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

228 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

Leisure Village

$200Ks - $400Ks

Leisure Village, Ridge, NY

Resale Only | 55+ age-restricted | Built 1969 - 1986 | 1,500 homes

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

Rivington

$400Ks - $600Ks

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

Oronoque Village

$200Ks - $600Ks

Oronoque Village, Stratford, CT

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

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

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.

Leisure Knoll

$300Ks - $400Ks

Leisure Knoll, Ridge, NY

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

Country Pointe Plainview

$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

Leisure Glen

$400Ks

Leisure Glen, Ridge, NY

Resale Only | 55+ age-restricted | Built 1985 - 2010 | 646 homes

Spring Lake Village

$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

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

Regency at Prospect

$300Ks - $500Ks

Regency at Prospect, Prospect, CT

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

Dutchgate

$400Ks - $500Ks

Dutchgate, Valley Stream, NY

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

The Waterways at Moriches

$400Ks - $600Ks

The Waterways at Moriches, Moriches, NY

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

The Retreat at Carmel

$400Ks - $600Ks

The Retreat at Carmel, Carmel, NY

Resale Only | 55+ age-restricted | Built 2008 - 2018 | 312 homes

Overlook

$600Ks - $800Ks

Overlook, Carmel, NY

New Construction | 55+ age-restricted | 300 homes

3.5 rating (2 reviews)

Foxwood Village

$400Ks - $500Ks

Foxwood Village, Calverton, NY

Resale Only | 55+ age-restricted | Built 1986 - 2007 | 294 homes

1 rating (1 reviews)

Plymouth Estates at Mount...

$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

Vineyards at Blue Point, Blue Point, NY

Resale Only | 55+ age-restricted | Built 2016 - 2018 | 280 homes

HarborView

$900Ks - $1Ms

HarborView, Port Washington, NY

Resale Only | 55+ age-restricted | Built 2002 - 2004 | 270 homes

The Club at Melville

$500Ks

The Club at Melville, Melville, NY

Resale Only | 55+ age-restricted | Built 2015 - 2017 | 261 homes

The Seasons at Elwood

$800Ks - $900Ks

The Seasons at Elwood, East Northport, NY

Resale Only | 55+ age-restricted | Built 2018 - 2020 | 256 homes

Meadow Brook Estates

$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

The Summit at Bethel

$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 - $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

Woodridge Strathmore Terr...

