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
199 homes near Winchester Area
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5 rating (2 reviews)
![Trilogy® at Lake Frederic...]()
- $900ks
Trilogy® at Lake Frederic..., Lake Frederick, VA
New and Resale
|
55+ age-restricted
|
Built 2006 - present
|
950 homes
$300ks
- $500ks
The Flats at Heathcote Vi..., Haymarket, VA
New Construction
|
55+ age-restricted
|
Built 2026 - present
|
500 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
5 rating (3 reviews)
![Heritage Hunt]()
$400ks
- $600ks
Heritage Hunt, Gainesville, VA
Resale Only
|
55+ age-restricted
|
Built 1998 - 2009
|
1,863 homes
Want to learn more about 55+ communities in Winchester Area?
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(540) 452-4199
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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
$300ks
- $500ks
Emerald Pointe, Hagerstown, MD
New and Resale
|
55+ age-restricted
|
Built 2008 - present
|
250 homes
$700ks
- $800ks
Bloomfields 55+, Frederick, MD
New Construction
|
55+ age-restricted
|
Built 2026 - present
$500ks
- $700ks
The Woodlands of Urbana, Urbana, MD
Resale Only
|
55+ age-restricted
|
Built 2019 - 2025
|
565 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.
5 rating (1 reviews)
![Gatherings at Wellington]()
$300ks
- $400ks
Gatherings at Wellington, Manassas, VA
Resale Only
|
55+ age-restricted
|
Built 2011 - 2016
|
135 homes
5 rating (2 reviews)
![Potomac Green]()
$400ks
- $800ks
Potomac Green, Ashburn, VA
Resale Only
|
55+ age-restricted
|
Built 2005 - 2016
|
1,400 homes
$300ks
Rosehill Manor Villas, Hagerstown, MD
New Construction
|
55+ age-restricted
|
Built 2022 - present
|
177 homes
$300ks
The Village at Freedom Hi..., Hagerstown, MD
New and Resale
|
55+ age-restricted
|
Built 2007 - present
|
66 homes
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(540) 452-4199
$600ks
Cadence at Lansdowne, Lansdowne, VA
Resale Only
|
55+ age-restricted
|
Built 2020 - 2024
|
74 homes
5 rating (1 reviews)
![Crestwood Village]()
$200ks
- $500ks
Crestwood Village, Frederick, MD
Resale Only
|
55+ age-restricted
|
Built 1979 - 1999
|
550 homes
$500ks
- $900ks
Montebello, Sterling, VA
New and Resale
|
55+ age-restricted
|
Built 2022 - present
|
450 homes
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(540) 452-4199
3 rating (2 reviews)
![Dunbarton]()
$300ks
- $500ks
Dunbarton, Bristow, VA
Resale Only
|
55+ age-restricted
|
Built 2000 - 2009
|
479 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.
$300ks
- $400ks
Winchester Landing, Winchester, VA
Resale Only
|
55+ age-restricted
|
Built 2023 - 2025
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.
$800ks
- $1Ms
Lexington Square, Ashburn, VA
New Construction
|
55+ age-restricted
|
Built 2024 - present
|
23 homes
$200ks
- $300ks
Woodbrook Village, Winchester, VA
Resale Only
|
55+ age-restricted
|
Built 1999 - 2001
|
81 homes
$400ks
- $500ks
The Village at Harvest Ri..., Winchester, VA
Resale Only
|
55+ age-restricted
|
Built 2005 - 2016
|
82 homes
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Questions? Call us:
(540) 452-4199
$300ks
Cross Creek Village, Winchester, VA
Resale Only
|
55+ age-restricted
|
Built 2001 - 2004
|
90 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
$300ks
- $400ks
Cedar Meadows, White Post, VA
Resale Only
|
55+ age-restricted
|
Built 2010 - 2022
|
129 homes
$300ks
- $800ks
Regency at Ashburn, Ashburn, VA
Resale Only
|
55+ age-restricted
|
Built 2013 - 2020
|
268 homes
5 rating (1 reviews)
![Willow Lawn Cottages]()
$300ks
Willow Lawn Cottages, Winchester, VA
Resale Only
|
55+ age-restricted
|
Built 1999 - 2004
|
120 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.
$200ks
- $300ks
Liberty Grove, Manassas, VA
Resale Only
|
55+ age-restricted
|
Built 2005 - 2005
|
61 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.
