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

130 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

3 rating (2 reviews)

Heritage Hills

- $900ks

Heritage Hills, Somers, NY

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

Leisure Village

$100ks - $300ks

Leisure Village, Ridge, NY

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

Oronoque Village

$200ks - $400ks

Oronoque Village, Stratford, CT

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

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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

Overlook

$600ks - $900ks

Overlook, Carmel, NY

New Construction | 55+ age-restricted | 300 homes

Leisure Knoll

$200ks - $400ks

Leisure Knoll, Ridge, NY

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

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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

4 rating (8 reviews)

Glenwood Village

$100ks - $200ks

Glenwood Village, Riverhead, NY

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

Rivington

$300ks - $900ks

Rivington, Danbury, CT

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

Leisure Glen

$300ks - $400ks

Leisure Glen, Ridge, NY

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

Fairview at Oxford Greens

$400ks - $600ks

Fairview at Oxford Greens, Oxford, CT

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

HarborView

$600ks - $1Ms

HarborView, Port Washington, NY

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

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

Questions? Call us: (475) 244-9781

5 rating (1 reviews)

Encore Atlantic Shores

$500ks - $800ks

Encore Atlantic Shores, Eastport, NY

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

Setauket Meadows

$500ks - $600ks

Setauket Meadows, Setauket, NY

Resale Only | 55+ age-restricted | Built 2005 - 2007 | 150 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)

Newtown Woods

$300ks - $500ks

Newtown Woods, Newtown, CT

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

The Manors at The Colony ...

$300ks - $400ks

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

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

5 rating (1 reviews)

Sunrise Village

$400ks

Sunrise Village, Sayville, NY

Resale Only | 55+ age-restricted | Built 1985 - 1990 | 213 homes

Country Pointe Preserve

$600ks - $900ks

Country Pointe PreserveYaphank, NY

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

Country Pointe Plainview

$700ks - $1Ms

Country Pointe Plainview, Plainview, NY

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

Breton Hills

$500ks

Breton Hills, Glen Cove, NY

New Construction | 55+ age-restricted | Built 2019 - present | 72 homes

5 rating (1 reviews)

The Villages at Mount Sin...

$600ks

The Villages at Mount Sin..., Mount Sinai, NY

Resale Only | 55+ age-restricted | Built 2005 - 2007 | 185 homes

Spring Lake Village

$100ks - $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

South Pond Village

$300ks - $400ks

South Pond Village, Bloomfield, CT

Resale Only | 55+ age-restricted | Built 1999 - 2005 | 151 homes

The Coves at Melville

$500ks

The Coves at Melville, Melville, NY

Resale Only | 62+ age-restricted | Built 2004 - 2005 | 175 homes

Meadowbrook Pointe Athlet...

$700ks - $1Ms

Meadowbrook Pointe Athlet..., Westbury, NY

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

5 rating (1 reviews)

Westhampton Pines

$900ks - $1Ms

Westhampton Pines, Westhampton, NY

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

Village Estates

$300ks - $400ks

Village Estates, Amityville, NY

Resale Only | 55+ age-restricted | Built 2006 - 2008 | 138 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

3.5 rating (2 reviews)

Foxwood Village

$200ks - $400ks

Foxwood Village, Calverton, NY

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

The Retreat at Carmel

$300ks - $800ks

The Retreat at Carmel, Carmel, NY

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

Stoneleigh Woods at Carme...

$400ks

Stoneleigh Woods at Carme..., Carmel, NY

Resale Only | 55+ age-restricted | Built 2012 - 2017 | 68 homes

Regency at Woodbridge

$500ks - $700ks

Regency at Woodbridge, Woodbridge, CT

New Construction | 55+ age-restricted | Built 2023 - present | 70 homes

Village Vistas

$800ks - $1Ms

Village Vistas, Port Jefferson, NY

Resale Only | 55+ age-restricted | Built 2013 - 2017 | 43 homes

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

Questions? Call us: (475) 244-9781

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

5 rating (1 reviews)

