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
50 communities near Winchester Area
150 homes near Winchester Area
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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
$300ks
- $500ks
The Flats at Heathcote Vi..., Haymarket, VA
New Construction
|
55+ age-restricted
|
Built 2026 - present
|
500 homes
5 rating (2 reviews)
![Trilogy® at Lake Frederic...]()
$400ks
- $800ks
Trilogy® at Lake Frederic..., Lake Frederick, VA
New and Resale
|
55+ age-restricted
|
Built 2006 - present
|
950 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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(540) 452-4199
$300ks
- $500ks
Emerald Pointe, Hagerstown, MD
New and Resale
|
55+ age-restricted
|
Built 2008 - present
|
250 homes
$300ks
Rosehill Manor Villas, Hagerstown, MD
New Construction
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55+ age-restricted
|
Built 2022 - present
|
177 homes
5 rating (2 reviews)
![Potomac Green]()
$400ks
- $800ks
Potomac Green, Ashburn, VA
Resale Only
|
55+ age-restricted
|
Built 2005 - 2016
|
1,400 homes
5 rating (1 reviews)
![Crestwood Village]()
$200ks
- $500ks
Crestwood Village, Frederick, MD
Resale Only
|
55+ age-restricted
|
Built 1979 - 1999
|
550 homes
Download the Ultimate 55+ Homebuying Guide
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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
- $400ks
Winchester Landing, Winchester, VA
Resale Only
|
55+ age-restricted
|
Built 2023 - 2025
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
$600ks
Cadence at Lansdowne, Lansdowne, VA
Resale Only
|
55+ age-restricted
|
Built 2020 - 2024
|
74 homes
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(540) 452-4199
$500ks
- $700ks
The Woodlands of Urbana, Urbana, MD
Resale Only
|
55+ age-restricted
|
Built 2019 - 2025
|
565 homes
$600ks
- $700ks
Lexington 7, Ashburn, VA
Resale Only
|
55+ age-restricted
|
Built 2017 - 2020
|
113 homes
$800ks
- $1Ms
Lexington Square, Ashburn, VA
New Construction
|
55+ age-restricted
|
Built 2024 - present
|
23 homes
$500ks
- $600ks
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.
5 rating (1 reviews)
![Gatherings at Wellington]()
$300ks
- $400ks
Gatherings at Wellington, Manassas, VA
Resale Only
|
55+ age-restricted
|
Built 2011 - 2016
|
135 homes
$600ks
- $700ks
Robinson Manor, Gainesville, VA
New Construction
|
55+ age-restricted
|
Built 2023 - present
|
50 homes
$800ks
The Retreat at Poland Hil..., Chantilly, VA
Resale Only
|
55+ age-restricted
|
Built 2020 - 2022
|
219 homes
$300ks
The Village at Freedom Hi..., Hagerstown, MD
New and Resale
|
55+ age-restricted
|
Built 2007 - present
|
66 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
$400ks
- $500ks
CobbleStone Estates, Hagerstown, MD
New and Resale
|
55+ age-restricted
|
Built 2015 - present
|
66 homes
$200ks
- $300ks
Liberty Grove, Manassas, VA
Resale Only
|
55+ age-restricted
|
Built 2005 - 2005
|
61 homes
$300ks
- $500ks
The Village at Foxfield, Middletown, MD
Resale Only
|
55+ age-restricted
|
Built 2003 - 2012
|
81 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
Regency at Creekside, Gainesville, VA
Resale Only
|
55+ age-restricted
|
Built 2016 - 2020
|
208 homes
$400ks
- $600ks
The Highlands at Blue Rid..., Front Royal, VA
Resale Only
|
55+ age-restricted
|
Built 2017 - 2019
|
42 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
Want to learn more about 55+ communities in Winchester Area?
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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
$500ks
- $600ks
Boxwood Villas, Urbana, MD
Resale Only
|
55+ age-restricted
|
Built 2019 - 2021
|
92 homes
$300ks
- $400ks
Ballenger Run, Frederick, MD
Resale Only
|
55+ age-restricted
|
Built 2019 - 2020
|
36 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
- $900ks
Regency at Belmont, Ashburn, VA
New Construction
|
55+ age-restricted
|
Built 2021 - present
|
145 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
$300ks
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?
55places can help!
