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
173 homes near Winchester Area
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5 rating (2 reviews)
![Trilogy® at Lake Frederic...]()
$400ks
- $900ks
Trilogy® at Lake Frederic..., Lake Frederick, VA
New and Resale
|
55+ age-restricted
|
Built 2006 - present
|
950 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
$300ks
- $500ks
The Flats at Heathcote Vi..., Haymarket, VA
New Construction
|
55+ age-restricted
|
Built 2026 - present
|
500 homes
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
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$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
$300ks
Rosehill Manor Villas, Hagerstown, MD
New Construction
|
55+ age-restricted
|
Built 2022 - present
|
177 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.
$600ks
Cadence at Lansdowne, Lansdowne, VA
Resale Only
|
55+ age-restricted
|
Built 2020 - 2024
|
74 homes
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 (3 reviews)
![Heritage Hunt]()
$400ks
- $600ks
Heritage Hunt, Gainesville, VA
Resale Only
|
55+ age-restricted
|
Built 1998 - 2009
|
1,863 homes
5 rating (1 reviews)
![Crestwood Village]()
$200ks
- $500ks
Crestwood Village, Frederick, MD
Resale Only
|
55+ age-restricted
|
Built 1979 - 1999
|
550 homes
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(540) 452-4199
$300ks
- $400ks
Winchester Landing, Winchester, VA
Resale Only
|
55+ age-restricted
|
Built 2023 - 2025
5 rating (2 reviews)
![Potomac Green]()
$400ks
- $800ks
Potomac Green, Ashburn, VA
Resale Only
|
55+ age-restricted
|
Built 2005 - 2016
|
1,400 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
$500ks
- $900ks
Montebello, Sterling, VA
New and Resale
|
55+ age-restricted
|
Built 2022 - present
|
450 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.
$800ks
- $1Ms
Lexington Square, Ashburn, VA
New Construction
|
55+ age-restricted
|
Built 2024 - present
|
23 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
$300ks
- $500ks
The Village at Foxfield, Middletown, MD
Resale Only
|
55+ age-restricted
|
Built 2003 - 2012
|
81 homes
$200ks
- $300ks
Woodbrook Village, Winchester, VA
Resale Only
|
55+ age-restricted
|
Built 1999 - 2001
|
81 homes
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$400ks
- $500ks
The Village at Harvest Ri..., Winchester, VA
Resale Only
|
55+ age-restricted
|
Built 2005 - 2016
|
82 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
5 rating (1 reviews)
![Willow Lawn Cottages]()
$300ks
Willow Lawn Cottages, Winchester, VA
Resale Only
|
55+ age-restricted
|
Built 1999 - 2004
|
120 homes
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.
$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.
$700ks
- $800ks
Regency at Creekside, Gainesville, VA
Resale Only
|
55+ age-restricted
|
Built 2016 - 2020
|
208 homes
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
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Questions? Call us:
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$400ks
Suffield Meadows, Warrenton, VA
Resale Only
|
55+ age-restricted
|
Built 2005 - 2011
|
112 homes
$400ks
- $600ks
The Highlands at Blue Rid..., Front Royal, VA
Resale Only
|
55+ age-restricted
|
Built 2017 - 2019
|
42 homes
$600ks
- $700ks
Lexington 7, Ashburn, VA
Resale Only
|
55+ age-restricted
|
Built 2017 - 2020
|
113 homes
$400ks
- $500ks
Abrams Chase, Winchester, VA
New Construction
|
55+ age-restricted
|
Built 2020 - present
|
13 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
- $700ks
Robinson Manor, Gainesville, VA
New Construction
|
55+ age-restricted
|
Built 2023 - present
|
50 homes
$100ks
- $200ks
Albert Courts, Thurmont, MD
Resale Only
|
55+ age-restricted
|
Built 1991 - 2001
|
100 homes
$300ks
- $400ks
The Signature at Broadlan..., Ashburn, VA
Resale Only
|
55+ age-restricted
|
Built 2018 - 2020
|
45 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
- $700ks
Carter's Mill, Haymarket, VA
New Construction
|
55+ age-restricted
|
Built 2020 - present
|
480 homes
Want to learn more about 55+ communities in Winchester Area?
55places can help!
