Call us at (860) 909-8066 to learn more about active adult communities in Winsted
Winsted, CT 55+ active adult communities & homes for sale
79 communities near Winsted
180 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
- $800ks
Heritage Hills, Somers, NY
Resale Only
|
Age-targeted
|
Built 1974 - 2006
|
2,600 homes
4 rating (1 reviews)
![Jefferson Village]()
$100ks
- $500ks
Jefferson Village, Yorktown Heights, NY
Resale Only
|
55+ age-restricted
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Built 1967 - 1982
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1,000 homes
5 rating (2 reviews)
![Oronoque Village]()
$200ks
- $400ks
Oronoque Village, Stratford, CT
Resale Only
|
55+ age-restricted
|
Built 1971 - 1977
|
929 homes
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(860) 909-8066
$400ks
- $500ks
The Village at Oxford Gre..., Oxford, CT
New and Resale
|
55+ age-restricted
|
Built 2004 - present
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835 homes
$400ks
- $600ks
Fairview at Oxford Greens, Oxford, CT
New and Resale
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55+ age-restricted
|
Built 2019 - present
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125 homes
$100ks
- $200ks
Spring Lake Village, Southington, CT
Resale Only
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55+ age-restricted
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Built 1970 - 2004
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640 homes
$300ks
- $400ks
Regency at Fishkill, Fishkill, NY
Resale Only
|
55+ age-restricted
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Built 2008 - 2020
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164 homes
$300ks
- $900ks
Rivington, Danbury, CT
New and Resale
|
Age-targeted
|
Built 2006 - present
|
1,050 homes
Download the Ultimate 55+ Homebuying Guide
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$200ks
- $400ks
The Gardens of Wilbraham, Wilbraham, MA
New and Resale
|
55+ age-restricted
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Built 2005 - present
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108 homes
5 rating (1 reviews)
![Newtown Woods]()
$300ks
- $500ks
Newtown Woods, Newtown, CT
New and Resale
|
55+ age-restricted
|
Built 2011 - present
|
178 homes
$500ks
- $700ks
Glassbury Court at Cold S..., Cold Spring, NY
Resale Only
|
55+ age-restricted
|
Built 2009 - 2014
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90 homes
$300ks
- $400ks
Liberty at Newtown, Newtown, CT
Resale Only
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55+ age-restricted
|
Built 2003 - 2007
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96 homes
$500ks
- $700ks
The Summit at Bethel, Bethel, CT
Resale Only
|
55+ age-restricted
|
Built 2010 - 2021
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235 homes
$400ks
- $600ks
Billingsgate, Simsbury, CT
Resale Only
|
55+ age-restricted
|
Built 2003 - 2006
|
37 homes
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(860) 909-8066
$500ks
- $700ks
Regency at Woodbridge, Woodbridge, CT
New Construction
|
55+ age-restricted
|
Built 2023 - present
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70 homes
$400ks
The Village at Whispering...Rotterdam, NY
New Construction
|
55+ age-restricted
|
Built 2025 - present
|
85 homes
$500ks
- $700ks
The Powder Forest Homes, Simsbury, CT
Resale Only
|
55+ age-restricted
|
Built 2006 - 2016
|
182 homes
Download the Ultimate 55+ Homebuying Guide
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$300ks
- $800ks
The Retreat at Carmel, Carmel, NY
Resale Only
|
55+ age-restricted
|
Built 2008 - 2018
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312 homes
$500ks
Regency Meadows, Trumbull, CT
Resale Only
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55+ age-restricted
|
Built 2003 - 2005
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51 homes
$500ks
Regency at Wappinger, Wappingers Falls, NY
Resale Only
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55+ age-restricted
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Built 2014 - 2020
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225 homes
$200ks
- $300ks
Woodcrest at Jacobs Hill, Cortlandt, NY
Resale Only
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55+ age-restricted
|
Built 2005 - 2006
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58 homes
$500ks
- $800ks
Fieldstone Village, Orange, CT
Resale Only
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55+ age-restricted
|
Built 2010 - 2018
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142 homes
$300ks
Pond Spring Village, Beacon Falls, CT
New and Resale
|
55+ age-restricted
|
Built 2005 - present
|
92 homes
Want to learn more about 55+ communities in Winsted?
