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

271 homes 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

Oronoque Village

$200ks - $400ks

Oronoque Village, Stratford, CT

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

3 rating (2 reviews)

Heritage Hills

$400ks - $800ks

Heritage Hills, Somers, NY

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

Overlook

$600ks - $900ks

Overlook, Carmel, NY

New Construction | 55+ age-restricted | 300 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

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

Questions? Call us: (475) 244-9781

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

3.7 rating (3 reviews)

Greenwood Village

$100ks

Greenwood Village, Manorville, NY

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

Leisure Village

$100ks - $300ks

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

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.

Country Pointe Plainview

$700ks - $1Ms

Country Pointe Plainview, Plainview, NY

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

The Villages at Mount Sin...

$600ks

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

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

4 rating (8 reviews)

Glenwood Village

$100ks - $200ks

Glenwood Village, Riverhead, NY

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

5 rating (1 reviews)

Sunken Pond Estates

$400ks

Sunken Pond Estates, Riverhead, NY

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

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

Questions? Call us: (475) 244-9781

5 rating (1 reviews)

Westhampton Pines

$900ks - $1Ms

Westhampton Pines, Westhampton, NY

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

Fairview at Oxford Greens

$400ks - $600ks

Fairview at Oxford Greens, Oxford, CT

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

Liberty at Newtown

$300ks - $400ks

Liberty at Newtown, Newtown, CT

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

Spring Lake Village

$100ks - $200ks

Spring Lake Village, Southington, CT

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

HarborView

$800ks - $1Ms

HarborView, Port Washington, NY

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

Strathmore Gate East

$300ks

Strathmore Gate East, Coram, NY

Resale Only | 55+ age-restricted | Built 1970 - 1975 | 174 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

Dutchgate

$300ks - $500ks

Dutchgate, Valley Stream, NY

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

Stoneleigh Woods at River...

$500ks

Stoneleigh Woods at River..., Riverhead, NY

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

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

Questions? Call us: (475) 244-9781

Country Pointe Preserve

$600ks - $900ks

Country Pointe PreserveYaphank, NY

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

Vineyards at Brookfield

$400ks - $500ks

Vineyards at Brookfield, Center Moriches, NY

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

Leisure Glen

$300ks - $400ks

Leisure Glen, Ridge, NY

Resale Only | 55+ age-restricted | Built 1985 - 2010 | 646 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 Gardens of Wilbraham

$200ks - $400ks

The Gardens of Wilbraham, Wilbraham, MA

New and Resale | 55+ age-restricted | Built 2005 - present | 108 homes

3.5 rating (2 reviews)