Questions? Call us:
(540) 452-4199
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Questions? Call us:
(540) 452-4199
$800ks
The Retreat at Poland Hil..., Chantilly, VA
Resale Only
|
55+ age-restricted
|
Built 2020 - 2022
|
219 homes
New
CobbleStone Estates
![9724 COBBLE STONE CT 58, HAGERSTOWN, MD,..., Hagerstown, MD 21740]()
2 beds
|2 baths
|2,220 sq ft
9724 COBBLE STONE CT 58, HAGERSTOWN, MD,...
Community: CobbleStone Estates
MLS MDWA2035012 • Real Estate Innovations, Susan ...
New
Heritage Hunt
![13717 HERITAGE VALLEY WAY, GAINESVILLE, ..., Gainesville, VA 20155]()
MLS VAPW2115194 • Long & Foster Real Estate, Inc....
New
Trilogy® at Lake Frederick
![101 TROUT LILY DR, LAKE FREDERICK, VA, 2..., Lake Frederick, VA 22630]()
4 beds
|4 baths
|2,327 sq ft
101 TROUT LILY DR, LAKE FREDERICK, VA, 2...
Community: Trilogy® at Lake Frederick
MLS VAFV2040306 • Realty ONE Group Old Towne, Cha...
New
The Retreat at Poland Hill
![25612 PRESTON PARK TER, CHANTILLY, VA, 2..., Chantilly, VA 20152]()
3 beds
|3 baths
|2,410 sq ft
25612 PRESTON PARK TER, CHANTILLY, VA, 2...
Community: The Retreat at Poland Hill
MLS VALO2118082 • Keller Williams Realty, Kim V M...
New
Heritage Hunt
![13872 CRABTREE WAY, GAINESVILLE, VA, 201..., Gainesville, VA 20155]()
MLS VAPW2115142 • CENTURY 21 New Millennium, Jame...
Want to learn more about 55+ communities in Winchester Area?
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Questions? Call us:
(540) 452-4199
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Questions? Call us:
(540) 452-4199
New
Emerald Pointe
![13301 MARQUISE DR, HAGERSTOWN, MD, 21742, Hagerstown, MD 21742]()
MLS MDWA2035092 • Real Estate Innovations, Deanne...
New
Trilogy® at Lake Frederick
![105 CABBAGE WHITE DR, LAKE FREDERICK, VA..., Lake Frederick, VA 22630]()
3 beds
|4 baths
|2,910 sq ft
105 CABBAGE WHITE DR, LAKE FREDERICK, VA...
Community: Trilogy® at Lake Frederick
MLS VAFV2040334 • EXP Realty, LLC, Thu-Nguyet Thi...
New
Cedar Meadows
![108 TRUMPET VINE DR, WHITE POST, VA, 226..., White Post, VA 22663]()
MLS VAFV2040260 • ERA Oakcrest Realty, Inc., Tiff...
The Highlands at Blue Ridge Shadows
![18 ALBATROSS CT, FRONT ROYAL, VA, 22630, Front Royal, VA 22630]()
4 beds
|4 baths
|3,861 sq ft
18 ALBATROSS CT, FRONT ROYAL, VA, 22630
Community: The Highlands at Blue Ridge Shadows
MLS VAWR2013600 • Samson Properties, Nancy M Poe
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.
Winchester Landing
![101 MAURY, WINCHESTER, VA, 22602, Winchester, VA 22602]()
MLS VAFV2040248 • National Realty, LLC, Anita R H...
The Village at Freedom Hills
![13862 PATRIOT WAY, HAGERSTOWN, MD, 21740, Hagerstown, MD 21740]()
4 beds
|2 baths
|3,107 sq ft
13862 PATRIOT WAY, HAGERSTOWN, MD, 21740
Community: The Village at Freedom Hills
MLS MDWA2035014 • LPT Realty, LLC, Gemma Corley
The Woodlands of Urbana
![3422 ANGELICA WAY 103, FREDERICK, MD, 21..., Frederick, MD 21704]()
2 beds
|2 baths
|Condo
3422 ANGELICA WAY 103, FREDERICK, MD, 21...
Community: The Woodlands of Urbana
MLS MDFR2076526 • Northrop Realty, Richard Philli...
Rosehill Manor Villas
![19601 LAVENDER LN, HAGERSTOWN, MD, 21742, Hagerstown, MD 21742]()
2 beds
|2 baths
|1,735 sq ft
19601 LAVENDER LN, HAGERSTOWN, MD, 21742
Community: Rosehill Manor Villas
MLS MDWA2035004 • Taylor Properties, Joseph P How...
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(540) 452-4199
Birchwood at Brambleton
![43059 GREELEY SQ, ASHBURN, VA, 20148, Ashburn, VA 20148]()
3 beds
|3 baths
|2,570 sq ft
43059 GREELEY SQ, ASHBURN, VA, 20148
Community: Birchwood at Brambleton
MLS VALO2118380 • M.O. Wilson Properties, Wes W. ...
