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

294 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

$200Ks - $500Ks

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

$400Ks - $500Ks

Rivington, Danbury, CT

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

4 rating (1 reviews)

Jefferson Village

$300Ks - $600Ks

Jefferson Village, Yorktown Heights, NY

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

No reviews yet

Oronoque Village

$200Ks - $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...

$800Ks - $1Ms

Meadowbrook Pointe Athlet..., Westbury, NY

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

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No reviews yet

Leisure Knoll

$300Ks - $500Ks

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 (2 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 - $400Ks

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

$300Ks - $500Ks

Regency at Prospect, Prospect, CT

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

No reviews yet

Dutchgate

$400Ks - $400Ks

Dutchgate, Valley Stream, NY

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

No reviews yet

The Waterways at Moriches

$400Ks - $700Ks

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

No reviews yet

Overlook

$600Ks - $900Ks

Overlook, Carmel, NY

New Construction | 55+ age-restricted | 300 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

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

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

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 - $900Ks

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

$600Ks - $600Ks

Chatfield Farms, Beacon Falls, CT

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

5 rating (1 reviews)

Encore at Lake Grove

$600Ks - $800Ks

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

No reviews yet

Woodridge Strathmore Terr...

$400Ks - $400Ks

Woodridge Strathmore Terr..., Mount Sinai, NY

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

5 rating (1 reviews)

