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Connecticut 55+ active adult communities & homes for sale - Page 3

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


239 homes 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
Harmony Place
$400ks - $500ks
Harmony Place, Rutland, MA
New Construction | 55+ age-restricted | Built 2023 - present | 142 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
Want to learn more about 55+ communities in Connecticut? 55places can help!
Questions? Call us: (888) 625-4885
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) Westhampton Pines
$900ks - $1Ms
Westhampton Pines, Westhampton, NY
Resale Only | 55+ age-restricted | Built 2005 - 2013 | 189 homes
4 rating (8 reviews) Glenwood Village
$100ks - $200ks
Glenwood Village, Riverhead, NY
New and Resale | 55+ age-restricted | Built 1959 - present | 588 homes
5 rating (1 review) Newtown Woods
$300ks - $500ks
Newtown Woods, Newtown, CT
New and Resale | 55+ age-restricted | Built 2011 - present | 178 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) Sunken Pond Estates
$400ks
Sunken Pond Estates, Riverhead, NY
Resale Only | 55+ age-restricted | Built 2003 - 2005 | 194 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
3.5 rating (2 reviews) Foxwood Village
$200ks - $400ks
Foxwood Village, Calverton, NY
Resale Only | 55+ age-restricted | Built 1986 - 2007 | 294 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
Saddle Lakes
$400ks - $500ks
Saddle Lakes, Riverhead, NY
Resale Only | 55+ age-restricted | Built 2000 - 2002 | 196 homes
The Vineyards at Miller P...
$500ks
The Vineyards at Miller P..., Miller Place, NY
Resale Only | 55+ age-restricted | Built 2004 - 2005 | 85 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
Windcrest East
$400ks - $500ks
Windcrest East, Calverton, NY
Resale Only | 55+ age-restricted | Built 2004 - 2005 | 126 homes
Kensington Estates
$1Ms
Kensington Estates, Woodbury, NY
New Construction | 55+ age-restricted | Built 2019 - 2021 | 80 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.
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
Liberty at Newtown
$300ks - $400ks
Liberty at Newtown, Newtown, CT
Resale Only | 55+ age-restricted | Built 2003 - 2007 | 96 homes
Sonoma Woods
$300ks
Sonoma Woods, Middletown, CT
Resale Only | 55+ age-restricted | Built 2005 - 2015 | 68 homes
Country Pointe Plainview
$700ks - $1Ms
Country Pointe Plainview, Plainview, NY
New Construction | 55+ age-restricted | Built 2017 - present | 660 homes
Regency at Woodbridge
$500ks - $700ks
Regency at Woodbridge, Woodbridge, CT
New Construction | 55+ age-restricted | Built 2023 - present | 70 homes
Eagles Walk at East Quogu...
$300ks - $400ks
Eagles Walk at East Quogu..., East Quogue, NY
Resale Only | 55+ age-restricted | Built 2004 - 2014 | 67 homes
The Seasons at Elwood
$800ks - $900ks
The Seasons at Elwood, East Northport, NY
Resale Only | 55+ age-restricted | Built 2018 - 2020 | 256 homes
Strathmore Gate East
$300ks
Strathmore Gate East, Coram, NY
Resale Only | 55+ age-restricted | Built 1970 - 1975 | 174 homes
Want to learn more about 55+ communities in Connecticut? 55places can help!
Questions? Call us: (888) 625-4885
12...3
Spring Lake Village 19 HICKORY HL 19, SOUTHINGTON, CT, 06489, Southington, CT 06489
$239,000

2 beds

|

2 baths

|

1,285 sq ft

|

Condo

19 HICKORY HL 19, SOUTHINGTON, CT, 06489
Community: Spring Lake Village
Heritage Village 682 HERITAGE VLG A, SOUTHBURY, CT, 06488, Southbury, CT 06488
$330,000

