Call us at (860) 238-3620 to learn more about active adult communities near Winchester Area
Winchester Area, CT 55+ active adult communities & homes for sale
89 communities near Winchester Area
234 homes near Winchester Area
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![Clockmaker's Hill]()
$100Ks
- $100Ks
Clockmaker's Hill, Winsted, CT
Resale Only
|
55+ age-restricted
|
Built 2005 - 2014
|
38 homes
No reviews yet
![Oak Meadow Estates]()
$200Ks
- $400Ks
Oak Meadow Estates, Torrington, CT
New and Resale
|
55+ age-restricted
|
Built 2013 - present
|
31 homes
3 rating (2 reviews)
![Heritage Hills]()
$300Ks
- $900Ks
Heritage Hills, Somers, NY
Resale Only
|
Age-targeted
|
Built 1974 - 2006
|
2,600 homes
3.6 rating (7 reviews)
![Heritage Village]()
$100Ks
- $400Ks
Heritage Village, Southbury, CT
Resale Only
|
55+ age-restricted
|
Built 1967 - 2005
|
2,580 homes
No reviews yet
![Leisure Village]()
$200Ks
- $500Ks
Leisure Village, Ridge, NY
Resale Only
|
55+ age-restricted
|
Built 1969 - 1986
|
1,500 homes
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No reviews yet
![Rivington]()
$500Ks
- $900Ks
Rivington, Danbury, CT
New and Resale
|
Age-targeted
|
Built 2006 - present
|
1,050 homes
4 rating (1 reviews)
![Jefferson Village]()
$200Ks
- $500Ks
Jefferson Village, Yorktown Heights, NY
Resale Only
|
55+ age-restricted
|
Built 1967 - 1982
|
1,000 homes
No reviews yet
![Oronoque Village]()
$300Ks
- $600Ks
Oronoque Village, Stratford, CT
Resale Only
|
55+ age-restricted
|
Built 1971 - 1977
|
929 homes
No reviews yet
![The Village at Oxford Gre...]()
$500Ks
- $700Ks
The Village at Oxford Gre..., Oxford, CT
New and Resale
|
55+ age-restricted
|
Built 2004 - present
|
835 homes
No reviews yet
![Leisure Knoll]()
$200Ks
- $400Ks
Leisure Knoll, Ridge, NY
Resale Only
|
55+ age-restricted
|
Built 1972 - 1982
|
701 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
![Leisure Glen]()
$400Ks
- $500Ks
Leisure Glen, Ridge, NY
Resale Only
|
55+ age-restricted
|
Built 1985 - 2010
|
646 homes
No reviews yet
![Spring Lake Village]()
$200Ks
- $300Ks
Spring Lake Village, Southington, CT
Resale Only
|
55+ age-restricted
|
Built 1970 - 2004
|
640 homes
4 rating (8 reviews)
![Glenwood Village]()
$100Ks
- $400Ks
Glenwood Village, Riverhead, NY
New and Resale
|
55+ age-restricted
|
Built 1959 - present
|
588 homes
No reviews yet
![Regency at Prospect]()
$400Ks
- $400Ks
Regency at Prospect, Prospect, CT
Resale Only
|
55+ age-restricted
|
Built 2006 - 2020
|
379 homes
No reviews yet
![The Retreat at Carmel]()
$400Ks
- $600Ks
The Retreat at Carmel, Carmel, NY
Resale Only
|
55+ age-restricted
|
Built 2008 - 2018
|
312 homes
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Questions? Call us:
(860) 238-3620
3.5 rating (2 reviews)
![Foxwood Village]()
$300Ks
- $400Ks
Foxwood Village, Calverton, NY
Resale Only
|
55+ age-restricted
|
Built 1986 - 2007
|
294 homes
1 rating (1 reviews)
![Plymouth Estates at Mount...]()
$500Ks
- $500Ks
Plymouth Estates at Mount..., Mount Sinai, NY
Resale Only
|
55+ age-restricted
|
Built 2006 - 2013
|
285 homes
No reviews yet
![Meadow Brook Estates]()
