Call us at (540) 773-2470 to learn more about active adult communities near Winchester
Winchester, VA 55+ active adult communities & homes for sale
82 communities near Winchester
283 homes near Winchester
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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
$300Ks
- $400Ks
Cross Creek Village, Winchester, VA
Resale Only
|
55+ age-restricted
|
Built 2001 - 2004
|
90 homes
$500Ks
- $600Ks
The Village at Harvest Ri..., Winchester, VA
Resale Only
|
55+ age-restricted
|
Built 2005 - 2016
|
82 homes
$300Ks
Woodbrook Village, Winchester, VA
Resale Only
|
55+ age-restricted
|
Built 1999 - 2001
|
81 homes
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$500Ks
Abrams Chase, Winchester, VA
New Construction
|
55+ age-restricted
|
Built 2020 - present
|
13 homes
5 rating (3 reviews)
![Heritage Hunt]()
$400Ks
- $800Ks
Heritage Hunt, Gainesville, VA
Resale Only
|
55+ age-restricted
|
Built 1998 - 2009
|
1,863 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
5 rating (2 reviews)
![Potomac Green]()
$700Ks
- $800Ks
Potomac Green, Ashburn, VA
Resale Only
|
55+ age-restricted
|
Built 2005 - 2016
|
1,400 homes
5 rating (31 reviews)
![Lansdowne Woods of Virgin...]()
$200Ks
- $400Ks
Lansdowne Woods of Virgin..., Lansdowne, VA
Resale Only
|
55+ age-restricted
|
Built 1998 - 2017
|
1,200 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.
3.1 rating (7 reviews)
![Celebrate]()
$300Ks
- $600Ks
Celebrate, Fredericksburg, VA
New and Resale
|
55+ age-restricted
|
Built 2008 - present
|
1,100 homes
$200Ks
- $600Ks
Penn National, Fayetteville, PA
New and Resale
|
Age-targeted
|
Built 1968 - present
|
1,100 homes
5 rating (2 reviews)
![Trilogy® at Lake Frederic...]()
$400Ks
- $1Ms
Trilogy® at Lake Frederic..., Lake Frederick, VA
New and Resale
|
55+ age-restricted
|
Built 2006 - present
|
950 homes
5 rating (1 reviews)
![Regency at Dominion Valle...]()
$400Ks
- $700Ks
Regency at Dominion Valle..., Haymarket, VA
Resale Only
|
55+ age-restricted
|
Built 2001 - 2017
|
855 homes
5 rating (1 reviews)
![Four Seasons at Historic ...]()
$600Ks
- $700Ks
Four Seasons at Historic ..., Dumfries, VA
Resale Only
|
55+ age-restricted
|
Built 2002 - 2010
|
801 homes
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4.4 rating (5 reviews)
![Virginia Heritage at Lee'...]()
$500Ks
- $600Ks
Virginia Heritage at Lee'..., Fredericksburg, VA
Resale Only
|
55+ age-restricted
|
Built 2005 - 2021
|
795 homes
4.3 rating (3 reviews)
![Falls Run]()
$300Ks
- $400Ks
Falls Run, Fredericksburg, VA
Resale Only
|
55+ age-restricted
|
Built 2002 - 2005
|
781 homes
$600Ks
The Woodlands of Urbana, Urbana, MD
New Construction
|
55+ age-restricted
|
Built 2019 - present
|
565 homes
5 rating (1 reviews)
![Crestwood Village]()
$300Ks
Crestwood Village, Frederick, MD
Resale Only
|
55+ age-restricted
|
Built 1979 - 1999
|
550 homes
$400Ks
- $700Ks
Carter's Mill, Haymarket, VA
New Construction
|
55+ age-restricted
|
Built 2020 - present
|
480 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 rating (2 reviews)
![Dunbarton]()
$600Ks
Dunbarton, Bristow, VA
Resale Only
|
55+ age-restricted
|
Built 2000 - 2009
|
479 homes
$600Ks
- $1Ms
Montebello, Sterling, VA
New and Resale
|
55+ age-restricted
|
Built 2022 - present
|
450 homes
$300Ks
- $400Ks
Twin Lake Villas, Locust Grove, VA
New Construction
|
55+ age-restricted
|
Built 2021 - present
|
340 homes
$500Ks
- $800Ks
Spring Hill, Lorton, VA
Resale Only
|
55+ age-restricted
|
Built 2006 - 2014
|
282 homes
$400Ks
- $500Ks
Four Seasons at Charlotte..., Ruckersville, VA
Resale Only
|
55+ age-restricted
|
Built 2005 - present
|
275 homes
