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

78 communities near Winsted

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3.6 rating (7 reviews)

Heritage Village

$100Ks - $500Ks

Heritage Village, Southbury, CT

Resale Only | 55+ age-restricted | Built 1967 - 2005 | 2,580 homes

3 rating (2 reviews)

Heritage Hills

$300Ks - $900Ks

Heritage Hills, Somers, NY

Resale Only | Age-targeted | Built 1974 - 2006 | 2,600 homes

Oronoque Village

$200Ks - $600Ks

Oronoque Village, Stratford, CT

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

4 rating (1 reviews)

Jefferson Village

$200Ks - $500Ks

Jefferson Village, Yorktown Heights, NY

Resale Only | 55+ age-restricted | Built 1967 - 1982 | 1,000 homes

The Village at Oxford Gre...

$600Ks - $700Ks

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

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Rivington

$400Ks - $800Ks

Rivington, Danbury, CT

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

The Retreat at Carmel

$400Ks - $700Ks

The Retreat at Carmel, Carmel, NY

Resale Only | 55+ age-restricted | Built 2008 - 2018 | 312 homes

Regency at Woodbridge

$600Ks - $700Ks

Regency at Woodbridge, Woodbridge, CT

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

4.9 rating (14 reviews)

Chatfield Farms

$500Ks - $700Ks

Chatfield Farms, Beacon Falls, CT

New Construction | 55+ age-restricted | Built 2014 - present | 231 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.

Fairview at Oxford Greens

$600Ks - $700Ks

Fairview at Oxford Greens, Oxford, CT

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

5 rating (1 reviews)

Newtown Woods

$400Ks - $500Ks

Newtown Woods, Newtown, CT

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

The Village at Whispering...

$400Ks

The Village at Whispering...Rotterdam, NY

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

Spring Lake Village

$200Ks - $300Ks

Spring Lake Village, Southington, CT

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

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Questions? Call us: (860) 909-8066

South Pond Village

$200Ks - $400Ks

South Pond Village, Bloomfield, CT

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

The Gardens of Wilbraham

$500Ks

The Gardens of Wilbraham, Wilbraham, MA

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

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Questions? Call us: (860) 909-8066

Glassbury Court at Hunter...

$500Ks - $700Ks

Glassbury Court at Hunter..., Cortlandt, NY

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

Meadow Brook Estates

$500Ks

Meadow Brook Estates, Oxford, CT

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

Baldwin Station

$400Ks

Baldwin Station, Milford, CT

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

Granite Woods

$600Ks - $700Ks

Granite Woods, Middlebury, CT

New Construction | 55+ age-restricted | Built 2020 - present | 24 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

The Residences at Butterf...

$500Ks - $600Ks

The Residences at Butterf..., Cold Spring, NY

Resale Only | 55+ age-restricted | Built 2018 - 2023 | 49 homes

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Questions? Call us: (860) 909-8066

Villas at Seminary Hill

$400Ks

Villas at Seminary Hill, Carmel, NY

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

Regency at Wappinger

$600Ks - $700Ks

Regency at Wappinger, Wappingers Falls, NY

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

5 rating (1 reviews)

Paris Square

$400Ks - $700Ks

Paris Square, Northvale, NJ

New and Resale | 55+ age-restricted | Built 2000 - present | 88 homes

Oak Meadow Estates

$400Ks

Oak Meadow Estates, Torrington, CT

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

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Liberty at Newtown

$300Ks - $400Ks

Liberty at Newtown, Newtown, CT

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

Evergreen

$500Ks

Evergreen, Cromwell, CT

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

Bartlett Hill

$500Ks

Bartlett Hill, Portland, CT

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

Sonoma Woods

$300Ks

Sonoma Woods, Middletown, CT

Resale Only | 55+ age-restricted | Built 2005 - 2015 | 68 homes

Beckley Farms

$300Ks - $400Ks

Beckley Farms, Berlin, CT

New and Resale | 55+ age-restricted | Built 2010 - present | 170 homes

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Questions? Call us: (860) 909-8066

Castle Heights of Cheshir...