$500Ks
- $500Ks
Meadow Brook Estates, Oxford, CT
Resale Only
|
55+ age-restricted
|
Built 2003 - 2020
|
246 homes
No reviews yet
![The Summit at Bethel]()
$600Ks
- $600Ks
The Summit at Bethel, Bethel, CT
Resale Only
|
55+ age-restricted
|
Built 2010 - 2021
|
235 homes
4.9 rating (14 reviews)
![Chatfield Farms]()
$500Ks
- $500Ks
Chatfield Farms, Beacon Falls, CT
New Construction
|
55+ age-restricted
|
Built 2014 - present
|
231 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
![Woodridge Strathmore Terr...]()
$400Ks
- $400Ks
Woodridge Strathmore Terr..., Mount Sinai, NY
Resale Only
|
55+ age-restricted
|
Built 1974 - 1985
|
226 homes
No reviews yet
![Regency at Wappinger]()
$600Ks
- $700Ks
Regency at Wappinger, Wappingers Falls, NY
Resale Only
|
55+ age-restricted
|
Built 2014 - 2020
|
225 homes
No reviews yet
![Saddle Lakes]()
$400Ks
- $400Ks
Saddle Lakes, Riverhead, NY
Resale Only
|
55+ age-restricted
|
Built 2000 - 2002
|
196 homes
5 rating (1 reviews)
![Sunken Pond Estates]()
$400Ks
- $500Ks
Sunken Pond Estates, Riverhead, NY
Resale Only
|
55+ age-restricted
|
Built 2003 - 2005
|
194 homes
5 rating (1 reviews)
![The Villages at Mount Sin...]()
$700Ks
- $800Ks
The Villages at Mount Sin..., Mount Sinai, NY
Resale Only
|
55+ age-restricted
|
Built 2005 - 2007
|
185 homes
Want to learn more about 55+ communities in Winchester Area?
55places can help!
Questions? Call us:
(860) 238-3620
No reviews yet
![The Powder Forest Homes]()
$600Ks
- $700Ks
The Powder Forest Homes, Simsbury, CT
Resale Only
|
55+ age-restricted
|
Built 2006 - 2016
|
182 homes
5 rating (1 reviews)
![Newtown Woods]()
$400Ks
- $500Ks
Newtown Woods, Newtown, CT
New and Resale
|
55+ age-restricted
|
Built 2011 - present
|
178 homes
No reviews yet
![Stoneleigh Woods at River...]()
$400Ks
- $600Ks
Stoneleigh Woods at River..., Riverhead, NY
Resale Only
|
55+ age-restricted
|
Built 2007 - 2016
|
176 homes
No reviews yet
![Beckley Farms]()
$300Ks
- $400Ks
Beckley Farms, Berlin, CT
New and Resale
|
55+ age-restricted
|
Built 2010 - present
|
170 homes
No reviews yet
![Regency at Fishkill]()
$500Ks
- $500Ks
Regency at Fishkill, Fishkill, NY
Resale Only
|
55+ age-restricted
|
Built 2008 - 2020
|
164 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
![South Pond Village]()
$200Ks
- $400Ks
South Pond Village, Bloomfield, CT
Resale Only
|
55+ age-restricted
|
Built 1999 - 2005
|
151 homes
No reviews yet
![Setauket Meadows]()
$600Ks
- $700Ks
Setauket Meadows, Setauket, NY
Resale Only
|
55+ age-restricted
|
Built 2005 - 2007
|
150 homes
No reviews yet
![Fieldstone Village]()
$500Ks
- $800Ks
Fieldstone Village, Orange, CT
Resale Only
|
55+ age-restricted
|
Built 2010 - 2018
|
142 homes
No reviews yet
![North Woods of Colchester]()
$300Ks
- $400Ks
North Woods of Colchester, Colchester, CT
New and Resale
|
55+ age-restricted
|
Built 2007 - present
|
140 homes
No reviews yet
![Windcrest East]()
$600Ks
- $600Ks
Windcrest East, Calverton, NY
Resale Only
|
55+ age-restricted
|
Built 2004 - 2005
|
126 homes
Want to learn more about 55+ communities in Winchester Area?
55places can help!
