Cheshire, CT 55+ active adult communities & homes for sale - Page 3

129 communities near Cheshire

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Fieldstone Village

$500Ks - $800Ks

Fieldstone Village, Orange, CT

Resale Only | 55+ age-restricted | Built 2010 - 2018 | 142 homes

Pond Spring Village

$300Ks

Pond Spring Village, Beacon Falls, CT

New and Resale | 55+ age-restricted | Built 2005 - present | 92 homes

Beckley Farms

$300Ks - $400Ks

Beckley Farms, Berlin, CT

New and Resale | 55+ age-restricted | Built 2010 - present | 170 homes

Meadow Brook Estates

$500Ks

Meadow Brook Estates, Oxford, CT

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

Castle Heights of Cheshir...

$500Ks - $600Ks

Castle Heights of Cheshir..., Cheshire, CT

Resale Only | 55+ age-restricted | Built 2007 - 2022 | 88 homes

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

Chimney Hill

$500Ks - $700Ks

Chimney Hill, Farmington, CT

Resale Only | 55+ age-restricted | Built 2006 - 2013 | 44 homes

RiverWalk

$500Ks - $600Ks

RiverWalk, Branford, CT

New and Resale | 55+ age-restricted | Built 2007 - present | 60 homes

Newington Ridge Preserve

$300Ks - $400Ks

Newington Ridge Preserve, Newington, CT

New Construction | 55+ age-restricted | Built 2014 - present | 16 homes

The Powder Forest Homes

$600Ks - $700Ks

The Powder Forest Homes, Simsbury, CT

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

5 rating (3 reviews)

Founders Ridge

$500Ks - $600Ks

Founders Ridge, Middletown, CT

New Construction | 55+ age-restricted | Built 2017 - present | 75 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.

77 Sunset Lane

$400Ks - $700Ks

77 Sunset Lane, Ridgefield, CT

Resale Only | 55+ age-restricted | Built 2016 - 2018 | 54 homes

Bartlett Hollow

$200Ks - $400Ks

Bartlett Hollow, Middletown, CT

New Construction | 55+ age-restricted | Built 2015 - present | 25 homes

Autumn Estates

$500Ks - $600Ks

Autumn Estates, Farmington, CT

Resale Only | 55+ age-restricted | Built 2011 - 2017 | 30 homes

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

Questions? Call us: (475) 244-9781

The Atrium of Portland

<$100k

The Atrium of Portland, Portland, CT

Resale Only | 55+ age-restricted | Built 2004 - 2004 | 56 homes

Billingsgate

$400Ks - $600Ks

Billingsgate, Simsbury, CT

Resale Only | 55+ age-restricted | Built 2003 - 2006 | 37 homes

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

Questions? Call us: (475) 244-9781

Boulder Brook

$200Ks

Boulder Brook, Prospect, CT

Resale Only | 55+ age-restricted | Built 2004 - 2006 | 35 homes

Gloria Commons

$400Ks

Gloria Commons, Milford, CT

Resale Only | 55+ age-restricted | Built 2007 - 2015 | 50 homes

Hopmeadow Place

$200Ks - $300Ks

Hopmeadow Place, Simsbury, CT

Resale Only | 55+ age-restricted | Built 2005 - 2005 | 66 homes

Long Hill Village

$300Ks - $400Ks

Long Hill Village, Trumbull, CT

Resale Only | 55+ age-restricted | Built 1997 - 1999 | 71 homes

RiverBend Estates

$400Ks

RiverBend Estates, Oxford, CT

New and Resale | 55+ age-restricted | Built 2012 - present | 25 homes

Summer Wind Estates

$300Ks - $400Ks

Summer Wind Estates, North Haven, CT

New Construction | 55+ age-restricted | Built 2015 - present | 18 homes

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

Questions? Call us: (475) 244-9781

The Woods at Dunham Pond

$400Ks - $500Ks

The Woods at Dunham Pond, New Fairfield, CT

Resale Only | 55+ age-restricted | Built 2004 - 2015 | 33 homes

Regency Meadows

$500Ks

Regency Meadows, Trumbull, CT

Resale Only | 55+ age-restricted | Built 2003 - 2005 | 51 homes

Forest Mews

$300Ks - $400Ks

Forest Mews, Avon, CT

Resale Only | 55+ age-restricted | Built 2001 - 2004 | 40 homes

The Village at Hunt Glen

$300Ks

The Village at Hunt Glen, Granby, CT

Resale Only | 55+ age-restricted | Built 2003 - 2006 | 69 homes

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

Questions? Call us: (475) 244-9781

O'Meara Farm

$400Ks - $500Ks

O'Meara Farm, Farmington, CT

Resale Only | 55+ age-restricted | Built 1998 - 2005 | 104 homes

The Coach Homes at Ridgef...

