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Cheshire, CT 55+ active adult communities & homes for sale - Page 8

Living in Cheshire

Residents of 55+ communities in Cheshire are loving this New Haven County town. Located in an area surrounded by greenscapes and plenty of interesting natural features, the town…

Residents of 55+ communities in Cheshire are loving this New Haven County town. Located in an area surrounded by greenscapes and plenty of interesting natural features, the town also has a suburban culture with quiet neighborhoods and many local amenities like clubs and facilities that make it easy to find new hobbies.

Climate & Geography

The climate in Central Connecticut is categorized as humid continental, which features four distinct seasons. Summers are generally hot and humid, while winters are cold and snowy. Residents can expect higher-than-average amounts of rain and snow, and approximately 198 sunny days throughout the year.

Recreation, Culture & Entertainment

Some of the top attractions in Cheshire include Barker Character Comic and Cartoon Museum, Roaring Brook Park, Bartlem Park, Drazen Orchards, Cheshire Hollow Farm, and Cheshire Historical Society. The town also offers various programs for the community including transportation services into and out of town.

There are plentiful parks and outdoor spaces within the town where residents can get outside and enjoy nature, and additional outdoor recreation activities such as hiking, fishing, and skiing, can be found at the nearby Naugatuck State Park.

Cheshire is also within driving distance of Hartford and New Haven, providing the perfect opportunity for day trips and weekend getaways to enjoy everything these cities have to offer.

Cost of Living & Taxes

The cost of living in Cheshire is higher than the state and national average. This is primarily due to the high cost of housing and homes, while other factors like groceries, utilities, and transportation are just slightly higher than the national average.

The effective income tax rate is as low as three percent and as high as 6.99 percent. Retirement income including Social Security benefits are fully exempt for taxpayers with limited income. Other retirement income like military pensions and railroad retirement benefits are fully exempt. Qualifying homeowners 65+ can also receive property tax credits as well as additional municipality tax reliefs.

Health Care

Residents of 55+ communities in Cheshire have several area health care options to choose from. Among them are various hospitals recognized by U.S. News for high performance in many procedures and conditions. The closest hospital is St. Mary’s Hospital in Waterbury, about six miles away. Other choices include the Hospital of Central Connecticut, Middlesex Hospital, Yale New Haven Hospital, Hartford Hospital, and St. Francis Hospital and Medical Center, all within 20 miles.

