Call us at (860) 909-8066 to learn more about active adult communities near Winsted
Winsted, CT 55+ active adult communities & homes for sale
76 communities near Winsted
166 homes near Winsted
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![Clockmaker's Hill]()
$100Ks
- $100Ks
Clockmaker's Hill, Winsted, CT
Resale Only
|
55+ age-restricted
|
Built 2005 - 2014
|
38 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
- $500Ks
Heritage Village, Southbury, CT
Resale Only
|
55+ age-restricted
|
Built 1967 - 2005
|
2,580 homes
No reviews yet
![Rivington]()
$400Ks
- $500Ks
Rivington, Danbury, CT
New and Resale
|
Age-targeted
|
Built 2006 - present
|
1,050 homes
4 rating (1 reviews)
![Jefferson Village]()
$300Ks
- $600Ks
Jefferson Village, Yorktown Heights, NY
Resale Only
|
55+ age-restricted
|
Built 1967 - 1982
|
1,000 homes
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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
![Spring Lake Village]()
$200Ks
- $200Ks
Spring Lake Village, Southington, CT
Resale Only
|
55+ age-restricted
|
Built 1970 - 2004
|
640 homes
No reviews yet
![Regency at Prospect]()
$300Ks
- $500Ks
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
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
![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
- $600Ks
Chatfield Farms, Beacon Falls, CT
New Construction
|
55+ age-restricted
|
Built 2014 - present
|
231 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
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(860) 909-8066
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
- $400Ks
Newtown Woods, Newtown, CT
New and Resale
|
55+ age-restricted
|
Built 2011 - present
|
178 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]()
$400Ks
- $500Ks
Regency at Fishkill, Fishkill, NY
Resale Only
|
55+ age-restricted
|
Built 2008 - 2020
|
164 homes
No reviews yet
![South Pond Village]()
$100Ks
- $200Ks
South Pond Village, Bloomfield, CT
Resale Only
|
55+ age-restricted
|
Built 1999 - 2005
|
151 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
![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]()
$500Ks
- $500Ks
North Woods of Colchester, Colchester, CT
New and Resale
|
55+ age-restricted
|
Built 2007 - present
|
140 homes
No reviews yet
![Fairview at Oxford Greens]()
$600Ks
- $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
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Questions? Call us:
(860) 909-8066
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
No reviews yet
![The Bridges at Oxford Gre...]()
$600Ks
- $600Ks
The Bridges at Oxford Gre..., Oxford, CT
New Construction
|
55+ age-restricted
|
Built 2025 - present
|
99 homes
No reviews yet
![Liberty at Newtown]()
$300Ks
- $400Ks
Liberty at Newtown, Newtown, CT
Resale Only
|
55+ age-restricted
|
Built 2003 - 2007
|
96 homes
No reviews yet
![Pond Spring Village]()
$300Ks
- $300Ks
Pond Spring Village, Beacon Falls, CT
New and Resale
|
55+ age-restricted
|
Built 2005 - present
|
92 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
![Founders Village]()
$500Ks
- $600Ks
Founders Village, Southold, NY
Resale Only
|
55+ age-restricted
|
Built 1981 - 1985
|
92 homes
No reviews yet
![Glassbury Court at Cold S...]()
$500Ks
- $700Ks
Glassbury Court at Cold S..., Cold Spring, NY
Resale Only
|
55+ age-restricted
|
Built 2009 - 2014
|
90 homes
5 rating (1 reviews)
![Paris Square]()
$400Ks
- $700Ks
Paris Square, Northvale, NJ
New and Resale
|
55+ age-restricted
|
Built 2000 - present
|
88 homes
No reviews yet
![Castle Heights of Cheshir...]()
$500Ks
- $600Ks
Castle Heights of Cheshir..., Cheshire, CT
Resale Only
|
55+ age-restricted
|
Built 2007 - 2022
|
88 homes
No reviews yet
![Bartlett Hill]()
$500Ks
- $500Ks
Bartlett Hill, Portland, CT
Resale Only
|
55+ age-restricted
|
Built 2005 - 2011
|
82 homes
Want to learn more about 55+ communities in Winsted?
