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 2
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:
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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
Woodbrook Village
![222 CRESTWOOD LN, WINCHESTER, VA, 22602, Winchester, VA 22602]()
MLS VAFV2037554 • ERA Oakcrest Realty, Inc., Tiff...
Potomac Green
![44420 SUNSET MAPLE DR, ASHBURN, VA, 2014..., Ashburn, VA 20147]()
MLS VALO2111136 • Samson Properties, Anne Elaine ...
Trilogy® at Lake Frederick
![117 MALLARD DR, LAKE FREDERICK, VA, 2263..., Lake Frederick, VA 22630]()
3 beds
|4 baths
|3,601 sq ft
117 MALLARD DR, LAKE FREDERICK, VA, 2263...
Community: Trilogy® at Lake Frederick
MLS VAFV2037046 • Realty ONE Group Capital, Kyle ...
Willow Run
![111 TRELLIS VIEW LN, WINCHESTER, VA, 226..., Winchester, VA 22602]()
MLS VAFV2035394 • D R Horton Realty of Virginia L...
New
Winchester Landing
![122 HARDY WAY, WINCHESTER, VA, 22602, Winchester, VA 22602]()
MLS VAFV2038724 • CENTURY 21 New Millennium, Kath...
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(540) 452-4199
Birchwood at Brambleton
![23631 HAVELOCK WALK TER 404, ASHBURN, VA..., Ashburn, VA 20148]()
2 beds
|2 baths
|1,959 sq ft
|Condo
23631 HAVELOCK WALK TER 404, ASHBURN, VA...
Community: Birchwood at Brambleton
MLS VALO2111814 • TTR Sotheby's International Rea...
Birchwood at Brambleton
![23595 GOLDEN EMBERS SQ, ASHBURN, VA, 201..., Ashburn, VA 20148]()
3 beds
|4 baths
|3,637 sq ft
23595 GOLDEN EMBERS SQ, ASHBURN, VA, 201...
Community: Birchwood at Brambleton
MLS VALO2111758 • Keller Williams Realty, Matt Bo...
Potomac Green
![44385 MALTESE FALCON SQ, ASHBURN, VA, 20..., Ashburn, VA 20147]()
MLS VALO2109626 • Samson Properties, Andrea M. Ha...
Heritage Highlands
![67 HARPERS MILL WAY, LOVETTSVILLE, VA, 2..., Lovettsville, VA 20180]()
2 beds
|3 baths
|2,119 sq ft
67 HARPERS MILL WAY, LOVETTSVILLE, VA, 2...
Community: Heritage Highlands
MLS VALO2113040 • Keller Williams Realty, Kevin M...
Download the Ultimate 55+ Homebuying Guide
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Heritage Hunt
![13612 RYTON RIDGE LN, GAINESVILLE, VA, 2..., Gainesville, VA 20155]()
MLS VAPW2107150 • RE/MAX Gateway, Fawn Deitsch
New
The Highlands at Blue Ridge Shadows
![47 HICKORY SHAFT CT, FRONT ROYAL, VA, 22..., Front Royal, VA 22630]()
4 beds
|4 baths
|3,482 sq ft
47 HICKORY SHAFT CT, FRONT ROYAL, VA, 22...
Community: The Highlands at Blue Ridge Shadows
MLS VAWR2013078 • Keller Williams Realty, Alicia ...
Regency at Dominion Valley
![15201 ROYAL CREST DR APT 407, HAYMARKET,..., Haymarket, VA 20169]()
2 beds
|2 baths
|1,538 sq ft
|Condo
15201 ROYAL CREST DR APT 407, HAYMARKET,...
Community: Regency at Dominion Valley
MLS VAPW2106110 • Samson Properties, Kelly L Snel...
Heritage Hunt
![6880 SADDLE RUN WAY, GAINESVILLE, VA, 20..., Gainesville, VA 20155]()
MLS VAPW2106694 • Samson Properties, Earnest W Go...
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55places can help!
Questions? Call us:
(540) 452-4199
Heritage Hunt
![6868 SADDLE RUN WAY, GAINESVILLE, VA, 20..., Gainesville, VA 20155]()
MLS VAPW2104596 • Samson Properties, Earnest W Go...
Heritage Hunt
![13963 CHELMSFORD DR, GAINESVILLE, VA, 20..., Gainesville, VA 20155]()
MLS VAPW2107290 • Keller Williams Realty, Matias ...
