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

290 homes near Cheshire

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Castle Heights of Cheshir...

$500Ks - $600Ks

Castle Heights of Cheshir..., Cheshire, CT

Resale Only | 55+ age-restricted | Built 2007 - 2022 | 88 homes

3 rating (2 reviews)

Heritage Hills

$300Ks - $900Ks

Heritage Hills, Somers, NY

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

3.6 rating (7 reviews)

Heritage Village

$100Ks - $400Ks

Heritage Village, Southbury, CT

Resale Only | 55+ age-restricted | Built 1967 - 2005 | 2,580 homes

No reviews yet

Leisure Village

$200Ks - $500Ks

Leisure Village, Ridge, NY

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

No reviews yet

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

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

Questions? Call us: (475) 244-9781

No reviews yet

Rivington

$500Ks - $900Ks

Rivington, Danbury, CT

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

4 rating (1 reviews)

Jefferson Village

$200Ks - $500Ks

Jefferson Village, Yorktown Heights, NY

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

No reviews yet

Oronoque Village

$300Ks - $600Ks

Oronoque Village, Stratford, CT

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

No reviews yet

The Village at Oxford Gre...

$500Ks - $700Ks

The Village at Oxford Gre..., Oxford, CT

New and Resale | 55+ age-restricted | Built 2004 - present | 835 homes

No reviews yet

Meadowbrook Pointe Athlet...

$1Ms - $1Ms

Meadowbrook Pointe Athlet..., Westbury, NY

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

No reviews yet

Leisure Knoll

$200Ks - $400Ks

Leisure Knoll, Ridge, NY

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

No reviews yet

Country Pointe Plainview

$1Ms - $1Ms

Country Pointe Plainview, Plainview, NY

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

5 rating (1 reviews)

Fairfield at St. James

$400Ks - $500Ks

Fairfield at St. James, St. James, NY

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

No reviews yet

Leisure Glen

$400Ks - $500Ks

Leisure Glen, Ridge, NY

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

No reviews yet

Spring Lake Village

$200Ks - $200Ks

Spring Lake Village, Southington, CT

Resale Only | 55+ age-restricted | Built 1970 - 2004 | 640 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 - $400Ks

Glenwood Village, Riverhead, NY

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

3.7 rating (3 reviews)

Greenwood Village

$100Ks - $200Ks

Greenwood Village, Manorville, NY

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

No reviews yet

The Seasons at East Meado...

$500Ks - $600Ks

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

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

No reviews yet

Regency at Prospect

$400Ks - $400Ks

Regency at Prospect, Prospect, CT

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

No reviews yet

Dutchgate

$400Ks - $500Ks

Dutchgate, Valley Stream, NY

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

No reviews yet

The Waterways at Moriches

$400Ks - $600Ks

The Waterways at Moriches, Moriches, NY

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

No reviews yet

The Retreat at Carmel

$400Ks - $600Ks

The Retreat at Carmel, Carmel, NY

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

3.5 rating (2 reviews)

Foxwood Village

$300Ks - $400Ks

Foxwood Village, Calverton, NY

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

1 rating (1 reviews)

Plymouth Estates at Mount...

$500Ks - $500Ks

Plymouth Estates at Mount..., Mount Sinai, NY

Resale Only | 55+ age-restricted | Built 2006 - 2013 | 285 homes

4 rating (1 reviews)

Vineyards at Blue Point

$800Ks - $800Ks

Vineyards at Blue Point, Blue Point, NY

Resale Only | 55+ age-restricted | Built 2016 - 2018 | 280 homes

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

Questions? Call us: (475) 244-9781

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

No reviews yet

HarborView

$900Ks - $1Ms

HarborView, Port Washington, NY

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

No reviews yet

The Club at Melville

$500Ks - $500Ks

The Club at Melville, Melville, NY

Resale Only | 55+ age-restricted | Built 2015 - 2017 | 261 homes

No reviews yet

The Seasons at Elwood

$800Ks - $900Ks

The Seasons at Elwood, East Northport, NY

Resale Only | 55+ age-restricted | Built 2018 - 2020 | 256 homes

No reviews yet

Meadow Brook Estates

$500Ks - $500Ks

Meadow Brook Estates, Oxford, CT

Resale Only | 55+ age-restricted | Built 2003 - 2020 | 246 homes

5 rating (1 reviews)

Encore Atlantic Shores

$600Ks - $700Ks

Encore Atlantic Shores, Eastport, NY

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

No reviews yet

The Summit at Bethel

$600Ks - $600Ks

The Summit at Bethel, Bethel, CT

Resale Only | 55+ age-restricted | Built 2010 - 2021 | 235 homes

4.9 rating (14 reviews)

Chatfield Farms

$500Ks - $500Ks

Chatfield Farms, Beacon Falls, CT

New Construction | 55+ age-restricted | Built 2014 - present | 231 homes

5 rating (1 reviews)

Encore at Lake Grove

$500Ks - $600Ks

Encore at Lake Grove, Lake Grove, NY

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

No reviews yet

Woodridge Strathmore Terr...

