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

132 communities near Cheshire

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3.6 rating (7 reviews)

Heritage Village

$200ks - $500ks

Heritage Village, Southbury, CT

Resale Only | 55+ age-restricted | Built 1967 - 2005 | 2,580 homes

4 rating (1 reviews)

Jefferson Village

$100ks - $500ks

Jefferson Village, Yorktown Heights, NY

Resale Only | 55+ age-restricted | Built 1967 - 1982 | 1,000 homes

3 rating (2 reviews)

Heritage Hills

$400ks - $800ks

Heritage Hills, Somers, NY

Resale Only | Age-targeted | Built 1974 - 2006 | 2,600 homes

5 rating (2 reviews)

Oronoque Village

$200ks - $400ks

Oronoque Village, Stratford, CT

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

4 rating (8 reviews)

Glenwood Village

$100ks - $200ks

Glenwood Village, Riverhead, NY

New and Resale | 55+ age-restricted | Built 1959 - present | 588 homes

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

Questions? Call us: (475) 244-9781

3.7 rating (3 reviews)

Greenwood Village

$100ks

Greenwood Village, Manorville, NY

Resale Only | 55+ age-restricted | Built 1980 - 2000 | 512 homes

The Waterways at Moriches

$300ks - $600ks

The Waterways at Moriches, Moriches, NY

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

The Village at Oxford Gre...

$400ks - $500ks

The Village at Oxford Gre..., Oxford, CT

New and Resale | 55+ age-restricted | Built 2004 - present | 835 homes

Leisure Village

$100ks - $300ks

Leisure Village, Ridge, NY

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

Overlook

$600ks - $900ks

Overlook, Carmel, NY

New Construction | 55+ age-restricted | 300 homes

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Leisure Glen

$300ks - $400ks

Leisure Glen, Ridge, NY

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

Country Pointe Plainview

$700ks - $1Ms

Country Pointe Plainview, Plainview, NY

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

Leisure Knoll

$200ks - $400ks

Leisure Knoll, Ridge, NY

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

Rivington

$300ks - $900ks

Rivington, Danbury, CT

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

5 rating (1 reviews)

Encore Atlantic Shores

$500ks - $800ks

Encore Atlantic Shores, Eastport, NY

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

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

Questions? Call us: (475) 244-9781

The Manors at The Colony ...

$300ks - $400ks

The Manors at The Colony ..., Shirley, NY

New Construction | 55+ age-restricted | Built 2013 - present | 150 homes

Fairview at Oxford Greens

$400ks - $600ks

Fairview at Oxford Greens, Oxford, CT

New and Resale | 55+ age-restricted | Built 2019 - present | 125 homes

Stoneleigh Woods at River...

$500ks

Stoneleigh Woods at River..., Riverhead, NY

Resale Only | 55+ age-restricted | Built 2007 - 2016 | 176 homes

Spring Lake Village

$100ks - $200ks

Spring Lake Village, Southington, CT

Resale Only | 55+ age-restricted | Built 1970 - 2004 | 640 homes

5 rating (1 reviews)

Westhampton Pines

$900ks - $1Ms

Westhampton Pines, Westhampton, NY

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

Meadowbrook Pointe Athlet...

$700ks - $1Ms

Meadowbrook Pointe Athlet..., Westbury, NY

Resale Only | 55+ age-restricted | Built 2015 - 2016 | 720 homes

HarborView

$600ks - $1Ms

HarborView, Port Washington, NY

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

Snug Harbor

$600ks - $700ks

Snug Harbor, Amityville, NY

Resale Only | 55+ age-restricted | Built 1970 - 1974 | 176 homes

Dutchgate

$300ks - $500ks

Dutchgate, Valley Stream, NY

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

Liberty at Newtown

$300ks - $400ks

Liberty at Newtown, Newtown, CT

Resale Only | 55+ age-restricted | Built 2003 - 2007 | 96 homes

Vineyards at Brookfield

$400ks - $500ks

Vineyards at Brookfield, Center Moriches, NY

New Construction | 55+ age-restricted | Built 2019 - present | 146 homes

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

Questions? Call us: (475) 244-9781

3.5 rating (2 reviews)

Foxwood Village

$200ks - $400ks

Foxwood Village, Calverton, NY

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

5 rating (1 reviews)

Newtown Woods

$300ks - $500ks

Newtown Woods, Newtown, CT

New and Resale | 55+ age-restricted | Built 2011 - present | 178 homes

Eagles Walk at East Quogu...

$300ks - $400ks

Eagles Walk at East Quogu..., East Quogue, NY

Resale Only | 55+ age-restricted | Built 2004 - 2014 | 67 homes

1 rating (1 reviews)

Plymouth Estates at Mount...

