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Connecticut 55+ active adult communities & homes for sale

Living in Connecticut

Connecticut offers a classic New England retirement lifestyle coupled with convenient regional access. Fairfield County and the New Haven shoreline sit closest to New York City,…

Connecticut offers a classic New England retirement lifestyle coupled with convenient regional access. Fairfield County and the New Haven shoreline sit closest to New York City, while Hartford-area towns are within driving distance of Boston. The scenic Long Island Sound shoreline runs the length of the state, and the Litchfield Hills provide a peaceful, rural alternative.

 Yale New Haven Health and Hartford HealthCare are two of the state's largest health systems. The state's four distinct seasons include New England's famous autumn foliage. Winters and home prices are real factors, so many buyers weigh staying close to family against a move to a warmer market.

Among Connecticut's senior housing and senior living options, 55 and over communities are designed for active adults who live independently. Connecticut is home to more than 60 active adult communities, with properties ranging from the mid-$100Ks to over $1M and averaging around $550K. Heritage Village in Southbury (2,580 homes) is the state's largest 55+ community.

Active adults seeking mid-sized options gravitate toward Oronoque Village in Stratford (929 homes) and Spring Lake Village in Southington (640 homes). Those prioritizing modern layouts favor new-construction neighborhoods like Chatfield Farms in Beacon Falls and The Village at Oxford Greens in Oxford.

55places has profiled every local development with verified pricing tiers, resident reviews, and direct local agent connections.

