Cheshire, CT 55+ active adult communities & homes for sale - Page 4

292 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

3 rating (2 reviews)

Heritage Hills

$400ks - $800ks

Heritage Hills, Somers, NY

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

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

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

The Waterways at Moriches

$300ks - $600ks

The Waterways at Moriches, Moriches, NY

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

3.7 rating (3 reviews)

Greenwood Village

$100ks

Greenwood Village, Manorville, NY

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

Overlook

$600ks - $900ks

Overlook, Carmel, NY

New Construction | 55+ age-restricted | 300 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

Leisure Village

$100ks - $300ks

Leisure Village, Ridge, NY

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

Rivington

$300ks - $900ks

Rivington, Danbury, CT

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

Fairview at Oxford Greens

$400ks - $600ks

Fairview at Oxford Greens, Oxford, CT

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

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

Questions? Call us: (475) 244-9781

Stoneleigh Woods at River...

$500ks

Stoneleigh Woods at River..., Riverhead, NY

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

Leisure Knoll

$200ks - $400ks

Leisure Knoll, Ridge, NY

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

Leisure Glen

$300ks - $400ks

Leisure Glen, Ridge, NY

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

HarborView

$600ks - $1Ms

HarborView, Port Washington, NY

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

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

5 rating (1 reviews)

Newtown Woods

$300ks - $500ks

Newtown Woods, Newtown, CT

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

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

Vineyards at Brookfield

$400ks - $500ks

Vineyards at Brookfield, Center Moriches, NY

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

Liberty at Newtown

$300ks - $400ks

Liberty at Newtown, Newtown, CT

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

Country Pointe Preserve

$600ks - $900ks

Country Pointe PreserveYaphank, NY

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

Vineyards at Moriches

$500ks - $600ks

Vineyards at Moriches, Center Moriches, NY

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

Setauket Meadows

$500ks - $600ks

Setauket Meadows, Setauket, NY

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

3.5 rating (2 reviews)

