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 - Page 5
51 communities near Winchester Area
238 homes near Winchester Area
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5 rating (31 reviews)
$200ks
- $500ks
Lansdowne Woods of Virgin..., Lansdowne, VA
Resale Only |
55+ age-restricted |
Built 1998 - 2017 |
1,200 homes
5 rating (2 reviews)
$400ks
- $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 review)
$400ks
- $1Ms
Birchwood at Brambleton, Ashburn, VA
New and Resale |
55+ age-restricted |
Built 2016 - present |
1,502 homes
5 rating (3 reviews)
$400ks
- $600ks
Heritage Hunt, Gainesville, VA
Resale Only |
55+ age-restricted |
Built 1998 - 2009 |
1,863 homes
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5 rating (1 review)
$200ks
- $500ks
Crestwood Village, Frederick, MD
Resale Only |
55+ age-restricted |
Built 1979 - 1999 |
550 homes
5 rating (1 review)
$300ks
- $1Ms
Regency at Dominion Valle..., Haymarket, VA
Resale Only |
55+ age-restricted |
Built 2001 - 2017 |
855 homes
$500ks
- $700ks
The Woodlands of Urbana, Urbana, MD
Resale Only |
55+ age-restricted |
Built 2019 - 2025 |
565 homes
$700ks
- $800ks
Bloomfields 55+, Frederick, MD
New Construction |
55+ age-restricted |
Built 2026 - present
$600ks
- $900ks
Regency at Belmont, Ashburn, VA
New Construction |
55+ age-restricted |
Built 2021 - present |
145 homes
Download the Ultimate 55+ Homebuying Guide
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5 rating (1 review)
$300ks
Willow Lawn Cottages, Winchester, VA
Resale Only |
55+ age-restricted |
Built 1999 - 2004 |
120 homes
5 rating (2 reviews)
$400ks
- $800ks
Potomac Green, Ashburn, VA
Resale Only |
55+ age-restricted |
Built 2005 - 2016 |
1,400 homes
$300ks
- $500ks
Emerald Pointe, Hagerstown, MD
New and Resale |
55+ age-restricted |
Built 2008 - present |
250 homes
$500ks
- $600ks
Willow Run, Winchester, VA
New Construction |
55+ age-restricted |
300 homes
$600ks
Cadence at Lansdowne, Lansdowne, VA
Resale Only |
55+ age-restricted |
Built 2020 - 2024 |
74 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
$400ks
- $600ks
The Highlands at Blue Rid..., Front Royal, VA
Resale Only |
55+ age-restricted |
Built 2017 - 2019 |
42 homes
$300ks
- $400ks
Heritage Highlands, Lovettsville, VA
Resale Only |
55+ age-restricted |
Built 2017 - 2020 |
80 homes
$300ks
- $400ks
Cedar Meadows, White Post, VA
Resale Only |
55+ age-restricted |
Built 2010 - 2022 |
129 homes
$400ks
Suffield Meadows, Warrenton, VA
Resale Only |
55+ age-restricted |
Built 2005 - 2011 |
112 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
$300ks
Rosehill Manor Villas, Hagerstown, MD
New Construction |
55+ age-restricted |
Built 2022 - present |
177 homes
$200ks
- $300ks
Liberty Grove, Manassas, VA
Resale Only |
55+ age-restricted |
Built 2005 - 2005 |
61 homes
5 rating (1 review)
$300ks
- $400ks
Gatherings at Wellington, Manassas, VA
Resale Only |
55+ age-restricted |
Built 2011 - 2016 |
135 homes
$800ks
Vistas at Lansdowne, Lansdowne, VA
Resale Only |
55+ age-restricted |
Built 2015 - 2020 |
120 homes
3 rating (2 reviews)
$300ks
- $500ks
Dunbarton, Bristow, VA
Resale Only |
55+ age-restricted |
Built 2000 - 2009 |
479 homes
$300ks
- $400ks
The Signature at Broadlan..., Ashburn, VA
Resale Only |
55+ age-restricted |
Built 2018 - 2020 |
45 homes
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Questions? Call us:
(540) 452-4199
3.7 rating (3 reviews)
$300ks
- $400ks
Four Seasons at Ashburn V..., Ashburn, VA
Resale Only |
55+ age-restricted |
Built 2005 - 2005 |
80 homes
5 rating (1 review)
$600ks
Four Seasons at Vint Hill, Warrenton, VA
Resale Only |
55+ age-restricted |
Built 2004 - 2006 |
100 homes
$200ks
- $300ks
Woodbrook Village, Winchester, VA
Resale Only |
55+ age-restricted |
Built 1999 - 2001 |
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.