Sunken Pond Estates

$400ks

Sunken Pond Estates, Riverhead, NY

Resale Only | 55+ age-restricted | Built 2003 - 2005 | 194 homes

1 2 3...4

New Stone Ridge Estates

170 LARRY LN, HUNTINGTON, NY, 11746, Huntington, NY 11746

$789,000

2 beds

2 baths

1,415 sq ft

Condo

170 LARRY LN, HUNTINGTON, NY, 11746

Community: Stone Ridge Estates

New Bidwell Village

94 STONEHOUSE RD 14, COVENTRY, CT, 06238, Coventry, CT 06238

$395,000

3 beds

4 baths

1,726 sq ft

Condo

94 STONEHOUSE RD 14, COVENTRY, CT, 06238

Community: Bidwell Village

New Fairfield at St. James

604 CABOT CT 604, SMITHTOWN, NY, 11780, Smithtown, NY 11780

$499,000

2 beds

2 baths

1,135 sq ft

Condo

604 CABOT CT 604, SMITHTOWN, NY, 11780

Community: Fairfield at St. James

New Whitney Glen

32 WHITNEY GLN 32, WESTPORT, CT, 06880, Westport, CT 06880

$459,000

1 beds

2 baths

949 sq ft

Condo

32 WHITNEY GLN 32, WESTPORT, CT, 06880

Community: Whitney Glen

New Encore at Lake Grove

58 SYMPHONY DR, BROOKHAVEN, NY, 11755, Brookhaven, NY 11755

$629,990

3 beds

3 baths

Condo

58 SYMPHONY DR, BROOKHAVEN, NY, 11755

Community: Encore at Lake Grove

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

Questions? Call us: (475) 244-9781

New South Pond Village

20 REED CT 20, BLOOMFIELD, CT, 06002, Bloomfield, CT 06002

$245,000

2 beds

2 baths

1,202 sq ft

Condo

20 REED CT 20, BLOOMFIELD, CT, 06002

Community: South Pond Village

New Heritage Hills

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

$499,000

2 beds

2 baths

1,427 sq ft

Condo

234 HERITAGE HLS A, SOMERS, NY, 10589

Community: Heritage Hills

New Country Pointe Plainview

32103 SPRUCE POND CIR, OYSTER BAY, NY, 1..., Oyster Bay, NY 11803

$1,075,000

2 beds

2 baths

1,335 sq ft

Condo

32103 SPRUCE POND CIR, OYSTER BAY, NY, 1...

Community: Country Pointe Plainview

New Pond Spring Village

35 OCTOBER LN 35, BEACON FALLS, CT, 0646..., Beacon Falls, CT 06468

$420,000

2 beds

3 baths

1,328 sq ft

Condo

35 OCTOBER LN 35, BEACON FALLS, CT, 0646...

Community: Pond Spring Village

New Leisure Knoll

520 CRANSTON LN, BROOKHAVEN, NY, 11961, Brookhaven, NY 11961

$499,999

2 beds

2 baths

1,394 sq ft

Condo

520 CRANSTON LN, BROOKHAVEN, NY, 11961

Community: Leisure Knoll

New Heritage Village

551 HERITAGE VLG B, SOUTHBURY, CT, 06488, Southbury, CT 06488

$245,000

1 beds

1 baths

928 sq ft

Condo

551 HERITAGE VLG B, SOUTHBURY, CT, 06488

Community: Heritage Village

New Oronoque Village

298 BATON LN 298 A, STRATFORD, CT, 06614, Stratford, CT 06614

$435,000

1 beds

2 baths

1,175 sq ft

Condo

298 BATON LN 298 A, STRATFORD, CT, 06614

Community: Oronoque Village

New Heritage Hills

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

$875,000

2 beds

2 baths

1,663 sq ft

Condo

798 HERITAGE HLS A, SOMERS, NY, 10589

Community: Heritage Hills

New Fairfield at St. James

604 GOTHAM DR, SMITHTOWN, NY, 11780, Smithtown, NY 11780

$449,999

1 beds

2 baths

954 sq ft

Condo

604 GOTHAM DR, SMITHTOWN, NY, 11780

Community: Fairfield at St. James

New Leisure Knoll

