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
219 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
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
The Flats at Heathcote Vi..., Haymarket, VA
New Construction
|
55+ age-restricted
|
Built 2026 - present
|
500 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
5 rating (1 reviews)
![Crestwood Village]()
$200ks
- $500ks
Crestwood Village, Frederick, MD
Resale Only
|
55+ age-restricted
|
Built 1979 - 1999
|
550 homes
$700ks
- $800ks
Bloomfields 55+, Frederick, MD
New Construction
|
55+ age-restricted
|
Built 2026 - present
$300ks
Rosehill Manor Villas, Hagerstown, MD
New Construction
|
55+ age-restricted
|
Built 2022 - present
|
177 homes
Download the Ultimate 55+ Homebuying Guide
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$300ks
- $500ks
Emerald Pointe, Hagerstown, MD
New and Resale
|
55+ age-restricted
|
Built 2008 - present
|
250 homes
$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
|
55+ age-restricted
|
Built 2010 - 2022
|
129 homes
5 rating (2 reviews)
![Potomac Green]()
$400ks
- $800ks
Potomac Green, Ashburn, VA
Resale Only
|
55+ age-restricted
|
Built 2005 - 2016
|
1,400 homes
$600ks
Cadence at Lansdowne, Lansdowne, VA
Resale Only
|
55+ age-restricted
|
Built 2020 - 2024
|
74 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
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$200ks
- $300ks
Liberty Grove, Manassas, VA
Resale Only
|
55+ age-restricted
|
Built 2005 - 2005
|
61 homes
$600ks
- $900ks
Regency at Belmont, Ashburn, VA
New Construction
|
55+ age-restricted
|
Built 2021 - present
|
145 homes
$500ks
- $700ks
Montebello, Sterling, VA
New and Resale
|
55+ age-restricted
|
Built 2022 - present
|
450 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.
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
$400ks
- $500ks
The Village at Harvest Ri..., Winchester, VA
Resale Only
|
55+ age-restricted
|
Built 2005 - 2016
|
82 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
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
$600ks
- $700ks
Robinson Manor, Gainesville, VA
New Construction
|
55+ age-restricted
|
Built 2023 - present
|
50 homes
$400ks
- $500ks
Gatherings at Potomac Sta..., Leesburg, VA
New Construction
|
55+ age-restricted
|
Built 2023 - 2024
|
55 homes
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Questions? Call us:
(540) 452-4199
$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
$700ks
- $800ks
Regency at Creekside, Gainesville, VA
Resale Only
|
55+ age-restricted
|
Built 2016 - 2020
|
208 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.
$400ks
- $500ks
Abrams Chase, Winchester, VA
New Construction
|
55+ age-restricted
|
Built 2020 - present
|
13 homes
$300ks
- $400ks
JerMae Estates, Thurmont, MD
Resale Only
|
55+ age-restricted
|
Built 2003 - 2008
|
108 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
$600ks
- $700ks
Lexington 7, Ashburn, VA
Resale Only
|
55+ age-restricted
|
Built 2017 - 2020
|
113 homes
$300ks
- $400ks
Heritage Highlands, Lovettsville, VA
Resale Only
|
55+ age-restricted
|
Built 2017 - 2020
|
80 homes
$100ks
- $200ks
Albert Courts, Thurmont, MD
Resale Only
|
55+ age-restricted
|
Built 1991 - 2001
|
100 homes
Want to learn more about 55+ communities in Winchester Area?
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Questions? Call us:
(540) 452-4199
$400ks
- $600ks
The Highlands at Blue Rid..., Front Royal, VA
Resale Only
|
55+ age-restricted
|
Built 2017 - 2019
|
42 homes
$300ks
Cross Creek Village, Winchester, VA
Resale Only
|
55+ age-restricted
|
Built 2001 - 2004
|
90 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.
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 VAPW2115434 • Monument Sotheby's Internationa...
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...
Emerald Pointe
![13301 MARQUISE DR, HAGERSTOWN, MD, 21742, Hagerstown, MD 21742]()
MLS MDWA2035092 • Real Estate Innovations, Deanne...
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
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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
|1,489 sq ft
|Condo
3422 ANGELICA WAY 103, FREDERICK, MD, 21...
Community: The Woodlands of Urbana
MLS MDFR2076526 • Northrop Realty, Richard Philli...
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
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...
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.
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...
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
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
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
Bloomfields 55+
![2605 BROADLEAF DR, FREDERICK, MD, 21702, Frederick, MD 21702]()
MLS MDFR2077744 • Keller Williams Realty Centre, ...
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
Want to learn more about 55+ communities in Winchester Area?
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Questions? Call us:
(540) 452-4199
Lansdowne Woods of Virginia
![19355 CYPRESS RIDGE TER 802, LEESBURG, V..., Leesburg, VA 20176]()
3 beds
|2 baths
|1,560 sq ft
|Condo
19355 CYPRESS RIDGE TER 802, LEESBURG, V...
Community: Lansdowne Woods of Virginia
MLS VALO2114060 • Compass, Karen A Miller
The Woodlands of Urbana
![2821 CAMOMILE DR, FREDERICK, MD, 21704, Frederick, MD 21704]()
3 beds
|3 baths
|2,762 sq ft
2821 CAMOMILE DR, FREDERICK, MD, 21704
Community: The Woodlands of Urbana
MLS MDFR2077254 • Viviano Realty, Carla H Viviano
Birchwood at Brambleton
![42881 LITTLEHALES TER, ASHBURN, VA, 2014..., Ashburn, VA 20148]()
3 beds
|3 baths
|2,580 sq ft
|Condo
42881 LITTLEHALES TER, ASHBURN, VA, 2014...
Community: Birchwood at Brambleton
MLS VALO2116950 • RE/MAX Allegiance, Michael Burn...