Foxwood Village

$200ks - $400ks

Foxwood Village, Calverton, NY

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

Saddle Lakes

$400ks - $500ks

Saddle Lakes, Riverhead, NY

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

The Powder Forest Homes

$500ks - $700ks

The Powder Forest Homes, Simsbury, CT

Resale Only | 55+ age-restricted | Built 2006 - 2016 | 182 homes

Baldwin Station

$400ks

Baldwin Station, Milford, CT

Resale Only | 55+ age-restricted | Built 2001 - 2003 | 82 homes

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

Questions? Call us: (475) 244-9781

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

The Summit at Bethel

$500ks - $700ks

The Summit at Bethel, Bethel, CT

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

1 2 3...4

The Village at Oxford Greens

1129 ST ANDREWS DR 49, OXFORD, CT, 06478, Oxford, CT 06478

$709,555

2 beds

3 baths

2,454 sq ft

Condo

1129 ST ANDREWS DR 49, OXFORD, CT, 06478

Community: The Village at Oxford Greens

Fairview at Oxford Greens

$709,555

2 beds

3 baths

2,454 sq ft

Condo

1129 ST ANDREWS DR 49, OXFORD, CT, 06478

Community: Fairview at Oxford Greens

Fairview at Oxford Greens

1111 ST ANDREWS DR 16, OXFORD, CT, 06478, Oxford, CT 06478

$778,585

2 beds

3 baths

2,454 sq ft

Condo

1111 ST ANDREWS DR 16, OXFORD, CT, 06478

Community: Fairview at Oxford Greens

The Village at Oxford Greens

$778,585

2 beds

3 baths

2,454 sq ft

Condo

1111 ST ANDREWS DR 16, OXFORD, CT, 06478

Community: The Village at Oxford Greens

Fairview at Oxford Greens

1138 ST ANDREWS DR 90, OXFORD, CT, 06478, Oxford, CT 06478

$754,150

2 beds

3 baths

1,955 sq ft

Condo

1138 ST ANDREWS DR 90, 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

The Village at Oxford Greens

$754,150

2 beds

3 baths

1,955 sq ft

Condo

1138 ST ANDREWS DR 90, OXFORD, CT, 06478

Community: The Village at Oxford Greens

Fairfield at St. James

302 BENTLEY CT, SMITHTOWN, NY, 11780, Smithtown, NY 11780

$499,000

2 beds

2 baths

1,067 sq ft

Condo

302 BENTLEY CT, SMITHTOWN, NY, 11780

Community: Fairfield at St. James

Oronoque Village

372 PIUTE LN B, STRATFORD, CT, 06614, Stratford, CT 06614

$384,900

1 beds

2 baths

1,375 sq ft

Condo

372 PIUTE LN B, STRATFORD, CT, 06614

Community: Oronoque Village

Encore Atlantic Shores

63 ENCORE BLVD, BROOKHAVEN, NY, 11941, Brookhaven, NY 11941

$918,000

2 beds

3 baths

2,769 sq ft

Condo

63 ENCORE BLVD, BROOKHAVEN, NY, 11941

Community: Encore Atlantic Shores

Heritage Hills

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

$699,000

2 beds

2 baths

1,470 sq ft

Condo

371 HERITAGE HLS A, SOMERS, NY, 10589

Community: Heritage Hills

Jefferson Village

90 MOLLY PITCHER LN F, YORKTOWN, NY, 105..., Yorktown, NY 10598

$339,900

1 beds

1 baths

800 sq ft

Condo

90 MOLLY PITCHER LN F, YORKTOWN, NY, 105...

Community: Jefferson Village

Eagles Walk at East Quogue

1204 AERIE WAY 1204, SOUTHAMPTON, NY, 11..., Southampton, NY 11942

$565,000

2 beds

2 baths

1,341 sq ft

Condo

1204 AERIE WAY 1204, SOUTHAMPTON, NY, 11...

Community: Eagles Walk at East Quogue

Jefferson Village

149 FLINTLOCK WAY E, YORKTOWN, NY, 10598, Yorktown, NY 10598

$375,000

1 beds

1 baths

853 sq ft

Condo

149 FLINTLOCK WAY E, YORKTOWN, NY, 10598

Community: Jefferson Village

Heritage Hills

241 HERITAGE HLS D, SOMERS, NY, 10589, Somers, NY 10589

$499,900

2 beds

2 baths

1,138 sq ft

Condo

241 HERITAGE HLS D, SOMERS, NY, 10589

Community: Heritage Hills

Encore Atlantic Shores

216 SONATA CT, BROOKHAVEN, NY, 11941, Brookhaven, NY 11941

$899,000

2 beds

3 baths

2,439 sq ft

Condo

216 SONATA CT, BROOKHAVEN, NY, 11941

Community: Encore Atlantic Shores

The Waterways at Moriches

132 CAPTAINS CT, BROOKHAVEN, NY, 11955, Brookhaven, NY 11955

$550,000

2 beds

2 baths

1,544 sq ft

Condo

132 CAPTAINS CT, BROOKHAVEN, NY, 11955

Community: The Waterways at Moriches

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

Questions? Call us: (475) 244-9781

Vineyards at Blue Point

37 HALLEY DR 17, BROOKHAVEN, NY, 11772, Brookhaven, NY 11772

$660,000

2 beds

2 baths

1,220 sq ft

Condo

37 HALLEY DR 17, BROOKHAVEN, NY, 11772

Community: Vineyards at Blue Point

Newtown Woods

1227 BROOKSIDE CT 1227, NEWTOWN, CT, 064..., Newtown, CT 06470

$500,000

2 beds

2 baths

1,483 sq ft

Condo

1227 BROOKSIDE CT 1227, NEWTOWN, CT, 064...

Community: Newtown Woods

Newtown Woods

23 WOODS LN 23, NEWTOWN, CT, 06470, Newtown, CT 06470

$600,000

2 beds

3 baths

2,073 sq ft

Condo

23 WOODS LN 23, NEWTOWN, CT, 06470

Community: Newtown Woods

HarborView

123 LINKS CT, NORTH HEMPSTEAD, NY, 11050, North Hempstead, NY 11050

$1,299,000

3 beds

3 baths

2,160 sq ft

Condo

123 LINKS CT, NORTH HEMPSTEAD, NY, 11050

Community: HarborView

Heritage Village

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

$342,500

2 beds

2 baths

1,398 sq ft

Condo

