Cheshire, CT 55+ active adult communities & homes for sale - Page 2

129 communities near Cheshire

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Granite Woods

$600Ks - $700Ks

Granite Woods, Middlebury, CT

New Construction | 55+ age-restricted | Built 2020 - present | 24 homes

Strathmore Gate East

$300Ks - $400Ks

Strathmore Gate East, Coram, NY

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

South Pond Village

$200Ks - $400Ks

South Pond Village, Bloomfield, CT

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

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Dutchgate

$400Ks - $500Ks

Dutchgate, Valley Stream, NY

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

The Seasons at Plainview

$600Ks - $700Ks

The Seasons at Plainview, Plainview, NY

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

Country Village Estates

$400Ks

Country Village Estates, Coram, NY

Resale Only | 55+ age-restricted | Built 1993 - 2001 | 195 homes

Village Estates

$400Ks - $500Ks

Village Estates, Amityville, NY

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

The Gardens of Wilbraham

$500Ks

The Gardens of Wilbraham, Wilbraham, MA

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

Read the Ultimate 55+ Rental Guide Thinking about renting in a 55+ active adult community? Our free guide has all the must-know info and practical tips to help you navigate 55+ renting and find your ideal next home in a 55+ community.

Snug Harbor

$600Ks - $700Ks

Snug Harbor, Amityville, NY

Resale Only | 55+ age-restricted | Built 1970 - 1974 | 176 homes

The Coves at Melville

$500Ks

The Coves at Melville, Melville, NY

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

Evergreen

$500Ks

Evergreen, Cromwell, CT

New and Resale | 55+ age-restricted | Built 2005 - present | 52 homes

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Questions? Call us: (475) 244-9781

HarborView

$900Ks - $1Ms

HarborView, Port Washington, NY

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

Bartlett Hill

$500Ks

Bartlett Hill, Portland, CT

Resale Only | 55+ age-restricted | Built 2005 - 2011 | 82 homes

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

Questions? Call us: (475) 244-9781

Baldwin Station

$400Ks

Baldwin Station, Milford, CT

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

Oak Meadow Estates

$400Ks

Oak Meadow Estates, Torrington, CT

New and Resale | 55+ age-restricted | Built 2013 - present | 31 homes

The Bel Aire at East Mead...

$400Ks

The Bel Aire at East Mead..., East Meadow, NY

Resale Only | 55+ age-restricted | Built 2004 - 2005 | 95 homes

Harbor View Estates

$400Ks - $600Ks

Harbor View Estates, Copiague, NY

New Construction | 55+ age-restricted | Built 2017 - 2018 | 40 homes

The Seasons at Elwood

$800Ks - $900Ks

The Seasons at Elwood, East Northport, NY

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

Jessup's Landing

$1Ms

Jessup's Landing, Quogue, NY

New and Resale | 55+ age-restricted | Built 2009 - 2016 | 31 homes

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

Questions? Call us: (475) 244-9781

Villas at Seminary Hill

$400Ks

Villas at Seminary Hill, Carmel, NY

New Construction | 55+ age-restricted | Built 2018 - present | 50 homes

Meadowbrooke Pointe East ...

$700Ks - $800Ks

Meadowbrooke Pointe East ..., East Meadow, NY

New Construction | 62+ age-restricted | Built 2019 - present | 104 homes

Hidden Harbor Estates

$500Ks - $600Ks

Hidden Harbor Estates, Copiague, NY

Resale Only | 55+ age-restricted | Built 2010 - 2015 | 38 homes

Vineyards at Brookfield

$700Ks

Vineyards at Brookfield, Center Moriches, NY

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

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

Questions? Call us: (475) 244-9781

The Vineyards at Mount Si...

