Cheshire, CT 55+ rental communities & homes for rent

1 communities near Cheshire

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The Cornerstone at Hauppa...

$2,600s / mo

Base rent from $2,750

The Cornerstone at Hauppa..., Hauppauge, NY

New Construction | 55+ age-restricted | Built 2019 - 2020 | 96 rental 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.

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

Questions? Call us: (475) 244-9781

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.

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

Questions? Call us: (475) 244-9781

The Gardens of Wilbraham

32 LODGE LN # 32, WILBRAHAM, MA, 01095, Wilbraham, MA 01095

$565,000

2 beds

2 baths

1,610 sq ft

Condo

32 LODGE LN # 32, WILBRAHAM, MA, 01095

Community: The Gardens of Wilbraham

Fairfield at St. James

401 CABOT CT, SMITHTOWN, NY, 11780, Smithtown, NY 11780

$485,000

1 beds

2 baths

900 sq ft

Condo

401 CABOT CT, SMITHTOWN, NY, 11780

Community: Fairfield at St. James

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

Heritage Hills

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

$699,000

2 beds

2 baths

1,559 sq ft

Condo

390 HERITAGE HLS A, SOMERS, NY, 10589

Community: Heritage Hills

New The Seasons at East Meadow

294 SPRING DR, EAST MEADOW, NY, 11554, East Meadow, NY 11554

$639,999

2 beds

2 baths

1,050 sq ft

Condo

294 SPRING DR, EAST MEADOW, NY, 11554

Community: The Seasons at East Meadow

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

Questions? Call us: (475) 244-9781

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

Questions? Call us: (475) 244-9781

New 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 Greens at Half Hollow

677 BALFOUR PL, MELVILLE, NY, 11747, Melville, NY 11747

$1,075,000

2 beds

3 baths

1,900 sq ft

Condo

677 BALFOUR PL, MELVILLE, NY, 11747

Community: The Greens at Half Hollow

Saddle Lakes

98 SCENIC LAKE DR, RIVERHEAD, NY, 11901, Riverhead, NY 11901

$749,990

3 beds

3 baths

1,837 sq ft

Condo

98 SCENIC LAKE DR, RIVERHEAD, NY, 11901

Community: Saddle Lakes

Greenwood Village

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

$164,997

2 beds

2 baths

938 sq ft

Condo

164 VILLAGE CIR, MANORVILLE, NY, 11949

Community: Greenwood Village

Leisure Village

475 DARWEN DR B, RIDGE, NY, 11961, Ridge, NY 11961

$437,500

2 beds

2 baths

1,423 sq ft

Condo

475 DARWEN DR B, RIDGE, NY, 11961

Community: Leisure Village

Leisure Village

169 VENTRY CT A, RIDGE, NY, 11961, Ridge, NY 11961

$289,000

2 beds

1 baths

875 sq ft

Condo

169 VENTRY CT A, RIDGE, NY, 11961

Community: Leisure Village

Stone Ridge Estates

108 JOSEPH LN, DIX HILLS, NY, 11746, Dix Hills, NY 11746

$799,999

2 beds

2 baths

1,695 sq ft

Condo

108 JOSEPH LN, DIX HILLS, NY, 11746

Community: Stone Ridge Estates

Snug Harbor

118 HARBOR, AMITYVILLE, NY, 11701, Amityville, NY 11701

$649,000

2 beds

2 baths

935 sq ft

Condo

118 HARBOR, AMITYVILLE, NY, 11701

Community: Snug Harbor

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

Questions? Call us: (475) 244-9781

Leisure Glen

408 LEISURE DR, RIDGE, NY, 11961, Ridge, NY 11961

$569,500

2 beds

2 baths

1,434 sq ft

Condo

408 LEISURE DR, RIDGE, NY, 11961

Community: Leisure Glen

Heritage Hills

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

$699,000

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

Heritage Hills

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

$675,000

2 beds

2 baths

1,500 sq ft

Condo

55 HERITAGE HLS A, SOMERS, NY, 10589

Community: Heritage Hills

The Retreat at Carmel

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

$699,900

2 beds

3 baths

1,957 sq ft

Condo

14 LANGDON GROVE, CARMEL, NY, 10512

Community: The Retreat at Carmel

Leisure Village

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

$210,000

1 beds

1 baths

684 sq ft

Condo

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

Community: Leisure Village

Jefferson Village

15 ESSEX PL 15K, YORKTOWN, NY, 10598, Yorktown, NY 10598

$375,000

2 beds

1 baths

1,000 sq ft

Condo

15 ESSEX PL 15K, YORKTOWN, NY, 10598

Community: Jefferson Village

The Greens at Half Hollow

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

$629,000

2 beds

2 baths

1,134 sq ft

Condo

911 ALTESSA BLVD, MELVILLE, NY, 11747

Community: The Greens at Half Hollow

New Country Pointe Plainview

