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Cheshire, CT 55+ active adult communities & homes for sale - Page 6

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
Glenwood Village 1661 OLD COUNTRY RD 454, RIVERHEAD, NY, ..., Riverhead, NY 11901
$310,000

2 beds

|

2 baths

|

1,152 sq ft

|

Manufactured Home

1661 OLD COUNTRY RD 454, RIVERHEAD, NY, ...
Community: Glenwood Village
Encore Atlantic Shores 140 CHOPIN PL, BROOKHAVEN, NY, 11941, Brookhaven, NY 11941
$849,900

2 beds

|

3 baths

|

2,236 sq ft

|

Condo

140 CHOPIN PL, BROOKHAVEN, NY, 11941
The Village at Oxford Greens 171 COUNTRY CLUB DR 171, OXFORD, CT, 064..., Oxford, CT 06478
$715,000

3 beds

|

3 baths

|

2,750 sq ft

|

Condo

171 COUNTRY CLUB DR 171, OXFORD, CT, 064...
Oronoque Village 621 ONONDAGA LN B, STRATFORD, CT, 06614, Stratford, CT 06614
$499,000

1 beds

|

3 baths

|

2,325 sq ft

|

Condo

621 ONONDAGA LN B, STRATFORD, CT, 06614
Community: Oronoque Village
Westhampton Pines 79 SAMANTHA CIR, SOUTHAMPTON, NY, 11977, Southampton, NY 11977
$1,295,000

2 beds

|

3 baths

|

2,440 sq ft

|

Condo

79 SAMANTHA CIR, SOUTHAMPTON, NY, 11977
Community: Westhampton Pines
Want to learn more about 55+ communities in Cheshire? 55places can help!
Questions? Call us: (475) 244-9781
Heritage Hills 88 HERITAGE HLS B, SOMERS, NY, 10589, Somers, NY 10589
$670,000

2 beds

|

3 baths

|

1,585 sq ft

|

Condo

88 HERITAGE HLS B, SOMERS, NY, 10589
Community: Heritage Hills
Hopmeadow Place 1 W ST 215, SIMSBURY, CT, 06070, Simsbury, CT 06070
$385,000

2 beds

|

2 baths

|

1,477 sq ft

|

Condo

1 W ST 215, SIMSBURY, CT, 06070
Community: Hopmeadow Place
Jefferson Village 34 WARWICK PL B, YORKTOWN, NY, 10598, Yorktown, NY 10598
$359,000

2 beds

|

2 baths

|

1,000 sq ft

|

Condo

34 WARWICK PL B, YORKTOWN, NY, 10598
Community: Jefferson Village
Heritage Village 643 HERITAGE VLG A, SOUTHBURY, CT, 06488, Southbury, CT 06488
$374,500

2 beds

|

2 baths

|

1,398 sq ft

|

Condo

643 HERITAGE VLG A, SOUTHBURY, CT, 06488
Community: Heritage Village
Jefferson Village 20 HASTINGS CT A, YORKTOWN, NY, 10598, Yorktown, NY 10598
$330,000

1 beds

|

1 baths

|

800 sq ft

|

Condo

20 HASTINGS CT A, YORKTOWN, NY, 10598
Community: Jefferson Village
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.
Greenwood Village 28 GREENWOOD BLVD, BROOKHAVEN, NY, 11949, Brookhaven, NY 11949
$149,999

2 beds

|

2 baths

|

938 sq ft

|

Condo

28 GREENWOOD BLVD, BROOKHAVEN, NY, 11949
Community: Greenwood Village
Rivington 215 CENTER MEADOW LN 215, DANBURY, CT, 0..., Danbury, CT 06810
$485,000

2 beds

|

2 baths

|

1,258 sq ft

|

Condo

215 CENTER MEADOW LN 215, DANBURY, CT, 0...
Community: Rivington
The Waterways at Moriches 416 LINDSAY LN, BROOKHAVEN, NY, 11955, Brookhaven, NY 11955
$575,000