Lansdowne Woods of Virginia
![19355 CYPRESS RIDGE TER 114, LEESBURG, V..., Leesburg, VA 20176]()
2 beds
|2 baths
|1,038 sq ft
|Condo
19355 CYPRESS RIDGE TER 114, LEESBURG, V...
Community: Lansdowne Woods of Virginia
MLS VALO2109516 • Real Broker, LLC, Ashraf Morsi
Regency at Dominion Valley
![5429 TREVINO DR, HAYMARKET, VA, 20169, Haymarket, VA 20169]()
3 beds
|3 baths
|2,524 sq ft
5429 TREVINO DR, HAYMARKET, VA, 20169
Community: Regency at Dominion Valley
MLS VAPW2109318 • 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.
Lansdowne Woods of Virginia
![19365 CYPRESS RIDGE TER UNIT 1102, LEESB..., Leesburg, VA 20176]()
2 beds
|2 baths
|1,105 sq ft
|Condo
19365 CYPRESS RIDGE TER UNIT 1102, LEESB...
Community: Lansdowne Woods of Virginia
MLS VALO2105996 • Keller Williams Realty, Nancy L...
Lansdowne Woods of Virginia
![19385 CYPRESS RIDGE TER UNIT 522, LEESBU..., Leesburg, VA 20176]()
2 beds
|2 baths
|1,101 sq ft
|Condo
19385 CYPRESS RIDGE TER UNIT 522, LEESBU...
Community: Lansdowne Woods of Virginia
MLS VALO2104358 • Real Broker, LLC, Peter B Knapp
Heritage Hunt
![7065 HERITAGE HUNT DR 203, GAINESVILLE, ..., Gainesville, VA 20155]()
2 beds
|2 baths
|1,421 sq ft
|Condo
7065 HERITAGE HUNT DR 203, GAINESVILLE, ...
Community: Heritage Hunt
MLS VAPW2106402 • Corcoran McEnearney, Rebecca B ...
The Village at Harvest Ridge
![147 HARVEST RIDGE DR, WINCHESTER, VA, 22..., Winchester, VA 22601]()
3 beds
|3 baths
|3,153 sq ft
147 HARVEST RIDGE DR, WINCHESTER, VA, 22...
Community: The Village at Harvest Ridge
MLS VAFV2036978 • ERA Oakcrest Realty, Inc., Nata...
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Lansdowne Woods of Virginia
![19375 CYPRESS RIDGE TER UNIT 708, LEESBU..., Leesburg, VA 20176]()
2 beds
|2 baths
|1,315 sq ft
|Condo
19375 CYPRESS RIDGE TER UNIT 708, LEESBU...
Community: Lansdowne Woods of Virginia
MLS VALO2110470 • Samson Properties, Andrew M Nor...
Lansdowne Woods of Virginia
![19375 CYPRESS RIDGE TER 901, LEESBURG, V..., Leesburg, VA 20176]()
3 beds
|2 baths
|1,534 sq ft
|Condo
19375 CYPRESS RIDGE TER 901, LEESBURG, V...
Community: Lansdowne Woods of Virginia
MLS VALO2113168 • Compass, Sue G Smith
Lansdowne Woods of Virginia
![19385 CYPRESS RIDGE TER UNIT 920, LEESBU..., Leesburg, VA 20176]()
3 beds
|2 baths
|1,475 sq ft
|Condo
19385 CYPRESS RIDGE TER UNIT 920, LEESBU...
Community: Lansdowne Woods of Virginia
MLS VALO2107774 • Long & Foster Real Estate, Inc....
Trilogy® at Lake Frederick
![105 BAYHILL TER, LAKE FREDERICK, VA, 226..., Lake Frederick, VA 22630]()
3 beds
|3 baths
|1,962 sq ft
105 BAYHILL TER, LAKE FREDERICK, VA, 226...
Community: Trilogy® at Lake Frederick
MLS VAFV2036228 • RE/MAX Roots, David K Spence
Cottage Glen
![129 DOONBEG CT, WINCHESTER, VA, 22602, Winchester, VA 22602]()
MLS VAFV2038410 • ERA Oakcrest Realty, Inc., Tere...
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
![6920 NETHERSTONE CT, GAINESVILLE, VA, 20..., Gainesville, VA 20155]()
MLS VAPW2107960 • RLAH @properties, Candace Moe
Woodbrook Village
![203 CRESTWOOD LN, WINCHESTER, VA, 22602, Winchester, VA 22602]()
MLS VAFV2038228 • MarketPlace REALTY, Jen Richard...
