Cheshire, CT 55+ active adult communities & homes for sale - Page 4

231 homes near Cheshire

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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

Leisure Village

$100ks - $300ks

Leisure Village, Ridge, NY

Resale Only | 55+ age-restricted | Built 1969 - 1986 | 1,500 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

3.7 rating (3 reviews)

Greenwood Village

$100ks

Greenwood Village, Manorville, NY

Resale Only | 55+ age-restricted | Built 1980 - 2000 | 512 homes

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

Questions? Call us: (475) 244-9781

4 rating (8 reviews)

Glenwood Village

$100ks - $200ks

Glenwood Village, Riverhead, NY

New and Resale | 55+ age-restricted | Built 1959 - present | 588 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

Meadowbrook Pointe Athlet...

$700ks - $1Ms

Meadowbrook Pointe Athlet..., Westbury, NY

Resale Only | 55+ age-restricted | Built 2015 - 2016 | 720 homes

Overlook

$600ks - $900ks

Overlook, Carmel, NY

New Construction | 55+ age-restricted | 300 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.

Leisure Knoll

$200ks - $400ks

Leisure Knoll, Ridge, NY

Resale Only | 55+ age-restricted | Built 1972 - 1982 | 701 homes

The Waterways at Moriches

$300ks - $600ks

The Waterways at Moriches, Moriches, NY

Resale Only | 55+ age-restricted | Built 1985 - 1999 | 343 homes

The Retreat at Carmel

$300ks - $800ks

The Retreat at Carmel, Carmel, NY

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

5 rating (1 reviews)

Encore Atlantic Shores

$500ks - $800ks

Encore Atlantic Shores, Eastport, NY

Resale Only | 55+ age-restricted | Built 2004 - 2011 | 240 homes

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

Questions? Call us: (475) 244-9781

Spring Lake Village

$100ks - $200ks

Spring Lake Village, Southington, CT

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

The Greens at Half Hollow

$600ks - $1Ms

The Greens at Half Hollow, Melville, NY

Resale Only | 55+ age-restricted | Built 1994 - 2005 | 1,200 homes

5 rating (2 reviews)

Fairfield at St. James

$300ks - $500ks

Fairfield at St. James, St. James, NY

Resale Only | 55+ age-restricted | Built 1972 - 1989 | 653 homes

Rivington

$300ks - $900ks

Rivington, Danbury, CT

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

The Villas at Narraganset...

$400ks

The Villas at Narraganset..., Lindenhurst, NY

Resale Only | 55+ age-restricted | Built 2004 - 2005 | 138 homes

The Seasons at East Meado...

$400ks - $600ks

The Seasons at East Meado..., East Meadow, NY

Resale Only | 55+ age-restricted | Built 2009 - 2012 | 404 homes

5 rating (1 reviews)

Encore at Lake Grove

$500ks - $700ks

Encore at Lake Grove, Lake Grove, NY

Resale Only | 55+ age-restricted | Built 2006 - 2007 | 228 homes

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

Questions? Call us: (475) 244-9781

The Coves at Melville

$500ks

The Coves at Melville, Melville, NY

Resale Only | 62+ age-restricted | Built 2004 - 2005 | 175 homes

5 rating (1 reviews)

Westhampton Pines

$900ks - $1Ms

Westhampton Pines, Westhampton, NY

Resale Only | 55+ age-restricted | Built 2005 - 2013 | 189 homes

Dutchgate

$300ks - $500ks

Dutchgate, Valley Stream, NY

Resale Only | 55+ age-restricted | Built 2009 - 2015 | 348 homes

5 rating (1 reviews)

Newtown Woods

$300ks - $500ks

Newtown Woods, Newtown, CT

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

Leisure Glen

$300ks - $400ks

Leisure Glen, Ridge, NY

Resale Only | 55+ age-restricted | Built 1985 - 2010 | 646 homes

Regency at Woodbridge

$500ks - $700ks

Regency at Woodbridge, Woodbridge, CT

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

Stone Ridge Estates

$500ks - $600ks

Stone Ridge Estates, Dix Hills, NY

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

Kensington Estates

$1Ms

Kensington Estates, Woodbury, NY

New Construction | 55+ age-restricted | Built 2019 - 2021 | 80 homes

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

Questions? Call us: (475) 244-9781

South Pond Village

$300ks - $400ks

South Pond Village, Bloomfield, CT

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

Fairview at Oxford Greens

$400ks - $600ks

Fairview at Oxford Greens, Oxford, CT

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

Bartlett Hill

$300ks - $400ks

Bartlett Hill, Portland, CT

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

3.5 rating (2 reviews)

