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

129 communities near Cheshire

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5 rating (2 reviews)

Benson Woods

$400Ks - $600Ks

Benson Woods, Middlebury, CT

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

Shaker Heights

$400Ks - $500Ks

Shaker Heights, Enfield, CT

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

Stone Ridge Estates

$700Ks

Stone Ridge Estates, Dix Hills, NY

Resale Only | 55+ age-restricted | Built 2004 - 2013 | 76 homes

5 rating (3 reviews)

Founders Ridge

$500Ks - $600Ks

Founders Ridge, Middletown, CT

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

Breton Hills

$600Ks

Breton Hills, Glen Cove, NY

New Construction | 55+ age-restricted | Built 2019 - present | 72 homes

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

Questions? Call us: (475) 244-9781

The Polo Club at Islandia

$600Ks

The Polo Club at Islandia, Islandia, NY

New Construction | 55+ age-restricted | Built 2019 - present | 72 homes

Long Hill Village

$300Ks - $400Ks

Long Hill Village, Trumbull, CT

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

Regency at Woodbridge

$500Ks - $600Ks

Regency at Woodbridge, Woodbridge, CT

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

The Village at Hunt Glen

$300Ks

The Village at Hunt Glen, Granby, CT

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

Sonoma Woods

$300Ks

Sonoma Woods, Middletown, CT

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

Stoneleigh Woods at Carme...

$400Ks

Stoneleigh Woods at Carme..., Carmel, NY

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

Eagles Walk at East Quogu...