$800Ks - $1Ms

The Vineyards at Mount Si..., Mount Sinai, NY

New Construction | 55+ age-restricted | Built 2020 - present | 91 homes

The Pines at Bohemia

$400Ks - $500Ks

The Pines at Bohemia, Bohemia, NY

New Construction | 55+ age-restricted | Built 2019 - present | 20 homes

The Polo Club at Islandia

$600Ks

The Polo Club at Islandia, Islandia, NY

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

Stratford Park

$900Ks

Stratford Park, Melville, NY

Resale Only | 55+ age-restricted | Built 2011 - 2013 | 36 homes

The Bridges at Oxford Gre...

$600Ks

The Bridges at Oxford Gre..., Oxford, CT

New Construction | 55+ age-restricted | Built 2025 - present | 99 homes

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

Questions? Call us: (475) 244-9781

North Woods of Colchester

$500Ks

North Woods of Colchester, Colchester, CT

New and Resale | 55+ age-restricted | Built 2007 - present | 140 homes

Applegate Estates

$500Ks - $400Ks

Applegate Estates, Southington, CT

New and Resale | 55+ age-restricted | Built 2010 - 2025 | 94 homes

Bidwell Village

$300Ks - $400Ks

Bidwell Village, Coventry, CT

New Construction | 55+ age-restricted | Built 2020 - present | 37 homes

Cobblestone Court

$400Ks - $500Ks

Cobblestone Court, Essex, CT

New and Resale | 55+ age-restricted | Built 2017 - present | 8 homes

Regency at Prospect

$400Ks - $500Ks

Regency at Prospect, Prospect, CT

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

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

Questions? Call us: (475) 244-9781

5 rating (2 reviews)

Benson Woods

$400Ks - $600Ks

Benson Woods, Middlebury, CT

New and Resale | 55+ age-restricted | Built 2004 - present | 79 homes

Newbury Village

$500Ks - $600Ks

Newbury Village, Brookfield, CT

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

Clockmaker's Hill

$100Ks

Clockmaker's Hill, Winsted, CT

Resale Only | 55+ age-restricted | Built 2005 - 2014 | 38 homes

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

Questions? Call us: (475) 244-9781

The Village at Buckingham

$500Ks - $600Ks

The Village at Buckingham, Avon, CT

Resale Only | 55+ age-restricted | Built 2002 - 2006 | 56 homes

Sonoma Woods

$300Ks

Sonoma Woods, Middletown, CT

Resale Only | 55+ age-restricted | Built 2005 - 2015 | 68 homes

1 2 3...4

Regency at Woodbridge

5 WHISPER RIDGE WAY # 49, WOODBRIDGE, CT..., Woodbridge, CT 06525

$749,000

3 beds

3 baths

Condo

5 WHISPER RIDGE WAY # 49, WOODBRIDGE, CT...

Community: Regency at Woodbridge

Regency at Woodbridge

5 EDGEWOOD WAY # 25, WOODBRIDGE, CT, 065..., Woodbridge, CT 06525

$649,000

3 beds

3 baths

Condo

5 EDGEWOOD WAY # 25, WOODBRIDGE, CT, 065...

418 WEYMOUTH CT B, RIDGE, NY, 11961

Community: Leisure Village

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

Questions? Call us: (475) 244-9781

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Questions? Call us: (475) 244-9781