Foxwood Village

$200ks - $400ks

Foxwood Village, Calverton, NY

Resale Only | 55+ age-restricted | Built 1986 - 2007 | 294 homes

Baldwin Station

$400ks

Baldwin Station, Milford, CT

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

Liberty at Newtown

$300ks - $400ks

Liberty at Newtown, Newtown, CT

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

The Manors at The Colony ...

$300ks - $400ks

The Manors at The Colony ..., Shirley, NY

New Construction | 55+ age-restricted | Built 2013 - present | 150 homes

Park Glen

$300ks - $500ks

Park Glen, New Milford, CT

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

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

Questions? Call us: (475) 244-9781

Oak Meadow Estates

$200ks - $300ks

Oak Meadow Estates, Torrington, CT

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

Regency at Prospect

$300ks - $400ks

Regency at Prospect, Prospect, CT

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

1 2 3...4

Encore Atlantic Shores

6 OVATION PL, EASTPORT, NY, 11941, Eastport, NY 11941

$795,000

2 beds

2 baths

2,150 sq ft

Condo

6 OVATION PL, EASTPORT, NY, 11941

116 EXMORE CT UNIT B, RIDGE, NY, 11961

Community: Leisure Village

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

Questions? Call us: (475) 244-9781

The Retreat at Carmel

2 BLAIR HEIGHTS 3317, CARMEL, NY, 10512, Carmel, NY 10512

$459,900

2 beds

2 baths

1,323 sq ft

Condo

2 BLAIR HEIGHTS 3317, CARMEL, NY, 10512

Community: The Retreat at Carmel

Dutchgate

817 WILLOW LN, VALLEY STREAM, NY, 11580, Valley Stream, NY 11580

$514,990

2 beds

2 baths

941 sq ft

Condo

817 WILLOW LN, VALLEY STREAM, NY, 11580

Community: Dutchgate

Meadowbrook Pointe Athletic Club & Spa

365 TROTTING LN, WESTBURY, NY, 11590, Westbury, NY 11590

$799,999

1 beds

2 baths

1,128 sq ft

Condo

365 TROTTING LN, WESTBURY, NY, 11590

Community: Meadowbrook Pointe Athletic Club & Spa

Heritage Hills

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

$600,000

2 beds

2 baths

1,470 sq ft

Condo

537 HERITAGE HLS D, SOMERS, NY, 10589

Community: Heritage Hills

The Summit at Bethel

32 HUNTING RIDGE LN # 32, BETHEL, CT, 06..., Bethel, CT 06801

$689,000

3 beds

4 baths

2,090 sq ft

Condo

32 HUNTING RIDGE LN # 32, BETHEL, CT, 06...

Community: The Summit at Bethel

Country Pointe Plainview

21105 ASPENWOOD DR, PLAINVIEW, NY, 11803, Plainview, NY 11803

$1,250,000

2 beds

2 baths

1,475 sq ft

Condo

21105 ASPENWOOD DR, PLAINVIEW, NY, 11803

Community: Country Pointe Plainview

Leisure Village

373 WOODBRIDGE DR B, RIDGE, NY, 11961, Ridge, NY 11961

$415,000

2 beds

1 baths

1,171 sq ft

Condo

373 WOODBRIDGE DR B, RIDGE, NY, 11961

Community: Leisure Village

The Villas at Narragansett

816 NARRAGANSETT VILLAS DR 816, BABYLON,..., Babylon, NY 11757

$549,999

2 beds

2 baths

1,215 sq ft

Condo

816 NARRAGANSETT VILLAS DR 816, BABYLON,...

Condo

360 WOODBRIDGE DR A, RIDGE, NY, 11961

Community: Leisure Village

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

Questions? Call us: (475) 244-9781

Oronoque Village

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

$524,900

1 beds

3 baths

1,438 sq ft

Condo

617 CHEROKEE LN B, STRATFORD, CT, 06614

Community: Oronoque Village

Heritage Village