$400Ks - $400Ks

Woodridge Strathmore Terr..., Mount Sinai, NY

Resale Only | 55+ age-restricted | Built 1974 - 1985 | 226 homes

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

Questions? Call us: (475) 244-9781

5 rating (1 reviews)

Sunrise Village

$400Ks - $400Ks

Sunrise Village, Sayville, NY

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

No reviews yet

Saddle Lakes

$400Ks - $400Ks

Saddle Lakes, Riverhead, NY

Resale Only | 55+ age-restricted | Built 2000 - 2002 | 196 homes

No reviews yet

Country Village Estates

$400Ks - $500Ks

Country Village Estates, Coram, NY

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

5 rating (1 reviews)

Sunken Pond Estates

$400Ks - $500Ks

Sunken Pond Estates, Riverhead, NY

Resale Only | 55+ age-restricted | Built 2003 - 2005 | 194 homes

5 rating (1 reviews)

Westhampton Pines

$900Ks - $1Ms

Westhampton Pines, Westhampton, NY

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

1082 SAVOY DR, MELVILLE, NY, 11747

Condo

56 THEODORE DR, CORAM, NY, 11727

Community: Country Village Estates

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

Questions? Call us: (475) 244-9781

The Greens at Half Hollow

285 MADEIRA BLVD # 285, MELVILLE, NY, 11..., Melville, NY 11747

$1,555,500

3 beds

3 baths

3,200 sq ft

Condo

285 MADEIRA BLVD # 285, MELVILLE, NY, 11...

Community: The Greens at Half Hollow

Encore Atlantic Shores

48 ENCORE BLVD, EASTPORT, NY, 11941, Eastport, NY 11941

$725,000

2 beds

2 baths

2,100 sq ft

Condo

48 ENCORE BLVD, EASTPORT, NY, 11941

Community: Encore Atlantic Shores

Sunrise Village

133 REVERE DR, SAYVILLE, NY, 11782, Sayville, NY 11782

$429,000

2 beds

1 baths

1,000 sq ft

Condo

133 REVERE DR, SAYVILLE, NY, 11782

Community: Sunrise Village

Leisure Knoll

28 KINGSTON DR, RIDGE, NY, 11961, Ridge, NY 11961

$450,000

2 beds

2 baths

1,094 sq ft

Condo

28 KINGSTON DR, RIDGE, NY, 11961

Community: Leisure Knoll

The Greens at Half Hollow

262 ALTESSA BLVD # 262, MELVILLE, NY, 11..., Melville, NY 11747

$1,349,999

3 beds

4 baths

3,200 sq ft

Condo

262 ALTESSA BLVD # 262, MELVILLE, NY, 11...

Community: The Greens at Half Hollow

Strathmore Gate East

46 FREEDOM LN, CORAM, NY, 11727, Coram, NY 11727

$390,000

2 beds

2 baths

1,112 sq ft

Condo

46 FREEDOM LN, CORAM, NY, 11727

Community: Strathmore Gate East

Leisure Village

311 WOODBRIDGE DR 311-C, RIDGE, NY, 1196..., Ridge, NY 11961

$245,000

1 beds

1 baths

684 sq ft

Condo

311 WOODBRIDGE DR 311-C, RIDGE, NY, 1196...

Community: Leisure Village

Heritage Hills

972 C HERITAGE HLS Y., SOMERS, NY, 10589, Somers, NY 10589

$590,000

2 beds

2 baths

1,468 sq ft

Condo

972 C HERITAGE HLS Y., SOMERS, NY, 10589

Community: Heritage Hills

Eagles Walk at East Quogue

1601 AERIE WAY, EAST QUOGUE, NY, 11942, East Quogue, NY 11942

$535,000

2 beds

2 baths

1,275 sq ft

Condo

1601 AERIE WAY, EAST QUOGUE, NY, 11942

Community: Eagles Walk at East Quogue

Leisure Knoll

215 KINGSTON DR, RIDGE, NY, 11961, Ridge, NY 11961

$454,990

2 beds

2 baths

1,116 sq ft

Condo

215 KINGSTON DR, RIDGE, NY, 11961

Community: Leisure Knoll