3 beds

|

2 baths

|

1,716 sq ft

|

Condo

682 HERITAGE VLG A, SOUTHBURY, CT, 06488
Community: Heritage Village
Greenwood Village 5 HOLLY DR, BROOKHAVEN, NY, 11949, Brookhaven, NY 11949
$99,990

2 beds

|

2 baths

|

960 sq ft

|

Condo

5 HOLLY DR, BROOKHAVEN, NY, 11949
Community: Greenwood Village
Heritage Village 139 HERITAGE VLG B, SOUTHBURY, CT, 06488, Southbury, CT 06488
$415,000

2 beds

|

2 baths

|

1,432 sq ft

|

Condo

139 HERITAGE VLG B, SOUTHBURY, CT, 06488
Community: Heritage Village
Heritage Village 883 HERITAGE VLG C, SOUTHBURY, CT, 06488, Southbury, CT 06488
$319,900

2 beds

|

2 baths

|

1,000 sq ft

|

Condo

883 HERITAGE VLG C, SOUTHBURY, CT, 06488
Community: Heritage Village
Want to learn more about 55+ communities in Connecticut? 55places can help!
Questions? Call us: (888) 625-4885
Pond Spring Village 111 PONDVIEW CIR 111, BEACON FALLS, CT, ..., Beacon Falls, CT 06403
$435,000

2 beds

|

2 baths

|

1,328 sq ft

|

Condo

111 PONDVIEW CIR 111, BEACON FALLS, CT, ...
Community: Pond Spring Village
Meadow Brook Estates 132 MEADOW BROOK RD 132, OXFORD, CT, 064..., Oxford, CT 06478
$579,900

2 beds

|

3 baths

|

1,931 sq ft

|

Condo

132 MEADOW BROOK RD 132, OXFORD, CT, 064...
Heritage Village 953 HERITAGE VLG A, SOUTHBURY, CT, 06488, Southbury, CT 06488
$245,000

1 beds

|

1 baths

|

928 sq ft

|

Condo

953 HERITAGE VLG A, SOUTHBURY, CT, 06488
Community: Heritage Village
Oronoque Village 13 ALGONQUIN LN B, STRATFORD, CT, 06614, Stratford, CT 06614
$375,000

1 beds

|

2 baths

|

1,480 sq ft

|

Condo

13 ALGONQUIN LN B, STRATFORD, CT, 06614
Community: Oronoque Village
Newtown Woods 632 BROOKSIDE CT 632, NEWTOWN, CT, 06470, Newtown, CT 06470
$589,000

2 beds

|

2 baths

|

1,807 sq ft

|

Condo

632 BROOKSIDE CT 632, NEWTOWN, CT, 06470
Community: Newtown Woods
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 120 SCENIC LAKE DR, RIVERHEAD, NY, 11901, Riverhead, NY 11901
$549,000

2 beds

|

2 baths

|

1,386 sq ft

|

Condo

120 SCENIC LAKE DR, RIVERHEAD, NY, 11901
Community: Saddle Lakes
The Greens at Half Hollow 991 MADEIRA BLVD, HUNTINGTON, NY, 11747, Huntington, NY 11747
$789,000

2 beds

|

2 baths

|

1,058 sq ft

|

Condo

991 MADEIRA BLVD, HUNTINGTON, NY, 11747
Westhampton Pines 30 KIMBERLY DR, SOUTHAMPTON, NY, 11977, Southampton, NY 11977
$1,395,000

2 beds

|

3 baths

|

2,400 sq ft

|

Condo

30 KIMBERLY DR, SOUTHAMPTON, NY, 11977
Community: Westhampton Pines
Heritage Village 991 HERITAGE VLG A, SOUTHBURY, CT, 06488, Southbury, CT 06488
$255,000

2 beds

|

2 baths

|

1,432 sq ft

|

Condo

991 HERITAGE VLG A, SOUTHBURY, CT, 06488
Community: Heritage Village
Meadow Brook Estates 207 WOODLAWN DR 207, SEYMOUR, CT, 06483, Seymour, CT 06483
$625,000