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Questions? Call us:
(860) 909-8066
No reviews yet
![Baldwin Station]()
$400Ks
- $400Ks
Baldwin Station, Milford, CT
Resale Only
|
55+ age-restricted
|
Built 2001 - 2003
|
82 homes
5 rating (2 reviews)
![Benson Woods]()
$400Ks
- $600Ks
Benson Woods, Middlebury, CT
New and Resale
|
55+ age-restricted
|
Built 2004 - present
|
79 homes
No reviews yet
![Shaker Heights]()
$400Ks
- $500Ks
Shaker Heights, Enfield, CT
New Construction
|
55+ age-restricted
|
Built 2018 - present
|
77 homes
5 rating (3 reviews)
![Founders Ridge]()
$500Ks
- $600Ks
Founders Ridge, Middletown, CT
New Construction
|
55+ age-restricted
|
Built 2017 - present
|
75 homes
No reviews yet
![Long Hill Village]()
$300Ks
- $400Ks
Long Hill Village, Trumbull, CT
Resale Only
|
55+ age-restricted
|
Built 1997 - 1999
|
71 homes
Heritage Hills
![593 HERITAGE HLS B, SOMERS, NY, 10589, Somers, NY 10589]()
3 beds
|2 baths
|1,905 sq ft
|Condo
593 HERITAGE HLS B, SOMERS, NY, 10589
Community: Heritage Hills
MLS 921343 • Douglas Elliman Real Estate, Frankli...
Heritage Hills
![972 C HERITAGE HLS Y., SOMERS, NY, 10589, Somers, NY 10589]()
2 beds
|2 baths
|1,468 sq ft
|Condo
972 C HERITAGE HLS Y., SOMERS, NY, 10589
Community: Heritage Hills
MLS 886325 • Houlihan Lawrence Inc., Rita Carrozz...
Regency at Fishkill
![334 REGENCY DR, FISHKILL, NY, 12524, Fishkill, NY 12524]()
2 beds
|2 baths
|1,499 sq ft
|Condo
334 REGENCY DR, FISHKILL, NY, 12524
Community: Regency at Fishkill
MLS 910750 • Serhant LLC, Steven Wrobel Jr
Heritage Hills
![774 HERITAGE HLS B, SOMERS, NY, 10589, Somers, NY 10589]()
3 beds
|2 baths
|1,909 sq ft
|Condo
774 HERITAGE HLS B, SOMERS, NY, 10589
Community: Heritage Hills
MLS 919074 • Houlihan Lawrence Inc., Linda Crispi...
Jefferson Village
![141 FLINTLOCK WAY B, YORKTOWN HEIGHTS, N..., Yorktown Heights, NY 10598]()
2 beds
|2 baths
|1,555 sq ft
|Condo
141 FLINTLOCK WAY B, YORKTOWN HEIGHTS, N...
Community: Jefferson Village
MLS 918640 • Coldwell Banker Realty, Antonio Zacc...
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Jefferson Village
![34 WARWICK PL D, YORKTOWN HEIGHTS, NY, 1..., Yorktown Heights, NY 10598]()
2 beds
|2 baths
|970 sq ft
|House
34 WARWICK PL D, YORKTOWN HEIGHTS, NY, 1...
Community: Jefferson Village
MLS 875893 • Douglas Elliman Real Estate, Margare...
Regency at Fishkill
![145 REGENCY DR, FISHKILL, NY, 12524, Fishkill, NY 12524]()
2 beds
|2 baths
|1,803 sq ft
|Condo
145 REGENCY DR, FISHKILL, NY, 12524
Community: Regency at Fishkill
MLS 898170 • Realty Center Hudson Valley, Edwin D...
Heritage Hills
![356 HERITAGE HLS B, SOMERS, NY, 10589, Somers, NY 10589]()
3 beds
|2 baths
|1,793 sq ft
|Condo
356 HERITAGE HLS B, SOMERS, NY, 10589
Community: Heritage Hills
MLS 883084 • Coldwell Banker Realty, Valerie SanA...
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...
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...
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
![859 HERITAGE VLG B, SOUTHBURY, CT, 06488, Southbury, CT 06488]()
3 beds
|2 baths
|1,716 sq ft
|Condo
859 HERITAGE VLG B, SOUTHBURY, CT, 06488
Community: Heritage Village
MLS 24116487 • Litchfield County Real Estate, Cou...
Gloria Commons
![10 LUCIUS CT # 10, MILFORD, CT, 06461, Milford, CT 06461]()
2 beds
|3 baths
|2,061 sq ft
|Condo
10 LUCIUS CT # 10, MILFORD, CT, 06461
Community: Gloria Commons
MLS 24125515 • Preston Gray Real Estate, Katie Da...
Heritage Village
![313 HERITAGE VLG D, SOUTHBURY, CT, 06488, Southbury, CT 06488]()
2 beds
|2 baths
|1,044 sq ft
|Condo
313 HERITAGE VLG D, SOUTHBURY, CT, 06488
Community: Heritage Village
MLS 24117831 • The Washington Agency, Joanne Donn...