Foxwood Village

$200ks - $400ks

Foxwood Village, Calverton, NY

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

Vineyards at Moriches

$500ks - $600ks

Vineyards at Moriches, Center Moriches, NY

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

The Coves at Melville

$500ks

The Coves at Melville, Melville, NY

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

The Summit at Bethel

$500ks - $700ks

The Summit at Bethel, Bethel, CT

Resale Only | 55+ age-restricted | Built 2010 - 2021 | 235 homes

Regency at Prospect

$300ks - $400ks

Regency at Prospect, Prospect, CT

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

Newbury Village

$400ks - $500ks

Newbury Village, Brookfield, CT

New and Resale | 55+ age-restricted | Built 2005 - present | 120 homes

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

Questions? Call us: (475) 244-9781

The Seasons at Plainview

$500ks - $600ks

The Seasons at Plainview, Plainview, NY

Resale Only | 55+ age-restricted | Built 2006 - 2007 | 134 homes

Meadow Brook Estates

$300ks - $400ks

Meadow Brook Estates, Oxford, CT

Resale Only | 55+ age-restricted | Built 2003 - 2020 | 246 homes

1 2 3...4

Glenwood Village

1661 OLD COUNTRY RD 516, RIVERHEAD, NY, ..., Riverhead, NY 11901

$419,000

2 beds

2 baths

1,624 sq ft

Manufactured Home

1661 OLD COUNTRY RD 516, RIVERHEAD, NY, ...

Community: Glenwood Village

New Pond Spring Village

111 PONDVIEW CIR 111, BEACON FALLS, CT, ..., Beacon Falls, CT 06403

$438,000

2 beds

2 baths

1,328 sq ft

Condo

111 PONDVIEW CIR 111, BEACON FALLS, CT, ...

Community: Pond Spring Village

New Country Pointe Plainview

19303 ASPENWOOD DR, OYSTER BAY, NY, 1180..., Oyster Bay, NY 11803

$1,148,000

2 beds

2 baths

1,335 sq ft

Condo

19303 ASPENWOOD DR, OYSTER BAY, NY, 1180...

Community: Country Pointe Plainview

New The Greens at Half Hollow

1125 SAVOY DR, HUNTINGTON, NY, 11747, Huntington, NY 11747

$760,000

2 beds

2 baths

1,238 sq ft

Condo

1125 SAVOY DR, HUNTINGTON, NY, 11747

Community: The Greens at Half Hollow

New Heritage Village

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

$310,000

2 beds

2 baths

1,398 sq ft

Condo

233 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 The Village at Oxford Greens

