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

159 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

Oronoque Village

$200ks - $400ks

Oronoque Village, Stratford, CT

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

3 rating (2 reviews)

Heritage Hills

$400ks - $900ks

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 | Built 1967 - 1982 | 1,000 homes

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

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

Questions? Call us: (860) 909-8066

Overlook

$600ks - $900ks

Overlook, Carmel, NY

New Construction | 55+ age-restricted | 300 homes

Fairview at Oxford Greens

$400ks - $600ks

Fairview at Oxford Greens, Oxford, CT

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

Rivington

$300ks - $900ks

Rivington, Danbury, CT

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

5 rating (1 reviews)

Newtown Woods

$300ks - $500ks

Newtown Woods, Newtown, CT

New and Resale | 55+ age-restricted | Built 2011 - present | 178 homes

Regency at Fishkill

$300ks - $400ks

Regency at Fishkill, Fishkill, NY

Resale Only | 55+ age-restricted | Built 2008 - 2020 | 164 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

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

Regency at Wappinger

$500ks

Regency at Wappinger, Wappingers Falls, NY

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

Evergreen

$400ks - $500ks

Evergreen, Cromwell, CT

New and Resale | 55+ age-restricted | Built 2005 - present | 52 homes

Liberty at Newtown

$300ks - $400ks

Liberty at Newtown, Newtown, CT

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

North Woods of Colchester

$300ks - $400ks

North Woods of Colchester, Colchester, CT

New and Resale | 55+ age-restricted | Built 2007 - present | 140 homes

Baldwin Station

$400ks

Baldwin Station, Milford, CT

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

Oak Meadow Estates

$200ks - $300ks

Oak Meadow Estates, Torrington, CT

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

The Powder Forest Homes

$500ks - $700ks

The Powder Forest Homes, Simsbury, CT

Resale Only | 55+ age-restricted | Built 2006 - 2016 | 182 homes

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

Questions? Call us: (860) 909-8066

The Gardens of Wilbraham

$200ks - $400ks

The Gardens of Wilbraham, Wilbraham, MA

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

Meadow Brook Estates

$300ks - $400ks

Meadow Brook Estates, Oxford, CT

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

South Pond Village

$300ks - $400ks

South Pond Village, Bloomfield, CT

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

Villas at Seminary Hill

$200ks - $300ks

Villas at Seminary Hill, Carmel, NY

New Construction | 55+ age-restricted | Built 2018 - present | 50 homes

O'Meara Farm

$400ks

O'Meara Farm, Farmington, CT

Resale Only | 55+ age-restricted | Built 1998 - 2005 | 104 homes

Regency at Woodbridge

$500ks - $700ks

Regency at Woodbridge, Woodbridge, CT

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

Bartlett Hill

$300ks - $400ks

Bartlett Hill, Portland, CT

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

The Village at Whispering...

$400ks

The Village at Whispering...Rotterdam, NY

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

Regency at Prospect

$300ks - $400ks

Regency at Prospect, Prospect, CT

Resale Only | 55+ age-restricted | Built 2006 - 2020 | 379 homes

Want to learn more about 55+ 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

Bramble Ridge

$300ks

Bramble Ridge, Suffield, CT

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

Autumn Fields

$200ks - $300ks

Autumn Fields, Enfield, CT

Resale Only | 55+ age-restricted | Built 2004 - 2006 | 56 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

Shaker Heights

$400ks - $500ks

Shaker Heights, Enfield, CT

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

Stoneleigh Woods at Carme...

$400ks

Stoneleigh Woods at Carme..., Carmel, NY

Resale Only | 55+ age-restricted | Built 2012 - 2017 | 68 homes

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

Questions? Call us: (860) 909-8066

Woodcrest at Jacobs Hill

$200ks - $300ks

Woodcrest at Jacobs Hill, Cortlandt, NY

Resale Only | 55+ age-restricted | Built 2005 - 2006 | 58 homes

Glassbury Court at Hunter...