581 HERITAGE VLG A, SOUTHBURY, CT, 06488

Community: Heritage Village

Jefferson Village

56 KIRBY CLOSE B, YORKTOWN, NY, 10598, Yorktown, NY 10598

$474,500

2 beds

2 baths

970 sq ft

Condo

56 KIRBY CLOSE B, YORKTOWN, NY, 10598

Community: Jefferson Village

Windcrest East

5 GREEN ASH ST, RIVERHEAD, NY, 11933, Riverhead, NY 11933

$775,000

3 beds

3 baths

2,449 sq ft

House

5 GREEN ASH ST, RIVERHEAD, NY, 11933

Community: Windcrest East

Oronoque Village

383 SEQUOIA LN B, STRATFORD, CT, 06614, Stratford, CT 06614

$485,000

1 beds

3 baths

1,360 sq ft

Condo

383 SEQUOIA LN B, STRATFORD, CT, 06614

Community: Oronoque Village

Heritage Village

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

$349,900

2 beds

2 baths

1,398 sq ft

Condo

895 HERITAGE VLG A, SOUTHBURY, CT, 06488

Community: Heritage Village

Stoneleigh Woods at Riverhead

159 STONELEIGH DR, RIVERHEAD, NY, 11901, Riverhead, NY 11901

$674,999

2 beds

3 baths

2,172 sq ft

Condo

159 STONELEIGH DR, RIVERHEAD, NY, 11901

Community: Stoneleigh Woods at Riverhead

Heritage Village

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

$389,900

2 beds

2 baths

1,432 sq ft

Condo

16 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

Spring Lake Village

626 OVERLOOK PATH 626, SOUTHINGTON, CT, ..., Southington, CT 06489

$350,000

2 beds

2 baths

1,230 sq ft

Condo

626 OVERLOOK PATH 626, SOUTHINGTON, CT, ...

Community: Spring Lake Village

Heritage Village

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

$299,900

2 beds

2 baths

1,032 sq ft

Condo

38 HERITAGE VLG A, SOUTHBURY, CT, 06488

Community: Heritage Village

Oronoque Village

407 MONTAUK LN B, STRATFORD, CT, 06614, Stratford, CT 06614

$439,000

1 beds

2 baths

1,360 sq ft

Condo

407 MONTAUK LN B, STRATFORD, CT, 06614

Community: Oronoque Village

Leisure Village

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

$394,990

2 beds

1 baths

Condo

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

Community: Leisure Village

Baldwin Station

15 JASMINE CIR 15, MILFORD, CT, 06461, Milford, CT 06461

$599,000

2 beds

3 baths

2,331 sq ft

Condo

15 JASMINE CIR 15, MILFORD, CT, 06461

Community: Baldwin Station

The Village at Oxford Greens

941 MACKENZIE LN 941, OXFORD, CT, 06478, Oxford, CT 06478

$699,900

2 beds

2 baths

1,682 sq ft

941 MACKENZIE LN 941, OXFORD, CT, 06478

Community: The Village at Oxford Greens

Fairview at Oxford Greens

$699,900

2 beds

2 baths

1,682 sq ft

941 MACKENZIE LN 941, OXFORD, CT, 06478

Community: Fairview at Oxford Greens

Snug Harbor

58 HARBOR RD, BABYLON, NY, 11701, Babylon, NY 11701

$495,000

1 beds

1 baths

727 sq ft

Condo

58 HARBOR RD, BABYLON, NY, 11701

Community: Snug Harbor

Rivington

64 WARRINGTON ROUND 64, DANBURY, CT, 068..., Danbury, CT 06810

$615,000

3 beds

3 baths

1,600 sq ft

Condo

64 WARRINGTON ROUND 64, DANBURY, CT, 068...

Community: Rivington

Glenwood Village

1661 OLD COUNTRY RD 156D, RIVERHEAD, NY,..., Riverhead, NY 11901

$469,000

2 beds

2 baths

1,500 sq ft

Manufactured Home

1661 OLD COUNTRY RD 156D, RIVERHEAD, NY,...

Community: Glenwood Village

Meadowbrook Pointe Athletic Club & Spa

348 TROTTING LN, HEMPSTEAD, NY, 11590, Hempstead, NY 11590

$889,000

2 beds

2 baths

1,319 sq ft

Condo

348 TROTTING LN, HEMPSTEAD, NY, 11590

Community: Meadowbrook Pointe Athletic Club & Spa

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

Questions? Call us: (475) 244-9781

Heritage Village

1008 HERITAGE VLG A, SOUTHBURY, CT, 0648..., Southbury, CT 06488

$518,000

3 beds

2 baths

1,716 sq ft

Condo

1008 HERITAGE VLG A, SOUTHBURY, CT, 0648...

Community: Heritage Village

Leisure Village

66 ENFIELD CT B, BROOKHAVEN, NY, 11961, Brookhaven, NY 11961

$359,900

2 beds

1 baths

1,085 sq ft

Condo

66 ENFIELD CT B, BROOKHAVEN, NY, 11961

Community: Leisure Village

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.

Want more information about active adult communities around Cheshire?

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292 homes

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Cheshire, CT 55+ active adult communities & homes for sale - Page 4

132 communities near Cheshire

292 homes near Cheshire

2 beds

3 baths

2,454 sq ft

Condo

2 beds

3 baths

2,454 sq ft

Condo

2 beds

3 baths

2,454 sq ft

Condo

2 beds

3 baths

2,454 sq ft

Condo

2 beds

3 baths

1,955 sq ft

Condo

2 beds

3 baths

1,955 sq ft

Condo

2 beds

2 baths

1,067 sq ft

Condo

1 beds

2 baths

1,375 sq ft

Condo

2 beds

3 baths

2,769 sq ft

Condo

2 beds

2 baths

1,470 sq ft

Condo

1 beds

1 baths

800 sq ft

Condo

2 beds

2 baths

1,341 sq ft

Condo

1 beds

1 baths

853 sq ft

Condo

2 beds

2 baths

1,138 sq ft

Condo

2 beds

3 baths

2,439 sq ft

Condo

2 beds

2 baths

1,544 sq ft

Condo

2 beds

2 baths

1,220 sq ft

Condo

2 beds

2 baths

1,483 sq ft

Condo

2 beds

3 baths

2,073 sq ft

Condo

3 beds