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

155 homes 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
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 - $400Ks
Cross Creek Village, Winchester, VA
Resale Only | 55+ age-restricted | Built 2001 - 2004 | 90 homes
No reviews yet 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
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
$600Ks - $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 - $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 - $800Ks
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
$600Ks - $700Ks
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
No reviews yet 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
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 - $600Ks
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 - $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
No reviews yet 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
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 - $800Ks
Lexington 7, Ashburn, VA
Resale Only | 55+ age-restricted | Built 2017 - 2020 | 113 homes
No reviews yet 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.
No reviews yet JerMae Estates
$400Ks - $500Ks
JerMae Estates, Thurmont, MD
Resale Only | 55+ age-restricted | Built 2003 - 2008 | 108 homes
No reviews yet 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
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 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
No reviews yet CobbleStone Estates
$400Ks - $500Ks
CobbleStone Estates, Hagerstown, MD
New and Resale | 55+ age-restricted | Built 2015 - present | 66 homes
1...2
Potomac Green 44397 ADARE MANOR SQ, ASHBURN, VA, 20147, Ashburn, VA 20147
$718,000

3 beds

|

3 baths

|

2,253 sq ft

44397 ADARE MANOR SQ, ASHBURN, VA, 20147
Community: Potomac Green
Regency at Dominion Valley 15251 ROYAL CREST DR APT 306, HAYMARKET,..., Haymarket, VA 20169
$550,000

3 beds

|

2 baths

|

1,833 sq ft

|

Condo

15251 ROYAL CREST DR APT 306, HAYMARKET,...
Gatherings at Wellington 9202 CHARLESTON DR 405, MANASSAS, VA, 20..., Manassas, VA 20110
$365,000

2 beds

|

2 baths

|

1,504 sq ft

|

Condo

9202 CHARLESTON DR 405, MANASSAS, VA, 20...
Heritage Hunt 13753 TUSCARORA CT, GAINESVILLE, VA, 201..., Gainesville, VA 20155
$750,000

3 beds

|

3 baths

|

3,338 sq ft

13753 TUSCARORA CT, GAINESVILLE, VA, 201...
Community: Heritage Hunt
Lansdowne Woods of Virginia 19385 CYPRESS RIDGE TER UNIT 522, LEESBU..., Leesburg, VA 20176
$390,000

2 beds

|

2 baths

|

1,101 sq ft

|

Condo

19385 CYPRESS RIDGE TER UNIT 522, LEESBU...
Want to learn more about 55+ communities in Winchester Area? 55places can help!
Questions? Call us: (540) 452-4199
Birchwood at Brambleton 23631 HAVELOCK WALK TER 318, ASHBURN, VA..., Ashburn, VA 20148
$529,900

2 beds

|

2 baths

|

1,967 sq ft

|

Condo

23631 HAVELOCK WALK TER 318, ASHBURN, VA...
Regency at Dominion Valley 15201 ROYAL CREST DR APT 407, HAYMARKET,..., Haymarket, VA 20169
$450,000

2 beds

|

2 baths

|

1,538 sq ft

|

Condo

15201 ROYAL CREST DR APT 407, HAYMARKET,...
Trilogy® at Lake Frederick 116 COTTONTAIL DR, LAKE FREDERICK, VA, 2..., Lake Frederick, VA 22630
$685,000

3 beds

|

3 baths

|

2,885 sq ft

116 COTTONTAIL DR, LAKE FREDERICK, VA, 2...
Central Parke at Lowes Island 20745 ROYAL PALACE SQ UNIT 207, STERLING..., Sterling, VA 20165
$429,900

2 beds

|

2 baths

|

1,692 sq ft

|

Condo

20745 ROYAL PALACE SQ UNIT 207, STERLING...
Heritage Hunt 6524 BOX ELDER LOOP, GAINESVILLE, VA, 20..., Gainesville, VA 20155
$610,000

