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

125 communities 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 - $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 - $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

$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 (1 reviews)

Fairfield at St. James

$400Ks - $600Ks

Fairfield at St. James, St. James, NY

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

No reviews yet

Leisure Glen

$400Ks - $600Ks

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...

$600Ks - $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 - $600Ks

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 ...

$300Ks - $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

$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

$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...

$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 - $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

5 rating (1 reviews)

Westhampton Pines

$900Ks - $1Ms

Westhampton Pines, Westhampton, NY

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

1 2 3...4

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

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

Community: Leisure Village

Leisure Village

186 VENTRY CT D, RIDGE, NY, 11961, Ridge, NY 11961

$339,900

2 beds

1 baths

916 sq ft

Condo

186 VENTRY CT D, RIDGE, NY, 11961

Community: Leisure Village

Foxwood Village

1407 MIDDLE RD UNIT 22, CALVERTON, NY, 1..., Calverton, NY 11933

$389,999

2 beds

2 baths

1,700 sq ft

Manufactured Home

1407 MIDDLE RD UNIT 22, CALVERTON, NY, 1...

Community: Foxwood Village

Leisure Village

411A WEYMOUTH CT # 411A, RIDGE, NY, 1196..., Ridge, NY 11961

$349,000

2 beds

1 baths

1,000 sq ft

Condo

411A WEYMOUTH CT # 411A, RIDGE, NY, 1196...

Community: Leisure Village

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

Questions? Call us: (475) 244-9781

Leisure Village

369B WOODBRIDGE DR 55+, BROOKHAVEN, NY, ..., Brookhaven, NY 11961

$344,000

2 beds

1 baths

975 sq ft

Condo

369B WOODBRIDGE DR 55+, BROOKHAVEN, NY, ...