$500Ks

Eagles Walk at East Quogu..., East Quogue, NY

Resale Only | 55+ age-restricted | Built 2004 - 2014 | 67 homes

Hopmeadow Place

$200Ks - $300Ks

Hopmeadow Place, Simsbury, CT

Resale Only | 55+ age-restricted | Built 2005 - 2005 | 66 homes

Whitney Glen

$500Ks - $600Ks

Whitney Glen, Westport, CT

Resale Only | 55+ age-restricted | Built 1982 - 1982 | 62 homes

RiverWalk

$500Ks - $600Ks

RiverWalk, Branford, CT

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

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

Questions? Call us: (475) 244-9781

The Village at Buckingham

$500Ks - $600Ks

The Village at Buckingham, Avon, CT

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

The Atrium of Portland

<$100k

The Atrium of Portland, Portland, CT

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

Autumn Fields

$200Ks - $300Ks

Autumn Fields, Enfield, CT

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

77 Sunset Lane

$400Ks - $700Ks

77 Sunset Lane, Ridgefield, CT

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

Evergreen

$500Ks

Evergreen, Cromwell, CT

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

Regency Meadows

$500Ks

Regency Meadows, Trumbull, CT

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

Gloria Commons

$400Ks

Gloria Commons, Milford, CT

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

Villas at Seminary Hill

$400Ks

Villas at Seminary Hill, Carmel, NY

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

Eastport Meadows

$400Ks

Eastport Meadows, Eastport, NY

Resale Only | 55+ age-restricted | Built 2009 - 2016 | 50 homes

Bramble Ridge

$400Ks - $500Ks

Bramble Ridge, Suffield, CT

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

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

Questions? Call us: (475) 244-9781

Chimney Hill

$500Ks - $700Ks

Chimney Hill, Farmington, CT

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

Village Vistas

$800Ks - $1Ms

Village Vistas, Port Jefferson, NY

Resale Only | 55+ age-restricted | Built 2013 - 2017 | 43 homes

Harbor View Estates

$400Ks - $600Ks

Harbor View Estates, Copiague, NY

New Construction | 55+ age-restricted | Built 2017 - 2018 | 40 homes

Forest Mews

$300Ks - $400Ks

Forest Mews, Avon, CT

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

Clockmaker's Hill

$100Ks

Clockmaker's Hill, Winsted, CT

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

Hidden Harbor Estates

$500Ks - $600Ks

Hidden Harbor Estates, Copiague, NY

Resale Only | 55+ age-restricted | Built 2010 - 2015 | 38 homes

Billingsgate

$400Ks - $600Ks

Billingsgate, Simsbury, CT

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

Bidwell Village

$300Ks - $400Ks

Bidwell Village, Coventry, CT

New Construction | 55+ age-restricted | Built 2020 - present | 37 homes

Stratford Park

$900Ks

Stratford Park, Melville, NY

Resale Only | 55+ age-restricted | Built 2011 - 2013 | 36 homes

Boulder Brook

$200Ks

Boulder Brook, Prospect, CT

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

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

Questions? Call us: (475) 244-9781

The Woods at Dunham Pond

$400Ks - $500Ks

The Woods at Dunham Pond, New Fairfield, CT

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

Knickerbocker Bay Club

$700Ks - $3Ms

Knickerbocker Bay Club, Port Washington, NY

New and Resale | 55+ age-restricted | Built 2014 - present | 32 homes

Jessup's Landing

$1Ms

Jessup's Landing, Quogue, NY

New and Resale | 55+ age-restricted | Built 2009 - 2016 | 31 homes

Oak Meadow Estates

$400Ks

Oak Meadow Estates, Torrington, CT

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

Autumn Estates

$500Ks - $600Ks

Autumn Estates, Farmington, CT

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

191 HERITAGE VLG A, SOUTHBURY, CT, 06488

Community: Heritage Village

The Village at Oxford Greens

930 TILLINGHAST DR # 930, OXFORD, CT, 06..., Oxford, CT 06478

$759,900

2 beds

3 baths

2,365 sq ft

930 TILLINGHAST DR # 930, OXFORD, CT, 06...

Community: The Village at Oxford Greens

Heritage Village

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

$369,900

2 beds

2 baths

1,398 sq ft

Condo

865 HERITAGE VLG B, SOUTHBURY, CT, 06488

85 CLEARVIEW CT # 85, SOUTHINGTON, CT, 0...

Community: Spring Lake Village

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

Questions? Call us: (475) 244-9781

Heritage Village

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

$384,900

2 beds

2 baths

1,398 sq ft

Condo

123 HERITAGE VLG B, SOUTHBURY, CT, 06488

Community: Heritage Village

Oronoque Village

617 CHEROKEE LN B, STRATFORD, CT, 06614, Stratford, CT 06614

$534,999

1 beds

3 baths

1,438 sq ft

Condo

617 CHEROKEE LN B, STRATFORD, CT, 06614

Community: Oronoque Village

Heritage Village

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

$204,900

2 beds

2 baths

1,044 sq ft

Condo

73 HERITAGE VLG D, SOUTHBURY, CT, 06488

Community: Heritage Village

Heritage Village

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

$379,000

2 beds

2 baths

1,398 sq ft

Condo

876 HERITAGE VLG A, SOUTHBURY, CT, 06488

Community: Heritage Village

Heritage Village

26 HERITAGE CRST C, SOUTHBURY, CT, 06488, Southbury, CT 06488

$399,900

2 beds

2 baths

1,217 sq ft

Condo

26 HERITAGE CRST C, SOUTHBURY, CT, 06488

Community: Heritage Village

Heritage Village

25 HERITAGE CRST C, SOUTHBURY, CT, 06488, Southbury, CT 06488

$449,000

2 beds

2 baths

1,447 sq ft

Condo

25 HERITAGE CRST C, SOUTHBURY, CT, 06488

Community: Heritage Village

Oronoque Village

193 BAYFIELD LN B, STRATFORD, CT, 06614, Stratford, CT 06614

$559,000

1 beds

3 baths

1,620 sq ft

Condo

193 BAYFIELD LN B, STRATFORD, CT, 06614

Community: Oronoque Village

The Village at Oxford Greens

185 COUNTRY CLUB DR # 185, OXFORD, CT, 0..., Oxford, CT 06478

$660,000

3 beds

3 baths

2,595 sq ft

Condo

185 COUNTRY CLUB DR # 185, OXFORD, CT, 0...

Community: The Village at Oxford Greens

Fairview at Oxford Greens

712 CHAMPIONSHIP DR # 712, OXFORD, CT, 0..., Oxford, CT 06478

$615,000

2 beds

2 baths

1,546 sq ft

Condo

712 CHAMPIONSHIP DR # 712, OXFORD, CT, 0...

Community: Fairview at Oxford Greens

The Village at Oxford Greens

$615,000

2 beds

2 baths

1,546 sq ft

Condo

712 CHAMPIONSHIP DR # 712, OXFORD, CT, 0...

21 HERITAGE LN # 60, WOODBRIDGE, CT, 065...

Community: Regency at Woodbridge

Oronoque Village

164 BISON LN A, STRATFORD, CT, 06614, Stratford, CT 06614

$479,999

1 beds

2 baths

1,175 sq ft

Condo

164 BISON LN A, STRATFORD, CT, 06614

Condo

21 OAK MEADOW LN # 21, HARWINTON, CT, 06...

Community: Oak Meadow Estates

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Frequently Asked Questions

What size 55+ communities are there in Cheshire?

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

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

The smallest 55+ community in Cheshire has 88 homes, the largest has 88 homes, and the average community consists of 88 homes.

Are there gated 55+ communities in Cheshire?

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

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Want to learn more about 55+ communities in Cheshire?

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129 communities near Cheshire

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

129 communities near Cheshire

228 homes near Cheshire

1 beds

3 baths

1,575 sq ft

Condo

1 beds

2 baths

1,300 sq ft

Condo

3 beds

2 baths

1,716 sq ft

Condo

2 beds

3 baths

2,365 sq ft

2 beds

2 baths

1,398 sq ft

Condo

3 beds

2 baths

1,716 sq ft

Condo

3 beds

2 baths

1,716 sq ft

Condo

2 beds

2 baths

1,063 sq ft

Condo

2 beds

2 baths

1,044 sq ft

Condo

2 beds

2 baths

1,323 sq ft

Condo

3 beds

3 baths

1,717 sq ft

3 beds

3 baths

1,426 sq ft

Condo

1 beds

3 baths

1,620 sq ft

Condo

2 beds

2 baths

1,432 sq ft

Condo

1 beds

2 baths

1,028 sq ft

Condo

2 beds

2 baths

1,398 sq ft

Condo

1 beds

3 baths

1,438 sq ft

Condo

2 beds

2 baths

1,044 sq ft

Condo

2 beds

2 baths

1,398 sq ft

Condo

2 beds

2 baths

1,217 sq ft