Questions? Call us:
(540) 452-4199
$300ks
- $400ks
Cedar Meadows, White Post, VA
Resale Only
|
55+ age-restricted
|
Built 2010 - 2022
|
129 homes
New
Regency at Dominion Valley
![5417 ZOYSIA CT, HAYMARKET, VA, 20169, Haymarket, VA 20169]()
4 beds
|4 baths
|4,036 sq ft
5417 ZOYSIA CT, HAYMARKET, VA, 20169
Community: Regency at Dominion Valley
MLS VAPW2113030 • Corcoran McEnearney, Susan B Th...
New
Robinson Manor
![14712 GRAND CRU LOOP, GAINESVILLE, VA, 2..., Gainesville, VA 20155]()
3 beds
|3 baths
|2,270 sq ft
14712 GRAND CRU LOOP, GAINESVILLE, VA, 2...
Community: Robinson Manor
MLS VAPW2112920 • Keller Williams Realty/Lee Beav...
New
Abrams Chase
![105 AMBERFIELD CT, WINCHESTER, VA, 22602, Winchester, VA 22602]()
MLS VAFV2039578 • Samson Properties, Cynthia Butl...
New
Heritage Hunt
![6595 ALDERWOOD WAY, GAINESVILLE, VA, 201..., Gainesville, VA 20155]()
MLS VAPW2112878 • Samson Properties, Tricia Leigh...
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(540) 452-4199
Regency at Dominion Valley
![15251 ROYAL CREST DR APT 103, HAYMARKET,..., Haymarket, VA 20169]()
2 beds
|2 baths
|1,499 sq ft
|Condo
15251 ROYAL CREST DR APT 103, HAYMARKET,...
Community: Regency at Dominion Valley
MLS VAPW2112500 • RE/MAX Real Estate Connections,...
Suffield Meadows
![6696 CLUB HOUSE LN UNIT 206, WARRENTON, ..., Warrenton, VA 20187]()
2 beds
|2 baths
|1,372 sq ft
|Condo
6696 CLUB HOUSE LN UNIT 206, WARRENTON, ...
Community: Suffield Meadows
MLS VAFQ2020356 • Keller Williams Realty, Kimberl...
Crestwood Village
![5693 CRABAPPLE DR, FREDERICK, MD, 21703, Frederick, MD 21703]()
MLS MDFR2077216 • Rosario Realty, Richard Henry R...
Birchwood at Brambleton
![23626 JAYADEV TER, ASHBURN, VA, 20148, Ashburn, VA 20148]()
3 beds
|3 baths
|2,906 sq ft
23626 JAYADEV TER, ASHBURN, VA, 20148
Community: Birchwood at Brambleton
MLS VALO2116096 • Berkshire Hathaway HomeServices...
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 Flats at Heathcote Village by Del Webb
![5907 SUNSTONE LN, HAYMARKET, VA, 20169, Haymarket, VA 20169]()
3 beds
|3 baths
|3,734 sq ft
5907 SUNSTONE LN, HAYMARKET, VA, 20169
Community: The Flats at Heathcote Village by Del Webb
MLS VAPW2112510 • Monument Sotheby's Internationa...
Regency at Dominion Valley
![5450 TREVINO DR, HAYMARKET, VA, 20169, Haymarket, VA 20169]()
3 beds
|3 baths
|2,712 sq ft
5450 TREVINO DR, HAYMARKET, VA, 20169
Community: Regency at Dominion Valley
MLS VAPW2112294 • Samson Properties, Kerri Bryn R...
Trilogy® at Lake Frederick
![136 MALLARD DR, LAKE FREDERICK, VA, 2263..., Lake Frederick, VA 22630]()
2 beds
|2 baths
|2,089 sq ft
136 MALLARD DR, LAKE FREDERICK, VA, 2263...
Community: Trilogy® at Lake Frederick
MLS VAFV2039502 • MarketPlace REALTY, Kimberly D ...
Willow Run
![LOT 0057 HYDRANGEA WAY, WINCHESTER, VA, ..., Winchester, VA 22602]()
MLS VAFV2039564 • D R Horton Realty of Virginia L...
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(540) 452-4199
Willow Run
![LOT 0055 HYDRANGEA WAY, WINCHESTER, VA, ..., Winchester, VA 22602]()
MLS VAFV2039562 • D R Horton Realty of Virginia L...
