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
299 homes near Winchester
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5 rating (1 reviews)
![Willow Lawn Cottages]()
$300Ks
- $300Ks
Willow Lawn Cottages, Winchester, VA
Resale Only
|
55+ age-restricted
|
Built 1999 - 2004
|
120 homes
No reviews yet
![Cross Creek Village]()
$300Ks
- $400Ks
Cross Creek Village, Winchester, VA
Resale Only
|
55+ age-restricted
|
Built 2001 - 2004
|
90 homes
No reviews yet
![The Village at Harvest Ri...]()
$500Ks
- $600Ks
The Village at Harvest Ri..., Winchester, VA
Resale Only
|
55+ age-restricted
|
Built 2005 - 2016
|
82 homes
No reviews yet
![Woodbrook Village]()
$300Ks
- $300Ks
Woodbrook Village, Winchester, VA
Resale Only
|
55+ age-restricted
|
Built 1999 - 2001
|
81 homes
No reviews yet
![Cottage Glen]()
$400Ks
- $400Ks
Cottage Glen, Winchester, VA
New and Resale
|
Age-targeted
|
Built 2018 - present
|
25 homes
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No reviews yet
![Abrams Chase]()
$500Ks
- $500Ks
Abrams Chase, Winchester, VA
New Construction
|
55+ age-restricted
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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...]()
$300Ks
- $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
No reviews yet
![Penn National]()
$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
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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
No reviews yet
![The Woodlands of Urbana]()
$600Ks
- $700Ks
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
No reviews yet
![Carter's Mill]()
$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
No reviews yet
![Montebello]()
$600Ks
- $1Ms
Montebello, Sterling, VA
New and Resale
|
55+ age-restricted
|
Built 2022 - present
|
450 homes
No reviews yet
![Twin Lake Villas]()
$400Ks
- $400Ks
Twin Lake Villas, Locust Grove, VA
New Construction
|
55+ age-restricted
|
Built 2021 - present
|
340 homes
No reviews yet
![Spring Hill]()
$500Ks
- $800Ks
Spring Hill, Lorton, VA
Resale Only
|
55+ age-restricted
|
Built 2006 - 2014
|
282 homes
No reviews yet
![Four Seasons at Charlotte...]()
$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:
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No reviews yet
![Regency at Ashburn]()
$500Ks
- $600Ks
Regency at Ashburn, Ashburn, VA
Resale Only
|
55+ age-restricted
|
Built 2013 - 2020
|
268 homes
No reviews yet
![ThreeOaksâ„¢]()
$400Ks
- $800Ks
ThreeOaksâ„¢, Culpeper, VA
New Construction
|
55+ age-restricted
|
Built 2024 - present
|
268 homes
No reviews yet
![Emerald Pointe]()
$300Ks
- $400Ks
Emerald Pointe, Hagerstown, MD
New and Resale
|
55+ age-restricted
|
Built 2008 - present
|
250 homes
No reviews yet
![River Ridge]()
$600Ks
- $600Ks
River Ridge, Woodbridge, VA
Resale Only
|
55+ age-restricted
|
Built 1998 - 2002
|
238 homes
No reviews yet
![Signature Club at Greenvi...]()
$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.