Frequently Asked Questions


305 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
3 rating (2 reviews) Heritage Hills
$500ks - $900ks
Heritage Hills, Somers, NY
Resale Only | Age-targeted | Built 1974 - 2006 | 2,600 homes
3.7 rating (3 reviews) Greenwood Village
$100ks
Greenwood Village, Manorville, NY
Resale Only | 55+ age-restricted | Built 1980 - 2000 | 512 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 Cheshire? 55places can help!
Questions? Call us: (475) 244-9781
Leisure Village
$100ks - $300ks
Leisure Village, Ridge, NY
Resale Only | 55+ age-restricted | Built 1969 - 1986 | 1,500 homes
5 rating (2 reviews) Oronoque Village
$200ks - $400ks
Oronoque Village, Stratford, CT
Resale Only | 55+ age-restricted | Built 1971 - 1977 | 929 homes
The Waterways at Moriches
$300ks - $600ks
The Waterways at Moriches, Moriches, NY
Resale Only | 55+ age-restricted | Built 1985 - 1999 | 343 homes
Leisure Glen
$300ks - $400ks
Leisure Glen, Ridge, NY
Resale Only | 55+ age-restricted | Built 1985 - 2010 | 646 homes
Leisure Knoll
$200ks - $400ks
Leisure Knoll, Ridge, NY
Resale Only | 55+ age-restricted | Built 1972 - 1982 | 701 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 (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 Greens at Half Hollow
$600ks - $1Ms
The Greens at Half Hollow, Melville, NY
Resale Only | 55+ age-restricted | Built 1994 - 2005 | 1,200 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
4 rating (8 reviews) Glenwood Village
$100ks - $200ks
Glenwood Village, Riverhead, NY
New and Resale | 55+ age-restricted | Built 1959 - present | 588 homes
HarborView
$600ks - $1Ms
HarborView, Port Washington, NY
Resale Only | 55+ age-restricted | Built 2002 - 2004 | 270 homes
Want to learn more about 55+ communities in Cheshire? 55places can help!
Questions? Call us: (475) 244-9781
Fairview at Oxford Greens
$400ks - $600ks
Fairview at Oxford Greens, Oxford, CT
New and Resale | 55+ age-restricted | Built 2019 - present | 125 homes
5 rating (1 reviews) Newtown Woods
$300ks - $500ks
Newtown Woods, Newtown, CT
New and Resale | 55+ age-restricted | Built 2011 - present | 178 homes
3.5 rating (2 reviews) Foxwood Village
$200ks - $400ks
Foxwood Village, Calverton, NY
Resale Only | 55+ age-restricted | Built 1986 - 2007 | 294 homes
Meadow Brook Estates
$300ks - $400ks
Meadow Brook Estates, Oxford, CT
Resale Only | 55+ age-restricted | Built 2003 - 2020 | 246 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) Encore Atlantic Shores
$500ks - $800ks
Encore Atlantic Shores, Eastport, NY
Resale Only | 55+ age-restricted | Built 2004 - 2011 | 240 homes
Country Pointe Plainview
$700ks - $1Ms
Country Pointe Plainview, Plainview, NY
New Construction | 55+ age-restricted | Built 2017 - present | 660 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
5 rating (1 reviews) Westhampton Pines
$900ks - $1Ms
Westhampton Pines, Westhampton, NY
Resale Only | 55+ age-restricted | Built 2005 - 2013 | 189 homes
1 rating (1 reviews) Plymouth Estates at Mount...
$400ks - $500ks
Plymouth Estates at Mount..., Mount Sinai, NY
Resale Only | 55+ age-restricted | Built 2006 - 2013 | 285 homes
Stoneleigh Woods at River...
$500ks
Stoneleigh Woods at River..., Riverhead, NY
Resale Only | 55+ age-restricted | Built 2007 - 2016 | 176 homes
Meadowbrook Pointe Athlet...
$700ks - $1Ms
Meadowbrook Pointe Athlet..., Westbury, NY
Resale Only | 55+ age-restricted | Built 2015 - 2016 | 720 homes
Want to learn more about 55+ communities in Cheshire? 55places can help!
Questions? Call us: (475) 244-9781
Overlook
$600ks - $900ks
Overlook, Carmel, NY
New Construction | 55+ age-restricted | 300 homes
Saddle Lakes
$400ks - $500ks
Saddle Lakes, Riverhead, NY
Resale Only | 55+ age-restricted | Built 2000 - 2002 | 196 homes
Kensington Estates
$1Ms
Kensington Estates, Woodbury, NY
New Construction | 55+ age-restricted | Built 2019 - 2021 | 80 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.
Harbor View Estates
$400ks - $600ks
Harbor View Estates, Copiague, NY
New Construction | 55+ age-restricted | Built 2017 - 2018 | 40 homes
4.6 rating (9 reviews) Meadowbrook Pointe Links ...
$300ks - $700ks
Meadowbrook Pointe Links ..., Medford, NY
New and Resale | 55+ age-restricted | Built 2010 - present | 280 homes
Windcrest East
$400ks - $500ks
Windcrest East, Calverton, NY
Resale Only | 55+ age-restricted | Built 2004 - 2005 | 126 homes
Woodridge Strathmore Terr...
$200ks - $300ks
Woodridge Strathmore Terr..., Mount Sinai, NY
Resale Only | 55+ age-restricted | Built 1974 - 1985 | 226 homes
Dutchgate
$300ks - $500ks
Dutchgate, Valley Stream, NY
Resale Only | 55+ age-restricted | Built 2009 - 2015 | 348 homes
Spring Lake Village
$100ks - $200ks
Spring Lake Village, Southington, CT
Resale Only | 55+ age-restricted | Built 1970 - 2004 | 640 homes
5 rating (1 reviews) Sunken Pond Estates
$400ks
Sunken Pond Estates, Riverhead, NY
Resale Only | 55+ age-restricted | Built 2003 - 2005 | 194 homes
Regency Meadows
$500ks
Regency Meadows, Trumbull, CT
Resale Only | 55+ age-restricted | Built 2003 - 2005 | 51 homes
Want to learn more about 55+ communities in Cheshire? 55places can help!
Questions? Call us: (475) 244-9781
The Villas at Narraganset...
$400ks
The Villas at Narraganset..., Lindenhurst, NY
Resale Only | 55+ age-restricted | Built 2004 - 2005 | 138 homes
Granite Woods
$600ks - $700ks
Granite Woods, Middlebury, CT
New Construction | 55+ age-restricted | Built 2020 - present | 24 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.
123...4
Liberty at Newtown 25 FRANKLIN CT 25, NEWTOWN, CT, 06470, Newtown, CT 06470
$499,000