Willow Run
![118 TRELLIS VIEW LN, WINCHESTER, VA, 226..., Winchester, VA 22602]()
MLS VAFV2039558 • D R Horton Realty of Virginia L...
Heritage Hunt
![13663 HERITAGE VALLEY WAY, GAINESVILLE, ..., Gainesville, VA 20155]()
MLS VAPW2112360 • 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.
Birchwood at Brambleton
![23630 HAVELOCK WALK TER 402, ASHBURN, VA..., Ashburn, VA 20148]()
2 beds
|2 baths
|1,244 sq ft
|Condo
23630 HAVELOCK WALK TER 402, ASHBURN, VA...
Community: Birchwood at Brambleton
MLS VALO2115762 • Samson Properties, Ferris B Ewa...
Heritage Hunt
![13170 TRIPLE CROWN LOOP, GAINESVILLE, VA..., Gainesville, VA 20155]()
MLS VAPW2111916 • Long & Foster Real Estate, Inc....
Heritage Hunt
![14025 BREEDERS CUP DR, GAINESVILLE, VA, ..., Gainesville, VA 20155]()
MLS VAPW2112262 • Samson Properties, James Matthe...
Heritage Hunt
![13359 FIELDSTONE WAY, GAINESVILLE, VA, 2..., Gainesville, VA 20155]()
MLS VAPW2112220 • RLAH @properties, Candace Moe
Want to learn more about 55+ communities in Winchester Area?
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(540) 452-4199
The Flats at Heathcote Village by Del Webb
![6052 SUNSTONE LN, HAYMARKET, VA, 20169, Haymarket, VA 20169]()
3 beds
|3 baths
|2,763 sq ft
6052 SUNSTONE LN, HAYMARKET, VA, 20169
Community: The Flats at Heathcote Village by Del Webb
MLS VAPW2112240 • Monument Sotheby's Internationa...
Birchwood at Brambleton
![23631 HAVELOCK WALK TER 421, ASHBURN, VA..., Ashburn, VA 20148]()
3 beds
|2 baths
|1,906 sq ft
|Condo
23631 HAVELOCK WALK TER 421, ASHBURN, VA...
Community: Birchwood at Brambleton
MLS VALO2113380 • Real Broker, LLC, Peter B Knapp
Heritage Hunt
![6932 WALNUT HILL DR, GAINESVILLE, VA, 20..., Gainesville, VA 20155]()
MLS VAPW2109956 • Real Broker, LLC, Peter B Knapp
The Flats at Heathcote Village by Del Webb
![5800 MOONSTONE WAY 7, HAYMARKET, VA, 201..., Haymarket, VA 20169]()
2 beds
|2 baths
|1,445 sq ft
|Condo
5800 MOONSTONE WAY 7, HAYMARKET, VA, 201...
Community: The Flats at Heathcote Village by Del Webb
MLS VAPW2112238 • Monument Sotheby's Internationa...
The Flats at Heathcote Village by Del Webb
![5800 MOONSTONE WAY 6, HAYMARKET, VA, 201..., Haymarket, VA 20169]()
1 beds
|2 baths
|995 sq ft
|Condo
5800 MOONSTONE WAY 6, HAYMARKET, VA, 201...
Community: The Flats at Heathcote Village by Del Webb
MLS VAPW2112236 • Monument Sotheby's Internationa...
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 Flats at Heathcote Village by Del Webb
![5800 MOONSTONE WAY 5, HAYMARKET, VA, 201..., Haymarket, VA 20169]()
3 beds
|2 baths
|1,850 sq ft
|Condo
5800 MOONSTONE WAY 5, HAYMARKET, VA, 201...
Community: The Flats at Heathcote Village by Del Webb
MLS VAPW2112234 • Monument Sotheby's Internationa...
The Flats at Heathcote Village by Del Webb
![5800 MOONSTONE WAY 4, HAYMARKET, VA, 201..., Haymarket, VA 20169]()
2 beds
|2 baths
|1,520 sq ft
|Condo
5800 MOONSTONE WAY 4, HAYMARKET, VA, 201...
Community: The Flats at Heathcote Village by Del Webb
MLS VAPW2112232 • Monument Sotheby's Internationa...
The Flats at Heathcote Village by Del Webb
![5800 MOONSTONE WAY 3, HAYMARKET, VA, 201..., Haymarket, VA 20169]()
3 beds
|2 baths
|1,735 sq ft
|Condo
5800 MOONSTONE WAY 3, HAYMARKET, VA, 201...
Community: The Flats at Heathcote Village by Del Webb
MLS VAPW2112230 • Monument Sotheby's Internationa...