No reviews yet
![Regency at Chancellorsvil...]()
$400Ks
- $400Ks
Regency at Chancellorsvil..., Fredericksburg, VA
Resale Only
|
55+ age-restricted
|
Built 2004 - 2019
|
225 homes
No reviews yet
![The Retreat at Poland Hil...]()
$700Ks
- $900Ks
The Retreat at Poland Hil..., Chantilly, VA
Resale Only
|
55+ age-restricted
|
Built 2020 - 2022
|
219 homes
No reviews yet
![Regency at Creekside]()
$900Ks
- $900Ks
Regency at Creekside, Gainesville, VA
Resale Only
|
55+ age-restricted
|
Built 2016 - 2020
|
208 homes
No reviews yet
![The Atrium at MetroWest]()
$700Ks
- $800Ks
The Atrium at MetroWest, Fairfax, VA
New Construction
|
55+ age-restricted
|
Built 2018 - present
|
206 homes
No reviews yet
![Four Seasons at Virginia ...]()
$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
No reviews yet
![Central Parke at Lowes Is...]()
$400Ks
- $700Ks
Central Parke at Lowes Is..., Sterling, VA
Resale Only
|
55+ age-restricted
|
Built 2003 - 2005
|
181 homes
No reviews yet
![Summerlake]()
$300Ks
- $300Ks
Summerlake, Fredericksburg, VA
Resale Only
|
55+ age-restricted
|
Built 1987 - 1997
|
161 homes
No reviews yet
![Belmont Bay]()
$300Ks
- $800Ks
Belmont Bay, Woodbridge, VA
New and Resale
|
Age-targeted
|
Built 2007 - present
|
155 homes
No reviews yet
![Regency at Belmont]()
$900Ks
- $900Ks
Regency at Belmont, Ashburn, VA
New Construction
|
55+ age-restricted
|
Built 2021 - present
|
145 homes
No reviews yet
![Spring Valley Estates]()
$300Ks
- $300Ks
Spring Valley Estates, Waynesboro, PA
New Construction
|
55+ age-restricted
|
Built 2019 - present
|
140 homes
Penn National
![6945 AUGUSTA NATIONAL, FAYETTEVILLE, PA,..., Fayetteville, PA 17222]()
MLS PAFL2028368 • Help-U-Sell Keystone Realty, LL...
Country Manor
![38 LANTERN LN, SHIPPENSBURG, PA, 17257, Shippensburg, PA 17257]()
MLS PACB2043784 • BrokersRealty.com, John A Rainv...
Country Manor
![21 LANTERN LN, SHIPPENSBURG, PA, 17257, Shippensburg, PA 17257]()
MLS PACB2046792 • Coldwell Banker Realty, Kelly A...
Penn National
![6396 SAUCON VALLEY DR, FAYETTEVILLE, PA,..., Fayetteville, PA 17222]()
MLS PAFL2027112 • Iron Valley Real Estate of Cham...
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Questions? Call us:
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Penn National
![6127 GREENBRIAR DR, FAYETTEVILLE, PA, 17..., Fayetteville, PA 17222]()
MLS PAFL2030796 • Ronnie Martin Realty, Inc., Lin...
Penn National
![6881 OLD COURSE RD, FAYETTEVILLE, PA, 17..., Fayetteville, PA 17222]()
MLS PAFL2029458 • Help-U-Sell Keystone Realty, LL...
Penn National
![5985 GREENBRIAR TER, FAYETTEVILLE, PA, 1..., Fayetteville, PA 17222]()
MLS PAFL2029680 • White Rock, Inc., Honor A Kelle...
Penn National
![6580 FAIRWAY DR, FAYETTEVILLE, PA, 17222, Fayetteville, PA 17222]()
MLS PAFL2028530 • Coldwell Banker Realty, Tyler S...
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.
Country Manor
![22 LANTERN LN, SHIPPENSBURG, PA, 17257, Shippensburg, PA 17257]()
MLS PACB2043614 • Coldwell Banker Realty, Lisa Ma...
Courts of Clarksburg
![832 BUTTERFLY WEED DR, GERMANTOWN, MD, 2..., Germantown, MD 20876]()
2 beds
|3 baths
|2,784 sq ft
832 BUTTERFLY WEED DR, GERMANTOWN, MD, 2...
Community: Courts of Clarksburg
MLS MDMC2205084 • RE/MAX Realty Group, Jeffrey A ...
Crestwood Village
![7043 BASSWOOD RD, FREDERICK, MD, 21703, Frederick, MD 21703]()
MLS MDFR2072192 • Keller Williams Capital Propert...
The Village at Cabin Branch
![13504 GOLDENEYE CIR, CLARKSBURG, MD, 208..., Clarksburg, MD 20871]()
3 beds
|3 baths
|1,590 sq ft
13504 GOLDENEYE CIR, CLARKSBURG, MD, 208...
Community: The Village at Cabin Branch
MLS MDMC2204722 • King Real Estate, Inc, David N ...
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Gatherings at Cabin Branch
![13504 GOLDENEYE CIR, CLARKSBURG, MD, 208..., Clarksburg, MD 20871]()
3 beds
|3 baths
|1,590 sq ft
13504 GOLDENEYE CIR, CLARKSBURG, MD, 208...
Community: Gatherings at Cabin Branch
MLS MDMC2204722 • King Real Estate, Inc, David N ...