3 beds

|

3 baths

|

2,153 sq ft

6524 BOX ELDER LOOP, GAINESVILLE, VA, 20...
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.
Suffield Meadows 6696 CLUB HOUSE LN UNIT 104, WARRENTON, ..., Warrenton, VA 20187
$440,000

3 beds

|

2 baths

|

1,994 sq ft

|

Condo

6696 CLUB HOUSE LN UNIT 104, WARRENTON, ...
Community: Suffield Meadows
Willow Lawn Cottages 1823 KERSHAW LN, WINCHESTER, VA, 22601, Winchester, VA 22601
$389,900

2 beds

|

2 baths

|

1,591 sq ft

1823 KERSHAW LN, WINCHESTER, VA, 22601
New Birchwood at Brambleton 23640 BOLTON CRESCENT TER # 13-204, ASHB..., Ashburn, VA 20148
$499,990

2 beds

|

2 baths

|

1,431 sq ft

|

Condo

23640 BOLTON CRESCENT TER # 13-204, ASHB...
Birchwood at Brambleton 42874 FIREFLY SONATA TER APT 206, ASHBUR..., Ashburn, VA 20148
$615,000

3 beds

|

2 baths

|

1,850 sq ft

|

Condo

42874 FIREFLY SONATA TER APT 206, ASHBUR...
Central Parke at Lowes Island 20745 ROYAL PALACE SQ 210, STERLING, VA,..., Sterling, VA 20165
$488,000

3 beds

|

2 baths

|

1,989 sq ft

|

Condo

20745 ROYAL PALACE SQ 210, STERLING, VA,...
Want to learn more about 55+ communities in Winchester Area? 55places can help!
Questions? Call us: (540) 452-4199
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...
Trilogy® at Lake Frederick 118 VICEROY WAY, LAKE FREDERICK, VA, 226..., Lake Frederick, VA 22630
$650,000

3 beds

|

3 baths

|

2,523 sq ft

118 VICEROY WAY, LAKE FREDERICK, VA, 226...
Gatherings at Wellington 9204 CHARLESTON DR UNIT 404, MANASSAS, V..., Manassas, VA 20110
$379,000

2 beds

|

2 baths

|

1,504 sq ft

|

Condo

9204 CHARLESTON DR UNIT 404, MANASSAS, V...
Lansdowne Woods of Virginia 19375 CYPRESS RIDGE TER UNIT 418, LEESBU..., Leesburg, VA 20176
$499,900

2 beds

|

2 baths

|

1,441 sq ft

|

Condo

19375 CYPRESS RIDGE TER UNIT 418, LEESBU...
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...
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.
Birchwood at Brambleton 43016 DEBONAIR TER, ASHBURN, VA, 20148, Ashburn, VA 20148
$880,862

3 beds

|

4 baths

|

2,742 sq ft

43016 DEBONAIR TER, ASHBURN, VA, 20148
Gatherings at Wellington 10273 FOUNTAIN CIR 306, MANASSAS, VA, 20..., Manassas, VA 20110
$390,000

2 beds

|

2 baths

|

1,558 sq ft

|

Condo

10273 FOUNTAIN CIR 306, MANASSAS, VA, 20...
Birchwood at Brambleton 43257 GREELEY SQ, ASHBURN, VA, 20148, Ashburn, VA 20148
$999,900

3 beds

|

4 baths

|

4,338 sq ft

43257 GREELEY SQ, ASHBURN, VA, 20148
Heritage Hunt 17680 GLASS RIDGE PL, GAINESVILLE, VA, 2..., Gainesville, VA 20155
$675,000

3 beds

|

3 baths

|

2,920 sq ft

17680 GLASS RIDGE PL, GAINESVILLE, VA, 2...
Community: Heritage Hunt
Lansdowne Woods of Virginia 19355 CYPRESS RIDGE TER 423, LEESBURG, V..., Leesburg, VA 20176
$399,900

2 beds

|

2 baths

|

1,315 sq ft

|

Condo

19355 CYPRESS RIDGE TER 423, LEESBURG, V...
Want to learn more about 55+ communities in Winchester Area? 55places can help!
Questions? Call us: (540) 452-4199
Regency at Creekside 5966 BOWES CREEK PL, GAINESVILLE, VA, 20..., Gainesville, VA 20155
$1,320,000

