Cheshire, CT 55+ active adult communities & homes for sale - Page 4

129 communities near Cheshire

Sort by:

Relevance

5 rating (1 reviews)

Sunrise Village

$400Ks - $500Ks

Sunrise Village, Sayville, NY

Resale Only | 55+ age-restricted | Built 1985 - 1990 | 213 homes

Windcrest East

$600Ks

Windcrest East, Calverton, NY

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

Windmill Gate

$300Ks - $400Ks

Windmill Gate, Oakdale, NY

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

Woodridge Strathmore Terr...

$400Ks

Woodridge Strathmore Terr..., Mount Sinai, NY

Resale Only | 55+ age-restricted | Built 1974 - 1985 | 226 homes

The Club at Melville

$500Ks

The Club at Melville, Melville, NY

Resale Only | 55+ age-restricted | Built 2015 - 2017 | 261 homes

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

The Seasons at Seaford

$700Ks

The Seasons at Seaford, Seaford, NY

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

4 rating (1 reviews)

Vineyards at Blue Point

$800Ks

Vineyards at Blue Point, Blue Point, NY

Resale Only | 55+ age-restricted | Built 2016 - 2018 | 280 homes

Knickerbocker Bay Club

$700Ks - $3Ms

Knickerbocker Bay Club, Port Washington, NY

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

3.5 rating (2 reviews)

