Call us at (860) 909-8066 to learn more about active adult communities in Winsted
Winsted, CT 55+ active adult communities & homes for sale - Page 4
78 communities near Winsted
134 homes near Winsted
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3.6 rating (7 reviews)
![Heritage Village]()
$200ks
- $500ks
Heritage Village, Southbury, CT
Resale Only
|
55+ age-restricted
|
Built 1967 - 2005
|
2,580 homes
3 rating (2 reviews)
![Heritage Hills]()
$400ks
- $1Ms
Heritage Hills, Somers, NY
Resale Only
|
Age-targeted
|
Built 1974 - 2006
|
2,600 homes
$200ks
- $400ks
Oronoque Village, Stratford, CT
Resale Only
|
55+ age-restricted
|
Built 1971 - 1977
|
929 homes
4 rating (1 reviews)
![Jefferson Village]()
$100ks
- $500ks
Jefferson Village, Yorktown Heights, NY
Resale Only
|
55+ age-restricted
|
Built 1967 - 1982
|
1,000 homes
Want to learn more about 55+ communities in Winsted?
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Questions? Call us:
(860) 909-8066
$100ks
- $200ks
Spring Lake Village, Southington, CT
Resale Only
|
55+ age-restricted
|
Built 1970 - 2004
|
640 homes
$300ks
- $900ks
Rivington, Danbury, CT
New and Resale
|
Age-targeted
|
Built 2006 - present
|
1,050 homes
$400ks
- $500ks
The Village at Oxford Gre..., Oxford, CT
New and Resale
|
55+ age-restricted
|
Built 2004 - present
|
835 homes
$300ks
- $800ks
The Retreat at Carmel, Carmel, NY
Resale Only
|
55+ age-restricted
|
Built 2008 - 2018
|
312 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)
![Newtown Woods]()
$300ks
- $500ks
Newtown Woods, Newtown, CT
New and Resale
|
55+ age-restricted
|
Built 2011 - present
|
178 homes
$300ks
- $400ks
South Pond Village, Bloomfield, CT
Resale Only
|
55+ age-restricted
|
Built 1999 - 2005
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151 homes
$400ks
- $600ks
Fairview at Oxford Greens, Oxford, CT
New and Resale
|
55+ age-restricted
|
Built 2019 - present
|
125 homes
$500ks
- $700ks
Glassbury Court at Cold S..., Cold Spring, NY
Resale Only
|
55+ age-restricted
|
Built 2009 - 2014
|
90 homes
Want to learn more about 55+ communities in Winsted?
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Questions? Call us:
(860) 909-8066
$400ks
The Village at Whispering...Rotterdam, NY
New Construction
|
55+ age-restricted
|
Built 2025 - present
|
85 homes
$500ks
- $700ks
Regency at Woodbridge, Woodbridge, CT
New Construction
|
55+ age-restricted
|
Built 2023 - present
|
70 homes
$200ks
- $400ks
The Gardens of Wilbraham, Wilbraham, MA
New and Resale
|
55+ age-restricted
|
Built 2005 - present
|
108 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.
$300ks
- $400ks
Liberty at Newtown, Newtown, CT
Resale Only
|
55+ age-restricted
|
Built 2003 - 2007
|
96 homes
$300ks
- $400ks
Bartlett Hill, Portland, CT
Resale Only
|
55+ age-restricted
|
Built 2005 - 2011
|
82 homes
5 rating (1 reviews)
![Paris Square]()
$600ks
- $900ks
Paris Square, Northvale, NJ
New and Resale
|
55+ age-restricted
|
Built 2000 - present
|
88 homes
$200ks
- $300ks
Oak Meadow Estates, Torrington, CT
New and Resale
|
55+ age-restricted
|
Built 2013 - present
|
31 homes
Want to learn more about 55+ communities in Winsted?
55places can help!
Questions? Call us:
(860) 909-8066
$300ks
- $500ks
Park Glen, New Milford, CT
Resale Only
|
55+ age-restricted
|
Built 2006 - 2015
|
17 homes
$300ks
- $400ks
Meadow Brook Estates, Oxford, CT
Resale Only
|
55+ age-restricted
|
Built 2003 - 2020
|
246 homes
$200ks
- $300ks
Villas at Seminary Hill, Carmel, NY
New Construction
|
55+ age-restricted
|
Built 2018 - present
|
50 homes
4.9 rating (14 reviews)
![Chatfield Farms]()
$400ks
- $700ks
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.
