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

51 communities 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
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 (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 (3 reviews) Heritage Hunt
$400ks - $600ks
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
Want to learn more about 55+ communities in Winchester Area? 55places can help!
Questions? Call us: (540) 452-4199
The Woodlands of Urbana
$500ks - $700ks
The Woodlands of Urbana, Urbana, MD
Resale Only | 55+ age-restricted | Built 2019 - 2025 | 565 homes
5 rating (1 reviews) Regency at Dominion Valle...
$300ks - $1Ms
Regency at Dominion Valle..., Haymarket, VA
Resale Only | 55+ age-restricted | Built 2001 - 2017 | 855 homes
Rosehill Manor Villas
$300ks
Rosehill Manor Villas, Hagerstown, MD
New Construction | 55+ age-restricted | Built 2022 - present | 177 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
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
3 rating (2 reviews) Dunbarton
$300ks - $500ks
Dunbarton, Bristow, VA
Resale Only | 55+ age-restricted | Built 2000 - 2009 | 479 homes
Montebello
$500ks - $1Ms
Montebello, Sterling, VA
New and Resale | 55+ age-restricted | Built 2022 - present | 450 homes
5 rating (1 reviews) Willow Lawn Cottages
$300ks
Willow Lawn Cottages, Winchester, VA
Resale Only | 55+ age-restricted | Built 1999 - 2004 | 120 homes
Cadence at Lansdowne
$600ks
Cadence at Lansdowne, Lansdowne, VA
Resale Only | 55+ age-restricted | Built 2020 - 2024 | 74 homes
The Village at Freedom Hi...
$300ks
The Village at Freedom Hi..., Hagerstown, MD
New and Resale | 55+ age-restricted | Built 2007 - present | 66 homes
Want to learn more about 55+ communities in Winchester Area? 55places can help!
Questions? Call us: (540) 452-4199
Winchester Landing
$300ks - $400ks
Winchester Landing, Winchester, VA
Resale Only | 55+ age-restricted | Built 2023 - 2025
5 rating (1 reviews) Crestwood Village
$200ks - $500ks
Crestwood Village, Frederick, MD
Resale Only | 55+ age-restricted | Built 1979 - 1999 | 550 homes
Regency at Belmont
$600ks - $900ks
Regency at Belmont, Ashburn, VA
New Construction | 55+ age-restricted | Built 2021 - present | 145 homes
Ballenger Run
$300ks - $400ks
Ballenger Run, Frederick, MD
Resale Only | 55+ age-restricted | Built 2019 - 2020 | 36 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.
The Village at Foxfield
$300ks - $500ks
The Village at Foxfield, Middletown, MD
Resale Only | 55+ age-restricted | Built 2003 - 2012 | 81 homes
5 rating (2 reviews) Potomac Green
$400ks - $800ks
Potomac Green, Ashburn, VA
Resale Only | 55+ age-restricted | Built 2005 - 2016 | 1,400 homes
Suffield Meadows
$400ks
Suffield Meadows, Warrenton, VA
Resale Only | 55+ age-restricted | Built 2005 - 2011 | 112 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
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
Gatherings at Potomac Sta...
$400ks - $500ks
Gatherings at Potomac Sta..., Leesburg, VA
New Construction | 55+ age-restricted | Built 2023 - 2024 | 55 homes
Want to learn more about 55+ communities in Winchester Area? 55places can help!
Questions? Call us: (540) 452-4199
Woodbrook Village
$200ks - $300ks
Woodbrook Village, Winchester, VA
Resale Only | 55+ age-restricted | Built 1999 - 2001 | 81 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
JerMae Estates
$300ks - $400ks
JerMae Estates, Thurmont, MD
Resale Only | 55+ age-restricted | Built 2003 - 2008 | 108 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.
CobbleStone Estates
$400ks - $500ks
CobbleStone Estates, Hagerstown, MD
New and Resale | 55+ age-restricted | Built 2015 - present | 66 homes
Regency at Ashburn
$300ks - $800ks
Regency at Ashburn, Ashburn, VA
Resale Only | 55+ age-restricted | Built 2013 - 2020 | 268 homes
The Villages at Broadland...
$400ks
The Villages at Broadland..., Ashburn, VA
New and Resale | 55+ age-restricted | Built 2013 - present | 78 homes
Vistas at Lansdowne
$800ks
Vistas at Lansdowne, Lansdowne, VA
Resale Only | 55+ age-restricted | Built 2015 - 2020 | 120 homes
Lexington 7
$600ks - $700ks
Lexington 7, Ashburn, VA
Resale Only | 55+ age-restricted | Built 2017 - 2020 | 113 homes
The Signature at Broadlan...
$300ks - $400ks
The Signature at Broadlan..., Ashburn, VA
Resale Only | 55+ age-restricted | Built 2018 - 2020 | 45 homes
The Retreat at Poland Hil...
$800ks
The Retreat at Poland Hil..., Chantilly, VA
Resale Only | 55+ age-restricted | Built 2020 - 2022 | 219 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
Want to learn more about 55+ communities in Winchester Area? 55places can help!
Questions? Call us: (540) 452-4199
Cross Creek Village
$300ks
Cross Creek Village, Winchester, VA
Resale Only | 55+ age-restricted | Built 2001 - 2004 | 90 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.
1...2
Heritage Hunt 7065 HERITAGE HUNT DR 108, GAINESVILLE, ..., Gainesville, VA 20155
$399,900

