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

128 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

No reviews yet

Leisure Village

$200Ks - $500Ks

Leisure Village, Ridge, NY

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

No reviews yet

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

No reviews yet

Rivington

$400Ks - $500Ks

Rivington, Danbury, CT

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

4 rating (1 reviews)

Jefferson Village

$300Ks - $600Ks

Jefferson Village, Yorktown Heights, NY

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

No reviews yet

Oronoque Village

$200Ks - $600Ks

Oronoque Village, Stratford, CT

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

No reviews yet

The Village at Oxford Gre...

$500Ks - $700Ks

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

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

No reviews yet

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.

No reviews yet

Leisure Knoll

$300Ks - $500Ks

Leisure Knoll, Ridge, NY

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

No reviews yet

Country Pointe Plainview

$1Ms - $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

No reviews yet

Leisure Glen

$400Ks - $400Ks

Leisure Glen, Ridge, NY

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

No reviews yet

Spring Lake Village

$200Ks - $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

No reviews yet

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

No reviews yet

Regency at Prospect

$300Ks - $500Ks

Regency at Prospect, Prospect, CT

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

No reviews yet

Dutchgate

$400Ks - $400Ks

Dutchgate, Valley Stream, NY

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

No reviews yet

The Waterways at Moriches

$400Ks - $700Ks

The Waterways at Moriches, Moriches, NY

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

No reviews yet

The Retreat at Carmel

$400Ks - $600Ks

The Retreat at Carmel, Carmel, NY

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

No reviews yet

Overlook

$600Ks - $900Ks

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 - $500Ks

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

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

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

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 - $800Ks

Vineyards at Blue Point, Blue Point, NY

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

No reviews yet

HarborView

$900Ks - $1Ms

HarborView, Port Washington, NY

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

No reviews yet

The Club at Melville

$500Ks - $500Ks

The Club at Melville, Melville, NY

Resale Only | 55+ age-restricted | Built 2015 - 2017 | 261 homes

No reviews yet

The Seasons at Elwood

$800Ks - $900Ks

The Seasons at Elwood, East Northport, NY

Resale Only | 55+ age-restricted | Built 2018 - 2020 | 256 homes

No reviews yet

Meadow Brook Estates

$500Ks - $500Ks

Meadow Brook Estates, Oxford, CT

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

5 rating (1 reviews)

Encore Atlantic Shores

$600Ks - $900Ks

Encore Atlantic Shores, Eastport, NY

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

No reviews yet

The Summit at Bethel

$600Ks - $600Ks

The Summit at Bethel, Bethel, CT

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

4.9 rating (14 reviews)

Chatfield Farms

$600Ks - $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

No reviews yet

Woodridge Strathmore Terr...

