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Connecticut 55+ active adult communities & homes for sale - Page 5

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
Leisure Knoll 152A LAURANCE LN A, BROOKHAVEN, NY, 1196..., Brookhaven, NY 11961
$349,000

2 beds

|

1 baths

|

755 sq ft

|

Condo

152A LAURANCE LN A, BROOKHAVEN, NY, 1196...
Community: Leisure Knoll
Leisure Glen 6 OAKDALE CT, BROOKHAVEN, NY, 11961, Brookhaven, NY 11961
$539,000

2 beds

|

2 baths

|

1,666 sq ft

|

Condo

6 OAKDALE CT, BROOKHAVEN, NY, 11961
Community: Leisure Glen
Leisure Glen 428 LEISURE DR, BROOKHAVEN, NY, 11961, Brookhaven, NY 11961
$649,000

2 beds

|

2 baths

|

1,652 sq ft

|

Condo

428 LEISURE DR, BROOKHAVEN, NY, 11961
Community: Leisure Glen
Leisure Village 134 EASTBOURNE CT A, BROOKHAVEN, NY, 119..., Brookhaven, NY 11961
$335,000

2 beds

|

1 baths

|

836 sq ft

|

Condo

134 EASTBOURNE CT A, BROOKHAVEN, NY, 119...
Community: Leisure Village
Heritage Village 559 HERITAGE VLG B, SOUTHBURY, CT, 06488, Southbury, CT 06488
$299,900

2 beds

|

2 baths

|

1,432 sq ft

|

Condo

559 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
Rivington 714 CENTER MEADOW LN 714, DANBURY, CT, 0..., Danbury, CT 06810
$474,900

2 beds

|

2 baths

|

1,258 sq ft

|

Condo

714 CENTER MEADOW LN 714, DANBURY, CT, 0...
Community: Rivington
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
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...
Oronoque Village 546 N TRL A, STRATFORD, CT, 06614, Stratford, CT 06614
$445,000

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
$650,000

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.
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
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
Heritage Village 261B HERITAGE VLG, SOUTHBURY, CT, 06488, Southbury, CT 06488
$254,000

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
Spring Lake Village 504 CARRIAGE DR 504, SOUTHINGTON, CT, 06..., Southington, CT 06489
$320,000

2 beds

|

2 baths

|

1,313 sq ft

|

Condo

504 CARRIAGE DR 504, SOUTHINGTON, CT, 06...
Community: Spring Lake Village
Encore Atlantic Shores 140 CHOPIN PL, BROOKHAVEN, NY, 11941, Brookhaven, NY 11941
$849,900

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
The Village at Oxford Greens 171 COUNTRY CLUB DR 171, OXFORD, CT, 064..., Oxford, CT 06478
$705,000

3 beds

|

3 baths

|

2,750 sq ft

|

Condo

171 COUNTRY CLUB DR 171, OXFORD, CT, 064...
Westhampton Pines 79 SAMANTHA CIR, SOUTHAMPTON, NY, 11977, Southampton, NY 11977
$1,295,000

2 beds

|

3 baths

|

2,440 sq ft

|

Condo

79 SAMANTHA CIR, SOUTHAMPTON, NY, 11977
Community: Westhampton Pines
Hopmeadow Place 1 W ST 215, SIMSBURY, CT, 06070, Simsbury, CT 06070
$385,000

2 beds

|

2 baths

|

1,477 sq ft

|

Condo

1 W ST 215, SIMSBURY, CT, 06070
Community: Hopmeadow Place
Greenwood Village 28 GREENWOOD BLVD, BROOKHAVEN, NY, 11949, Brookhaven, NY 11949
$139,999

2 beds

|

2 baths

|

938 sq ft

|

Condo

28 GREENWOOD BLVD, BROOKHAVEN, NY, 11949
Community: Greenwood 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.
Rivington 215 CENTER MEADOW LN 215, DANBURY, CT, 0..., Danbury, CT 06810
$475,000

2 beds

|

2 baths

|

1,258 sq ft

|

Condo

215 CENTER MEADOW LN 215, DANBURY, CT, 0...
Community: Rivington
The Waterways at Moriches 416 LINDSAY LN, BROOKHAVEN, NY, 11955, Brookhaven, NY 11955
$575,000

2 beds

|

2 baths

|

1,440 sq ft

|

Condo

416 LINDSAY LN, BROOKHAVEN, NY, 11955
Regency at Woodbridge 27 HERITAGE LN, WOODBRIDGE, CT, 06525, Woodbridge, CT 06525
$599,900

3 beds

|

3 baths

|

2,006 sq ft

|

Condo

27 HERITAGE LN, WOODBRIDGE, CT, 06525
Fairfield at St. James 708 W CABOT CT 708, SMITHTOWN, NY, 11780, Smithtown, NY 11780
$498,998