2 beds

|

2 baths

|

1,292 sq ft

|

Condo

7065 HERITAGE HUNT DR 108, GAINESVILLE, ...
Community: Heritage Hunt
Cedar Meadows 126 FORGET ME NOT DR, WHITE POST, VA, 22..., White Post, VA 22663
$459,900

3 beds

|

2 baths

|

1,659 sq ft

126 FORGET ME NOT DR, WHITE POST, VA, 22...
Community: Cedar Meadows
Trilogy® at Lake Frederick 109 EMPEROR DR, LAKE FREDERICK, VA, 2263..., Lake Frederick, VA 22630
$609,900

4 beds

|

4 baths

|

3,859 sq ft

109 EMPEROR DR, LAKE FREDERICK, VA, 2263...
Abrams Chase 105 AMBERFIELD CT, WINCHESTER, VA, 22602, Winchester, VA 22602
$464,900

2 beds

|

2 baths

|

1,800 sq ft

105 AMBERFIELD CT, WINCHESTER, VA, 22602
Community: Abrams Chase
New Heritage Hunt 6872 SADDLE RUN WAY, GAINESVILLE, VA, 20..., Gainesville, VA 20155
$699,999

2 beds

|

2 baths

|

2,066 sq ft

6872 SADDLE RUN WAY, GAINESVILLE, VA, 20...
Community: Heritage Hunt
Want to learn more about 55+ communities in Winchester Area? 55places can help!
Questions? Call us: (540) 452-4199
New Trilogy® at Lake Frederick 114 TURNSTONE LN, LAKE FREDERICK, VA, 22..., Lake Frederick, VA 22630
$680,000

3 beds

|

4 baths

|

3,333 sq ft

114 TURNSTONE LN, LAKE FREDERICK, VA, 22...
New Woodbrook Village 111 TANGLEWOOD LN, WINCHESTER, VA, 22602, Winchester, VA 22602
$369,900

2 beds

|

2 baths

|

1,400 sq ft

111 TANGLEWOOD LN, WINCHESTER, VA, 22602
Community: Woodbrook Village
New Abrams Chase 131 AMBERFIELD CT, WINCHESTER, VA, 22602, Winchester, VA 22602
$465,000

2 beds

|

2 baths

|

1,811 sq ft

131 AMBERFIELD CT, WINCHESTER, VA, 22602
Community: Abrams Chase
New Regency at Belmont 43931 NORMAN NEWS TER, ASHBURN, VA, 2014..., Ashburn, VA 20147
$1,085,000

3 beds

|

4 baths

|

3,255 sq ft

43931 NORMAN NEWS TER, ASHBURN, VA, 2014...
Community: Regency at Belmont
Regency at Dominion Valley 5368 ANTIOCH RIDGE DR, HAYMARKET, VA, 20..., Haymarket, VA 20169
$875,000

2 beds

|

2 baths

|

2,338 sq ft

5368 ANTIOCH RIDGE DR, HAYMARKET, VA, 20...
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 107, LEESBURG, V..., Leesburg, VA 20176
$330,000

1 beds

|

1 baths

|

874 sq ft

|

Condo

19385 CYPRESS RIDGE TER 107, LEESBURG, V...
Heritage Hunt 13919 CHELMSFORD DR, GAINESVILLE, VA, 20..., Gainesville, VA 20155
$775,000

4 beds

|

4 baths

|

4,779 sq ft

13919 CHELMSFORD DR, GAINESVILLE, VA, 20...
Community: Heritage Hunt
Trilogy® at Lake Frederick 106 FRINGETREE CT, LAKE FREDERICK, VA, 2..., Lake Frederick, VA 22630
$679,999

4 beds

|

3 baths

|

4,047 sq ft

106 FRINGETREE CT, LAKE FREDERICK, VA, 2...
The Village at Foxfield 4 LAMAR LN, MIDDLETOWN, MD, 21769, Middletown, MD 21769
$475,000