8 COVENTRY CT, BROOKHAVEN, NY, 11961, Brookhaven, NY 11961

$450,000

2 beds

2 baths

1,412 sq ft

Condo

8 COVENTRY CT, BROOKHAVEN, NY, 11961

Community: Leisure Knoll

New Jefferson Village

142 FLINTLOCK WAY F, YORKTOWN, NY, 10598, Yorktown, NY 10598

$629,000

2 beds

2 baths

1,302 sq ft

Condo

142 FLINTLOCK WAY F, YORKTOWN, NY, 10598

Community: Jefferson Village

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

Questions? Call us: (475) 244-9781

New The Greens at Half Hollow

155 ALTESSA BLVD, HUNTINGTON, NY, 11747, Huntington, NY 11747

$1,599,000

3 beds

3 baths

2,700 sq ft

Condo

155 ALTESSA BLVD, HUNTINGTON, NY, 11747

Community: The Greens at Half Hollow

New Heritage Hills

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

$575,000

3 beds

2 baths

1,689 sq ft

Condo

220 HERITAGE HLS B, SOMERS, NY, 10589

Community: Heritage Hills

New Heritage Hills

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

$475,000

1 beds

2 baths

967 sq ft

Condo

670 HERITAGE HLS B, SOMERS, NY, 10589

Community: Heritage Hills

New Leisure Glen

104 GLEN DR, BROOKHAVEN, NY, 11961, Brookhaven, NY 11961

$589,900

2 beds

2 baths

1,635 sq ft

Condo

104 GLEN DR, BROOKHAVEN, NY, 11961

Community: Leisure Glen

New Heritage Hills

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

$640,000

2 beds

2 baths

1,265 sq ft

Condo

610 HERITAGE HLS B, SOMERS, NY, 10589

Community: Heritage Hills

New Jefferson Village

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

$439,000

2 beds

1 baths

925 sq ft

Condo

15F ESSEX PL F, YORKTOWN, NY, 10598

Community: Jefferson Village

New Leisure Glen

9 BALDWIN CT 9, BROOKHAVEN, NY, 11961, Brookhaven, NY 11961

$449,000

2 beds

2 baths

1,476 sq ft

House

9 BALDWIN CT 9, BROOKHAVEN, NY, 11961

Community: Leisure Glen

New Oronoque Village

209 ACORN LN A, STRATFORD, CT, 06614, Stratford, CT 06614

$574,900

2 beds

3 baths

1,438 sq ft

Condo

209 ACORN LN A, STRATFORD, CT, 06614

Community: Oronoque Village

New Leisure Village

368 WOODBRIDGE DR A, BROOKHAVEN, NY, 119..., Brookhaven, NY 11961

$399,990

2 beds

1 baths

Condo

368 WOODBRIDGE DR A, BROOKHAVEN, NY, 119...

Community: Leisure Village

New Setauket Meadows

58 BLAIR RD 58, BROOKHAVEN, NY, 11733, Brookhaven, NY 11733

$849,999

2 beds

4 baths

1,773 sq ft

Condo

58 BLAIR RD 58, BROOKHAVEN, NY, 11733

Community: Setauket Meadows

Leisure Village

110 EXMORE CT A, BROOKHAVEN, NY, 11961, Brookhaven, NY 11961

$389,900

2 beds

1 baths

1,085 sq ft

Condo

110 EXMORE CT A, BROOKHAVEN, NY, 11961

Community: Leisure Village

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

Questions? Call us: (475) 244-9781

Regency at Prospect

156 SYCAMORE DR 156, PROSPECT, CT, 06712, Prospect, CT 06712

$559,000

2 beds

3 baths

2,067 sq ft

Condo

156 SYCAMORE DR 156, PROSPECT, CT, 06712

Community: Regency at Prospect

Jefferson Village

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

$379,000

2 beds

1 baths

935 sq ft

Condo

37 SUSSEX DR B, YORKTOWN, NY, 10598

Community: Jefferson Village

Heritage Village

