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Winsted, CT 55+ active adult communities & homes for sale - Page 3

169 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
$500ks - $900ks
Heritage Hills, Somers, NY
Resale Only | Age-targeted | Built 1974 - 2006 | 2,600 homes
Oronoque Village
$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
Overlook
$600ks - $900ks
Overlook, Carmel, NY
New Construction | 55+ age-restricted | 300 homes
Want to learn more about 55+ communities in Winsted? 55places can help!
Questions? Call us: (860) 909-8066
The Village at Oxford Gre...
$400ks - $500ks
The Village at Oxford Gre..., Oxford, CT
New and Resale | 55+ age-restricted | Built 2004 - present | 835 homes
Rivington
$300ks - $900ks
Rivington, Danbury, CT
New and Resale | Age-targeted | Built 2006 - present | 1,050 homes
Fairview at Oxford Greens
$400ks - $600ks
Fairview at Oxford Greens, Oxford, CT
New and Resale | 55+ age-restricted | Built 2019 - present | 125 homes
5 rating (1 reviews) Newtown Woods
$300ks - $500ks
Newtown Woods, Newtown, CT
New and Resale | 55+ age-restricted | Built 2011 - present | 178 homes
Spring Lake Village
$100ks - $200ks
Spring Lake Village, Southington, CT
Resale Only | 55+ age-restricted | Built 1970 - 2004 | 640 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.
Liberty at Newtown
$300ks - $400ks
Liberty at Newtown, Newtown, CT
Resale Only | 55+ age-restricted | Built 2003 - 2007 | 96 homes
The Summit at Bethel
$500ks - $700ks
The Summit at Bethel, Bethel, CT
Resale Only | 55+ age-restricted | Built 2010 - 2021 | 235 homes
The Retreat at Carmel
$300ks - $800ks
The Retreat at Carmel, Carmel, NY
Resale Only | 55+ age-restricted | Built 2008 - 2018 | 312 homes
Meadow Brook Estates
$300ks - $400ks
Meadow Brook Estates, Oxford, CT
Resale Only | 55+ age-restricted | Built 2003 - 2020 | 246 homes
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
Regency at Fishkill
$300ks - $400ks
Regency at Fishkill, Fishkill, NY
Resale Only | 55+ age-restricted | Built 2008 - 2020 | 164 homes
Want to learn more about 55+ communities in Winsted? 55places can help!
Questions? Call us: (860) 909-8066
Regency at Wappinger
$500ks
Regency at Wappinger, Wappingers Falls, NY
Resale Only | 55+ age-restricted | Built 2014 - 2020 | 225 homes
North Woods of Colchester
$300ks - $400ks
North Woods of Colchester, Colchester, CT
New and Resale | 55+ age-restricted | Built 2007 - present | 140 homes
The Gardens of Wilbraham
$200ks - $400ks
The Gardens of Wilbraham, Wilbraham, MA
New and Resale | 55+ age-restricted | Built 2005 - present | 108 homes
The Village at Whispering...
$400ks
The Village at Whispering...Rotterdam, NY
New Construction | 55+ age-restricted | Built 2025 - present | 85 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.
Baldwin Station
$400ks
Baldwin Station, Milford, CT
Resale Only | 55+ age-restricted | Built 2001 - 2003 | 82 homes
The Powder Forest Homes
$500ks - $700ks
The Powder Forest Homes, Simsbury, CT
Resale Only | 55+ age-restricted | Built 2006 - 2016 | 182 homes
Regency at Prospect
$300ks - $400ks
Regency at Prospect, Prospect, CT
Resale Only | 55+ age-restricted | Built 2006 - 2020 | 379 homes
Gloria Commons
$200ks - $300ks
Gloria Commons, Milford, CT
Resale Only | 55+ age-restricted | Built 2007 - 2015 | 50 homes
Newbury Village
$400ks - $500ks
Newbury Village, Brookfield, CT
New and Resale | 55+ age-restricted | Built 2005 - present | 120 homes
Oak Meadow Estates
$200ks - $300ks
Oak Meadow Estates, Torrington, CT
New and Resale | 55+ age-restricted | Built 2013 - present | 31 homes
Bartlett Hill
$300ks - $400ks
Bartlett Hill, Portland, CT
Resale Only | 55+ age-restricted | Built 2005 - 2011 | 82 homes
Want to learn more about 55+ communities in Winsted? 55places can help!
Questions? Call us: (860) 909-8066
Villas at Seminary Hill
$200ks - $300ks
Villas at Seminary Hill, Carmel, NY
New Construction | 55+ age-restricted | Built 2018 - present | 50 homes
Pond Spring Village
$300ks
Pond Spring Village, Beacon Falls, CT
New and Resale | 55+ age-restricted | Built 2005 - present | 92 homes
Beckley Farms
$300ks - $400ks
Beckley Farms, Berlin, CT
New and Resale | 55+ age-restricted | Built 2010 - present | 170 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.
South Pond Village
$300ks - $400ks
South Pond Village, Bloomfield, CT
Resale Only | 55+ age-restricted | Built 1999 - 2005 | 151 homes
Forest Mews
$300ks - $400ks
Forest Mews, Avon, CT
Resale Only | 55+ age-restricted | Built 2001 - 2004 | 40 homes
5 rating (1 reviews) Paris Square
$400ks - $700ks
Paris Square, Northvale, NJ
New and Resale | 55+ age-restricted | Built 2000 - present | 88 homes
Evergreen
$400ks - $500ks
Evergreen, Cromwell, CT
New and Resale | 55+ age-restricted | Built 2005 - present | 52 homes
Regency at Woodbridge
$500ks - $700ks
Regency at Woodbridge, Woodbridge, CT
New Construction | 55+ age-restricted | Built 2023 - present | 70 homes
Bidwell Village
$300ks - $400ks
Bidwell Village, Coventry, CT
New Construction | 55+ age-restricted | Built 2020 - present | 37 homes
Cobblestone Court
$400ks - $500ks
Cobblestone Court, Essex, CT
New and Resale | 55+ age-restricted | Built 2017 - present | 8 homes
The Village at Hunt Glen
$300ks
The Village at Hunt Glen, Granby, CT
Resale Only | 55+ age-restricted | Built 2003 - 2006 | 69 homes
Want to learn more about 55+ communities in Winsted? 55places can help!
Questions? Call us: (860) 909-8066
The Coach Homes at Ridgef...
$300ks - $400ks
The Coach Homes at Ridgef..., Ridgefield, CT
New Construction | 55+ age-restricted | Built 2019 - present | 30 homes
Whitney Glen
$500ks - $600ks
Whitney Glen, Westport, CT
Resale Only | 55+ age-restricted | Built 1982 - 1982 | 62 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.
1...2
Heritage Village 78 HERITAGE VLG B, SOUTHBURY, CT, 06488, Southbury, CT 06488
$280,000

