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

125 communities near Cheshire

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5 rating (1 reviews)

The Villages at Mount Sin...

$700Ks - $800Ks

The Villages at Mount Sin..., Mount Sinai, NY

Resale Only | 55+ age-restricted | Built 2005 - 2007 | 185 homes

No reviews yet

The Powder Forest Homes

$600Ks - $700Ks

The Powder Forest Homes, Simsbury, CT

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

5 rating (1 reviews)

Newtown Woods

$400Ks - $500Ks

Newtown Woods, Newtown, CT

New and Resale | 55+ age-restricted | Built 2011 - present | 178 homes

No reviews yet

Stoneleigh Woods at River...

$400Ks - $600Ks

Stoneleigh Woods at River..., Riverhead, NY

Resale Only | 55+ age-restricted | Built 2007 - 2016 | 176 homes

No reviews yet

Snug Harbor

$600Ks - $700Ks

Snug Harbor, Amityville, NY

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

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

Questions? Call us: (475) 244-9781

No reviews yet

The Coves at Melville

$500Ks - $500Ks

The Coves at Melville, Melville, NY

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

No reviews yet

Strathmore Gate East

$300Ks - $300Ks

Strathmore Gate East, Coram, NY

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

No reviews yet

Beckley Farms

$300Ks - $400Ks

Beckley Farms, Berlin, CT

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

No reviews yet

South Pond Village

$200Ks - $400Ks

South Pond Village, Bloomfield, CT

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

No reviews yet

The Manors at The Colony ...

$400Ks - $500Ks

The Manors at The Colony ..., Shirley, NY

New Construction | 55+ age-restricted | Built 2013 - present | 150 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

Setauket Meadows

$600Ks - $700Ks

Setauket Meadows, Setauket, NY

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

No reviews yet

Vineyards at Brookfield

$600Ks - $600Ks

Vineyards at Brookfield, Center Moriches, NY

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

No reviews yet

Fieldstone Village

$500Ks - $800Ks

Fieldstone Village, Orange, CT

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

No reviews yet

North Woods of Colchester

$300Ks - $400Ks

North Woods of Colchester, Colchester, CT

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

No reviews yet

Village Estates

$500Ks - $500Ks

Village Estates, Amityville, NY

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

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

Questions? Call us: (475) 244-9781

No reviews yet

The Villas at Narraganset...

$500Ks - $500Ks

The Villas at Narraganset..., Lindenhurst, NY

Resale Only | 55+ age-restricted | Built 2004 - 2005 | 138 homes

No reviews yet

The Seasons at Plainview

$600Ks - $700Ks

The Seasons at Plainview, Plainview, NY

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

No reviews yet

Windcrest East

$600Ks - $600Ks

Windcrest East, Calverton, NY

Resale Only | 55+ age-restricted | Built 2004 - 2005 | 126 homes

No reviews yet

Fairview at Oxford Greens

$600Ks - $700Ks

Fairview at Oxford Greens, Oxford, CT

New and Resale | 55+ age-restricted | Built 2019 - present | 125 homes

3.5 rating (2 reviews)

Harvest Pointe

$800Ks - $3Ms

Harvest Pointe, Cutchogue, NY

New Construction | 55+ age-restricted | Built 2017 - present | 124 homes

No reviews yet

Newbury Village

$600Ks - $700Ks

Newbury Village, Brookfield, CT

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

No reviews yet

The Seasons at Seaford

$700Ks - $700Ks

The Seasons at Seaford, Seaford, NY

Resale Only | 55+ age-restricted | Built 2015 - 2017 | 112 homes

No reviews yet

Windmill Gate

$300Ks - $400Ks

Windmill Gate, Oakdale, NY

Resale Only | 55+ age-restricted | Built 1989 - 1991 | 110 homes

No reviews yet

The Gardens of Wilbraham

$300Ks - $400Ks

The Gardens of Wilbraham, Wilbraham, MA

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

No reviews yet

O'Meara Farm

$400Ks - $500Ks

O'Meara Farm, Farmington, CT

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

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

Questions? Call us: (475) 244-9781

No reviews yet

Meadowbrooke Pointe East ...

$700Ks - $700Ks

Meadowbrooke Pointe East ..., East Meadow, NY

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

No reviews yet

Liberty at Newtown

$300Ks - $400Ks

Liberty at Newtown, Newtown, CT

Resale Only | 55+ age-restricted | Built 2003 - 2007 | 96 homes

No reviews yet

The Bel Aire at East Mead...

$400Ks - $400Ks

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

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

No reviews yet

Founders Village

$500Ks - $500Ks

Founders Village, Southold, NY

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

No reviews yet

Vineyards at Moriches

$600Ks - $700Ks

Vineyards at Moriches, Center Moriches, NY

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

No reviews yet

Pond Spring Village

$300Ks - $300Ks

Pond Spring Village, Beacon Falls, CT

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

No reviews yet

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

No reviews yet

The Vineyards at Miller P...

$600Ks - $600Ks

The Vineyards at Miller P..., Miller Place, NY

Resale Only | 55+ age-restricted | Built 2004 - 2005 | 85 homes

No reviews yet

Bartlett Hill

$500Ks - $500Ks

Bartlett Hill, Portland, CT

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

No reviews yet

Baldwin Station

$400Ks - $400Ks

Baldwin Station, Milford, CT

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

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

Questions? Call us: (475) 244-9781

No reviews yet

Kensington Estates

$1Ms - $1Ms

Kensington Estates, Woodbury, NY

New Construction | 55+ age-restricted | Built 2019 - 2021 | 80 homes

5 rating (2 reviews)

Benson Woods

$400Ks - $600Ks

Benson Woods, Middlebury, CT

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

No reviews yet

Shaker Heights

$400Ks - $500Ks

Shaker Heights, Enfield, CT

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

No reviews yet

Stone Ridge Estates

$800Ks - $800Ks

Stone Ridge Estates, Dix Hills, NY

Resale Only | 55+ age-restricted | Built 2004 - 2013 | 76 homes

5 rating (3 reviews)

Founders Ridge

$500Ks - $600Ks

Founders Ridge, Middletown, CT

New Construction | 55+ age-restricted | Built 2017 - present | 75 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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Want to learn more about 55+ communities in Cheshire?

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125 communities near Cheshire

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

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