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Connecticut 55+ active adult communities & homes for sale - Page 2

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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The Cottages at Wire Mill
$1Ms
The Cottages at Wire Mill, Stamford, CT
New Construction | 55+ age-restricted | Built 2026 - present | 9 homes
The Seasons at East North...
$700ks
The Seasons at East North..., East Northport, NY
New Construction | 55+ age-restricted | Built 2023 - present | 190 homes
Regency at Prospect
$300ks - $400ks
Regency at Prospect, Prospect, CT
Resale Only | 55+ age-restricted | Built 2006 - 2020 | 379 homes
5 rating (2 reviews) Benson Woods
$400ks - $600ks
Benson Woods, Middlebury, CT
New and Resale | 55+ age-restricted | Built 2004 - present | 79 homes
The Summit at Bethel
$500ks - $700ks
The Summit at Bethel, Bethel, CT
Resale Only | 55+ age-restricted | Built 2010 - 2021 | 235 homes
Want to learn more about 55+ communities in Connecticut? 55places can help!
Questions? Call us: (888) 625-4885
The Village at Buckingham
$300ks - $400ks
The Village at Buckingham, Avon, CT
Resale Only | 55+ age-restricted | Built 2002 - 2006 | 56 homes
The Powder Forest Homes
$500ks - $700ks
The Powder Forest Homes, Simsbury, CT
Resale Only | 55+ age-restricted | Built 2006 - 2016 | 182 homes
5 rating (3 reviews) Founders Ridge
$300ks - $400ks
Founders Ridge, Middletown, CT
New Construction | 55+ age-restricted | Built 2017 - present | 75 homes
Billingsgate
$400ks - $600ks
Billingsgate, Simsbury, CT
Resale Only | 55+ age-restricted | Built 2003 - 2006 | 37 homes
Long Hill Village
$300ks - $400ks
Long Hill Village, Trumbull, CT
Resale Only | 55+ age-restricted | Built 1997 - 1999 | 71 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.
Regency Meadows
$500ks
Regency Meadows, Trumbull, CT
Resale Only | 55+ age-restricted | Built 2003 - 2005 | 51 homes
Bidwell Village
$300ks - $400ks
Bidwell Village, Coventry, CT
New Construction | 55+ age-restricted | Built 2020 - present | 37 homes
Whitney Glen
$500ks - $600ks
Whitney Glen, Westport, CT
Resale Only | 55+ age-restricted | Built 1982 - 1982 | 62 homes
5 rating (1 review) The Villages at Mount Sin...
$600ks
The Villages at Mount Sin..., Mount Sinai, NY
Resale Only | 55+ age-restricted | Built 2005 - 2007 | 185 homes
Village Vistas
$800ks - $1Ms
Village Vistas, Port Jefferson, NY
Resale Only | 55+ age-restricted | Built 2013 - 2017 | 43 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
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
Vineyards at Brookfield
$400ks - $500ks
Vineyards at Brookfield, Center Moriches, NY
New Construction | 55+ age-restricted | Built 2019 - present | 146 homes
Country Pointe Preserve
$600ks - $900ks
Country Pointe Preserve, Yaphank, NY
New Construction | 55+ age-restricted | Built 2024 - present | 152 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.
Shaker Heights
$400ks - $500ks
Shaker Heights, Enfield, CT
New Construction | 55+ age-restricted | Built 2018 - present | 77 homes
Bramble Ridge
$300ks
Bramble Ridge, Suffield, CT
Resale Only | 55+ age-restricted | Built 2005 - 2015 | 47 homes
Autumn Fields
$200ks - $300ks
Autumn Fields, Enfield, CT
Resale Only | 55+ age-restricted | Built 2004 - 2006 | 56 homes
The Gardens of Wilbraham
$200ks - $400ks
The Gardens of Wilbraham, Wilbraham, MA
New and Resale | 55+ age-restricted | Built 2005 - present | 108 homes
Vineyards at Moriches
$500ks - $600ks
Vineyards at Moriches, Center Moriches, NY
Resale Only | 55+ age-restricted | Built 2008 - 2014 | 92 homes
The Woods at Dunham Pond
$200ks - $400ks
The Woods at Dunham Pond, New Fairfield, CT
Resale Only | 55+ age-restricted | Built 2004 - 2015 | 33 homes
Summer Wind Estates
$300ks - $400ks
Summer Wind Estates, North Haven, CT
New Construction | 55+ age-restricted | Built 2015 - present | 18 homes
Want to learn more about 55+ communities in Connecticut? 55places can help!
Questions? Call us: (888) 625-4885
RiverBend Estates
$400ks
RiverBend Estates, Oxford, CT
New and Resale | 55+ age-restricted | Built 2012 - present | 25 homes
Park Glen
$300ks - $500ks
Park Glen, New Milford, CT
Resale Only | 55+ age-restricted | Built 2006 - 2015 | 17 homes
Oak Meadow Estates
$200ks - $300ks
Oak Meadow Estates, Torrington, CT
New and Resale | 55+ age-restricted | Built 2013 - present | 31 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.
Hopmeadow Place
$200ks - $300ks
Hopmeadow Place, Simsbury, CT
Resale Only | 55+ age-restricted | Built 2005 - 2005 | 66 homes
Gloria Commons
$200ks - $300ks
Gloria Commons, Milford, CT
Resale Only | 55+ age-restricted | Built 2007 - 2015 | 50 homes
Boulder Brook
$200ks
Boulder Brook, Prospect, CT
Resale Only | 55+ age-restricted | Built 2004 - 2006 | 35 homes
The Atrium of Portland
<$100k
The Atrium of Portland, Portland, CT
Resale Only | 55+ age-restricted | Built 2004 - 2004 | 56 homes
Eastport Meadows
$400ks
Eastport Meadows, Eastport, NY
Resale Only | 55+ age-restricted | Built 2009 - 2016 | 50 homes
Autumn Estates
$500ks - $600ks
Autumn Estates, Farmington, CT
Resale Only | 55+ age-restricted | Built 2011 - 2017 | 30 homes
Bartlett Hollow
$200ks - $400ks
Bartlett Hollow, Middletown, CT
New Construction | 55+ age-restricted | Built 2015 - present | 25 homes
77 Sunset Lane
$400ks - $700ks
77 Sunset Lane, Ridgefield, CT
Resale Only | 55+ age-restricted | Built 2016 - 2018 | 54 homes
Want to learn more about 55+ communities in Connecticut? 55places can help!
Questions? Call us: (888) 625-4885
The Seasons at Plainview
$500ks - $600ks
The Seasons at Plainview, Plainview, NY
Resale Only | 55+ age-restricted | Built 2006 - 2007 | 134 homes
Baldwin Station
$400ks
Baldwin Station, Milford, CT
Resale Only | 55+ age-restricted | Built 2001 - 2003 | 82 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.
New 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 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
Want to learn more about 55+ communities in Connecticut? 55places can help!
Questions? Call us: (888) 625-4885
New 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
New 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
New 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
New 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
New 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
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 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
New 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
New 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
New 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
New 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
New 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
Want to learn more about 55+ communities in Connecticut? 55places can help!
Questions? Call us: (888) 625-4885
New 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
New 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
New 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
New 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
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 The Powder Forest Homes 4 ASHTON CIR 4, SIMSBURY, CT, 06070, Simsbury, CT 06070
$729,000

