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 - Page 3
49 communities near Winchester Area
117 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
$400Ks
Cedar Meadows, White Post, VA
Resale Only
|
55+ age-restricted
|
Built 2010 - 2022
|
129 homes
5 rating (1 reviews)
![Willow Lawn Cottages]()
$300Ks
Willow Lawn Cottages, Winchester, VA
Resale Only
|
55+ age-restricted
|
Built 1999 - 2004
|
120 homes
$300Ks
- $400Ks
Cross Creek Village, Winchester, VA
Resale Only
|
55+ age-restricted
|
Built 2001 - 2004
|
90 homes
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$500Ks
- $600Ks
The Village at Harvest Ri..., Winchester, VA
Resale Only
|
55+ age-restricted
|
Built 2005 - 2016
|
82 homes
$300Ks
Woodbrook Village, Winchester, VA
Resale Only
|
55+ age-restricted
|
Built 1999 - 2001
|
81 homes
$300Ks
- $400Ks
Heritage Highlands, Lovettsville, VA
Resale Only
|
55+ age-restricted
|
Built 2017 - 2020
|
80 homes
$400Ks
- $700Ks
The Highlands at Blue Rid..., Front Royal, VA
Resale Only
|
55+ age-restricted
|
Built 2017 - 2019
|
42 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.
$500Ks
Abrams Chase, Winchester, VA
New Construction
|
55+ age-restricted
|
Built 2020 - present
|
13 homes
5 rating (3 reviews)
![Heritage Hunt]()
$400Ks
- $800Ks
Heritage Hunt, Gainesville, VA
Resale Only
|
55+ age-restricted
|
Built 1998 - 2009
|
1,863 homes
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2 rating (1 reviews)
![Birchwood at Brambleton]()
$400Ks
- $900Ks
Birchwood at Brambleton, Ashburn, VA
New and Resale
|
55+ age-restricted
|
Built 2016 - present
|
1,502 homes
5 rating (2 reviews)
![Potomac Green]()
$600Ks
- $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
- $500Ks
Regency at Dominion Valle..., Haymarket, VA
Resale Only
|
55+ age-restricted
|
Built 2001 - 2017
|
855 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.
$400Ks
- $600Ks
The Woodlands of Urbana, Urbana, MD
Resale Only
|
55+ age-restricted
|
Built 2019 - 2025
|
565 homes
5 rating (1 reviews)
![Crestwood Village]()
$300Ks
Crestwood Village, Frederick, MD
Resale Only
|
55+ age-restricted
|
Built 1979 - 1999
|
550 homes
$400Ks
- $700Ks
Carter's Mill, Haymarket, VA
New Construction
|
55+ age-restricted
|
Built 2020 - present
|
480 homes
3 rating (2 reviews)
![Dunbarton]()
$600Ks
Dunbarton, Bristow, VA
Resale Only
|
55+ age-restricted
|
Built 2000 - 2009
|
479 homes
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(540) 452-4199
$600Ks
- $1Ms
Montebello, Sterling, VA
New and Resale
|
55+ age-restricted
|
Built 2022 - present
|
450 homes
$800Ks
- $900Ks
Regency at Ashburn, Ashburn, VA
Resale Only
|
55+ age-restricted
|
Built 2013 - 2020
|
268 homes
$300Ks
- $400Ks
Emerald Pointe, Hagerstown, MD
New and Resale
|
55+ age-restricted
|
Built 2008 - present
|
250 homes
$700Ks
- $900Ks
The Retreat at Poland Hil..., Chantilly, VA
Resale Only
|
55+ age-restricted
|
Built 2020 - 2022
|
219 homes
$900Ks
Regency at Creekside, Gainesville, VA
Resale Only
|
55+ age-restricted
|
Built 2016 - 2020
|
208 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.
$400Ks
- $700Ks
Central Parke at Lowes Is..., Sterling, VA
Resale Only
|
55+ age-restricted
|
Built 2003 - 2005
|
181 homes
$300Ks
Rosehill Manor Villas, Hagerstown, MD
New Construction
|
55+ age-restricted
|
Built 2022 - present
|
177 homes
$900Ks
Regency at Belmont, Ashburn, VA
New Construction
|
55+ age-restricted
|
Built 2021 - present
|
145 homes
Want to learn more about 55+ communities in Winchester Area?
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Questions? Call us:
(540) 452-4199
5 rating (1 reviews)
![Gatherings at Wellington]()
$300Ks
- $400Ks
Gatherings at Wellington, Manassas, VA
Resale Only
|
55+ age-restricted
|
Built 2011 - 2016
|
135 homes
$500Ks
- $800Ks
Vistas at Lansdowne, Lansdowne, VA
Resale Only
|
55+ age-restricted
|
Built 2015 - 2020
|
120 homes
$700Ks
- $800Ks
Lexington 7, Ashburn, VA
Resale Only
|
55+ age-restricted
|
Built 2017 - 2020
|
113 homes
$300Ks
- $400Ks
Suffield Meadows, Warrenton, VA
Resale Only
|
55+ age-restricted
|
Built 2005 - 2011
|
112 homes
$400Ks
- $500Ks
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.