Quick Facts About Retiring in Connecticut


106 communities near Connecticut

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3.6 rating (7 reviews) Heritage Village
$200ks - $500ks
Heritage Village, Southbury, CT
Resale Only | 55+ age-restricted | Built 1967 - 2005 | 2,580 homes
The Village at Oxford Gre...
$400ks - $500ks
The Village at Oxford Gre..., Oxford, CT
New and Resale | 55+ age-restricted | Built 2004 - present | 835 homes
Fairview at Oxford Greens
$400ks - $600ks
Fairview at Oxford Greens, Oxford, CT
New and Resale | 55+ age-restricted | Built 2019 - present | 125 homes
5 rating (2 reviews) Oronoque Village
$200ks - $400ks
Oronoque Village, Stratford, CT
Resale Only | 55+ age-restricted | Built 1971 - 1977 | 929 homes
Rivington
$300ks - $900ks
Rivington, Danbury, CT
New and Resale | Age-targeted | Built 2006 - present | 1,050 homes
Want to learn more about 55+ communities in Connecticut? 55places can help!
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Spring Lake Village
$100ks - $200ks
Spring Lake Village, Southington, CT
Resale Only | 55+ age-restricted | Built 1970 - 2004 | 640 homes
4.9 rating (14 reviews) Chatfield Farms
$400ks - $700ks
Chatfield Farms, Beacon Falls, CT
New Construction | 55+ age-restricted | Built 2014 - present | 231 homes
Fieldstone Village
$500ks - $800ks
Fieldstone Village, Orange, CT
Resale Only | 55+ age-restricted | Built 2010 - 2018 | 142 homes
1 rating (1 review) Beckley Farms
$300ks - $400ks
Beckley Farms, Berlin, CT
New and Resale | 55+ age-restricted | Built 2010 - present | 170 homes
3.7 rating (3 reviews) Greenwood Village
$100ks
Greenwood Village, Manorville, NY
Resale Only | 55+ age-restricted | Built 1980 - 2000 | 512 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.
Leisure Glen
$300ks - $400ks
Leisure Glen, Ridge, NY
Resale Only | 55+ age-restricted | Built 1985 - 2010 | 646 homes
Leisure Village
$100ks - $300ks
Leisure Village, Ridge, NY
Resale Only | 55+ age-restricted | Built 1969 - 1986 | 1,500 homes
The Waterways at Moriches
$300ks - $600ks
The Waterways at Moriches, Moriches, NY
Resale Only | 55+ age-restricted | Built 1985 - 1999 | 343 homes
4 rating (8 reviews) Glenwood Village
$100ks - $200ks
Glenwood Village, Riverhead, NY
New and Resale | 55+ age-restricted | Built 1959 - present | 588 homes
The Greens at Half Hollow
$600ks - $1Ms
The Greens at Half Hollow, Melville, NY
Resale Only | 55+ age-restricted | Built 1994 - 2005 | 1,200 homes
Leisure Knoll
$200ks - $400ks
Leisure Knoll, Ridge, NY
Resale Only | 55+ age-restricted | Built 1972 - 1982 | 701 homes
Want to learn more about 55+ communities in Connecticut? 55places can help!
Questions? Call us: (888) 625-4885
Harmony Place
$400ks - $500ks
Harmony Place, Rutland, MA
New Construction | 55+ age-restricted | Built 2023 - present | 142 homes
Woodridge Strathmore Terr...
$200ks - $300ks
Woodridge Strathmore Terr..., Mount Sinai, NY
Resale Only | 55+ age-restricted | Built 1974 - 1985 | 226 homes
3.5 rating (2 reviews) Foxwood Village
$200ks - $400ks
Foxwood Village, Calverton, NY
Resale Only | 55+ age-restricted | Built 1986 - 2007 | 294 homes
1 rating (1 review) Plymouth Estates at Mount...
$400ks - $500ks
Plymouth Estates at Mount..., Mount Sinai, NY
Resale Only | 55+ age-restricted | Built 2006 - 2013 | 285 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.
Meadow Brook Estates
$300ks - $400ks
Meadow Brook Estates, Oxford, CT
Resale Only | 55+ age-restricted | Built 2003 - 2020 | 246 homes
5 rating (1 review) Newtown Woods
$300ks - $500ks
Newtown Woods, Newtown, CT
New and Resale | 55+ age-restricted | Built 2011 - present | 178 homes
Country Pointe Plainview
$700ks - $1Ms
Country Pointe Plainview, Plainview, NY
New Construction | 55+ age-restricted | Built 2017 - present | 660 homes
5 rating (1 review) Encore Atlantic Shores
$500ks - $800ks
Encore Atlantic Shores, Eastport, NY
Resale Only | 55+ age-restricted | Built 2004 - 2011 | 240 homes
5 rating (1 review) Westhampton Pines
$900ks - $1Ms
Westhampton Pines, Westhampton, NY
Resale Only | 55+ age-restricted | Built 2005 - 2013 | 189 homes
4.6 rating (9 reviews) Meadowbrook Pointe Links ...
$300ks - $700ks
Meadowbrook Pointe Links ..., Medford, NY
New and Resale | 55+ age-restricted | Built 2010 - present | 280 homes
Sonoma Woods
$300ks
Sonoma Woods, Middletown, CT
Resale Only | 55+ age-restricted | Built 2005 - 2015 | 68 homes
Want to learn more about 55+ communities in Connecticut? 55places can help!
Questions? Call us: (888) 625-4885
The Vineyards at Miller P...
$500ks
The Vineyards at Miller P..., Miller Place, NY
Resale Only | 55+ age-restricted | Built 2004 - 2005 | 85 homes
5 rating (1 review) Sunken Pond Estates
$400ks
Sunken Pond Estates, Riverhead, NY
Resale Only | 55+ age-restricted | Built 2003 - 2005 | 194 homes
Saddle Lakes
$400ks - $500ks
Saddle Lakes, Riverhead, NY
Resale Only | 55+ age-restricted | Built 2000 - 2002 | 196 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.
Kensington Estates
$1Ms
Kensington Estates, Woodbury, NY
New Construction | 55+ age-restricted | Built 2019 - 2021 | 80 homes
Stoneleigh Woods at River...
$500ks
Stoneleigh Woods at River..., Riverhead, NY
Resale Only | 55+ age-restricted | Built 2007 - 2016 | 176 homes
Pond Spring Village
$300ks
Pond Spring Village, Beacon Falls, CT
New and Resale | 55+ age-restricted | Built 2005 - present | 92 homes
Windcrest East
$400ks - $500ks
Windcrest East, Calverton, NY
Resale Only | 55+ age-restricted | Built 2004 - 2005 | 126 homes
5 rating (1 review) Encore at Lake Grove
$500ks - $700ks
Encore at Lake Grove, Lake Grove, NY
Resale Only | 55+ age-restricted | Built 2006 - 2007 | 228 homes
5 rating (2 reviews) Fairfield at St. James
$300ks - $500ks
Fairfield at St. James, St. James, NY
Resale Only | 55+ age-restricted | Built 1972 - 1989 | 653 homes
Liberty at Newtown
$300ks - $400ks
Liberty at Newtown, Newtown, CT
Resale Only | 55+ age-restricted | Built 2003 - 2007 | 96 homes
Regency at Woodbridge
$500ks - $700ks
Regency at Woodbridge, Woodbridge, CT
New Construction | 55+ age-restricted | Built 2023 - present | 70 homes
Want to learn more about 55+ communities in Connecticut? 55places can help!
Questions? Call us: (888) 625-4885
12...3
Greenwood Village 5107 VILLAGE CIR, BROOKHAVEN, NY, 11949, Brookhaven, NY 11949
$265,000

