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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
Leisure Knoll
$200ks - $400ks
Leisure Knoll, Ridge, NY
Resale Only | 55+ age-restricted | Built 1972 - 1982 | 701 homes
4 rating (8 reviews) Glenwood Village
$100ks - $200ks
Glenwood Village, Riverhead, NY
New and Resale | 55+ age-restricted | Built 1959 - present | 588 homes
Harmony Place
$400ks - $500ks
Harmony Place, Rutland, MA
New Construction | 55+ age-restricted | Built 2023 - present | 142 homes
Want to learn more about 55+ communities in Connecticut? 55places can help!
Questions? Call us: (888) 625-4885
3.5 rating (2 reviews) Foxwood Village
$200ks - $400ks
Foxwood Village, Calverton, NY
Resale Only | 55+ age-restricted | Built 1986 - 2007 | 294 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
5 rating (1 review) Sunken Pond Estates
$400ks
Sunken Pond Estates, Riverhead, NY
Resale Only | 55+ age-restricted | Built 2003 - 2005 | 194 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
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) Westhampton Pines
$900ks - $1Ms
Westhampton Pines, Westhampton, NY
Resale Only | 55+ age-restricted | Built 2005 - 2013 | 189 homes
5 rating (1 review) Newtown Woods
$300ks - $500ks
Newtown Woods, Newtown, CT
New and Resale | 55+ age-restricted | Built 2011 - present | 178 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
5 rating (1 review) Encore Atlantic Shores
$500ks - $800ks
Encore Atlantic Shores, Eastport, NY
Resale Only | 55+ age-restricted | Built 2004 - 2011 | 240 homes
Regency Meadows
$500ks
Regency Meadows, Trumbull, CT
Resale Only | 55+ age-restricted | Built 2003 - 2005 | 51 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
Woodridge Strathmore Terr...
$200ks - $300ks
Woodridge Strathmore Terr..., Mount Sinai, NY
Resale Only | 55+ age-restricted | Built 1974 - 1985 | 226 homes
Regency at Woodbridge
$500ks - $700ks
Regency at Woodbridge, Woodbridge, CT
New Construction | 55+ age-restricted | Built 2023 - present | 70 homes
Country Pointe Plainview
$700ks - $1Ms
Country Pointe Plainview, Plainview, NY
New Construction | 55+ age-restricted | Built 2017 - present | 660 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.
Windcrest East
$400ks - $500ks
Windcrest East, Calverton, NY
Resale Only | 55+ age-restricted | Built 2004 - 2005 | 126 homes
Liberty at Newtown
$300ks - $400ks
Liberty at Newtown, Newtown, CT
Resale Only | 55+ age-restricted | Built 2003 - 2007 | 96 homes
Saddle Lakes
$400ks - $500ks
Saddle Lakes, Riverhead, NY
Resale Only | 55+ age-restricted | Built 2000 - 2002 | 196 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
Billingsgate
$400ks - $600ks
Billingsgate, Simsbury, CT
Resale Only | 55+ age-restricted | Built 2003 - 2006 | 37 homes
Pond Spring Village
$300ks
Pond Spring Village, Beacon Falls, CT
New and Resale | 55+ age-restricted | Built 2005 - present | 92 homes
Stoneleigh Woods at River...
$500ks
Stoneleigh Woods at River..., Riverhead, NY
Resale Only | 55+ age-restricted | Built 2007 - 2016 | 176 homes
The Village at Buckingham
$300ks - $400ks
The Village at Buckingham, Avon, CT
Resale Only | 55+ age-restricted | Built 2002 - 2006 | 56 homes
Want to learn more about 55+ communities in Connecticut? 55places can help!
Questions? Call us: (888) 625-4885
12...3
New 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 Sonoma Woods 2 SONOMA LN 2, MIDDLETOWN, CT, 06457, Middletown, CT 06457
$549,900

2 beds

|

3 baths

|

1,903 sq ft

2 SONOMA LN 2, MIDDLETOWN, CT, 06457
Community: Sonoma Woods
New Leisure Knoll 434 KINGSTON DR 434, BROOKHAVEN, NY, 119..., Brookhaven, NY 11961
$499,000

2 beds

|

2 baths

|

1,646 sq ft

|

Condo

434 KINGSTON DR 434, BROOKHAVEN, NY, 119...
Community: Leisure Knoll
Want to learn more about 55+ communities in Connecticut? 55places can help!
Questions? Call us: (888) 625-4885
New The Villages at Mount Sinai Park 93 LOUDEN LOOP, BROOKHAVEN, NY, 11766, Brookhaven, NY 11766
$799,000

2 beds

|

2 baths

|

2,234 sq ft

|

House

93 LOUDEN LOOP, BROOKHAVEN, NY, 11766
New Leisure Glen 277 GLEN DR, BROOKHAVEN, NY, 11961, Brookhaven, NY 11961
$535,900

2 beds

|

2 baths

|

1,542 sq ft

|

Condo

277 GLEN DR, BROOKHAVEN, NY, 11961
Community: Leisure Glen
New Heritage Village 45 HERITAGE VLG A, SOUTHBURY, CT, 06488, Southbury, CT 06488
$289,900