2 beds

|

2 baths

|

1,440 sq ft

|

Condo

416 LINDSAY LN, BROOKHAVEN, NY, 11955
Leisure Knoll 7 AVON CT, BROOKHAVEN, NY, 11961, Brookhaven, NY 11961
$469,999

2 beds

|

2 baths

|

1,070 sq ft

|

Condo

7 AVON CT, BROOKHAVEN, NY, 11961
Community: Leisure Knoll
Regency at Woodbridge 27 HERITAGE LN, WOODBRIDGE, CT, 06525, Woodbridge, CT 06525
$599,900

3 beds

|

3 baths

|

2,006 sq ft

|

Condo

27 HERITAGE LN, WOODBRIDGE, CT, 06525
Fairfield at St. James 708 W CABOT CT 708, SMITHTOWN, NY, 11780, Smithtown, NY 11780
$499,998

1 beds

|

1 baths

|

886 sq ft

|

Condo

708 W CABOT CT 708, SMITHTOWN, NY, 11780
Want to learn more about 55+ communities in Cheshire? 55places can help!
Questions? Call us: (475) 244-9781
Heritage Hills 813 HERITAGE HLS, SOMERS, NY, 10589, Somers, NY 10589
$815,000

2 beds

|

2 baths

|

1,663 sq ft

|

Condo

813 HERITAGE HLS, SOMERS, NY, 10589
Community: Heritage Hills
Glenwood Village 1661 OLD COUNTRY RD 377, RIVERHEAD, NY, ..., Riverhead, NY 11901
$375,000

3 beds

|

2 baths

|

1,317 sq ft

|

Manufactured Home

1661 OLD COUNTRY RD 377, RIVERHEAD, NY, ...
Community: Glenwood Village
Heritage Village 345 HERITAGE VLG A, SOUTHBURY, CT, 06488, Southbury, CT 06488
$370,000

3 beds

|

2 baths

|

1,716 sq ft

|

Condo

345 HERITAGE VLG A, SOUTHBURY, CT, 06488
Community: Heritage Village
Leisure Village 232 BLACKPOOL CT F, BROOKHAVEN, NY, 1196..., Brookhaven, NY 11961
$329,000

2 beds

|

1 baths

|

875 sq ft

|

Condo

232 BLACKPOOL CT F, BROOKHAVEN, NY, 1196...
Community: Leisure Village
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.
Vineyards at Brookfield 61 AVERY DR, BROOKHAVEN, NY, 11934, Brookhaven, NY 11934
$674,999

2 beds

|

2 baths

|

1,557 sq ft

|

Condo

61 AVERY DR, BROOKHAVEN, NY, 11934
Greenwood Village 69 DOGWOOD LN, BROOKHAVEN, NY, 11949, Brookhaven, NY 11949
$139,000

2 beds

|

2 baths

|

1,134 sq ft

|

Condo

69 DOGWOOD LN, BROOKHAVEN, NY, 11949
Community: Greenwood Village
Encore Atlantic Shores 228 SONATA CT, BROOKHAVEN, NY, 11941, Brookhaven, NY 11941
$749,000

2 beds

|

2 baths

|

1,605 sq ft

|

Condo

228 SONATA CT, BROOKHAVEN, NY, 11941
Liberty at Newtown 16 FRANKLIN CT 16, NEWTOWN, CT, 06470, Newtown, CT 06470
$599,000

2 beds

|

3 baths

|

1,940 sq ft

|

Condo

16 FRANKLIN CT 16, NEWTOWN, CT, 06470
Community: Liberty at Newtown
The Villas at Narragansett 406 NARRAGANSETT VILLAS DR, BABYLON, NY,..., Babylon, NY 11757
$529,000

2 beds

|

2 baths

|

1,215 sq ft

|

Condo

406 NARRAGANSETT VILLAS DR, BABYLON, NY,...
The Village at Oxford Greens 1129 ST ANDREWS DR 49, OXFORD, CT, 06478, Oxford, CT 06478
$709,555

2 beds

|

3 baths

|

2,454 sq ft

|

Condo

1129 ST ANDREWS DR 49, OXFORD, CT, 06478
Fairview at Oxford Greens 1129 ST ANDREWS DR 49, OXFORD, CT, 06478, Oxford, CT 06478
$709,555