2 beds

|

2 baths

|

1,123 sq ft

|

Condo

5107 VILLAGE CIR, BROOKHAVEN, NY, 11949
Community: Greenwood Village
Greenwood Village 5147 VILLAGE CIR, BROOKHAVEN, NY, 11949, Brookhaven, NY 11949
$247,500

2 beds

|

2 baths

|

1,592 sq ft

|

Condo

5147 VILLAGE CIR, BROOKHAVEN, NY, 11949
Community: Greenwood Village
Leisure Village 177 VENTRY CT A, BROOKHAVEN, NY, 11961, Brookhaven, NY 11961
$449,500

2 beds

|

1 baths

|

1,085 sq ft

|

Condo

177 VENTRY CT A, BROOKHAVEN, NY, 11961
Community: Leisure Village
Greenwood Village 201 VILLAGE CIR, BROOKHAVEN, NY, 11949, Brookhaven, NY 11949
$250,000

2 beds

|

2 baths

|

1,078 sq ft

|

Condo

201 VILLAGE CIR, BROOKHAVEN, NY, 11949
Community: Greenwood Village
New Leisure Village 348 WOODBRIDGE DR B, BROOKHAVEN, NY, 119..., Brookhaven, NY 11961
$379,000

2 beds

|

2 baths

|

1,168 sq ft

|

Condo

348 WOODBRIDGE DR B, BROOKHAVEN, NY, 119...
Community: Leisure Village
Want to learn more about 55+ communities in Connecticut? 55places can help!
Questions? Call us: (888) 625-4885
New Sonoma Woods 19 SONOMA LN 19, MIDDLETOWN, CT, 06457, Middletown, CT 06457
$584,900

2 beds

|

2 baths

|

1,822 sq ft

|

Condo

19 SONOMA LN 19, MIDDLETOWN, CT, 06457
Community: Sonoma Woods
New Heritage Village 102 HERITAGE VLG A, SOUTHBURY, CT, 06488, Southbury, CT 06488
$237,500

1 beds

|

1 baths

|

928 sq ft

|

Condo

102 HERITAGE VLG A, SOUTHBURY, CT, 06488
Community: Heritage Village
New Country Pointe Plainview 21201 ASPENWOOD DR 276, OYSTER BAY, NY, ..., Oyster Bay, NY 11803
$1,250,000

2 beds

|

2 baths

|

1,379 sq ft

|

Condo

21201 ASPENWOOD DR 276, OYSTER BAY, NY, ...
New Leisure Village 412 WEYMOUTH CT B, BROOKHAVEN, NY, 11961, Brookhaven, NY 11961
$415,000

2 beds

|

1 baths

|

1,036 sq ft

|

House

412 WEYMOUTH CT B, BROOKHAVEN, NY, 11961
Community: Leisure Village
New Glenwood Village 1661 OLD COUNTRY RD 30, RIVERHEAD, NY, 1..., Riverhead, NY 11901
$100,000

2 beds

|

1 baths

|

720 sq ft

|

Mobile Home

1661 OLD COUNTRY RD 30, RIVERHEAD, NY, 1...
Community: Glenwood 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.
New Hopmeadow Place 1 W ST 120, SIMSBURY, CT, 06070, Simsbury, CT 06070
$385,000

2 beds

|

2 baths

|

1,477 sq ft

|

Condo

1 W ST 120, SIMSBURY, CT, 06070
Community: Hopmeadow Place
New The Waterways at Moriches 527 HIGHLAND CT, BROOKHAVEN, NY, 11955, Brookhaven, NY 11955
$599,000

2 beds

|

3 baths

|

1,988 sq ft

|

Condo

527 HIGHLAND CT, BROOKHAVEN, NY, 11955
New Leisure Village 8 GUILFORD CT A, BROOKHAVEN, NY, 11961, Brookhaven, NY 11961
$388,000

2 beds

|

1 baths

|

1,085 sq ft

|

Condo

8 GUILFORD CT A, BROOKHAVEN, NY, 11961
Community: Leisure Village
New The Greens at Half Hollow 603 BARDINI DR, HUNTINGTON, NY, 11747, Huntington, NY 11747
$1,349,999