$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

Saddle Lakes

$400Ks

Saddle Lakes, Riverhead, NY

Resale Only | 55+ age-restricted | Built 2000 - 2002 | 196 homes

Country Village Estates

$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

652 BALFOUR PL, MELVILLE, NY, 11747

Community: The Greens at Half Hollow

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

Questions? Call us: (475) 244-9781

Foxwood Village

1407 MIDDLE RD UNIT 258, CALVERTON, NY, ..., Calverton, NY 11933

$525,000

3 beds

2 baths

1,568 sq ft

Manufactured Home

1407 MIDDLE RD UNIT 258, CALVERTON, NY, ...

Community: Foxwood Village

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

The Seasons at East Meadow

383 SUMMER CT, EAST MEADOW, NY, 11554, East Meadow, NY 11554

$640,000

2 beds

2 baths

1,272 sq ft

Condo

383 SUMMER CT, EAST MEADOW, NY, 11554

Community: The Seasons at East Meadow

Stoneleigh Woods at Riverhead

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

$640,000

2 beds

3 baths

1,972 sq ft

Condo

67 STONELEIGH DR, RIVERHEAD, NY, 11901

Community: Stoneleigh Woods at Riverhead

Leisure Knoll

323 BROWNFIELD DR, RIDGE, NY, 11961, Ridge, NY 11961

$360,000

2 beds

1 baths

655 sq ft

Condo

323 BROWNFIELD DR, RIDGE, NY, 11961

Community: Leisure Knoll

Plymouth Estates at Mount Sinai

230 IRA RD # 230, MOUNT SINAI, NY, 11766, Mount Sinai, NY 11766

$589,999

2 beds

2 baths

1,317 sq ft

Condo

230 IRA RD # 230, MOUNT SINAI, NY, 11766

Community: Plymouth Estates at Mount Sinai

Greenwood Village

145 VILLAGE CIR, MANORVILLE, NY, 11949, Manorville, NY 11949

$199,900

2 beds

2 baths

1,100 sq ft

Condo

145 VILLAGE CIR, MANORVILLE, NY, 11949

Community: Greenwood Village

Glenwood Village

1661 OLD COUNTRY RD UNIT 280, RIVERHEAD,..., Riverhead, NY 11901

$205,000

2 beds

2 baths

1,008 sq ft

Manufactured Home

1661 OLD COUNTRY RD UNIT 280, RIVERHEAD,...

Community: Glenwood Village

The Vineyards at Miller Place

48 AVERY LN, MILLER PLACE, NY, 11764, Miller Place, NY 11764

$679,900

2 beds

3 baths

1,486 sq ft

Condo

48 AVERY LN, MILLER PLACE, NY, 11764

Community: The Vineyards at Miller Place

Westhampton Pines

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

$1,295,000

3 beds

3 baths

2,306 sq ft

Condo

112 ASHLEY DR, WESTHAMPTON, NY, 11977

Community: Westhampton Pines

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

Questions? Call us: (475) 244-9781

Greenwood Village

164 VILLAGE CIR, MANORVILLE, NY, 11949, Manorville, NY 11949

$174,990

2 beds

2 baths

938 sq ft

Manufactured Home

164 VILLAGE CIR, MANORVILLE, NY, 11949

Community: Greenwood Village

Leisure Glen

12 BALDWIN CT, RIDGE, NY, 11961, Ridge, NY 11961

$479,990

2 beds

2 baths

1,542 sq ft

Condo

12 BALDWIN CT, RIDGE, NY, 11961

Community: Leisure Glen

Jefferson Village

159 CARRIAGE CT C, YORKTOWN HEIGHTS, NY,..., Yorktown Heights, NY 10598

$569,999

2 beds

2 baths

1,300 sq ft

Condo

159 CARRIAGE CT C, YORKTOWN HEIGHTS, NY,...

Community: Jefferson Village

Greenwood Village

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

$155,900

2 beds

1 baths

1,000 sq ft

Condo

77 VILLAGE CIR, MANORVILLE, NY, 11949

Community: Greenwood Village

Leisure Village

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

$350,000

2 beds

1 baths

1,085 sq ft

Condo

46 TRENT CT C, RIDGE, NY, 11961

Community: Leisure Village

Vineyards at Moriches

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

$735,000

3 beds

3 baths

2,933 sq ft

Condo

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

Community: Vineyards at Moriches

Glenwood Village

1661 OLD COUNTRY RD 163, RIVERHEAD, NY, ..., Riverhead, NY 11901

$149,999

2 beds

1 baths

816 sq ft

Mobile Home

1661 OLD COUNTRY RD 163, RIVERHEAD, NY, ...