$500Ks - $600Ks

Castle Heights of Cheshir..., Cheshire, CT

Resale Only | 55+ age-restricted | Built 2007 - 2022 | 88 homes

North Woods of Colchester

$500Ks

North Woods of Colchester, Colchester, CT

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

Chimney Hill

$500Ks - $700Ks

Chimney Hill, Farmington, CT

Resale Only | 55+ age-restricted | Built 2006 - 2013 | 44 homes

Newington Ridge Preserve

$300Ks - $400Ks

Newington Ridge Preserve, Newington, CT

New Construction | 55+ age-restricted | Built 2014 - present | 16 homes

The Powder Forest Homes

$600Ks - $700Ks

The Powder Forest Homes, Simsbury, CT

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

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Questions? Call us: (860) 909-8066

5 rating (3 reviews)

Founders Ridge

$500Ks - $600Ks

Founders Ridge, Middletown, CT

New Construction | 55+ age-restricted | Built 2017 - present | 75 homes

Bartlett Hollow

$200Ks - $400Ks

Bartlett Hollow, Middletown, CT

New Construction | 55+ age-restricted | Built 2015 - present | 25 homes

Autumn Estates

$500Ks - $600Ks

Autumn Estates, Farmington, CT

Resale Only | 55+ age-restricted | Built 2011 - 2017 | 30 homes

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Questions? Call us: (860) 909-8066

