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Connecticut 55+ rental communities & homes for rent

Living in Connecticut

Connecticut offers a classic New England retirement lifestyle coupled with unparalleled regional access — New York City and Boston are each under two hours away, the scenic Long…
Connecticut offers a classic New England retirement lifestyle coupled with unparalleled regional access — New York City and Boston are each under two hours away, the scenic Long Island Sound shoreline runs the length of the state, and the Litchfield Hills provide a peaceful, rural alternative. The state boasts an exceptional healthcare network, anchored by Yale New Haven Health and Hartford HealthCare, alongside four distinct seasons featuring world-renowned autumn foliage.Connecticut is home to 62 active adult communities, with properties ranging from the mid-$100Ks to over $1M and averaging around $547K. Heritage Village in Southbury (2,580 homes) is the crown jewel of the state — ranking as one of the largest and most established 55+ communities in all of New England. Active adults seeking mid-sized options gravitate toward Oronoque Village in Stratford (929 homes) and Spring Lake Village in Southington (640 homes), while those prioritizing modern layouts favor new construction neighborhoods like Chatfield Farms in Beacon Falls and The Village at Oxford Greens in Oxford. 55places has thoroughly profiled every local development with verified pricing tiers, honest resident reviews, and direct local agent connections.

Quick Facts About Retiring in Connecticut


1 communities near Connecticut

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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.
The Cornerstone at Hauppa...
$3,511.06 - $3,981.06 / mo
Base rent from $3,430
The Cornerstone at Hauppa..., Hauppauge, NY
New Construction | 55+ age-restricted | Built 2019 - 2020 | 96 rental homes
Want to learn more about 55+ rental communities in Connecticut? 55places can help!
Questions? Call us: (888) 625-4885
Heritage Village 345 HERITAGE VLG A, SOUTHBURY, CT, 06488, Southbury, CT 06488
$386,000

3 beds

|

2 baths

|

1,716 sq ft

|

Condo

345 HERITAGE VLG A, SOUTHBURY, CT, 06488
Community: Heritage Village
Greenwood Village 105 W VILLAGE CIR 105, BROOKHAVEN, NY, 1..., Brookhaven, NY 11949
$245,000

2 beds

|

2 baths

|

1,130 sq ft

|

Condo

105 W VILLAGE CIR 105, BROOKHAVEN, NY, 1...
Community: Greenwood Village
Glenwood Village 1661 OLD COUNTRY RD 516, RIVERHEAD, NY, ..., Riverhead, NY 11901
$419,000

2 beds

|

2 baths

|

1,624 sq ft

|

Manufactured Home

1661 OLD COUNTRY RD 516, RIVERHEAD, NY, ...
Community: Glenwood Village
New Rivington 714 CENTER MEADOW LN 714, DANBURY, CT, 0..., Danbury, CT 06810
$497,000

2 beds

|

2 baths

|

1,258 sq ft

|

Condo

714 CENTER MEADOW LN 714, DANBURY, CT, 0...
Community: Rivington
New Eagles Walk at East Quogue 1401 AERIE WAY, SOUTHAMPTON, NY, 11942, Southampton, NY 11942
$565,000

2 beds

|

2 baths

|

1,271 sq ft

|

Condo

1401 AERIE WAY, SOUTHAMPTON, NY, 11942
Want to learn more about 55+ communities in Connecticut? 55places can help!
Questions? Call us: (888) 625-4885
New Heritage Village 397 HERITAGE VLG B, SOUTHBURY, CT, 06488, Southbury, CT 06488
$424,900

2 beds

|

2 baths

|

1,432 sq ft

|

Condo

397 HERITAGE VLG B, SOUTHBURY, CT, 06488
Community: Heritage Village
New Shaker Heights 12 COPLEY CIR 12, ENFIELD, CT, 06082, Enfield, CT 06082
$589,900

2 beds

|

2 baths

|

1,897 sq ft

|

Condo

12 COPLEY CIR 12, ENFIELD, CT, 06082
Community: Shaker Heights
New Founders Village 2555 YOUNGS AVE 3C, SOUTHOLD, NY, 11971, Southold, NY 11971
$550,000

2 beds

|

2 baths

|

1,100 sq ft

|

Condo

2555 YOUNGS AVE 3C, SOUTHOLD, NY, 11971
Community: Founders Village
New The Greens at Half Hollow 559 BARDINI DR, HUNTINGTON, NY, 11747, Huntington, NY 11747
$1,299,000

3 beds

|

3 baths

|

2,396 sq ft

|

Condo

559 BARDINI DR, HUNTINGTON, NY, 11747
New Leisure Knoll 185 KINGSTON DR, BROOKHAVEN, NY, 11961, Brookhaven, NY 11961
$405,000