$300ks
- $400ks
Regency at Fishkill, Fishkill, NY
Resale Only
|
55+ age-restricted
|
Built 2008 - 2020
|
164 homes
$300ks
The Village at Hunt Glen, Granby, CT
Resale Only
|
55+ age-restricted
|
Built 2003 - 2006
|
69 homes
$600ks
- $700ks
Granite Woods, Middlebury, CT
New Construction
|
55+ age-restricted
|
Built 2020 - present
|
24 homes
$500ks
Regency at Wappinger, Wappingers Falls, NY
Resale Only
|
55+ age-restricted
|
Built 2014 - 2020
|
225 homes
$400ks
- $500ks
Evergreen, Cromwell, CT
New and Resale
|
55+ age-restricted
|
Built 2005 - present
|
52 homes
Want to learn more about 55+ communities in Winsted?
55places can help!
Questions? Call us:
(860) 909-8066
$300ks
- $400ks
Newington Ridge Preserve, Newington, CT
New Construction
|
55+ age-restricted
|
Built 2014 - present
|
16 homes
$200ks
- $300ks
Gloria Commons, Milford, CT
Resale Only
|
55+ age-restricted
|
Built 2007 - 2015
|
50 homes
$200ks
- $300ks
Hopmeadow Place, Simsbury, CT
Resale Only
|
55+ age-restricted
|
Built 2005 - 2005
|
66 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.
$300ks
- $400ks
Long Hill Village, Trumbull, CT
Resale Only
|
55+ age-restricted
|
Built 1997 - 1999
|
71 homes
$400ks
RiverBend Estates, Oxford, CT
New and Resale
|
55+ age-restricted
|
Built 2012 - present
|
25 homes
$300ks
- $400ks
Summer Wind Estates, North Haven, CT
New Construction
|
55+ age-restricted
|
Built 2015 - present
|
18 homes
$200ks
- $400ks
The Woods at Dunham Pond, New Fairfield, CT
Resale Only
|
55+ age-restricted
|
Built 2004 - 2015
|
33 homes
Want to learn more about 55+ communities in Winsted?
55places can help!
Questions? Call us:
(860) 909-8066
$500ks
Regency Meadows, Trumbull, CT
Resale Only
|
55+ age-restricted
|
Built 2003 - 2005
|
51 homes
Glassbury Court at Cold Spring
![43 YESTERDAY DR, COLD SPRING, NY, 10516, Cold Spring, NY 10516]()
2 beds
|3 baths
|2,620 sq ft
|Condo
43 YESTERDAY DR, COLD SPRING, NY, 10516
Community: Glassbury Court at Cold Spring
MLS 912195 • Coldwell Banker Realty, Audra Maccar...
Heritage Village
![977 HERITAGE VLG B, SOUTHBURY, CT, 06488, Southbury, CT 06488]()
3 beds
|2 baths
|1,716 sq ft
|Condo
977 HERITAGE VLG B, SOUTHBURY, CT, 06488
Community: Heritage Village
MLS 24099168 • William Pitt Sotheby's Int'l, Mary...
Heritage Village
![902 HERITAGE VLG A, SOUTHBURY, CT, 06488, Southbury, CT 06488]()
2 beds
|2 baths
|1,398 sq ft
|Condo
902 HERITAGE VLG A, SOUTHBURY, CT, 06488
Community: Heritage Village
MLS 24126334 • Joseph Bette REALTORS Inc, Justin ...
Heritage Village
![626 HERITAGE VLG, SOUTHBURY, CT, 06488, Southbury, CT 06488]()
2 beds
|2 baths
|1,432 sq ft
|Condo
626 HERITAGE VLG, SOUTHBURY, CT, 06488
Community: Heritage Village
MLS 24126430 • Coldwell Banker Realty, Kary Apano...
Heritage Village
![644 HERITAGE VLG A, SOUTHBURY, CT, 06488, Southbury, CT 06488]()
3 beds
|2 baths
|1,716 sq ft
|Condo
644 HERITAGE VLG A, SOUTHBURY, CT, 06488
Community: Heritage Village
MLS 24125882 • Berkshire Hathaway NE Prop., Miche...