Sunrise Village

$400Ks - $500Ks

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

$300Ks - $400Ks

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

593 HERITAGE HLS B, SOMERS, NY, 10589

Community: Heritage Hills

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

Questions? Call us: (475) 244-9781

Leisure Glen

244 GLEN DR, RIDGE, NY, 11961, Ridge, NY 11961

$499,000

2 beds

2 baths

1,456 sq ft

Condo

244 GLEN DR, RIDGE, NY, 11961

Community: Leisure Glen

Heritage Hills

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

$575,000

2 beds

2 baths

1,468 sq ft

Condo

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

Community: Heritage Hills

Meadowbrook Pointe Links & Spa

279 AUGUSTA DR, MEDFORD, NY, 11763, Medford, NY 11763

$319,298

2 beds

2 baths

1,133 sq ft

Condo

279 AUGUSTA DR, MEDFORD, NY, 11763

Community: Meadowbrook Pointe Links & Spa

Leisure Village

310 WOODBRIDGE DR UNIT C, RIDGE, NY, 119..., Ridge, NY 11961

$344,000

2 beds

1 baths

1,278 sq ft

Condo

310 WOODBRIDGE DR UNIT C, RIDGE, NY, 119...

Community: Leisure Village

Sunken Pond Estates

4006 SAINT ANDREWS AVE, RIVERHEAD, NY, 1..., Riverhead, NY 11901

$519,888

2 beds

2 baths

1,587 sq ft

Condo

4006 SAINT ANDREWS AVE, RIVERHEAD, NY, 1...

Community: Sunken Pond Estates

Westhampton Pines

112 ASHLEY DR, WESTHAMPTON, NY, 11977, Westhampton, NY 11977

$1,399,000

3 beds

3 baths

2,306 sq ft

Condo

112 ASHLEY DR, WESTHAMPTON, NY, 11977

Community: Westhampton Pines

Leisure Knoll

407 BELFAST LN, RIDGE, NY, 11961, Ridge, NY 11961

$514,990

2 beds

2 baths

100 sq ft

Condo

407 BELFAST LN, RIDGE, NY, 11961

Community: Leisure Knoll

Windmill Gate

18 DAWN DR, OAKDALE, NY, 11769, Oakdale, NY 11769

$639,999

2 beds

2 baths

1,175 sq ft

House

18 DAWN DR, OAKDALE, NY, 11769

Community: Windmill Gate

Glenwood Village

1661 OLD COUNTRY RD 308, RIVERHEAD, NY, ..., Riverhead, NY 11901

$149,000

2 beds

1 baths

840 sq ft

Mobile Home

1661 OLD COUNTRY RD 308, RIVERHEAD, NY, ...

Community: Glenwood Village

Dutchgate

802 WILLOW LN UPPR LEVEL, VALLEY STREAM,..., Valley Stream, NY 11580

$480,000

2 beds

2 baths

941 sq ft

Condo

802 WILLOW LN UPPR LEVEL, VALLEY STREAM,...

Community: Dutchgate

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

Questions? Call us: (475) 244-9781

The Waterways at Moriches

106 E MIDLAND POND CT # 1, MORICHES, NY,..., Moriches, NY 11955

$499,000

2 beds

2 baths

1,982 sq ft

Condo

106 E MIDLAND POND CT # 1, MORICHES, NY,...

Community: The Waterways at Moriches

Leisure Village

488A FAIRWAY CT # 488A, RIDGE, NY, 11961, Ridge, NY 11961

$449,000

2 beds

2 baths

1,180 sq ft

Condo

488A FAIRWAY CT # 488A, RIDGE, NY, 11961

Community: Leisure Village

Leisure Village

46 TRENT CT C, RIDGE, NY, 11961, Ridge, NY 11961

$365,000

2 beds

1 baths

1,085 sq ft

Condo

46 TRENT CT C, RIDGE, NY, 11961

Community: Leisure Village

Heritage Hills

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

$775,000

3 beds

2 baths

1,909 sq ft

Condo

774 HERITAGE HLS B, SOMERS, NY, 10589

Community: Heritage Hills

Jefferson Village

36 SUSSEX DR B, YORKTOWN HEIGHTS, NY, 10..., Yorktown Heights, NY 10598

$375,000

1 beds

1 baths

725 sq ft

Condo

36 SUSSEX DR B, YORKTOWN HEIGHTS, NY, 10...

Community: Jefferson Village

Leisure Village

247 NEWCASTLE CT A, RIDGE, NY, 11961, Ridge, NY 11961

$425,000

2 beds

2 baths

1,564 sq ft

Condo

247 NEWCASTLE CT A, RIDGE, NY, 11961

Community: Leisure Village

Leisure Village

231 BLACKPOOL CT F, RIDGE, NY, 11961, Ridge, NY 11961

$305,000

2 beds

1 baths

875 sq ft

Condo

231 BLACKPOOL CT F, RIDGE, NY, 11961

Community: Leisure Village

Jefferson Village

141 FLINTLOCK WAY B, YORKTOWN HEIGHTS, N..., Yorktown Heights, NY 10598

$699,000

2 beds

2 baths

1,555 sq ft

Condo

141 FLINTLOCK WAY B, YORKTOWN HEIGHTS, N...

Community: Jefferson Village

Jefferson Village

34 WARWICK PL D, YORKTOWN HEIGHTS, NY, 1..., Yorktown Heights, NY 10598

$389,900

2 beds

2 baths

970 sq ft

House

34 WARWICK PL D, YORKTOWN HEIGHTS, NY, 1...

Community: Jefferson Village

Greenwood Village

16 VILLAGE CIR, BROOKHAVEN, NY, 11949, Brookhaven, NY 11949

$179,899

2 beds

2 baths

1,200 sq ft