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Questions? Call us:
(860) 909-8066
$300ks
- $400ks
Meadow Brook Estates, Oxford, CT
Resale Only
|
55+ age-restricted
|
Built 2003 - 2020
|
246 homes
$200ks
- $400ks
The Woods at Dunham Pond, New Fairfield, CT
Resale Only
|
55+ age-restricted
|
Built 2004 - 2015
|
33 homes
$300ks
- $400ks
Bidwell Village, Coventry, CT
New Construction
|
55+ age-restricted
|
Built 2020 - present
|
37 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
- $500ks
Cobblestone Court, Essex, CT
New and Resale
|
55+ age-restricted
|
Built 2017 - present
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8 homes
$300ks
- $400ks
South Pond Village, Bloomfield, CT
Resale Only
|
55+ age-restricted
|
Built 1999 - 2005
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151 homes
$300ks
- $400ks
Forest Mews, Avon, CT
Resale Only
|
55+ age-restricted
|
Built 2001 - 2004
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40 homes
$300ks
The Village at Hunt Glen, Granby, CT
Resale Only
|
55+ age-restricted
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Built 2003 - 2006
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69 homes
$400ks
O'Meara Farm, Farmington, CT
Resale Only
|
55+ age-restricted
|
Built 1998 - 2005
|
104 homes
$300ks
- $400ks
The Coach Homes at Ridgef..., Ridgefield, CT
New Construction
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55+ age-restricted
|
Built 2019 - present
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30 homes
$400ks
- $500ks
Evergreen, Cromwell, CT
New and Resale
|
55+ age-restricted
|
Built 2005 - present
|
52 homes
$500ks
- $600ks
Whitney Glen, Westport, CT
Resale Only
|
55+ age-restricted
|
Built 1982 - 1982
|
62 homes
Want to learn more about 55+ communities in Winsted?
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Questions? Call us:
(860) 909-8066
$400ks
- $500ks
Shaker Heights, Enfield, CT
New Construction
|
55+ age-restricted
|
Built 2018 - present
|
77 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.
New
Heritage Village
![419 HERITAGE VLG B, SOUTHBURY, CT, 06488, Southbury, CT 06488]()
2 beds
|2 baths
|1,032 sq ft
|Condo
419 HERITAGE VLG B, SOUTHBURY, CT, 06488
Community: Heritage Village
MLS 24196209 • Keller Williams Realty, Marvin Ben... • Keller Williams Realty
New
Jefferson Village
![39 SUSSEX DR B, YORKTOWN, NY, 10598, Yorktown, NY 10598]()
2 beds
|2 baths
|1,000 sq ft
|Condo
39 SUSSEX DR B, YORKTOWN, NY, 10598
Community: Jefferson Village
MLS 1028904 • Coldwell Banker Realty, Mary L. Cra... • Coldwell Banker Realty
Heritage Village
![345 HERITAGE VLG A, SOUTHBURY, CT, 06488, Southbury, CT 06488]()
3 beds
|2 baths
|1,716 sq ft
|Condo
345 HERITAGE VLG A, SOUTHBURY, CT, 06488
Community: Heritage Village
MLS 24196164 • Keller Williams Realty, Marvin Ben... • Keller Williams Realty
New
The Village at Oxford Greens
![171 COUNTRY CLUB DR 171, OXFORD, CT, 064..., Oxford, CT 06478]()
3 beds
|3 baths
|2,750 sq ft
|Condo
171 COUNTRY CLUB DR 171, OXFORD, CT, 064...
Community: The Village at Oxford Greens
MLS 24198161 • Exceptional Real Estate LLC, Teren... • Exceptional Real Estate LLC
New
Oronoque Village
![621 ONONDAGA LN B, STRATFORD, CT, 06614, Stratford, CT 06614]()
1 beds
|3 baths
|2,356 sq ft
|Condo
621 ONONDAGA LN B, STRATFORD, CT, 06614
Community: Oronoque Village
MLS 24197716 • Oronoque Real Estate, Monica Dalto... • Oronoque Real Estate
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(860) 909-8066
New
Heritage Hills
![88 HERITAGE HLS B, SOMERS, NY, 10589, Somers, NY 10589]()
2 beds
|3 baths
|1,585 sq ft
|Condo
88 HERITAGE HLS B, SOMERS, NY, 10589
Community: Heritage Hills
MLS 1036559 • Howard Hanna Rand Realty, Anna Hawl... • Howard Hanna Rand Realty
New
Jefferson Village
![196 LONG HILL DR B, YORKTOWN, NY, 10598, Yorktown, NY 10598]()
2 beds
|2 baths
|1,550 sq ft
|Condo
196 LONG HILL DR B, YORKTOWN, NY, 10598
Community: Jefferson Village
MLS 1032027 • Houlihan Lawrence Inc., Kathleen O'... • Houlihan Lawrence Inc.
