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

78 communities 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

Oronoque Village

$200ks - $400ks

Oronoque Village, Stratford, CT

Resale Only | 55+ age-restricted | Built 1971 - 1977 | 929 homes

Overlook

$600ks - $900ks

Overlook, Carmel, NY

New Construction | 55+ age-restricted | 300 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? 55places can help!

Questions? Call us: (860) 909-8066

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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

Fairview at Oxford Greens

$400ks - $600ks

Fairview at Oxford Greens, Oxford, CT

New and Resale | 55+ age-restricted | Built 2019 - present | 125 homes

Spring Lake Village

$100ks - $200ks

Spring Lake Village, Southington, CT

Resale Only | 55+ age-restricted | Built 1970 - 2004 | 640 homes

The Retreat at Carmel

$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

Read the Ultimate 55+ Rental Guide Thinking about renting in a 55+ active adult community? Our free guide has all the must-know info and practical tips to help you navigate 55+ renting and find your ideal next home in a 55+ community.

Rivington

$300ks - $900ks

Rivington, Danbury, CT

New and Resale | Age-targeted | Built 2006 - present | 1,050 homes

Bartlett Hill

$300ks - $400ks

Bartlett Hill, Portland, CT

Resale Only | 55+ age-restricted | Built 2005 - 2011 | 82 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

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

The Village at Whispering...

$400ks

The Village at Whispering...Rotterdam, NY

New Construction | 55+ age-restricted | Built 2025 - present | 85 homes

Want to learn more about 55+ rental 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

Oak Meadow Estates

$200ks - $300ks

Oak Meadow Estates, Torrington, CT

New and Resale | 55+ age-restricted | Built 2013 - present | 31 homes

Meadow Brook Estates

$300ks - $400ks

Meadow Brook Estates, Oxford, CT

Resale Only | 55+ age-restricted | Built 2003 - 2020 | 246 homes

Liberty at Newtown

$300ks - $400ks

Liberty at Newtown, Newtown, CT

Resale Only | 55+ age-restricted | Built 2003 - 2007 | 96 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

The Gardens of Wilbraham

$200ks - $400ks

The Gardens of Wilbraham, Wilbraham, MA

New and Resale | 55+ age-restricted | Built 2005 - present | 108 homes

Want to learn more about 55+ communities in Winsted? 55places can help!

Questions? Call us: (860) 909-8066

Regency at Woodbridge

$500ks - $700ks

Regency at Woodbridge, Woodbridge, CT

New Construction | 55+ age-restricted | Built 2023 - present | 70 homes

Regency at Wappinger

$500ks

Regency at Wappinger, Wappingers Falls, NY

Resale Only | 55+ age-restricted | Built 2014 - 2020 | 225 homes

South Pond Village

$300ks - $400ks

South Pond Village, Bloomfield, CT

Resale Only | 55+ age-restricted | Built 1999 - 2005 | 151 homes

Baldwin Station

$400ks

Baldwin Station, Milford, CT

Resale Only | 55+ age-restricted | Built 2001 - 2003 | 82 homes

Want to learn more about 55+ rental communities in Winsted? 55places can help!

Questions? Call us: (860) 909-8066

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

Park Glen

$300ks - $500ks

Park Glen, New Milford, CT

Resale Only | 55+ age-restricted | Built 2006 - 2015 | 17 homes

RiverBend Estates

$400ks

RiverBend Estates, Oxford, CT

New and Resale | 55+ age-restricted | Built 2012 - present | 25 homes

Summer Wind Estates

$300ks - $400ks

Summer Wind Estates, North Haven, CT

New Construction | 55+ age-restricted | Built 2015 - present | 18 homes

Want to learn more about 55+ communities in Winsted? 55places can help!

Questions? Call us: (860) 909-8066

The Woods at Dunham Pond

$200ks - $400ks

The Woods at Dunham Pond, New Fairfield, CT

Resale Only | 55+ age-restricted | Built 2004 - 2015 | 33 homes

Regency Meadows

$500ks

Regency Meadows, Trumbull, CT

Resale Only | 55+ age-restricted | Built 2003 - 2005 | 51 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

Forest Mews

$300ks - $400ks

Forest Mews, Avon, CT

Resale Only | 55+ age-restricted | Built 2001 - 2004 | 40 homes

Want to learn more about 55+ rental communities in Winsted? 55places can help!

Questions? Call us: (860) 909-8066

The Village at Hunt Glen

$300ks

The Village at Hunt Glen, Granby, CT

Resale Only | 55+ age-restricted | Built 2003 - 2006 | 69 homes

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

Want to learn more about 55+ communities in Winsted? 55places can help!

Questions? Call us: (860) 909-8066

Shaker Heights

$400ks - $500ks

Shaker Heights, Enfield, CT

New Construction | 55+ age-restricted | Built 2018 - present | 77 homes

Bramble Ridge

$300ks

Bramble Ridge, Suffield, CT

Resale Only | 55+ age-restricted | Built 2005 - 2015 | 47 homes

1...2

New Oronoque Village

252 AGAWAM DR A, STRATFORD, CT, 06614, Stratford, CT 06614

$639,000

2 beds

3 baths

2,823 sq ft

Condo

252 AGAWAM DR A, STRATFORD, CT, 06614

424 CENTER MEADOW LN 424, DANBURY, CT, 0...

Community: Rivington

New 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

Want to learn more about 55+ communities in Winsted? 55places can help!

