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

125 communities near Cheshire

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Breton Hills

$500Ks

Breton Hills, Glen Cove, NY

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

No reviews yet

The Polo Club at Islandia

$600Ks - $600Ks

The Polo Club at Islandia, Islandia, NY

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

No reviews yet

Long Hill Village

$300Ks - $400Ks

Long Hill Village, Trumbull, CT

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

No reviews yet

Regency at Woodbridge

$500Ks - $700Ks

Regency at Woodbridge, Woodbridge, CT

New Construction | 55+ age-restricted | Built 2023 - present | 70 homes

No reviews yet

The Village at Hunt Glen

$300Ks - $300Ks

The Village at Hunt Glen, Granby, CT

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

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

Questions? Call us: (475) 244-9781

No reviews yet

Stoneleigh Woods at Carme...

$400Ks - $400Ks

Stoneleigh Woods at Carme..., Carmel, NY

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

No reviews yet

Sonoma Woods

$300Ks - $300Ks

Sonoma Woods, Middletown, CT

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

No reviews yet

Eagles Walk at East Quogu...

$500Ks - $500Ks

Eagles Walk at East Quogu..., East Quogue, NY

Resale Only | 55+ age-restricted | Built 2004 - 2014 | 67 homes

No reviews yet

Hopmeadow Place

$200Ks - $300Ks

Hopmeadow Place, Simsbury, CT

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

No reviews yet

Whitney Glen

$500Ks - $600Ks

Whitney Glen, Westport, CT

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

RiverWalk

$500Ks - $600Ks

RiverWalk, Branford, CT

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

No reviews yet

The Village at Buckingham

$500Ks - $600Ks

The Village at Buckingham, Avon, CT

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

No reviews yet

Autumn Fields

$200Ks - $300Ks

Autumn Fields, Enfield, CT

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

No reviews yet

The Atrium of Portland

<$100k - $100Ks

The Atrium of Portland, Portland, CT

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

No reviews yet

77 Sunset Lane

$400Ks - $700Ks

77 Sunset Lane, Ridgefield, CT

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

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

Questions? Call us: (475) 244-9781

No reviews yet

Evergreen

$400Ks - $500Ks

Evergreen, Cromwell, CT

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

No reviews yet

Regency Meadows

$500Ks - $500Ks

Regency Meadows, Trumbull, CT

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

No reviews yet

Villas at Seminary Hill

$400Ks - $400Ks

Villas at Seminary Hill, Carmel, NY

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

No reviews yet

Eastport Meadows

$400Ks - $400Ks

Eastport Meadows, Eastport, NY

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

No reviews yet

Gloria Commons

$400Ks - $400Ks

Gloria Commons, Milford, CT

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

No reviews yet

Bramble Ridge

$400Ks - $500Ks

Bramble Ridge, Suffield, CT

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

No reviews yet

Chimney Hill

$500Ks - $700Ks

Chimney Hill, Farmington, CT

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

No reviews yet

Village Vistas

$800Ks - $1Ms

Village Vistas, Port Jefferson, NY

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

No reviews yet

Harbor View Estates

$400Ks - $600Ks

Harbor View Estates, Copiague, NY

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

No reviews yet

Forest Mews

$300Ks - $400Ks

Forest Mews, Avon, CT

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

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

Questions? Call us: (475) 244-9781

No reviews yet

Clockmaker's Hill

$100Ks - $100Ks

Clockmaker's Hill, Winsted, CT

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

No reviews yet

Hidden Harbor Estates

$500Ks - $600Ks

Hidden Harbor Estates, Copiague, NY

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

No reviews yet

Bidwell Village

$300Ks - $400Ks

Bidwell Village, Coventry, CT

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

No reviews yet

Billingsgate

$400Ks - $600Ks

Billingsgate, Simsbury, CT

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

No reviews yet

Stratford Park

$900Ks - $900Ks

Stratford Park, Melville, NY

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

No reviews yet

Boulder Brook

$200Ks - $200Ks

Boulder Brook, Prospect, CT

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

No reviews yet

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

No reviews yet

Knickerbocker Bay Club

$700Ks - $3Ms

Knickerbocker Bay Club, Port Washington, NY

New and Resale | 55+ age-restricted | Built 2014 - present | 32 homes

No reviews yet

Oak Meadow Estates

$200Ks - $400Ks

Oak Meadow Estates, Torrington, CT

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

No reviews yet

Jessup's Landing

$1Ms - $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

No reviews yet

Autumn Estates

$500Ks - $600Ks

Autumn Estates, Farmington, CT

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

No reviews yet

The Coach Homes at Ridgef...