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Questions? Call us:
(540) 773-2470
$800Ks
- $900Ks
Regency at Ashburn, Ashburn, VA
Resale Only
|
55+ age-restricted
|
Built 2013 - 2020
|
268 homes
$400Ks
- $800Ks
ThreeOaksâ„¢, Culpeper, VA
New Construction
|
55+ age-restricted
|
Built 2024 - present
|
268 homes
$300Ks
- $400Ks
Emerald Pointe, Hagerstown, MD
New and Resale
|
55+ age-restricted
|
Built 2008 - present
|
250 homes
$500Ks
- $700Ks
River Ridge, Woodbridge, VA
Resale Only
|
55+ age-restricted
|
Built 1998 - 2002
|
238 homes
$400Ks
- $900Ks
Signature Club at Greenvi..., New Market, MD
Resale Only
|
55+ age-restricted
|
Built 2003 - 2013
|
233 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
Regency at Chancellorsvil..., Fredericksburg, VA
Resale Only
|
55+ age-restricted
|
Built 2004 - 2019
|
225 homes
$700Ks
- $900Ks
The Retreat at Poland Hil..., Chantilly, VA
Resale Only
|
55+ age-restricted
|
Built 2020 - 2022
|
219 homes
$900Ks
Regency at Creekside, Gainesville, VA
Resale Only
|
55+ age-restricted
|
Built 2016 - 2020
|
208 homes
$700Ks
The Atrium at MetroWest, Fairfax, VA
New Construction
|
55+ age-restricted
|
Built 2018 - present
|
206 homes
$400Ks
- $600Ks
Four Seasons at Virginia ..., Woodbridge, VA
New Construction
|
55+ age-restricted
|
Built 2021 - present
|
185 homes
Want to learn more about 55+ communities in Winchester?
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Questions? Call us:
(540) 773-2470
$400Ks
- $700Ks
Central Parke at Lowes Is..., Sterling, VA
Resale Only
|
55+ age-restricted
|
Built 2003 - 2005
|
181 homes
$300Ks
Summerlake, Fredericksburg, VA
Resale Only
|
55+ age-restricted
|
Built 1987 - 1997
|
161 homes
$400Ks
- $800Ks
Belmont Bay, Woodbridge, VA
New and Resale
|
Age-targeted
|
Built 2007 - present
|
155 homes
$900Ks
Regency at Belmont, Ashburn, VA
New Construction
|
55+ age-restricted
|
Built 2021 - present
|
145 homes
Spring Valley Estates
![11798 MYSTIC ROCK LN S, WAYNESBORO, PA, ..., Waynesboro, PA 17268]()
4 beds
|3 baths
|2,035 sq ft
11798 MYSTIC ROCK LN S, WAYNESBORO, PA, ...
Community: Spring Valley Estates
MLS PAFL2026870 • Real Estate Innovations, Alice ...
Spring Valley Estates
![11802 MYSTIC ROCK LN S, WAYNESBORO, PA, ..., Waynesboro, PA 17268]()
4 beds
|3 baths
|2,035 sq ft
11802 MYSTIC ROCK LN S, WAYNESBORO, PA, ...
Community: Spring Valley Estates
MLS PAFL2027046 • Real Estate Innovations, Alice ...
Spring Valley Estates
![11823 MYSTIC ROCK LN S, WAYNESBORO, PA, ..., Waynesboro, PA 17268]()
3 beds
|3 baths
|1,800 sq ft
11823 MYSTIC ROCK LN S, WAYNESBORO, PA, ...
Community: Spring Valley Estates
MLS PAFL2031032 • Real Estate Innovations, Alice ...
Spring Valley Estates
![11845 MYSTIC ROCK LN S, WAYNESBORO, PA, ..., Waynesboro, PA 17268]()
3 beds
|3 baths
|1,800 sq ft
11845 MYSTIC ROCK LN S, WAYNESBORO, PA, ...
Community: Spring Valley Estates
MLS PAFL2031024 • Real Estate Innovations, Alice ...
Spring Valley Estates
![11819 MYSTIC ROCK LN S, WAYNESBORO, PA, ..., Waynesboro, PA 17268]()
3 beds
|3 baths
|1,800 sq ft
11819 MYSTIC ROCK LN S, WAYNESBORO, PA, ...
Community: Spring Valley Estates
MLS PAFL2031030 • Real Estate Innovations, Alice ...
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New
Penn National
![6788 SAINT ANNES DR, FAYETTEVILLE, PA, 1..., Fayetteville, PA 17222]()
MLS PAFL2031404 • White Rock, Inc., Diane K Boock
Penn National
![6611 CONGRESSIONAL TER, FAYETTEVILLE, PA..., Fayetteville, PA 17222]()
MLS PAFL2029442 • Coldwell Banker Realty, Doyle C...
Penn National
![5985 GREENBRIAR TER, FAYETTEVILLE, PA, 1..., Fayetteville, PA 17222]()
MLS PAFL2029680 • White Rock, Inc., Honor A Kelle...