Manufactured Home

16 VILLAGE CIR, BROOKHAVEN, NY, 11949

Community: Greenwood Village

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

Questions? Call us: (475) 244-9781

The Vineyards at Miller Place

43 HALLEY LN, MILLER PLACE, NY, 11764, Miller Place, NY 11764

$659,000

2 beds

3 baths

1,350 sq ft

Condo

43 HALLEY LN, MILLER PLACE, NY, 11764

Community: The Vineyards at Miller Place

The Greens at Half Hollow

911 ALTESSA BLVD, MELVILLE, NY, 11747, Melville, NY 11747

$639,000

2 beds

2 baths

1,134 sq ft

Condo

911 ALTESSA BLVD, MELVILLE, NY, 11747

Community: The Greens at Half Hollow

The Greens at Half Hollow

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

$1,475,000

3 beds

3 baths

3,200 sq ft

Condo

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

Community: The Greens at Half Hollow

Leisure Village

405 WOODBRIDGE DR D, RIDGE, NY, 11961, Ridge, NY 11961

$290,000

2 beds

1 baths

874 sq ft

Condo

405 WOODBRIDGE DR D, RIDGE, NY, 11961

Community: Leisure Village

Stoneleigh Woods at Riverhead

67 STONELEIGH DR, RIVERHEAD, NY, 11901, Riverhead, NY 11901

$660,000

2 beds

3 baths

1,972 sq ft

Condo

67 STONELEIGH DR, RIVERHEAD, NY, 11901

Community: Stoneleigh Woods at Riverhead

Country Village Estates

163 THEODORE DR, CORAM, NY, 11727, Coram, NY 11727

$472,000

2 beds

2 baths

1,261 sq ft

Condo

163 THEODORE DR, CORAM, NY, 11727

Community: Country Village Estates

Country Village Estates

190 THEODORE DR, CORAM, NY, 11727, Coram, NY 11727

$394,990

2 beds

2 baths

1,091 sq ft

Condo

190 THEODORE DR, CORAM, NY, 11727

Community: Country Village Estates

Leisure Village

167 VENTRY CT UNIT C, RIDGE, NY, 11961, Ridge, NY 11961

$215,500

1 beds

1 baths

684 sq ft

Condo

167 VENTRY CT UNIT C, RIDGE, NY, 11961

Community: Leisure Village

The Villages at Mount Sinai Park

68 LOUDEN LOOP, MOUNT SINAI, NY, 11766, Mount Sinai, NY 11766

$699,000

2 beds

2 baths

1,736 sq ft

Condo

68 LOUDEN LOOP, MOUNT SINAI, NY, 11766

Community: The Villages at Mount Sinai Park

Leisure Village

120 EXMORE CT D, RIDGE, NY, 11961, Ridge, NY 11961

$239,990

1 beds

1 baths

684 sq ft

Condo

120 EXMORE CT D, RIDGE, NY, 11961

Community: Leisure Village

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

Questions? Call us: (475) 244-9781

HarborView

92 W OVERLOOK, PORT WASHINGTON, NY, 1105..., Port Washington, NY 11050

$1,799,999

3 beds

3 baths

2,901 sq ft

Condo

92 W OVERLOOK, PORT WASHINGTON, NY, 1105...

Community: HarborView

Meadowbrook Pointe Athletic Club & Spa

323 ROOSEVELT WAY, WESTBURY, NY, 11590, Westbury, NY 11590

$889,000

2 beds

2 baths

1,328 sq ft

Condo

323 ROOSEVELT WAY, WESTBURY, NY, 11590

Community: Meadowbrook Pointe Athletic Club & Spa

Leisure Village

424 WOODBRIDGE DR D, RIDGE, NY, 11961, Ridge, NY 11961

$279,900

1 beds

1 baths

782 sq ft

Condo

424 WOODBRIDGE DR D, RIDGE, NY, 11961

Community: Leisure Village

Leisure Knoll

379 LARCHMONT CT # 379, RIDGE, NY, 11961, Ridge, NY 11961

$379,900

2 beds

2 baths

976 sq ft

Condo

379 LARCHMONT CT # 379, RIDGE, NY, 11961

Community: Leisure Knoll

Leisure Village

393 WOODBRIDGE DR UNIT A, RIDGE, NY, 119..., Ridge, NY 11961

$329,000

2 beds

1 baths

1,300 sq ft

Condo

393 WOODBRIDGE DR UNIT A, RIDGE, NY, 119...

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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294 homes near Cheshire

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

128 communities near Cheshire

294 homes near Cheshire

2 beds

1 baths

655 sq ft

Condo

2 beds

2 baths

1,390 sq ft

Condo

2 beds

1 baths

1,000 sq ft

Condo

2 beds

2 baths

941 sq ft

Condo

3 beds

2 baths

1,905 sq ft

Condo

2 beds

2 baths

1,456 sq ft

Condo

2 beds

2 baths

1,468 sq ft

Condo

2 beds

2 baths

1,133 sq ft

Condo

2 beds

1 baths

1,278 sq ft

Condo

2 beds

2 baths

1,587 sq ft

Condo

3 beds

3 baths

2,306 sq ft

Condo

2 beds

2 baths

100 sq ft

Condo

2 beds

2 baths

1,175 sq ft

House

2 beds

1 baths

840 sq ft

Mobile Home

2 beds

2 baths

941 sq ft

Condo

2 beds

2 baths

1,982 sq ft

Condo

2 beds

2 baths

1,180 sq ft

Condo

2 beds

1 baths

1,085 sq ft

Condo

3 beds

2 baths

1,909 sq ft

Condo

1 beds