, VA, 20136, Bristow, VA 20136
$745,000

4 beds

|

3 baths

|

3,281 sq ft

12000 RUTHERGLEN PL, BRISTOW, VA, 20136
Community: Dunbarton
New Trilogy® at Lake Frederick 114 TURNSTONE LN, LAKE FREDERICK, VA, 22..., Lake Frederick, VA 22630
$620,000

3 beds

|

4 baths

|

3,333 sq ft

114 TURNSTONE LN, LAKE FREDERICK, VA, 22...
Want to learn more about 55+ communities in Winchester Area? 55places can help!
Questions? Call us: (540) 452-4199
New Hiatt Pointe at Snowden Bridge 408 GRANITE RIDGE DR, WINCHESTER, VA, 22..., Winchester, VA 22603
$349,990

3 beds

|

3 baths

|

1,752 sq ft

408 GRANITE RIDGE DR, WINCHESTER, VA, 22...
New Trilogy® at Lake Frederick 137 HORNBEAM DR, LAKE FREDERICK, VA, 226..., Lake Frederick, VA 22630
$415,000

3 beds

|

4 baths

|

2,310 sq ft

137 HORNBEAM DR, LAKE FREDERICK, VA, 226...
New Willow Lawn Cottages 1868 ROSSER LN, WINCHESTER, VA, 22601, Winchester, VA 22601
$370,000

2 beds

|

2 baths

|

1,090 sq ft

1868 ROSSER LN, WINCHESTER, VA, 22601
New Heritage Hunt 6324 ADIRONDACK CT, GAINESVILLE, VA, 201..., Gainesville, VA 20155
$659,900

3 beds

|

2 baths

|

1,932 sq ft

6324 ADIRONDACK CT, GAINESVILLE, VA, 201...
Community: Heritage Hunt
New Heritage Highlands 85 HARPERS MILL WAY, LOVETTSVILLE, VA, 2..., Lovettsville, VA 20180
$517,800

2 beds

|

3 baths

|

2,119 sq ft

85 HARPERS MILL WAY, LOVETTSVILLE, VA, 2...
Community: Heritage Highlands
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.
New The Village at Foxfield 7 DERR LN, MIDDLETOWN, MD, 21769, Middletown, MD 21769
$569,900

3 beds

|

3 baths

|

2,208 sq ft

7 DERR LN, MIDDLETOWN, MD, 21769
New
Cindy Certified
18815 FORSYTH CT, HAGERSTOWN, MD, 21740, Hagerstown, MD 21740
$366,500

4 beds

|

2 baths

|

2,065 sq ft

18815 FORSYTH CT, HAGERSTOWN, MD, 21740
Regency at Dominion Valley 15120 HEATHER MILL LN 401, HAYMARKET, VA..., Haymarket, VA 20169
$529,000

3 beds

|

2 baths

|

1,800 sq ft

|

Condo

15120 HEATHER MILL LN 401, HAYMARKET, VA...
Potomac Green 44397 MALTESE FALCON SQ, ASHBURN, VA, 20..., Ashburn, VA 20147
$749,999

3 beds

|

3 baths

|

2,335 sq ft

44397 MALTESE FALCON SQ, ASHBURN, VA, 20...
Community: Potomac Green
Regency at Dominion Valley 15221 ROYAL CREST DR 205, HAYMARKET, VA,..., Haymarket, VA 20169
$450,000

2 beds

|

2 baths

|

1,538 sq ft

|

Condo

15221 ROYAL CREST DR 205, HAYMARKET, VA,...
Lansdowne Woods of Virginia 19385 CYPRESS RIDGE TER 107, LEESBURG, V..., Leesburg, VA 20176
$298,000

1 beds

|

1 baths

|

874 sq ft

|

Condo

19385 CYPRESS RIDGE TER 107, LEESBURG, V...
Want to learn more about 55+ communities in Winchester Area? 55places can help!
Questions? Call us: (540) 452-4199
Crestwood Village 7049 CATALPA RD, FREDERICK, MD, 21703, Frederick, MD 21703
$394,900

2 beds

|

2 baths

|

1,324 sq ft

7049 CATALPA RD, FREDERICK, MD, 21703
Community: Crestwood Village
The Village at Harvest Ridge 150 HARVEST RIDGE DR, WINCHESTER, VA, 22..., Winchester, VA 22601
$689,900

4 beds

|

3 baths

|

4,385 sq ft

150 HARVEST RIDGE DR, WINCHESTER, VA, 22...
Trilogy® at Lake Frederick 112 KINGFISHER CT, LAKE FREDERICK, VA, 2..., Lake Frederick, VA 22630
$874,990

3 beds

|

4 baths

|

4,211 sq ft

112 KINGFISHER CT, LAKE FREDERICK, VA, 2...
Regency at Ashburn 20934 SABER JET PL, ASHBURN, VA, 20147, Ashburn, VA 20147
$874,000

3 beds

|

3 baths

|

2,798 sq ft

20934 SABER JET PL, ASHBURN, VA, 20147
Community: Regency at Ashburn
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 7065 HERITAGE HUNT DR 110, GAINESVILLE, ..., Gainesville, VA 20155
$415,000

3 beds

|

2 baths

|

1,424 sq ft

|

Condo

7065 HERITAGE HUNT DR 110, GAINESVILLE, ...
Community: Heritage Hunt
Woodbrook Village 305 KNOLLWOOD CT, WINCHESTER, VA, 22602, Winchester, VA 22602
$359,000

