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
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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(540) 452-4199
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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.
Read the Ultimate 55+ Rental Guide
Thinking about renting in a 55+ active adult community? Our free guide has all the must-know info and practical tips to help you navigate 55+ renting and find your ideal next home in a 55+ community.
$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
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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
Read the Ultimate 55+ Rental Guide
Thinking about renting in a 55+ active adult community? Our free guide has all the must-know info and practical tips to help you navigate 55+ renting and find your ideal next home in a 55+ community.
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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$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
Want to learn more about 55+ rental communities in Winchester Area?
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Questions? Call us:
(540) 452-4199
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Thinking about renting in a 55+ active adult community? Our free guide has all the must-know info and practical tips to help you navigate 55+ renting and find your ideal next home in a 55+ community.
$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
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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
Read the Ultimate 55+ Rental Guide
Thinking about renting in a 55+ active adult community? Our free guide has all the must-know info and practical tips to help you navigate 55+ renting and find your ideal next home in a 55+ community.
$500Ks
The Village at Foxfield, Middletown, MD
Resale Only
|
55+ age-restricted
|
Built 2003 - 2012
|
81 homes
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Questions? Call us:
(540) 452-4199
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(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
The Woodlands of Urbana
![3520 STARLIGHT ST 302, FREDERICK, MD, 21..., Frederick, MD 21704]()
2 beds
|2 baths
|1,489 sq ft
|Condo
3520 STARLIGHT ST 302, FREDERICK, MD, 21...
Community: The Woodlands of Urbana
MLS MDFR2073896 • Compass, Ross J Wilhelm
Birchwood at Brambleton
![23630 HAVELOCK WALK TER UNIT 405, ASHBUR..., Ashburn, VA 20148]()
2 beds
|2 baths
|1,059 sq ft
|Condo
23630 HAVELOCK WALK TER UNIT 405, ASHBUR...
Community: Birchwood at Brambleton
MLS VALO2113676 • Hunt Country Sotheby's Internat...
Winchester Landing
![151 MCCORMICK CIR APT 203, WINCHESTER, V..., Winchester, VA 22602]()
2 beds
|2 baths
|1,156 sq ft
|Condo
151 MCCORMICK CIR APT 203, WINCHESTER, V...
Community: Winchester Landing
MLS VAFV2038694 • RE/MAX Roots, Roxanna D Grimes
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...
Woodbrook Village
![222 CRESTWOOD LN, WINCHESTER, VA, 22602, Winchester, VA 22602]()
MLS VAFV2037554 • ERA Oakcrest Realty, Inc., Tiff...
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Questions? Call us:
(540) 452-4199
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(540) 452-4199
Lansdowne Woods of Virginia
![19350 MAGNOLIA SQ 308, LEESBURG, VA, 201..., Leesburg, VA 20176]()
2 beds
|2 baths
|1,444 sq ft
|Condo
19350 MAGNOLIA SQ 308, LEESBURG, VA, 201...
Community: Lansdowne Woods of Virginia
MLS VALO2113544 • Pearson Smith Realty, LLC, Davi...
Birchwood at Brambleton
![23669 GOLDEN EMBERS SQ UNIT 303, ASHBURN..., Ashburn, VA 20148]()
3 beds
|2 baths
|2,148 sq ft
|Condo
23669 GOLDEN EMBERS SQ UNIT 303, ASHBURN...
Community: Birchwood at Brambleton
MLS VALO2112344 • Berkshire Hathaway HomeServices...
Birchwood at Brambleton
![42905 SANDY QUAIL TER, ASHBURN, VA, 2014..., Ashburn, VA 20148]()
4 beds
|4 baths
|2,694 sq ft
42905 SANDY QUAIL TER, ASHBURN, VA, 2014...
Community: Birchwood at Brambleton
MLS VALO2113608 • Samson Properties, Tammy L Irby
Lansdowne Woods of Virginia
![19385 CYPRESS RIDGE TER 914, LEESBURG, V..., Leesburg, VA 20176]()
2 beds
|2 baths
|1,509 sq ft
|Condo
19385 CYPRESS RIDGE TER 914, LEESBURG, V...
Community: Lansdowne Woods of Virginia
MLS VALO2108840 • Metropol Realty, Ali Beheshti
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.
