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

298 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

$400Ks - $700Ks

Heritage Hills, Somers, NY

Resale Only | Age-targeted | Built 1975 - 2003 | 2,600 homes

3.6 rating (7 reviews)

Heritage Village

$200Ks - $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

$400Ks - $1Ms

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

$400Ks - $600Ks

Oronoque Village, Stratford, CT

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

No reviews yet

The Village at Oxford Gre...

$500Ks - $600Ks

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

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

$300Ks - $500Ks

Leisure Knoll, Ridge, NY

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

No reviews yet

Country Pointe Plainview

$900Ks - $1Ms

Country Pointe Plainview, Plainview, NY

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

5 rating (1 reviews)

Fairfield at St. James

$500Ks - $600Ks

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 - $300Ks

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 - $400Ks

Dutchgate, Valley Stream, NY

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

No reviews yet

The Waterways at Moriches

$500Ks - $700Ks

The Waterways at Moriches, Moriches, NY

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

No reviews yet

The Retreat at Carmel

$300Ks - $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

4.6 rating (9 reviews)

Meadowbrook Pointe Links ...

$600Ks - $700Ks

Meadowbrook Pointe Links ..., Medford, NY

New and Resale | 55+ age-restricted | Built 2010 - present | 280 homes

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

Questions? Call us: (475) 244-9781

4 rating (1 reviews)

Vineyards at Blue Point

$600Ks - $900Ks

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

$700Ks - $800Ks

Encore Atlantic Shores, Eastport, NY

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

No reviews yet

The Summit at Bethel

$700Ks - $800Ks

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

$600Ks - $800Ks

Encore at Lake Grove, Lake Grove, NY

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

No reviews yet

Woodridge Strathmore Terr...

$300Ks - $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 - $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

$400Ks - $400Ks

Country Village Estates, Coram, NY

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

5 rating (1 reviews)

Sunken Pond Estates

$400Ks - $400Ks

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

196A HERITAGE HLS # 196A, SOMERS, NY, 10...

Community: Heritage Hills

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

Questions? Call us: (475) 244-9781

Meadowbrooke Pointe East Meadow

409 EMANUEL WAY # 409, EAST MEADOW, NY, ..., East Meadow, NY 11554

$725,000

2 beds

2 baths

961 sq ft

Condo

409 EMANUEL WAY # 409, EAST MEADOW, NY, ...

Community: Meadowbrooke Pointe East Meadow

Country Pointe Plainview

34203 WINTERBERRY DR, PLAINVIEW, NY, 118..., Plainview, NY 11803

$949,000

2 beds

2 baths

1,335 sq ft

Condo

34203 WINTERBERRY DR, PLAINVIEW, NY, 118...

Community: Country Pointe Plainview

Leisure Village

419 WEYMOUTH CT F, RIDGE, NY, 11961, Ridge, NY 11961

$283,000

1 beds

1 baths

782 sq ft

Condo

419 WEYMOUTH CT F, RIDGE, NY, 11961

Community: Leisure Village

Sunrise Village

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

$449,000

2 beds

1 baths

1,000 sq ft

Condo

133 REVERE DR, SAYVILLE, NY, 11782

Community: Sunrise Village

Vineyards at Brookfield

109 HALLEY DR, CENTER MORICHES, NY, 1193..., Center Moriches, NY 11934

$849,000

2 beds

3 baths

3,000 sq ft

Condo

109 HALLEY DR, CENTER MORICHES, NY, 1193...

Community: Vineyards at Brookfield

Leisure Village

116 EXMORE CT B, RIDGE, NY, 11961, Ridge, NY 11961

$299,999

2 beds

1 baths

875 sq ft

Condo

116 EXMORE CT B, RIDGE, NY, 11961

Community: Leisure Village

Plymouth Estates at Mount Sinai

211 POND CIR, MOUNT SINAI, NY, 11766, Mount Sinai, NY 11766

$598,888

2 beds

2 baths

1,662 sq ft

Condo

211 POND CIR, MOUNT SINAI, NY, 11766

Community: Plymouth Estates at Mount Sinai

Sunrise Village

14 REVERE DR, SAYVILLE, NY, 11782, Sayville, NY 11782

$525,000

2 beds

2 baths

1,046 sq ft

Condo

14 REVERE DR, SAYVILLE, NY, 11782

Community: Sunrise Village

Westhampton Pines

42 KIMBERLY DR # 42, WESTHAMPTON, NY, 11..., Westhampton, NY 11977

$1,450,000

2 beds

3 baths

2,350 sq ft

Condo

42 KIMBERLY DR # 42, WESTHAMPTON, NY, 11...

Community: Westhampton Pines

HarborView

$1,200,000

3 beds

3 baths

2,216 sq ft

Condo

100 HARBOR VIEW DR 335, PORT WASHINGTON,...

House

1407-54 MIDDLE RD 54, RIVERHEAD, NY, 119...

