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
305 homes near Winchester
Sort by:
Relevance
5 rating (1 reviews)
![Willow Lawn Cottages]()
$300Ks
- $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
- $300Ks
Woodbrook Village, Winchester, VA
Resale Only
|
55+ age-restricted
|
Built 1999 - 2001
|
81 homes
$400Ks
- $400Ks
Cottage Glen, Winchester, VA
New and Resale
|
Age-targeted
|
Built 2018 - present
|
25 homes
Want to learn more about 55+ communities in Winchester?
55places can help!
Questions? Call us:
(540) 773-2470
$500Ks
- $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]()
$600Ks
- $900Ks
Potomac Green, Ashburn, VA
Resale Only
|
55+ age-restricted
|
Built 2005 - 2016
|
1,400 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
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
- $800Ks
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
- $800Ks
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
Want to learn more about 55+ communities in Winchester?
55places can help!
Questions? Call us:
(540) 773-2470
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
- $600Ks
The Woodlands of Urbana, Urbana, MD
New Construction
|
55+ age-restricted
|
Built 2019 - present
|
565 homes
5 rating (1 reviews)
![Crestwood Village]()
$300Ks
- $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
- $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
Want to learn more about 55+ communities in Winchester?
55places can help!
Questions? Call us:
(540) 773-2470
$500Ks
- $600Ks
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
- $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
- $900Ks
Regency at Creekside, Gainesville, VA
Resale Only
|
55+ age-restricted
|
Built 2016 - 2020
|
208 homes
$700Ks
- $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?
55places can help!
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
- $300Ks
Summerlake, Fredericksburg, VA
Resale Only
|
55+ age-restricted
|
Built 1987 - 1997
|
161 homes
$300Ks
- $800Ks
Belmont Bay, Woodbridge, VA
New and Resale
|
Age-targeted
|
Built 2007 - present
|
155 homes
$900Ks
- $900Ks
Regency at Belmont, Ashburn, VA
New Construction
|
55+ age-restricted
|
Built 2021 - present
|
145 homes
The Villas of Salem Church
![5711 FINLEY ROSE CT, FREDERICKSBURG, VA,..., Fredericksburg, VA 22407]()
3 beds
|3 baths
|1,762 sq ft
5711 FINLEY ROSE CT, FREDERICKSBURG, VA,...
Community: The Villas of Salem Church
MLS VASP2034276 • Century 21 Redwood Realty, CHEL...
Trilogy® at Lake Frederick
![153 LEATHER FLOWER DR, LAKE FREDERICK, V..., Lake Frederick, VA 22630]()
4 beds
|4 baths
|2,719 sq ft
153 LEATHER FLOWER DR, LAKE FREDERICK, V...
Community: Trilogy® at Lake Frederick
MLS VAFV2036644 • Coldwell Banker Realty, David A...
Country Manor
![22 LANTERN LN, SHIPPENSBURG, PA, 17257, Shippensburg, PA 17257]()
MLS PACB2043614 • Coldwell Banker Realty, Lisa Ma...
Woodbrook Village
![221 CRESTWOOD LN, WINCHESTER, VA, 22602, Winchester, VA 22602]()
MLS VAFV2037270 • ERA Oakcrest Realty, Inc., Stua...
Keswick Villas
![8816 SELBY CT, SPOTSYLVANIA, VA, 22551, Spotsylvania, VA 22551]()
MLS VASP2035620 • Coldwell Banker Elite, Leslie M...
Want to learn more about 55+ communities in Winchester?
55places can help!
Questions? Call us:
(540) 773-2470
Celebrate
![14 PENSACOLA ST, FREDERICKSBURG, VA, 224..., Fredericksburg, VA 22406]()
MLS VAST2043636 • CENTURY 21 New Millennium, Mich...
Birchwood at Brambleton
![42874 FIREFLY SONATA TER APT 107, ASHBUR..., Ashburn, VA 20148]()
2 beds
|2 baths
|1,268 sq ft
|Condo
42874 FIREFLY SONATA TER APT 107, ASHBUR...
Community: Birchwood at Brambleton
MLS VALO2108922 • Keller Williams Fairfax Gateway...
Heritage Hunt
![13879 CRABTREE WAY, GAINESVILLE, VA, 201..., Gainesville, VA 20155]()
MLS VAPW2101280 • Samson Properties, Jordan Muirh...
Lexington 7
![19873 SILVERY BLUE TER, ASHBURN, VA, 201..., Ashburn, VA 20147]()
MLS VALO2106488 • Momentum Realty LLC, Carol A Ke...
Country Manor
![81 LANTERN LN, SHIPPENSBURG, PA, 17257, Shippensburg, PA 17257]()
MLS PACB2046206 • Coldwell Banker Realty, Lisa Ma...
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
![6881 OLD COURSE RD, FAYETTEVILLE, PA, 17..., Fayetteville, PA 17222]()
MLS PAFL2029458 • Help-U-Sell Keystone Realty, LL...