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
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
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Questions? Call us:
(540) 452-4199
$600ks
- $700ks
Lexington 7, Ashburn, VA
Resale Only
|
55+ age-restricted
|
Built 2017 - 2020
|
113 homes
$800ks
The Retreat at Poland Hil..., Chantilly, VA
Resale Only
|
55+ age-restricted
|
Built 2020 - 2022
|
219 homes
$400ks
- $500ks
Abrams Chase, Winchester, VA
New Construction
|
55+ age-restricted
|
Built 2020 - present
|
13 homes
$600ks
- $700ks
Robinson Manor, Gainesville, VA
New Construction
|
55+ age-restricted
|
Built 2023 - present
|
50 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.
$600ks
- $900ks
Regency at Belmont, Ashburn, VA
New Construction
|
55+ age-restricted
|
Built 2021 - present
|
145 homes
$300ks
- $400ks
JerMae Estates, Thurmont, MD
Resale Only
|
55+ age-restricted
|
Built 2003 - 2008
|
108 homes
$400ks
- $700ks
Carter's Mill, Haymarket, VA
New Construction
|
55+ age-restricted
|
Built 2020 - present
|
480 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.
$400ks
- $500ks
CobbleStone Estates, Hagerstown, MD
New and Resale
|
55+ age-restricted
|
Built 2015 - present
|
66 homes
Want to learn more about 55+ communities in Winchester Area?
55places can help!
Questions? Call us:
(540) 452-4199
Want to learn more about 55+ rental communities in Winchester Area?
55places can help!
Questions? Call us:
(540) 452-4199
$500ks
- $600ks
Boxwood Villas, Urbana, MD
Resale Only
|
55+ age-restricted
|
Built 2019 - 2021
|
92 homes
New
Crestwood Village
![5738 BOX ELDER CT, FREDERICK, MD, 21703, Frederick, MD 21703]()
MLS MDFR2079412 • Bach Real Estate, Sharon A Olan...
New
Heritage Hunt
![13891 CHELMSFORD DR, GAINESVILLE, VA, 20..., Gainesville, VA 20155]()
3 beds
|2 baths
|1,424 sq ft
|Condo
13891 CHELMSFORD DR, GAINESVILLE, VA, 20...
Community: Heritage Hunt
MLS VAPW2115642 • CENTURY 21 New Millennium, Star...
New
Cedar Meadows
![103 BLEEDING HEART DR, WHITE POST, VA, 2..., White Post, VA 22663]()
MLS VAFV2039392 • Dandridge Realty Group, LLC, Ro...
New
Heritage Hunt
![6828 DERBY RUN WAY, GAINESVILLE, VA, 201..., Gainesville, VA 20155]()
MLS VAPW2114834 • Samson Properties, Tricia Leigh...
New
The Woodlands of Urbana
![3234 STARLIGHT ST, FREDERICK, MD, 21704, Frederick, MD 21704]()
3 beds
|4 baths
|2,276 sq ft
3234 STARLIGHT ST, FREDERICK, MD, 21704
Community: The Woodlands of Urbana
MLS MDFR2079804 • Long & Foster Real Estate, Inc....
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Questions? Call us:
(540) 452-4199
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55places can help!
Questions? Call us:
(540) 452-4199
New
Potomac Green
![44348 SUNSET MAPLE DR, ASHBURN, VA, 2014..., Ashburn, VA 20147]()
MLS VALO2119758 • Samson Properties, Andrea M. Ha...
New
Potomac Green
![44345 SUNSET MAPLE DR, ASHBURN, VA, 2014..., Ashburn, VA 20147]()
MLS VALO2115746 • Samson Properties, Andrea M. Ha...
New
The Village at Harvest Ridge
![126 HARVEST RIDGE DR, WINCHESTER, VA, 22..., Winchester, VA 22601]()
3 beds
|2 baths
|2,834 sq ft
126 HARVEST RIDGE DR, WINCHESTER, VA, 22...
Community: The Village at Harvest Ridge
MLS VAFV2040774 • Long & Foster Real Estate, Inc....
New
Trilogy® at Lake Frederick
![104 GROSBEAK CT, LAKE FREDERICK, VA, 226..., Lake Frederick, VA 22630]()
3 beds
|3 baths
|2,933 sq ft
104 GROSBEAK CT, LAKE FREDERICK, VA, 226...
Community: Trilogy® at Lake Frederick
MLS VAFV2039340 • Keller Williams Realty, Matt Bo...
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.
New
CobbleStone Estates
![9723 COBBLE STONE CT, HAGERSTOWN, MD, 21..., Hagerstown, MD 21740]()
2 beds
|2 baths
|1,828 sq ft
9723 COBBLE STONE CT, HAGERSTOWN, MD, 21...
Community: CobbleStone Estates
MLS MDWA2035426 • Real Estate Innovations, Susan ...