Questions? Call us:
(860) 238-3620
No reviews yet
![Fairview at Oxford Greens]()
$500Ks
- $700Ks
Fairview at Oxford Greens, Oxford, CT
New and Resale
|
55+ age-restricted
|
Built 2019 - present
|
125 homes
3.5 rating (2 reviews)
![Harvest Pointe]()
$800Ks
- $3Ms
Harvest Pointe, Cutchogue, NY
New Construction
|
55+ age-restricted
|
Built 2017 - present
|
124 homes
No reviews yet
![Newbury Village]()
$600Ks
- $700Ks
Newbury Village, Brookfield, CT
New and Resale
|
55+ age-restricted
|
Built 2005 - present
|
120 homes
No reviews yet
![The Gardens of Wilbraham]()
$300Ks
- $400Ks
The Gardens of Wilbraham, Wilbraham, MA
New and Resale
|
55+ age-restricted
|
Built 2005 - present
|
108 homes
No reviews yet
![O'Meara Farm]()
$400Ks
- $500Ks
O'Meara Farm, Farmington, CT
Resale Only
|
55+ age-restricted
|
Built 1998 - 2005
|
104 homes
Leisure Village
![273 BERWICK CT B, RIDGE, NY, 11961, Ridge, NY 11961]()
MLS 885024 • Pinpoint Realty LI, Marc V. Kaplan
Heritage Hills
![682 HERITAGE HLS C, SOMERS, NY, 10589, Somers, NY 10589]()
3 beds
|2 baths
|2,030 sq ft
|Condo
682 HERITAGE HLS C, SOMERS, NY, 10589
Community: Heritage Hills
MLS 891807 • Houlihan Lawrence Inc., Donna O'Conn...
Regency at Fishkill
![326 REGENCY DR, FISHKILL, NY, 12524, Fishkill, NY 12524]()
1 beds
|2 baths
|1,543 sq ft
|Condo
326 REGENCY DR, FISHKILL, NY, 12524
Community: Regency at Fishkill
MLS 890462 • RE/MAX Town & Country, Spyros Spyrou
Leisure Glen
![293 GLEN DR, RIDGE, NY, 11961, Ridge, NY 11961]()
MLS 894371 • Howard Hanna Coach, Kalliopi C. Suar...
Leisure Village
![191 VENTRY CT D, RIDGE, NY, 11961, Ridge, NY 11961]()
MLS 894142 • Realty Connect USA L I Inc, Sharon A...
Want to learn more about 55+ communities in Winchester Area?
55places can help!
Questions? Call us:
(860) 238-3620
Leisure Village
![96 ENFIELD CT B, RIDGE, NY, 11961, Ridge, NY 11961]()
MLS 877572 • Compass Greater NY LLC, Kenneth Hirs...
The Retreat at Carmel
![31 LANGDON GROVE, CARMEL, NY, 10512, Carmel, NY 10512]()
2 beds
|2 baths
|1,979 sq ft
|House
31 LANGDON GROVE, CARMEL, NY, 10512
Community: The Retreat at Carmel
MLS 877918 • Compass Greater NY, LLC, Dorianne C....
Heritage Hills
![15 HERITAGE HLS A, SOMERS, NY, 10589, Somers, NY 10589]()
2 beds
|2 baths
|1,139 sq ft
|Condo
15 HERITAGE HLS A, SOMERS, NY, 10589
Community: Heritage Hills
MLS 891829 • Howard Hanna Rand Realty, Theresa A....
Leisure Village
![404B WOODBRIDGE DR 404B, BROOKHAVEN, NY,..., Brookhaven, NY 11961]()
2 beds
|1 baths
|907 sq ft
|Condo
404B WOODBRIDGE DR 404B, BROOKHAVEN, NY,...
Community: Leisure Village
MLS 867426 • Leisure Living Realty Inc, Laura Ruh...
Leisure Village
![164 FALMOUTH CT E, RIDGE, NY, 11961, Ridge, NY 11961]()
MLS 893757 • Douglas Elliman Real Estate, Joseph ...
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.
Jefferson Village
![156 CARRIAGE CT G, YORKTOWN HEIGHTS, NY,..., Yorktown Heights, NY 10598]()
1 beds
|1 baths
|850 sq ft
|Condo
156 CARRIAGE CT G, YORKTOWN HEIGHTS, NY,...
Community: Jefferson Village
MLS 823393 • Houlihan Lawrence Inc., Nancy Kenned...
Leisure Village
![384 WOODBRIDGE DR A, RIDGE, NY, 11961, Ridge, NY 11961]()
2 beds
|2 baths
|1,200 sq ft
|Condo
384 WOODBRIDGE DR A, RIDGE, NY, 11961
Community: Leisure Village
MLS 894462 • Coldwell Banker M&D Good Life, Micha...