Community: Foxwood Village

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

Questions? Call us: (475) 244-9781

Leisure Village

314 WOODBRIDGE DR A, RIDGE, NY, 11961, Ridge, NY 11961

$349,900

2 beds

1 baths

1,278 sq ft

Condo

314 WOODBRIDGE DR A, RIDGE, NY, 11961

Community: Leisure Village

Encore Atlantic Shores

68 ENCORE, BROOKHAVEN, NY, 11941, Brookhaven, NY 11941

$849,999

2 beds

3 baths

3,000 sq ft

Condo

68 ENCORE, BROOKHAVEN, NY, 11941

Community: Encore Atlantic Shores

Leisure Village

489 FAIRWAY CT A, RIDGE, NY, 11961, Ridge, NY 11961

$422,000

2 beds

2 baths

979 sq ft

Condo

489 FAIRWAY CT A, RIDGE, NY, 11961

Community: Leisure Village

Leisure Village

156 FALMOUTH CT A, RIDGE, NY, 11961, Ridge, NY 11961

$349,997

2 beds

1 baths

1,085 sq ft

Condo

156 FALMOUTH CT A, RIDGE, NY, 11961

Community: Leisure Village

The Seasons at East Meadow

315 SPRING DR, EAST MEADOW, NY, 11554, East Meadow, NY 11554

$588,000

2 beds

2 baths

1,272 sq ft

Condo

315 SPRING DR, EAST MEADOW, NY, 11554

Community: The Seasons at East Meadow

The Greens at Half Hollow

556 BARDINI DR, MELVILLE, NY, 11747, Melville, NY 11747

$1,199,000

3 beds

3 baths

2,500 sq ft

Townhouse

556 BARDINI DR, MELVILLE, NY, 11747

Community: The Greens at Half Hollow

HarborView

$1,500,000

3 beds

3 baths

2,395 sq ft

Condo

100 HARBOR VIEW DR 230, PORT WASHINGTON,...

Community: HarborView

Heritage Hills

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

$799,000

3 beds

2 baths

1,689 sq ft

Condo

239 HERITAGE HLS B, SOMERS, NY, 10589

Community: Heritage Hills

Sunrise Village

127 REVERE DR, SAYVILLE, NY, 11782, Sayville, NY 11782

$515,000

2 beds

2 baths

1,141 sq ft

Condo

127 REVERE DR, SAYVILLE, NY, 11782

Community: Sunrise Village

Leisure Village

232 BLACKPOOL CT A, RIDGE, NY, 11961, Ridge, NY 11961

$305,000

2 beds

1 baths

836 sq ft

Condo

232 BLACKPOOL CT A, RIDGE, NY, 11961

Condo

2203 PANKIN DR, CARMEL, NY, 10512

Community: Villas at Seminary Hill

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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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298 homes near Cheshire

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

125 communities near Cheshire

298 homes near Cheshire

2 beds

2 baths

1,456 sq ft

Condo

2 beds

1 baths

1,000 sq ft

Condo

2 beds

2 baths

920 sq ft

Condo

2 beds

2 baths

941 sq ft

Condo

2 beds

2 baths

1,427 sq ft

Condo

2 beds

2 baths

961 sq ft

Condo

2 beds

2 baths

1,335 sq ft

Condo

1 beds

1 baths

782 sq ft

Condo

2 beds

1 baths

1,000 sq ft

Condo

2 beds

3 baths

3,000 sq ft

Condo

2 beds

1 baths

875 sq ft

Condo

2 beds

2 baths

1,662 sq ft

Condo

2 beds

2 baths

1,046 sq ft

Condo

2 beds

3 baths

2,350 sq ft

Condo

3 beds

3 baths

2,216 sq ft

Condo

2 beds

2 baths

1,379 sq ft

Condo

2 beds

2 baths

1,619 sq ft

Condo

1 beds

1 baths

800 sq ft

Condo

2 beds

1 baths

1,184 sq ft

Condo

2 beds