2 beds

|

2 baths

|

1,032 sq ft

|

Condo

78 HERITAGE VLG B, SOUTHBURY, CT, 06488
Community: Heritage Village
Rivington 424 CENTER MEADOW LN 424, DANBURY, CT, 0..., Danbury, CT 06810
$495,000

2 beds

|

2 baths

|

1,258 sq ft

|

Condo

424 CENTER MEADOW LN 424, DANBURY, CT, 0...
Community: Rivington
Bartlett Hill 9 PEAR ORCHARD RD 9, PORTLAND, CT, 06480, Portland, CT 06480
$479,900

2 beds

|

3 baths

|

1,404 sq ft

9 PEAR ORCHARD RD 9, PORTLAND, CT, 06480
Community: Bartlett Hill
Oronoque Village 639 ONONDAGA LN B, STRATFORD, CT, 06614, Stratford, CT 06614
$629,000

2 beds

|

3 baths

|

1,438 sq ft

|

Condo

639 ONONDAGA LN B, STRATFORD, CT, 06614
Community: Oronoque Village
Jefferson Village 68A INDEPENDENCE CT A, YORKTOWN, NY, 105..., Yorktown, NY 10598
$459,500

2 beds

|

2 baths

|

1,050 sq ft

|

Condo

68A INDEPENDENCE CT A, YORKTOWN, NY, 105...
Community: Jefferson Village
Want to learn more about 55+ communities in Winsted? 55places can help!
Questions? Call us: (860) 909-8066
Jefferson Village 26 DORSET CT A, YORKTOWN, NY, 10598, Yorktown, NY 10598
$230,000
|

1 baths

|

550 sq ft

|

Condo

26 DORSET CT A, YORKTOWN, NY, 10598
Community: Jefferson Village
Heritage Hills 392 HERITAGE HLS A, SOMERS, NY, 10589, Somers, NY 10589
$979,000

3 beds

|

2 baths

|

1,793 sq ft

|

Condo

392 HERITAGE HLS A, SOMERS, NY, 10589
Community: Heritage Hills
Heritage Village 41 E MEADOW RD, SOUTHBURY, CT, 06488, Southbury, CT 06488
$399,900

2 beds

|

3 baths

|

1,479 sq ft

|

Condo

41 E MEADOW RD, SOUTHBURY, CT, 06488
Community: Heritage Village
Paris Square 5201 RIO VISTA LN, NORTHVALE, NJ, 07647, Northvale, NJ 07647
$735,000

2 beds

|

2 baths

|

Condo

5201 RIO VISTA LN, NORTHVALE, NJ, 07647
Community: Paris Square
Overlook 3004 EASTVIEW DR 105, CARMEL, NY, 10512, Carmel, NY 10512
$722,000

