Winsted, CT 55+ active adult communities & homes for sale - Page 2

79 communities near Winsted

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Founders Village

$400ks - $500ks

Founders Village, Southold, NY

Resale Only | 55+ age-restricted | Built 1981 - 1985 | 92 homes

3.5 rating (2 reviews)

Harvest Pointe

$800ks - $3Ms

Harvest Pointe, Cutchogue, NY

New Construction | 55+ age-restricted | Built 2017 - present | 124 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

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

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

Questions? Call us: (860) 909-8066

Eden Park

$500ks - $600ks

Eden Park, Clarkstown, NY

Resale Only | 55+ age-restricted | Built 2011 - 2011 | 34 homes

The Residences at Butterf...

$500ks - $600ks

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

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

Villas at Seminary Hill

$200ks - $300ks

Villas at Seminary Hill, Carmel, NY

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

Regency at Woodbridge

$500ks - $700ks

Regency at Woodbridge, Woodbridge, CT

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

The Bridges at Oxford Gre...

$600ks

The Bridges at Oxford Gre..., Oxford, CT

New Construction | 55+ age-restricted | Built 2025 - present | 99 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.

Rivington Landing

$500ks

Rivington Landing, Danbury, CT

New Construction | Age-targeted | Built 2025 - 2026 | 25 homes

5 rating (1 reviews)

Paris Square

$500ks - $700ks

Paris Square, Northvale, NJ

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

5 rating (2 reviews)

Benson Woods

$400ks - $600ks

Benson Woods, Middlebury, CT

New and Resale | 55+ age-restricted | Built 2004 - present | 79 homes

Granite Woods

$600ks - $700ks

Granite Woods, Middlebury, CT

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

Fieldstone Village

$500ks - $800ks

Fieldstone Village, Orange, CT

Resale Only | 55+ age-restricted | Built 2010 - 2018 | 142 homes

Meadow Brook Estates

$300ks - $400ks

Meadow Brook Estates, Oxford, CT

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

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

Questions? Call us: (860) 909-8066

4.9 rating (14 reviews)

Chatfield Farms

$400ks - $700ks

Chatfield Farms, Beacon Falls, CT

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

RiverWalk

$500ks - $600ks

RiverWalk, Branford, CT

New and Resale | 55+ age-restricted | Built 2007 - present | 60 homes

Baldwin Station

$400ks

Baldwin Station, Milford, CT

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

77 Sunset Lane

$400ks - $700ks

77 Sunset Lane, Ridgefield, CT

Resale Only | 55+ age-restricted | Built 2016 - 2018 | 54 homes

Boulder Brook

$200ks

Boulder Brook, Prospect, CT

Resale Only | 55+ age-restricted | Built 2004 - 2006 | 35 homes

Gloria Commons

$200ks - $300ks

Gloria Commons, Milford, CT

Resale Only | 55+ age-restricted | Built 2007 - 2015 | 50 homes

Long Hill Village

$300ks - $400ks

Long Hill Village, Trumbull, CT

Resale Only | 55+ age-restricted | Built 1997 - 1999 | 71 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

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

Cobblestone Court

$400ks - $500ks

Cobblestone Court, Essex, CT

New and Resale | 55+ age-restricted | Built 2017 - present | 8 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

Clockmaker's Hill

$100ks

Clockmaker's Hill, Winsted, CT

Resale Only | 55+ age-restricted | Built 2005 - 2014 | 38 homes

The Village at Buckingham

$300ks - $400ks

The Village at Buckingham, Avon, CT

Resale Only | 55+ age-restricted | Built 2002 - 2006 | 56 homes

Bartlett Hill

$300ks - $400ks

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

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

$300ks - $400ks

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

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

Questions? Call us: (860) 909-8066

5 rating (3 reviews)