2 beds

|

2 baths

|

1,270 sq ft

305 KNOLLWOOD CT, WINCHESTER, VA, 22602
Community: Woodbrook Village
Winchester Landing 118 HARDY WAY, WINCHESTER, VA, 22602, Winchester, VA 22602
$369,900

3 beds

|

3 baths

|

1,630 sq ft

118 HARDY WAY, WINCHESTER, VA, 22602
Community: Winchester Landing
Trilogy® at Lake Frederick 127 HUCKLEBERRY CT, LAKE FREDERICK, VA, ..., Lake Frederick, VA 22630
$799,990

3 beds

|

3 baths

|

3,434 sq ft

127 HUCKLEBERRY CT, LAKE FREDERICK, VA, ...
Regency at Dominion Valley 15100 HEATHER MILL LN 403, HAYMARKET, VA..., Haymarket, VA 20169
$450,000

2 beds

|

2 baths

|

1,499 sq ft

|

Condo

15100 HEATHER MILL LN 403, HAYMARKET, VA...
Heritage Hunt 6934 WALNUT HILL DR, GAINESVILLE, VA, 20..., Gainesville, VA 20155
$619,000

3 beds

|

3 baths

|

2,081 sq ft

6934 WALNUT HILL DR, GAINESVILLE, VA, 20...
Community: Heritage Hunt
Potomac Green 44401 WEDGEFORD WAY, ASHBURN, VA, 20147, Ashburn, VA 20147
$789,000

3 beds

|

3 baths

|

2,447 sq ft

44401 WEDGEFORD WAY, ASHBURN, VA, 20147
Community: Potomac Green
Want to learn more about 55+ communities in Winchester Area? 55places can help!
Questions? Call us: (540) 452-4199
Abrams Chase 117 AMBERFIELD CT, WINCHESTER, VA, 22602, Winchester, VA 22602
$479,000

3 beds

|

2 baths

|

1,784 sq ft

117 AMBERFIELD CT, WINCHESTER, VA, 22602
Community: Abrams Chase
Lansdowne Woods of Virginia 19355 CYPRESS RIDGE TER 802, LEESBURG, V..., Leesburg, VA 20176
$479,000

3 beds

|

2 baths

|

1,560 sq ft

|

Condo

19355 CYPRESS RIDGE TER 802, LEESBURG, V...
Rosehill Manor Villas HOMESITE 12 OLEANDER CT, HAGERSTOWN, MD,..., Hagerstown, MD 21742
$445,799

3 beds

|

2 baths

|

1,687 sq ft

HOMESITE 12 OLEANDER CT, HAGERSTOWN, MD,...
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 19355 CYPRESS RIDGE TER 307, LEESBURG, V..., Leesburg, VA 20176
$449,900

2 beds

|

2 baths

|

1,315 sq ft

|

Condo

19355 CYPRESS RIDGE TER 307, LEESBURG, V...
Potomac Green 20600 HOPE SPRING TER 207, ASHBURN, VA, ..., Ashburn, VA 20147
$525,000

2 beds

|

2 baths

|

1,632 sq ft

|

Condo

20600 HOPE SPRING TER 207, ASHBURN, VA, ...
Community: Potomac Green
Trilogy® at Lake Frederick 113 PINTAIL WAY, LAKE FREDERICK, VA, 226..., Lake Frederick, VA 22630
$799,000

3 beds

|

4 baths

|

4,159 sq ft

113 PINTAIL WAY, LAKE FREDERICK, VA, 226...
Heritage Hunt 13948 REAL QUITE CT, GAINESVILLE, VA, 20..., Gainesville, VA 20155
$745,000

3 beds

|

3 baths

|

2,520 sq ft

13948 REAL QUITE CT, GAINESVILLE, VA, 20...
Community: Heritage Hunt
Hiatt Pointe at Snowden Bridge 108 OLEANDER CT, WINCHESTER, VA, 22603, Winchester, VA 22603
$509,990

3 beds

|

3 baths

|

2,264 sq ft

108 OLEANDER CT, WINCHESTER, VA, 22603
Lansdowne Woods of Virginia 19385 CYPRESS RIDGE TER 1016, LEESBURG, ..., Leesburg, VA 20176
$400,000

2 beds

|

2 baths

|

1,196 sq ft

|

Condo

19385 CYPRESS RIDGE TER 1016, LEESBURG, ...
Lansdowne Woods of Virginia 19355 CYPRESS RIDGE TER 219, LEESBURG, V..., Leesburg, VA 20176
$455,000

2 beds

|

2 baths

|

1,500 sq ft

|

Condo

19355 CYPRESS RIDGE TER 219, LEESBURG, V...
Crestwood Village 109 APPLE CREEK RD, FREDERICK, MD, 21702, Frederick, MD 21702
$435,000

3 beds

|

2 baths

|

1,680 sq ft

109 APPLE CREEK RD, FREDERICK, MD, 21702
Community: Crestwood Village
Want to learn more about 55+ communities in Winchester Area? 55places can help!
Questions? Call us: (540) 452-4199
Rosehill Manor Villas HOMESITE 3.75 SNAPDRAGON WAY, HAGERSTOWN..., Hagerstown, MD 21742
$405,096

2 beds

|

2 baths

|

1,723 sq ft

HOMESITE 3.75 SNAPDRAGON WAY, HAGERSTOWN...
Birchwood at Brambleton 23677 JAYADEV TER, ASHBURN, VA, 20148, Ashburn, VA 20148
$1,000,000

3 beds

|

4 baths

|

4,152 sq ft

23677 JAYADEV TER, ASHBURN, VA, 20148
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.



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REIN updates its listings on a daily basis. Data last updated: Nov 10, 2026.
This application does not include information on all of the properties available for sale at this time.

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