2 beds

|

3 baths

|

2,040 sq ft

|

Condo

3004 EASTVIEW DR 105, CARMEL, NY, 10512
Community: Overlook
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.
Overlook 2031 SUMMIT LOOP 89, CARMEL, NY, 10512, Carmel, NY 10512
$883,000

2 beds

|

2 baths

|

1,948 sq ft

|

Condo

2031 SUMMIT LOOP 89, CARMEL, NY, 10512
Community: Overlook
Heritage Hills 769 HERITAGE HLS C, SOMERS, NY, 10589, Somers, NY 10589
$690,000

1 beds

|

2 baths

|

1,296 sq ft

|

Condo

769 HERITAGE HLS C, SOMERS, NY, 10589
Community: Heritage Hills
Heritage Village 665 HERITAGE VLG A, SOUTHBURY, CT, 06488, Southbury, CT 06488
$509,000

3 beds

|

2 baths

|

1,716 sq ft

|

Condo

665 HERITAGE VLG A, SOUTHBURY, CT, 06488
Community: Heritage Village
Newtown Woods 433 BROOKSIDE CT 433, NEWTOWN, CT, 06470, Newtown, CT 06470
$499,900

2 beds

|

2 baths

|

1,504 sq ft

|

Condo

433 BROOKSIDE CT 433, NEWTOWN, CT, 06470
Community: Newtown Woods
Oronoque Village 261 AGAWAM DR A, STRATFORD, CT, 06614, Stratford, CT 06614
$600,000

2 beds

|

3 baths

|

1,620 sq ft

|

Condo

261 AGAWAM DR A, STRATFORD, CT, 06614
Community: Oronoque Village
The Village at Oxford Greens 1125 ST ANDREWS DR 47, OXFORD, CT, 06478, Oxford, CT 06478
$689,900

2 beds

|

3 baths

|

2,454 sq ft

|

Condo

1125 ST ANDREWS DR 47, OXFORD, CT, 06478
Want to learn more about 55+ communities in Winsted? 55places can help!
Questions? Call us: (860) 909-8066
Fairview at Oxford Greens 1125 ST ANDREWS DR 47, OXFORD, CT, 06478, Oxford, CT 06478
$689,900

2 beds

|

3 baths

|

2,454 sq ft

|

Condo

1125 ST ANDREWS DR 47, OXFORD, CT, 06478
The Village at Oxford Greens 1093 ST ANDREWS DR 7, OXFORD, CT, 06478, Oxford, CT 06478
$689,900

2 beds

|

3 baths

|

2,454 sq ft

|

Condo

1093 ST ANDREWS DR 7, OXFORD, CT, 06478
Fairview at Oxford Greens 1093 ST ANDREWS DR 7, OXFORD, CT, 06478, Oxford, CT 06478
$689,900

2 beds

|

3 baths

|

2,454 sq ft

|

Condo

1093 ST ANDREWS DR 7, OXFORD, CT, 06478
The Village at Oxford Greens 1091 ST ANDREWS DR 6, OXFORD, CT, 06478, Oxford, CT 06478
$739,900

2 beds

|

3 baths

|

2,536 sq ft

|

Condo

1091 ST ANDREWS DR 6, OXFORD, CT, 06478
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.
Fairview at Oxford Greens 1091 ST ANDREWS DR 6, OXFORD, CT, 06478, Oxford, CT 06478
$739,900

2 beds

|

3 baths

|

2,536 sq ft

|

Condo

1091 ST ANDREWS DR 6, OXFORD, CT, 06478
Heritage Village 103 HERITAGE VLG D, SOUTHBURY, CT, 06488, Southbury, CT 06488
$289,900

2 beds

|

2 baths

|

1,044 sq ft

|

Condo

103 HERITAGE VLG D, SOUTHBURY, CT, 06488
Community: Heritage Village
Oronoque Village 546 N TRL B, STRATFORD, CT, 06614, Stratford, CT 06614
$679,000

2 beds

|

3 baths

|

1,434 sq ft

|

Condo

546 N TRL B, STRATFORD, CT, 06614
Community: Oronoque Village
Heritage Hills 228 HERITAGE HLS A, SOMERS, NY, 10589, Somers, NY 10589
$689,900

3 beds

|

3 baths

|

1,700 sq ft

|

Condo

228 HERITAGE HLS A, SOMERS, NY, 10589
Community: Heritage Hills
Oronoque Village 383 SEQUOIA LN A, STRATFORD, CT, 06614, Stratford, CT 06614
$635,000