Lansdowne Woods of Virginia
![19355 CYPRESS RIDGE TER 1122, LEESBURG, ..., Leesburg, VA 20176]()
2 beds
|2 baths
|1,038 sq ft
|Condo
19355 CYPRESS RIDGE TER 1122, LEESBURG, ...
Community: Lansdowne Woods of Virginia
MLS VALO2117156 • 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.
Trilogy® at Lake Frederick
![107 YELLOW BIRCH, LAKE FREDERICK, VA, 22..., Lake Frederick, VA 22630]()
3 beds
|5 baths
|4,465 sq ft
107 YELLOW BIRCH, LAKE FREDERICK, VA, 22...
Community: Trilogy® at Lake Frederick
MLS VAFV2039876 • HomeZu.com of Virginia, Jason P...
Trilogy® at Lake Frederick
![124 CHECKERSPOT WAY, LAKE FREDERICK, VA,..., Lake Frederick, VA 22630]()
4 beds
|4 baths
|2,508 sq ft
124 CHECKERSPOT WAY, LAKE FREDERICK, VA,...
Community: Trilogy® at Lake Frederick
MLS VAFV2039798 • Realty FC, Gloria J Ryan
The Woodlands of Urbana
![3264 STARLIGHT ST, FREDERICK, MD, 21704, Frederick, MD 21704]()
3 beds
|3 baths
|1,817 sq ft
3264 STARLIGHT ST, FREDERICK, MD, 21704
Community: The Woodlands of Urbana
MLS MDFR2077620 • Samson Properties, Hanh H Pham
Gatherings at Wellington
![9204 CHARLESTON DR 206, MANASSAS, VA, 20..., Manassas, VA 20110]()
2 beds
|2 baths
|1,558 sq ft
|Condo
9204 CHARLESTON DR 206, MANASSAS, VA, 20...
Community: Gatherings at Wellington
MLS VAMN2010332 • Keller Williams Realty/Lee Beav...
Emerald Pointe
![13428 MARQUISE DR, HAGERSTOWN, MD, 21742, Hagerstown, MD 21742]()
MLS MDWA2034456 • The KW Collective, Susan J Butt...
Trilogy® at Lake Frederick
![105 TURNSTONE LN, LAKE FREDERICK, VA, 22..., Lake Frederick, VA 22630]()
4 beds
|4 baths
|5,247 sq ft
105 TURNSTONE LN, LAKE FREDERICK, VA, 22...
Community: Trilogy® at Lake Frederick
MLS VAFV2039338 • Keller Williams Realty, Matt Bo...
Willow Run
![124 TRELLIS VIEW LN, WINCHESTER, VA, 226..., Winchester, VA 22602]()
MLS VAFV2039756 • D R Horton Realty of Virginia L...
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Abrams Chase
![105 AMBERFIELD CT, WINCHESTER, VA, 22602, Winchester, VA 22602]()
MLS VAFV2039578 • Samson Properties, Cynthia Butl...
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
![228 HYDRANGEA WAY, WINCHESTER, VA, 22602, Winchester, VA 22602]()
MLS VAFV2039560 • D R Horton Realty of Virginia L...
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
![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...
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
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, ...
Willow Run
![121 SCENTED ROSE WAY, WINCHESTER, VA, 22..., Winchester, VA 22602]()
MLS VAFV2039418 • D R Horton Realty of Virginia L...
Willow Run
![117 SCENTED ROSE WAY, WINCHESTER, VA, 22..., Winchester, VA 22602]()
MLS VAFV2039416 • D R Horton Realty of Virginia L...
Cadence at Lansdowne
![18989 CORAL REEF SQ, LEESBURG, VA, 20176, Leesburg, VA 20176]()
3 beds
|3 baths
|2,649 sq ft
18989 CORAL REEF SQ, LEESBURG, VA, 20176
Community: Cadence at Lansdowne
MLS VALO2114652 • Pearson Smith Realty, LLC, Mage...
Birchwood at Brambleton
![23630 HAVELOCK WALK TER 305, ASHBURN, VA..., Ashburn, VA 20148]()
2 beds
|2 baths
|1,060 sq ft
|Condo
23630 HAVELOCK WALK TER 305, ASHBURN, VA...
Community: Birchwood at Brambleton
MLS VALO2114614 • EXP Realty, LLC, Katherine D He...
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Rosehill Manor Villas
![13354 SNAPDRAGON WAY, HAGERSTOWN, MD, 21..., Hagerstown, MD 21742]()
3 beds
|2 baths
|1,466 sq ft
13354 SNAPDRAGON WAY, HAGERSTOWN, MD, 21...
Community: Rosehill Manor Villas
MLS MDWA2033772 • DRB Group Realty, LLC, Brittany...
Rosehill Manor Villas
![13352 SNAPDRAGON WAY, HAGERSTOWN, MD, 21..., Hagerstown, MD 21742]()
3 beds
|2 baths
|1,687 sq ft
13352 SNAPDRAGON WAY, HAGERSTOWN, MD, 21...
Community: Rosehill Manor Villas
MLS MDWA2033770 • DRB Group Realty, LLC, Brittany...
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
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 Trilogy® at Lake Frederick, Cottage Glen, Abrams Chase.
Yes, there are gated 55+ communities in the Winchester Area. Approximately 33.3% of 55+ communities in the area are gated. For instance, Trilogy® at Lake Frederick is a gated communities with 950 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 614 days. The average price of homes for sale in these communities is approximately $482,668, 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 $631,008, while homes in Cottage Glen average around $464,750.
Want to learn more about 55+ communities in the Winchester Area?
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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: May 31, 2026.
This application does not include information on all of the properties available for sale at this time.