Read the Ultimate 55+ Rental Guide
Thinking about renting in a 55+ active adult community? Our free guide has all the must-know info and practical tips to help you navigate 55+ renting and find your ideal next home in a 55+ community.
Trilogy® at Lake Frederick
![108 GADWELL LN, LAKE FREDERICK, VA, 2263..., Lake Frederick, VA 22630]()
3 beds
|4 baths
|3,464 sq ft
108 GADWELL LN, LAKE FREDERICK, VA, 2263...
Community: Trilogy® at Lake Frederick
MLS VAFV2038646 • Berkshire Hathaway HomeServices...
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 ...
Regency at Dominion Valley
![5243 CANYON CREEK WAY, HAYMARKET, VA, 20..., Haymarket, VA 20169]()
2 beds
|2 baths
|2,068 sq ft
5243 CANYON CREEK WAY, HAYMARKET, VA, 20...
Community: Regency at Dominion Valley
MLS VAPW2107080 • Homestead Realty, Michael T Cro...
Gatherings at Wellington
![10275 FOUNTAIN CIR 201, MANASSAS, VA, 20..., Manassas, VA 20110]()
2 beds
|2 baths
|1,441 sq ft
|Condo
10275 FOUNTAIN CIR 201, MANASSAS, VA, 20...
Community: Gatherings at Wellington
MLS VAMN2009920 • Keller Williams Realty, Jennife...
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New
Regency at Dominion Valley
![15110 HEATHER MILL LN APT 305, HAYMARKET..., Haymarket, VA 20169]()
2 beds
|2 baths
|1,551 sq ft
|Condo
15110 HEATHER MILL LN APT 305, HAYMARKET...
Community: Regency at Dominion Valley
MLS VAPW2110370 • Berkshire Hathaway HomeServices...
New
Gatherings at Wellington
![9202 CHARLESTON DR 406, MANASSAS, VA, 20..., Manassas, VA 20110]()
2 beds
|2 baths
|1,558 sq ft
|Condo
9202 CHARLESTON DR 406, MANASSAS, VA, 20...
Community: Gatherings at Wellington
MLS VAMN2009938 • EXIT Realty Pros, Patrick A Clo...
Heritage Hunt
![13963 CHELMSFORD DR, GAINESVILLE, VA, 20..., Gainesville, VA 20155]()
MLS VAPW2107290 • Keller Williams Realty, Matias ...
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Willow Run
![111 SCENTED ROSE WAY, WINCHESTER, VA, 22..., Winchester, VA 22602]()
MLS VAFV2035740 • D R Horton Realty of Virginia L...
Download the Ultimate 55+ Homebuying Guide
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Willow Run
![114 SCENTED ROSE WAY, WINCHESTER, VA, 22..., Winchester, VA 22602]()
MLS VAFV2035742 • D R Horton Realty of Virginia L...
Read the Ultimate 55+ Rental Guide
Thinking about renting in a 55+ active adult community? Our free guide has all the must-know info and practical tips to help you navigate 55+ renting and find your ideal next home in a 55+ community.
Willow Run
![115 SCENTED ROSE WAY, WINCHESTER, VA, 22..., Winchester, VA 22602]()
MLS VAFV2035738 • D R Horton Realty of Virginia L...
Heritage Hunt
![6900 TRED AVON PL, GAINESVILLE, VA, 2015..., Gainesville, VA 20155]()
MLS VAPW2106954 • Long & Foster Real Estate, Inc....
Willow Run
![121 HYDRANGEA WAY, WINCHESTER, VA, 22602, Winchester, VA 22602]()
MLS VAFV2035736 • D R Horton Realty of Virginia L...