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The Flats at Heathcote Village by Del Webb
![5800 MOONSTONE WAY 2, HAYMARKET, VA, 201..., Haymarket, VA 20169]()
2 beds
|2 baths
|1,345 sq ft
|Condo
5800 MOONSTONE WAY 2, HAYMARKET, VA, 201...
Community: The Flats at Heathcote Village by Del Webb
MLS VAPW2112228 • Monument Sotheby's Internationa...
The Flats at Heathcote Village by Del Webb
![5800 MOONSTONE WAY 1, HAYMARKET, VA, 201..., Haymarket, VA 20169]()
2 beds
|2 baths
|1,475 sq ft
|Condo
5800 MOONSTONE WAY 1, HAYMARKET, VA, 201...
Community: The Flats at Heathcote Village by Del Webb
MLS VAPW2112224 • Monument Sotheby's Internationa...
The Village at Foxfield
![1 KELLER LN, MIDDLETOWN, MD, 21769, Middletown, MD 21769]()
3 beds
|3 baths
|3,161 sq ft
1 KELLER LN, MIDDLETOWN, MD, 21769
Community: The Village at Foxfield
MLS MDFR2076674 • Long & Foster Real Estate, Inc....
Heritage Hunt
![7055 HERITAGE HUNT DR 311, GAINESVILLE, ..., Gainesville, VA 20155]()
2 beds
|2 baths
|1,421 sq ft
|Condo
7055 HERITAGE HUNT DR 311, GAINESVILLE, ...
Community: Heritage Hunt
MLS VAPW2110212 • Long & Foster Real Estate, Inc....
Potomac Green
![20763 CRESCENT POINTE PL, ASHBURN, VA, 2..., Ashburn, VA 20147]()
MLS VALO2115330 • Berkshire Hathaway HomeServices...
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.
Heritage Highlands
![77 HARPERS MILL WAY, LOVETTSVILLE, VA, 2..., Lovettsville, VA 20180]()
3 beds
|3 baths
|2,119 sq ft
77 HARPERS MILL WAY, LOVETTSVILLE, VA, 2...
Community: Heritage Highlands
MLS VALO2115370 • Long & Foster Real Estate, Inc....
Willow Lawn Cottages
![1885 ROSSER LN, WINCHESTER, VA, 22601, Winchester, VA 22601]()
2 beds
|2 baths
|1,550 sq ft
1885 ROSSER LN, WINCHESTER, VA, 22601
Community: Willow Lawn Cottages
MLS VAWI2009918 • OliveTree Property Group, Misty...
Regency at Dominion Valley
![15110 HEATHER MILL LN APT 402, HAYMARKET..., Haymarket, VA 20169]()
2 beds
|2 baths
|1,551 sq ft
|Condo
15110 HEATHER MILL LN APT 402, HAYMARKET...
Community: Regency at Dominion Valley
MLS VAPW2111984 • Berkshire Hathaway HomeServices...
Regency at Dominion Valley
![5112 FALDO DR, HAYMARKET, VA, 20169, Haymarket, VA 20169]()
3 beds
|3 baths
|2,754 sq ft
5112 FALDO DR, HAYMARKET, VA, 20169
Community: Regency at Dominion Valley
MLS VAPW2111976 • Samson Properties, Cynthia Giud...
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Birchwood at Brambleton
![23631 HAVELOCK WALK TER UNIT 302, ASHBUR..., Ashburn, VA 20148]()
2 beds
|2 baths
|1,244 sq ft
|Condo
23631 HAVELOCK WALK TER UNIT 302, ASHBUR...
Community: Birchwood at Brambleton
MLS VALO2115070 • Samson Properties, Eric Purvis
Rosehill Manor Villas
![19604 LAVENDER LN, HAGERSTOWN, MD, 21742, Hagerstown, MD 21742]()
2 beds
|2 baths
|1,767 sq ft
19604 LAVENDER LN, HAGERSTOWN, MD, 21742
Community: Rosehill Manor Villas
MLS MDWA2033864 • Keller Williams Realty Centre, ...
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
- Instant new home alerts
- 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: Feb 24, 2026.
This application does not include information on all of the properties available for sale at this time.