349 NIBLICK LN 349, OXFORD, CT, 06478, Oxford, CT 06478

$689,000

3 beds

2 baths

2,008 sq ft

Condo

349 NIBLICK LN 349, OXFORD, CT, 06478

Community: The Village at Oxford Greens

New The Greens at Half Hollow

363 ALTESSA BLVD, HUNTINGTON, NY, 11747, Huntington, NY 11747

$1,599,000

3 beds

3 baths

2,700 sq ft

Condo

363 ALTESSA BLVD, HUNTINGTON, NY, 11747

Community: The Greens at Half Hollow

New The Greens at Half Hollow

907 ALTESSA BLVD, HUNTINGTON, NY, 11747, Huntington, NY 11747

$749,000

2 beds

2 baths

1,186 sq ft

Condo

907 ALTESSA BLVD, HUNTINGTON, NY, 11747

Community: The Greens at Half Hollow

New Heritage Hills

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

$599,000

2 beds

2 baths

1,265 sq ft

Condo

600 HERITAGE HLS A, SOMERS, NY, 10589

Community: Heritage Hills

New HarborView

100 HARBORVIEW DR 301, NORTH HEMPSTEAD, ..., North Hempstead, NY 11050

$1,200,000

3 beds

3 baths

Condo

100 HARBORVIEW DR 301, NORTH HEMPSTEAD, ...

Community: HarborView

New Heritage Village

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

$385,000

2 beds

2 baths

1,432 sq ft

Condo

972 HERITAGE VLG B, SOUTHBURY, CT, 06488

Community: Heritage Village

New The Village at Oxford Greens

349 NIBLICK LN, OXFORD, CT, 06478, Oxford, CT 06478

$689,000

3 beds

2 baths

2,152 sq ft

349 NIBLICK LN, OXFORD, CT, 06478

Community: The Village at Oxford Greens

New Heritage Village

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

$289,900

2 beds

2 baths

1,044 sq ft

Condo

176 HERITAGE VLG D, SOUTHBURY, CT, 06488

Community: Heritage Village

New Country Pointe Plainview

55201 SPRUCE POND CIR, OYSTER BAY, NY, 1..., Oyster Bay, NY 11803

$1,599,000

2 beds

2 baths

1,989 sq ft

Condo

55201 SPRUCE POND CIR, OYSTER BAY, NY, 1...

Community: Country Pointe Plainview

New Spring Lake Village

21 HICKORY HL 21, SOUTHINGTON, CT, 06489, Southington, CT 06489

$248,000

2 beds

2 baths

1,285 sq ft

Condo

21 HICKORY HL 21, SOUTHINGTON, CT, 06489

Community: Spring Lake Village

New The Manors at The Colony Preserve

33 GREENTREE CT, BROOKHAVEN, NY, 11967, Brookhaven, NY 11967

$510,000

2 beds

2 baths

1,557 sq ft

Condo

33 GREENTREE CT, BROOKHAVEN, NY, 11967

Community: The Manors at The Colony Preserve

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

Questions? Call us: (475) 244-9781

New The Waterways at Moriches

632 WATER WAY 32, BROOKHAVEN, NY, 11955, Brookhaven, NY 11955

$799,000

2 beds

3 baths

1,874 sq ft

Condo

632 WATER WAY 32, BROOKHAVEN, NY, 11955

Community: The Waterways at Moriches

New The Seasons at Elwood

178 SUMMER CIR, HUNTINGTON, NY, 11731, Huntington, NY 11731

$1,688,000

2 beds

3 baths

2,900 sq ft

Condo

178 SUMMER CIR, HUNTINGTON, NY, 11731

Community: The Seasons at Elwood

New Vineyards at Blue Point

174 HALLEY DR, BROOKHAVEN, NY, 11772, Brookhaven, NY 11772

$829,900

2 beds

2 baths

1,928 sq ft

Condo

174 HALLEY DR, BROOKHAVEN, NY, 11772

Community: Vineyards at Blue Point

New Greenwood Village

5131 VILLAGE CIR, BROOKHAVEN, NY, 11949, Brookhaven, NY 11949

$135,000

2 beds

2 baths

987 sq ft

House

5131 VILLAGE CIR, BROOKHAVEN, NY, 11949

Community: Greenwood Village

New Meadowbrook Pointe Athletic Club & Spa

34 SHADY LN, HEMPSTEAD, NY, 11590, Hempstead, NY 11590

$877,000

2 beds

2 baths

1,319 sq ft

Condo

34 SHADY LN, HEMPSTEAD, NY, 11590

Community: Meadowbrook Pointe Athletic Club & Spa

New Fairfield at St. James

1205 GOTHAM DR, SMITHTOWN, NY, 11780, Smithtown, NY 11780

$649,000

2 beds

2 baths

948 sq ft

Condo

1205 GOTHAM DR, SMITHTOWN, NY, 11780

Community: Fairfield at St. James

New Country Pointe Preserve

118 JUNIPER LN 31, BROOKHAVEN, NY, 11980, Brookhaven, NY 11980

$865,000

2 beds

3 baths

1,998 sq ft

Condo

118 JUNIPER LN 31, BROOKHAVEN, NY, 11980

Community: Country Pointe Preserve

New The Greens at Half Hollow

727 BALFOUR PL, HUNTINGTON, NY, 11747, Huntington, NY 11747

$1,175,000

3 beds

3 baths

2,500 sq ft

Condo

727 BALFOUR PL, HUNTINGTON, NY, 11747

Community: The Greens at Half Hollow

New Heritage Hills

34 HERITAGE HLS C, SOMERS, NY, 10589, Somers, NY 10589

$625,000

2 beds