$400ks - $500ks

Plymouth Estates at Mount..., Mount Sinai, NY

Resale Only | 55+ age-restricted | Built 2006 - 2013 | 285 homes

Stone Ridge Estates

$500ks - $600ks

Stone Ridge Estates, Dix Hills, NY

Resale Only | 55+ age-restricted | Built 2004 - 2013 | 76 homes

Country Pointe Preserve

$600ks - $900ks

Country Pointe PreserveYaphank, NY

New Construction | 55+ age-restricted | Built 2024 - present | 152 homes

Woodridge Strathmore Terr...

$200ks - $300ks

Woodridge Strathmore Terr..., Mount Sinai, NY

Resale Only | 55+ age-restricted | Built 1974 - 1985 | 226 homes

Vineyards at Moriches

$500ks - $600ks

Vineyards at Moriches, Center Moriches, NY

Resale Only | 55+ age-restricted | Built 2008 - 2014 | 92 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

5 rating (2 reviews)

Fairfield at St. James

$300ks - $500ks

Fairfield at St. James, St. James, NY

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

Country Village Estates

$300ks

Country Village Estates, Coram, NY

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

$500ks - $700ks

Vineyards at Blue Point, Blue Point, NY

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

The Seasons at East Meado...

$400ks - $600ks

The Seasons at East Meado..., East Meadow, NY

Resale Only | 55+ age-restricted | Built 2009 - 2012 | 404 homes

1 2 3...4

Jefferson Village

39 SUSSEX DR B, YORKTOWN, NY, 10598, Yorktown, NY 10598

$369,000

2 beds

2 baths

1,000 sq ft

Condo

39 SUSSEX DR B, YORKTOWN, NY, 10598

17 DOGWOOD LN, BROOKHAVEN, NY, 11949

Condo

783 HERITAGE VLG A, SOUTHBURY, CT, 06488

Community: Heritage Village

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

Questions? Call us: (475) 244-9781

New Hopmeadow Place

1 W ST 315, SIMSBURY, CT, 06070, Simsbury, CT 06070

$385,000

2 beds

2 baths

1,477 sq ft

Condo

1 W ST 315, SIMSBURY, CT, 06070

Community: Hopmeadow Place

New Country Village Estates

175 THEODORE DR, BROOKHAVEN, NY, 11727, Brookhaven, NY 11727

$449,000

2 beds

2 baths

1,340 sq ft

Condo

175 THEODORE DR, BROOKHAVEN, NY, 11727

Community: Country Village Estates

New Heritage Village

738 HERITAGE VLG A, SOUTHBURY, CT, 06488, Southbury, CT 06488

$329,900

2 beds

2 baths

1,398 sq ft

Condo

738 HERITAGE VLG A, SOUTHBURY, CT, 06488

Community: Heritage Village

New Granite Woods

35 NUTMEG RD B2, MIDDLEBURY, CT, 06762, Middlebury, CT 06762

$239,900

1 beds

1 baths

889 sq ft

Condo

35 NUTMEG RD B2, MIDDLEBURY, CT, 06762

Community: Granite Woods

New Woodridge Strathmore Terrace

6 COBBLESTONE WAY, BROOKHAVEN, NY, 11766, Brookhaven, NY 11766

$430,000

2 beds

2 baths

1,151 sq ft

Condo

6 COBBLESTONE WAY, BROOKHAVEN, NY, 11766

Community: Woodridge Strathmore Terrace

New Oronoque Village

393 OTTAWA LN B, STRATFORD, CT, 06614, Stratford, CT 06614

$350,000

1 beds

3 baths

1,118 sq ft

Condo

393 OTTAWA LN B, STRATFORD, CT, 06614

Community: Oronoque Village

New Foxwood Village

1407 MIDDLE RD 265, RIVERHEAD, NY, 11933, Riverhead, NY 11933

$469,999

3 beds

2 baths

1,792 sq ft

Manufactured Home

1407 MIDDLE RD 265, RIVERHEAD, NY, 11933

Community: Foxwood Village

New The Greens at Half Hollow

602 BARDINI DR, HUNTINGTON, NY, 11747, Huntington, NY 11747

$1,199,000

2 beds

4 baths

1,941 sq ft

Condo

602 BARDINI DR, HUNTINGTON, NY, 11747

Community: The Greens at Half Hollow

New Leisure Village

463 B OLDHAM CT, BROOKHAVEN, NY, 11961, Brookhaven, NY 11961

$389,990

2 beds

1 baths

1,074 sq ft

Condo

463 B OLDHAM CT, BROOKHAVEN, NY, 11961