3 beds

|

3 baths

|

2,500 sq ft

|

Condo

603 BARDINI DR, HUNTINGTON, NY, 11747
New Country Village Estates 44 THEODORE DR, BROOKHAVEN, NY, 11727, Brookhaven, NY 11727
$490,000

2 beds

|

2 baths

|

1,386 sq ft

|

Condo

44 THEODORE DR, BROOKHAVEN, NY, 11727
New Oak Meadow Estates 25 OAK MEADOW LN 25, TORRINGTON, CT, 067..., Torrington, CT 06790
$444,900

2 beds

|

3 baths

|

2,164 sq ft

|

Condo

25 OAK MEADOW LN 25, TORRINGTON, CT, 067...
Community: Oak Meadow Estates
Want to learn more about 55+ communities in Connecticut? 55places can help!
Questions? Call us: (888) 625-4885
New Long Hill Village 71 CIDER MILL LN, TRUMBULL, CT, 06611, Trumbull, CT 06611
$595,000

1 beds

|

3 baths

|

2,660 sq ft

|

Condo

71 CIDER MILL LN, TRUMBULL, CT, 06611
Community: Long Hill Village
New Spring Lake Village 504 CARRIAGE DR 504, SOUTHINGTON, CT, 06..., Southington, CT 06489
$319,900

2 beds

|

2 baths

|

1,313 sq ft

|

Condo

504 CARRIAGE DR 504, SOUTHINGTON, CT, 06...
Community: Spring Lake Village
Oronoque Village 161 BISON LN A, STRATFORD, CT, 06614, Stratford, CT 06614
$575,000

2 beds

|

3 baths

|

1,426 sq ft

|

Condo

161 BISON LN A, STRATFORD, CT, 06614
Community: Oronoque Village
Chatfield Farms 6 FIELDSTONE LN 6, BEACON FALLS, CT, 064..., Beacon Falls, CT 06403
$639,000

2 beds

|

3 baths

|

2,184 sq ft

|

Condo

6 FIELDSTONE LN 6, BEACON FALLS, CT, 064...
Community: Chatfield Farms
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.
Saddle Lakes 176 SCENIC LAKE DR, RIVERHEAD, NY, 11901, Riverhead, NY 11901
$575,000

2 beds

|

2 baths

|

1,247 sq ft

|

Condo

176 SCENIC LAKE DR, RIVERHEAD, NY, 11901
Community: Saddle Lakes
Pond Spring Village 127 PONDVIEW CIR 127, BEACON FALLS, CT, ..., Beacon Falls, CT 06403
$465,000

2 beds

|

3 baths

|

1,328 sq ft

|

Condo

127 PONDVIEW CIR 127, BEACON FALLS, CT, ...
Community: Pond Spring Village
Glenwood Village 1661 OLD COUNTRY RD 77, RIVERHEAD, NY, 1..., Riverhead, NY 11901
$289,000

2 beds

|

2 baths

|

1,248 sq ft

|

Manufactured Home

1661 OLD COUNTRY RD 77, RIVERHEAD, NY, 1...
Community: Glenwood Village
Leisure Glen 8 FLANDERS CT, BROOKHAVEN, NY, 11961, Brookhaven, NY 11961
$559,000

2 beds

|

2 baths

|

1,212 sq ft

|

Condo

8 FLANDERS CT, BROOKHAVEN, NY, 11961
Community: Leisure Glen
Long Hill Village 36 CIDER MILL LN, TRUMBULL, CT, 06611, Trumbull, CT 06611
$525,000

2 beds

|

2 baths

|

1,370 sq ft

|

Condo

36 CIDER MILL LN, TRUMBULL, CT, 06611
Community: Long Hill Village
Encore at Lake Grove 9 SONATA CT, SMITHTOWN, NY, 11755, Smithtown, NY 11755
$599,000

2 beds

|

2 baths

|

1,685 sq ft

|

Condo

9 SONATA CT, SMITHTOWN, NY, 11755
Plymouth Estates at Mount Sinai 53 ROSE LN, BROOKHAVEN, NY, 11766, Brookhaven, NY 11766
$499,999

2 beds

|

2 baths

|

1,272 sq ft

|

Condo

53 ROSE LN, BROOKHAVEN, NY, 11766
Want to learn more about 55+ communities in Connecticut? 55places can help!
Questions? Call us: (888) 625-4885
Sunken Pond Estates 1504 PEBBLE BEACH PATH, RIVERHEAD, NY, 1..., Riverhead, NY 11901
$545,000

