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
214 homes near Winchester Area
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5 rating (2 reviews)
![Trilogy® at Lake Frederic...]()
$300ks
- $1Ms
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
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
5 rating (3 reviews)
![Heritage Hunt]()
$400ks
- $600ks
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
- $1Ms
Birchwood at Brambleton, Ashburn, VA
New and Resale
|
55+ age-restricted
|
Built 2016 - present
|
1,502 homes
$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
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55+ age-restricted
|
Built 2022 - present
|
177 homes
$300ks
- $500ks
Emerald Pointe, Hagerstown, MD
New and Resale
|
55+ age-restricted
|
Built 2008 - present
|
250 homes
$600ks
Cadence at Lansdowne, Lansdowne, VA
Resale Only
|
55+ age-restricted
|
Built 2020 - 2024
|
74 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.
$700ks
- $800ks
Bloomfields 55+, Frederick, MD
New Construction
|
55+ age-restricted
|
Built 2026 - present
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
3 rating (2 reviews)
![Dunbarton]()
$300ks
- $500ks
Dunbarton, Bristow, VA
Resale Only
|
55+ age-restricted
|
Built 2000 - 2009
|
479 homes
5 rating (1 reviews)
![Crestwood Village]()
$200ks
- $500ks
Crestwood Village, Frederick, MD
Resale Only
|
55+ age-restricted
|
Built 1979 - 1999
|
550 homes
$300ks
- $500ks
The Village at Foxfield, Middletown, MD
Resale Only
|
55+ age-restricted
|
Built 2003 - 2012
|
81 homes
5 rating (2 reviews)
![Potomac Green]()
$400ks
- $800ks
Potomac Green, Ashburn, VA
Resale Only
|
55+ age-restricted
|
Built 2005 - 2016
|
1,400 homes
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5 rating (1 reviews)
![Willow Lawn Cottages]()
$300ks
Willow Lawn Cottages, Winchester, VA
Resale Only
|
55+ age-restricted
|
Built 1999 - 2004
|
120 homes
$500ks
- $1Ms
Montebello, Sterling, VA
New and Resale
|
55+ age-restricted
|
Built 2022 - present
|
450 homes
$300ks
- $400ks
Winchester Landing, Winchester, VA
Resale Only
|
55+ age-restricted
|
Built 2023 - 2025
$600ks
- $900ks
Regency at Belmont, Ashburn, VA
New Construction
|
55+ age-restricted
|
Built 2021 - present
|
145 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
The Village at Freedom Hi..., Hagerstown, MD
New and Resale
|
55+ age-restricted
|
Built 2007 - present
|
66 homes
$300ks
- $400ks
Cedar Meadows, White Post, VA
Resale Only
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55+ age-restricted
|
Built 2010 - 2022
|
129 homes
$200ks
- $300ks
Liberty Grove, Manassas, VA
Resale Only
|
55+ age-restricted
|
Built 2005 - 2005
|
61 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
$400ks
Suffield Meadows, Warrenton, VA
Resale Only
|
55+ age-restricted
|
Built 2005 - 2011
|
112 homes
$300ks
- $600ks
Central Parke at Lowes Is..., Sterling, VA
Resale Only
|
55+ age-restricted
|
Built 2003 - 2005
|
181 homes
$300ks
- $800ks
Regency at Ashburn, Ashburn, VA
Resale Only
|
55+ age-restricted
|
Built 2013 - 2020
|
268 homes
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Questions? Call us:
(540) 452-4199
$400ks
- $500ks
Gatherings at Potomac Sta..., Leesburg, VA
New Construction
|
55+ age-restricted
|
Built 2023 - 2024
|
55 homes
$300ks
- $400ks
JerMae Estates, Thurmont, MD
Resale Only
|
55+ age-restricted
|
Built 2003 - 2008
|
108 homes
$300ks
- $400ks
Ballenger Run, Frederick, MD
Resale Only
|
55+ age-restricted
|
Built 2019 - 2020
|
36 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.
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
$400ks
- $500ks
The Village at Harvest Ri..., Winchester, VA
Resale Only
|
55+ age-restricted
|
Built 2005 - 2016
|
82 homes
$800ks
The Retreat at Poland Hil..., Chantilly, VA
Resale Only
|
55+ age-restricted
|
Built 2020 - 2022
|
219 homes
$400ks
The Villages at Broadland..., Ashburn, VA
New and Resale
|
55+ age-restricted
|
Built 2013 - present
|
78 homes
$200ks
- $300ks
Woodbrook Village, Winchester, VA
Resale Only
|
55+ age-restricted
|
Built 1999 - 2001
|
81 homes
$300ks
Cross Creek Village, Winchester, VA
Resale Only
|
55+ age-restricted
|
Built 2001 - 2004
|
90 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
$800ks
Vistas at Lansdowne, Lansdowne, VA
Resale Only
|
55+ age-restricted
|
Built 2015 - 2020
|
120 homes
Want to learn more about 55+ 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
$400ks
- $500ks
CobbleStone Estates, Hagerstown, MD
New and Resale
|
55+ age-restricted
|
Built 2015 - present
|
66 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.