Country Manor
![33 LANTERN LN, SHIPPENSBURG, PA, 17257, Shippensburg, PA 17257]()
MLS PACB2048428 • Keller Williams of Central PA, ...
New
Penn National
![6396 SAUCON VALLEY DR, FAYETTEVILLE, PA,..., Fayetteville, PA 17222]()
MLS PAFL2031236 • 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.
Penn National
![6041 GREENBRIAR TER, FAYETTEVILLE, PA, 1..., Fayetteville, PA 17222]()
MLS PAFL2031250 • Berkshire Hathaway HomeServices...
Penn National
![6127 GREENBRIAR DR, FAYETTEVILLE, PA, 17..., Fayetteville, PA 17222]()
MLS PAFL2030796 • Ronnie Martin Realty, Inc., Lin...
Country Manor
![21 LANTERN LN, SHIPPENSBURG, PA, 17257, Shippensburg, PA 17257]()
MLS PACB2046792 • Coldwell Banker Realty, Kelly A...
Penn National
![3891 ALFALFA LN, FAYETTEVILLE, PA, 17222, Fayetteville, PA 17222]()
MLS PAFL2030928 • Sites Realty, Inc., David L Sit...
Country Manor
![22 LANTERN LN, SHIPPENSBURG, PA, 17257, Shippensburg, PA 17257]()
MLS PACB2043614 • Coldwell Banker Realty, Lisa Ma...
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Penn National
![6945 AUGUSTA NATIONAL, FAYETTEVILLE, PA,..., Fayetteville, PA 17222]()
MLS PAFL2028368 • Help-U-Sell Keystone Realty, LL...
Penn National
![6881 OLD COURSE RD, FAYETTEVILLE, PA, 17..., Fayetteville, PA 17222]()
MLS PAFL2029458 • Help-U-Sell Keystone Realty, LL...
Country Manor
![81 LANTERN LN, SHIPPENSBURG, PA, 17257, Shippensburg, PA 17257]()
MLS PACB2046206 • Coldwell Banker Realty, Lisa Ma...
Penn National
![3826 FARMSTEAD DR, FAYETTEVILLE, PA, 172..., Fayetteville, PA 17222]()
MLS PAFL2029312 • White Rock, Inc., Diane K Boock
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.
Penn National
![5860 FAIRWAY DR W APT 4, FAYETTEVILLE, P..., Fayetteville, PA 17222]()
2 beds
|2 baths
|1,598 sq ft
|Condo
5860 FAIRWAY DR W APT 4, FAYETTEVILLE, P...
Community: Penn National
MLS PAFL2028656 • White Rock, Inc., Diane K Boock
Penn National
![6352 PENN NATIONAL DR, CHAMBERSBURG, PA,..., Chambersburg, PA 17201]()
MLS PAFL2029838 • Sunnyhill Properties, Inc., Tan...
Penn National
![6357 9TH VW, FAYETTEVILLE, PA, 17222, Fayetteville, PA 17222]()
3 beds
|2 baths
|1,958 sq ft
|Condo
6357 9TH VW, FAYETTEVILLE, PA, 17222
Community: Penn National
MLS PAFL2025626 • White Rock, Inc., Diane K Boock
Country Manor
![84 LANTERN LN, SHIPPENSBURG, PA, 17257, Shippensburg, PA 17257]()
MLS PACB2045748 • Exit Preferred Realty, Timothy ...
Want to learn more about 55+ communities in Winchester?
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Questions? Call us:
(540) 773-2470
Lansdowne Woods of Virginia
![19385 CYPRESS RIDGE TER 914, LEESBURG, V..., Leesburg, VA 20176]()
2 beds
|2 baths
|1,509 sq ft
|Condo
19385 CYPRESS RIDGE TER 914, LEESBURG, V...
Community: Lansdowne Woods of Virginia
MLS VALO2108840 • Metropol Realty, Ali Beheshti
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 VAPW2107738 • Samson Properties, James Matthe...
Lansdowne Woods of Virginia
![19385 CYPRESS RIDGE TER UNIT 404, LEESBU..., Leesburg, VA 20176]()
2 beds
|2 baths
|1,038 sq ft
|Condo
19385 CYPRESS RIDGE TER UNIT 404, LEESBU...
Community: Lansdowne Woods of Virginia
MLS VALO2111106 • Samson Properties, Andrew M Nor...
Birchwood at Brambleton
![23688 BOLTON CRESCENT TER APT 204, ASHBU..., Ashburn, VA 20148]()
2 beds
|2 baths
|1,280 sq ft
|Condo
23688 BOLTON CRESCENT TER APT 204, ASHBU...
Community: Birchwood at Brambleton
MLS VALO2110820 • Long & Foster Real Estate, Inc....
