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

131 communities 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

Oronoque Village

$200ks - $400ks

Oronoque Village, Stratford, CT

Resale Only | 55+ age-restricted | Built 1971 - 1977 | 929 homes

3 rating (2 reviews)

Heritage Hills

$400ks - $800ks

Heritage Hills, Somers, NY

Resale Only | Age-targeted | Built 1974 - 2006 | 2,600 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

4 rating (1 reviews)

Jefferson Village

$100ks - $500ks

Jefferson Village, Yorktown Heights, NY

Resale Only | 55+ age-restricted | Built 1967 - 1982 | 1,000 homes

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

Questions? Call us: (475) 244-9781

The Waterways at Moriches

$300ks - $600ks

The Waterways at Moriches, Moriches, NY

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

Overlook

$600ks - $900ks

Overlook, Carmel, NY

New Construction | 55+ age-restricted | 300 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

Country Pointe Plainview

$700ks - $1Ms

Country Pointe Plainview, Plainview, NY

New Construction | 55+ age-restricted | Built 2017 - present | 660 homes

3.7 rating (3 reviews)

Greenwood Village

$100ks

Greenwood Village, Manorville, NY

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

Fairview at Oxford Greens

$400ks - $600ks

Fairview at Oxford Greens, Oxford, CT

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

4 rating (8 reviews)

Glenwood Village

$100ks - $200ks

Glenwood Village, Riverhead, NY

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

Leisure Village

$100ks - $300ks

Leisure Village, Ridge, NY

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

5 rating (1 reviews)

Encore Atlantic Shores

$500ks - $800ks

Encore Atlantic Shores, Eastport, NY

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

Dutchgate

$300ks - $500ks

Dutchgate, Valley Stream, NY

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

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

Questions? Call us: (475) 244-9781

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 Gardens of Wilbraham

$200ks - $400ks

The Gardens of Wilbraham, Wilbraham, MA

New and Resale | 55+ age-restricted | Built 2005 - present | 108 homes

5 rating (1 reviews)

Newtown Woods

$300ks - $500ks

Newtown Woods, Newtown, CT

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

Stoneleigh Woods at River...

$500ks

Stoneleigh Woods at River..., Riverhead, NY

Resale Only | 55+ age-restricted | Built 2007 - 2016 | 176 homes

Liberty at Newtown

$300ks - $400ks

Liberty at Newtown, Newtown, CT

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

Leisure Glen

$300ks - $400ks

Leisure Glen, Ridge, NY

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

HarborView

$800ks - $1Ms

HarborView, Port Washington, NY

Resale Only | 55+ age-restricted | Built 2002 - 2004 | 270 homes

Country Pointe Preserve

$600ks - $900ks

Country Pointe PreserveYaphank, NY

New Construction | 55+ age-restricted | Built 2024 - present | 152 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)

Westhampton Pines

$900ks - $1Ms

Westhampton Pines, Westhampton, NY

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

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Questions? Call us: (475) 244-9781

5 rating (1 reviews)

The Villages at Mount Sin...

$600ks

The Villages at Mount Sin..., Mount Sinai, NY

Resale Only | 55+ age-restricted | Built 2005 - 2007 | 185 homes

Baldwin Station

$400ks

Baldwin Station, Milford, CT

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

Village Estates

$300ks - $400ks

Village Estates, Amityville, NY

Resale Only | 55+ age-restricted | Built 2006 - 2008 | 138 homes

Leisure Knoll

$200ks - $400ks

Leisure Knoll, Ridge, NY

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

Vineyards at Moriches

$500ks - $600ks

Vineyards at Moriches, Center Moriches, NY

Resale Only | 55+ age-restricted | Built 2008 - 2014 | 92 homes

3.5 rating (2 reviews)

Foxwood Village

$200ks - $400ks

Foxwood Village, Calverton, NY

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

5 rating (1 reviews)