Community: Leisure Village

New Leisure Village

472 DARWEN DR, BROOKHAVEN, NY, 11961, Brookhaven, NY 11961

$408,000

2 beds

2 baths

1,200 sq ft

Condo

472 DARWEN DR, BROOKHAVEN, NY, 11961

Community: Leisure Village

New South Pond Village

78 SILO WAY 78, BLOOMFIELD, CT, 06002, Bloomfield, CT 06002

$289,500

3 beds

3 baths

1,639 sq ft

Condo

78 SILO WAY 78, BLOOMFIELD, CT, 06002

Community: South Pond Village

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

Questions? Call us: (475) 244-9781

New Plymouth Estates at Mount Sinai

7 POND CIR, BROOKHAVEN, NY, 11766, Brookhaven, NY 11766

$665,000

2 beds

2 baths

1,274 sq ft

Condo

7 POND CIR, BROOKHAVEN, NY, 11766

Community: Plymouth Estates at Mount Sinai

New Heritage Hills

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

$599,000

2 beds

3 baths

1,550 sq ft

Condo

332 HERITAGE HLS B, SOMERS, NY, 10589

Community: Heritage Hills

New Leisure Knoll

152A LAURANCE LN A, BROOKHAVEN, NY, 1196..., Brookhaven, NY 11961

$399,999

2 beds

1 baths

724 sq ft

Condo

152A LAURANCE LN A, BROOKHAVEN, NY, 1196...

Community: Leisure Knoll

New Stratford Park

104 VICTORIA PL, HUNTINGTON, NY, 11747, Huntington, NY 11747

$949,999

3 beds

3 baths

2,423 sq ft

House

104 VICTORIA PL, HUNTINGTON, NY, 11747

Community: Stratford Park

New Newbury Village

23 STILL WATER CIR 23, BROOKFIELD, CT, 0..., Brookfield, CT 06804

$735,000

3 beds

4 baths

2,684 sq ft

Condo

23 STILL WATER CIR 23, BROOKFIELD, CT, 0...

Community: Newbury Village

New Leisure Glen

6 OAKDALE CT, BROOKHAVEN, NY, 11961, Brookhaven, NY 11961

$559,000

2 beds

2 baths

1,666 sq ft

Condo

6 OAKDALE CT, BROOKHAVEN, NY, 11961

Community: Leisure Glen

New Leisure Glen

428 LEISURE DR, BROOKHAVEN, NY, 11961, Brookhaven, NY 11961

$649,000

2 beds

2 baths

1,652 sq ft

Condo

428 LEISURE DR, BROOKHAVEN, NY, 11961

Community: Leisure Glen

New Oronoque Village

138 BISON LN B, STRATFORD, CT, 06614, Stratford, CT 06614

$480,000

2 beds

3 baths

1,438 sq ft

454 LEISURE DR, BROOKHAVEN, NY, 11961

Community: Leisure Glen

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

Questions? Call us: (475) 244-9781

New Heritage Village

857 HERITAGE VLG A, SOUTHBURY, CT, 06488, Southbury, CT 06488

$235,000

2 beds

2 baths

1,071 sq ft

Condo

857 HERITAGE VLG A, SOUTHBURY, CT, 06488

Community: Heritage Village

New Heritage Village

9 HERITAGE CIR A, SOUTHBURY, CT, 06488, Southbury, CT 06488

$275,000

2 beds

2 baths

1,071 sq ft

Condo

9 HERITAGE CIR A, SOUTHBURY, CT, 06488

Community: Heritage Village

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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132 communities

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

132 communities near Cheshire

307 homes near Cheshire

2 beds

2 baths

1,000 sq ft

Condo

3 beds

2 baths

1,716 sq ft

Condo

2 beds

2 baths

1,130 sq ft

Condo

2 beds

2 baths

1,624 sq ft

Manufactured Home

2 beds

2 baths

1,160 sq ft

House

2 beds

2 baths

1,076 sq ft

Condo

2 beds

1 baths

1,085 sq ft

Condo

2 beds

2 baths

1,476 sq ft

Condo

2 beds

2 baths

1,172 sq ft

Condo

2 beds

2 baths

1,904 sq ft

Condo

2 beds

2 baths

912 sq ft

Condo

2 beds

3 baths

1,258 sq ft

Condo

2 beds

2 baths

1,426 sq ft

Condo

2 beds

2 baths

1,000 sq ft

Condo

2 beds

4 baths

2,600 sq ft

Condo

2 beds

2 baths

1,432 sq ft

Condo

2 beds

2 baths

1,477 sq ft

Condo

2 beds

2 baths

1,340 sq ft

Condo

2 beds

2 baths

1,398 sq ft

Condo

1 beds