Cedar Meadows
![126 FORGET ME NOT DR, WHITE POST, VA, 22..., White Post, VA 22663]()
MLS VAFV2042224 • Samson Properties, Cynthia Butl...
Trilogy® at Lake Frederick
![109 EMPEROR DR, LAKE FREDERICK, VA, 2263..., Lake Frederick, VA 22630]()
4 beds
|4 baths
|3,859 sq ft
109 EMPEROR DR, LAKE FREDERICK, VA, 2263...
Community: Trilogy® at Lake Frederick
MLS VAFV2041588 • Colony Realty, Paul J Gallagher...
Abrams Chase
![105 AMBERFIELD CT, WINCHESTER, VA, 22602, Winchester, VA 22602]()
MLS VAFV2039578 • Samson Properties, Cynthia Butl...
New
Heritage Hunt
![7055 HERITAGE HUNT DR 111, GAINESVILLE, ..., Gainesville, VA 20155]()
2 beds
|2 baths
|1,421 sq ft
|Condo
7055 HERITAGE HUNT DR 111, GAINESVILLE, ...
Community: Heritage Hunt
MLS VAPW2124608 • RE/MAX Gateway, Penny A Glenn
New
Heritage Hunt
![6845 SADDLE RUN WAY, GAINESVILLE, VA, 20..., Gainesville, VA 20155]()
MLS VAPW2121418 • Samson Properties, Earnest W Go...
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Questions? Call us:
(540) 452-4199
New
Vistas at Lansdowne
![44238 SILVERPALM GROVE TER, LEESBURG, VA..., Leesburg, VA 20176]()
3 beds
|5 baths
|3,891 sq ft
44238 SILVERPALM GROVE TER, LEESBURG, VA...
Community: Vistas at Lansdowne
MLS VALO2130232 • Keller Williams Realty, Jean K ...
Trilogy® at Lake Frederick
![111 SWITCHGRASS WAY, LAKE FREDERICK, VA,..., Lake Frederick, VA 22630]()
3 beds
|3 baths
|2,530 sq ft
111 SWITCHGRASS WAY, LAKE FREDERICK, VA,...
Community: Trilogy® at Lake Frederick
MLS VAFV2042970 • NextHome Realty Select, Michell...
Ballenger Run
![5307 CRAPE MYRTLE DR, FREDERICK, MD, 217..., Frederick, MD 21703]()
MLS MDFR2084812 • Compass, Aaron Jeweler
Regency at Dominion Valley
![5245 ARMOUR CT, HAYMARKET, VA, 20169, Haymarket, VA 20169]()
2 beds
|3 baths
|2,782 sq ft
5245 ARMOUR CT, HAYMARKET, VA, 20169
Community: Regency at Dominion Valley
MLS VAPW2124266 • Real Property Management Pros, ...
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 Ashburn
![20851 SABER JET PL, ASHBURN, VA, 20147, Ashburn, VA 20147]()
MLS VALO2121940 • Keller Williams Realty, Jennife...
Crestwood Village
![5675 BARBERRY CT, FREDERICK, MD, 21703, Frederick, MD 21703]()
MLS MDFR2084756 • Maryland Elite Realtors, Cassan...
The Woodlands of Urbana
![3112 CEDAR GROVE TER, IJAMSVILLE, MD, 21..., Ijamsville, MD 21754]()
3 beds
|3 baths
|3,331 sq ft
3112 CEDAR GROVE TER, IJAMSVILLE, MD, 21...
Community: The Woodlands of Urbana
MLS MDFR2084186 • The Agency DC, Nurit Coombe
Lansdowne Woods of Virginia
![19385 CYPRESS RIDGE TER 903, LEESBURG, V..., Leesburg, VA 20176]()
2 beds
|2 baths
|1,509 sq ft
|Condo
19385 CYPRESS RIDGE TER 903, LEESBURG, V...
Community: Lansdowne Woods of Virginia
MLS VALO2129824 • Samson Properties, Andrew M Nor...
Winchester Landing
![106 HARDY, WINCHESTER, VA, 22602, Winchester, VA 22602]()
MLS VAFV2042996 • MarketPlace REALTY, Lori Oaks
Dunbarton
![12036 RUTHERGLEN PL, BRISTOW, VA, 20136, Bristow, VA 20136]()
MLS VAPW2123918 • RE/MAX Realty Centre, Inc., Her...