3 beds

|

3 baths

|

2,484 sq ft

|

Condo

207 WOODLAWN DR 207, SEYMOUR, CT, 06483
Spring Lake Village 1 HICKORY HL 1, SOUTHINGTON, CT, 06489, Southington, CT 06489
$239,000

2 beds

|

2 baths

|

1,285 sq ft

|

Condo

1 HICKORY HL 1, SOUTHINGTON, CT, 06489
Community: Spring Lake Village
Want to learn more about 55+ communities in Connecticut? 55places can help!
Questions? Call us: (888) 625-4885
Heritage Village 226A S DURKEE HILL RD 226A, SOUTHBURY, C..., Southbury, CT 06488
$309,500

2 beds

|

2 baths

|

1,398 sq ft

|

Condo

226A S DURKEE HILL RD 226A, SOUTHBURY, C...
Community: Heritage Village
The Seasons at East Northport 40 AUGUST CIR 40, HUNTINGTON, NY, 11731, Huntington, NY 11731
$772,150

2 beds

|

2 baths

|

1,536 sq ft

|

Condo

40 AUGUST CIR 40, HUNTINGTON, NY, 11731
Leisure Knoll 257 EDINBURGH DR, BROOKHAVEN, NY, 11961, Brookhaven, NY 11961
$539,900

2 beds

|

2 baths

|

1,000 sq ft

|

Condo

257 EDINBURGH DR, BROOKHAVEN, NY, 11961
Community: Leisure Knoll
Beckley Farms 91 SCENIC DR 91, BERLIN, CT, 06037, Berlin, CT 06037
$679,900

3 beds

|

3 baths

|

2,068 sq ft

|

Condo

91 SCENIC DR 91, BERLIN, CT, 06037
Community: Beckley 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.
Foxwood Village 1407 MIDDLE RD 45, RIVERHEAD, NY, 11933, Riverhead, NY 11933
$315,000

2 beds

|

2 baths

|

1,100 sq ft

|

House

1407 MIDDLE RD 45, RIVERHEAD, NY, 11933
Community: Foxwood Village
Heritage Village 397 KRUEGER CIR A, SOUTHBURY, CT, 06488, Southbury, CT 06488
$439,700

3 beds

|

2 baths

|

1,716 sq ft

|

Condo

397 KRUEGER CIR A, SOUTHBURY, CT, 06488
Community: Heritage Village
The Village at Oxford Greens 1073 AUGUSTA DR 1073, OXFORD, CT, 06478, Oxford, CT 06478
$629,900

2 beds

|

3 baths

|

2,232 sq ft

|

Condo

1073 AUGUSTA DR 1073, OXFORD, CT, 06478
Fairview at Oxford Greens 1073 AUGUSTA DR 1073, OXFORD, CT, 06478, Oxford, CT 06478
$629,900

2 beds

|

3 baths

|

2,232 sq ft

|

Condo

1073 AUGUSTA DR 1073, OXFORD, CT, 06478
Oronoque Village 55 BLACKHAWK LN B, STRATFORD, CT, 06614, Stratford, CT 06614
$639,000

2 beds

|

3 baths

|

1,360 sq ft

|

Condo

55 BLACKHAWK LN B, STRATFORD, CT, 06614
Community: Oronoque Village
Meadowbrook Pointe Links & Spa 38 AUGUSTA DR, BROOKHAVEN, NY, 11763, Brookhaven, NY 11763
$400,624

2 beds

|

3 baths

|

1,440 sq ft

|

Condo

38 AUGUSTA DR, BROOKHAVEN, NY, 11763
Oronoque Village 209 ACORN LN B, STRATFORD, CT, 06614, Stratford, CT 06614
$519,000

2 beds

|

3 baths

|

1,438 sq ft

|

Condo

209 ACORN LN B, STRATFORD, CT, 06614
Community: Oronoque Village
Want to learn more about 55+ communities in Connecticut? 55places can help!
Questions? Call us: (888) 625-4885
Heritage Village 633 HERITAGE VLG A, SOUTHBURY, CT, 06488, Southbury, CT 06488
$400,000