$200Ks - $500Ks

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

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

No reviews yet

RiverBend Estates

$400Ks - $400Ks

RiverBend Estates, Oxford, CT

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

No reviews yet

Bartlett Hollow

$200Ks - $400Ks

Bartlett Hollow, Middletown, CT

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

No reviews yet

Granite Woods

$600Ks - $700Ks

Granite Woods, Middlebury, CT

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

1 2 3...4

The Gardens of Wilbraham

45 IVY CIR # 45, WILBRAHAM, MA, 01095, Wilbraham, MA 01095

$475,000

2 beds

3 baths

1,752 sq ft

Condo

45 IVY CIR # 45, WILBRAHAM, MA, 01095

23 SONATA CT, LAKE GROVE, NY, 11755

Community: Encore at Lake Grove

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

Questions? Call us: (475) 244-9781

Encore Atlantic Shores

68 ENCORE, BROOKHAVEN, NY, 11941, Brookhaven, NY 11941

$779,000

2 beds

3 baths

3,000 sq ft

Condo

68 ENCORE, BROOKHAVEN, NY, 11941

Community: Encore Atlantic Shores

New Heritage Hills

406 HERITAGE HLS C, SOMERS, NY, 10589, Somers, NY 10589

$639,000

2 beds

2 baths

1,296 sq ft

Condo

406 HERITAGE HLS C, SOMERS, NY, 10589

Community: Heritage Hills

Leisure Village

28 TRENT CT B, RIDGE, NY, 11961, Ridge, NY 11961

$368,000

2 beds

1 baths

1,200 sq ft

Condo

28 TRENT CT B, RIDGE, NY, 11961

Community: Leisure Village

The Waterways at Moriches

537 HIGHLAND CT, MORICHES, NY, 11955, Moriches, NY 11955

$565,000

2 beds

2 baths

1,839 sq ft

Condo

537 HIGHLAND CT, MORICHES, NY, 11955

Community: The Waterways at Moriches

The Manors at The Colony Preserve

64 GREENTREE CT, SHIRLEY, NY, 11967, Shirley, NY 11967

$499,000

2 beds

2 baths

1,419 sq ft

Condo

64 GREENTREE CT, SHIRLEY, NY, 11967

Community: The Manors at The Colony Preserve

Leisure Village

247 NEWCASTLE CT A, RIDGE, NY, 11961, Ridge, NY 11961

$425,000

2 beds

2 baths

1,564 sq ft

Condo

247 NEWCASTLE 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

$799,999

3 beds

3 baths

2,850 sq ft

Condo

4 OAKHURST CT, MOUNT SINAI, NY, 11766

Community: The Villages at Mount Sinai Park

Leisure Village

195 E NEWCASTLE CT, BROOKHAVEN, NY, 1196..., Brookhaven, NY 11961

$229,000

1 beds

1 baths

684 sq ft

Condo

195 E NEWCASTLE CT, BROOKHAVEN, NY, 1196...

Community: Leisure Village

Greenwood Village

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

$174,990

2 beds

2 baths

938 sq ft

Manufactured Home

164 VILLAGE CIR, MANORVILLE, NY, 11949

Community: Greenwood Village

Setauket Meadows

131 EMILYS WAY, EAST SETAUKET, NY, 11733, East Setauket, NY 11733

$735,000

2 beds

3 baths

1,773 sq ft

Condo

131 EMILYS WAY, EAST SETAUKET, NY, 11733

Community: Setauket Meadows

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

Questions? Call us: (475) 244-9781

New Glenwood Village

1661 OLD COUNTRY RD 163, RIVERHEAD, NY, ..., Riverhead, NY 11901

$164,999

2 beds

1 baths

500 sq ft

Mobile Home

1661 OLD COUNTRY RD 163, RIVERHEAD, NY, ...

Community: Glenwood Village

Leisure Knoll

190 CANTERBURY DR, RIDGE, NY, 11961, Ridge, NY 11961

$434,999

2 beds

1 baths

787 sq ft

Condo

190 CANTERBURY DR, RIDGE, NY, 11961

Community: Leisure Knoll

Leisure Village

310 WOODBRIDGE DR UNIT C, RIDGE, NY, 119..., Ridge, NY 11961

$349,000

2 beds

1 baths

1,278 sq ft

Condo

310 WOODBRIDGE DR UNIT C, RIDGE, NY, 119...

Community: Leisure Village

Glenwood Village

1661 OLD COUNTRY RD 308, RIVERHEAD, NY, ..., Riverhead, NY 11901

$149,000

2 beds

1 baths

840 sq ft

Mobile Home

1661 OLD COUNTRY RD 308, RIVERHEAD, NY, ...

Community: Glenwood Village

Greenwood Village

57 DOGWOOD LN, MANORVILLE, NY, 11949, Manorville, NY 11949

$159,999

2 beds

2 baths

1,000 sq ft

Condo

57 DOGWOOD LN, MANORVILLE, NY, 11949

Community: Greenwood Village

Heritage Hills

133 HERITAGE HLS B, SOMERS, NY, 10589, Somers, NY 10589

$700,000

3 beds

2 baths

1,780 sq ft

Condo

133 HERITAGE HLS B, SOMERS, NY, 10589

Community: Heritage Hills

New Leisure Knoll