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

$319,000

2 beds

2 baths

1,432 sq ft

Condo

98 HERITAGE VLG A, SOUTHBURY, CT, 06488

Community: Heritage Village

Eagles Walk at East Quogue

104 AERIE WAY, EAST QUOGUE, NY, 11942, East Quogue, NY 11942

$549,900

2 beds

2 baths

1,341 sq ft

Condo

104 AERIE WAY, EAST QUOGUE, NY, 11942

Community: Eagles Walk at East Quogue

Heritage Hills

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

$675,000

2 beds

2 baths

1,500 sq ft

Condo

55 HERITAGE HLS A, SOMERS, NY, 10589

Community: Heritage Hills

Heritage Hills

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

$625,000

2 beds

2 baths

1,559 sq ft

Condo

443 HERITAGE HLS A, SOMERS, NY, 10589

Community: Heritage Hills

Heritage Village

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

$364,900

2 beds

2 baths

1,398 sq ft

Condo

123 HERITAGE VLG B, SOUTHBURY, CT, 06488

Community: Heritage Village

Baldwin Station

7 FIRE THORN LN # 7, MILFORD, CT, 06461, Milford, CT 06461

$679,950

2 beds

3 baths

2,331 sq ft

Condo

7 FIRE THORN LN # 7, MILFORD, CT, 06461

Community: Baldwin Station

The Waterways at Moriches

477 WOODSCREEK CT, MORICHES, NY, 11955, Moriches, NY 11955

$565,000

3 beds

2 baths

1,839 sq ft

Condo

477 WOODSCREEK CT, MORICHES, NY, 11955

Community: The Waterways at Moriches

Oronoque Village

766 NYACK LN B, STRATFORD, CT, 06614, Stratford, CT 06614

$649,000

1 beds

3 baths

1,438 sq ft

Condo

766 NYACK LN B, STRATFORD, CT, 06614

Community: Oronoque Village

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

Questions? Call us: (475) 244-9781

Heritage Hills

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

$675,000

3 beds

2 baths

1,689 sq ft

Condo

59 HERITAGE HLS A, SOMERS, NY, 10589

Community: Heritage Hills

Bartlett Hill

9 PEAR ORCHARD RD # 9, PORTLAND, CT, 064..., Portland, CT 06480

2 beds

4 baths

1,957 sq ft

Condo

2042 SUMMIT LOOP # 58, CARMEL, NY, 10512

Community: Overlook

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

Questions? Call us: (475) 244-9781

Overlook

2080 SUMMIT LOOP # 75, CARMEL, NY, 10512, Carmel, NY 10512

$899,000

2 beds

3 baths

2,496 sq ft

Condo

2080 SUMMIT LOOP # 75, CARMEL, NY, 10512

Community: Overlook

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

1 2 3 4 5…6

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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231 homes

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Cheshire, CT 55+ active adult communities & homes for sale - Page 4

129 communities near Cheshire

231 homes near Cheshire

2 beds

2 baths

2,150 sq ft

Condo

3 beds

4 baths

1,794 sq ft

Condo

2 beds

2 baths

1,415 sq ft

Condo

2 beds

1 baths

900 sq ft

Condo

2 beds

1 baths

875 sq ft

Condo

2 beds

2 baths

1,323 sq ft

Condo

2 beds

2 baths

941 sq ft

Condo

1 beds

2 baths

1,128 sq ft

Condo

2 beds

2 baths

1,470 sq ft

Condo

3 beds

4 baths

2,090 sq ft

Condo

2 beds

2 baths

1,475 sq ft

Condo

2 beds

1 baths

1,171 sq ft

Condo

2 beds

2 baths

1,215 sq ft

Condo

2 beds

1 baths

819 sq ft

Condo

2 beds

2 baths

1,323 sq ft

Condo

2 beds

2 baths

1,590 sq ft

Condo

3 beds

3 baths

3,000 sq ft

Condo

2 beds

1 baths

1,074 sq ft

Condo

2 beds

3 baths

1,133 sq ft

Condo

2 beds