The Villages at Mount Sinai Park
![4 OAKHURST CT, MOUNT SINAI, NY, 11766, Mount Sinai, NY 11766]()
3 beds
|3 baths
|2,850 sq ft
|Condo
4 OAKHURST CT, MOUNT SINAI, NY, 11766
Community: The Villages at Mount Sinai Park
MLS 856049 • Douglas Elliman Real Estate, Lisa A....
Leisure Village
![247 NEWCASTLE CT A, RIDGE, NY, 11961, Ridge, NY 11961]()
2 beds
|2 baths
|1,564 sq ft
|Condo
247 NEWCASTLE CT A, RIDGE, NY, 11961
Community: Leisure Village
MLS 891459 • Charles Rutenberg Realty Inc, Marzen...
Leisure Knoll
![193 BERKSHIRE DR, RIDGE, NY, 11961, Ridge, NY 11961]()
MLS 891997 • Coldwell Banker American Homes, Joan...
Want to learn more about 55+ communities in Winchester Area?
55places can help!
Questions? Call us:
(860) 238-3620
Jefferson Village
![165 CARRIAGE CT H, YORKTOWN HEIGHTS, NY,..., Yorktown Heights, NY 10598]()
2 beds
|2 baths
|1,167 sq ft
|Condo
165 CARRIAGE CT H, YORKTOWN HEIGHTS, NY,...
Community: Jefferson Village
MLS 869428 • Julia B Fee Sothebys Int. Rlty, Nich...
Heritage Hills
![348 HERITAGE HLS A, SOMERS, NY, 10589, Somers, NY 10589]()
2 beds
|2 baths
|1,428 sq ft
|Condo
348 HERITAGE HLS A, SOMERS, NY, 10589
Community: Heritage Hills
MLS 866206 • William Raveis-New York, LLC, Cynthi...
Leisure Knoll
![190 CANTERBURY DR, RIDGE, NY, 11961, Ridge, NY 11961]()
MLS 863784 • Coldwell Banker American Homes, Bonn...
Leisure Village
![75A ENFIELD CT 75A, BROOKHAVEN, NY, 1196..., Brookhaven, NY 11961]()
2 beds
|1 baths
|1,278 sq ft
|Condo
75A ENFIELD CT 75A, BROOKHAVEN, NY, 1196...
Community: Leisure Village
MLS 867044 • Leisure Living Realty Inc, Laura Ruh...
Jefferson Village
![6 DEVON CT B, YORKTOWN HEIGHTS, NY, 1059..., Yorktown Heights, NY 10598]()
2 beds
|1 baths
|1,000 sq ft
|Condo
6 DEVON CT B, YORKTOWN HEIGHTS, NY, 1059...
Community: Jefferson Village
MLS 865906 • Keller Williams Realty Partner, Rose...
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.
Glenwood Village
![1661 OLD COUNTRY RD 120, RIVERHEAD, NY, ..., Riverhead, NY 11901]()
2 beds
|2 baths
|1,344 sq ft
|Manufactured Home
1661 OLD COUNTRY RD 120, RIVERHEAD, NY, ...
Community: Glenwood Village
MLS 890746 • Joanne Kane Gigantiello, Joanne Giga...
Jefferson Village
![32 CAMBRIDGE CT A, YORKTOWN HEIGHTS, NY,..., Yorktown Heights, NY 10598]()
2 beds
|1 baths
|951 sq ft
|Condo
32 CAMBRIDGE CT A, YORKTOWN HEIGHTS, NY,...
Community: Jefferson Village
MLS 850166 • Real Broker NY LLC, Dani Dorman
Leisure Village
![269 BERWICK CT B, RIDGE, NY, 11961, Ridge, NY 11961]()
2 beds
|1 baths
|1,048 sq ft
|Condo
269 BERWICK CT B, RIDGE, NY, 11961
Community: Leisure Village
MLS 856130 • Oversouth LLC, Deniz Ozgur
Glenwood Village
![1661 OLD COUNTRY RD 308, RIVERHEAD, NY, ..., Riverhead, NY 11901]()
2 beds
|1 baths
|840 sq ft
|Mobile Home
1661 OLD COUNTRY RD 308, RIVERHEAD, NY, ...
Community: Glenwood Village
MLS L3583691 • Realty Connect USA L I Inc, Fengxi...