$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
Four Seasons at Vint Hill, Warrenton, VA
Resale Only
|
55+ age-restricted
|
Built 2004 - 2006
|
100 homes
$500Ks
- $600Ks
Boxwood Villas, Urbana, MD
Resale Only
|
55+ age-restricted
|
Built 2019 - 2021
|
92 homes
$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
Four Seasons at Ashburn V..., Ashburn, VA
Resale Only
|
55+ age-restricted
|
Built 2005 - 2005
|
80 homes
Lansdowne Woods of Virginia
![19355 CYPRESS RIDGE TER 612, LEESBURG, V..., Leesburg, VA 20176]()
2 beds
|2 baths
|1,500 sq ft
|Condo
19355 CYPRESS RIDGE TER 612, LEESBURG, V...
Community: Lansdowne Woods of Virginia
MLS VALO2108204 • Keller Williams Realty, Kimberl...
Cadence at Lansdowne
![43917 MARITIME SONG TER, LEESBURG, VA, 2..., Leesburg, VA 20176]()
3 beds
|3 baths
|2,389 sq ft
43917 MARITIME SONG TER, LEESBURG, VA, 2...
Community: Cadence at Lansdowne
MLS VALO2112442 • Samson Properties, Caren R O'Br...
Willow Run
![111 SCENTED ROSE WAY, WINCHESTER, VA, 22..., Winchester, VA 22602]()
MLS VAFV2035740 • D R Horton Realty of Virginia L...
Trilogy® at Lake Frederick
![103 BURKWOOD TER, LAKE FREDERICK, VA, 22..., Lake Frederick, VA 22630]()
3 beds
|3 baths
|2,376 sq ft
103 BURKWOOD TER, LAKE FREDERICK, VA, 22...
Community: Trilogy® at Lake Frederick
MLS VAFV2036998 • RE/MAX Roots, Sheila R Pack
The Retreat at Poland Hill
![43441 BETTYS FARM DR, CHANTILLY, VA, 201..., Chantilly, VA 20152]()
4 beds
|4 baths
|3,553 sq ft
43441 BETTYS FARM DR, CHANTILLY, VA, 201...
Community: The Retreat at Poland Hill
MLS VALO2110858 • Metro House, Lizzie A Helmig
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Lexington Square
![44510 LOWESTOFT SQ, ASHBURN, VA, 20147, Ashburn, VA 20147]()
MLS VALO2112470 • Pearson Smith Realty, LLC, Shan...
Lexington 7
![44510 LOWESTOFT SQ, ASHBURN, VA, 20147, Ashburn, VA 20147]()
MLS VALO2112470 • Pearson Smith Realty, LLC, Shan...
Lexington Square
![44508 LOWESTOFT SQ, ASHBURN, VA, 20147, Ashburn, VA 20147]()
MLS VALO2109594 • Pearson Smith Realty, LLC, Shan...
Lexington 7
![44508 LOWESTOFT SQ, ASHBURN, VA, 20147, Ashburn, VA 20147]()
MLS VALO2109594 • Pearson Smith Realty, LLC, Shan...
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
![13792 CHARISMATIC WAY, GAINESVILLE, VA, ..., Gainesville, VA 20155]()
MLS VAPW2109234 • RE/MAX Distinctive Real Estate,...
Heritage Hunt
![13746 HERITAGE VALLEY WAY, GAINESVILLE, ..., Gainesville, VA 20155]()
MLS VAPW2106872 • Coldwell Banker Realty, James P...
Trilogy® at Lake Frederick
![102 BETONY CT, LAKE FREDERICK, VA, 22630, Lake Frederick, VA 22630]()
3 beds
|3 baths
|3,434 sq ft
102 BETONY CT, LAKE FREDERICK, VA, 22630
Community: Trilogy® at Lake Frederick
MLS VAFV2036118 • Keller Williams Realty, Matt Bo...
Lansdowne Woods of Virginia
![19385 CYPRESS RIDGE TER UNIT 404, LEESBU..., Leesburg, VA 20176]()
2 beds
|2 baths
|1,038 sq ft
|Condo
19385 CYPRESS RIDGE TER UNIT 404, LEESBU...
Community: Lansdowne Woods of Virginia
MLS VALO2111106 • Samson Properties, Andrew M Nor...