Emerald Pointe
![13323 DIAMOND POINTE DR, HAGERSTOWN, MD,..., Hagerstown, MD 21742]()
2 beds
|2 baths
|1,884 sq ft
13323 DIAMOND POINTE DR, HAGERSTOWN, MD,...
Community: Emerald Pointe
MLS MDWA2031676 • RE/MAX Results, Jeanine K McVic...
Courts of Clarksburg
![21822 BONESET WAY, GERMANTOWN, MD, 20876, Germantown, MD 20876]()
3 beds
|2 baths
|1,540 sq ft
21822 BONESET WAY, GERMANTOWN, MD, 20876
Community: Courts of Clarksburg
MLS MDMC2201378 • Open Door Brokerage, LLC, Verri...
The Woodlands of Urbana
![3207 THORNAPPLE DR, FREDERICK, MD, 21704, Frederick, MD 21704]()
3 beds
|2 baths
|1,677 sq ft
3207 THORNAPPLE DR, FREDERICK, MD, 21704
Community: The Woodlands of Urbana
MLS MDFR2070158 • Long & Foster Real Estate, Inc....
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 MDFR2071176 • Long & Foster Real Estate, Inc....
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.
Signature Club at Greenview
![10816 DEWEY WAY, NEW MARKET, MD, 21774, New Market, MD 21774]()
4 beds
|4 baths
|2,550 sq ft
10816 DEWEY WAY, NEW MARKET, MD, 21774
Community: Signature Club at Greenview
MLS MDFR2071278 • The Agency DC, Brandi J Dillon
Signature Club at Greenview
![5810 WHITEROSE WAY, NEW MARKET, MD, 2177..., New Market, MD 21774]()
3 beds
|4 baths
|2,410 sq ft
5810 WHITEROSE WAY, NEW MARKET, MD, 2177...
Community: Signature Club at Greenview
MLS MDFR2072088 • Century 21 Redwood Realty, Mich...
Signature Club at Greenview
![5948 JACOBEAN PL, NEW MARKET, MD, 21774, New Market, MD 21774]()
3 beds
|3 baths
|3,123 sq ft
|Condo
5948 JACOBEAN PL, NEW MARKET, MD, 21774
Community: Signature Club at Greenview
MLS MDFR2070368 • Long & Foster Real Estate, Inc....
Courts of Clarksburg
![825 BUTTERFLY WEED DR, GERMANTOWN, MD, 2..., Germantown, MD 20876]()
2 beds
|2 baths
|1,806 sq ft
825 BUTTERFLY WEED DR, GERMANTOWN, MD, 2...
Community: Courts of Clarksburg
MLS MDMC2186880 • Compass, VJ Derbarghamian
The Woodlands of Urbana
![2928 HERB GARDEN DR, FREDERICK, MD, 2170..., Frederick, MD 21704]()
3 beds
|4 baths
|3,634 sq ft
2928 HERB GARDEN DR, FREDERICK, MD, 2170...
Community: The Woodlands of Urbana
MLS MDFR2070902 • LPT Realty, LLC, Eric Steinhoff
Want to learn more about 55+ communities in Winchester?
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CobbleStone Estates
![9616 COBBLE STONE CT, HAGERSTOWN, MD, 21..., Hagerstown, MD 21740]()
2 beds
|2 baths
|1,561 sq ft
9616 COBBLE STONE CT, HAGERSTOWN, MD, 21...
Community: CobbleStone Estates
MLS MDWA2029174 • Blackwell Real Estate, LLC, Che...
Emerald Pointe
![19446 SAPPHIRE DR, HAGERSTOWN, MD, 21742, Hagerstown, MD 21742]()
MLS MDWA2027286 • Coldwell Banker Realty, Jody Le...
Emerald Pointe
![13336 MARQUISE DR, HAGERSTOWN, MD, 21742, Hagerstown, MD 21742]()
MLS MDWA2029356 • Century 21 Market Professionals...