4 beds

|

5 baths

|

5,614 sq ft

5966 BOWES CREEK PL, GAINESVILLE, VA, 20...
Potomac Green 20763 CRESCENT POINTE PL, ASHBURN, VA, 2..., Ashburn, VA 20147
$879,900

3 beds

|

3 baths

|

2,810 sq ft

20763 CRESCENT POINTE PL, ASHBURN, VA, 2...
Community: Potomac Green
Birchwood at Brambleton 23631 HAVELOCK WALK TER 313, ASHBURN, VA..., Ashburn, VA 20148
$485,000

2 beds

|

2 baths

|

1,403 sq ft

|

Condo

23631 HAVELOCK WALK TER 313, ASHBURN, VA...
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
The Village at Harvest Ridge 150 HARVEST RIDGE DR, WINCHESTER, VA, 22..., Winchester, VA 22601
$655,000

4 beds

|

3 baths

|

4,385 sq ft

150 HARVEST RIDGE DR, WINCHESTER, VA, 22...
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 118 MILKWEED DR, LAKE FREDERICK, VA, 226..., Lake Frederick, VA 22630
$484,900

2 beds

|

2 baths

|

1,632 sq ft

118 MILKWEED DR, LAKE FREDERICK, VA, 226...
Birchwood at Brambleton 43011 DEBONAIR TER, ASHBURN, VA, 20148, Ashburn, VA 20148
$881,202

3 beds

|

4 baths

|

2,742 sq ft

43011 DEBONAIR TER, ASHBURN, VA, 20148
Regency at Dominion Valley 15236 WEISKOPF CT, HAYMARKET, VA, 20169, Haymarket, VA 20169
$887,000

2 beds

|

3 baths

|

3,994 sq ft

15236 WEISKOPF CT, HAYMARKET, VA, 20169
Birchwood at Brambleton 42972 TRUMAN TER, ASHBURN, VA, 20148, Ashburn, VA 20148
$853,586

4 beds

|

4 baths

|

2,742 sq ft

42972 TRUMAN TER, ASHBURN, VA, 20148
Central Parke at Lowes Island 20898 PRINCE LOWES TER, STERLING, VA, 20..., Sterling, VA 20165
$750,000

3 beds

|

4 baths

|

3,239 sq ft

20898 PRINCE LOWES TER, STERLING, VA, 20...
Want to learn more about 55+ communities in Winchester Area? 55places can help!
Questions? Call us: (540) 452-4199
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...
Potomac Green 20759 CRESCENT POINTE PL, ASHBURN, VA, 2..., Ashburn, VA 20147
$865,000

3 beds

|

4 baths

|

2,973 sq ft

20759 CRESCENT POINTE PL, ASHBURN, VA, 2...
Community: Potomac Green
Birchwood at Brambleton 42874 FIREFLY SONATA TER APT 107, ASHBUR..., Ashburn, VA 20148
$465,000

2 beds

|

2 baths

|

1,268 sq ft

|

Condo

42874 FIREFLY SONATA TER APT 107, ASHBUR...
Heritage Hunt 6824 DERBY RUN WAY, GAINESVILLE, VA, 201..., Gainesville, VA 20155
$775,000

3 beds

|

3 baths

|

3,774 sq ft

6824 DERBY RUN WAY, GAINESVILLE, VA, 201...
Community: Heritage Hunt
Birchwood at Brambleton 42920 FIREFLY SONATA TER UNIT 307, ASHBU..., Ashburn, VA 20148
$590,000

3 beds

|

2 baths

|

1,630 sq ft

|

Condo

42920 FIREFLY SONATA TER UNIT 307, ASHBU...



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155 homes near Winchester Area
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REIN updates its listings on a daily basis. Data last updated: Oct 23, 2025.
This application does not include information on all of the properties available for sale at this time.

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