2 beds

|

2 baths

|

1,032 sq ft

|

Condo

45 HERITAGE VLG A, SOUTHBURY, CT, 06488
Community: Heritage Village
New Heritage Village 198 HERITAGE VLG B, SOUTHBURY, CT, 06488, Southbury, CT 06488
$325,000

2 beds

|

2 baths

|

1,432 sq ft

|

Condo

198 HERITAGE VLG B, SOUTHBURY, CT, 06488
Community: Heritage Village
Meadowbrook Pointe Links & Spa 146 AUGUSTA DR, BROOKHAVEN, NY, 11763, Brookhaven, NY 11763
$800,000

2 beds

|

3 baths

|

2,047 sq ft

|

Condo

146 AUGUSTA DR, BROOKHAVEN, NY, 11763
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.
Strathmore Gate East 46 FORGE LN, BROOKHAVEN, NY, 11727, Brookhaven, NY 11727
$429,999

2 beds

|

2 baths

|

1,112 sq ft

|

Condo

46 FORGE LN, BROOKHAVEN, NY, 11727
Greenwood Village 40 GREENWOOD BLVD, BROOKHAVEN, NY, 11949, Brookhaven, NY 11949
$139,999

2 beds

|

1 baths

|

938 sq ft

|

Condo

40 GREENWOOD BLVD, BROOKHAVEN, NY, 11949
Community: Greenwood Village
Greenwood Village 5115 VILLAGE CIR, BROOKHAVEN, NY, 11949, Brookhaven, NY 11949
$299,999

2 beds

|

2 baths

|

1,134 sq ft

|

House

5115 VILLAGE CIR, BROOKHAVEN, NY, 11949
Community: Greenwood Village
The Greens at Half Hollow 387 ALTESSA BLVD, HUNTINGTON, NY, 11747, Huntington, NY 11747
$1,599,000

3 beds

|

3 baths

|

2,700 sq ft

|

Condo

387 ALTESSA BLVD, HUNTINGTON, NY, 11747
Heritage Village 62 HERITAGE VLG A, SOUTHBURY, CT, 06488, Southbury, CT 06488
$186,000

2 beds

|

2 baths

|

1,032 sq ft

|

Condo

62 HERITAGE VLG A, SOUTHBURY, CT, 06488
Community: Heritage Village
Oronoque Village 638 ONONDAGA LN A, STRATFORD, CT, 06614, Stratford, CT 06614
$499,000

1 beds

|

3 baths

|

1,175 sq ft

|

Condo

638 ONONDAGA LN A, STRATFORD, CT, 06614
Community: Oronoque Village
Want to learn more about 55+ communities in Connecticut? 55places can help!
Questions? Call us: (888) 625-4885
Pond Spring Village 41 PONDVIEW CIR 41, BEACON FALLS, CT, 06..., Beacon Falls, CT 06403
$485,000

2 beds

|

2 baths

|

1,501 sq ft

|

Condo

41 PONDVIEW CIR 41, BEACON FALLS, CT, 06...
Community: Pond Spring Village
Rivington 19 WARRINGTON ROUND 19, DANBURY, CT, 068..., Danbury, CT 06810
$749,000

3 beds

|

3 baths

|

2,196 sq ft

|

Condo

19 WARRINGTON ROUND 19, DANBURY, CT, 068...
Community: Rivington
Heritage Village 786 HERITAGE VLG C, SOUTHBURY, CT, 06488, Southbury, CT 06488
$295,000

2 beds

|

2 baths

|

1,000 sq ft

|

Condo

786 HERITAGE VLG C, SOUTHBURY, CT, 06488
Community: Heritage Village
Village Vistas 11 THERESA LN, BROOKHAVEN, NY, 11777, Brookhaven, NY 11777
$1,249,000

3 beds

|

4 baths

|

3,075 sq ft

|

Condo

11 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.
Evergreen 5 HARWOOD GDNS 5, CROMWELL, CT, 06416, Cromwell, CT 06416
$479,900

2 beds

|

2 baths

|

1,436 sq ft

|

Condo

5 HARWOOD GDNS 5, CROMWELL, CT, 06416
Community: Evergreen
Benson Woods 203 SUGAR MAPLE WAY 203, MIDDLEBURY, CT,..., Middlebury, CT 06762
$589,900

2 beds

|

3 baths

|

2,442 sq ft

|

Condo

203 SUGAR MAPLE WAY 203, MIDDLEBURY, CT,...
Community: Benson Woods
Leisure Village 379C WOODBRIDGE DR C, BROOKHAVEN, NY, 11..., Brookhaven, NY 11961
$459,900