Community: Leisure Village

Leisure Village

137 EASTBOURNE CT B, RIDGE, NY, 11961, Ridge, NY 11961

$249,000

2 beds

1 baths

836 sq ft

Condo

137 EASTBOURNE CT B, RIDGE, NY, 11961

Community: Leisure Village

Meadowbrook Pointe Athletic Club & Spa

481 PACING WAY, WESTBURY, NY, 11590, Westbury, NY 11590

$1,100,000

2 beds

3 baths

2,800 sq ft

Condo

481 PACING WAY, WESTBURY, NY, 11590

Community: Meadowbrook Pointe Athletic Club & Spa

Jefferson Village

84 MOLLY PITCHER LN H, YORKTOWN HEIGHTS,..., Yorktown Heights, NY 10598

$350,000

2 beds

2 baths

1,100 sq ft

Condo

84 MOLLY PITCHER LN H, YORKTOWN HEIGHTS,...

Community: Jefferson Village

Stone Ridge Estates

108 JOSEPH LN, DIX HILLS, NY, 11746, Dix Hills, NY 11746

$799,999

2 beds

2 baths

1,695 sq ft

Condo

108 JOSEPH LN, DIX HILLS, NY, 11746

Community: Stone Ridge Estates

The Waterways at Moriches

107 E MIDLAND POND CT, MORICHES, NY, 119..., Moriches, NY 11955

$499,907

2 beds

2 baths

2,141 sq ft

Condo

107 E MIDLAND POND CT, MORICHES, NY, 119...

Community: The Waterways at Moriches

Strathmore Gate East

9 FORGE LN, CORAM, NY, 11727, Coram, NY 11727

$334,999

2 beds

2 baths

1,300 sq ft

Condo

9 FORGE LN, CORAM, NY, 11727

Community: Strathmore Gate East

New Leisure Village

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

$284,900

1 beds

1 baths

782 sq ft

Condo

424 WOODBRIDGE DR D, RIDGE, NY, 11961

Community: Leisure Village

New Heritage Hills

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

$629,000

2 beds

2 baths

1,296 sq ft

Condo

659 HERITAGE HLS D, SOMERS, NY, 10589

Community: Heritage Hills

New Heritage Hills

954 HERITAGE HLS F, SOMERS, NY, 10589, Somers, NY 10589

$465,000

1 beds

2 baths

967 sq ft

Condo

954 HERITAGE HLS F, SOMERS, NY, 10589

Community: Heritage Hills

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

Questions? Call us: (475) 244-9781

New Country Pointe Plainview

29304 SPRUCE POND CIR, PLAINVIEW, NY, 11..., Plainview, NY 11803

$1,600,000

2 beds

2 baths

2,000 sq ft

Condo

29304 SPRUCE POND CIR, PLAINVIEW, NY, 11...

Community: Country Pointe Plainview

New Sunrise Village

150 REVERE DR, SAYVILLE, NY, 11782, Sayville, NY 11782

$519,990

2 beds

2 baths

1,046 sq ft

Condo

150 REVERE DR, SAYVILLE, NY, 11782

Community: Sunrise Village

Leisure Village

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

$339,000

2 beds

1 baths

1,300 sq ft

Condo

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

Community: Leisure Village

Setauket Meadows

131 EMILYS WAY, EAST SETAUKET, NY, 11733, East Setauket, NY 11733

$735,000

2 beds

3 baths

1,773 sq ft

Condo

131 EMILYS WAY, EAST SETAUKET, NY, 11733

Community: Setauket Meadows

The Villages at Mount Sinai Park

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

$729,000

2 beds

2 baths

1,736 sq ft

Condo

109 LOUDEN LOOP, MOUNT SINAI, NY, 11766

Community: The Villages at Mount Sinai Park

Greenwood Village

57 DOGWOOD LN, MANORVILLE, NY, 11949, Manorville, NY 11949

$159,999

2 beds

2 baths

1,000 sq ft

Condo

57 DOGWOOD LN, MANORVILLE, NY, 11949

Community: Greenwood Village

The Greens at Half Hollow

1126 SAVOY DR, MELVILLE, NY, 11747, Melville, NY 11747

$629,888

2 beds

2 baths

1,150 sq ft

Condo

1126 SAVOY DR, MELVILLE, NY, 11747

Community: The Greens at Half Hollow

Encore Atlantic Shores

167 MELODY CT, EASTPORT, NY, 11941, Eastport, NY 11941

$975,000

3 beds

3 baths

3,136 sq ft

Condo

167 MELODY CT, EASTPORT, NY, 11941

Community: Encore Atlantic Shores

The Villas at Narragansett

705 NARRAGANSETT VILLAS DR, LINDENHURST,..., Lindenhurst, NY 11757

$649,000

2 beds

2 baths

1,173 sq ft

Condo

705 NARRAGANSETT VILLAS DR, LINDENHURST,...

Community: The Villas at Narragansett

The Greens at Half Hollow

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

$1,299,000

3 beds

4 baths

3,200 sq ft

Condo