Penn National
![6945 AUGUSTA NATIONAL, FAYETTEVILLE, PA,..., Fayetteville, PA 17222]()
MLS PAFL2028368 • Help-U-Sell Keystone Realty, LL...
Penn National
![3826 FARMSTEAD DR, FAYETTEVILLE, PA, 172..., Fayetteville, PA 17222]()
MLS PAFL2029312 • White Rock, Inc., Diane K Boock
Penn National
![3891 ALFALFA LN, FAYETTEVILLE, PA, 17222, Fayetteville, PA 17222]()
MLS PAFL2030928 • Sites Realty, Inc., David L Sit...
Want to learn more about 55+ communities in Winchester?
55places can help!
Questions? Call us:
(540) 773-2470
New
Spring Valley Estates
![11797 MYSTIC ROCK LN S, WAYNESBORO, PA, ..., Waynesboro, PA 17268]()
3 beds
|3 baths
|1,850 sq ft
11797 MYSTIC ROCK LN S, WAYNESBORO, PA, ...
Community: Spring Valley Estates
MLS PAFL2031076 • 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 ...
New
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
![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 ...
New
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 ...
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
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 ...
New
Spring Valley Estates
![11849 MYSTIC ROCK LN S, WAYNESBORO, PA, ..., Waynesboro, PA 17268]()
3 beds
|3 baths
|1,800 sq ft
11849 MYSTIC ROCK LN S, WAYNESBORO, PA, ...
Community: Spring Valley Estates
MLS PAFL2031028 • Real Estate Innovations, Alice ...
Country Manor
![21 LANTERN LN, SHIPPENSBURG, PA, 17257, Shippensburg, PA 17257]()
MLS PACB2046792 • Coldwell Banker Realty, Kelly A...
Want to learn more about 55+ communities in Winchester?
55places can help!
Questions? Call us:
(540) 773-2470
Penn National
![6580 FAIRWAY DR, FAYETTEVILLE, PA, 17222, Fayetteville, PA 17222]()
MLS PAFL2028530 • Coldwell Banker Realty, Tyler S...
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
![6396 SAUCON VALLEY DR, FAYETTEVILLE, PA,..., Fayetteville, PA 17222]()
MLS PAFL2027112 • Iron Valley Real Estate of Cham...
Penn National
![6127 GREENBRIAR DR, FAYETTEVILLE, PA, 17..., Fayetteville, PA 17222]()
MLS PAFL2030796 • Ronnie Martin Realty, Inc., Lin...
Penn National
![5985 GREENBRIAR TER, FAYETTEVILLE, PA, 1..., Fayetteville, PA 17222]()
MLS PAFL2029680 • White Rock, Inc., Honor A Kelle...
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
![6279 OAK LEAF LN N, FAYETTEVILLE, PA, 17..., Fayetteville, PA 17222]()
MLS PAFL2027634 • White Rock, Inc., Diane K Boock
Penn National
![3881 FARMSTEAD DR, FAYETTEVILLE, PA, 172..., Fayetteville, PA 17222]()
MLS PAFL2029672 • 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
![6611 CONGRESSIONAL TER, FAYETTEVILLE, PA..., Fayetteville, PA 17222]()
MLS PAFL2029442 • Coldwell Banker Realty, Doyle C...
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
Want to learn more about 55+ communities in Winchester?
55places can help!
Questions? Call us:
(540) 773-2470
Country Manor
![84 LANTERN LN, SHIPPENSBURG, PA, 17257, Shippensburg, PA 17257]()
MLS PACB2045748 • Exit Preferred Realty, Timothy ...
New
The Woodlands of Urbana
![3225 THORNAPPLE DR, FREDERICK, MD, 21704, Frederick, MD 21704]()
3 beds
|3 baths
|1,816 sq ft
3225 THORNAPPLE DR, FREDERICK, MD, 21704
Community: The Woodlands of Urbana
MLS MDFR2071582 • IMPACT Maryland Real Estate, St...
New
Crestwood Village
![7006 ARBOR DR, FREDERICK, MD, 21703, Frederick, MD 21703]()
MLS MDFR2073074 • Maryland Elite Realtors, Cassan...
The Village at Foxfield
![3 KELLER LN, MIDDLETOWN, MD, 21769, Middletown, MD 21769]()
3 beds
|4 baths
|2,267 sq ft
3 KELLER LN, MIDDLETOWN, MD, 21769
Community: The Village at Foxfield
MLS MDFR2072380 • RE/MAX Results, Margaret A Magn...
New
Signature Club at Greenview
![10611 VICTORIAN AVE 51, NEW MARKET, MD, ..., New Market, MD 21774]()
3 beds
|3 baths
|2,200 sq ft
10611 VICTORIAN AVE 51, NEW MARKET, MD, ...
Community: Signature Club at Greenview
MLS MDFR2072800 • Berkshire Hathaway HomeServices...
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
communities
near Winchester
Remove Boundaries ×
Map
Satellite
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.
© 2025 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: Nov 08, 2025.
This application does not include information on all of the properties available for sale at this time.