2 beds

|

2 baths

|

1,359 sq ft

4 LAMAR LN, MIDDLETOWN, MD, 21769
The Village at Foxfield 7 DERR LN, MIDDLETOWN, MD, 21769, Middletown, MD 21769
$625,000

3 beds

|

3 baths

|

2,208 sq ft

7 DERR LN, MIDDLETOWN, MD, 21769
Trilogy® at Lake Frederick 142 MILKWEED DR, LAKE FREDERICK, VA, 226..., Lake Frederick, VA 22630
$554,900

3 beds

|

2 baths

|

1,769 sq ft

142 MILKWEED DR, LAKE FREDERICK, VA, 226...
Want to learn more about 55+ communities in Winchester Area? 55places can help!
Questions? Call us: (540) 452-4199
The Woodlands of Urbana 3231 THORNAPPLE DR, FREDERICK, MD, 21704, Frederick, MD 21704
$709,000

3 beds

|

3 baths

|

2,612 sq ft

3231 THORNAPPLE DR, FREDERICK, MD, 21704
Regency at Dominion Valley 15110 HEATHER MILL LN 307, HAYMARKET, VA..., Haymarket, VA 20169
$425,000

2 beds

|

2 baths

|

1,538 sq ft

|

Condo

15110 HEATHER MILL LN 307, HAYMARKET, VA...
Crestwood Village 5661 CRABAPPLE DR, FREDERICK, MD, 21703, Frederick, MD 21703
$415,000

2 beds

|

2 baths

|

1,297 sq ft

5661 CRABAPPLE DR, FREDERICK, MD, 21703
Community: Crestwood Village
Birchwood at Brambleton 23631 HAVELOCK WALK TER 203, ASHBURN, VA..., Ashburn, VA 20148
$445,000

2 beds

|

2 baths

|

1,012 sq ft

|

Condo

23631 HAVELOCK WALK TER 203, ASHBURN, 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.
Regency at Dominion Valley 15454 LEGACY WAY, HAYMARKET, VA, 20169, Haymarket, VA 20169
$975,000

2 beds

|

2 baths

|

2,274 sq ft

15454 LEGACY WAY, HAYMARKET, VA, 20169
Trilogy® at Lake Frederick 133 SKIPPER DR, LAKE FREDERICK, VA, 2263..., Lake Frederick, VA 22630
$675,000

3 beds

|

3 baths

|

2,843 sq ft

133 SKIPPER DR, LAKE FREDERICK, VA, 2263...
Trilogy® at Lake Frederick 105 TURNSTONE LN, LAKE FREDERICK, VA, 22..., Lake Frederick, VA 22630
$835,000

4 beds

|

4 baths

|

5,247 sq ft

105 TURNSTONE LN, LAKE FREDERICK, VA, 22...
Suffield Meadows 6727 HOLLY FARM LN, WARRENTON, VA, 20187, Warrenton, VA 20187
$659,000

4 beds

|

3 baths

|

3,066 sq ft

|

Condo

6727 HOLLY FARM LN, WARRENTON, VA, 20187
Community: Suffield Meadows
Lansdowne Woods of Virginia 19355 CYPRESS RIDGE TER 408, LEESBURG, V..., Leesburg, VA 20176
$379,999

2 beds

|

2 baths

|

1,105 sq ft

|

Condo

19355 CYPRESS RIDGE TER 408, LEESBURG, V...
Crestwood Village 5679 BARBERRY CT, FREDERICK, MD, 21703, Frederick, MD 21703
$419,900

2 beds

|

2 baths

|

1,148 sq ft

5679 BARBERRY CT, FREDERICK, MD, 21703
Community: Crestwood Village
Heritage Hunt 13890 CHELMSFORD DR 305, GAINESVILLE, VA..., Gainesville, VA 20155
$425,000

2 beds

|

2 baths

|

1,388 sq ft

|

Condo

13890 CHELMSFORD DR 305, GAINESVILLE, VA...
Community: Heritage Hunt
Want to learn more about 55+ communities in Winchester Area? 55places can help!
Questions? Call us: (540) 452-4199
Montebello 21630 HAWKSBILL HIGH CIR 406, STERLING, ..., Sterling, VA 20164
$734,999

3 beds

|

2 baths

|

1,825 sq ft

|

Condo

21630 HAWKSBILL HIGH CIR 406, STERLING, ...
Community: Montebello
The Woodlands of Urbana 3226 STARLIGHT ST, FREDERICK, MD, 21704, Frederick, MD 21704
$625,000