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

Questions? Call us: (475) 244-9781

Leisure Knoll

503 LANCASTER CT # 503, RIDGE, NY, 11961, Ridge, NY 11961

$469,000

2 beds

2 baths

1,094 sq ft

Condo

503 LANCASTER CT # 503, RIDGE, NY, 11961

Community: Leisure Knoll

Leisure Village

259 NEWCASTLE CT E, RIDGE, NY, 11961, Ridge, NY 11961

$259,900

1 beds

1 baths

875 sq ft

Condo

259 NEWCASTLE CT E, RIDGE, NY, 11961

Community: Leisure Village

Jefferson Village

108 VILLAGE RD B, YORKTOWN HEIGHTS, NY, ..., Yorktown Heights, NY 10598

$469,900

2 beds

2 baths

1,200 sq ft

Condo

108 VILLAGE RD B, YORKTOWN HEIGHTS, NY, ...

Community: Jefferson Village

Leisure Village

419 WEYMOUTH CT UNIT F F, RIDGE, NY, 119..., Ridge, NY 11961

$260,000

1 beds

1 baths

782 sq ft

Condo

419 WEYMOUTH CT UNIT F F, RIDGE, NY, 119...

Community: Leisure Village

Leisure Village

49 TRENT CT B, RIDGE, NY, 11961, Ridge, NY 11961

$319,000

2 beds

1 baths

1,100 sq ft

Condo

49 TRENT CT B, RIDGE, NY, 11961

Community: Leisure Village

Vineyards at Blue Point

26 AVERY WAY, BLUE POINT, NY, 11772, Blue Point, NY 11772

$899,000

2 beds

4 baths

3,388 sq ft

Condo

26 AVERY WAY, BLUE POINT, NY, 11772

Community: Vineyards at Blue Point

Greenwood Village

132 VILLAGE CIR, MANORVILLE, NY, 11949, Manorville, NY 11949

$199,990

2 beds

2 baths

1,375 sq ft

Condo

132 VILLAGE CIR, MANORVILLE, NY, 11949

Community: Greenwood Village

The Greens at Half Hollow

679 BALFOUR PL, MELVILLE, NY, 11747, Melville, NY 11747

$1,399,999

3 beds

3 baths

2,500 sq ft

Condo

679 BALFOUR PL, MELVILLE, NY, 11747

Community: The Greens at Half Hollow

The Greens at Half Hollow

1000 N MADEIRA BLVD, HUNTINGTON, NY, 117..., Huntington, NY 11797

$649,999

2 beds

2 baths

1,183 sq ft

Condo

1000 N MADEIRA BLVD, HUNTINGTON, NY, 117...

Community: The Greens at Half Hollow

Leisure Village

166 VENTRY CT B, RIDGE, NY, 11961, Ridge, NY 11961

$259,000

1 beds

1 baths

680 sq ft

House

166 VENTRY CT B, RIDGE, NY, 11961

Condo

280 BERWICK CT B, RIDGE, NY, 11961

Community: Leisure Village

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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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290 homes near Cheshire

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

125 communities near Cheshire

290 homes near Cheshire

2 beds

1 baths

1,000 sq ft

Condo

2 beds

2 baths

1,258 sq ft

Condo

2 beds

1 baths

1,000 sq ft

Mobile Home

2 beds

2 baths

1,152 sq ft

Mobile Home

2 beds

2 baths

1,114 sq ft

Condo

2 beds

2 baths

1,120 sq ft

Condo

2 beds

2 baths

1,200 sq ft

Condo

2 beds

2 baths

941 sq ft

Condo

2 beds

2 baths

2,054 sq ft

Condo

2 beds

2 baths

1,605 sq ft

Condo

2 beds

3 baths

2,290 sq ft

Condo

2 beds

1 baths

875 sq ft

Condo

1 beds

1 baths

967 sq ft

Condo

2 beds

2 baths

1,393 sq ft

Condo

2 beds

2 baths

1,198 sq ft

Condo

3 beds

3 baths

3,200 sq ft

Condo

2 beds

2 baths

2,100 sq ft

Condo

2 beds

1 baths

1,000 sq ft

Condo

2 beds

2 baths

1,094 sq ft

Condo

3 beds