New
Hopmeadow Place
![1 W ST 215, SIMSBURY, CT, 06070, Simsbury, CT 06070]()
MLS 24197881 • Berkshire Hathaway NE Prop., Matt ... • Berkshire Hathaway NE Prop.
New
The Gardens of Wilbraham
![23 CHERRY DR 23, WILBRAHAM, MA, 01095, Wilbraham, MA 01095]()
1 beds
|2 baths
|1,218 sq ft
|Condo
23 CHERRY DR 23, WILBRAHAM, MA, 01095
Community: The Gardens of Wilbraham
MLS 73561009 • Ayre Real Estate Co, Inc., The Ayr... • Ayre Real Estate Co, Inc.
New
The Summit at Bethel
![78 GREAT HILL DR 78, BETHEL, CT, 06801, Bethel, CT 06801]()
MLS 24189167 • William Raveis Real Estate, Jacque... • William Raveis Real Estate
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
Meadow Brook Estates
![169 MEADOW BROOK RD 169, OXFORD, CT, 064..., Oxford, CT 06478]()
2 beds
|3 baths
|1,821 sq ft
|Condo
169 MEADOW BROOK RD 169, OXFORD, CT, 064...
Community: Meadow Brook Estates
MLS 24187421 • William Raveis Real Estate, Pat Bl... • William Raveis Real Estate
New
Spring Lake Village
![116 TIMBER RDG, SOUTHINGTON, CT, 06489, Southington, CT 06489]()
2 beds
|2 baths
|1,128 sq ft
|Condo
116 TIMBER RDG, SOUTHINGTON, CT, 06489
Community: Spring Lake Village
MLS 24197425 • BHGRE Gaetano Marra Homes, Mary An... • BHGRE Gaetano Marra Homes
New
Jefferson Village
![34 WARWICK PL B, YORKTOWN, NY, 10598, Yorktown, NY 10598]()
2 beds
|2 baths
|1,000 sq ft
|Condo
34 WARWICK PL B, YORKTOWN, NY, 10598
Community: Jefferson Village
MLS 1035286 • Corcoran Legends Realty, Elvira Alo... • Corcoran Legends Realty
New
Heritage Hills
![537 HERITAGE HILLS DR F, SOMERS, NY, 105..., Somers, NY 10589]()
2 beds
|2 baths
|1,265 sq ft
|Condo
537 HERITAGE HILLS DR F, SOMERS, NY, 105...
Community: Heritage Hills
MLS 1033806 • Houlihan Lawrence Inc., Donna O'Con... • Houlihan Lawrence Inc.
New
Heritage Village
![170 HERITAGE VLG B, SOUTHBURY, CT, 06488, Southbury, CT 06488]()
2 beds
|2 baths
|1,432 sq ft
|Condo
170 HERITAGE VLG B, SOUTHBURY, CT, 06488
Community: Heritage Village
MLS 24197599 • Ascend Realty LLC, Michael Monteir... • Ascend Realty LLC
New
Heritage Hills
![159 HERITAGE HLS B, SOMERS, NY, 10589, Somers, NY 10589]()
2 beds
|2 baths
|1,500 sq ft
|Condo
159 HERITAGE HLS B, SOMERS, NY, 10589
Community: Heritage Hills
MLS 1025739 • William Raveis-New York LLC, Joann ... • William Raveis-New York LLC
Want to learn more about 55+ communities in Winsted?
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Questions? Call us:
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New
Oronoque Village
![511 OPA LN B, STRATFORD, CT, 06614, Stratford, CT 06614]()
2 beds
|2 baths
|1,620 sq ft
|Condo
511 OPA LN B, STRATFORD, CT, 06614
Community: Oronoque Village
MLS 24197217 • William Raveis Real Estate, Bernie... • William Raveis Real Estate
New
Jefferson Village
![184 LONG HILL DR A, YORKTOWN, NY, 10598, Yorktown, NY 10598]()
2 beds
|2 baths
|1,200 sq ft
|Condo
184 LONG HILL DR A, YORKTOWN, NY, 10598
Community: Jefferson Village
MLS 1032562 • Keller Williams Realty Partner, Mar... • Keller Williams Realty Partner
New
Heritage Village
![105 HERITAGE VLG B, SOUTHBURY, CT, 06488, Southbury, CT 06488]()
2 beds
|2 baths
|1,432 sq ft
|Condo
105 HERITAGE VLG B, SOUTHBURY, CT, 06488
Community: Heritage Village
MLS 24179726 • Drakeley Real Estate, Inc., Jeffre... • Drakeley Real Estate, Inc.