The Atrium of Portland

<$100k

The Atrium of Portland, Portland, CT

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

Billingsgate

$400Ks - $600Ks

Billingsgate, Simsbury, CT

Resale Only | 55+ age-restricted | Built 2003 - 2006 | 37 homes

1...2

New Oak Meadow Estates

65 OAK MEADOW LN # 65, HARWINTON, CT, 06..., Harwinton, CT 06791

$495,000

2 beds

4 baths

2,164 sq ft

Condo

65 OAK MEADOW LN # 65, HARWINTON, CT, 06...

Community: Oak Meadow Estates

New South Pond Village

81 SILO WAY 81, BLOOMFIELD, CT, 06002, Bloomfield, CT 06002

$259,999

2 beds

2 baths

1,204 sq ft

Condo

81 SILO WAY 81, BLOOMFIELD, CT, 06002

Community: South Pond Village

New Heritage Hills

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

$599,000

1 beds

2 baths

1,296 sq ft

Condo

680 HERITAGE HLS C, SOMERS, NY, 10589

Community: Heritage Hills

New Villas at Seminary Hill

7102 PANKIN DR, CARMEL, NY, 10512, Carmel, NY 10512

$439,999

2 beds

2 baths

1,144 sq ft

Condo

7102 PANKIN DR, CARMEL, NY, 10512

Community: Villas at Seminary Hill

New Heritage Hills

243 HERITAGE HLS B, SOMERS, NY, 10589, Somers, NY 10589

$749,000

3 beds

2 baths

1,689 sq ft

Condo

243 HERITAGE HLS B, SOMERS, NY, 10589

Community: Heritage Hills

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

Questions? Call us: (860) 909-8066

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

Questions? Call us: (860) 909-8066

New Oronoque Village

133 BANNOCK LN, STRATFORD, CT, 06614, Stratford, CT 06614

$635,000

2 beds

3 baths

2,038 sq ft

Condo

133 BANNOCK LN, STRATFORD, CT, 06614

Community: Oronoque Village

New Heritage Village

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

$299,900

2 beds

2 baths

1,144 sq ft

Condo

914 HERITAGE VLG B, SOUTHBURY, CT, 06488

Community: Heritage Village

New Chatfield Farms

8 WOODLAND PATH # 8, BEACON FALLS, CT, 0..., Beacon Falls, CT 06403

$724,900

3 beds

4 baths

2,610 sq ft

Condo

8 WOODLAND PATH # 8, BEACON FALLS, CT, 0...

Community: Chatfield Farms

New Chatfield Farms

8 WOODLAND PATH 8, BEACON FALLS, CT, 064..., Beacon Falls, CT 06403

$724,900

3 beds

4 baths

2,610 sq ft

8 WOODLAND PATH 8, BEACON FALLS, CT, 064...

Community: Chatfield Farms

New Heritage Village

419 HERITAGE VLG E, SOUTHBURY, CT, 06488, Southbury, CT 06488

$500,000

3 beds

2 baths

1,716 sq ft

Condo

419 HERITAGE VLG E, SOUTHBURY, CT, 06488

Community: Heritage Village

Meadow Brook Estates

215 MEADOW BROOK RD # 215, OXFORD, CT, 0..., Oxford, CT 06478

$589,000

3 beds

3 baths

2,207 sq ft

Condo

215 MEADOW BROOK RD # 215, OXFORD, CT, 0...

Community: Meadow Brook Estates

The Residences at Butterfield

19 BUTTERFIELD RD UNIT 102B 102B, COLD S..., Cold Spring, NY 10516

$649,000

2 beds

2 baths

1,322 sq ft

Condo

19 BUTTERFIELD RD UNIT 102B 102B, COLD S...

Community: The Residences at Butterfield

Long Hill Village

71 CIDER MILL LN, TRUMBULL, CT, 06611, Trumbull, CT 06611

$539,900

1 beds

3 baths

1,370 sq ft

Condo

71 CIDER MILL LN, TRUMBULL, CT, 06611

Community: Long Hill Village

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

Questions? Call us: (860) 909-8066

Heritage Village

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

$295,000

2 beds

2 baths

1,432 sq ft

Condo

915 HERITAGE VLG A, SOUTHBURY, CT, 06488

Community: Heritage Village

Heritage Village

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

$325,000

2 beds

2 baths

1,432 sq ft

Condo

745 HERITAGE VLG B, SOUTHBURY, CT, 06488

Community: Heritage Village

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

Questions? Call us: (860) 909-8066

Oronoque Village

445 NORTH TRL A, STRATFORD, CT, 06614, Stratford, CT 06614

$644,900

1 beds

3 baths

1,620 sq ft

Condo

445 NORTH TRL A, STRATFORD, CT, 06614

Community: Oronoque Village

Jefferson Village

50 JEFFERSON OVAL A, YORKTOWN HEIGHTS, N..., Yorktown Heights, NY 10598

$475,000

2 beds

2 baths

910 sq ft

Condo

50 JEFFERSON OVAL A, YORKTOWN HEIGHTS, N...

Community: Jefferson Village

Rivington

1 WILDERSWOOD WAY # 1, DANBURY, CT, 0681..., Danbury, CT 06810

$899,900

3 beds

4 baths

2,596 sq ft

Condo

1 WILDERSWOOD WAY # 1, DANBURY, CT, 0681...

Community: Rivington

Heritage Village

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

$249,000

2 beds

2 baths

1,071 sq ft

Condo

968 HERITAGE VLG A, SOUTHBURY, CT, 06488

Community: Heritage Village

Chatfield Farms

9 LAKEVIEW RISE # 9, BEACON FALLS, CT, 0..., Beacon Falls, CT 06403

$515,000

2 beds

3 baths

1,700 sq ft

Condo

9 LAKEVIEW RISE # 9, BEACON FALLS, CT, 0...

Community: Chatfield Farms

Jefferson Village

53 JEFFERSON OVAL B, YORKTOWN HEIGHTS, N..., Yorktown Heights, NY 10598

$439,900

2 beds

2 baths

1,100 sq ft

Condo

53 JEFFERSON OVAL B, YORKTOWN HEIGHTS, N...

Community: Jefferson Village

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