Lansdowne Woods of Virginia
![19365 CYPRESS RIDGE TER 510, LEESBURG, V..., Leesburg, VA 20176]()
2 beds
|2 baths
|1,251 sq ft
|Condo
19365 CYPRESS RIDGE TER 510, LEESBURG, V...
Community: Lansdowne Woods of Virginia
MLS VALO2117946 • Compass, Karen A Miller
Cadence at Lansdowne
![43887 SIREN SONG TER, LEESBURG, VA, 2017..., Leesburg, VA 20176]()
4 beds
|4 baths
|2,642 sq ft
43887 SIREN SONG TER, LEESBURG, VA, 2017...
Community: Cadence at Lansdowne
MLS VALO2116906 • Bruck Realty, Deborah L Bruck
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Cadence at Lansdowne
![19006 CORAL REEF SQ, LEESBURG, VA, 20176, Leesburg, VA 20176]()
3 beds
|5 baths
|3,679 sq ft
19006 CORAL REEF SQ, LEESBURG, VA, 20176
Community: Cadence at Lansdowne
MLS VALO2118090 • Hunt Country Sotheby's Internat...
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.
Gatherings at Wellington
![9200 CHARLESTON DR 404, MANASSAS, VA, 20..., Manassas, VA 20110]()
2 beds
|2 baths
|1,504 sq ft
|Condo
9200 CHARLESTON DR 404, MANASSAS, VA, 20...
Community: Gatherings at Wellington
MLS VAMN2010404 • Weichert, REALTORS, Mary Ann Be...
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.
Montebello
![46337 REDDISH KNOB DR, STERLING, VA, 201..., Sterling, VA 20164]()
MLS VALO2118128 • TTR Sotheby's International Rea...
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 MDFR2078152 • Compass, Ross J Wilhelm
Trilogy® at Lake Frederick
![107 CABBAGE WHITE DR, LAKE FREDERICK, VA..., Lake Frederick, VA 22630]()
4 beds
|4 baths
|3,190 sq ft
107 CABBAGE WHITE DR, LAKE FREDERICK, VA...
Community: Trilogy® at Lake Frederick
MLS VAFV2040122 • Slones Real Estate, Theodore Lo...
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Regency at Creekside
![13712 LONG RIDGE DR, GAINESVILLE, VA, 20..., Gainesville, VA 20155]()
3 beds
|3 baths
|3,146 sq ft
13712 LONG RIDGE DR, GAINESVILLE, VA, 20...
Community: Regency at Creekside
MLS VAPW2114396 • EXP Realty, LLC, Barbara Y Blum...
Suffield Meadows
![6696 CLUB HOUSE LN 104, WARRENTON, VA, 2..., Warrenton, VA 20187]()
3 beds
|2 baths
|1,994 sq ft
|Condo
6696 CLUB HOUSE LN 104, WARRENTON, VA, 2...
Community: Suffield Meadows
MLS VAFQ2020064 • Long & Foster, Kristy M Odendha...
Regency at Dominion Valley
![15564 LEGACY WAY, HAYMARKET, VA, 20169, Haymarket, VA 20169]()
3 beds
|3 baths
|4,059 sq ft
15564 LEGACY WAY, HAYMARKET, VA, 20169
Community: Regency at Dominion Valley
MLS VAPW2114304 • Keller Williams Realty, Kimberl...
Trilogy® at Lake Frederick
![106 RHODODENDRON CT, LAKE FREDERICK, VA,..., Lake Frederick, VA 22630]()
2 beds
|2 baths
|2,058 sq ft
106 RHODODENDRON CT, LAKE FREDERICK, VA,...
Community: Trilogy® at Lake Frederick
MLS VAFV2040094 • Keller Williams Realty, Matt Bo...
Trilogy® at Lake Frederick
![110 RHODODENDRON CT, LAKE FREDERICK, VA,..., Lake Frederick, VA 22630]()
3 beds
|3 baths
|3,725 sq ft
110 RHODODENDRON CT, LAKE FREDERICK, VA,...
Community: Trilogy® at Lake Frederick
MLS VAFV2040092 • 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.