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(540) 452-4199
Regency at Ashburn
![44589 YORK CREST TER 405, ASHBURN, VA, 2..., Ashburn, VA 20147]()
2 beds
|2 baths
|1,491 sq ft
|Condo
44589 YORK CREST TER 405, ASHBURN, VA, 2...
Community: Regency at Ashburn
MLS VALO2129622 • Samson Properties, Tammy L Irby
Potomac Green
![20590 HOPE SPRING TER 203, ASHBURN, VA, ..., Ashburn, VA 20147]()
2 beds
|2 baths
|1,347 sq ft
|Condo
20590 HOPE SPRING TER 203, ASHBURN, VA, ...
Community: Potomac Green
MLS VALO2128724 • Keller Williams Realty, Orna Si...
Winchester Landing
![113 WERTLAND PL, WINCHESTER, VA, 22602, Winchester, VA 22602]()
MLS VAFV2042900 • ERA Oakcrest Realty, Inc., Laur...
Regency at Dominion Valley
![5217 ADDLERFIELD WAY, HAYMARKET, VA, 201..., Haymarket, VA 20169]()
3 beds
|3 baths
|3,179 sq ft
5217 ADDLERFIELD WAY, HAYMARKET, VA, 201...
Community: Regency at Dominion Valley
MLS VAPW2122986 • Keller Williams Realty, Kimberl...
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.
Potomac Green
![20610 HOPE SPRING TER 104, ASHBURN, VA, ..., Ashburn, VA 20147]()
2 beds
|2 baths
|876 sq ft
|Condo
20610 HOPE SPRING TER 104, ASHBURN, VA, ...
Community: Potomac Green
MLS VALO2129474 • Pearson Smith Realty, LLC, Dani...
Lexington 7
![19847 SILVERY BLUE TER, ASHBURN, VA, 201..., Ashburn, VA 20147]()
MLS VALO2128942 • Coldwell Banker Realty, Alexis ...
Potomac Green
![44397 OAKMONT MANOR SQ, ASHBURN, VA, 201..., Ashburn, VA 20147]()
MLS VALO2128816 • Real Broker, LLC, Louis Cascian...
Crestwood Village
![6864 SNOWBERRY CT, FREDERICK, MD, 21703, Frederick, MD 21703]()
MLS MDFR2084252 • Maryland Elite Realtors, Cassan...
Central Parke at Lowes Island
![20891 ROYAL VILLA TER, STERLING, VA, 201..., Sterling, VA 20165]()
4 beds
|3 baths
|2,521 sq ft
20891 ROYAL VILLA TER, STERLING, VA, 201...
Community: Central Parke at Lowes Island
MLS VALO2121906 • Pearson Smith Realty, LLC, Gail...
The Village at Foxfield
![4 LAMAR LN, MIDDLETOWN, MD, 21769, Middletown, MD 21769]()
MLS MDFR2084272 • RE/MAX Results, Bobbi Prescott
Emerald Pointe
![19404 AMETHYST DR V59, HAGERSTOWN, MD, 2..., Hagerstown, MD 21742]()
4 beds
|3 baths
|2,559 sq ft
19404 AMETHYST DR V59, HAGERSTOWN, MD, 2...
Community: Emerald Pointe
MLS MDWA2037890 • Berkshire Hathaway HomeServices...
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(540) 452-4199
Lansdowne Woods of Virginia
![19350 MAGNOLIA GROVE SQ 406, LEESBURG, V..., Leesburg, VA 20176]()
2 beds
|2 baths
|1,726 sq ft
|Condo
19350 MAGNOLIA GROVE SQ 406, LEESBURG, V...
Community: Lansdowne Woods of Virginia
MLS VALO2127634 • Compass, Karen A Miller
Heritage Hunt
![13465 VICTORY GALLOP WAY, GAINESVILLE, V..., Gainesville, VA 20155]()
MLS VAPW2122578 • Long & Foster Real Estate, Inc....
Ballenger Run
![5311 CRAPE MYRTLE DR, FREDERICK, MD, 217..., Frederick, MD 21703]()
MLS MDFR2084216 • The Agency DC, Meyer A Leibovit...
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.
Cadence at Lansdowne
![43865 CASTAWAY CAY TER, LEESBURG, VA, 20..., Leesburg, VA 20176]()
3 beds
|3 baths
|2,643 sq ft
43865 CASTAWAY CAY TER, LEESBURG, VA, 20...
Community: Cadence at Lansdowne
MLS VALO2128310 • Samson Properties, Michelle Pal...