The Waterways at Moriches

554 MIRROR POND CT, MORICHES, NY, 11955, Moriches, NY 11955

$525,000

2 beds

2 baths

1,497 sq ft

Condo

554 MIRROR POND CT, MORICHES, NY, 11955

Community: The Waterways at Moriches

Oronoque Village

446 HAMMERSTONE LN B, STRATFORD, CT, 066..., Stratford, CT 06614

$635,000

3 beds

3 baths

1,426 sq ft

Condo

446 HAMMERSTONE LN B, STRATFORD, CT, 066...

Community: Oronoque Village

Heritage Hills

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

$475,000

2 beds

2 baths

1,205 sq ft

Condo

182 HERITAGE HLS A, SOMERS, NY, 10589

Community: Heritage Hills

Oronoque Village

151 SOUTH TRL B, STRATFORD, CT, 06614, Stratford, CT 06614

$480,000

1 beds

3 baths

1,426 sq ft

Condo

151 SOUTH TRL B, STRATFORD, CT, 06614

Community: Oronoque Village

Breton Hills

710 BRETON WAY # 710, GLEN COVE, NY, 115..., Glen Cove, NY 11542

$679,000

2 beds

2 baths

1,430 sq ft

Condo

710 BRETON WAY # 710, GLEN COVE, NY, 115...

Community: Breton Hills

The Retreat at Carmel

4 FROST CT, CARMEL, NY, 10512, Carmel, NY 10512

$759,900

2 beds

3 baths

2,035 sq ft

Condo

4 FROST CT, CARMEL, NY, 10512

Community: The Retreat at Carmel

Heritage Village

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

$339,900

2 beds

2 baths

1,063 sq ft

Condo

761 HERITAGE VLG D, SOUTHBURY, CT, 06488

Community: Heritage Village

Liberty at Newtown

79 SUZIE DR # 79, NEWTOWN, CT, 06470, Newtown, CT 06470

$575,000

2 beds

3 baths

2,317 sq ft

Condo

79 SUZIE DR # 79, NEWTOWN, CT, 06470

Community: Liberty at Newtown

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

Questions? Call us: (475) 244-9781

Stoneleigh Woods at Riverhead

23 GOOSE NECK LN, RIVERHEAD, NY, 11901, Riverhead, NY 11901

$585,000

2 beds

3 baths

1,631 sq ft

Condo

23 GOOSE NECK LN, RIVERHEAD, NY, 11901

Community: Stoneleigh Woods at Riverhead

Fairfield at St. James

901 FENWAY RD, SAINT JAMES, NY, 11780, Saint James, NY 11780

$499,000

2 beds

2 baths

1,230 sq ft

Condo

901 FENWAY RD, SAINT JAMES, NY, 11780

6 MORLEY CIR, MELVILLE, NY, 11747

Community: The Coves at Melville

Encore Atlantic Shores

6 OVATION PL, EASTPORT, NY, 11941, Eastport, NY 11941

$795,000

2 beds

2 baths

2,150 sq ft

Condo

6 OVATION PL, EASTPORT, NY, 11941

Community: Encore Atlantic Shores

Oronoque Village

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

$499,000

2 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

Leisure Village

128 EXMORE CT UNIT D, RIDGE, NY, 11961, Ridge, NY 11961

$319,900

2 beds

1 baths

1,278 sq ft

Condo

128 EXMORE CT UNIT D, RIDGE, NY, 11961

Community: Leisure Village

Rivington

85 WINDING RIDGE WAY # 85, DANBURY, CT, ..., Danbury, CT 06810

$825,000

3 beds

4 baths

1,794 sq ft

Condo

85 WINDING RIDGE WAY # 85, DANBURY, CT, ...

Community: Rivington

Heritage Village

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

$235,000

2 beds

2 baths

1,076 sq ft

Condo

162 HERITAGE VLG D, SOUTHBURY, CT, 06488

Community: Heritage Village

Stone Ridge Estates

153 CHRISTINE DR, DIX HILLS, NY, 11746, Dix Hills, NY 11746

$775,000

2 beds

2 baths

1,415 sq ft

Condo

153 CHRISTINE DR, DIX HILLS, NY, 11746

Condo

817 WILLOW LN, VALLEY STREAM, NY, 11580

Community: Dutchgate