2 beds

|

3 baths

|

2,454 sq ft

|

Condo

1129 ST ANDREWS DR 49, OXFORD, CT, 06478
Want to learn more about 55+ communities in Cheshire? 55places can help!
Questions? Call us: (475) 244-9781
Fairview at Oxford Greens 1111 ST ANDREWS DR 16, OXFORD, CT, 06478, Oxford, CT 06478
$778,585

2 beds

|

3 baths

|

2,454 sq ft

|

Condo

1111 ST ANDREWS DR 16, OXFORD, CT, 06478
The Village at Oxford Greens 1111 ST ANDREWS DR 16, OXFORD, CT, 06478, Oxford, CT 06478
$778,585

2 beds

|

3 baths

|

2,454 sq ft

|

Condo

1111 ST ANDREWS DR 16, OXFORD, CT, 06478
The Village at Oxford Greens 1138 ST ANDREWS DR 90, OXFORD, CT, 06478, Oxford, CT 06478
$754,150

2 beds

|

3 baths

|

1,955 sq ft

|

Condo

1138 ST ANDREWS DR 90, OXFORD, CT, 06478
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 1138 ST ANDREWS DR 90, OXFORD, CT, 06478, Oxford, CT 06478
$754,150

2 beds

|

3 baths

|

1,955 sq ft

|

Condo

1138 ST ANDREWS DR 90, OXFORD, CT, 06478
Encore Atlantic Shores 63 ENCORE BLVD, BROOKHAVEN, NY, 11941, Brookhaven, NY 11941
$895,000

2 beds

|

3 baths

|

2,769 sq ft

|

Condo

63 ENCORE BLVD, BROOKHAVEN, NY, 11941
Jefferson Village 90 MOLLY PITCHER LN F, YORKTOWN, NY, 105..., Yorktown, NY 10598
$309,999

1 beds

|

1 baths

|

800 sq ft

|

Condo

90 MOLLY PITCHER LN F, YORKTOWN, NY, 105...
Community: Jefferson Village
Eagles Walk at East Quogue 1204 AERIE WAY 1204, SOUTHAMPTON, NY, 11..., Southampton, NY 11942
$565,000

2 beds

|

2 baths

|

1,341 sq ft

|

Condo

1204 AERIE WAY 1204, SOUTHAMPTON, NY, 11...
Encore Atlantic Shores 216 SONATA CT, BROOKHAVEN, NY, 11941, Brookhaven, NY 11941
$889,000

2 beds

|

3 baths

|

2,439 sq ft

|

Condo

216 SONATA CT, BROOKHAVEN, NY, 11941
The Waterways at Moriches 132 CAPTAINS CT, BROOKHAVEN, NY, 11955, Brookhaven, NY 11955
$550,000

2 beds

|

2 baths

|

1,544 sq ft

|

Condo

132 CAPTAINS CT, BROOKHAVEN, NY, 11955
Newtown Woods 23 WOODS LN 23, NEWTOWN, CT, 06470, Newtown, CT 06470
$575,000

2 beds

|

3 baths

|

2,073 sq ft

|

Condo

23 WOODS LN 23, NEWTOWN, CT, 06470
Community: Newtown Woods
HarborView 123 LINKS CT, NORTH HEMPSTEAD, NY, 11050, North Hempstead, NY 11050
$1,249,000

3 beds

|

3 baths

|

2,160 sq ft

|

Condo

123 LINKS CT, NORTH HEMPSTEAD, NY, 11050
Community: HarborView
Want to learn more about 55+ communities in Cheshire? 55places can help!
Questions? Call us: (475) 244-9781
Heritage Village 581 HERITAGE VLG A, SOUTHBURY, CT, 06488, Southbury, CT 06488
$342,500

2 beds

|

2 baths

|

1,398 sq ft

|

Condo

581 HERITAGE VLG A, SOUTHBURY, CT, 06488
Community: Heritage Village
Heritage Village 895 HERITAGE VLG A, SOUTHBURY, CT, 06488, Southbury, CT 06488
$339,900

2 beds

|

2 baths

|

1,398 sq ft

|

Condo

895 HERITAGE VLG A, SOUTHBURY, CT, 06488
Community: Heritage Village
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.
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