$200Ks - $500Ks

The Coach Homes at Ridgef..., Ridgefield, CT

New Construction | 55+ age-restricted | Built 2019 - present | 30 homes

Whitney Glen

$500Ks - $600Ks

Whitney Glen, Westport, CT

Resale Only | 55+ age-restricted | Built 1982 - 1982 | 62 homes

Shaker Heights

$400Ks - $500Ks

Shaker Heights, Enfield, CT

New Construction | 55+ age-restricted | Built 2018 - present | 77 homes

Bramble Ridge

$400Ks - $500Ks

Bramble Ridge, Suffield, CT

Resale Only | 55+ age-restricted | Built 2005 - 2015 | 47 homes

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

Questions? Call us: (475) 244-9781

Autumn Fields

$200Ks - $300Ks

Autumn Fields, Enfield, CT

Resale Only | 55+ age-restricted | Built 2004 - 2006 | 56 homes

Founders Village

$500Ks - $600Ks

Founders Village, Southold, NY

Resale Only | 55+ age-restricted | Built 1981 - 1985 | 92 homes

Vineyards at Moriches

$700Ks

Vineyards at Moriches, Center Moriches, NY

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

Eastport Meadows

$400Ks

Eastport Meadows, Eastport, NY

Resale Only | 55+ age-restricted | Built 2009 - 2016 | 50 homes

Stoneleigh Woods at Carme...

$400Ks

Stoneleigh Woods at Carme..., Carmel, NY

Resale Only | 55+ age-restricted | Built 2012 - 2017 | 68 homes

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

Questions? Call us: (475) 244-9781

Saddle Lakes

$400Ks

Saddle Lakes, Riverhead, NY

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

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

Village Vistas

$800Ks - $1Ms

Village Vistas, Port Jefferson, NY

Resale Only | 55+ age-restricted | Built 2013 - 2017 | 43 homes

Setauket Meadows

$600Ks - $700Ks

Setauket Meadows, Setauket, NY

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

1 2 3...4

Leisure Village

164 FALMOUTH CT E, RIDGE, NY, 11961, Ridge, NY 11961

$279,000

2 beds

1 baths

819 sq ft

Condo

164 FALMOUTH CT E, RIDGE, NY, 11961

335 HERITAGE VLG B, SOUTHBURY, CT, 06488

Community: Heritage Village

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

Questions? Call us: (475) 244-9781

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Jefferson Village

96 MOLLY PITCHER LN H, YORKTOWN HEIGHTS,..., Yorktown Heights, NY 10598

$479,000

2 beds

2 baths

1,050 sq ft

Condo

96 MOLLY PITCHER LN H, YORKTOWN HEIGHTS,...

Community: Jefferson Village

The Retreat at Carmel

14 LANGDON GROVE, CARMEL, NY, 10512, Carmel, NY 10512

$699,900

3 beds

3 baths

3,000 sq ft

Condo

14 LANGDON GROVE, CARMEL, NY, 10512

Community: The Retreat at Carmel

Leisure Village

432A FALMOUTH CT # 432A, RIDGE, NY, 1196..., Ridge, NY 11961

$389,000

2 beds

1 baths

1,074 sq ft

Condo

432A FALMOUTH CT # 432A, RIDGE, NY, 1196...