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

Questions? Call us: (475) 244-9781

Meadowbrook Pointe Athletic Club & Spa

365 TROTTING LN, WESTBURY, NY, 11590, Westbury, NY 11590

$799,999

1 beds

2 baths

1,128 sq ft

Condo

365 TROTTING LN, WESTBURY, NY, 11590

Community: Meadowbrook Pointe Athletic Club & Spa

Heritage Hills

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

$600,000

2 beds

2 baths

1,470 sq ft

Condo

537 HERITAGE HLS D, SOMERS, NY, 10589

Community: Heritage Hills

The Summit at Bethel

32 HUNTING RIDGE LN # 32, BETHEL, CT, 06..., Bethel, CT 06801

$689,000

3 beds

4 baths

2,090 sq ft

Condo

32 HUNTING RIDGE LN # 32, BETHEL, CT, 06...

Community: The Summit at Bethel

Village Estates

119 FRANCESCA WAY # 119, AMITYVILLE, NY,..., Amityville, NY 11701

$549,000

2 beds

1 baths

1,234 sq ft

Condo

119 FRANCESCA WAY # 119, AMITYVILLE, NY,...

Community: Village Estates

Country Pointe Plainview

21105 ASPENWOOD DR, PLAINVIEW, NY, 11803, Plainview, NY 11803

$1,250,000

2 beds

2 baths

1,475 sq ft

Condo

21105 ASPENWOOD DR, PLAINVIEW, NY, 11803

Community: Country Pointe Plainview

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

Questions? Call us: (475) 244-9781

The Coach Homes at Ridgefield

233 DANBURY RD A209, RIDGEFIELD, CT, 068..., Ridgefield, CT 06877

$549,000

1 beds

2 baths

1,000 sq ft

Condo

233 DANBURY RD A209, RIDGEFIELD, CT, 068...

Community: The Coach Homes at Ridgefield

Leisure Village

274 BERWICK CT A, RIDGE, NY, 11961, Ridge, NY 11961

$349,999

2 beds

1 baths

836 sq ft

Condo

274 BERWICK CT A, RIDGE, NY, 11961

Community: Leisure Village

The Villages at Mount Sinai Park

4 OAKHURST CT, MOUNT SINAI, NY, 11766, Mount Sinai, NY 11766

$775,000

3 beds

3 baths

2,850 sq ft

House

4 OAKHURST CT, MOUNT SINAI, NY, 11766

Community: The Villages at Mount Sinai Park

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

Questions? Call us: (475) 244-9781

Leisure Village

373 WOODBRIDGE DR B, RIDGE, NY, 11961, Ridge, NY 11961

$415,000

2 beds

1 baths

1,171 sq ft

Condo

373 WOODBRIDGE DR B, RIDGE, NY, 11961

Community: Leisure Village

The Villas at Narragansett

816 NARRAGANSETT VILLAS DR # 816, LINDEN..., Lindenhurst, NY 11757

$559,000

2 beds

2 baths

1,215 sq ft

Condo

816 NARRAGANSETT VILLAS DR # 816, LINDEN...

Community: The Villas at Narragansett

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

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Cheshire, CT 55+ active adult communities & homes for sale - Page 2

129 communities near Cheshire

224 homes near Cheshire

3 beds

3 baths

Condo

3 beds

3 baths

Condo

3 beds

2 baths

2,056 sq ft

Condo

2 beds

2 baths

1,044 sq ft

Condo

2 beds

1 baths

1,036 sq ft

Condo

2 beds

2 baths

1,497 sq ft

Condo

3 beds

3 baths

1,426 sq ft

Condo

2 beds

2 baths

1,205 sq ft

Condo

1 beds

3 baths

1,426 sq ft

Condo

2 beds

2 baths

1,430 sq ft

Condo

2 beds

3 baths

2,035 sq ft

Condo

2 beds

2 baths

1,063 sq ft

Condo

2 beds

3 baths

2,317 sq ft

Condo

2 beds

3 baths

1,631 sq ft

Condo

2 beds

2 baths

1,230 sq ft

Condo

2 beds

2 baths

1,666 sq ft

Condo

2 beds

2 baths

1,432 sq ft

Condo

3 beds

3 baths

1,600 sq ft

Condo

2 beds

2 baths

Condo

2 beds

2 baths

2,150 sq ft

Condo