$400Ks - $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

No reviews yet

Saddle Lakes

$400Ks - $400Ks

Saddle Lakes, Riverhead, NY

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

No reviews yet

Country Village Estates

$300Ks - $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

$539,000

2 beds

2 baths

1,634 sq ft

Condo

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

416 CENTER MEADOW LN # 416, DANBURY, CT,...

Community: Rivington

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

Questions? Call us: (475) 244-9781

Oronoque Village

638 ONONDAGA LN A, STRATFORD, CT, 06614, Stratford, CT 06614

$399,000

2 beds

3 baths

2,071 sq ft

Condo

638 ONONDAGA LN A, STRATFORD, CT, 06614

Community: Oronoque Village

Oronoque Village

408 MONTAUK LN A, STRATFORD, CT, 06614, Stratford, CT 06614

$425,000

1 beds

2 baths

1,118 sq ft

Condo

408 MONTAUK LN A, STRATFORD, CT, 06614

Community: Oronoque Village

Heritage Village

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

$369,900

2 beds

2 baths

1,398 sq ft

Condo

643 HERITAGE VLG A, SOUTHBURY, CT, 06488

Community: Heritage Village

Heritage Village

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

$299,900

2 beds

2 baths

1,432 sq ft

Condo

132 HERITAGE VLG A, SOUTHBURY, CT, 06488

Community: Heritage Village

Park Glen

15 HARMONY TRL # 15, NEW MILFORD, CT, 06..., New Milford, CT 06776

$699,900

2 beds

4 baths

2,720 sq ft

Condo

15 HARMONY TRL # 15, NEW MILFORD, CT, 06...

Community: Park Glen

Newbury Village

21 GREAT HERON LN # 21, BROOKFIELD, CT, ..., Brookfield, CT 06804

$720,000

3 beds

4 baths

2,644 sq ft

Condo

21 GREAT HERON LN # 21, BROOKFIELD, CT, ...

Community: Newbury Village

Heritage Village

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

$309,000

2 beds

2 baths

1,432 sq ft

Condo

919 HERITAGE VLG B, SOUTHBURY, CT, 06488

Community: Heritage Village

Oronoque Village

445 NORTH TRL A, STRATFORD, CT, 06614, Stratford, CT 06614

$449,900

1 beds

3 baths

1,620 sq ft

Condo

445 NORTH TRL A, STRATFORD, CT, 06614

Community: Oronoque Village

New Long Hill Village

17 RAINBOW DR, TRUMBULL, CT, 06611, Trumbull, CT 06611

$484,900

2 beds

2 baths

1,370 sq ft

Condo

17 RAINBOW DR, TRUMBULL, CT, 06611

Community: Long Hill Village

New Fairview at Oxford Greens

1121 ST ANDREWS DR 45, OXFORD, CT, 06478, Oxford, CT 06478

$709,900

2 beds

3 baths

1,955 sq ft

Condo

1121 ST ANDREWS DR 45, 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

New The Village at Oxford Greens

$709,900

2 beds

3 baths

1,955 sq ft

Condo

1121 ST ANDREWS DR 45, OXFORD, CT, 06478

Community: The Village at Oxford Greens

New Fairview at Oxford Greens

1119 ST ANDREWS DR 44, OXFORD, CT, 06478, Oxford, CT 06478

$649,900

2 beds

3 baths

2,454 sq ft

Condo

1119 ST ANDREWS DR 44, OXFORD, CT, 06478

Community: Fairview at Oxford Greens

New The Village at Oxford Greens

$649,900

2 beds

3 baths

2,454 sq ft

Condo

1119 ST ANDREWS DR 44, OXFORD, CT, 06478

Community: The Village at Oxford Greens

New Fairview at Oxford Greens

1117 ST ANDREWS DR 43, OXFORD, CT, 06478, Oxford, CT 06478

$699,900

2 beds

3 baths

2,536 sq ft

Condo

Community: Fairview at Oxford Greens

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

Questions? Call us: (475) 244-9781

New The Village at Oxford Greens

$729,900

2 beds

3 baths

1,955 sq ft

Condo

1130 ST ANDREWS DR 94, OXFORD, CT, 06478

Community: The Village at Oxford Greens

New The Village at Oxford Greens

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

$699,900

2 beds

3 baths

2,454 sq ft

Condo

1111 ST ANDREWS DR 16, OXFORD, CT, 06478

Community: The Village at Oxford Greens

New Fairview at Oxford Greens

$699,900

2 beds

3 baths

2,454 sq ft

Condo

1111 ST ANDREWS DR 16, OXFORD, CT, 06478

Community: Fairview at Oxford Greens

New The Village at Oxford Greens

1132 ST ANDREWS DR 93, OXFORD, CT, 06478, Oxford, CT 06478

$719,900

2 beds

3 baths

2,536 sq ft

Condo

1132 ST ANDREWS DR 93, OXFORD, CT, 06478

Community: The Village at Oxford Greens

New Fairview at Oxford Greens

$719,900

2 beds

3 baths

2,536 sq ft

Condo

1132 ST ANDREWS DR 93, OXFORD, CT, 06478

Community: Fairview at Oxford Greens

Fairview at Oxford Greens

1097 SAINT ANDREWS DR LOT 9, OXFORD, CT,..., Oxford, CT 06478

$773,625

2 beds

3 baths

2,536 sq ft

Condo

Condo

488 COMMANCHE LN A, STRATFORD, CT, 06614

Community: Oronoque Village

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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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Want to learn more about 55+ communities in Cheshire?

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128 communities near Cheshire

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

128 communities near Cheshire

294 homes near Cheshire

2 beds

2 baths

1,634 sq ft

Condo

1 beds

2 baths

1,438 sq ft

Condo

2 beds

2 baths

1,432 sq ft

Condo

2 beds

2 baths

1,308 sq ft

Condo

2 beds

2 baths

1,312 sq ft

Condo

2 beds

3 baths

2,071 sq ft

Condo

1 beds

2 baths

1,118 sq ft

Condo

2 beds

2 baths

1,398 sq ft

Condo

2 beds

2 baths

1,432 sq ft

Condo

2 beds

4 baths

2,720 sq ft

Condo

3 beds

4 baths

2,644 sq ft

Condo

2 beds

2 baths

1,432 sq ft

Condo

1 beds

3 baths

1,620 sq ft

Condo

2 beds

2 baths

1,370 sq ft

Condo

2 beds

3 baths

1,955 sq ft

Condo

2 beds

3 baths

1,955 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

2,536 sq ft

Condo

2 beds