Oronoque Village
![736 QUINNIPIAC LN B, STRATFORD, CT, 0661..., Stratford, CT 06614]()
1 beds
|3 baths
|1,426 sq ft
|Condo
736 QUINNIPIAC LN B, STRATFORD, CT, 0661...
Community: Oronoque Village
MLS 24127108 • Coldwell Banker Realty, Larry Vecc...
Heritage Village
![920 HERITAGE VLG B, SOUTHBURY, CT, 06488, Southbury, CT 06488]()
2 beds
|2 baths
|1,432 sq ft
|Condo
920 HERITAGE VLG B, SOUTHBURY, CT, 06488
Community: Heritage Village
MLS 24127321 • Coldwell Banker Realty, Karen Cons...
Want to learn more about 55+ communities in Winsted?
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Heritage Village
![1034 HERITAGE VLG B, SOUTHBURY, CT, 0648..., Southbury, CT 06488]()
1 beds
|1 baths
|928 sq ft
|Condo
1034 HERITAGE VLG B, SOUTHBURY, CT, 0648...
Community: Heritage Village
MLS 24132420 • Emerald Glen Associates, Wendy Kud...
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...
Heritage Village
![26 HERITAGE CRST C, SOUTHBURY, CT, 06488, Southbury, CT 06488]()
2 beds
|2 baths
|1,217 sq ft
|Condo
26 HERITAGE CRST C, SOUTHBURY, CT, 06488
Community: Heritage Village
MLS 24123450 • Joseph Bette REALTORS Inc, Justin ...
Autumn Fields
![39 QUAIL HOLW # 39, ENFIELD, CT, 06082, Enfield, CT 06082]()
2 beds
|3 baths
|1,764 sq ft
|Condo
39 QUAIL HOLW # 39, ENFIELD, CT, 06082
Community: Autumn Fields
MLS 24123157 • Coldwell Banker Realty, Claudette ...
Heritage Village
![176 HERITAGE VLG B, SOUTHBURY, CT, 06488, Southbury, CT 06488]()
2 beds
|2 baths
|1,032 sq ft
|Condo
176 HERITAGE VLG B, SOUTHBURY, CT, 06488
Community: Heritage Village
MLS 24133427 • Keller Williams Realty Group, Lisa...
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
![123 HERITAGE VLG B, SOUTHBURY, CT, 06488, Southbury, CT 06488]()
2 beds
|2 baths
|1,398 sq ft
|Condo
123 HERITAGE VLG B, SOUTHBURY, CT, 06488
Community: Heritage Village
MLS 24117957 • Independent Realty Group, Tammi Li...
Spring Lake Village
![492 CARRIAGE DR # 492, SOUTHINGTON, CT, ..., Southington, CT 06489]()
2 beds
|2 baths
|1,313 sq ft
|Condo
492 CARRIAGE DR # 492, SOUTHINGTON, CT, ...
Community: Spring Lake Village
MLS 24127749 • Realty 3 CT, Diane Epps
Heritage Village
![919 HERITAGE VLG B, SOUTHBURY, CT, 06488, Southbury, CT 06488]()
2 beds
|2 baths
|1,432 sq ft
|Condo
919 HERITAGE VLG B, SOUTHBURY, CT, 06488
Community: Heritage Village
MLS 24123131 • Keller Williams Realty, Gabby Addi...
New
Park Glen
![1 BLOSSOM CT # 1, NEW MILFORD, CT, 06776, New Milford, CT 06776]()
2 beds
|2 baths
|1,880 sq ft
|Condo
1 BLOSSOM CT # 1, NEW MILFORD, CT, 06776
Community: Park Glen
MLS 24135079 • W. Raveis Lifestyles Realty, Austi...
Chatfield Farms
![18 FIELDSTONE LN # 18, BEACON FALLS, CT,..., Beacon Falls, CT 06403]()
2 beds
|3 baths
|2,719 sq ft
18 FIELDSTONE LN # 18, BEACON FALLS, CT,...
Community: Chatfield Farms
MLS 24120361 • Drakeley Real Estate, Inc., Joyce ...
Want to learn more about 55+ communities in Winsted?
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Questions? Call us:
(860) 909-8066
Spring Lake Village
![8 VILLAGE RD # 8, SOUTHINGTON, CT, 06489, Southington, CT 06489]()
2 beds
|2 baths
|1,314 sq ft
|Condo
8 VILLAGE RD # 8, SOUTHINGTON, CT, 06489
Community: Spring Lake Village
MLS 24129781 • Executive Real Estate Inc., Daniel...