Community: Glenwood Village

Leisure Village

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

$359,900

2 beds

1 baths

836 sq ft

Condo

280 BERWICK CT A, RIDGE, NY, 11961

Community: Leisure Village

Glenwood Village

1661 OLD COUNTRY RD UNIT 539, RIVERHEAD,..., Riverhead, NY 11901

$399,000

2 beds

2 baths

1,500 sq ft

Manufactured Home

1661 OLD COUNTRY RD UNIT 539, RIVERHEAD,...

Community: Glenwood Village

Leisure Knoll

190 CANTERBURY DR, RIDGE, NY, 11961, Ridge, NY 11961

$434,999

2 beds

1 baths

787 sq ft

Condo

190 CANTERBURY 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

Meadowbrooke Pointe East Meadow

123 EMANUEL WAY, EAST MEADOW, NY, 11554, East Meadow, NY 11554

$729,000

2 beds

2 baths

1,390 sq ft

Condo

123 EMANUEL WAY, EAST MEADOW, NY, 11554

Community: Meadowbrooke Pointe East Meadow

The Manors at The Colony Preserve

41 GREENTREE CT, SHIRLEY, NY, 11967, Shirley, NY 11967

$535,000

2 beds

2 baths

1,800 sq ft

Condo

41 GREENTREE CT, SHIRLEY, NY, 11967

Community: The Manors at The Colony Preserve

Glenwood Village

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

$484,900

2 beds

2 baths

1,500 sq ft

Manufactured Home

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

Community: Glenwood Village

The Waterways at Moriches

546 HIGHLAND CT, MORICHES, NY, 11955, Moriches, NY 11955

$499,990

2 beds

2 baths

1,497 sq ft

Condo

546 HIGHLAND CT, MORICHES, NY, 11955

Community: The Waterways at Moriches

The Waterways at Moriches

414 LINDSAY LN, MORICHES, NY, 11955, Moriches, NY 11955

$535,000

2 beds

2 baths

2,141 sq ft

Condo

414 LINDSAY LN, MORICHES, NY, 11955

Community: The Waterways at Moriches

Jefferson Village

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

$675,000

2 beds

2 baths

1,555 sq ft

Condo

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

Community: Jefferson Village

The Waterways at Moriches

244 RIVER DR, MORICHES, NY, 11955, Moriches, NY 11955

$625,000

2 beds

2 baths

1,960 sq ft

Condo

244 RIVER DR, MORICHES, NY, 11955

Community: The Waterways at Moriches

Stoneleigh Woods at Riverhead

18 KENNSINGTON CT, RIVERHEAD, NY, 11901, Riverhead, NY 11901

$665,000

2 beds

3 baths

2,172 sq ft

Condo

18 KENNSINGTON CT, RIVERHEAD, NY, 11901

Community: Stoneleigh Woods at Riverhead

Strathmore Gate East

141 FORGE LN, CORAM, NY, 11727, Coram, NY 11727

$319,000

1 beds

1 baths

728 sq ft

Condo

141 FORGE LN, CORAM, NY, 11727

Community: Strathmore Gate East

Meadowbrook Pointe Athletic Club & Spa

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

$875,000

2 beds

2 baths

1,328 sq ft

Condo

323 ROOSEVELT WAY, WESTBURY, NY, 11590

House

2 LIMETREE DR, MANORVILLE, NY, 11949

Community: Greenwood 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.

Want more information about active adult communities around Cheshire?

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228 homes near Cheshire

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

129 communities near Cheshire

228 homes near Cheshire

1 beds

2 baths

929 sq ft

Condo

2 beds

2 baths

1,200 sq ft

Condo

2 beds

2 baths

1,100 sq ft

Condo

1 beds

1 baths

800 sq ft

Condo

3 beds

3 baths

2,400 sq ft

Condo

3 beds

2 baths

1,568 sq ft

Manufactured Home

2 beds

1 baths

874 sq ft

Condo

2 beds

2 baths

1,272 sq ft

Condo

2 beds

3 baths

1,972 sq ft

Condo

2 beds

1 baths

655 sq ft

Condo

2 beds

2 baths

1,317 sq ft

Condo

2 beds

2 baths

1,100 sq ft

Condo

2 beds

2 baths

1,008 sq ft

Manufactured Home

2 beds

3 baths

1,486 sq ft

Condo

3 beds

3 baths

2,306 sq ft

Condo

2 beds

2 baths

938 sq ft

Manufactured Home

2 beds

2 baths

1,542 sq ft

Condo

2 beds

2 baths

1,300 sq ft

Condo

2 beds

1 baths

1,000 sq ft

Condo

2 beds