$500ks
- $600ks
Boxwood Villas, Urbana, MD
Resale Only |
55+ age-restricted |
Built 2019 - 2021 |
92 homes
$400ks
- $500ks
The Village at Harvest Ri..., Winchester, VA
Resale Only |
55+ age-restricted |
Built 2005 - 2016 |
82 homes
$600ks
- $700ks
Lexington 7, Ashburn, VA
Resale Only |
55+ age-restricted |
Built 2017 - 2020 |
113 homes
$300ks
- $800ks
Regency at Ashburn, Ashburn, VA
Resale Only |
55+ age-restricted |
Built 2013 - 2020 |
268 homes
$300ks
Cross Creek Village, Winchester, VA
Resale Only |
55+ age-restricted |
Built 2001 - 2004 |
90 homes
$400ks
- $500ks
Gatherings at Potomac Sta..., Leesburg, VA
New Construction |
55+ age-restricted |
Built 2023 - 2024 |
55 homes
$300ks
- $600ks
Central Parke at Lowes Is..., Sterling, VA
Resale Only |
55+ age-restricted |
Built 2003 - 2005 |
181 homes
$300ks
- $600ks
Montebello, Sterling, VA
New and Resale |
55+ age-restricted |
Built 2022 - present |
450 homes
Want to learn more about 55+ communities in Winchester Area?
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Questions? Call us:
(540) 452-4199
$600ks
- $700ks
Robinson Manor, Gainesville, VA
New Construction |
55+ age-restricted |
Built 2023 - present |
50 homes
$400ks
The Villages at Broadland..., Ashburn, VA
New and Resale |
55+ age-restricted |
Built 2013 - present |
78 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.
Heritage Hunt
MLS VAPW2126498 • Long & Foster Real Estate, Inc.... • Long & Foster Real Estate, Inc.
Gatherings at Wellington
2 beds
|2 baths
|1,558 sq ft
|Condo
10275 FOUNTAIN CIR 306, MANASSAS, VA, 20...
Community: Gatherings at Wellington
MLS VAMN2011592 • LPT Realty, LLC, Juliet Mayers • LPT Realty, LLC
Cadence at Lansdowne
5 beds
|5 baths
|3,969 sq ft
43928 MARITIME SONG TER, LEESBURG, VA, 2...
Community: Cadence at Lansdowne
MLS VALO2132480 • Weichert, REALTORS, Anita G Mas... • Weichert, REALTORS
Heritage Hunt
MLS VAPW2126382 • Samson Properties, James Matthe... • Samson Properties
The Woodlands of Urbana
3 beds
|3 baths
|2,612 sq ft
3231 THORNAPPLE DR, FREDERICK, MD, 21704
Community: The Woodlands of Urbana
MLS MDFR2082442 • LPT Realty, LLC, Brooke Steinho... • LPT Realty, LLC
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Questions? Call us:
(540) 452-4199
Trilogy® at Lake Frederick
4 beds
|4 baths
|4,828 sq ft
105 TURNSTONE LN, LAKE FREDERICK, VA, 22...
Community: Trilogy® at Lake Frederick
MLS VAFV2043520 • Real Broker, LLC, Chris J Colga... • Real Broker, LLC
Suffield Meadows
4 beds
|3 baths
|3,066 sq ft
|Condo
6727 HOLLY FARM LN, WARRENTON, VA, 20187
Community: Suffield Meadows
MLS VAFQ2023186 • Redfin Corporation, Kendell A W... • Redfin Corporation
Heritage Hunt
2 beds
|2 baths
|1,388 sq ft
|Condo
13890 CHELMSFORD DR 305, GAINESVILLE, VA...
Community: Heritage Hunt
MLS VAPW2126016 • Real Property Management Pros, ... • Real Property Management Pros
Trilogy® at Lake Frederick
4 beds
|3 baths
|2,080 sq ft
112 FRINGETREE CT, LAKE FREDERICK, VA, 2...
Community: Trilogy® at Lake Frederick
MLS VAFV2043328 • RE/MAX Galaxy, Iftikhar Khan • RE/MAX Galaxy
Birchwood at Brambleton
1 beds
|2 baths
|1,229 sq ft
|Condo
23665 HAVELOCK WALK TER 406, ASHBURN, VA...
Community: Birchwood at Brambleton
MLS VALO2131848 • Compass, Jason Thomas • Compass
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
2 beds
|2 baths
|1,708 sq ft
|Condo
19370 MAGNOLIA GROVE SQ L04, LEESBURG, V...
Community: Lansdowne Woods of Virginia
MLS VALO2131688 • Berkshire Hathaway HomeServices... • Berkshire Hathaway HomeServices PenFed Realty
Trilogy® at Lake Frederick
4 beds
|3 baths
|3,114 sq ft
106 ATLANTIS LN, LAKE FREDERICK, VA, 226...
Community: Trilogy® at Lake Frederick
MLS VAFV2043480 • Preslee Real Estate, Abby L Wal... • Preslee Real Estate
Birchwood at Brambleton
3 beds
|2 baths
|1,712 sq ft
|Condo
42874 FIREFLY SONATA TER 403, ASHBURN, V...
Community: Birchwood at Brambleton
MLS VALO2131344 • Keller Williams Realty, Victori... • Keller Williams Realty
Emerald Pointe
MLS MDWA2038150 • Keller Williams Realty Centre, ... • Keller Williams Realty Centre
Crestwood Village
2 beds
|1 baths
|1,297 sq ft
5603 HONEYSUCKLE CT, FREDERICK, MD, 2170...
Community: Crestwood Village
MLS MDFR2085508 • Real Estate Teams, LLC, SEAN WI... • Real Estate Teams, LLC
Willow Lawn Cottages
2 beds
|2 baths
|1,431 sq ft
1826 KERSHAW LN, WINCHESTER, VA, 22601
Community: Willow Lawn Cottages
MLS VAWI2011142 • RE/MAX Roots, Roxanna D Grimes • RE/MAX Roots
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(540) 452-4199
Regency at Dominion Valley
4 beds
|4 baths
|3,962 sq ft
5416 ZOYSIA CT, HAYMARKET, VA, 20169
Community: Regency at Dominion Valley
MLS VAPW2124720 • Long & Foster Real Estate, Inc.... • Long & Foster Real Estate, Inc.
Birchwood at Brambleton
3 beds
|2 baths
|1,972 sq ft
|Condo
23639 GOLDEN EMBERS SQ 302, ASHBURN, VA,...
Community: Birchwood at Brambleton
MLS VALO2130694 • Spring Hill Real Estate, LLC., ... • Spring Hill Real Estate, LLC.
Trilogy® at Lake Frederick
3 beds
|4 baths
|3,604 sq ft
117 MALLARD DR, LAKE FREDERICK, VA, 2263...
Community: Trilogy® at Lake Frederick
MLS VAFV2043178 • CTI Real Estate, Stacey Renee S... • CTI Real Estate
Lansdowne Woods of Virginia
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... • Samson Properties
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.
Cindy Certified
Winchester Landing
MLS VAFV2042900 • ERA Oakcrest Realty, Inc., Laur... • ERA Oakcrest Realty, Inc.