Jefferson Village
![27 WALDEN CT APT A A, YORKTOWN HEIGHTS, ..., Yorktown Heights, NY 10598]()
|
1 baths
|550 sq ft
|Condo
27 WALDEN CT APT A A, YORKTOWN HEIGHTS, ...
Community: Jefferson Village
MLS 888092 • Prime Site Realty Exq Homes, Luigi L...
Want to learn more about 55+ communities in Winchester Area?
55places can help!
Questions? Call us:
(860) 238-3620
Leisure Village
![192 VENTRY CT A, RIDGE, NY, 11961, Ridge, NY 11961]()
MLS 867626 • Realty One Group First, Magdalena Ko...
Leisure Village
![135 EASTBOURNE CT UNIT C, RIDGE, NY, 119..., Ridge, NY 11961]()
2 beds
|1 baths
|1,118 sq ft
|Condo
135 EASTBOURNE CT UNIT C, RIDGE, NY, 119...
Community: Leisure Village
MLS 854336 • Coldwell Banker American Homes, Joy ...
Plymouth Estates at Mount Sinai
![164 IRA RD, MOUNT SINAI, NY, 11766, Mount Sinai, NY 11766]()
2 beds
|2 baths
|1,820 sq ft
|Condo
164 IRA RD, MOUNT SINAI, NY, 11766
Community: Plymouth Estates at Mount Sinai
MLS 878455 • Aliano Real Estate, Nicholas A. Colo...
Plymouth Estates at Mount Sinai
![166 IRA RD, MOUNT SINAI, NY, 11766, Mount Sinai, NY 11766]()
2 beds
|2 baths
|1,820 sq ft
|Townhouse
166 IRA RD, MOUNT SINAI, NY, 11766
Community: Plymouth Estates at Mount Sinai
MLS 878423 • Aliano Real Estate, Nicholas A. Colo...
Leisure Village
![373 WOODBRIDGE DR B, RIDGE, NY, 11961, Ridge, NY 11961]()
2 beds
|1 baths
|1,171 sq ft
|Condo
373 WOODBRIDGE DR B, RIDGE, NY, 11961
Community: Leisure Village
MLS 845085 • Center 24 Realty Corp, Heidi S. Will...
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.
Founders Village
![2555 YOUNGS AVE 7D, SOUTHOLD, NY, 11971, Southold, NY 11971]()
2 beds
|2 baths
|1,100 sq ft
|Condo
2555 YOUNGS AVE 7D, SOUTHOLD, NY, 11971
Community: Founders Village
MLS 808158 • Signature Premier Properties, Timoth...
Leisure Village
![119 EXMORE CT A, RIDGE, NY, 11961, Ridge, NY 11961]()
MLS 872112 • Leisure Living Realty Inc, Paulina R...
Founders Village
![2555 YOUNGS AVE 11D, SOUTHOLD, NY, 11971, Southold, NY 11971]()
2 beds
|2 baths
|1,100 sq ft
|Condo
2555 YOUNGS AVE 11D, SOUTHOLD, NY, 11971
Community: Founders Village
MLS 828475 • Signature Premier Properties, Patric...
Leisure Village
![332 WOODBRIDGE DR UNIT C WOODBRIDGE DR, ..., Ridge, NY 11961]()
2 beds
|1 baths
|1,000 sq ft
|Condo
332 WOODBRIDGE DR UNIT C WOODBRIDGE DR, ...
Community: Leisure Village
MLS 861217 • Howard Hanna Coach, Linda Stowell
Frequently Asked Questions
In the Winchester Area, there are no large communities, no medium communities, and 2 small communities with less than 500 homes.
The smallest 55+ communities in the Winchester Area has 31 homes, the largest has 38 homes, and the average communities consists of 34 homes.
Yes, there is new 55+ home available in the Winchester Area. The most recent communities started in the Winchester Area include Oak Meadow Estates, Clockmaker's Hill. There is also 1 communities in the Winchester Area that offers new construction homes, including Oak Meadow Estates.
No, there are no gated 55+ communities in the Winchester Area.
On average, listings in 55+ communities in the Winchester Area stay on the market for around 663 days. The average price of homes for sale in these communities is approximately $389,900, though prices can range widely based on the size, location, and amenities of the communities. For example, homes in Oak Meadow Estates average around $389,900.
Want to learn more about 55+ communities in the Winchester Area?
- Insights and market stats
- Instant new home alerts
- Answers from local 55+ experts
Want to learn more about 55+ communities in Winchester Area?
234
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