The Village at Freedom Hills
![13880 PATRIOT WAY, HAGERSTOWN, MD, 21740, Hagerstown, MD 21740]()
2 beds
|2 baths
|1,543 sq ft
13880 PATRIOT WAY, HAGERSTOWN, MD, 21740
Community: The Village at Freedom Hills
MLS MDWA2034802 • RE/MAX Results, Shirley J Bayer
Want to learn more about 55+ rental communities in Winchester Area?
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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.
Trilogy® at Lake Frederick
![103 CLOAK LN, LAKE FREDERICK, VA, 22630, Lake Frederick, VA 22630]()
3 beds
|3 baths
|2,486 sq ft
103 CLOAK LN, LAKE FREDERICK, VA, 22630
Community: Trilogy® at Lake Frederick
MLS VAFV2040080 • LPT Realty, LLC, Matthew Lama
Willow Lawn Cottages
![1851 MELVOR LN, WINCHESTER, VA, 22601, Winchester, VA 22601]()
2 beds
|2 baths
|1,405 sq ft
1851 MELVOR LN, WINCHESTER, VA, 22601
Community: Willow Lawn Cottages
MLS VAWI2010102 • RE/MAX Roots, Roxanna D Grimes
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Lansdowne Woods of Virginia
![19365 CYPRESS RIDGE TER 1115, LEESBURG, ..., Leesburg, VA 20176]()
3 beds
|2 baths
|1,475 sq ft
|Condo
19365 CYPRESS RIDGE TER 1115, LEESBURG, ...
Community: Lansdowne Woods of Virginia
MLS VALO2117564 • Compass, Karen A Miller
Potomac Green
![44438 CRUDEN BAY DR, ASHBURN, VA, 20147, Ashburn, VA 20147]()
MLS VALO2117718 • Samson Properties, John C Goodw...
Bloomfields 55+
![2605 BROADLEAF DR, FREDERICK, MD, 21702, Frederick, MD 21702]()
MLS MDFR2077744 • Keller Williams Realty Centre, ...
Regency at Dominion Valley
![15517 LEGACY WAY, HAYMARKET, VA, 20169, Haymarket, VA 20169]()
3 beds
|3 baths
|3,056 sq ft
15517 LEGACY WAY, HAYMARKET, VA, 20169
Community: Regency at Dominion Valley
MLS VAPW2113424 • CENTURY 21 New Millennium, Patr...
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.
Gatherings at Wellington
![9202 CHARLESTON DR 405, MANASSAS, VA, 20..., Manassas, VA 20110]()
2 beds
|2 baths
|1,504 sq ft
|Condo
9202 CHARLESTON DR 405, MANASSAS, VA, 20...
Community: Gatherings at Wellington
MLS VAMN2010366 • M.O. Wilson Properties, Staci M...
Crestwood Village
![5798 BOX ELDER CT, FREDERICK, MD, 21703, Frederick, MD 21703]()
MLS MDFR2078092 • Tyler Duncan Realty Partners, I...
Birchwood at Brambleton
![23716 SEPTEMBER SUN SQ, ASHBURN, VA, 201..., Ashburn, VA 20148]()
3 beds
|3 baths
|2,258 sq ft
23716 SEPTEMBER SUN SQ, ASHBURN, VA, 201...
Community: Birchwood at Brambleton
MLS VALO2117684 • Century 21 Redwood Realty, AnaM...
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.
The Village at Harvest Ridge
![153 HARVEST RIDGE DR, WINCHESTER, VA, 22..., Winchester, VA 22601]()
4 beds
|3 baths
|3,157 sq ft
153 HARVEST RIDGE DR, WINCHESTER, VA, 22...
Community: The Village at Harvest Ridge
MLS VAFV2040020 • Homecoin.com, Jonathan Minerick
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Lansdowne Woods of Virginia
![19385 CYPRESS RIDGE TER 510, LEESBURG, V..., Leesburg, VA 20176]()
3 beds
|2 baths
|1,475 sq ft
|Condo
19385 CYPRESS RIDGE TER 510, LEESBURG, V...
Community: Lansdowne Woods of Virginia
MLS VALO2117644 • Long & Foster Real Estate, Inc....
Birchwood at Brambleton
![23669 GOLDEN EMBERS SQ 204, ASHBURN, VA,..., Ashburn, VA 20148]()
2 beds
|2 baths
|1,280 sq ft
|Condo
23669 GOLDEN EMBERS SQ 204, ASHBURN, VA,...
Community: Birchwood at Brambleton
MLS VALO2117556 • Pearson Smith Realty, LLC, Jenn...
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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REIN updates its listings on a daily basis. Data last updated: Mar 25, 2026.
This application does not include information on all of the properties available for sale at this time.