Community: Leisure Village

Spring Lake Village

621 OVERLOOK PATH # 621, SOUTHINGTON, CT..., Southington, CT 06489

$340,000

2 beds

3 baths

1,133 sq ft

Condo

621 OVERLOOK PATH # 621, SOUTHINGTON, CT...

Community: Spring Lake Village

Greenwood Village

164 VILLAGE CIR, MANORVILLE, NY, 11949, Manorville, NY 11949

$149,997

2 beds

2 baths

938 sq ft

Condo

164 VILLAGE CIR, MANORVILLE, NY, 11949

Community: Greenwood Village

Leisure Village

360 WOODBRIDGE DR A, RIDGE, NY, 11961, Ridge, NY 11961

$459,000

2 beds

2 baths

1,250 sq ft

Condo

360 WOODBRIDGE DR A, RIDGE, NY, 11961

Community: Leisure Village

Oronoque Village

617 CHEROKEE LN B, STRATFORD, CT, 06614, Stratford, CT 06614

$524,900

1 beds

3 baths

1,438 sq ft

Condo

617 CHEROKEE LN B, STRATFORD, CT, 06614

Community: Oronoque Village

Leisure Village

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

$247,500

1 beds

1 baths

782 sq ft

Condo

423 WOODBRIDGE DR 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

Heritage Village

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

$329,000

2 beds

2 baths

1,432 sq ft

Condo

98 HERITAGE VLG A, SOUTHBURY, CT, 06488

Community: Heritage Village

The Vineyards at Miller Place

45 HALLEY LN, MILLER PLACE, NY, 11764, Miller Place, NY 11764

$650,000

2 beds

3 baths

1,853 sq ft

Condo

45 HALLEY LN, MILLER PLACE, NY, 11764

Condo

123 HERITAGE VLG B, SOUTHBURY, CT, 06488

Community: Heritage Village

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

Questions? Call us: (475) 244-9781

Baldwin Station

7 FIRE THORN LN # 7, MILFORD, CT, 06461, Milford, CT 06461

$689,950

2 beds

3 baths

2,331 sq ft

Condo

7 FIRE THORN LN # 7, MILFORD, CT, 06461

Community: Baldwin Station

The Waterways at Moriches

477 WOODSCREEK CT, MORICHES, NY, 11955, Moriches, NY 11955

$565,000

3 beds

2 baths

1,839 sq ft

Condo

477 WOODSCREEK CT, MORICHES, NY, 11955

Community: The Waterways at Moriches

Oronoque Village

766 NYACK LN B, STRATFORD, CT, 06614, Stratford, CT 06614

$649,000

1 beds

3 baths

1,438 sq ft

Condo

766 NYACK LN B, STRATFORD, CT, 06614

Community: Oronoque Village

Heritage Hills

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

$675,000

3 beds

2 baths

1,689 sq ft

Condo

59 HERITAGE HLS A, SOMERS, NY, 10589

Community: Heritage Hills

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

Questions? Call us: (475) 244-9781

Bartlett Hill

9 PEAR ORCHARD RD # 9, PORTLAND, CT, 064..., Portland, CT 06480

2 beds

2 baths

1,204 sq ft

Condo

81 SILO WAY # 81, BLOOMFIELD, CT, 06002

Community: South Pond Village

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

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Leisure Village

380 WOODBRIDGE DR D, RIDGE, NY, 11961, Ridge, NY 11961

$439,000

2 beds

2 baths

1,147 sq ft

Condo

380 WOODBRIDGE DR D, RIDGE, NY, 11961

Community: Leisure Village

The Seasons at Plainview

119 AUTUMN DR, PLAINVIEW, NY, 11803, Plainview, NY 11803

$799,000

2 beds

2 baths

1,379 sq ft

Condo

119 AUTUMN DR, PLAINVIEW, NY, 11803

Community: The Seasons at Plainview

Foxwood Village

1407 MIDDLE RD 275, CALVERTON, NY, 11933, Calverton, NY 11933

$425,000

3 beds

2 baths

1,530 sq ft

House

1407 MIDDLE RD 275, CALVERTON, NY, 11933

Community: Foxwood Village

Oronoque Village

522 IROQUOIS LN B, STRATFORD, CT, 06614, Stratford, CT 06614

$399,000

2 beds

3 baths

1,426 sq ft

Condo

522 IROQUOIS LN B, STRATFORD, CT, 06614

Community: Oronoque Village

Fairfield at St. James

504 GOTHAM CT, SAINT JAMES, NY, 11780, Saint James, NY 11780

$499,995

1 beds

2 baths

1,036 sq ft

House

504 GOTHAM CT, SAINT JAMES, NY, 11780

Condo

177 MELODY CT, EASTPORT, NY, 11941

Community: Encore Atlantic Shores

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

Questions? Call us: (475) 244-9781

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

Jefferson Village

17 HASTINGS B, YORKTOWN, NY, 10598, Yorktown, NY 10598

$235,000

1 baths

600 sq ft

Condo

17 HASTINGS B, YORKTOWN, NY, 10598

Community: Jefferson Village

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 3

129 communities near Cheshire

224 homes near Cheshire

2 beds

1 baths

819 sq ft

Condo

2 beds

2 baths

1,323 sq ft

Condo

2 beds

3 baths

1,550 sq ft

Condo

2 beds

2 baths

1,590 sq ft

Condo

2 beds

2 baths

1,032 sq ft

Condo

2 beds

2 baths

1,050 sq ft

Condo

3 beds

3 baths

3,000 sq ft

Condo

2 beds

1 baths

1,074 sq ft

Condo

2 beds

3 baths

1,133 sq ft

Condo

2 beds

2 baths

938 sq ft

Condo

2 beds

2 baths

1,250 sq ft

Condo

1 beds

3 baths

1,438 sq ft

Condo

1 beds

1 baths

782 sq ft

Condo

2 beds

2 baths

1,432 sq ft

Condo

2 beds

3 baths

1,853 sq ft

Condo

1 beds

1 baths

928 sq ft

Condo

2 beds

2 baths

1,341 sq ft

Condo

2 beds

2 baths

1,365 sq ft

Condo

2 beds

2 baths

1,500 sq ft

Condo

2 beds