New
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 24196891 • William Raveis Real Estate, Ruth Z... • William Raveis Real Estate
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
Autumn Fields
![37 QUAIL HOLW 37, ENFIELD, CT, 06082, Enfield, CT 06082]()
2 beds
|3 baths
|1,679 sq ft
|Condo
37 QUAIL HOLW 37, ENFIELD, CT, 06082
Community: Autumn Fields
MLS 24196610 • Lamacchia Realty, Hayley Talbot • Lamacchia Realty
New
Jefferson Village
![20 HASTINGS CT A, YORKTOWN, NY, 10598, Yorktown, NY 10598]()
1 beds
|1 baths
|800 sq ft
|Condo
20 HASTINGS CT A, YORKTOWN, NY, 10598
Community: Jefferson Village
MLS 1035474 • Connect RE Corp., Bryant Mero • Connect RE Corp.
Rivington
![215 CENTER MEADOW LN 215, DANBURY, CT, 0..., Danbury, CT 06810]()
2 beds
|2 baths
|1,258 sq ft
|Condo
215 CENTER MEADOW LN 215, DANBURY, CT, 0...
Community: Rivington
MLS 24196346 • Coldwell Banker Realty, Antonio Za... • Coldwell Banker Realty
Heritage Village
![4 HERITAGE VLG A, SOUTHBURY, CT, 06488, Southbury, CT 06488]()
1 beds
|1 baths
|928 sq ft
|Condo
4 HERITAGE VLG A, SOUTHBURY, CT, 06488
Community: Heritage Village
MLS 24196977 • Berkshire Hathaway NE Prop., Jacqu... • Berkshire Hathaway NE Prop.
Overlook
![2040 SUMMIT LOOP 57, CARMEL, NY, 10512, Carmel, NY 10512]()
MLS 1034928 • Toll Brothers Real Estate Inc., Tho... • Toll Brothers Real Estate Inc.
Regency at Woodbridge
![27 HERITAGE LN, WOODBRIDGE, CT, 06525, Woodbridge, CT 06525]()
MLS 24196535 • Houlihan Lawrence WD, Laura Hart • Houlihan Lawrence WD
Heritage Hills
![813 HERITAGE HLS, SOMERS, NY, 10589, Somers, NY 10589]()
2 beds
|2 baths
|1,663 sq ft
|Condo
813 HERITAGE HLS, SOMERS, NY, 10589
Community: Heritage Hills
MLS 1034338 • Coldwell Banker Realty, Hope Ross M... • Coldwell Banker Realty
Want to learn more about 55+ communities in Winsted?
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(860) 909-8066
The Village at Oxford Greens
![1159 ST ANDREWS DR 80, OXFORD, CT, 06478, Oxford, CT 06478]()
2 beds
|3 baths
|1,955 sq ft
|Condo
1159 ST ANDREWS DR 80, OXFORD, CT, 06478
Community: The Village at Oxford Greens
MLS 24196547 • EG Group Realty LLC, Michael Helmu... • EG Group Realty LLC
Fairview at Oxford Greens
![1159 ST ANDREWS DR 80, OXFORD, CT, 06478, Oxford, CT 06478]()
2 beds
|3 baths
|1,955 sq ft
|Condo
1159 ST ANDREWS DR 80, OXFORD, CT, 06478
Community: Fairview at Oxford Greens
MLS 24196547 • EG Group Realty LLC, Michael Helmu... • EG Group Realty LLC
Regency at Fishkill
![732 REGENCY DR, FISHKILL, NY, 12524, Fishkill, NY 12524]()
1 beds
|2 baths
|1,499 sq ft
|Condo
732 REGENCY DR, FISHKILL, NY, 12524
Community: Regency at Fishkill
MLS 1032867 • Real Estate Connection Corp, Rhoda ... • Real Estate Connection Corp
Download the Ultimate 55+ Homebuying Guide
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Regency at Fishkill
![622 REGENCY DR, WAPPINGER, NY, 12524, Wappinger, NY 12524]()
1 beds
|2 baths
|1,450 sq ft
|Condo
622 REGENCY DR, WAPPINGER, NY, 12524
Community: Regency at Fishkill
MLS 1032907 • Solid Homes Realty Inc, Sam Beznos • Solid Homes Realty Inc
Fieldstone Village
![101 SUNRISE HILL CIR 101, ORANGE, CT, 06..., Orange, CT 06477]()