Heritage Village
![93 HERITAGE VLG E, SOUTHBURY, CT, 06488, Southbury, CT 06488]()
2 beds
|2 baths
|1,365 sq ft
|Condo
93 HERITAGE VLG E, SOUTHBURY, CT, 06488
Community: Heritage Village
MLS 24121696 • Coldwell Banker Realty, Dawn Hough
Spring Lake Village
![18 COACH DR # 18, SOUTHINGTON, CT, 06489, Southington, CT 06489]()
2 beds
|2 baths
|1,178 sq ft
|Condo
18 COACH DR # 18, SOUTHINGTON, CT, 06489
Community: Spring Lake Village
MLS 24121584 • Realty 3 CT, Shelly Meister Zamudi...
New
Heritage Village
![862 HERITAGE VLG A, SOUTHBURY, CT, 06488, Southbury, CT 06488]()
3 beds
|2 baths
|1,716 sq ft
|Condo
862 HERITAGE VLG A, SOUTHBURY, CT, 06488
Community: Heritage Village
MLS 24135625 • Joseph Bette REALTORS Inc, Frank C...
Heritage Village
![916 HERITAGE VLG A, SOUTHBURY, CT, 06488, Southbury, CT 06488]()
2 beds
|2 baths
|1,432 sq ft
|Condo
916 HERITAGE VLG A, SOUTHBURY, CT, 06488
Community: Heritage Village
MLS 24133580 • Keller Williams Realty, Debi Orr
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
![53 HERITAGE VLG A, SOUTHBURY, CT, 06488, Southbury, CT 06488]()
2 beds
|2 baths
|1,432 sq ft
|Condo
53 HERITAGE VLG A, SOUTHBURY, CT, 06488
Community: Heritage Village
MLS 24083817 • Joseph Bette REALTORS Inc, Cynthia...
New
Oronoque Village
![50 CEDAR BARK LN A, STRATFORD, CT, 06614, Stratford, CT 06614]()
1 beds
|2 baths
|1,118 sq ft
|Condo
50 CEDAR BARK LN A, STRATFORD, CT, 06614
Community: Oronoque Village
MLS 24135024 • Century 21 AllPoints Realty, Karin...
Heritage Village
![114 HERITAGE VLG C, SOUTHBURY, CT, 06488, Southbury, CT 06488]()
2 beds
|2 baths
|1,032 sq ft
|Condo
114 HERITAGE VLG C, SOUTHBURY, CT, 06488
Community: Heritage Village
MLS 24128139 • Telesh Realty LLC, Igor Teleshevsk...
New
Heritage Village
![44 HERITAGE VLG F, SOUTHBURY, CT, 06488, Southbury, CT 06488]()
2 beds
|2 baths
|1,308 sq ft
|Condo
44 HERITAGE VLG F, SOUTHBURY, CT, 06488
Community: Heritage Village
MLS 24135482 • Joseph Bette REALTORS Inc, Deborah...
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...
Want to learn more about 55+ communities in Winsted?
55places can help!
Questions? Call us:
(860) 909-8066
Chatfield Farms
![81 FIELDSTONE LN # 81, BEACON FALLS, CT,..., Beacon Falls, CT 06403]()
2 beds
|2 baths
|1,988 sq ft
|Condo
81 FIELDSTONE LN # 81, BEACON FALLS, CT,...
Community: Chatfield Farms
MLS 24133207 • Century 21 AllPoints Realty, Kim L...
The Village at Oxford Greens
![578 PUTTING GREEN LN # 578, OXFORD, CT, ..., Oxford, CT 06478]()
2 beds
|3 baths
|2,008 sq ft
|Condo
578 PUTTING GREEN LN # 578, OXFORD, CT, ...
Community: The Village at Oxford Greens
MLS 24119430 • William Pitt Sotheby's Int'l, Tom ...
The Village at Oxford Greens
![106 COUNTRY CLUB DR # 106, OXFORD, CT, 0..., Oxford, CT 06478]()
2 beds
|3 baths
|1,590 sq ft
|Condo
106 COUNTRY CLUB DR # 106, OXFORD, CT, 0...
Community: The Village at Oxford Greens
MLS 24119727 • William Pitt Sotheby's Int'l, Tom ...
Oronoque Village
![488 COMMANCHE LN A, STRATFORD, CT, 06614, Stratford, CT 06614]()
2 beds
|3 baths
|1,438 sq ft
|Condo
488 COMMANCHE LN A, STRATFORD, CT, 06614
Community: Oronoque Village
MLS 24134368 • Higgins Group Real Estate, Carmen ...
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...
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?
166
homes
near Winsted
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REIN updates its listings on a daily basis. Data last updated: Oct 25, 2025.
This application does not include information on all of the properties available for sale at this time.