3 baths

1,545 sq ft

Condo

34 HERITAGE HLS C, SOMERS, NY, 10589

Community: Heritage Hills

New Vineyards at Blue Point

32 AVERY WAY, BROOKHAVEN, NY, 11772, Brookhaven, NY 11772

$799,000

2 beds

3 baths

2,168 sq ft

Condo

32 AVERY WAY, BROOKHAVEN, NY, 11772

Community: Vineyards at Blue Point

New Fairfield at St. James

606 FLAIR CT, SMITHTOWN, NY, 11780, Smithtown, NY 11780

$429,000

1 beds

1 baths

752 sq ft

Condo

606 FLAIR CT, SMITHTOWN, NY, 11780

Community: Fairfield at St. James

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

Questions? Call us: (475) 244-9781

New Oronoque Village

46 BUCKSKIN LN A, STRATFORD, CT, 06614, Stratford, CT 06614

$559,900

1 beds

2 baths

1,375 sq ft

Condo

46 BUCKSKIN LN A, STRATFORD, CT, 06614

Community: Oronoque Village

New Vineyards at Moriches

20 EMILIE DR, BROOKHAVEN, NY, 11934, Brookhaven, NY 11934

$759,000

2 beds

3 baths

1,984 sq ft

Condo

20 EMILIE DR, BROOKHAVEN, NY, 11934

Community: Vineyards at Moriches

New Leisure Glen

187 GLEN DR, BROOKHAVEN, NY, 11961, Brookhaven, NY 11961

$525,000

2 beds

2 baths

1,451 sq ft

Condo

187 GLEN DR, BROOKHAVEN, NY, 11961

Community: Leisure Glen

New The Waterways at Moriches

216 RIVER DR, BROOKHAVEN, NY, 11955, Brookhaven, NY 11955

$510,000

2 beds

2 baths

1,544 sq ft

Condo

216 RIVER DR, BROOKHAVEN, NY, 11955

Community: The Waterways at Moriches

New The Retreat at Carmel

4 REESE CT, CARMEL, NY, 10512, Carmel, NY 10512

$699,000

2 beds

2 baths

1,979 sq ft

House

4 REESE CT, CARMEL, NY, 10512

Community: The Retreat at Carmel

New Heritage Hills

128 HERITAGE HILLS DR B, SOMERS, NY, 105..., Somers, NY 10589

$450,000

1 beds

1 baths

955 sq ft

Condo

128 HERITAGE HILLS DR B, SOMERS, NY, 105...

Community: Heritage Hills

New Heritage Hills

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

$649,000

3 beds

2 baths

1,689 sq ft

Condo

156 HERITAGE HLS A, SOMERS, NY, 10589

Community: Heritage Hills

New Heritage Village

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

$275,000

2 beds

2 baths

1,432 sq ft

Condo

874 HERITAGE VLG A, SOUTHBURY, CT, 06488

Community: Heritage Village

Greenwood Village

16 DOGWOOD LN, BROOKHAVEN, NY, 11949, Brookhaven, NY 11949

$299,999

2 beds

2 baths

1,288 sq ft

Condo

16 DOGWOOD LN, BROOKHAVEN, NY, 11949

Community: Greenwood Village

Vineyards at Moriches

27 EMILIE DR, BROOKHAVEN, NY, 11934, Brookhaven, NY 11934

$785,000

2 beds

3 baths

2,335 sq ft

Condo

27 EMILIE DR, BROOKHAVEN, NY, 11934

Community: Vineyards at Moriches

The Gardens of Wilbraham

137 CHERRY DR 137, WILBRAHAM, MA, 01095, Wilbraham, MA 01095

$400,000

2 beds

2 baths

1,241 sq ft

Condo

137 CHERRY DR 137, WILBRAHAM, MA, 01095

Community: The Gardens of Wilbraham

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

Questions? Call us: (475) 244-9781

Rivington

11 MERCY ST 11, DANBURY, CT, 06810, Danbury, CT 06810

$630,000

2 beds

4 baths

1,572 sq ft

11 MERCY ST 11, DANBURY, CT, 06810

Community: Rivington

Heritage Village

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

$399,900

2 beds

2 baths

1,398 sq ft

Condo

701 HERITAGE VLG A, SOUTHBURY, CT, 06488

Community: Heritage Village

1 2 3 4 5 6…7

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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271 homes

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

131 communities near Cheshire

271 homes near Cheshire

2 beds

2 baths

1,624 sq ft

Manufactured Home

2 beds

2 baths

1,328 sq ft

Condo

2 beds

2 baths

1,335 sq ft

Condo

2 beds

2 baths

1,238 sq ft

Condo

2 beds

2 baths

1,398 sq ft

Condo

3 beds

2 baths

2,008 sq ft

Condo

3 beds

3 baths

2,700 sq ft

Condo

2 beds

2 baths

1,186 sq ft

Condo

2 beds

2 baths

1,265 sq ft

Condo

3 beds

3 baths

Condo

2 beds

2 baths

1,432 sq ft

Condo

3 beds

2 baths

2,152 sq ft

2 beds

2 baths

1,044 sq ft

Condo

2 beds

2 baths

1,989 sq ft

Condo

2 beds

2 baths

1,285 sq ft

Condo

2 beds

2 baths

1,557 sq ft

Condo

2 beds

3 baths

1,874 sq ft

Condo

2 beds

3 baths

2,900 sq ft

Condo

2 beds

2 baths

1,928 sq ft

Condo

2 beds

2 baths

987 sq ft