$500ks - $700ks

Glassbury Court at Hunter..., Cortlandt, NY

Resale Only | 55+ age-restricted | Built 2007 - 2014 | 64 homes

1...2

New The Powder Forest Homes

37 BANTRY RD 37, SIMSBURY, CT, 06070, Simsbury, CT 06070

$899,000

3 beds

5 baths

2,724 sq ft

37 BANTRY RD 37, SIMSBURY, CT, 06070

Community: The Powder Forest Homes

New Jefferson Village

51 JEFFERSON OVAL F, YORKTOWN, NY, 10598, Yorktown, NY 10598

$448,500

2 beds

2 baths

1,100 sq ft

Condo

51 JEFFERSON OVAL F, YORKTOWN, NY, 10598

Community: Jefferson Village

New Regency at Wappinger

50 STRATFORD LN, WAPPINGER, NY, 12590, Wappinger, NY 12590

$689,000

2 beds

3 baths

1,823 sq ft

Condo

50 STRATFORD LN, WAPPINGER, NY, 12590

Community: Regency at Wappinger

New The Village at Oxford Greens

114 COUNTRY CLUB DR 114, OXFORD, CT, 064..., Oxford, CT 06478

$575,000

2 beds

2 baths

1,590 sq ft

114 COUNTRY CLUB DR 114, OXFORD, CT, 064...

Community: The Village at Oxford Greens

New Newtown Woods

1211 BROOKSIDE CT 1211, NEWTOWN, CT, 064..., Newtown, CT 06470

$485,000

2 beds

2 baths

1,483 sq ft

Condo

1211 BROOKSIDE CT 1211, NEWTOWN, CT, 064...

47 ASHTON CIR 47, SIMSBURY, CT, 06070

Community: The Powder Forest Homes

Heritage Village

1 HERITAGE VLG C, SOUTHBURY, CT, 06488, Southbury, CT 06488

$229,900

2 beds

2 baths

1,044 sq ft

Condo

1 HERITAGE VLG C, 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

214 WATERS EDGE DR 214, SOUTHINGTON, CT,..., Southington, CT 06489

$317,000

2 beds

3 baths

1,564 sq ft

Condo

214 WATERS EDGE DR 214, SOUTHINGTON, CT,...

Community: Spring Lake Village

Heritage Village

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

$358,000

2 beds

2 baths

1,398 sq ft

Condo

889 HERITAGE VLG B, SOUTHBURY, CT, 06488

Community: Heritage Village

North Woods of Colchester

24 CENTER CT 24, COLCHESTER, CT, 06415, Colchester, CT 06415

$515,000

2 beds

2 baths

1,357 sq ft

Condo

24 CENTER CT 24, COLCHESTER, CT, 06415

Community: North Woods of Colchester

Oronoque Village

402 MONTAUK LN B, STRATFORD, CT, 06614, Stratford, CT 06614

$515,000

2 beds

3 baths

1,118 sq ft

Condo

402 MONTAUK LN B, STRATFORD, CT, 06614

Community: Oronoque Village

Heritage Village

36 HERITAGE CIR B, SOUTHBURY, CT, 06488, Southbury, CT 06488

$525,000

3 beds

2 baths

1,716 sq ft

Condo

36 HERITAGE CIR B, SOUTHBURY, CT, 06488

Community: Heritage Village

South Pond Village

78 SILO WAY 78, BLOOMFIELD, CT, 06002, Bloomfield, CT 06002

$289,900

3 beds

3 baths

1,639 sq ft

Condo

78 SILO WAY 78, BLOOMFIELD, CT, 06002

Community: South Pond Village

The Powder Forest Homes

3 RONAN WAY 3, SIMSBURY, CT, 06070, Simsbury, CT 06070

$629,900

2 beds

3 baths

1,284 sq ft

Condo

3 RONAN WAY 3, SIMSBURY, CT, 06070

Community: The Powder Forest Homes

Heritage Hills

272 HERITAGE HLS C, SOMERS, NY, 10589, Somers, NY 10589

$569,900

2 beds

2 baths

1,500 sq ft

Condo

272 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

The Village at Oxford Greens

575 INVERNESS CT 575, OXFORD, CT, 06478, Oxford, CT 06478

$699,900

3 beds

3 baths

2,008 sq ft

575 INVERNESS CT 575, OXFORD, CT, 06478

Community: The Village at Oxford Greens

Oak Meadow Estates

65 OAK MEADOW LN 65, TORRINGTON, CT, 067..., Torrington, CT 06790

$485,000

2 beds

4 baths

2,164 sq ft