2 beds

|

2 baths

|

1,413 sq ft

|

Condo

25 FRANKLIN CT 25, NEWTOWN, CT, 06470
Community: Liberty at Newtown
Leisure Knoll 183 KINGSTON DR, BROOKHAVEN, NY, 11961, Brookhaven, NY 11961
$414,500

2 beds

|

1 baths

|

960 sq ft

|

Condo

183 KINGSTON DR, BROOKHAVEN, NY, 11961
Community: Leisure Knoll
The Village at Oxford Greens 527 PUTTING GREEN LN 527, OXFORD, CT, 06..., Oxford, CT 06478
$650,000

3 beds

|

3 baths

|

2,008 sq ft

|

Condo

527 PUTTING GREEN LN 527, OXFORD, CT, 06...
Country Pointe Plainview 15103 ASPENWOOD DR, OYSTER BAY, NY, 1180..., Oyster Bay, NY 11803
$1,035,000

2 beds

|

2 baths

|

1,335 sq ft

|

Condo

15103 ASPENWOOD DR, OYSTER BAY, NY, 1180...
Harbor View Estates 206 ANCHOR CT, BABYLON, NY, 11726, Babylon, NY 11726
$589,990

2 beds

|

2 baths

|

1,200 sq ft

|

Condo

206 ANCHOR CT, BABYLON, NY, 11726
Community: Harbor View Estates
Want to learn more about 55+ communities in Cheshire? 55places can help!
Questions? Call us: (475) 244-9781
The Manors at The Colony Preserve 40 GREENTREE CT, BROOKHAVEN, NY, 11967, Brookhaven, NY 11967
$530,000

2 beds

|

2 baths

|

1,360 sq ft

|

Condo

40 GREENTREE CT, BROOKHAVEN, NY, 11967
The Waterways at Moriches 377 QUARRY POND CT, BROOKHAVEN, NY, 1195..., Brookhaven, NY 11955
$549,999

3 beds

|

2 baths

|

2,141 sq ft

|

Condo

377 QUARRY POND CT, BROOKHAVEN, NY, 1195...
Regency Meadows 108 IMPERIAL CT 108, TRUMBULL, CT, 06611, Trumbull, CT 06611
$719,000

2 beds

|

3 baths

|

2,891 sq ft

|

Condo

108 IMPERIAL CT 108, TRUMBULL, CT, 06611
Community: Regency Meadows
Foxwood Village 1407 MIDDLE RD 83, BROOKHAVEN, NY, 11933, Brookhaven, NY 11933
$399,999

2 beds

|

2 baths

|

1,444 sq ft

|

Manufactured Home

1407 MIDDLE RD 83, BROOKHAVEN, NY, 11933
Community: Foxwood Village
Plymouth Estates at Mount Sinai 26 ROSE LN, BROOKHAVEN, NY, 11766, Brookhaven, NY 11766
$520,000

2 beds

|

2 baths

|

1,563 sq ft

|

Condo

26 ROSE LN, BROOKHAVEN, NY, 11766
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 Riverhead 47 STONELEIGH DR, RIVERHEAD, NY, 11901, Riverhead, NY 11901
$639,000

2 beds

|

3 baths

|

1,942 sq ft

|

Condo

47 STONELEIGH DR, RIVERHEAD, NY, 11901
Heritage Village 916 HERITAGE VLG A, SOUTHBURY, CT, 06488, Southbury, CT 06488
$379,000