1 beds

|

2 baths

|

1,360 sq ft

|

Condo

383 SEQUOIA LN A, STRATFORD, CT, 06614
Community: Oronoque Village
Regency at Wappinger 27 DUTCH CT, WAPPINGER, NY, 12590, Wappinger, NY 12590
$795,000

2 beds

|

4 baths

|

3,362 sq ft

|

Condo

27 DUTCH CT, WAPPINGER, NY, 12590
Heritage Village 191 HERITAGE VLG A, SOUTHBURY, CT, 06488, Southbury, CT 06488
$599,900

3 beds

|

2 baths

|

1,716 sq ft

|

Condo

191 HERITAGE VLG A, SOUTHBURY, CT, 06488
Community: Heritage Village
Want to learn more about 55+ communities in Winsted? 55places can help!
Questions? Call us: (860) 909-8066
Spring Lake Village 41 COACH DR 41, SOUTHINGTON, CT, 06489, Southington, CT 06489
$249,900

2 beds

|

2 baths

|

1,232 sq ft

|

Condo

41 COACH DR 41, SOUTHINGTON, CT, 06489
Community: Spring Lake Village
Heritage Village 865 HERITAGE VLG B, SOUTHBURY, CT, 06488, Southbury, CT 06488
$349,900

2 beds

|

2 baths

|

1,398 sq ft

|

Condo

865 HERITAGE VLG B, SOUTHBURY, CT, 06488
Community: Heritage Village
Overlook 2066 SUMMIT LOOP 68, CARMEL, NY, 10512, Carmel, NY 10512
$879,000

2 beds

|

3 baths

|

2,214 sq ft

|

Condo

2066 SUMMIT LOOP 68, CARMEL, NY, 10512
Community: Overlook
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 1041 HERITAGE VLG A, SOUTHBURY, CT, 0648..., Southbury, CT 06488
$279,900

2 beds

|

2 baths

|

1,000 sq ft

|

Condo

1041 HERITAGE VLG A, SOUTHBURY, CT, 0648...
Community: Heritage Village
Jefferson Village 41 JEFFERSON OVAL G, YORKTOWN, NY, 10598, Yorktown, NY 10598
$469,000

2 beds

|

2 baths

|

1,100 sq ft

|

Condo

41 JEFFERSON OVAL G, YORKTOWN, NY, 10598
Community: Jefferson Village
Jefferson Village 113 VILLAGE RD B, YORKTOWN, NY, 10598, Yorktown, NY 10598
$469,999

2 beds

|

2 baths

|

1,200 sq ft

|

Condo

113 VILLAGE RD B, YORKTOWN, NY, 10598
Community: Jefferson Village
Spring Lake Village 6 LAKEVIEW DR 6, SOUTHINGTON, CT, 06489, Southington, CT 06489
$315,000

3 beds

|

3 baths

|

1,471 sq ft

|

Condo

6 LAKEVIEW DR 6, SOUTHINGTON, CT, 06489
Community: Spring Lake Village
Oronoque Village 488 COMMANCHE LN A, STRATFORD, CT, 06614, Stratford, CT 06614
$599,000

1 beds

|

3 baths

|

2,199 sq ft

|

Condo

488 COMMANCHE LN A, STRATFORD, CT, 06614
Community: Oronoque Village
Heritage Village 170 HERITAGE VLG B, SOUTHBURY, CT, 06488, Southbury, CT 06488
$349,900

2 beds

|

2 baths

|

1,432 sq ft

|

Condo

170 HERITAGE VLG B, SOUTHBURY, CT, 06488
Community: Heritage Village
Glassbury Court at Cold Spring 15 REVOLUTION RD, PHILIPSTOWN, NY, 10516, Philipstown, NY 10516
$556,904

2 beds

|

3 baths

|

1,785 sq ft

|

Condo

15 REVOLUTION RD, PHILIPSTOWN, NY, 10516
Regency at Fishkill 734 REGENCY DR, FISHKILL, NY, 12524, Fishkill, NY 12524
$569,900

2 beds

|

2 baths

|

1,499 sq ft

|

Condo

734 REGENCY DR, FISHKILL, NY, 12524
Community: Regency at Fishkill
Want to learn more about 55+ communities in Winsted? 55places can help!
Questions? Call us: (860) 909-8066
Heritage Hills 40 HERITAGE HLS A, SOMERS, NY, 10589, Somers, NY 10589
$615,000

2 beds

|

2 baths

|

1,139 sq ft

|

Condo

40 HERITAGE HLS A, SOMERS, NY, 10589
Community: Heritage Hills
Heritage Village 575 HERITAGE VLG A, SOUTHBURY, CT, 06488, Southbury, CT 06488
$399,000

3 beds

|

2 baths

|

1,716 sq ft

|

Condo

575 HERITAGE VLG A, SOUTHBURY, CT, 06488
Community: Heritage Village
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.
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