Cindy Certified
Potomac Green
MLS VALO2128816 • Real Broker, LLC, Louis Cascian... • Real Broker, LLC
Ballenger Run
MLS MDFR2084216 • The Agency DC, Meyer A Leibovit... • The Agency DC
Cadence at Lansdowne
3 beds
|3 baths
|3,868 sq ft
43865 CASTAWAY CAY TER, LEESBURG, VA, 20...
Community: Cadence at Lansdowne
MLS VALO2128310 • Samson Properties, Michelle Pal... • Samson Properties
Birchwood at Brambleton
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... • Century 21 Redwood Realty
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Winchester Landing
MLS VAFV2042592 • Realty ONE Group Old Towne, Ste... • Realty ONE Group Old Towne
The Woodlands of Urbana
3 beds
|3 baths
|1,817 sq ft
3264 STARLIGHT ST, FREDERICK, MD, 21704
Community: The Woodlands of Urbana
MLS MDFR2083816 • Samson Properties, Hanh H Pham • Samson Properties
Lansdowne Woods of Virginia
3 beds
|2 baths
|1,627 sq ft
|Condo
19385 CYPRESS RDG 515, LEESBURG, VA, 201...
Community: Lansdowne Woods of Virginia
MLS VALO2127326 • Samson Properties, Robert J Che... • Samson Properties
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 Hunt
MLS VAPW2118730 • RE/MAX Gateway, LLC, Scott A. M... • RE/MAX Gateway, LLC
Dunbarton
MLS VAPW2118512 • Weichert, REALTORS, Wendy Hacke... • Weichert, REALTORS
Heritage Hunt
MLS VAPW2121736 • Keller Williams Realty, Matias ... • Keller Williams Realty
Regency at Dominion Valley
2 beds
|2 baths
|1,499 sq ft
|Condo
15100 HEATHER MILL LN 304, HAYMARKET, VA...
Community: Regency at Dominion Valley
MLS VAPW2120582 • Ross Real Estate, Layne Jensen • Ross Real Estate
Trilogy® at Lake Frederick
3 beds
|3 baths
|3,557 sq ft
110 PIPIT CT, LAKE FREDERICK, VA, 22630
Community: Trilogy® at Lake Frederick
MLS VAFV2042116 • Keller Williams Realty, Matt Bo... • Keller Williams Realty
Cadence at Lansdowne
3 beds
|5 baths
|3,679 sq ft
19006 CORAL REEF SQ, LEESBURG, VA, 20176
Community: Cadence at Lansdowne
MLS VALO2125364 • Hunt Country Sotheby's Internat... • Hunt Country Sotheby's International Realty
Cindy Certified
Suffield Meadows
3 beds
|3 baths
|3,701 sq ft
|Condo
6708 STREAM VIEW LN, WARRENTON, VA, 2018...
Community: Suffield Meadows
MLS VAFQ2022010 • Long & Foster Real Estate, Inc.... • Long & Foster Real Estate, Inc.
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Birchwood at Brambleton
3 beds
|2 baths
|1,908 sq ft
|Condo
23640 BOLTON CRESCENT TER 403, ASHBURN, ...
Community: Birchwood at Brambleton
MLS VALO2125616 • Compass, Scotti S Sellers • Compass
Trilogy® at Lake Frederick
3 beds
|3 baths
|2,173 sq ft
134 ATLANTIS LN, LAKE FREDERICK, VA, 226...
Community: Trilogy® at Lake Frederick
MLS VAFV2041520 • Berkshire Hathaway HomeServices... • Berkshire Hathaway HomeServices PenFed Realty
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.
Frequently Asked Questions
Of the 12 55+ communities in the Winchester Area, 12 are for sale and none are rentals. By size, 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 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 588 days. The average price of homes for sale in these communities is approximately $491,100, though prices can range widely based on the size, location, and amenities of the communities. For example, homes in Willow Run average around $623,623, while homes in Cottage Glen average around $464,750.
Want to learn more about 55+ communities in the Winchester Area?
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- Answers from local 55+ experts
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The listings data displayed on this medium comes in part from the Real Estate Information Network Inc. (REIN) and has been authorized by participating listing Broker Members of REIN for display. REIN's listings are based upon Data submitted by its Broker Members, and REIN therefore makes no representation or warranty regarding the accuracy of the Data. All users of REIN's listings database should confirm the accuracy of the listing information directly with the listing agent.
© 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: Oct 22, 2026.
This application does not include information on all of the properties available for sale at this time.