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Willow Run
![113 TRELLIS VIEW LN, WINCHESTER, VA, 226..., Winchester, VA 22602]()
MLS VAFV2035396 • D R Horton Realty of Virginia L...
New
Birchwood at Brambleton
![23630 HAVELOCK WALK TER UNIT 410, ASHBUR..., Ashburn, VA 20148]()
2 beds
|2 baths
|1,212 sq ft
|Condo
23630 HAVELOCK WALK TER UNIT 410, ASHBUR...
Community: Birchwood at Brambleton
MLS VALO2113742 • RE/MAX Galaxy, Kofi Mintah
Regency at Belmont
![43921 HURLEYS HUNT TER, ASHBURN, VA, 201..., Ashburn, VA 20147]()
4 beds
|4 baths
|3,255 sq ft
43921 HURLEYS HUNT TER, ASHBURN, VA, 201...
Community: Regency at Belmont
MLS VALO2113054 • Pearson Smith Realty, LLC, Benj...
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...
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 ...
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
![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...
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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...
Potomac Green
![44529 BLUERIDGE MEADOWS DR, ASHBURN, VA,..., Ashburn, VA 20147]()
MLS VALO2109410 • Weichert, REALTORS, Cecil R Fra...
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Woodbrook Village
![203 CRESTWOOD LN, WINCHESTER, VA, 22602, Winchester, VA 22602]()
MLS VAFV2038228 • MarketPlace REALTY, Jen Richard...
Heritage Hunt
![13612 RYTON RIDGE LN, GAINESVILLE, VA, 2..., Gainesville, VA 20155]()
MLS VAPW2107150 • RE/MAX Gateway, Fawn Deitsch
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 ...
Winchester Landing
![122 HARDY WAY, WINCHESTER, VA, 22602, Winchester, VA 22602]()
MLS VAFV2038724 • CENTURY 21 New Millennium, Kath...
Heritage Hunt
![6920 NETHERSTONE CT, GAINESVILLE, VA, 20..., Gainesville, VA 20155]()
MLS VAPW2107960 • RLAH @properties, Candace Moe
Download the Ultimate 55+ Homebuying Guide
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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...
Regency at Dominion Valley
![15251 ROYAL CREST DR APT 306, HAYMARKET,..., Haymarket, VA 20169]()
3 beds
|2 baths
|1,833 sq ft
|Condo
15251 ROYAL CREST DR APT 306, HAYMARKET,...
Community: Regency at Dominion Valley
MLS VAPW2106080 • Century 21 Redwood Realty, Suza...
Willow Run
![119 HYDRANGEA WAY, WINCHESTER, VA, 22602, Winchester, VA 22602]()
MLS VAFV2035348 • D R Horton Realty of Virginia L...
Read the Ultimate 55+ Rental Guide
Thinking about renting in a 55+ active adult community? Our free guide has all the must-know info and practical tips to help you navigate 55+ renting and find your ideal next home in a 55+ community.
Birchwood at Brambleton
![42783 FIREFLY SONATA TER, ASHBURN, VA, 2..., Ashburn, VA 20148]()
2 beds
|3 baths
|2,406 sq ft
42783 FIREFLY SONATA TER, ASHBURN, VA, 2...
Community: Birchwood at Brambleton
MLS VALO2108470 • RE/MAX Allegiance, Dawn R Squir...
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Trilogy® at Lake Frederick
![114 TURNSTONE LN, LAKE FREDERICK, VA, 22..., Lake Frederick, VA 22630]()
3 beds
|4 baths
|3,333 sq ft
114 TURNSTONE LN, LAKE FREDERICK, VA, 22...
Community: Trilogy® at Lake Frederick
MLS VAFV2038318 • Berkshire Hathaway HomeServices...
Lexington 7
![19873 SILVERY BLUE TER, ASHBURN, VA, 201..., Ashburn, VA 20147]()
MLS VALO2106488 • Momentum Realty LLC, Carol A Ke...
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?
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- 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 14, 2026.
This application does not include information on all of the properties available for sale at this time.