Gatherings at Potomac Station
![750 MOUNT AIRY TER NE UNIT 403B, LEESBUR..., Leesburg, VA 20176]()
2 beds
|2 baths
|1,410 sq ft
|Condo
750 MOUNT AIRY TER NE UNIT 403B, LEESBUR...
Community: Gatherings at Potomac Station
MLS VALO2112922 • Pearson Smith Realty, LLC, Vick...
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Lansdowne Woods of Virginia
![19355 CYPRESS RIDGE TER UNIT 503, LEESBU..., Leesburg, VA 20176]()
2 beds
|2 baths
|1,251 sq ft
|Condo
19355 CYPRESS RIDGE TER UNIT 503, LEESBU...
Community: Lansdowne Woods of Virginia
MLS VALO2110636 • Samson Properties, Andrew M Nor...
Gatherings at Wellington
![10273 FOUNTAIN CIR 202, MANASSAS, VA, 20..., Manassas, VA 20110]()
3 beds
|2 baths
|2,006 sq ft
|Condo
10273 FOUNTAIN CIR 202, MANASSAS, VA, 20...
Community: Gatherings at Wellington
MLS VAMN2009240 • Washington Fine Properties, LLC...
Gatherings at Wellington
![9202 CHARLESTON DR 307, MANASSAS, VA, 20..., Manassas, VA 20110]()
3 beds
|2 baths
|2,006 sq ft
|Condo
9202 CHARLESTON DR 307, MANASSAS, VA, 20...
Community: Gatherings at Wellington
MLS VAMN2009116 • Century 21 Redwood Realty, Brit...
Willow Run
![113 TRELLIS VIEW LN, WINCHESTER, VA, 226..., Winchester, VA 22602]()
MLS VAFV2035396 • D R Horton Realty of Virginia L...
Heritage Hunt
![7065 HERITAGE HUNT DR 108, GAINESVILLE, ..., Gainesville, VA 20155]()
2 beds
|2 baths
|1,292 sq ft
|Condo
7065 HERITAGE HUNT DR 108, GAINESVILLE, ...
Community: Heritage Hunt
MLS VAPW2108662 • Samson Properties, Sharon A Amb...
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
![15251 ROYAL CREST DR APT 103, HAYMARKET,..., Haymarket, VA 20169]()
2 beds
|2 baths
|1,499 sq ft
|Condo
15251 ROYAL CREST DR APT 103, HAYMARKET,...
Community: Regency at Dominion Valley
MLS VAPW2107738 • Samson Properties, James Matthe...
Montebello
![21630 HAWKSBILL HIGH CIR UNIT 403, STERL..., Sterling, VA 20164]()
2 beds
|2 baths
|1,435 sq ft
|Condo
21630 HAWKSBILL HIGH CIR UNIT 403, STERL...
Community: Montebello
MLS VALO2111258 • Samson Properties, Andrea M. Ha...
Trilogy® at Lake Frederick
![112 BETONY CT, LAKE FREDERICK, VA, 22630, Lake Frederick, VA 22630]()
3 beds
|3 baths
|3,434 sq ft
112 BETONY CT, LAKE FREDERICK, VA, 22630
Community: Trilogy® at Lake Frederick
MLS VAFV2038562 • Keller Williams Realty, Matt Bo...
Montebello
![21630 HAWKSBILL HIGH CIR UNIT 204, STERL..., Sterling, VA 20164]()
2 beds
|2 baths
|1,640 sq ft
|Condo
21630 HAWKSBILL HIGH CIR UNIT 204, STERL...
Community: Montebello
MLS VALO2101016 • Samson Properties, Andrea M. Ha...
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Winchester Landing
![140 MCCORMICK CIR APT 302, WINCHESTER, V..., Winchester, VA 22602]()
2 beds
|2 baths
|1,156 sq ft
140 MCCORMICK CIR APT 302, WINCHESTER, V...
Community: Winchester Landing
MLS VAFV2038584 • Keller Williams Realty, Karl Ac...
Willow Run
![113 SCENTED ROSE WAY, WINCHESTER, VA, 22..., Winchester, VA 22602]()
MLS VAFV2035260 • D R Horton Realty of Virginia L...
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.