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(540) 452-4199
Lansdowne Woods of Virginia
![19365 CYPRESS RIDGE TER UNIT 621, LEESBU..., Leesburg, VA 20176]()
2 beds
|2 baths
|1,509 sq ft
|Condo
19365 CYPRESS RIDGE TER UNIT 621, LEESBU...
Community: Lansdowne Woods of Virginia
MLS VALO2111734 • Samson Properties, Andrew M Nor...
Lansdowne Woods of Virginia
![19365 CYPRESS RIDGE TER UNIT 1022, LEESB..., Leesburg, VA 20176]()
2 beds
|2 baths
|1,105 sq ft
|Condo
19365 CYPRESS RIDGE TER UNIT 1022, LEESB...
Community: Lansdowne Woods of Virginia
MLS VALO2110570 • Samson Properties, Andrew M Nor...
Birchwood at Brambleton
![23606 HAVELOCK WALK TER, ASHBURN, VA, 20..., Ashburn, VA 20148]()
3 beds
|3 baths
|2,592 sq ft
|Condo
23606 HAVELOCK WALK TER, ASHBURN, VA, 20...
Community: Birchwood at Brambleton
MLS VALO2111310 • RE/MAX Real Estate Connections,...
Birchwood at Brambleton
![23590 RAYTOWN TER, ASHBURN, VA, 20148, Ashburn, VA 20148]()
3 beds
|4 baths
|2,742 sq ft
23590 RAYTOWN TER, ASHBURN, VA, 20148
Community: Birchwood at Brambleton
MLS VALO2112572 • Century 21 Redwood Realty, Chri...
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
![23630 WINTERDAY DR, ASHBURN, VA, 20148, Ashburn, VA 20148]()
3 beds
|4 baths
|2,742 sq ft
23630 WINTERDAY DR, ASHBURN, VA, 20148
Community: Birchwood at Brambleton
MLS VALO2111914 • Century 21 Redwood Realty, Chri...
Birchwood at Brambleton
![23664 HAVELOCK WALK TER APT 101, ASHBURN..., Ashburn, VA 20148]()
2 beds
|3 baths
|1,576 sq ft
|Condo
23664 HAVELOCK WALK TER APT 101, ASHBURN...
Community: Birchwood at Brambleton
MLS VALO2112546 • McWilliams/Ballard Inc., Robert...
Birchwood at Brambleton
![23664 HAVELOCK WALK TER APT 205, ASHBURN..., Ashburn, VA 20148]()
2 beds
|2 baths
|1,553 sq ft
|Condo
23664 HAVELOCK WALK TER APT 205, ASHBURN...
Community: Birchwood at Brambleton
MLS VALO2112548 • McWilliams/Ballard Inc., Robert...
Heritage Hunt
![6159 FERRIER CT, GAINESVILLE, VA, 20155, Gainesville, VA 20155]()
MLS VAPW2105670 • Keller Williams Realty, Sarah A...
Want to learn more about 55+ communities in Winchester Area?
55places can help!
Questions? Call us:
(540) 452-4199
Regency at Dominion Valley
![15100 HEATHER MILL LN APT 407, HAYMARKET..., Haymarket, VA 20169]()
2 beds
|2 baths
|1,538 sq ft
|Condo
15100 HEATHER MILL LN APT 407, HAYMARKET...
Community: Regency at Dominion Valley
MLS VAPW2107710 • Samson Properties, Kimberly Sne...
Suffield Meadows
![6704 HOLLY FARM LN UNIT 109, WARRENTON, ..., Warrenton, VA 20187]()
MLS VAFQ2018114 • Piedmont Fine Properties, Karen...
Birchwood at Brambleton
![23631 HAVELOCK WALK TER 318, ASHBURN, VA..., Ashburn, VA 20148]()
2 beds
|2 baths
|1,967 sq ft
|Condo
23631 HAVELOCK WALK TER 318, ASHBURN, VA...
Community: Birchwood at Brambleton
MLS VALO2105714 • Pearson Smith Realty, LLC, Carl...
Lansdowne Woods of Virginia
![19375 CYPRESS RIDGE TER 601, LEESBURG, V..., Leesburg, VA 20176]()
3 beds
|2 baths
|1,534 sq ft
|Condo
19375 CYPRESS RIDGE TER 601, LEESBURG, V...
Community: Lansdowne Woods of Virginia
MLS VALO2111074 • Samson Properties, Andrew M Nor...
Potomac Green
![44529 BLUERIDGE MEADOWS DR, ASHBURN, VA,..., Ashburn, VA 20147]()
MLS VALO2109410 • Weichert, REALTORS, Cecil R Fra...
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
![23688 BOLTON CRESCENT TER APT 204, ASHBU..., Ashburn, VA 20148]()
2 beds
|2 baths
|1,280 sq ft
|Condo
23688 BOLTON CRESCENT TER APT 204, ASHBU...
Community: Birchwood at Brambleton
MLS VALO2110820 • Long & Foster Real Estate, Inc....