2 beds

|

2 baths

|

1,258 sq ft

|

Condo

1504 PEBBLE BEACH PATH, RIVERHEAD, NY, 1...
Community: Sunken Pond Estates
Greenwood Village 33A LIMETREE DR, BROOKHAVEN, NY, 11949, Brookhaven, NY 11949
$144,999

2 beds

|

1 baths

|

800 sq ft

|

House

33A LIMETREE DR, BROOKHAVEN, NY, 11949
Community: Greenwood Village
Glenwood Village 1661 OLD COUNTRY RD 291, RIVERHEAD, NY, ..., Riverhead, NY 11901
$259,000

2 beds

|

2 baths

|

1,200 sq ft

|

Mobile Home

1661 OLD COUNTRY RD 291, RIVERHEAD, NY, ...
Community: Glenwood 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.
Woodridge Strathmore Terrace 74 HEARTHSIDE DR, BROOKHAVEN, NY, 11766, Brookhaven, NY 11766
$549,990

2 beds

|

2 baths

|

1,240 sq ft

|

Condo

74 HEARTHSIDE DR, BROOKHAVEN, NY, 11766
Woodridge Strathmore Terrace 9 CHIPPENDALE DR, BROOKHAVEN, NY, 11766, Brookhaven, NY 11766
$439,000

2 beds

|

2 baths

|

1,240 sq ft

|

Condo

9 CHIPPENDALE DR, BROOKHAVEN, NY, 11766
Rivington 79 WINDING RIDGE WAY 79, DANBURY, CT, 06..., Danbury, CT 06810
$1,112,000

3 beds

|

4 baths

|

2,596 sq ft

|

Condo

79 WINDING RIDGE WAY 79, DANBURY, CT, 06...
Community: Rivington
Spring Lake Village 261 CARRIAGE DR 261, SOUTHINGTON, CT, 06..., Southington, CT 06489
$375,000

2 beds

|

2 baths

|

1,207 sq ft

|

Condo

261 CARRIAGE DR 261, SOUTHINGTON, CT, 06...
Community: Spring Lake Village
The Powder Forest Homes 4 ASHTON CIR 4, SIMSBURY, CT, 06070, Simsbury, CT 06070
$729,000

3 beds

|

4 baths

|

2,381 sq ft

4 ASHTON CIR 4, SIMSBURY, CT, 06070
Leisure Knoll 259 EDINBURGH DR, BROOKHAVEN, NY, 11961, Brookhaven, NY 11961
$599,000

2 beds

|

2 baths

|

1,135 sq ft

|

Condo

259 EDINBURGH DR, BROOKHAVEN, NY, 11961
Community: Leisure Knoll
Stoneleigh Woods at Riverhead 47 STONELEIGH DR, RIVERHEAD, NY, 11901, Riverhead, NY 11901
$599,999

2 beds

|

3 baths

|

1,942 sq ft

|

Condo

47 STONELEIGH DR, RIVERHEAD, NY, 11901
Plymouth Estates at Mount Sinai 262 POND CIR 262, BROOKHAVEN, NY, 11766, Brookhaven, NY 11766
$599,000

2 beds

|

2 baths

|

1,820 sq ft

|

Condo

262 POND CIR 262, BROOKHAVEN, NY, 11766
Want to learn more about 55+ communities in Connecticut? 55places can help!
Questions? Call us: (888) 625-4885
Foxwood Village 1407 MIDDLE RD 103, RIVERHEAD, NY, 11933, Riverhead, NY 11933
$449,000

2 beds

|

2 baths

|

1,586 sq ft

|

Manufactured Home

1407 MIDDLE RD 103, RIVERHEAD, NY, 11933
Community: Foxwood Village
Foxwood Village 1407 MIDDLE RD 233, RIVERHEAD, NY, 11933, Riverhead, NY 11933
$405,000

3 beds

|

2 baths

|

1,792 sq ft

|

House

1407 MIDDLE RD 233, RIVERHEAD, NY, 11933
Community: Foxwood 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.



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© 2026 REIN. REIN's listings Data and information is protected under federal copyright laws. Federal law prohibits, among other acts, the unauthorized copying or alteration of, or preparation of derivative works from, all or any part of copyrighted materials, including certain compilations of Data and information. COPYRIGHT VIOLATORS MAY BE SUBJECT TO SEVERE FINES AND PENALTIES UNDER FEDERAL LAW.
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This application does not include information on all of the properties available for sale at this time.

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