3 beds

|

4 baths

|

2,226 sq ft

3226 STARLIGHT ST, FREDERICK, MD, 21704
Trilogy® at Lake Frederick 112 FRINGETREE CT, LAKE FREDERICK, VA, 2..., Lake Frederick, VA 22630
$574,900

4 beds

|

3 baths

|

2,080 sq ft

112 FRINGETREE CT, LAKE FREDERICK, VA, 2...
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 19418 PEARL DR, HAGERSTOWN, MD, 21742, Hagerstown, MD 21742
$435,000

2 beds

|

2 baths

|

2,735 sq ft

19418 PEARL DR, HAGERSTOWN, MD, 21742
Community: Emerald Pointe
Birchwood at Brambleton 23665 HAVELOCK WALK TER 406, ASHBURN, VA..., Ashburn, VA 20148
$499,900

1 beds

|

2 baths

|

1,229 sq ft

|

Condo

23665 HAVELOCK WALK TER 406, ASHBURN, VA...
Lansdowne Woods of Virginia 19355 CYPRESS RIDGE TER 905, LEESBURG, V..., Leesburg, VA 20176
$349,000

1 beds

|

2 baths

|

874 sq ft

|

Condo

19355 CYPRESS RIDGE TER 905, LEESBURG, V...
Heritage Hunt 13972 REAL QUITE CT, GAINESVILLE, VA, 20..., Gainesville, VA 20155
$760,000

4 beds

|

4 baths

|

3,256 sq ft

13972 REAL QUITE CT, GAINESVILLE, VA, 20...
Community: Heritage Hunt
Lansdowne Woods of Virginia 19365 CYPRESS RIDGE TER 1105, LEESBURG, ..., Leesburg, VA 20176
$375,000

2 beds

|

2 baths

|

1,038 sq ft

|

Condo

19365 CYPRESS RIDGE TER 1105, LEESBURG, ...
Lansdowne Woods of Virginia 19370 MAGNOLIA GROVE SQ L04, LEESBURG, V..., Leesburg, VA 20176
$594,900

2 beds

|

2 baths

|

1,708 sq ft

|

Condo

19370 MAGNOLIA GROVE SQ L04, LEESBURG, V...
Trilogy® at Lake Frederick 106 ATLANTIS LN, LAKE FREDERICK, VA, 226..., Lake Frederick, VA 22630
$614,900

4 beds

|

3 baths

|

3,114 sq ft

106 ATLANTIS LN, LAKE FREDERICK, VA, 226...
JerMae Estates 5 GEOLEY CT, THURMONT, MD, 21788, Thurmont, MD 21788
$476,000

4 beds

|

3 baths

|

2,038 sq ft

5 GEOLEY CT, THURMONT, MD, 21788
Community: JerMae Estates
Want to learn more about 55+ communities in Winchester Area? 55places can help!
Questions? Call us: (540) 452-4199
Birchwood at Brambleton 42874 FIREFLY SONATA TER 403, ASHBURN, V..., Ashburn, VA 20148
$609,000

3 beds

|

2 baths

|

1,712 sq ft

|

Condo

42874 FIREFLY SONATA TER 403, ASHBURN, V...
Lansdowne Woods of Virginia 19375 CYPRESS RIDGE TER 719, LEESBURG, V..., Leesburg, VA 20176
$383,250

2 beds

|

2 baths

|

1,101 sq ft

|

Condo

19375 CYPRESS RIDGE TER 719, LEESBURG, V...
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.



Frequently Asked Questions


Connect with an agent
Want to learn more about 55+ communities in the Winchester Area?
  • Insights and market stats
  • Instant new home alerts
  • Answers from local 55+ experts

Call us now: (540) 452-4199

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

Call us: (540) 452-4199
51 communities
Remove Boundaries ×
Map Satellite

Reinmlsx

The listings data displayed on this medium comes in part from the Real Estate Information Network Inc. (REIN) and has been authorized by participating listing Broker Members of REIN for display. REIN's listings are based upon Data submitted by its Broker Members, and REIN therefore makes no representation or warranty regarding the accuracy of the Data. All users of REIN's listings database should confirm the accuracy of the listing information directly with the listing agent.
© 2026 REIN. REIN's listings Data and information is protected under federal copyright laws. Federal law prohibits, among other acts, the unauthorized copying or alteration of, or preparation of derivative works from, all or any part of copyrighted materials, including certain compilations of Data and information. COPYRIGHT VIOLATORS MAY BE SUBJECT TO SEVERE FINES AND PENALTIES UNDER FEDERAL LAW.
REIN updates its listings on a daily basis. Data last updated: Aug 04, 2026.
This application does not include information on all of the properties available for sale at this time.

Call Us Call Us
Scroll to Top