Founders Ridge

$300ks - $400ks

Founders Ridge, Middletown, CT

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

1 2

New Heritage Village

773 HERITAGE VLG D, SOUTHBURY, CT, 06488, Southbury, CT 06488

$255,000

2 beds

2 baths

1,071 sq ft

Condo

773 HERITAGE VLG D, SOUTHBURY, CT, 06488

10 MAGGIE MAY WAY, PHILIPSTOWN, NY, 1051...

34 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

Oronoque Village

46 BUCKSKIN LN A, STRATFORD, CT, 06614, Stratford, CT 06614

$559,900

1 beds

2 baths

1,375 sq ft

Condo

46 BUCKSKIN LN A, STRATFORD, CT, 06614

Community: Oronoque Village

The Retreat at Carmel

4 REESE CT, CARMEL, NY, 10512, Carmel, NY 10512

$699,000

2 beds

2 baths

1,979 sq ft

House

4 REESE CT, CARMEL, NY, 10512

Community: The Retreat at Carmel

Heritage Hills

$450,000

1 beds

1 baths

955 sq ft

Condo

128 HERITAGE HILLS DR B, SOMERS, NY, 105...

Community: Heritage Hills

Heritage Hills

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

$649,000

3 beds

2 baths

1,689 sq ft

Condo

156 HERITAGE HLS A, SOMERS, NY, 10589

Community: Heritage Hills

Heritage Village

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

$275,000

2 beds

2 baths

1,432 sq ft

Condo

874 HERITAGE VLG A, SOUTHBURY, CT, 06488

Community: Heritage Village

The Gardens of Wilbraham

137 CHERRY DR 137, WILBRAHAM, MA, 01095, Wilbraham, MA 01095

$400,000

2 beds

2 baths

1,241 sq ft

Condo

137 CHERRY DR 137, WILBRAHAM, MA, 01095

Community: The Gardens of Wilbraham

Rivington

11 MERCY ST 11, DANBURY, CT, 06810, Danbury, CT 06810

$630,000

2 beds

4 baths

1,572 sq ft

11 MERCY ST 11, DANBURY, CT, 06810

Community: Rivington

Heritage Village

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

$399,900

2 beds

2 baths

1,398 sq ft

Condo

701 HERITAGE VLG A, SOUTHBURY, CT, 06488

Community: Heritage Village

Heritage Village

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

$589,900

3 beds

2 baths

1,716 sq ft

Condo

191 HERITAGE VLG A, SOUTHBURY, CT, 06488

Community: Heritage Village

The Village at Oxford Greens

157 COUNTRY CLUB DR 157, OXFORD, CT, 064..., Oxford, CT 06478

$649,900

3 beds

3 baths

2,008 sq ft

Condo

157 COUNTRY CLUB DR 157, OXFORD, CT, 064...

Community: The Village at Oxford Greens

Overlook

2059 SUMMIT LOOP 97, CARMEL, NY, 10512, Carmel, NY 10512

$920,000

2 beds

3 baths

2,873 sq ft

Condo

2059 SUMMIT LOOP 97, CARMEL, NY, 10512

Community: Overlook

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

Questions? Call us: (860) 909-8066

Overlook

2057 SUMMIT LOOP 96, CARMEL, NY, 10512, Carmel, NY 10512

$885,000

2 beds

2 baths

1,948 sq ft

Condo

2057 SUMMIT LOOP 96, CARMEL, NY, 10512

Community: Overlook

Overlook

4091 FAIRWAYS DR 146, CARMEL, NY, 10512, Carmel, NY 10512

$772,000

3 beds

4 baths

2,131 sq ft

Condo

4091 FAIRWAYS DR 146, CARMEL, NY, 10512

Community: Overlook

Overlook

2003 SUMMIT LOOP 82, CARMEL, NY, 10512, Carmel, NY 10512

$799,000

2 beds

2 baths

1,948 sq ft

Condo

2003 SUMMIT LOOP 82, CARMEL, NY, 10512

Community: Overlook