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

Community: The Greens at Half Hollow

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

Questions? Call us: (475) 244-9781

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

The Villages at Mount Sinai Park

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

$829,000

2 beds

3 baths

2,229 sq ft

Condo

25 LOUDEN LOOP, MOUNT SINAI, NY, 11766

Community: The Villages at Mount Sinai Park

New Dutchgate

802 WILLOW LN, VALLEY STREAM, NY, 11580, Valley Stream, NY 11580

$480,000

2 beds

2 baths

941 sq ft

Condo

802 WILLOW LN, VALLEY STREAM, NY, 11580

Community: Dutchgate

Jefferson Village

15 ESSEX PL 15K, YORKTOWN, NY, 10598, Yorktown, NY 10598

$375,000

2 beds

1 baths

1,000 sq ft

Condo

15 ESSEX PL 15K, YORKTOWN, NY, 10598

Community: Jefferson Village

The Greens at Half Hollow

423 FLORENCIA PL, MELVILLE, NY, 11747, Melville, NY 11747

$1,275,000

3 beds

3 baths

2,500 sq ft

Condo

423 FLORENCIA PL, MELVILLE, NY, 11747

Community: The Greens at Half Hollow

The Greens at Half Hollow

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

$649,000

2 beds

2 baths

1,134 sq ft

Condo

911 ALTESSA BLVD, MELVILLE, NY, 11747

Community: The Greens at Half Hollow

Glenwood Village

1661 OLD COUNTRY RD UNIT 543, RIVERHEAD,..., Riverhead, NY 11901

$410,000

2 beds

2 baths

1,632 sq ft

Manufactured Home

1661 OLD COUNTRY RD UNIT 543, RIVERHEAD,...

Community: Glenwood Village

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

Kensington Estates

242 COACH DR, WOODBURY, NY, 11797, Woodbury, NY 11797

$868,000

2 beds

2 baths

1,100 sq ft

Condo

242 COACH DR, WOODBURY, NY, 11797

Community: Kensington Estates

Leisure Knoll

151 LAURANCE LN, RIDGE, NY, 11961, Ridge, NY 11961

$439,900

2 beds

1 baths

1,116 sq ft

Condo

151 LAURANCE LN, RIDGE, NY, 11961

Community: Leisure Knoll

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

Questions? Call us: (475) 244-9781

New The Greens at Half Hollow

666 VERONA DR, MELVILLE, NY, 11747, Melville, NY 11747

$1,149,000

2 beds

3 baths

1,941 sq ft

Condo

666 VERONA DR, MELVILLE, NY, 11747

Community: The Greens at Half Hollow

Glenwood Village

1661 OLD COUNTRY RD UNIT 563, RIVERHEAD,..., Riverhead, NY 11901

$489,000

2 beds

2 baths

1,500 sq ft

Manufactured Home

1661 OLD COUNTRY RD UNIT 563, RIVERHEAD,...

Community: Glenwood Village

New Kensington Estates

48 PLAINVIEW RD, WOODBURY, NY, 11797, Woodbury, NY 11797

$2,499,999

6 beds

5 baths

4,333 sq ft

House

48 PLAINVIEW RD, WOODBURY, NY, 11797

Community: Kensington Estates

Greenwood Village

77 VILLAGE CIR, MANORVILLE, NY, 11949, Manorville, NY 11949

$159,990

2 beds

1 baths

1,000 sq ft

Condo

77 VILLAGE CIR, MANORVILLE, NY, 11949

Community: Greenwood Village

New Plymouth Estates at Mount Sinai

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

$649,999

2 beds

3 baths

1,306 sq ft

Condo

109 POND CIR, MOUNT SINAI, NY, 11766

Community: Plymouth Estates at Mount Sinai

1 2 3 4 5 6 7…8

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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125 communities 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

2 baths

1,375 sq ft

Condo

1 beds

1 baths

680 sq ft

House

2 beds

1 baths

916 sq ft

Condo

2 beds

2 baths

1,700 sq ft

Manufactured Home

2 beds

1 baths

1,000 sq ft

Condo

2 beds

1 baths

975 sq ft

Condo

2 beds

1 baths

836 sq ft

Condo

2 beds

3 baths

2,800 sq ft

Condo

2 beds

2 baths

1,100 sq ft

Condo

2 beds

2 baths

1,695 sq ft

Condo

2 beds

2 baths

2,141 sq ft

Condo

2 beds

2 baths

1,300 sq ft

Condo

1 beds

1 baths

782 sq ft

Condo

2 beds

2 baths

1,296 sq ft

Condo

1 beds

2 baths

967 sq ft

Condo

2 beds

2 baths

2,000 sq ft

Condo

2 beds

2 baths

1,046 sq ft

Condo

2 beds

1 baths

1,300 sq ft

Condo

2 beds

3 baths

1,773 sq ft

Condo

2 beds