Want to learn more about 55+ communities in Winsted?
55places can help!
Questions? Call us:
(860) 909-8066
Heritage Village
![825 HERITAGE VLG B, SOUTHBURY, CT, 06488, Southbury, CT 06488]()
2 beds
|2 baths
|1,365 sq ft
|Condo
825 HERITAGE VLG B, SOUTHBURY, CT, 06488
Community: Heritage Village
MLS 24124224 • Keller Williams Realty, Donna Doyl...
Heritage Village
![643 HERITAGE VLG A, SOUTHBURY, CT, 06488, Southbury, CT 06488]()
2 beds
|2 baths
|1,398 sq ft
|Condo
643 HERITAGE VLG A, SOUTHBURY, CT, 06488
Community: Heritage Village
MLS 24119411 • Drakeley Real Estate, Inc., Timoth...
Newtown Woods
![603 BROOKSIDE CT # 603, NEWTOWN, CT, 064..., Newtown, CT 06470]()
2 beds
|2 baths
|1,504 sq ft
|Condo
603 BROOKSIDE CT # 603, NEWTOWN, CT, 064...
Community: Newtown Woods
MLS 24120267 • Coldwell Banker Realty, Pete Gille...
Heritage Village
![132 HERITAGE VLG A, SOUTHBURY, CT, 06488, Southbury, CT 06488]()
2 beds
|2 baths
|1,432 sq ft
|Condo
132 HERITAGE VLG A, SOUTHBURY, CT, 06488
Community: Heritage Village
MLS 24118807 • William Raveis Real Estate, Ron Ne...
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 Village
![740 HERITAGE VLG B, SOUTHBURY, CT, 06488, Southbury, CT 06488]()
2 beds
|2 baths
|1,432 sq ft
|Condo
740 HERITAGE VLG B, SOUTHBURY, CT, 06488
Community: Heritage Village
MLS 24116195 • William Raveis Real Estate, Daniel...
Fairview at Oxford Greens
![1097 SAINT ANDREWS DR LOT 9, OXFORD, CT,..., Oxford, CT 06478]()
2 beds
|3 baths
|2,536 sq ft
|Condo
1097 SAINT ANDREWS DR LOT 9, OXFORD, CT,...
Community: Fairview at Oxford Greens
MLS 24110964 • EG Group Realty LLC, Shabnam Sadat
The Village at Oxford Greens
![1097 SAINT ANDREWS DR LOT 9, OXFORD, CT,..., Oxford, CT 06478]()
2 beds
|3 baths
|2,536 sq ft
|Condo
1097 SAINT ANDREWS DR LOT 9, OXFORD, CT,...
Community: The Village at Oxford Greens
MLS 24110964 • EG Group Realty LLC, Shabnam Sadat
Park Glen
![10 HARMONY TRL # 10, NEW MILFORD, CT, 06..., New Milford, CT 06776]()
2 beds
|3 baths
|4,023 sq ft
|Condo
10 HARMONY TRL # 10, NEW MILFORD, CT, 06...
Community: Park Glen
MLS 24109997 • Coldwell Banker Realty, Erin Porte...
Want to learn more about 55+ communities in Winsted?
55places can help!
Questions? Call us:
(860) 909-8066
The Village at Whispering Pines
![96 WHISPERING PINES WAY, ROTTERDAM, NY, ..., Rotterdam, NY 12306]()
2 beds
|2 baths
|1,500 sq ft
|House
96 WHISPERING PINES WAY, ROTTERDAM, NY, ...
Community: The Village at Whispering Pines
MLS 202520115 • TriStar Real Estate LLC, Anthony ...
Frequently Asked Questions
In Winsted, there is 1 small community with less than 500 homes.
The smallest 55+ community in Winsted has 38 homes, the largest has 38 homes, and the average community consists of 38 homes.
No, there are no gated 55+ communities in Winsted.
Want more information about active adult communities around Winsted?
Want to learn more about 55+ communities in Winsted?
134
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REIN updates its listings on a daily basis. Data last updated: Feb 28, 2026.
This application does not include information on all of the properties available for sale at this time.