1 beds

|

1 baths

|

886 sq ft

|

Condo

708 W CABOT CT 708, SMITHTOWN, NY, 11780
Glenwood Village 1661 OLD COUNTRY RD 377, RIVERHEAD, NY, ..., Riverhead, NY 11901
$369,000

3 beds

|

2 baths

|

1,317 sq ft

|

Manufactured Home

1661 OLD COUNTRY RD 377, RIVERHEAD, NY, ...
Community: Glenwood Village
Heritage Village 345 HERITAGE VLG A, SOUTHBURY, CT, 06488, Southbury, CT 06488
$350,000

3 beds

|

2 baths

|

1,716 sq ft

|

Condo

345 HERITAGE VLG A, SOUTHBURY, CT, 06488
Community: Heritage Village
Harmony Place 21 FIDELITY DR 73, RUTLAND, MA, 01543, Rutland, MA 01543
$489,000

2 beds

|

2 baths

|

1,582 sq ft

|

Condo

21 FIDELITY DR 73, RUTLAND, MA, 01543
Community: Harmony Place
Want to learn more about 55+ communities in Connecticut? 55places can help!
Questions? Call us: (888) 625-4885
Harmony Place 23 FIDELITY DR 74, RUTLAND, MA, 01543, Rutland, MA 01543
$489,000

2 beds

|

2 baths

|

1,582 sq ft

|

Condo

23 FIDELITY DR 74, RUTLAND, MA, 01543
Community: Harmony Place
Harmony Place 19 FIDELITY DR 72, RUTLAND, MA, 01543, Rutland, MA 01543
$498,000

2 beds

|

2 baths

|

1,582 sq ft

|

Condo

19 FIDELITY DR 72, RUTLAND, MA, 01543
Community: Harmony Place
Harmony Place 17 FIDELITY DR 71, RUTLAND, MA, 01543, Rutland, MA 01543
$498,000

2 beds

|

2 baths

|

1,582 sq ft

|

Condo

17 FIDELITY DR 71, RUTLAND, MA, 01543
Community: Harmony Place
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.
Vineyards at Brookfield 61 AVERY DR, BROOKHAVEN, NY, 11934, Brookhaven, NY 11934
$674,999

2 beds

|

2 baths

|

1,557 sq ft

|

Condo

61 AVERY DR, BROOKHAVEN, NY, 11934
Greenwood Village 69 DOGWOOD LN, BROOKHAVEN, NY, 11949, Brookhaven, NY 11949
$139,000

2 beds

|

2 baths

|

1,134 sq ft

|

Condo

69 DOGWOOD LN, BROOKHAVEN, NY, 11949
Community: Greenwood Village
Encore Atlantic Shores 228 SONATA CT, BROOKHAVEN, NY, 11941, Brookhaven, NY 11941
$749,000

2 beds

|

2 baths

|

1,605 sq ft

|

Condo

228 SONATA CT, BROOKHAVEN, NY, 11941
Fairview at Oxford Greens 1129 ST ANDREWS DR 49, OXFORD, CT, 06478, Oxford, CT 06478
$709,555

2 beds

|

3 baths

|

2,454 sq ft

|

Condo

1129 ST ANDREWS DR 49, OXFORD, CT, 06478
The Village at Oxford Greens 1129 ST ANDREWS DR 49, OXFORD, CT, 06478, Oxford, CT 06478
$709,555

2 beds

|

3 baths

|

2,454 sq ft

|

Condo

1129 ST ANDREWS DR 49, OXFORD, CT, 06478
Fairview at Oxford Greens 1111 ST ANDREWS DR 16, OXFORD, CT, 06478, Oxford, CT 06478
$749,900

2 beds

|

3 baths

|

2,454 sq ft

|

Condo

1111 ST ANDREWS DR 16, OXFORD, CT, 06478
The Village at Oxford Greens 1111 ST ANDREWS DR 16, OXFORD, CT, 06478, Oxford, CT 06478
$749,900

2 beds

|

3 baths

|

2,454 sq ft

|

Condo

1111 ST ANDREWS DR 16, OXFORD, CT, 06478
The Village at Oxford Greens 1138 ST ANDREWS DR 90, OXFORD, CT, 06478, Oxford, CT 06478
$799,655

2 beds

|

3 baths

|

1,955 sq ft

|

Condo

1138 ST ANDREWS DR 90, OXFORD, CT, 06478
Want to learn more about 55+ communities in Connecticut? 55places can help!
Questions? Call us: (888) 625-4885
Fairview at Oxford Greens 1138 ST ANDREWS DR 90, OXFORD, CT, 06478, Oxford, CT 06478
$799,655

2 beds

|

3 baths

|

1,955 sq ft

|

Condo

1138 ST ANDREWS DR 90, OXFORD, CT, 06478
Encore Atlantic Shores 63 ENCORE BLVD, BROOKHAVEN, NY, 11941, Brookhaven, NY 11941
$890,000

2 beds

|

3 baths

|

2,769 sq ft

|

Condo

63 ENCORE BLVD, BROOKHAVEN, NY, 11941
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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