Harvest Pointe

$800Ks - $3Ms

Harvest Pointe, Cutchogue, NY

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

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

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

Questions? Call us: (475) 244-9781

1 2 3 4

Heritage Hills

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

$414,900

1 beds

1 baths

1,055 sq ft

Condo

129 HERITAGE HLS A, SOMERS, NY, 10589

Community: Heritage Hills

Rivington

$499,900

2 beds

2 baths

1,229 sq ft

Condo

1 RIVINGTON WAY UNIT 201, DANBURY, CT, 0...

Community: Rivington

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

Heritage Village

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

$259,900

2 beds

2 baths

1,365 sq ft

Condo

723 HERITAGE VLG A, SOUTHBURY, CT, 06488

Community: Heritage Village

Greenwood Village

91 VILLAGE CIR, MANORVILLE, NY, 11949, Manorville, NY 11949

$155,000

2 beds

2 baths

938 sq ft

Condo

91 VILLAGE CIR, MANORVILLE, NY, 11949

Community: Greenwood Village

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

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

175 LONG HILL DR B, YORKTOWN HEIGHTS, NY..., Yorktown Heights, NY 10598

$399,999

2 beds

2 baths

1,159 sq ft

Condo

175 LONG HILL DR B, YORKTOWN HEIGHTS, NY...

Community: Jefferson Village

Oronoque Village

87 CREEK LN A, STRATFORD, CT, 06614, Stratford, CT 06614

$420,000

1 beds

2 baths

1,454 sq ft

Condo

87 CREEK LN A, STRATFORD, CT, 06614

Community: Oronoque Village

Oronoque Village

35 ALGONQUIN LN D, STRATFORD, CT, 06614, Stratford, CT 06614

$399,000

2 beds

2 baths

1,300 sq ft

Condo

35 ALGONQUIN LN D, STRATFORD, CT, 06614

Community: Oronoque Village

Jefferson Village

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

$549,999

2 beds

2 baths

1,300 sq ft

Condo

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

Community: Jefferson Village

Plymouth Estates at Mount Sinai

230 IRA RD # 230, MOUNT SINAI, NY, 11766, Mount Sinai, NY 11766

$589,999

2 beds

2 baths

1,317 sq ft

Condo

230 IRA RD # 230, MOUNT SINAI, NY, 11766

Community: Plymouth Estates at Mount Sinai

Oronoque Village

164 BISON LN A, STRATFORD, CT, 06614, Stratford, CT 06614

$465,000

1 beds

2 baths

1,175 sq ft

Condo

164 BISON LN A, STRATFORD, CT, 06614

Community: Oronoque Village

Newtown Woods

433 BROOKSIDE CT 433, NEWTOWN, CT, 06470, Newtown, CT 06470

$500,000

2 beds

2 baths

1,504 sq ft

Condo

433 BROOKSIDE CT 433, NEWTOWN, CT, 06470

Community: Newtown Woods

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

Questions? Call us: (475) 244-9781

Heritage Village

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

$356,000

2 beds

2 baths

1,398 sq ft

Condo

876 HERITAGE VLG A, SOUTHBURY, CT, 06488

Community: Heritage Village

Heritage Village

39 HERITAGE VLG C, SOUTHBURY, CT, 06488, Southbury, CT 06488

$238,000

2 beds

2 baths

1,044 sq ft

Condo

39 HERITAGE VLG C, SOUTHBURY, CT, 06488

Community: Heritage Village

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

Questions? Call us: (475) 244-9781

Heritage Village

865 HERITAGE VLG B, SOUTHBURY, CT, 06488, Southbury, CT 06488

$359,900

2 beds

2 baths

1,398 sq ft

Condo

865 HERITAGE VLG B, SOUTHBURY, CT, 06488

Community: Heritage Village

Oronoque Village

289 AGAWAM DR B, STRATFORD, CT, 06614, Stratford, CT 06614

$639,900

1 beds

3 baths

1,620 sq ft

Condo

289 AGAWAM DR B, STRATFORD, CT, 06614

Community: Oronoque Village

Greenwood Village

19 DOGWOOD LN, MANORVILLE, NY, 11949, Manorville, NY 11949

$149,900

2 beds

2 baths

871 sq ft

Condo

19 DOGWOOD LN, MANORVILLE, NY, 11949

Community: Greenwood 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

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

Heritage Village

929 HERITAGE VLG B, SOUTHBURY, CT, 06488, Southbury, CT 06488

$499,900

3 beds

2 baths

1,716 sq ft

Condo

929 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

Heritage Village

701 HERITAGE VLG B, SOUTHBURY, CT, 06488, Southbury, CT 06488

$329,000

3 beds

2 baths

1,716 sq ft

Condo

701 HERITAGE VLG B, SOUTHBURY, CT, 06488

Community: Heritage Village

Heritage Village

889 HERITAGE VLG B, SOUTHBURY, CT, 06488, Southbury, CT 06488

$374,500

2 beds

2 baths

1,398 sq ft

Condo

889 HERITAGE VLG B, SOUTHBURY, CT, 06488

Community: Heritage Village

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

The Village at Oxford Greens

413 MULLIGAN DR # 413, OXFORD, CT, 06478, Oxford, CT 06478

$519,000

2 beds

2 baths

1,590 sq ft

Condo

413 MULLIGAN DR # 413, OXFORD, CT, 06478

Community: The Village at Oxford Greens

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

Questions? Call us: (475) 244-9781

The Waterways at Moriches

414 LINDSAY LN, MORICHES, NY, 11955, Moriches, NY 11955

$535,000

2 beds

2 baths

2,141 sq ft

Condo

414 LINDSAY LN, MORICHES, NY, 11955