21105 ASPENWOOD DR # 275, PLAINVIEW, NY,..., Plainview, NY 11803

$1,300,000

2 beds

2 baths

1,475 sq ft

Condo

21105 ASPENWOOD DR # 275, PLAINVIEW, NY,...

Community: Country Pointe Plainview

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

Questions? Call us: (475) 244-9781

Overlook

4071 FAIRWAYS DR 136, CARMEL, NY, 10512, Carmel, NY 10512

$649,000

2 beds

3 baths

1,914 sq ft

Condo

4071 FAIRWAYS DR 136, CARMEL, NY, 10512

Community: Overlook

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

New Village Estates

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

$579,000

2 beds

1 baths

1,234 sq ft

Condo

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

Community: Village Estates

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

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

Questions? Call us: (475) 244-9781

New 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

New 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

Fairfield at St. James

304 GOTHAM WAY, SAINT JAMES, NY, 11780, Saint James, NY 11780

$449,803

1 beds

2 baths

Condo

304 GOTHAM WAY, SAINT JAMES, NY, 11780

Community: Fairfield at St. James

Village Estates

66 SARAH CT, AMITYVILLE, NY, 11701, Amityville, NY 11701

$499,000

2 beds

2 baths

1,243 sq ft

Condo

66 SARAH CT, AMITYVILLE, NY, 11701

Community: Village Estates

Leisure Glen

289 GLEN DR, RIDGE, NY, 11961, Ridge, NY 11961

$500,000

2 beds

2 baths

1,635 sq ft

Condo

289 GLEN DR, RIDGE, NY, 11961

Community: Leisure Glen

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

Questions? Call us: (475) 244-9781

New The Villas at Narragansett

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

$569,000

2 beds

2 baths

1,215 sq ft

Condo

816 NARRAGANSETT VILLAS DR # 816, LINDEN...

Community: The Villas at Narragansett

Fairfield at St. James

102 GOTHAM WAY, SAINT JAMES, NY, 11780, Saint James, NY 11780

$595,000

3 beds

3 baths

1,600 sq ft

Condo

102 GOTHAM WAY, SAINT JAMES, NY, 11780

Community: Fairfield at St. James

Fairfield at St. James

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

$599,995

1 beds

2 baths

1,236 sq ft

House

504 GOTHAM CT, SAINT JAMES, NY, 11780

Community: Fairfield at St. James

Heritage Hills

811 HERITAGE HLS, SOMERS, NY, 10589, Somers, NY 10589

$899,900

2 beds

2 baths

1,663 sq ft

Condo

811 HERITAGE HLS, SOMERS, NY, 10589

Community: Heritage Hills

New 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

Community: Leisure Village

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

Questions? Call us: (475) 244-9781

Leisure Knoll

195 CANTERBURY DR, RIDGE, NY, 11961, Ridge, NY 11961

$479,990

2 beds

1 baths

1,020 sq ft

Condo

195 CANTERBURY DR, RIDGE, NY, 11961

Community: Leisure Knoll

Jefferson Village

159 CARRIAGE CT C, YORKTOWN HEIGHTS, NY,..., Yorktown Heights, NY 10598

$560,000

2 beds

2 baths

1,300 sq ft

Condo

159 CARRIAGE CT C, YORKTOWN HEIGHTS, NY,...

Community: Jefferson Village

Jefferson Village

98 MOLLY PITCHER LN A, YORKTOWN HEIGHTS,..., Yorktown Heights, NY 10598

$525,000

2 beds

2 baths

1,100 sq ft

Condo

98 MOLLY PITCHER LN A, YORKTOWN HEIGHTS,...

Community: Jefferson Village

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

Questions? Call us: (475) 244-9781

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

Heritage Hills

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

$779,000

2 beds

2 baths

1,526 sq ft

Condo

749 HERITAGE HLS A, SOMERS, NY, 10589

Community: Heritage Hills

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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Cheshire, CT 55+ rental communities & homes for rent

1 communities near Cheshire

203 homes near Cheshire

2 beds

2 baths

1,610 sq ft

Condo

1 beds

2 baths

900 sq ft

Condo

2 beds

2 baths

1,050 sq ft

Condo

2 beds

2 baths

1,559 sq ft

Condo

2 beds

2 baths

1,050 sq ft

Condo

2 beds

1 baths

1,171 sq ft

Condo

2 beds

3 baths

1,900 sq ft

Condo

3 beds

3 baths

1,837 sq ft

Condo

2 beds

2 baths

938 sq ft

Condo

2 beds

2 baths

1,423 sq ft

Condo

2 beds

1 baths

875 sq ft

Condo

2 beds

2 baths

1,695 sq ft

Condo

2 beds

2 baths

935 sq ft

Condo

2 beds

2 baths

1,434 sq ft

Condo

3 beds

2 baths

1,689 sq ft

Condo

2 beds

2 baths

1,500 sq ft

Condo

2 beds

3 baths

1,957 sq ft

Condo

1 beds

1 baths

684 sq ft

Condo

2 beds

1 baths

1,000 sq ft

Condo

2 beds