2 beds

|

2 baths

|

1,432 sq ft

|

Condo

633 HERITAGE VLG A, SOUTHBURY, CT, 06488
Community: Heritage Village
Heritage Village 626 HERITAGE VLG B, SOUTHBURY, CT, 06488, Southbury, CT 06488
$289,000

2 beds

|

2 baths

|

1,432 sq ft

|

Condo

626 HERITAGE VLG B, SOUTHBURY, CT, 06488
Community: Heritage Village
Fairfield at St. James 705 ALDEN CT, SMITHTOWN, NY, 11780, Smithtown, NY 11780
$559,803

2 beds

|

2 baths

|

954 sq ft

|

Condo

705 ALDEN CT, SMITHTOWN, NY, 11780
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
$595,000

2 beds

|

4 baths

|

1,572 sq ft

|

Condo

11 MERCY ST 11, DANBURY, CT, 06810
Community: Rivington
Heritage Village 149 HERITAGE VLG A, SOUTHBURY, CT, 06488, Southbury, CT 06488
$198,000

1 beds

|

1 baths

|

928 sq ft

|

Condo

149 HERITAGE VLG A, SOUTHBURY, CT, 06488
Community: Heritage Village
Bidwell Village 94 STONEHOUSE RD 13, COVENTRY, CT, 06238, Coventry, CT 06238
$365,000

3 beds

|

4 baths

|

1,810 sq ft

|

Condo

94 STONEHOUSE RD 13, COVENTRY, CT, 06238
Community: Bidwell Village
Sunken Pond Estates 3704 AMEN COR, RIVERHEAD, NY, 11901, Riverhead, NY 11901
$529,000

2 beds

|

3 baths

|

1,350 sq ft

|

Condo

3704 AMEN COR, RIVERHEAD, NY, 11901
Community: Sunken Pond Estates
Plymouth Estates at Mount Sinai 240 IRA RD, BROOKHAVEN, NY, 11766, Brookhaven, NY 11766
$589,999

2 beds

|

2 baths

|

1,396 sq ft

|

Condo

240 IRA RD, BROOKHAVEN, NY, 11766
Leisure Knoll 473 STRATFORD LN, BROOKHAVEN, NY, 11961, Brookhaven, NY 11961
$539,000

2 beds

|

2 baths

|

1,350 sq ft

|

House

473 STRATFORD LN, BROOKHAVEN, NY, 11961
Community: Leisure Knoll
Heritage Village 13 HERITAGE VLG B, SOUTHBURY, CT, 06488, Southbury, CT 06488
$223,000

2 beds

|

2 baths

|

1,032 sq ft

|

Condo

13 HERITAGE VLG B, SOUTHBURY, CT, 06488
Community: Heritage Village
Sonoma Woods 35 SONOMA LN 35, MIDDLETOWN, CT, 06457, Middletown, CT 06457
$589,000

2 beds

|

3 baths

|

1,798 sq ft

|

Condo

35 SONOMA LN 35, MIDDLETOWN, CT, 06457
Community: Sonoma Woods
Want to learn more about 55+ communities in Connecticut? 55places can help!
Questions? Call us: (888) 625-4885
Heritage Village 955 HERITAGE VLG B, SOUTHBURY, CT, 06488, Southbury, CT 06488
$269,900

2 beds

|

2 baths

|

1,398 sq ft

|

Condo

955 HERITAGE VLG B, SOUTHBURY, CT, 06488
Community: Heritage Village
The Village at Oxford Greens 155 COUNTRY CLUB DR 155, OXFORD, CT, 064..., Oxford, CT 06478
$649,000

3 beds

|

3 baths

|

2,008 sq ft

|

Condo

155 COUNTRY CLUB DR 155, OXFORD, CT, 064...
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.
REIN updates its listings on a daily basis. Data last updated: Nov 02, 2026.
This application does not include information on all of the properties available for sale at this time.

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