Community: The Waterways at Moriches

Heritage Village

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

$309,900

2 beds

2 baths

1,044 sq ft

Condo

98 HERITAGE VLG D, SOUTHBURY, CT, 06488

Community: Heritage Village

Strathmore Gate East

141 FORGE LN, CORAM, NY, 11727, Coram, NY 11727

$319,000

1 beds

1 baths

728 sq ft

Condo

141 FORGE LN, CORAM, NY, 11727

Community: Strathmore Gate East

The Village at Oxford Greens

930 TILLINGHAST DR # 930, OXFORD, CT, 06..., Oxford, CT 06478

$745,000

2 beds

3 baths

2,365 sq ft

930 TILLINGHAST DR # 930, OXFORD, CT, 06...

Community: The Village at Oxford Greens

Heritage Village

73 HERITAGE VLG C, SOUTHBURY, CT, 06488, Southbury, CT 06488

$214,900

2 beds

2 baths

1,044 sq ft

Condo

73 HERITAGE VLG C, SOUTHBURY, CT, 06488

Community: Heritage Village

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

Questions? Call us: (475) 244-9781

Heritage Village

60 HERITAGE VLG B, SOUTHBURY, CT, 06488, Southbury, CT 06488

$279,900

2 beds

2 baths

1,365 sq ft

Condo

60 HERITAGE VLG B, SOUTHBURY, CT, 06488

Community: Heritage Village

Heritage Hills

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

$750,000

2 beds

2 baths

1,435 sq ft

Condo

356 HERITAGE HLS A, SOMERS, NY, 10589

Community: Heritage Hills

Evergreen

34 WOODSBORO CIR # 34, CROMWELL, CT, 064..., Cromwell, CT 06416

$519,900

2 beds

2 baths

1,758 sq ft

Condo

34 WOODSBORO CIR # 34, CROMWELL, CT, 064...

Community: Evergreen

Fieldstone Village

206 DEERFIELD LN # 206, ORANGE, CT, 0647..., Orange, CT 06477

$760,000

2 beds

3 baths

1,650 sq ft

Condo

206 DEERFIELD LN # 206, ORANGE, CT, 0647...

Community: Fieldstone Village

Kensington Estates

46 PLAINVIEW RD, WOODBURY, NY, 11797, Woodbury, NY 11797

$2,299,999

6 beds

5 baths

4,333 sq ft

House

46 PLAINVIEW RD, WOODBURY, NY, 11797

Community: Kensington Estates

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

Questions? Call us: (475) 244-9781

Heritage Village

1008 HERITAGE VLG B, SOUTHBURY, CT, 0648..., Southbury, CT 06488

$385,000

2 beds

2 baths

1,432 sq ft

Condo

1008 HERITAGE VLG B, SOUTHBURY, CT, 0648...

Community: Heritage Village

The Village at Oxford Greens

709 CHAMPIONSHIP DR # 709, OXFORD, CT, 0..., Oxford, CT 06478

$615,000

2 beds

2 baths

1,532 sq ft

Condo

709 CHAMPIONSHIP DR # 709, OXFORD, CT, 0...

Community: The Village at Oxford Greens

Fairview at Oxford Greens

$615,000

2 beds

2 baths

1,532 sq ft

Condo

709 CHAMPIONSHIP DR # 709, OXFORD, CT, 0...

Community: Fairview at Oxford Greens

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

Questions? Call us: (475) 244-9781

The Woods at Dunham Pond

12 HERON VIEW RD # 12, NEW FAIRFIELD, CT..., New Fairfield, CT 06812

$409,900

1 beds

2 baths

1,550 sq ft

12 HERON VIEW RD # 12, NEW FAIRFIELD, CT...

Community: The Woods at Dunham Pond

Park Glen

1 BLOSSOM CT # 1, NEW MILFORD, CT, 06776, New Milford, CT 06776

$545,000

2 beds

2 baths

1,880 sq ft

Condo

1 BLOSSOM CT # 1, NEW MILFORD, CT, 06776

Community: Park Glen

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?

Global - Lead Form - Buyer or Renter

First Name

Last Name

Phone/Mobile

Text

I'm looking to:

Rent

Buy

*55places does not provide or maintain community HOA information.

Yes, I want to subscribe to email updates from 55places.com, including newsletters, community announcements, and more.

I agree to receive SMS messages to connect me with a local expert.

By requesting more information, you agree that 55places may call, text, or email you about your inquiry, which may be made with automated means (including recorded voice messages, SMS, or text messages). You understand that your consent is not a prerequisite for buying, selling or renting a property. You may revoke your consent at any time by contacting [email protected]. Message/data rates may apply. You also agree to 55places.com’s Privacy Policy and Terms of Use.

Want to learn more about 55+ communities in Cheshire?

Call us: (475) 244-9781

129 communities

Remove Boundaries ×

Map Satellite

Cheshire, CT 55+ active adult communities & homes for sale - Page 4

129 communities near Cheshire

224 homes near Cheshire

1 beds

1 baths

1,055 sq ft

Condo

2 beds

2 baths

1,229 sq ft

Condo

2 beds

3 baths

1,900 sq ft

Condo

2 beds

2 baths

1,365 sq ft

Condo

2 beds

2 baths

938 sq ft

Condo

1 beds

2 baths

900 sq ft

Condo

2 beds

2 baths

1,159 sq ft

Condo

1 beds

2 baths

1,454 sq ft

Condo

2 beds

2 baths

1,300 sq ft

Condo

2 beds

2 baths

1,300 sq ft

Condo

2 beds

2 baths

1,317 sq ft

Condo

1 beds

2 baths

1,175 sq ft

Condo

2 beds

2 baths

1,504 sq ft

Condo

2 beds

2 baths

1,398 sq ft

Condo

2 beds

2 baths

1,044 sq ft

Condo

2 beds

2 baths

1,398 sq ft

Condo

1 beds

3 baths

1,620 sq ft

Condo

2 beds

2 baths

871 sq ft

Condo

2 beds

2 baths

1,100 sq ft

Condo

2 beds