2 beds

|

2 baths

|

1,168 sq ft

|

Condo

379C WOODBRIDGE DR C, BROOKHAVEN, NY, 11...
Community: Leisure Village
Leisure Glen 14 FLANDERS CT, BROOKHAVEN, NY, 11961, Brookhaven, NY 11961
$450,000

2 beds

|

2 baths

|

1,212 sq ft

|

House

14 FLANDERS CT, BROOKHAVEN, NY, 11961
Community: Leisure Glen
Heritage Village 219 HERITAGE VLG B, SOUTHBURY, CT, 06488, Southbury, CT 06488
$250,000

2 beds

|

2 baths

|

1,398 sq ft

|

Condo

219 HERITAGE VLG B, SOUTHBURY, CT, 06488
Community: Heritage Village
Heritage Village 974 HERITAGE VLG A, SOUTHBURY, CT, 06488, Southbury, CT 06488
$299,900

2 beds

|

2 baths

|

1,432 sq ft

|

Condo

974 HERITAGE VLG A, SOUTHBURY, CT, 06488
Community: Heritage Village
Heritage Village 847 HERITAGE VLG B, SOUTHBURY, CT, 06488, Southbury, CT 06488
$500,000

3 beds

|

2 baths

|

1,716 sq ft

|

Condo

847 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
Country Pointe Preserve 103 FOXWOOD DR 73, BROOKHAVEN, NY, 11980, Brookhaven, NY 11980
$935,000

2 beds

|

3 baths

|

2,187 sq ft

|

Condo

103 FOXWOOD DR 73, BROOKHAVEN, NY, 11980
Heritage Village 369 HERITAGE VLG A, SOUTHBURY, CT, 06488, Southbury, CT 06488
$185,000

1 beds

|

1 baths

|

928 sq ft

|

Condo

369 HERITAGE VLG A, SOUTHBURY, CT, 06488
Community: Heritage Village
Heritage Village 26 HERITAGE VLG A, SOUTHBURY, CT, 06488, Southbury, CT 06488
$379,900

2 beds

|

2 baths

|

1,432 sq ft

|

Condo

26 HERITAGE VLG A, SOUTHBURY, CT, 06488
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.
Heritage Village 24 HERITAGE CRST B, SOUTHBURY, CT, 06488, Southbury, CT 06488
$383,000

2 beds

|

2 baths

|

1,217 sq ft

|

Condo

24 HERITAGE CRST B, SOUTHBURY, CT, 06488
Community: Heritage Village
The Waterways at Moriches 129 CAPTAINS CT, BROOKHAVEN, NY, 11955, Brookhaven, NY 11955
$749,000

2 beds

|

2 baths

|

1,762 sq ft

|

Condo

129 CAPTAINS CT, BROOKHAVEN, NY, 11955
Rivington 42 COUNTRY VIEW RD 42, DANBURY, CT, 0681..., Danbury, CT 06810
$1,175,000

3 beds

|

4 baths

|

2,709 sq ft

|

Condo

42 COUNTRY VIEW RD 42, DANBURY, CT, 0681...
Community: Rivington
The Village at Buckingham 10 CHELSEA PL 10, AVON, CT, 06001, Avon, CT 06001
$614,900

3 beds

|

3 baths

|

2,430 sq ft

10 CHELSEA PL 10, AVON, CT, 06001
Sunken Pond Estates 1504 PEBBLE BEACH PATH, RIVERHEAD, NY, 1..., Riverhead, NY 11901
$545,000

2 beds

|

2 baths

|

1,258 sq ft

|

House

1504 PEBBLE BEACH PATH, RIVERHEAD, NY, 1...
Community: Sunken Pond Estates
Bidwell Village 94 STONEHOUSE RD 6, COVENTRY, CT, 06238, Coventry, CT 06238
$449,900

3 beds

|

3 baths

|

1,905 sq ft

|

Condo

94 STONEHOUSE RD 6, COVENTRY, CT, 06238
Community: Bidwell Village
The Waterways at Moriches 632 WATER WAY 32, BROOKHAVEN, NY, 11955, Brookhaven, NY 11955
$699,000

2 beds

|

3 baths

|

1,874 sq ft

|

Condo

632 WATER WAY 32, BROOKHAVEN, NY, 11955
Greenwood Village 205 VILLAGE CIR, BROOKHAVEN, NY, 11949, Brookhaven, NY 11949
$169,999

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
Heritage Village 191 HERITAGE VLG A, SOUTHBURY, CT, 06488, Southbury, CT 06488
$559,900

3 beds

|

2 baths

|

1,716 sq ft

|

Condo

191 HERITAGE VLG A, SOUTHBURY, CT, 06488
Community: Heritage Village
Liberty at Newtown 22 FRANKLIN CT 22, NEWTOWN, CT, 06470, Newtown, CT 06470
$599,000

2 beds

|

3 baths

|

2,341 sq ft

|

Condo

22 FRANKLIN CT 22, NEWTOWN, CT, 06470
Community: Liberty at Newtown
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.



Connecticut 55+ Housing Market Trends

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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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