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

$229,000

1 beds

1 baths

928 sq ft

Condo

149 HERITAGE VLG A, SOUTHBURY, CT, 06488

Community: Heritage Village

Heritage Hills

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

$750,000

2 beds

3 baths

1,666 sq ft

Condo

414 HERITAGE HLS A, SOMERS, NY, 10589

Community: Heritage Hills

Meadowbrook Pointe Links & Spa

48 AUGUSTA DR, BROOKHAVEN, NY, 11763, Brookhaven, NY 11763

$749,990

2 beds

4 baths

1,553 sq ft

Condo

48 AUGUSTA DR, BROOKHAVEN, NY, 11763

Community: Meadowbrook Pointe Links & Spa

Heritage Hills

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

$530,000

1 beds

2 baths

967 sq ft

Condo

582 HERITAGE HLS A, SOMERS, NY, 10589

Community: Heritage Hills

Fairfield at St. James

209 CABOT CT, SMITHTOWN, NY, 11780, Smithtown, NY 11780

$419,000

1 beds

2 baths

900 sq ft

Condo

209 CABOT CT, SMITHTOWN, NY, 11780

Community: Fairfield at St. James

Heritage Village

59 HERITAGE VLG F, SOUTHBURY, CT, 06488, Southbury, CT 06488

$219,900

2 beds

2 baths

1,308 sq ft

Condo

59 HERITAGE VLG F, SOUTHBURY, CT, 06488

Community: Heritage Village

Oronoque Village

619 ERIE LN B, STRATFORD, CT, 06614, Stratford, CT 06614

$639,000

1 beds

3 baths

1,583 sq ft

Condo

619 ERIE LN B, STRATFORD, CT, 06614

Community: Oronoque Village

The Village at Oxford Greens

1126 ST ANDREWS DR 96, OXFORD, CT, 06478, Oxford, CT 06478

$749,900

2 beds

3 baths

1,955 sq ft

Condo

1126 ST ANDREWS DR 96, OXFORD, CT, 06478

Community: The Village at Oxford Greens

Fairview at Oxford Greens

$749,900

2 beds

3 baths

1,955 sq ft

Condo

1126 ST ANDREWS DR 96, OXFORD, CT, 06478

Community: Fairview at Oxford Greens

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

Questions? Call us: (475) 244-9781

Oronoque Village

765 NYACK LN A, STRATFORD, CT, 06614, Stratford, CT 06614

$649,900

2 beds

3 baths

1,642 sq ft

Condo

765 NYACK LN A, STRATFORD, CT, 06614

Community: Oronoque Village

Jefferson Village

157 CARRIAGE CT E, YORKTOWN, NY, 10598, Yorktown, NY 10598

$324,000

1 beds

1 baths

845 sq ft

Condo

157 CARRIAGE CT E, YORKTOWN, NY, 10598

Community: Jefferson 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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130 communities

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

130 communities near Cheshire

267 homes near Cheshire

2 beds

2 baths

1,415 sq ft

Condo

3 beds

4 baths

1,726 sq ft

Condo

2 beds

2 baths

1,135 sq ft

Condo

1 beds

2 baths

949 sq ft

Condo

3 beds

3 baths

Condo

2 beds

2 baths

1,202 sq ft

Condo

2 beds

2 baths

1,427 sq ft

Condo

2 beds

2 baths

1,335 sq ft

Condo

2 beds

3 baths

1,328 sq ft

Condo

2 beds

2 baths

1,394 sq ft

Condo

1 beds

1 baths

928 sq ft

Condo

1 beds

2 baths

1,175 sq ft

Condo

2 beds

2 baths

1,663 sq ft

Condo

1 beds

2 baths

954 sq ft

Condo

2 beds

2 baths

1,412 sq ft

Condo

2 beds

2 baths

1,302 sq ft

Condo

3 beds

3 baths

2,700 sq ft

Condo

3 beds

2 baths

1,689 sq ft

Condo

1 beds

2 baths

967 sq ft

Condo

2 beds

2 baths