Condo

65 OAK MEADOW LN 65, TORRINGTON, CT, 067...

Community: Oak Meadow Estates

Jefferson Village

119 VILLAGE RD H, YORKTOWN, NY, 10598, Yorktown, NY 10598

$439,000

2 beds

2 baths

1,100 sq ft

Condo

119 VILLAGE RD H, YORKTOWN, NY, 10598

Community: Jefferson Village

Heritage Hills

725 HERITAGE HLS, SOMERS, NY, 10589, Somers, NY 10589

$774,900

2 beds

2 baths

1,526 sq ft

Condo

725 HERITAGE HLS, SOMERS, NY, 10589

Community: Heritage Hills

Heritage Village

4 HERITAGE VLG A, SOUTHBURY, CT, 06488, Southbury, CT 06488

$249,000

1 beds

1 baths

928 sq ft

Condo

4 HERITAGE VLG A, SOUTHBURY, CT, 06488

Community: Heritage Village

Jefferson Village

129 COLUMBIA CT D, YORKTOWN, NY, 10598, Yorktown, NY 10598

$469,999

2 beds

2 baths

1,100 sq ft

Condo

129 COLUMBIA CT D, YORKTOWN, NY, 10598

Community: Jefferson Village

Fairview at Oxford Greens

1077 AUGUSTA DR 1077, OXFORD, CT, 06478, Oxford, CT 06478

$684,900

3 beds

3 baths

2,256 sq ft

Condo

1077 AUGUSTA DR 1077, OXFORD, CT, 06478

Community: Fairview at Oxford Greens

The Village at Oxford Greens

$684,900

3 beds

3 baths

2,256 sq ft

Condo

1077 AUGUSTA DR 1077, OXFORD, CT, 06478

Community: The Village at Oxford Greens

Overlook

2079 SUMMIT LOOP 103, CARMEL, NY, 10512, Carmel, NY 10512

$899,000

2 beds

2 baths

1,948 sq ft

Condo

2079 SUMMIT LOOP 103, CARMEL, NY, 10512

10 REGENTS PL D, YORKTOWN, NY, 10598

Community: Jefferson Village

O'Meara Farm

1 MAGNOLIA CIR 1, FARMINGTON, CT, 06032, Farmington, CT 06032

$480,000

2 beds

2 baths

1,416 sq ft

Condo

1 MAGNOLIA CIR 1, FARMINGTON, CT, 06032

Community: O'Meara Farm

Heritage Village

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

$360,000

2 beds

2 baths

1,432 sq ft

Condo

640 HERITAGE VLG B, SOUTHBURY, CT, 06488

Community: Heritage Village

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

Questions? Call us: (860) 909-8066

Regency at Fishkill

145 REGENCY DR, FISHKILL, NY, 12524, Fishkill, NY 12524

$549,999

2 beds

2 baths

1,803 sq ft

Condo

145 REGENCY DR, FISHKILL, NY, 12524

Community: Regency at Fishkill

Oronoque Village

47 HURON LN A, STRATFORD, CT, 06614, Stratford, CT 06614

$409,000

2 beds

2 baths

1,360 sq ft

Condo

47 HURON LN A, STRATFORD, CT, 06614

Community: Oronoque Village

1 2 3…4

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.

Want more information about active adult communities around Winsted?

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159 homes

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

78 communities near Winsted

159 homes near Winsted

3 beds

5 baths

2,724 sq ft

2 beds

2 baths

1,100 sq ft

Condo

2 beds

3 baths

1,823 sq ft

Condo

2 beds

2 baths

1,590 sq ft

2 beds

2 baths

1,483 sq ft

Condo

2 beds

2 baths

1,398 sq ft

Condo

2 beds

3 baths

2,407 sq ft

Condo

2 beds

3 baths

1,806 sq ft

Condo

1 beds

1 baths

850 sq ft

Condo

2 beds

2 baths

1,483 sq ft

Condo

2 beds

3 baths

2,295 sq ft

Condo

2 beds

3 baths

1,843 sq ft

2 beds

2 baths

1,044 sq ft

Condo

2 beds

3 baths

1,564 sq ft

Condo

2 beds

2 baths

1,398 sq ft

Condo

2 beds

2 baths

1,357 sq ft

Condo

2 beds

3 baths

1,118 sq ft

Condo

3 beds

2 baths

1,716 sq ft

Condo

3 beds

3 baths

1,639 sq ft

Condo

2 beds

3 baths

1,284 sq ft

Condo