New
Heritage Hunt
![13520 NORWICK PL, GAINESVILLE, VA, 20155, Gainesville, VA 20155]()
MLS VAPW2111482 • Samson Properties, Natalie H Mc...
New
The Woodlands of Urbana
![3225 THORNAPPLE DR, FREDERICK, MD, 21704, Frederick, MD 21704]()
3 beds
|3 baths
|1,816 sq ft
3225 THORNAPPLE DR, FREDERICK, MD, 21704
Community: The Woodlands of Urbana
MLS MDFR2079850 • IMPACT Maryland Real Estate, St...
New
Heritage Hunt
![6852 TRED AVON PL, GAINESVILLE, VA, 2015..., Gainesville, VA 20155]()
MLS VAPW2115964 • Keller Williams Realty Advantag...
Want to learn more about 55+ communities in Winchester Area?
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(540) 452-4199
New
Potomac Green
![20598 CRESCENT POINTE PL, ASHBURN, VA, 2..., Ashburn, VA 20147]()
MLS VALO2120322 • Long & Foster Real Estate, Inc....
New
The Highlands at Blue Ridge Shadows
![48 HICKORY SHAFT CT, FRONT ROYAL, VA, 22..., Front Royal, VA 22630]()
3 beds
|2 baths
|1,763 sq ft
48 HICKORY SHAFT CT, FRONT ROYAL, VA, 22...
Community: The Highlands at Blue Ridge Shadows
MLS VAWR2013914 • Keller Williams Realty, Alicia ...
New
Ballenger Run
![6443 AUTUMN OLIVE DR, FREDERICK, MD, 217..., Frederick, MD 21703]()
MLS MDFR2079720 • RE/MAX Results, Sue P Collins
Want to learn more about 55+ rental communities in Winchester Area?
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(540) 452-4199
New
Lansdowne Woods of Virginia
![19355 CYPRESS RIDGE TER 219, LEESBURG, V..., Leesburg, VA 20176]()
2 beds
|2 baths
|1,500 sq ft
|Condo
19355 CYPRESS RIDGE TER 219, LEESBURG, V...
Community: Lansdowne Woods of Virginia
MLS VALO2119234 • Compass, Karen A Miller
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.
New
Heritage Hunt
![13700 FIELDSTONE WAY, GAINESVILLE, VA, 2..., Gainesville, VA 20155]()
MLS VAPW2114682 • Pearson Smith Realty, LLC, Cher...
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
Lansdowne Woods of Virginia
![19350 MAGNOLIA GROVE SQ 403, LEESBURG, V..., Leesburg, VA 20176]()
2 beds
|2 baths
|1,168 sq ft
|Condo
19350 MAGNOLIA GROVE SQ 403, LEESBURG, V...
Community: Lansdowne Woods of Virginia
MLS VALO2120272 • Keller Williams Realty, Suzanne...
New
Birchwood at Brambleton
![42920 FIREFLY SONATA TER 203, ASHBURN, V..., Ashburn, VA 20148]()
3 beds
|2 baths
|1,712 sq ft
|Condo
42920 FIREFLY SONATA TER 203, ASHBURN, V...
Community: Birchwood at Brambleton
MLS VALO2120184 • Samson Properties, Meg Elizabet...
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New
Lansdowne Woods of Virginia
![19375 CYPRESS RIDGE TER 1111, LEESBURG, ..., Leesburg, VA 20176]()
3 beds
|2 baths
|1,475 sq ft
|Condo
19375 CYPRESS RIDGE TER 1111, LEESBURG, ...
Community: Lansdowne Woods of Virginia
MLS VALO2116242 • Samson Properties, Andrew M Nor...
New
Trilogy® at Lake Frederick
![104 RHODODENDRON CT, LAKE FREDERICK, VA,..., Lake Frederick, VA 22630]()
3 beds
|3 baths
|2,457 sq ft
104 RHODODENDRON CT, LAKE FREDERICK, VA,...
Community: Trilogy® at Lake Frederick
MLS VAFV2040680 • Keller Williams Realty, Matt Bo...
Liberty Grove
![8610 LIBERTY TRL 305, MANASSAS, VA, 2011..., Manassas, VA 20110]()
2 beds
|3 baths
|1,518 sq ft
|Condo
8610 LIBERTY TRL 305, MANASSAS, VA, 2011...
Community: Liberty Grove
MLS VAMN2010576 • Keller Williams Realty, Jennife...
