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 - $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

$900Ks - $900Ks

Rivington, Danbury, CT

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

4 rating (1 reviews)

Jefferson Village

$200Ks - $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...

$600Ks - $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 - $800Ks

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

$400Ks - $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 - $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 - $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 - $400Ks

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

$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

$600Ks - $800Ks

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 - $700Ks

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

1 2 3 4

Heritage Village

761 HERITAGE VLG D, SOUTHBURY, CT, 06488, Southbury, CT 06488

$245,000

2 beds

2 baths

1,063 sq ft

Condo

761 HERITAGE VLG D, SOUTHBURY, CT, 06488

Community: Heritage Village

Glenwood Village

1661 OLD COUNTRY RD 435, RIVERHEAD, NY, ..., Riverhead, NY 11901

$299,500

2 beds

2 baths

1,270 sq ft

Mobile Home

1661 OLD COUNTRY RD 435, RIVERHEAD, NY, ...

Community: Glenwood Village

Jefferson Village

73 INDEPENDENCE CT D, YORKTOWN, NY, 1059..., Yorktown, NY 10598

$385,000

2 beds

2 baths

1,100 sq ft

Condo

73 INDEPENDENCE CT D, YORKTOWN, NY, 1059...

Community: Jefferson Village

Leisure Village

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

$379,999

2 beds

1 baths

1,200 sq ft

Condo

28 TRENT CT B, RIDGE, NY, 11961

Community: Leisure Village

HarborView

$1,495,000

4 beds

4 baths

3,000 sq ft

Condo

161 HARBOR VIEW DR, PORT WASHINGTON, NY,...

Community: HarborView

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

Questions? Call us: (475) 244-9781

New Leisure Glen

475 LEISURE DR, RIDGE, NY, 11961, Ridge, NY 11961

$549,000

2 beds

2 baths

1,417 sq ft

Condo

475 LEISURE DR, RIDGE, NY, 11961

Community: Leisure Glen

Heritage Hills

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

$610,000

2 beds

2 baths

1,468 sq ft

Condo

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

Community: Heritage Hills

The Villages at Mount Sinai Park

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

$749,900

2 beds

2 baths

1,736 sq ft

Condo

109 LOUDEN LOOP, MOUNT SINAI, NY, 11766

Community: The Villages at Mount Sinai Park

Fairfield at St. James

605 CABOT CT 605, SMITHTOWN, NY, 11780, Smithtown, NY 11780

$499,000

2 beds

2 baths

1,134 sq ft

Condo

605 CABOT CT 605, SMITHTOWN, NY, 11780

Community: Fairfield at St. James

New The Seasons at East Meadow

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

$649,000

2 beds

2 baths

1,358 sq ft

Condo

217 SPRING DR, EAST MEADOW, NY, 11554

Community: The Seasons at East Meadow

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

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

$267,900

1 beds

1 baths

875 sq ft

Condo

259 NEWCASTLE CT E, RIDGE, NY, 11961

Community: Leisure Village

New The Waterways at Moriches

365 SEABREEZE CT, MORICHES, NY, 11955, Moriches, NY 11955

$595,000

2 beds

2 baths

1,930 sq ft

Condo

365 SEABREEZE CT, MORICHES, NY, 11955

Community: The Waterways at Moriches

Leisure Knoll

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

$449,900

2 beds

1 baths

1,116 sq ft

Condo

151 LAURANCE LN, RIDGE, NY, 11961

Community: Leisure Knoll

Leisure Village

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

$249,900

1 beds

1 baths

684 sq ft

Condo

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

Community: Leisure Village

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

Questions? Call us: (475) 244-9781

The Vineyards at Miller Place

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

$599,000

2 beds

3 baths

1,486 sq ft

Condo

7 HALLEY LN, MILLER PLACE, NY, 11764

Community: The Vineyards at Miller Place

New Leisure Knoll

304 KINGSTON CT, RIDGE, NY, 11961, Ridge, NY 11961

$449,000

2 beds

2 baths

976 sq ft

Condo

304 KINGSTON CT, RIDGE, NY, 11961

Community: Leisure Knoll

Leisure Knoll

201 KINGSTON DR, RIDGE, NY, 11961, Ridge, NY 11961

$449,000

2 beds

2 baths

976 sq ft

House

201 KINGSTON DR, RIDGE, NY, 11961

Community: Leisure Knoll

Jefferson Village

118 VILLAGE RD A, YORKTOWN HEIGHTS, NY, ..., Yorktown Heights, NY 10598

$399,999

2 beds

2 baths

1,200 sq ft

Condo

118 VILLAGE RD A, YORKTOWN HEIGHTS, NY, ...

Community: Jefferson Village

New Heritage Hills

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

$849,000

3 beds

2 baths

1,905 sq ft

Condo

623 HERITAGE HLS B, SOMERS, NY, 10589

Community: Heritage Hills

The Greens at Half Hollow

170 ALTESSA BLVD, MELVILLE, NY, 11747, Melville, NY 11747