2 beds
|3 baths
|2,350 sq ft
|Condo
101 SUNRISE HILL CIR 101, ORANGE, CT, 06...
Community: Fieldstone Village
MLS 24193274 • Coldwell Banker Realty, Nick Mastr... • Coldwell Banker Realty
Sonoma Woods
![52 SONOMA LN 52, MIDDLETOWN, CT, 06457, Middletown, CT 06457]()
3 beds
|3 baths
|1,996 sq ft
|Condo
52 SONOMA LN 52, MIDDLETOWN, CT, 06457
Community: Sonoma Woods
MLS 24196378 • Berkshire Hathaway NE Prop., Mark ... • Berkshire Hathaway NE Prop.
The Retreat at Carmel
![8 ATKINS CT, CARMEL, NY, 10512, Carmel, NY 10512]()
2 beds
|3 baths
|2,148 sq ft
|Condo
8 ATKINS CT, CARMEL, NY, 10512
Community: The Retreat at Carmel
MLS 1021855 • RE/MAX Classic Realty, Pamela Carin... • RE/MAX Classic Realty
Spring Lake Village
![142 TIMBER RDG 142, SOUTHINGTON, CT, 064..., Southington, CT 06489]()
2 beds
|3 baths
|1,601 sq ft
|Condo
142 TIMBER RDG 142, SOUTHINGTON, CT, 064...
Community: Spring Lake Village
MLS 24195890 • Century 21 AllPoints Realty, Betty... • Century 21 AllPoints Realty
Heritage Village
![399 HERITAGE VLG B, SOUTHBURY, CT, 06488, Southbury, CT 06488]()
2 beds
|2 baths
|1,076 sq ft
|Condo
399 HERITAGE VLG B, SOUTHBURY, CT, 06488
Community: Heritage Village
MLS 24194613 • Berkshire Hathaway NE Prop., Bonni... • Berkshire Hathaway NE Prop.
Glassbury Court at Cold Spring
![5 MAGGIE MAY WAY, PHILIPSTOWN, NY, 10516, Philipstown, NY 10516]()
2 beds
|2 baths
|1,974 sq ft
|Condo
5 MAGGIE MAY WAY, PHILIPSTOWN, NY, 10516
Community: Glassbury Court at Cold Spring
MLS 1027839 • Houlihan Lawrence Inc., Arij Kurzum • Houlihan Lawrence Inc.
Chatfield Farms
![6 WOODLAND PATH 6, BEACON FALLS, CT, 064..., Beacon Falls, CT 06403]()
3 beds
|4 baths
|2,600 sq ft
|Condo
6 WOODLAND PATH 6, BEACON FALLS, CT, 064...
Community: Chatfield Farms
MLS 24194538 • William Raveis Real Estate, Nancy ... • William Raveis Real Estate
Want to learn more about 55+ communities in Winsted?
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Heritage Hills
![493 HERITAGE HLS A, SOMERS, NY, 10589, Somers, NY 10589]()
2 beds
|2 baths
|1,470 sq ft
|Condo
493 HERITAGE HLS A, SOMERS, NY, 10589
Community: Heritage Hills
MLS 1024568 • BHHS Hudson Valley Properties, Bonn... • BHHS Hudson Valley Properties
Heritage Village
![1003 HERITAGE VLG B, SOUTHBURY, CT, 0648..., Southbury, CT 06488]()
2 beds
|2 baths
|1,398 sq ft
|Condo
1003 HERITAGE VLG B, SOUTHBURY, CT, 0648...
Community: Heritage Village
MLS 24194571 • Coldwell Banker Realty, Maryanne B... • Coldwell Banker Realty
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.
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?
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© 2026 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: Aug 11, 2026.
This application does not include information on all of the properties available for sale at this time.