Sunrise Village

$400ks

Sunrise Village, Sayville, NY

Resale Only | 55+ age-restricted | Built 1985 - 1990 | 213 homes

Applegate Estates

$500ks - $400ks

Applegate Estates, Southington, CT

New and Resale | 55+ age-restricted | Built 2010 - 2025 | 94 homes

Strathmore Gate East

$300ks

Strathmore Gate East, Coram, NY

Resale Only | 55+ age-restricted | Built 1970 - 1975 | 174 homes

Billingsgate

$400ks - $600ks

Billingsgate, Simsbury, CT

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

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

Questions? Call us: (475) 244-9781

The Powder Forest Homes

$500ks - $700ks

The Powder Forest Homes, Simsbury, CT

Resale Only | 55+ age-restricted | Built 2006 - 2016 | 182 homes

Country Village Estates

$300ks

Country Village Estates, Coram, NY

Resale Only | 55+ age-restricted | Built 1993 - 2001 | 195 homes

1 2 3...4

Greenwood Village

105 W VILLAGE CIR 105, BROOKHAVEN, NY, 1..., Brookhaven, NY 11949

$245,000

2 beds

2 baths

1,130 sq ft

Condo

105 W VILLAGE CIR 105, BROOKHAVEN, NY, 1...

Community: Greenwood Village

Glenwood Village

1661 OLD COUNTRY RD 516, RIVERHEAD, NY, ..., Riverhead, NY 11901

$419,000

2 beds

2 baths

1,624 sq ft

Manufactured Home

1661 OLD COUNTRY RD 516, RIVERHEAD, NY, ...

Community: Glenwood Village

New Fairview at Oxford Greens

1129 ST ANDREWS DR 49, OXFORD, CT, 06478, Oxford, CT 06478

$663,775

2 beds

3 baths

2,454 sq ft

Condo

1129 ST ANDREWS DR 49, OXFORD, CT, 06478

Community: Fairview at Oxford Greens

New The Village at Oxford Greens

$663,775

2 beds

3 baths

2,454 sq ft

Condo

1129 ST ANDREWS DR 49, OXFORD, CT, 06478

Community: The Village at Oxford Greens

New Fairview at Oxford Greens

1111 ST ANDREWS DR 16, OXFORD, CT, 06478, Oxford, CT 06478

$778,160

2 beds

3 baths

2,454 sq ft

Condo

1111 ST ANDREWS DR 16, OXFORD, CT, 06478

Community: Fairview at Oxford Greens

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

Questions? Call us: (475) 244-9781

New The Village at Oxford Greens

$778,160

2 beds

3 baths

2,454 sq ft

Condo

1111 ST ANDREWS DR 16, OXFORD, CT, 06478

Community: The Village at Oxford Greens

New 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

Community: Village Estates

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Questions? Call us: (475) 244-9781

New Jefferson Village

90 MOLLY PITCHER LN F, YORKTOWN, NY, 105..., Yorktown, NY 10598

$359,900

1 beds

1 baths

800 sq ft

Condo

90 MOLLY PITCHER LN F, YORKTOWN, NY, 105...

Community: Jefferson Village

New 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...