Gatherings at Cabin Branch
![13444 PETREL ST, CLARKSBURG, MD, 20871, Clarksburg, MD 20871]()
3 beds
|3 baths
|1,933 sq ft
13444 PETREL ST, CLARKSBURG, MD, 20871
Community: Gatherings at Cabin Branch
MLS MDMC2200864 • RE/MAX Results, Bobbi Prescott
The Village at Cabin Branch
![13444 PETREL ST, CLARKSBURG, MD, 20871, Clarksburg, MD 20871]()
3 beds
|3 baths
|1,933 sq ft
13444 PETREL ST, CLARKSBURG, MD, 20871
Community: The Village at Cabin Branch
MLS MDMC2200864 • RE/MAX Results, Bobbi Prescott
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.
Emerald Pointe
![13430 MARQUISE DR # 80, HAGERSTOWN, MD, ..., Hagerstown, MD 21742]()
2 beds
|3 baths
|2,739 sq ft
13430 MARQUISE DR # 80, HAGERSTOWN, MD, ...
Community: Emerald Pointe
MLS MDWA2028292 • Sullivan Select, LLC., Cynthia ...
The Village at Cabin Branch
![13240 PETREL ST # 106, CLARKSBURG, MD, 2..., Clarksburg, MD 20871]()
1 beds
|1 baths
|1,203 sq ft
|Condo
13240 PETREL ST # 106, CLARKSBURG, MD, 2...
Community: The Village at Cabin Branch
MLS MDMC2173752 • Keller Williams Realty Centre, ...
Gatherings at Cabin Branch
![13240 PETREL ST # 106, CLARKSBURG, MD, 2..., Clarksburg, MD 20871]()
1 beds
|1 baths
|1,203 sq ft
|Condo
13240 PETREL ST # 106, CLARKSBURG, MD, 2...
Community: Gatherings at Cabin Branch
MLS MDMC2173752 • Keller Williams Realty Centre, ...
Signature Club at Greenview
![5816 DREXAL AVE, NEW MARKET, MD, 21774, New Market, MD 21774]()
5 beds
|4 baths
|4,926 sq ft
5816 DREXAL AVE, NEW MARKET, MD, 21774
Community: Signature Club at Greenview
MLS MDFR2069638 • Blue Crab Real Estate, LLC., Da...
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(540) 773-2470
Signature Club at Greenview
![5909 CONSTANCE WAY, NEW MARKET, MD, 2177..., New Market, MD 21774]()
3 beds
|3 baths
|2,599 sq ft
|Condo
5909 CONSTANCE WAY, NEW MARKET, MD, 2177...
Community: Signature Club at Greenview
MLS MDFR2071060 • Long & Foster Real Estate, Inc....
The Woodlands of Urbana
![3272 PINE NEEDLE CIR UNIT 202, FREDERICK..., Frederick, MD 21704]()
2 beds
|2 baths
|Condo
3272 PINE NEEDLE CIR UNIT 202, FREDERICK...
Community: The Woodlands of Urbana
MLS MDFR2070678 • EXP Realty, LLC, Karen D Rollin...
Gatherings at Cabin Branch
![13230 PETREL ST UNIT 2208, CLARKSBURG, M..., Clarksburg, MD 20871]()
2 beds
|2 baths
|1,702 sq ft
|Condo
13230 PETREL ST UNIT 2208, CLARKSBURG, M...
Community: Gatherings at Cabin Branch
MLS MDMC2195710 • Keller Williams Realty Centre, ...
The Village at Cabin Branch
![13230 PETREL ST UNIT 2208, CLARKSBURG, M..., Clarksburg, MD 20871]()
2 beds
|2 baths
|1,702 sq ft
|Condo
13230 PETREL ST UNIT 2208, CLARKSBURG, M...
Community: The Village at Cabin Branch
MLS MDMC2195710 • Keller Williams Realty Centre, ...
Gatherings at Cabin Branch
![13230 PETREL ST UNIT 2104, CLARKSBURG, M..., Clarksburg, MD 20871]()
2 beds
|2 baths
|1,529 sq ft
|Condo
13230 PETREL ST UNIT 2104, CLARKSBURG, M...
Community: Gatherings at Cabin Branch
MLS MDMC2195706 • Keller Williams Realty Centre, ...
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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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: Oct 27, 2025.
This application does not include information on all of the properties available for sale at this time.