147 EDINBURGH DR, RIDGE, NY, 11961, Ridge, NY 11961

$455,000

2 beds

2 baths

900 sq ft

Condo

147 EDINBURGH DR, RIDGE, NY, 11961

Community: Leisure Knoll

Jefferson Village

40 JEFFERSON OVAL A, YORKTOWN HEIGHTS, N..., Yorktown Heights, NY 10598

$539,000

2 beds

2 baths

1,350 sq ft

Condo

40 JEFFERSON OVAL A, YORKTOWN HEIGHTS, N...

Community: Jefferson Village

The Greens at Half Hollow

423 FLORENCIA PL, MELVILLE, NY, 11747, Melville, NY 11747

$1,275,000

3 beds

3 baths

2,500 sq ft

Condo

423 FLORENCIA PL, MELVILLE, NY, 11747

Community: The Greens at Half Hollow

New The Greens at Half Hollow

344 ALTESSA BLVD, MELVILLE, NY, 11747, Melville, NY 11747

$1,599,000

2 beds

2 baths

2,800 sq ft

Condo

344 ALTESSA BLVD, MELVILLE, NY, 11747

Community: The Greens at Half Hollow

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

Questions? Call us: (475) 244-9781

Glenwood Village

1661 OLD COUNTRY RD UNIT 508, RIVERHEAD,..., Riverhead, NY 11901

$399,000

2 beds

2 baths

1,500 sq ft

Manufactured Home

1661 OLD COUNTRY RD UNIT 508, RIVERHEAD,...

Community: Glenwood Village

Glenwood Village

1661 OLD COUNTRY RD UNIT 543, RIVERHEAD,..., Riverhead, NY 11901

$410,000

2 beds

2 baths

1,632 sq ft

Manufactured Home

1661 OLD COUNTRY RD UNIT 543, RIVERHEAD,...

Community: Glenwood Village

Stone Ridge Estates

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

$820,000

2 beds

2 baths

1,567 sq ft

Condo

138 CHRISTINE DR, DIX HILLS, NY, 11746

Community: Stone Ridge Estates

The Greens at Half Hollow

911 ALTESSA BLVD, MELVILLE, NY, 11747, Melville, NY 11747

$649,000

2 beds

2 baths

1,134 sq ft

Condo

911 ALTESSA BLVD, MELVILLE, NY, 11747

Community: The Greens at Half Hollow

Leisure Knoll

187 EDINBURGH DR, RIDGE, NY, 11961, Ridge, NY 11961

$395,000

2 beds

2 baths

913 sq ft

Condo

187 EDINBURGH DR, RIDGE, NY, 11961

Community: Leisure Knoll

The Greens at Half Hollow

1126 SAVOY DR, MELVILLE, NY, 11747, Melville, NY 11747

$629,888

2 beds

2 baths

1,150 sq ft

Condo

1126 SAVOY DR, MELVILLE, NY, 11747

Community: The Greens at Half Hollow

The Greens at Half Hollow

685 BALFOUR PL, MELVILLE, NY, 11747, Melville, NY 11747

$999,000

2 beds

3 baths

1,940 sq ft

Condo

685 BALFOUR PL, MELVILLE, NY, 11747

Community: The Greens at Half Hollow

New Leisure Village

151 EASTBOURNE CT B, RIDGE, NY, 11961, Ridge, NY 11961

$525,000

2 beds

2 baths

1,746 sq ft

Condo

151 EASTBOURNE CT B, RIDGE, NY, 11961

Community: Leisure Village

New Leisure Village

171B VENTRY CT 171B, BROOKHAVEN, NY, 119..., Brookhaven, NY 11961

$269,000

1 beds

1 baths

679 sq ft

Condo

171B VENTRY CT 171B, BROOKHAVEN, NY, 119...

Community: Leisure Village

Vineyards at Brookfield

146 AVERY DR N, CENTER MORICHES, NY, 119..., Center Moriches, NY 11934

$899,999

3 beds

4 baths

3,000 sq ft

Condo

146 AVERY DR N, CENTER MORICHES, NY, 119...

Condo

109 LOUDEN LOOP, MOUNT SINAI, NY, 11766

Community: The Villages at Mount Sinai Park

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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.

Want more information about active adult communities around Cheshire?

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125 communities near Cheshire

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

125 communities near Cheshire

290 homes near Cheshire

2 beds

3 baths

1,752 sq ft

Condo

2 beds

2 baths

1,542 sq ft

Condo

2 beds

2 baths

942 sq ft

Condo

2 beds

2 baths

1,246 sq ft

Condo

2 beds

2 baths

1,730 sq ft

Condo

2 beds

3 baths

3,000 sq ft

Condo

2 beds

2 baths

1,296 sq ft

Condo

2 beds

1 baths

1,200 sq ft

Condo

2 beds

2 baths

1,839 sq ft

Condo

2 beds

2 baths

1,419 sq ft

Condo

2 beds

2 baths

1,564 sq ft

Condo

3 beds

3 baths

2,850 sq ft

Condo

1 beds

1 baths

684 sq ft

Condo

2 beds

2 baths

938 sq ft

Manufactured Home

2 beds

3 baths

1,773 sq ft

Condo

2 beds

1 baths

500 sq ft

Mobile Home

2 beds

1 baths

787 sq ft

Condo

2 beds

1 baths

1,278 sq ft

Condo

2 beds

1 baths

840 sq ft

Mobile Home

2 beds