Questions? Call us: (860) 909-8066

Sonoma Woods

60 SONOMA LN 60, MIDDLETOWN, CT, 06457, Middletown, CT 06457

$549,900

2 beds

3 baths

2,054 sq ft

Condo

60 SONOMA LN 60, MIDDLETOWN, CT, 06457

Community: Sonoma Woods

Heritage Hills

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

$500,000

2 beds

3 baths

1,550 sq ft

Condo

339 HERITAGE HLS A, SOMERS, NY, 10589

Community: Heritage Hills

South Pond Village

162 THISTLE POND DR 162, BLOOMFIELD, CT,..., Bloomfield, CT 06002

$395,000

2 beds

2 baths

1,341 sq ft

Condo

162 THISTLE POND DR 162, BLOOMFIELD, CT,...

Community: South Pond Village

Heritage Hills

882 HERITAGE HLS D, SOMERS, NY, 10589, Somers, NY 10589

$750,000

2 beds

3 baths

1,666 sq ft

Condo

882 HERITAGE HLS D, SOMERS, NY, 10589

Community: Heritage Hills

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

Questions? Call us: (860) 909-8066

The Retreat at Carmel

18 WHEELER CT, CARMEL, NY, 10512, Carmel, NY 10512

$749,900

2 beds

3 baths

2,035 sq ft

Condo

18 WHEELER CT, CARMEL, NY, 10512

Community: The Retreat at Carmel

The Village at Oxford Greens

117 COUNTRY CLUB DR 117, OXFORD, CT, 064..., Oxford, CT 06478

$649,900

3 beds

3 baths

2,666 sq ft

117 COUNTRY CLUB DR 117, OXFORD, CT, 064...

Community: The Village at Oxford Greens

Heritage Hills

578 HERITAGE HLS D, SOMERS, NY, 10589, Somers, NY 10589

$450,000

1 beds

2 baths

967 sq ft

Condo

578 HERITAGE HLS D, SOMERS, NY, 10589

Community: Heritage Hills

The Village at Oxford Greens

301 FAIRWAY DR 301, OXFORD, CT, 06478, Oxford, CT 06478

$619,000

2 beds

2 baths

2,080 sq ft

Condo

301 FAIRWAY DR 301, OXFORD, CT, 06478

Community: The Village at Oxford Greens

Granite Woods

35 NUTMEG RD D1, MIDDLEBURY, CT, 06762, Middlebury, CT 06762

$229,000

1 beds

1 baths

889 sq ft

Condo

35 NUTMEG RD D1, MIDDLEBURY, CT, 06762

Community: Granite Woods

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Regency at Wappinger

61 FARMINGTON RD, WAPPINGER, NY, 12590, Wappinger, NY 12590

$775,000

2 beds

2 baths

1,738 sq ft

House

61 FARMINGTON RD, WAPPINGER, NY, 12590

Community: Regency at Wappinger

Oronoque Village

635 NORTH TRL B, STRATFORD, CT, 06614, Stratford, CT 06614

$420,000

1 beds

3 baths

1,454 sq ft

Condo

635 NORTH TRL B, STRATFORD, CT, 06614

Community: Oronoque Village

Heritage Hills

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

$634,900

2 beds

2 baths

1,296 sq ft

Condo

656 HERITAGE HLS C, SOMERS, NY, 10589

Community: Heritage Hills

Heritage Village

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

$195,000

2 beds

2 baths

1,032 sq ft

Condo

73 HERITAGE VLG B, SOUTHBURY, CT, 06488

Community: Heritage Village

The Village at Oxford Greens

607 CHAMPIONSHIP DR # 607, OXFORD, CT, 0..., Oxford, CT 06478

$650,000

3 beds

3 baths

2,731 sq ft

Condo

607 CHAMPIONSHIP DR # 607, OXFORD, CT, 0...

Community: The Village at Oxford Greens

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

Questions? Call us: (860) 909-8066

Paris Square

5309 RIO VISTA LN, NORTHVALE, NJ, 07647, Northvale, NJ 07647

$479,000

1 beds

1 baths

Condo

5309 RIO VISTA LN, NORTHVALE, NJ, 07647

Community: Paris Square

Heritage Village

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

$299,900

2 beds

2 baths

1,365 sq ft

Condo

198 HERITAGE VLG A, SOUTHBURY, CT, 06488

Community: Heritage Village

The Summit at Bethel

12 BRIAR RIDGE DR # 12, BETHEL, CT, 0680..., Bethel, CT 06801

$619,900

2 beds

3 baths

2,023 sq ft

Condo

12 BRIAR RIDGE DR # 12, BETHEL, CT, 0680...

Community: The Summit at Bethel

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

Questions? Call us: (860) 909-8066

Oronoque Village

13 ALGONQUIN LN C, STRATFORD, CT, 06614, Stratford, CT 06614

$399,000

1 beds

2 baths

1,330 sq ft

Condo

13 ALGONQUIN LN C, STRATFORD, CT, 06614

Community: Oronoque Village

Heritage Hills

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

$645,000

3 beds

2 baths

1,689 sq ft

Condo

140 HERITAGE HLS A, SOMERS, NY, 10589

Community: Heritage Hills

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

138 homes near Winsted

2 beds

4 baths

2,164 sq ft

Condo

2 beds

2 baths

1,204 sq ft

Condo

1 beds

2 baths

1,296 sq ft

Condo

2 beds

2 baths

1,144 sq ft

Condo

3 beds

2 baths

1,689 sq ft

Condo

2 beds

3 baths

2,038 sq ft

Condo

2 beds

2 baths

1,144 sq ft

Condo

3 beds

4 baths

2,610 sq ft

Condo

3 beds

4 baths

2,610 sq ft

3 beds

2 baths

1,716 sq ft

Condo

3 beds

3 baths

2,207 sq ft

Condo

2 beds

2 baths

1,322 sq ft

Condo

1 beds

3 baths

1,370 sq ft

Condo

2 beds

2 baths

1,432 sq ft

Condo

2 beds

2 baths

1,432 sq ft

Condo

1 beds

3 baths

1,620 sq ft

Condo

2 beds

2 baths

910 sq ft

Condo

3 beds

4 baths

2,596 sq ft

Condo

2 beds

2 baths

1,071 sq ft

Condo

2 beds

3 baths