Birchwood at Brambleton
![43016 DEBONAIR TER, ASHBURN, VA, 20148, Ashburn, VA 20148]()
3 beds
|4 baths
|2,742 sq ft
43016 DEBONAIR TER, ASHBURN, VA, 20148
Community: Birchwood at Brambleton
MLS VALO2109274 • Century 21 Redwood Realty, Chri...
Birchwood at Brambleton
![43089 GREELEY SQ, ASHBURN, VA, 20148, Ashburn, VA 20148]()
3 beds
|3 baths
|2,491 sq ft
43089 GREELEY SQ, ASHBURN, VA, 20148
Community: Birchwood at Brambleton
MLS VALO2098976 • Century 21 Redwood Realty, Chri...
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Birchwood at Brambleton
![42788 MACBETH TER, ASHBURN, VA, 20148, Ashburn, VA 20148]()
3 beds
|3 baths
|2,669 sq ft
42788 MACBETH TER, ASHBURN, VA, 20148
Community: Birchwood at Brambleton
MLS VALO2107498 • Century 21 Redwood Realty, AnaM...
Trilogy® at Lake Frederick
![103 PLANETREE CT, LAKE FREDERICK, VA, 22..., Lake Frederick, VA 22630]()
3 beds
|3 baths
|3,589 sq ft
103 PLANETREE CT, LAKE FREDERICK, VA, 22...
Community: Trilogy® at Lake Frederick
MLS VAFV2037204 • Keller Williams Realty, Matt Bo...
Winchester Landing
![100 MAURY WAY, WINCHESTER, VA, 22602, Winchester, VA 22602]()
MLS VAFV2038220 • Keller Williams Realty, Matt Bo...
Winchester Landing
![140 MCCORMICK CIR APT 403, WINCHESTER, V..., Winchester, VA 22602]()
2 beds
|2 baths
|1,156 sq ft
|Condo
140 MCCORMICK CIR APT 403, WINCHESTER, V...
Community: Winchester Landing
MLS VAFV2035264 • Realty ONE Group Old Towne, Sha...
Heritage Hunt
![6900 TRED AVON PL, GAINESVILLE, VA, 2015..., Gainesville, VA 20155]()
MLS VAPW2106954 • Long & Foster Real Estate, Inc....
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
![43011 DEBONAIR TER, ASHBURN, VA, 20148, Ashburn, VA 20148]()
3 beds
|4 baths
|2,742 sq ft
43011 DEBONAIR TER, ASHBURN, VA, 20148
Community: Birchwood at Brambleton
MLS VALO2104994 • Century 21 Redwood Realty, Chri...
Birchwood at Brambleton
![42972 TRUMAN TER, ASHBURN, VA, 20148, Ashburn, VA 20148]()
4 beds
|4 baths
|2,742 sq ft
42972 TRUMAN TER, ASHBURN, VA, 20148
Community: Birchwood at Brambleton
MLS VALO2106648 • Century 21 Redwood Realty, Chri...
Birchwood at Brambleton
![42920 FIREFLY SONATA TER UNIT 307, ASHBU..., Ashburn, VA 20148]()
3 beds
|2 baths
|1,630 sq ft
|Condo
42920 FIREFLY SONATA TER UNIT 307, ASHBU...
Community: Birchwood at Brambleton
MLS VALO2108516 • CENTURY 21 New Millennium, Rodn...
Frequently Asked Questions
In the Winchester Area, there are no large communities, 1 medium community with 500-1000 homes, and 9 small communities with less than 500 homes.
The smallest 55+ communities in the Winchester Area has 13 homes, the largest has 950 homes, and the average communities consists of 161 homes.
Yes, there are new 55+ homes available in the Winchester Area. The most recent communities started in the Winchester Area include Abrams Chase, Cottage Glen, The Highlands at Blue Ridge Shadows. There are also 3 communities in the Winchester Area that offer new construction homes, including Abrams Chase, Trilogy® at Lake Frederick, Cottage Glen.
Yes, there are gated 55+ communities in the Winchester Area. Approximately 30.0% of 55+ communities in the area are gated. For instance, Cedar Meadows is a gated communities with 129 homes, and Trilogy® at Lake Frederick is another gated communities with 950 homes.
On average, listings in 55+ communities in the Winchester Area stay on the market for around 602 days. The average price of homes for sale in these communities is approximately $484,040, though prices can range widely based on the size, location, and amenities of the communities. For example, homes in The Highlands at Blue Ridge Shadows average around $615,000, while homes in Cottage Glen average around $479,500.
Want to learn more about 55+ communities in the Winchester Area?
- Insights and market stats
- Instant new home alerts
- Answers from local 55+ experts
Want to learn more about 55+ communities in Winchester Area?
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© 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: Jan 10, 2026.
This application does not include information on all of the properties available for sale at this time.
