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 - $400Ks

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 - $900Ks

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...

$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 - $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 - $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 - $500Ks

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 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

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 ...

$600Ks - $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 - $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

$500Ks - $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

26 SARAH CT, AMITYVILLE, NY, 11701

Community: Village Estates

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

Questions? Call us: (475) 244-9781

Plymouth Estates at Mount Sinai

166 IRA RD, MOUNT SINAI, NY, 11766, Mount Sinai, NY 11766

$579,999

2 beds

2 baths

1,820 sq ft

Townhouse

166 IRA RD, MOUNT SINAI, NY, 11766

Community: Plymouth Estates at Mount Sinai

Leisure Village

192 VENTRY CT A, RIDGE, NY, 11961, Ridge, NY 11961

$249,000

1 beds

1 baths

650 sq ft

Condo

192 VENTRY CT A, RIDGE, NY, 11961

Community: Leisure Village

Leisure Village

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

$359,000

2 beds

1 baths

1,000 sq ft

Condo

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

Community: Leisure Village

Leisure Glen

460 LEISURE DR, RIDGE, NY, 11961, Ridge, NY 11961

$550,000

2 beds

2 baths

1,691 sq ft

Condo

460 LEISURE DR, RIDGE, NY, 11961

Community: Leisure Glen

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

Leisure Village

373 WOODBRIDGE DR B, RIDGE, NY, 11961, Ridge, NY 11961

$339,990

2 beds

1 baths

1,171 sq ft

Condo

373 WOODBRIDGE DR B, RIDGE, NY, 11961

Community: Leisure Village

Greenwood Village

21 LIMETREE DR, MANORVILLE, NY, 11949, Manorville, NY 11949

$179,000

2 beds

2 baths

1,100 sq ft

Condo

21 LIMETREE DR, MANORVILLE, NY, 11949

Community: Greenwood Village

HarborView

$1,495,000

4 beds

4 baths

3,000 sq ft

Condo

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

Community: HarborView

New 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

Leisure Knoll

202 KINGSTON DR, RIDGE, NY, 11961, Ridge, NY 11961

$489,900

2 beds

2 baths

1,100 sq ft

Condo

202 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

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

New 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

New 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

Knickerbocker Bay Club

433 MAIN ST 203, PORT WASHINGTON, NY, 11..., Port Washington, NY 11050

$949,000

2 beds

2 baths

1,323 sq ft

Condo

433 MAIN ST 203, PORT WASHINGTON, NY, 11...

Community: Knickerbocker Bay Club

New 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

New 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

New Jefferson Village

52 JEFFERSON OVAL E, YORKTOWN HEIGHTS, N..., Yorktown Heights, NY 10598

$449,000

2 beds

2 baths

907 sq ft

Condo

52 JEFFERSON OVAL E, YORKTOWN HEIGHTS, N...

Community: Jefferson Village

New Heritage Hills

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

$835,000

3 beds

2 baths

1,793 sq ft

Condo

596 HERITAGE HLS B, SOMERS, NY, 10589

Community: Heritage Hills

New 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

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

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

Questions? Call us: (475) 244-9781

Leisure Knoll

145 EDINBURGH DR, RIDGE, NY, 11961, Ridge, NY 11961

$418,000

2 beds

2 baths

900 sq ft

Condo

145 EDINBURGH DR, RIDGE, NY, 11961

Community: Leisure Knoll

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

New Woodridge Strathmore Terrace

34 CHIPPENDALE DR, MOUNT SINAI, NY, 1176..., Mount Sinai, NY 11766

$499,000

2 beds

2 baths

1,335 sq ft

Townhouse

34 CHIPPENDALE DR, MOUNT SINAI, NY, 1176...

Community: Woodridge Strathmore Terrace

New Leisure Village

2 GUILFORD CT B, RIDGE, NY, 11961, Ridge, NY 11961

$519,000

2 beds

2 baths

1,767 sq ft

Condo

2 GUILFORD CT B, RIDGE, NY, 11961

Community: Leisure Village

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

Glenwood Village

1661 OLD COUNTRY RD UNIT 200, RIVERHEAD,..., Riverhead, NY 11901

$239,900

2 beds

1 baths

753 sq ft

Manufactured Home

1661 OLD COUNTRY RD UNIT 200, RIVERHEAD,...

Community: Glenwood 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

New The Waterways at Moriches

188 RIVER DR, MORICHES, NY, 11955, Moriches, NY 11955

$439,000

2 beds

2 baths

1,480 sq ft

Condo

188 RIVER DR, MORICHES, NY, 11955

Community: The Waterways at Moriches

New 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

New Fairfield at St. James

205 FLAIR CT, SMITHTOWN, NY, 11780, Smithtown, NY 11780

$619,990

3 beds

3 baths

1,600 sq ft

Condo

205 FLAIR CT, SMITHTOWN, NY, 11780

House

31 LANGDON GROVE, CARMEL, NY, 10512

Community: The Retreat at Carmel

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

281 homes near Cheshire

2 beds

1 baths

787 sq ft

Condo

2 beds

2 baths

1,982 sq ft

Condo

2 beds

2 baths

1,486 sq ft

Condo

2 beds

2 baths

1,820 sq ft

Condo

2 beds

2 baths

1,243 sq ft

Condo

2 beds

2 baths

1,820 sq ft

Townhouse

1 beds

1 baths

650 sq ft

Condo

2 beds

1 baths

1,000 sq ft

Condo

2 beds

2 baths

1,691 sq ft

Condo

2 beds

1 baths

1,200 sq ft

Condo

2 beds

1 baths

1,171 sq ft

Condo

2 beds

2 baths

1,100 sq ft

Condo

4 beds

4 baths

3,000 sq ft

Condo

2 beds

2 baths

1,134 sq ft

Condo

2 beds

2 baths

1,100 sq ft

Condo

2 beds

2 baths

1,632 sq ft

Manufactured Home

2 beds

2 baths

976 sq ft

House

2 beds

2 baths

1,200 sq ft

Condo

2 beds

2 baths

1,323 sq ft

Condo

1 beds