Overlook

4085 FAIRWAYS DR 143, CARMEL, NY, 10512, Carmel, NY 10512

$689,000

3 beds

3 baths

1,931 sq ft

Condo

4085 FAIRWAYS DR 143, CARMEL, NY, 10512

Community: Overlook

Overlook

4087 FAIRWAYS DR 144, CARMEL, NY, 10512, Carmel, NY 10512

$669,000

3 beds

4 baths

2,141 sq ft

Condo

4087 FAIRWAYS DR 144, CARMEL, NY, 10512

Community: Overlook

Heritage Village

24-B HERITAGE CRST B, SOUTHBURY, CT, 064..., Southbury, CT 06488

$419,900

2 beds

2 baths

1,217 sq ft

Condo

24-B HERITAGE CRST B, SOUTHBURY, CT, 064...

Community: Heritage Village

Heritage Village

593 HERITAGE VLG D, SOUTHBURY, CT, 06488, Southbury, CT 06488

$205,000

2 beds

2 baths

1,044 sq ft

Condo

593 HERITAGE VLG D, SOUTHBURY, CT, 06488

Community: Heritage Village

Stoneleigh Woods at Carmel

205 EGRETS LNDG 205, CARMEL, NY, 10512, Carmel, NY 10512

$475,000

2 beds

2 baths

1,344 sq ft

Condo

205 EGRETS LNDG 205, CARMEL, NY, 10512

Community: Stoneleigh Woods at Carmel

Heritage Village

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

$235,000

2 beds

2 baths

1,076 sq ft

Condo

147 HERITAGE VLG A, SOUTHBURY, CT, 06488

Community: Heritage Village

Heritage Village

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

$204,000

2 beds

2 baths

1,032 sq ft

Condo

22 HERITAGE VLG B, SOUTHBURY, CT, 06488

Community: Heritage Village

Jefferson Village

5 DEVON CT B, YORKTOWN, NY, 10598, Yorktown, NY 10598

$385,000

2 beds

1 baths

989 sq ft

Condo

5 DEVON CT B, YORKTOWN, NY, 10598

Community: Jefferson Village

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

Questions? Call us: (860) 909-8066

Liberty at Newtown

76 SUZIE DR 76, NEWTOWN, CT, 06470, Newtown, CT 06470

$648,000

2 beds

3 baths

2,341 sq ft

Condo

76 SUZIE DR 76, NEWTOWN, CT, 06470

Community: Liberty at Newtown

Heritage Village

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

$259,000

2 beds

2 baths

1,432 sq ft

Condo

804 HERITAGE VLG B, SOUTHBURY, CT, 06488

Community: Heritage 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.

Want more information about active adult communities around Winsted?

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79 communities

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Winsted, CT 55+ active adult communities & homes for sale - Page 2

79 communities near Winsted

163 homes near Winsted

2 beds

2 baths

1,071 sq ft

Condo

2 beds

3 baths

1,550 sq ft

Condo

2 beds

2 baths

1,747 sq ft

Condo

2 beds

2 baths

1,000 sq ft

Condo

2 beds

2 baths

1,974 sq ft

Condo

2 beds

2 baths

1,432 sq ft

Condo

2 beds

2 baths

1,328 sq ft

Condo

2 beds

2 baths

1,398 sq ft

Condo

1 beds

2 baths

967 sq ft

Condo

3 beds

2 baths

2,008 sq ft

Condo

2 beds

2 baths

1,265 sq ft

Condo

2 beds

2 baths

1,432 sq ft

Condo

3 beds

2 baths

2,152 sq ft

2 beds

2 baths

1,044 sq ft

Condo

2 beds

2 baths

1,285 sq ft

Condo

2 beds

3 baths

1,545 sq ft

Condo

1 beds

2 baths

1,375 sq ft

Condo

2 beds

2 baths

1,979 sq ft

House

1 beds

1 baths

955 sq ft

Condo

3 beds

2 baths