2 beds

|

1 baths

|

1,014 sq ft

|

Condo

185 KINGSTON DR, BROOKHAVEN, NY, 11961
Community: Leisure Knoll
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.
New Heritage Village 549 HERITAGE VLG D, SOUTHBURY, CT, 06488, Southbury, CT 06488
$164,900

2 beds

|

2 baths

|

1,044 sq ft

|

Condo

549 HERITAGE VLG D, SOUTHBURY, CT, 06488
Community: Heritage Village
Kensington Estates 44 PLAINVIEW RD, OYSTER BAY, NY, 11797, Oyster Bay, NY 11797
$1,999,888

6 beds

|

5 baths

|

4,333 sq ft

|

House

44 PLAINVIEW RD, OYSTER BAY, NY, 11797
Community: Kensington Estates
Encore Atlantic Shores 101 MOZART CT, BROOKHAVEN, NY, 11941, Brookhaven, NY 11941
$779,000

2 beds

|

2 baths

|

2,044 sq ft

|

House

101 MOZART CT, BROOKHAVEN, NY, 11941
Heritage Village 1041 HERITAGE VLG A, SOUTHBURY, CT, 0648..., Southbury, CT 06488
$244,000

2 beds

|

2 baths

|

1,000 sq ft

|

Condo

1041 HERITAGE VLG A, SOUTHBURY, CT, 0648...
Community: Heritage Village
Rivington 12 OLD PASTURE DR 12, DANBURY, CT, 06810, Danbury, CT 06810
$839,000

3 beds

|

4 baths

|

1,794 sq ft

|

Condo

12 OLD PASTURE DR 12, DANBURY, CT, 06810
Community: Rivington
Greenwood Village 205 VILLAGE CIR, BROOKHAVEN, NY, 11949, Brookhaven, NY 11949
$125,000

2 beds

|

2 baths

|

1,138 sq ft

|

House

205 VILLAGE CIR, BROOKHAVEN, NY, 11949
Community: Greenwood Village
Want to learn more about 55+ communities in Connecticut? 55places can help!
Questions? Call us: (888) 625-4885
The Village at Oxford Greens 521 PUTTING GREEN LN 521, OXFORD, CT, 06..., Oxford, CT 06478
$675,000

3 beds

|

3 baths

|

2,735 sq ft

|

Condo

521 PUTTING GREEN LN 521, OXFORD, CT, 06...
Setauket Meadows 2 EMILYS WAY, BROOKHAVEN, NY, 11733, Brookhaven, NY 11733
$799,500

2 beds

|

3 baths

|

1,842 sq ft

|

Condo

2 EMILYS WAY, BROOKHAVEN, NY, 11733
Community: Setauket Meadows
Oronoque Village 546 N TRL A, STRATFORD, CT, 06614, Stratford, CT 06614
$539,000

2 beds

|

3 baths

|

1,434 sq ft

|

Condo

546 N TRL A, STRATFORD, CT, 06614
Community: Oronoque Village
The Greens at Half Hollow 1118 SAVOY DR, HUNTINGTON, NY, 11747, Huntington, NY 11747
$695,000

2 beds

|

2 baths

|

1,100 sq ft

|

Condo

1118 SAVOY DR, HUNTINGTON, NY, 11747
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.
Rivington 11 MERCY ST 11, DANBURY, CT, 06810, Danbury, CT 06810
$630,000

2 beds

|

4 baths

|

1,572 sq ft

|

Condo

11 MERCY ST 11, DANBURY, CT, 06810
Community: Rivington
Greenwood Village 162 VILLAGE CIR, BROOKHAVEN, NY, 11949, Brookhaven, NY 11949
$154,888

2 beds

|

2 baths

|

1,078 sq ft

|

Condo

162 VILLAGE CIR, BROOKHAVEN, NY, 11949
Community: Greenwood Village
Leisure Glen 272 GLEN DR, BROOKHAVEN, NY, 11961, Brookhaven, NY 11961
$549,000

2 beds

|

2 baths

|

1,456 sq ft

|

Condo

272 GLEN DR, BROOKHAVEN, NY, 11961
Community: Leisure Glen
Woodridge Strathmore Terrace 62 HEARTHSIDE DR, BROOKHAVEN, NY, 11766, Brookhaven, NY 11766
$425,000

2 beds

|

2 baths

|

1,105 sq ft

|

Condo

62 HEARTHSIDE DR, BROOKHAVEN, NY, 11766
Meadow Brook Estates 107 MEADOW BROOK RD 107, OXFORD, CT, 064..., Oxford, CT 06478
$639,000

3 beds

|

3 baths

|

1,922 sq ft

107 MEADOW BROOK RD 107, OXFORD, CT, 064...
The Powder Forest Homes 9 GRISWOLD PL 9, SIMSBURY, CT, 06070, Simsbury, CT 06070
$1,250,000