Community: Eagles Walk at East Quogue

New Woodridge Strathmore Terrace

89 STANDISH DR, BROOKHAVEN, NY, 11766, Brookhaven, NY 11766

$500,000

2 beds

2 baths

1,240 sq ft

House

89 STANDISH DR, BROOKHAVEN, NY, 11766

Community: Woodridge Strathmore Terrace

New Jefferson Village

149 FLINTLOCK WAY E, YORKTOWN, NY, 10598, Yorktown, NY 10598

$375,000

1 beds

1 baths

853 sq ft

Condo

149 FLINTLOCK WAY E, YORKTOWN, NY, 10598

Community: Jefferson Village

New Leisure Village

231 BLACKPOOL CT, BROOKHAVEN, NY, 11961, Brookhaven, NY 11961

$299,000

2 beds

1 baths

836 sq ft

Condo

231 BLACKPOOL CT, BROOKHAVEN, NY, 11961

Community: Leisure Village

New The Greens at Half Hollow

742 VERONA DR, HUNTINGTON, NY, 11747, Huntington, NY 11747

$1,099,000

2 beds

3 baths

1,940 sq ft

Condo

742 VERONA DR, HUNTINGTON, NY, 11747

Community: The Greens at Half Hollow

New Dutchgate

301 WILLOW LN, HEMPSTEAD, NY, 11580, Hempstead, NY 11580

$510,000

2 beds

2 baths

941 sq ft

Condo

301 WILLOW LN, HEMPSTEAD, NY, 11580

Community: Dutchgate

New Overlook

4095 FAIRWAYS DR 148, CARMEL, NY, 10512, Carmel, NY 10512

$699,000

3 beds

3 baths

1,914 sq ft

Condo

4095 FAIRWAYS DR 148, CARMEL, NY, 10512

Community: Overlook

New Heritage Hills

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

$499,900

2 beds

2 baths

1,138 sq ft

Condo

241 HERITAGE HLS D, SOMERS, NY, 10589

Community: Heritage Hills

Country Pointe Plainview

52102 BEECH TREE LN, OYSTER BAY, NY, 118..., Oyster Bay, NY 11803

$1,649,990

2 beds

3 baths

1,750 sq ft

Condo

52102 BEECH TREE LN, OYSTER BAY, NY, 118...

Community: Country Pointe Plainview

Encore Atlantic Shores

216 SONATA CT, BROOKHAVEN, NY, 11941, Brookhaven, NY 11941

$899,000

2 beds

3 baths

2,439 sq ft

Condo

216 SONATA CT, BROOKHAVEN, NY, 11941

Community: Encore Atlantic Shores

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

Questions? Call us: (475) 244-9781

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

Community: The Waterways at Moriches

Vineyards at Blue Point

37 HALLEY DR 17, BROOKHAVEN, NY, 11772, Brookhaven, NY 11772

$660,000

2 beds

2 baths

1,220 sq ft

Condo

37 HALLEY DR 17, BROOKHAVEN, NY, 11772

Community: Vineyards at Blue Point

Newtown Woods

1227 BROOKSIDE CT 1227, NEWTOWN, CT, 064..., Newtown, CT 06470

$500,000

2 beds

2 baths

1,483 sq ft

Condo

1227 BROOKSIDE CT 1227, NEWTOWN, CT, 064...

Community: Newtown Woods

Newtown Woods

23 WOODS LN 23, NEWTOWN, CT, 06470, Newtown, CT 06470

$600,000

2 beds

3 baths

2,073 sq ft

Condo

23 WOODS LN 23, NEWTOWN, CT, 06470

Community: Newtown Woods

Greenwood Village

5127 VILLAGE CIR, BROOKHAVEN, NY, 11949, Brookhaven, NY 11949

$227,000

2 beds

2 baths

1,291 sq ft

Condo

5127 VILLAGE CIR, BROOKHAVEN, NY, 11949

Community: Greenwood Village

HarborView

$1,199,000

3 beds

3 baths

2,216 sq ft

Condo

100 HARBOR VIEW DR 335, NORTH HEMPSTEAD,...

Community: HarborView

HarborView

123 LINKS CT, NORTH HEMPSTEAD, NY, 11050, North Hempstead, NY 11050

$1,299,000

3 beds

3 baths

2,160 sq ft

Condo

123 LINKS CT, NORTH HEMPSTEAD, NY, 11050

Community: HarborView

Heritage Village

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

$350,000

2 beds

2 baths

1,398 sq ft

Condo

581 HERITAGE VLG A, SOUTHBURY, CT, 06488

Community: Heritage Village

Jefferson Village

56 KIRBY CLOSE B, YORKTOWN, NY, 10598, Yorktown, NY 10598

$489,500

2 beds

2 baths

970 sq ft

Condo

56 KIRBY CLOSE B, YORKTOWN, NY, 10598

Community: Jefferson Village

Heritage Hills

828 HERITAGE HLS B, SOMERS, NY, 10589, Somers, NY 10589

$650,000

2 beds

2 baths

1,296 sq ft

Condo

828 HERITAGE HLS B, SOMERS, NY, 10589

Community: Heritage Hills

Windcrest East

5 GREEN ASH ST, RIVERHEAD, NY, 11933, Riverhead, NY 11933

$775,000

3 beds

3 baths

2,449 sq ft

House

5 GREEN ASH ST, RIVERHEAD, NY, 11933

Community: Windcrest East

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

Questions? Call us: (475) 244-9781

Oronoque Village

212 AGAWAM DR B, STRATFORD, CT, 06614, Stratford, CT 06614

$319,000

1 beds

2 baths

1,426 sq ft

Condo

212 AGAWAM DR B, STRATFORD, CT, 06614

Community: Oronoque Village

Oronoque Village

383 SEQUOIA LN B, STRATFORD, CT, 06614, Stratford, CT 06614

$485,000

1 beds

3 baths

1,360 sq ft

Condo

383 SEQUOIA LN B, STRATFORD, CT, 06614

Community: Oronoque Village

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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131 communities

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

131 communities near Cheshire

280 homes near Cheshire

2 beds

2 baths

1,130 sq ft

Condo

2 beds

2 baths

1,624 sq ft

Manufactured Home

2 beds

3 baths

2,454 sq ft

Condo

2 beds

3 baths

2,454 sq ft

Condo

2 beds

3 baths

2,454 sq ft

Condo

2 beds

3 baths

2,454 sq ft

Condo

2 beds

3 baths

1,955 sq ft

Condo

2 beds

3 baths

1,955 sq ft

Condo

2 beds

2 baths

1,067 sq ft

Condo

2 beds

3 baths

2,625 sq ft

Condo

2 beds

2 baths

1,710 sq ft

Condo

2 beds

3 baths

2,820 sq ft

Condo

1 beds

2 baths

1,375 sq ft

Condo

2 beds

3 baths

2,769 sq ft

Condo

2 beds

2 baths

1,470 sq ft

Condo

2 beds

2 baths

1,243 sq ft

Condo

1 beds

1 baths

800 sq ft

Condo

2 beds

2 baths

1,341 sq ft

Condo

2 beds

2 baths

1,240 sq ft

House

1 beds