$1,599,000

2 beds

2 baths

2,500 sq ft

Condo

170 ALTESSA BLVD, MELVILLE, NY, 11747

Community: The Greens at Half Hollow

Meadowbrook Pointe Links & Spa

142 AUGUSTA DR, MEDFORD, NY, 11763, Medford, NY 11763

$729,990

2 beds

3 baths

1,691 sq ft

Condo

142 AUGUSTA DR, MEDFORD, NY, 11763

Community: Meadowbrook Pointe Links & Spa

Leisure Village

286 BERWICK CT A, RIDGE, NY, 11961, Ridge, NY 11961

$349,000

2 beds

1 baths

1,085 sq ft

Condo

286 BERWICK CT A, RIDGE, NY, 11961

Community: Leisure Village

New The Greens at Half Hollow

708 BALFOUR PL, MELVILLE, NY, 11747, Melville, NY 11747

$1,299,999

3 beds

3 baths

2,500 sq ft

Condo

708 BALFOUR PL, MELVILLE, NY, 11747

Community: The Greens at Half Hollow

Glenwood Village

1661 OLD COUNTRY RD 540, RIVERHEAD, NY, ..., Riverhead, NY 11901

$425,000

2 beds

2 baths

1,700 sq ft

Manufactured Home

1661 OLD COUNTRY RD 540, RIVERHEAD, NY, ...

Community: Glenwood Village

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

Questions? Call us: (475) 244-9781

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

Jefferson Village

4 DEVON CT B, YORKTOWN HEIGHTS, NY, 1059..., Yorktown Heights, NY 10598

$450,000

2 beds

1 baths

975 sq ft

Condo

4 DEVON CT B, YORKTOWN HEIGHTS, NY, 1059...

Community: Jefferson Village

Meadowbrooke Pointe East Meadow

417 EMANUEL WAY # 417, EAST MEADOW, NY, ..., East Meadow, NY 11554

$725,000

2 beds

2 baths

961 sq ft

Condo

417 EMANUEL WAY # 417, EAST MEADOW, NY, ...

Community: Meadowbrooke Pointe East Meadow

The Greens at Half Hollow

1082 SAVOY DR, MELVILLE, NY, 11747, Melville, NY 11747

$634,999

2 beds

2 baths

1,114 sq ft

Condo

1082 SAVOY DR, MELVILLE, NY, 11747

Community: The Greens at Half Hollow

New The Greens at Half Hollow

855 VERONA DR, MELVILLE, NY, 11747, Melville, NY 11747

$680,000

2 beds

2 baths

1,197 sq ft

Condo

855 VERONA DR, MELVILLE, NY, 11747

Community: The Greens at Half Hollow

Stone Ridge Estates

156 CHRISTINE DR, DIX HILLS, NY, 11746, Dix Hills, NY 11746

$800,000

2 beds

2 baths

1,700 sq ft

Condo

156 CHRISTINE DR, DIX HILLS, NY, 11746

Community: Stone Ridge Estates

Jefferson Village

32 CAMBRIDGE CT A, YORKTOWN HEIGHTS, NY,..., Yorktown Heights, NY 10598

$375,000

2 beds

1 baths

951 sq ft

Condo

32 CAMBRIDGE CT A, YORKTOWN HEIGHTS, NY,...

Community: Jefferson Village

Encore at Lake Grove

203 SYMPHONY DR, LAKE GROVE, NY, 11755, Lake Grove, NY 11755

$644,500

2 beds

3 baths

1,413 sq ft

Condo

203 SYMPHONY DR, LAKE GROVE, NY, 11755

Community: Encore at Lake Grove

Heritage Hills

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

$700,000

3 beds

2 baths

1,780 sq ft

Condo

133 HERITAGE HLS B, SOMERS, NY, 10589

Community: Heritage Hills

New Heritage Hills

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

$440,000

1 beds

2 baths

967 sq ft

Condo

531 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 Village

305 TORQUAY CT UNIT C, RIDGE, NY, 11961, Ridge, NY 11961

$364,500

2 beds

1 baths

836 sq ft

House

305 TORQUAY CT UNIT C, RIDGE, NY, 11961

Community: Leisure Village

The Seasons at East Meadow

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

$589,000

2 beds

2 baths

1,358 sq ft

Condo

469 SPRING DR, EAST MEADOW, NY, 11554

Community: The Seasons at East Meadow

Heritage Hills

582 HERITAGE HLS A, SOMERS, NY, 10589, Somers, NY 10589

$450,000

1 beds

1 baths

967 sq ft

Condo

582 HERITAGE HLS A, SOMERS, NY, 10589

Community: Heritage Hills

Kensington Estates

46 PLAINVIEW RD, WOODBURY, NY, 11797, Woodbury, NY 11797

$2,999,999

6 beds

5 baths

4,333 sq ft

House

46 PLAINVIEW RD, WOODBURY, NY, 11797

Community: Kensington Estates

Encore Atlantic Shores

226 SONATA CT, EASTPORT, NY, 11941, Eastport, NY 11941

$689,000

2 beds

2 baths

1,605 sq ft

Condo

226 SONATA CT, EASTPORT, NY, 11941

Community: Encore Atlantic Shores

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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125 communities near Cheshire

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

125 communities near Cheshire

295 homes near Cheshire

2 beds

2 baths

1,063 sq ft

Condo

2 beds

2 baths

1,270 sq ft

Mobile Home

2 beds

2 baths

1,100 sq ft

Condo

2 beds

1 baths

1,200 sq ft

Condo

4 beds

4 baths

3,000 sq ft

Condo

2 beds

2 baths

1,417 sq ft

Condo

2 beds

2 baths

1,468 sq ft

Condo

2 beds

2 baths

1,736 sq ft

Condo

2 beds

2 baths

1,134 sq ft

Condo

2 beds

2 baths

1,358 sq ft

Condo

2 beds

2 baths

1,183 sq ft

Condo

1 beds

1 baths

875 sq ft

Condo

2 beds

2 baths

1,930 sq ft

Condo

2 beds

1 baths

1,116 sq ft

Condo

1 beds

1 baths

684 sq ft

Condo

2 beds

3 baths

1,486 sq ft

Condo

2 beds

2 baths

976 sq ft

Condo

2 beds

2 baths

976 sq ft

House

2 beds

2 baths

1,200 sq ft

Condo

3 beds