3 beds

|

5 baths

|

2,774 sq ft

9 GRISWOLD PL 9, SIMSBURY, CT, 06070
Heritage Village 65 HERITAGE VLG B, SOUTHBURY, CT, 06488, Southbury, CT 06488
$219,900

1 beds

|

1 baths

|

928 sq ft

|

Condo

65 HERITAGE VLG B, SOUTHBURY, CT, 06488
Community: Heritage Village
Want to learn more about 55+ communities in Connecticut? 55places can help!
Questions? Call us: (888) 625-4885
Heritage Village 261B HERITAGE VLG, SOUTHBURY, CT, 06488, Southbury, CT 06488
$260,000

2 beds

|

2 baths

|

1,032 sq ft

|

Condo

261B HERITAGE VLG, SOUTHBURY, CT, 06488
Community: Heritage Village
Westhampton Pines 179 CARLY LN, SOUTHAMPTON, NY, 11977, Southampton, NY 11977
$899,000

2 beds

|

2 baths

|

2,000 sq ft

|

Condo

179 CARLY LN, SOUTHAMPTON, NY, 11977
Community: Westhampton Pines
Heritage Village 1016 HERITAGE VLG A, SOUTHBURY, CT, 0648..., Southbury, CT 06488
$245,000

1 beds

|

1 baths

|

928 sq ft

|

Condo

1016 HERITAGE VLG A, SOUTHBURY, CT, 0648...
Community: Heritage Village
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.
Spring Lake Village 504 CARRIAGE DR 504, SOUTHINGTON, CT, 06..., Southington, CT 06489
$330,000

2 beds

|

2 baths

|

1,313 sq ft

|

Condo

504 CARRIAGE DR 504, SOUTHINGTON, CT, 06...
Community: Spring Lake Village
Stoneleigh Woods at Riverhead 158 STONELEIGH DR, RIVERHEAD, NY, 11901, Riverhead, NY 11901
$699,000

2 beds

|

3 baths

|

2,071 sq ft

|

Condo

158 STONELEIGH DR, RIVERHEAD, NY, 11901
Country Pointe Preserve 128 JUNIPER LN 26, BROOKHAVEN, NY, 11980, Brookhaven, NY 11980
$875,000

2 beds

|

3 baths

|

1,998 sq ft

|

Condo

128 JUNIPER LN 26, BROOKHAVEN, NY, 11980
Rivington 424 CENTER MEADOW LN 424, DANBURY, CT, 0..., Danbury, CT 06810
$479,900

2 beds

|

2 baths

|

1,258 sq ft

|

Condo

424 CENTER MEADOW LN 424, DANBURY, CT, 0...
Community: Rivington
Country Pointe Plainview 52102 BEECH TREE LN, OYSTER BAY, NY, 118..., Oyster Bay, NY 11803
$1,669,990

2 beds

|

3 baths

|

1,750 sq ft

|

Condo

52102 BEECH TREE LN, OYSTER BAY, NY, 118...
Glenwood Village 1661 OLD COUNTRY RD 454, RIVERHEAD, NY, ..., Riverhead, NY 11901
$329,000

2 beds

|

2 baths

|

1,152 sq ft

|

Manufactured Home

1661 OLD COUNTRY RD 454, RIVERHEAD, NY, ...
Community: Glenwood Village
Stone Ridge Estates 110 JOSEPH LN, HUNTINGTON, NY, 11746, Huntington, NY 11746
$779,000

2 beds

|

2 baths

|

1,695 sq ft

|

Condo

110 JOSEPH LN, HUNTINGTON, NY, 11746
Community: Stone Ridge Estates
Encore Atlantic Shores 140 CHOPIN PL, BROOKHAVEN, NY, 11941, Brookhaven, NY 11941
$865,000

2 beds

|

3 baths

|

2,236 sq ft

|

Condo

140 CHOPIN PL, BROOKHAVEN, NY, 11941
Want to learn more about 55+ communities in Connecticut? 55places can help!
Questions? Call us: (888) 625-4885
Leisure Village 89 ENFIELD CT B, BROOKHAVEN, NY, 11961, Brookhaven, NY 11961
$469,000

2 beds

|

2 baths

|

1,308 sq ft

|

Condo

89 ENFIELD CT B, BROOKHAVEN, NY, 11961
Community: Leisure Village
Village Vistas 35 THERESA LN, BROOKHAVEN, NY, 11777, Brookhaven, NY 11777
$1,300,000

3 beds

|

4 baths

|

3,000 sq ft

|

Condo

35 THERESA LN, BROOKHAVEN, NY, 11777
Community: Village Vistas
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.



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