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
141 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
Want to learn more about 55+ communities in Winchester Area?
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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]()
$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
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5 rating (1 reviews)
![Regency at Dominion Valle...]()
$400Ks
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
- $500Ks
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
- $400Ks
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
$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
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.
$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
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
Want to learn more about 55+ communities in Winchester Area?
55places can help!
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
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...
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...
Woodbrook Village
![203 CRESTWOOD LN, WINCHESTER, VA, 22602, Winchester, VA 22602]()
MLS VAFV2038228 • MarketPlace REALTY, Jen Richard...
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Questions? Call us:
(540) 452-4199
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Questions? Call us:
(540) 452-4199
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
Potomac Green
![44420 SUNSET MAPLE DR, ASHBURN, VA, 2014..., Ashburn, VA 20147]()
MLS VALO2111136 • Samson Properties, Anne Elaine ...
New
Trilogy® at Lake Frederick
![109 TUTELO LN, LAKE FREDERICK, VA, 22630, Lake Frederick, VA 22630]()
2 beds
|3 baths
|3,505 sq ft
109 TUTELO LN, LAKE FREDERICK, VA, 22630
Community: Trilogy® at Lake Frederick
MLS VAFV2038762 • Keller Williams Realty, Matt Bo...
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
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.
Potomac Green
![44452 OAKMONT MANOR SQ, ASHBURN, VA, 201..., Ashburn, VA 20147]()
MLS VALO2114250 • Samson Properties, Tammy L Irby
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...
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...
Regency at Creekside
![5934 BOWES CREEK PL, GAINESVILLE, VA, 20..., Gainesville, VA 20155]()
4 beds
|5 baths
|4,873 sq ft
5934 BOWES CREEK PL, GAINESVILLE, VA, 20...
Community: Regency at Creekside
MLS VAPW2110806 • Long & Foster Real Estate, Inc....
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Potomac Green
![44529 BLUERIDGE MEADOWS DR, ASHBURN, VA,..., Ashburn, VA 20147]()
MLS VALO2109410 • Weichert, REALTORS, Cecil R Fra...
Gatherings at Potomac Station
![750 MOUNT AIRY TER NE UNIT 403, LEESBURG..., Leesburg, VA 20176]()
2 beds
|2 baths
|1,410 sq ft
|Condo
750 MOUNT AIRY TER NE UNIT 403, LEESBURG...
Community: Gatherings at Potomac Station
MLS VALO2112922 • Pearson Smith Realty, LLC, Vick...
New
Lexington 7
![44490 COALPORT TER, ASHBURN, VA, 20147, Ashburn, VA 20147]()
MLS VALO2114672 • RE/MAX Galaxy, Kanwal R Chaudry
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New
Lexington Square
![44490 COALPORT TER, ASHBURN, VA, 20147, Ashburn, VA 20147]()
MLS VALO2114672 • RE/MAX Galaxy, Kanwal R Chaudry
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
![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...
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.
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
![6029 CALUMET CT, GAINESVILLE, VA, 20155, Gainesville, VA 20155]()
MLS VAPW2111028 • RLAH @properties, Candace Moe
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...
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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
![6331 AVINGTON PL, GAINESVILLE, VA, 20155, Gainesville, VA 20155]()
MLS VAPW2110704 • Long & Foster Real Estate, Inc....
Cross Creek Village
![202 BUTTERSCOTCH CT, WINCHESTER, VA, 226..., Winchester, VA 22602]()
3 beds
|3 baths
|3,207 sq ft
202 BUTTERSCOTCH CT, WINCHESTER, VA, 226...
Community: Cross Creek Village
MLS VAFV2038036 • MarketPlace REALTY, Elizabeth P...
Heritage Hunt
![13612 RYTON RIDGE LN, GAINESVILLE, VA, 2..., Gainesville, VA 20155]()
MLS VAPW2107150 • RE/MAX Gateway, Fawn Deitsch
Lexington 7
![19873 SILVERY BLUE TER, ASHBURN, VA, 201..., Ashburn, VA 20147]()
MLS VALO2106488 • Momentum Realty LLC, Carol A Ke...
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
![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...
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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.
New
Heritage Hunt
![13141 TRIPLE CROWN LOOP, GAINESVILLE, VA..., Gainesville, VA 20155]()
MLS VAPW2111130 • Pearson Smith Realty LLC, Amber...
Liberty Grove
![8600 LIBERTY TRL 102, MANASSAS, VA, 2011..., Manassas, VA 20110]()
1 beds
|2 baths
|1,131 sq ft
|Condo
8600 LIBERTY TRL 102, MANASSAS, VA, 2011...
Community: Liberty Grove
MLS VAMN2009948 • Long & Foster Real Estate, Inc....
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New
Birchwood at Brambleton
![23630 HAVELOCK WALK TER UNIT 305, ASHBUR..., Ashburn, VA 20148]()
2 beds
|2 baths
|1,060 sq ft
|Condo
23630 HAVELOCK WALK TER UNIT 305, ASHBUR...
Community: Birchwood at Brambleton
MLS VALO2114614 • EXP Realty, LLC, Katherine D He...
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...
New
Heritage Hunt
![17680 GLASS RIDGE PL, GAINESVILLE, VA, 2..., Gainesville, VA 20155]()
MLS VAPW2111214 • Berkshire Hathaway HomeServices...
Lexington 7
![44510 LOWESTOFT SQ, ASHBURN, VA, 20147, Ashburn, VA 20147]()
MLS VALO2113864 • Real Broker, LLC, John Young Jo...
Lexington Square
![44510 LOWESTOFT SQ, ASHBURN, VA, 20147, Ashburn, VA 20147]()
MLS VALO2113864 • Real Broker, LLC, John Young Jo...
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
![124 PIMPERNEL PL, LAKE FREDERICK, VA, 22..., Lake Frederick, VA 22630]()
3 beds
|4 baths
|3,768 sq ft
124 PIMPERNEL PL, LAKE FREDERICK, VA, 22...
Community: Trilogy® at Lake Frederick
MLS VAFV2039024 • HomeZu.com of Virginia, Jason P...
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 ...
Potomac Green
![44482 MALTESE FALCON SQ, ASHBURN, VA, 20..., Ashburn, VA 20147]()
MLS VALO2113734 • Long & Foster Real Estate, Inc....
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.
New
Winchester Landing
![116 MAURY WAY, WINCHESTER, VA, 22602, Winchester, VA 22602]()
MLS VAFV2039208 • Nova Home Hunters Realty, Amand...
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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...
Lansdowne Woods of Virginia
![19375 CYPRESS RIDGE TER 114, LEESBURG, V..., Leesburg, VA 20176]()
2 beds
|2 baths
|1,446 sq ft
|Condo
19375 CYPRESS RIDGE TER 114, LEESBURG, V...
Community: Lansdowne Woods of Virginia
MLS VALO2114234 • Compass, Karen A Miller
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
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- Answers from local 55+ experts
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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 28, 2026.
This application does not include information on all of the properties available for sale at this time.