2 beds

|

2 baths

|

1,432 sq ft

|

Condo

916 HERITAGE VLG A, SOUTHBURY, CT, 06488
Community: Heritage Village
Heritage Village 14 HERITAGE CIR B, SOUTHBURY, CT, 06488, Southbury, CT 06488
$239,000

2 beds

|

2 baths

|

1,000 sq ft

|

Condo

14 HERITAGE CIR B, SOUTHBURY, CT, 06488
Community: Heritage Village
The Manors at The Colony Preserve 17 GREENTREE CT, BROOKHAVEN, NY, 11967, Brookhaven, NY 11967
$549,000

2 beds

|

2 baths

|

1,557 sq ft

|

Condo

17 GREENTREE CT, BROOKHAVEN, NY, 11967
Heritage Village 59 HERITAGE VLG F, SOUTHBURY, CT, 06488, Southbury, CT 06488
$209,000

2 beds

|

2 baths

|

1,308 sq ft

|

Condo

59 HERITAGE VLG F, SOUTHBURY, CT, 06488
Community: Heritage Village
Stoneleigh Woods at Riverhead 156 STONELEIGH DR, RIVERHEAD, NY, 11901, Riverhead, NY 11901
$639,000

2 beds

|

3 baths

|

1,942 sq ft

|

Condo

156 STONELEIGH DR, RIVERHEAD, NY, 11901
Want to learn more about 55+ communities in Cheshire? 55places can help!
Questions? Call us: (475) 244-9781
Oronoque Village 638A ONONDAGA LN, STRATFORD, CT, 06614, Stratford, CT 06614
$499,900

1 beds

|

3 baths

|

1,175 sq ft

|

Condo

638A ONONDAGA LN, STRATFORD, CT, 06614
Community: Oronoque Village
Jefferson Village 51 JEFFERSON OVAL F, YORKTOWN, NY, 10598, Yorktown, NY 10598
$419,000

2 beds

|

2 baths

|

1,100 sq ft

|

Condo

51 JEFFERSON OVAL F, YORKTOWN, NY, 10598
Community: Jefferson Village
Heritage Village 930 HERITAGE VLG B, SOUTHBURY, CT, 06488, Southbury, CT 06488
$419,900

2 beds

|

2 baths

|

1,398 sq ft

|

Condo

930 HERITAGE VLG B, SOUTHBURY, CT, 06488
Community: Heritage Village
The Waterways at Moriches 548 HIGHLAND CT, BROOKHAVEN, NY, 11955, Brookhaven, NY 11955
$479,000

2 beds

|

2 baths

|

1,771 sq ft

|

Condo

548 HIGHLAND CT, BROOKHAVEN, NY, 11955
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.
Heritage Village 405 HERITAGE VLG D, SOUTHBURY, CT, 06488, Southbury, CT 06488
$159,999

2 beds

|

2 baths

|

1,044 sq ft

|

Condo

405 HERITAGE VLG D, SOUTHBURY, CT, 06488
Community: Heritage Village
Leisure Village 274 BERWICK CT A, BROOKHAVEN, NY, 11961, Brookhaven, NY 11961
$349,999

2 beds

|

1 baths

|

836 sq ft

|

Condo

274 BERWICK CT A, BROOKHAVEN, NY, 11961
Community: Leisure Village
The Waterways at Moriches 414 LINDSAY LN, BROOKHAVEN, NY, 11955, Brookhaven, NY 11955
$485,000

2 beds

|

2 baths

|

2,141 sq ft

|

Condo

414 LINDSAY LN, BROOKHAVEN, NY, 11955
Heritage Village 73 HERITAGE VLG C, SOUTHBURY, CT, 06488, Southbury, CT 06488
$199,900

2 beds

|

2 baths

|

1,044 sq ft

|

Condo

73 HERITAGE VLG C, SOUTHBURY, CT, 06488
Community: Heritage Village
Glenwood Village 1661 OLD COUNTRY RD 308, RIVERHEAD, NY, ..., Riverhead, NY 11901
$99,000

2 beds

|

1 baths

|

840 sq ft

|

Mobile Home

1661 OLD COUNTRY RD 308, RIVERHEAD, NY, ...
Community: Glenwood Village

Frequently Asked Questions


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