Vistas at Lansdowne
![19400 LANSDOWNE WOODS BLVD 101, LEESBURG..., Leesburg, VA 20176]()
2 beds
|2 baths
|2,041 sq ft
|Condo
19400 LANSDOWNE WOODS BLVD 101, LEESBURG...
Community: Vistas at Lansdowne
MLS VALO2120042 • Samson Properties, Phyllis Ann ...
Trilogy® at Lake Frederick
![121 MILKWEED, LAKE FREDERICK, VA, 22630, Lake Frederick, VA 22630]()
3 beds
|4 baths
|4,213 sq ft
121 MILKWEED, LAKE FREDERICK, VA, 22630
Community: Trilogy® at Lake Frederick
MLS VAFV2040638 • Samson Properties, Yvonne R Hol...
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
![23608 HAVELOCK WALK TER, ASHBURN, VA, 20..., Ashburn, VA 20148]()
3 beds
|3 baths
|2,516 sq ft
|Condo
23608 HAVELOCK WALK TER, ASHBURN, VA, 20...
Community: Birchwood at Brambleton
MLS VALO2120138 • RE/MAX Real Estate Connections,...
Want to learn more about 55+ rental communities in Winchester Area?
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(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.
Regency at Ashburn
![44589 YORK CREST TER 300, ASHBURN, VA, 2..., Ashburn, VA 20147]()
3 beds
|2 baths
|1,886 sq ft
|Condo
44589 YORK CREST TER 300, ASHBURN, VA, 2...
Community: Regency at Ashburn
MLS VALO2115658 • Redfin Corporation, Allison Wel...
Heritage Hunt
![6318 RETRIEVER LN, GAINESVILLE, VA, 2015..., Gainesville, VA 20155]()
MLS VAPW2110890 • Samson Properties, Natalie H Mc...
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Trilogy® at Lake Frederick
![213 GREBE DR, LAKE FREDERICK, VA, 22630, Lake Frederick, VA 22630]()
3 beds
|4 baths
|3,191 sq ft
213 GREBE DR, LAKE FREDERICK, VA, 22630
Community: Trilogy® at Lake Frederick
MLS VAFV2040610 • Keller Williams Realty, Kim E Y...
Trilogy® at Lake Frederick
![110 COTTONTAIL DR, LAKE FREDERICK, VA, 2..., Lake Frederick, VA 22630]()
3 beds
|3 baths
|2,860 sq ft
110 COTTONTAIL DR, LAKE FREDERICK, VA, 2...
Community: Trilogy® at Lake Frederick
MLS VAFV2040546 • Keller Williams Realty, Sarah A...
Trilogy® at Lake Frederick
![311 GREBE DR, LAKE FREDERICK, VA, 22630, Lake Frederick, VA 22630]()
3 beds
|3 baths
|4,629 sq ft
311 GREBE DR, LAKE FREDERICK, VA, 22630
Community: Trilogy® at Lake Frederick
MLS VAFV2040486 • CENTURY 21 New Millennium, Jenn...
Heritage Hunt
![6938 WALNUT HILL DR, GAINESVILLE, VA, 20..., Gainesville, VA 20155]()
MLS VAPW2115794 • Corcoran McEnearney, Margarita ...
Heritage Hunt
![13703 CURRANT LOOP, GAINESVILLE, VA, 201..., Gainesville, VA 20155]()
MLS VAPW2115790 • Samson Properties, Tricia Leigh...
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.
Willow Run
![232 HYDRANGEA WAY, WINCHESTER, VA, 22602, Winchester, VA 22602]()
MLS VAFV2040526 • D R Horton Realty of Virginia L...
Willow Run
![234 HYDRANGEA WAY, WINCHESTER, VA, 22602, Winchester, VA 22602]()
MLS VAFV2040524 • D R Horton Realty of Virginia L...
Willow Run
![249 HYDRANGEA WAY, WINCHESTER, VA, 22602, Winchester, VA 22602]()
MLS VAFV2040518 • 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
![116 TRELLIS VIEW LN, WINCHESTER, VA, 226..., Winchester, VA 22602]()
MLS VAFV2040516 • D R Horton Realty of Virginia L...
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(540) 452-4199
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Willow Run
![125 TRELLIS VIEW LN, WINCHESTER, VA, 226..., Winchester, VA 22602]()
MLS VAFV2040514 • D R Horton Realty of Virginia L...
Willow Run
![120 TRELLIS VIEW LN, WINCHESTER, VA, 226..., Winchester, VA 22602]()
MLS VAFV2040510 • 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?
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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: Apr 10, 2026.
This application does not include information on all of the properties available for sale at this time.