26 DORSET CT A, YORKTOWN, NY, 10598

Community: Jefferson Village

New Heritage Hills

392 HERITAGE HLS A, SOMERS, NY, 10589, Somers, NY 10589

$979,000

2031 SUMMIT LOOP 89, CARMEL, NY, 10512, Carmel, NY 10512

$789,000

2 beds

2 baths

1,948 sq ft

Condo

2031 SUMMIT LOOP 89, CARMEL, NY, 10512

Community: Overlook

Regency at Fishkill

323 REGENCY DR 323, FISHKILL, NY, 12524, Fishkill, NY 12524

$485,000

1 beds

2 baths

1,450 sq ft

House

323 REGENCY DR 323, FISHKILL, NY, 12524

Community: Regency at Fishkill

Want to learn more about 55+ rental communities in Winsted? 55places can help!

Questions? Call us: (860) 909-8066

Meadow Brook Estates

312 SPRUCE HILL DR 312, OXFORD, CT, 0647..., Oxford, CT 06478

$529,900

2 beds

3 baths

1,564 sq ft

Condo

312 SPRUCE HILL DR 312, OXFORD, CT, 0647...

Community: Meadow Brook Estates

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

$524,900

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

Community: The Village at Oxford Greens

Want to learn more about 55+ communities in Winsted? 55places can help!

Questions? Call us: (860) 909-8066

Fairview at Oxford Greens

$689,900

2 beds

3 baths

2,454 sq ft

Condo

1125 ST ANDREWS DR 47, OXFORD, CT, 06478

Community: Fairview at Oxford Greens

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

Community: Fairview at Oxford Greens

The Village at Oxford Greens

$689,900

2 beds

3 baths

2,454 sq ft

Condo

1093 ST ANDREWS DR 7, OXFORD, CT, 06478

Community: The Village at Oxford Greens

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

179 HERITAGE HLS C, SOMERS, NY, 10589

Community: Heritage Hills

Want to learn more about 55+ communities in Winsted? 55places can help!

Questions? Call us: (860) 909-8066

Heritage Hills

831 HERITAGE HLS, SOMERS, NY, 10589, Somers, NY 10589

$900,000

2 beds

2 baths

1,663 sq ft

Condo

831 HERITAGE HLS, SOMERS, NY, 10589

Community: Heritage Hills

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

Oronoque Village

87 CREEK LN A, STRATFORD, CT, 06614, Stratford, CT 06614

$419,900

1 beds

2 baths

1,454 sq ft

Condo

87 CREEK LN A, STRATFORD, CT, 06614

Community: Oronoque Village

Heritage Hills

228 HERITAGE HLS A, SOMERS, NY, 10589, Somers, NY 10589

$699,900

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

Want to learn more about 55+ rental communities in Winsted? 55places can help!

Questions? Call us: (860) 909-8066

Heritage Village

919 HERITAGE VLG B, SOUTHBURY, CT, 06488, Southbury, CT 06488

$424,900

2 beds

2 baths

1,432 sq ft

Condo

919 HERITAGE VLG B, SOUTHBURY, CT, 06488

Community: Heritage Village

Regency at Wappinger

27 DUTCH CT, WAPPINGER, NY, 12590, Wappinger, NY 12590

$815,000

2 beds

4 baths

3,362 sq ft

Condo

27 DUTCH CT, WAPPINGER, NY, 12590

Community: Regency at Wappinger

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

Autumn Fields

11 PARTRIDGE RUN 11, ENFIELD, CT, 06082, Enfield, CT 06082

$399,900

2 beds

2 baths

1,296 sq ft

Condo

11 PARTRIDGE RUN 11, ENFIELD, CT, 06082

Community: Autumn Fields

Oronoque Village

483 COMMANCHE LN B, STRATFORD, CT, 06614, Stratford, CT 06614

$400,000

1 beds

2 baths

1,454 sq ft

Condo

483 COMMANCHE LN B, STRATFORD, CT, 06614

Community: Oronoque Village

Frequently Asked Questions

What size 55+ communities are there in Winsted?

In Winsted, there is 1 small community with less than 500 homes.

How many homes are there in the smallest, largest, and average 55+ communities in Winsted?

The smallest 55+ community in Winsted has 38 homes, the largest has 38 homes, and the average community consists of 38 homes.

Are there gated 55+ communities in Winsted?

No, there are no gated 55+ communities in Winsted.

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78 communities

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

78 communities near Winsted

145 homes near Winsted

2 beds

3 baths

2,823 sq ft

Condo

2 beds

2 baths

1,470 sq ft

Condo

2 beds

2 baths

1,032 sq ft

Condo

2 beds

2 baths

1,258 sq ft

Condo

2 beds

3 baths

1,404 sq ft

2 beds

3 baths

1,550 sq ft

Condo

2 beds

3 baths

1,438 sq ft

Condo

2 beds

2 baths

1,050 sq ft

Condo

1 baths

550 sq ft

Condo

3 beds

2 baths

1,793 sq ft

Condo

2 beds

3 baths

1,479 sq ft

Condo

2 beds

2 baths

Condo

2 beds

3 baths

2,040 sq ft

Condo

2 beds

2 baths

1,948 sq ft

Condo

1 beds

2 baths

1,450 sq ft

House

2 beds

3 baths

1,564 sq ft

Condo

1 beds

2 baths

1,296 sq ft

Condo

3 beds

2 baths

1,716 sq ft

Condo

2 beds

2 baths

1,504 sq ft

Condo

2 beds

3 baths

1,620 sq ft

Condo