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

129 communities 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 - $600Ks

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

Dutchgate, Valley Stream, NY

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

The Waterways at Moriches

$400Ks - $700Ks

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

$300Ks - $400Ks

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

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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

1 2 3...4

The Gardens of Wilbraham

116 CHERRY DR # 116, WILBRAHAM, MA, 0109..., Wilbraham, MA 01095

$515,000

2 beds

2 baths

1,634 sq ft

Condo

116 CHERRY DR # 116, WILBRAHAM, MA, 0109...

Community: The Gardens of Wilbraham

The Gardens of Wilbraham

32 LODGE LN # 32, WILBRAHAM, MA, 01095, Wilbraham, MA 01095

$565,000

2 beds

2 baths

1,610 sq ft

Condo

32 LODGE LN # 32, WILBRAHAM, MA, 01095

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

Community: Glenwood Village

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712 CHAMPIONSHIP DR # 712, OXFORD, CT, 0...

Community: The Village at Oxford Greens

Fairview at Oxford Greens

$615,000

2 beds

2 baths

1,546 sq ft

Condo

712 CHAMPIONSHIP DR # 712, OXFORD, CT, 0...

Community: Fairview at Oxford Greens

Oronoque Village

133 BANNOCK LN A, STRATFORD, CT, 06614, Stratford, CT 06614

$629,900

3 beds

3 baths

1,438 sq ft

Condo

133 BANNOCK LN A, STRATFORD, CT, 06614

Community: Oronoque Village

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

Questions? Call us: (475) 244-9781

Rivington

13 MERCY ST # 13, DANBURY, CT, 06810, Danbury, CT 06810

$650,000

3 beds

3 baths

1,572 sq ft

Condo

13 MERCY ST # 13, DANBURY, CT, 06810

Community: Rivington

Heritage Village

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

$369,900

2 beds

2 baths

1,398 sq ft

Condo

865 HERITAGE VLG B, SOUTHBURY, CT, 06488

Community: Heritage Village

New Oak Meadow Estates

21 OAK MEADOW LN # 21, HARWINTON, CT, 06..., Harwinton, CT 06791

$450,000

2 beds

3 baths

2,164 sq ft

Condo

21 OAK MEADOW LN # 21, HARWINTON, CT, 06...

Community: Oak Meadow Estates

Heritage Village

568A HERITAGE VLG, SOUTHBURY, CT, 06488, Southbury, CT 06488

$409,900

2 beds

2 baths

1,432 sq ft

Condo

568A HERITAGE VLG, SOUTHBURY, CT, 06488

Community: Heritage Village

Heritage Village

25 HERITAGE CRST C, SOUTHBURY, CT, 06488, Southbury, CT 06488

$449,000

2 beds

2 baths

1,447 sq ft

Condo

25 HERITAGE CRST C, SOUTHBURY, CT, 06488

Community: Heritage Village

The Village at Oxford Greens

185 COUNTRY CLUB DR # 185, OXFORD, CT, 0..., Oxford, CT 06478

$660,000

3 beds

3 baths

2,595 sq ft

Condo

185 COUNTRY CLUB DR # 185, OXFORD, CT, 0...

Community: The Village at Oxford Greens

New Newbury Village

332 STILL WATER CIR # 332, BROOKFIELD, C..., Brookfield, CT 06804

$525,000

2 beds

2 baths

1,466 sq ft

Condo

332 STILL WATER CIR # 332, BROOKFIELD, C...

Community: Newbury Village

Oronoque Village

193 BAYFIELD LN B, STRATFORD, CT, 06614, Stratford, CT 06614

$559,000

1 beds

3 baths

1,620 sq ft

Condo

193 BAYFIELD LN B, STRATFORD, CT, 06614

Community: Oronoque Village

Oronoque Village

289 AGAWAM DR B, STRATFORD, CT, 06614, Stratford, CT 06614

$639,900

1 beds

3 baths

1,620 sq ft

Condo

289 AGAWAM DR B, STRATFORD, CT, 06614

Community: Oronoque Village

Oronoque Village

195 BAYFIELD LN A, STRATFORD, CT, 06614, Stratford, CT 06614

$549,900

1 beds

3 baths

1,575 sq ft

Condo

195 BAYFIELD LN A, STRATFORD, CT, 06614

Community: Oronoque Village

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

Questions? Call us: (475) 244-9781

Oronoque Village

35 ALGONQUIN LN D, STRATFORD, CT, 06614, Stratford, CT 06614

$399,000

1 beds

2 baths

1,300 sq ft

Condo

35 ALGONQUIN LN D, STRATFORD, CT, 06614

Community: Oronoque Village

Oronoque Village

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

$450,000

1 beds

3 baths

1,550 sq ft

Condo

375 PIUTE LN B, STRATFORD, CT, 06614

Community: Oronoque Village

Newtown Woods

433 BROOKSIDE CT 433, NEWTOWN, CT, 06470, Newtown, CT 06470

$500,000

2 beds

2 baths

1,504 sq ft

Condo

433 BROOKSIDE CT 433, NEWTOWN, CT, 06470

Community: Newtown Woods

Heritage Village

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

$380,000

3 beds

2 baths

1,716 sq ft

Condo

859 HERITAGE VLG B, SOUTHBURY, CT, 06488

Community: Heritage Village

New Oak Meadow Estates

65 OAK MEADOW LN # 65, HARWINTON, CT, 06..., Harwinton, CT 06791

$495,000

2 beds

4 baths

2,164 sq ft

Condo

65 OAK MEADOW LN # 65, HARWINTON, CT, 06...

Community: Oak Meadow Estates

Spring Lake Village

85 CLEARVIEW CT # 85, SOUTHINGTON, CT, 0..., Southington, CT 06489

$289,900

$475,000

1 beds

3 baths

1,426 sq ft

Condo

736 QUINNIPIAC LN B, STRATFORD, CT, 0661...

Community: Oronoque Village

Heritage Village

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

$263,000

2 beds

2 baths

1,308 sq ft

Condo

563 HERITAGE VLG F, SOUTHBURY, CT, 06488

Condo

902 HERITAGE VLG A, SOUTHBURY, CT, 06488

Community: Heritage Village

1 2 3 4 5…6

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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129 communities near Cheshire

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

129 communities near Cheshire

232 homes near Cheshire

2 beds

2 baths

1,634 sq ft

Condo

2 beds

2 baths

1,610 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

1,426 sq ft

Condo

2 beds

2 baths

2,195 sq ft

Condo

2 beds

2 baths

1,063 sq ft

Condo

2 beds

3 baths

1,360 sq ft

Condo

1 beds

3 baths

1,438 sq ft

Condo

1 beds

2 baths

1,175 sq ft

Condo

2 beds

2 baths

1,217 sq ft

Condo

2 beds

2 baths

1,546 sq ft

Condo

2 beds

2 baths

1,546 sq ft

Condo

3 beds

3 baths

1,438 sq ft

Condo

3 beds

3 baths

1,572 sq ft

Condo

2 beds

2 baths

1,398 sq ft

Condo

2 beds

3 baths

2,164 sq ft

Condo

2 beds

2 baths

1,432 sq ft

Condo

2 beds