Liberty Grove
![9970 WELLINGTON RD, MANASSAS, VA, 20110, Manassas, VA 20110]()
3 beds
|4 baths
|2,404 sq ft
|Condo
9970 WELLINGTON RD, MANASSAS, VA, 20110
Community: Liberty Grove
MLS VAMN2011218 • Pearson Smith Realty LLC, Delie...
Birchwood at Brambleton
![23600 RAYTOWN TER, ASHBURN, VA, 20148, Ashburn, VA 20148]()
3 beds
|4 baths
|2,742 sq ft
23600 RAYTOWN TER, ASHBURN, VA, 20148
Community: Birchwood at Brambleton
MLS VALO2128772 • Century 21 Redwood Realty, Chri...
Lansdowne Woods of Virginia
![19385 CYPRESS RIDGE TER 809, LEESBURG, V..., Leesburg, VA 20176]()
2 beds
|2 baths
|1,246 sq ft
|Condo
19385 CYPRESS RIDGE TER 809, LEESBURG, V...
Community: Lansdowne Woods of Virginia
MLS VALO2128546 • Samson Properties, Phyllis Ann ...
Birchwood at Brambleton
![42874 FIREFLY SONATA TER 403, ASHBURN, V..., Ashburn, VA 20148]()
3 beds
|2 baths
|1,712 sq ft
|Condo
42874 FIREFLY SONATA TER 403, ASHBURN, V...
Community: Birchwood at Brambleton
MLS VALO2128692 • Giant Realty, Inc., Yun J Heo
The Flats at Heathcote Village by Del Webb
![6091 AZURITE WAY, HAYMARKET, VA, 20169, Haymarket, VA 20169]()
3 beds
|3 baths
|2,625 sq ft
6091 AZURITE WAY, HAYMARKET, VA, 20169
Community: The Flats at Heathcote Village by Del Webb
MLS VAPW2122954 • Monument Sotheby's Internationa...
The Flats at Heathcote Village by Del Webb
![6099 AZURITE WAY, HAYMARKET, VA, 20169, Haymarket, VA 20169]()
3 beds
|3 baths
|2,763 sq ft
6099 AZURITE WAY, HAYMARKET, VA, 20169
Community: The Flats at Heathcote Village by Del Webb
MLS VAPW2122950 • Monument Sotheby's Internationa...
The Flats at Heathcote Village by Del Webb
![5926 SUNSTONE LN, HAYMARKET, VA, 20169, Haymarket, VA 20169]()
3 beds
|3 baths
|2,763 sq ft
5926 SUNSTONE LN, HAYMARKET, VA, 20169
Community: The Flats at Heathcote Village by Del Webb
MLS VAPW2122936 • Monument Sotheby's Internationa...
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The Flats at Heathcote Village by Del Webb
![5928 SUNSTONE LN, HAYMARKET, VA, 20169, Haymarket, VA 20169]()
3 beds
|4 baths
|2,763 sq ft
5928 SUNSTONE LN, HAYMARKET, VA, 20169
Community: The Flats at Heathcote Village by Del Webb
MLS VAPW2122944 • Monument Sotheby's Internationa...
The Village at Harvest Ridge
![116 HARVEST RIDGE DR, WINCHESTER, VA, 22..., Winchester, VA 22601]()
3 beds
|3 baths
|3,573 sq ft
116 HARVEST RIDGE DR, WINCHESTER, VA, 22...
Community: The Village at Harvest Ridge
MLS VAFV2042674 • RE/MAX Roots, David K Spence
Download the Ultimate 55+ Homebuying Guide
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Frequently Asked Questions
In the Winchester Area, there are no large communities, 1 medium community with 500-1000 homes, and 10 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 173 homes.
Yes, there are new 55+ homes available in the Winchester Area. The most recent communities started in the Winchester Area include Winchester Landing, Abrams Chase, Cottage Glen. There are also 4 communities in the Winchester Area that offer new construction homes, including Cottage Glen, Trilogy® at Lake Frederick, Willow Run.
Yes, there are gated 55+ communities in the Winchester Area. Approximately 33.3% of 55+ communities in the area are gated. For instance, Cottage Glen is a gated communities with 25 homes, and Cedar Meadows is another gated communities with 129 homes.
On average, listings in 55+ communities in the Winchester Area stay on the market for around 620 days. The average price of homes for sale in these communities is approximately $480,385, though prices can range widely based on the size, location, and amenities of the communities. For example, homes in The Village at Harvest Ridge average around $625,881, while homes in Cottage Glen average around $464,750.
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: Jul 06, 2026.
This application does not include information on all of the properties available for sale at this time.