New
Virginia Heritage at Lee's Parke
![5105 SEWELLS POINTE DR, FREDERICKSBURG, ..., Fredericksburg, VA 22407]()
4 beds
|4 baths
|4,189 sq ft
5105 SEWELLS POINTE DR, FREDERICKSBURG, ...
Community: Virginia Heritage at Lee's Parke
MLS VASP2037728 • 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.
New
Potomac Green
![20439 OLD GREY PL, ASHBURN, VA, 20147, Ashburn, VA 20147]()
MLS VALO2111424 • Long & Foster Real Estate, Inc....
New
Saintsbury Plaza
![2905 SAINTSBURY PLZ APT 312, FAIRFAX, VA..., Fairfax, VA 22031]()
3 beds
|3 baths
|1,718 sq ft
|Condo
2905 SAINTSBURY PLZ APT 312, FAIRFAX, VA...
Community: Saintsbury Plaza
MLS VAFX2279692 • Samson Properties, Dana Moore J...
Trilogy® at Lake Frederick
![108 BUNTING CT, LAKE FREDERICK, VA, 2263..., Lake Frederick, VA 22630]()
3 beds
|4 baths
|5,284 sq ft
108 BUNTING CT, LAKE FREDERICK, VA, 2263...
Community: Trilogy® at Lake Frederick
MLS VAFV2035860 • Keller Williams Realty, Matt Bo...
New
Heritage Hunt
![6920 NETHERSTONE CT, GAINESVILLE, VA, 20..., Gainesville, VA 20155]()
MLS VAPW2107960 • RLAH @properties, Candace Moe
The Retreat at Poland Hill
![43441 BETTYS FARM DR, CHANTILLY, VA, 201..., Chantilly, VA 20152]()
4 beds
|4 baths
|3,553 sq ft
43441 BETTYS FARM DR, CHANTILLY, VA, 201...
Community: The Retreat at Poland Hill
MLS VALO2110858 • Metro House, Lizzie A Helmig
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Summerlake
![11471 CHARLESTON CT, FREDERICKSBURG, VA,..., Fredericksburg, VA 22407]()
MLS VASP2036146 • Century 21 Redwood Realty, Deni...
Lansdowne Woods of Virginia
![19365 CYPRESS RIDGE TER UNIT 1102, LEESB..., Leesburg, VA 20176]()
2 beds
|2 baths
|1,105 sq ft
|Condo
19365 CYPRESS RIDGE TER UNIT 1102, LEESB...
Community: Lansdowne Woods of Virginia
MLS VALO2105996 • Keller Williams Realty, Nancy L...
Cascades at Embrey Mill
![241 SMOKEBUSH DR, STAFFORD, VA, 22554, Stafford, VA 22554]()
4 beds
|4 baths
|3,291 sq ft
|Condo
241 SMOKEBUSH DR, STAFFORD, VA, 22554
Community: Cascades at Embrey Mill
MLS VAST2043534 • Real Broker, LLC, Danny Lee Hum...
Four Seasons at Virginia Crossing
![3700 HAVERTILL LN # 1201, WOODBRIDGE, VA..., Woodbridge, VA 22193]()
2 beds
|2 baths
|1,415 sq ft
|Condo
3700 HAVERTILL LN # 1201, WOODBRIDGE, VA...
Community: Four Seasons at Virginia Crossing
MLS VAPW2105328 • Samson Properties, Christopher ...
Potomac Green
![44420 SUNSET MAPLE DR, ASHBURN, VA, 2014..., Ashburn, VA 20147]()
MLS VALO2111136 • Samson Properties, Anne Elaine ...
Frequently Asked Questions
In Winchester, there are no large communities, no medium communities, and 6 small communities with less than 500 homes.
The smallest 55+ communities in Winchester has 13 homes, the largest has 120 homes, and the average communities consists of 68 homes.
Yes, there are new 55+ homes available in Winchester. The most recent communities started in Winchester include Abrams Chase, Cottage Glen, The Village at Harvest Ridge. There are also 2 communities in Winchester that offer new construction homes, including Abrams Chase, Cottage Glen.
Yes, there is gated 55+ communities in Winchester. Approximately 16.7% of 55+ communities in the area are gated. For instance, Cottage Glen is a gated communities with 25 homes.
On average, listings in 55+ communities in Winchester stay on the market for around 534 days. The average price of homes for sale in these communities is approximately $455,982, 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 $569,950, while homes in Cottage Glen average around $479,500.
Want more information about active adult communities around Winchester?
Want to learn more about 55+ communities in Winchester?
82
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REIN updates its listings on a daily basis. Data last updated: Nov 21, 2025.
This application does not include information on all of the properties available for sale at this time.