2 beds

|

4 baths

|

2,381 sq ft

4 ASHTON CIR 4, SIMSBURY, CT, 06070
New 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
New 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
New 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
New 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
New Foxwood Village 1407 MIDDLE RD 233, RIVERHEAD, NY, 11933, Riverhead, NY 11933
$405,000

3 beds

|

2 baths

|

1,792 sq ft

|

Manufactured Home

1407 MIDDLE RD 233, RIVERHEAD, NY, 11933
Community: Foxwood Village
New Greenwood Village 402 VILLAGE CIR, BROOKHAVEN, NY, 11949, Brookhaven, NY 11949
$250,000

2 beds

|

2 baths

|

1,122 sq ft

|

Condo

402 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
New Leisure Village 449 ARLINGTON DR, BROOKHAVEN, NY, 11961, Brookhaven, NY 11961
$310,000

2 beds

|

1 baths

|

1,074 sq ft

|

Condo

449 ARLINGTON DR, BROOKHAVEN, NY, 11961
Community: Leisure Village
New The Greens at Half Hollow 849 MADEIRA BLVD, HUNTINGTON, NY, 11747, Huntington, NY 11747
$738,888

2 beds

|

2 baths

|

1,150 sq ft

|

Condo

849 MADEIRA BLVD, HUNTINGTON, NY, 11747
New Heritage Village 399 HERITAGE VLG B, SOUTHBURY, CT, 06488, Southbury, CT 06488
$275,000

2 beds

|

2 baths

|

1,076 sq ft

|

Condo

399 HERITAGE VLG B, 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.
Woodridge Strathmore Terrace 41 CHIPPENDALE DR, BROOKHAVEN, NY, 11766, Brookhaven, NY 11766
$599,000

2 beds

|

2 baths

|

1,501 sq ft

|

Condo

41 CHIPPENDALE DR, BROOKHAVEN, NY, 11766
The Vineyards at Miller Place 48 AVERY LN, BROOKHAVEN, NY, 11764, Brookhaven, NY 11764
$619,996

2 beds

|

3 baths

|

1,486 sq ft

|

Condo

48 AVERY LN, BROOKHAVEN, NY, 11764
Leisure Glen 562 LEISURE DR, BROOKHAVEN, NY, 11961, Brookhaven, NY 11961
$670,000

2 beds

|

2 baths

|

1,652 sq ft

|

House

562 LEISURE DR, BROOKHAVEN, NY, 11961
Community: Leisure Glen
Leisure Glen 3 BALDWIN CT, BROOKHAVEN, NY, 11961, Brookhaven, NY 11961
$499,900

2 beds

|

2 baths

|

1,542 sq ft

|

Condo

3 BALDWIN CT, BROOKHAVEN, NY, 11961
Community: Leisure Glen
Greenwood Village 24 GREENWOOD BLVD, BROOKHAVEN, NY, 11949, Brookhaven, NY 11949
$79,999

1 beds

|

1 baths

|

812 sq ft

|

Condo

24 GREENWOOD BLVD, BROOKHAVEN, NY, 11949
Community: Greenwood Village
Leisure Village 470B DARWEN DR, BROOKHAVEN, NY, 11961, Brookhaven, NY 11961
$339,000

2 beds

|

1 baths

|

1,074 sq ft

|

Condo

470B DARWEN DR, BROOKHAVEN, NY, 11961
Community: Leisure Village
Meadow Brook Estates 107 MEADOW BROOK RD 107, OXFORD, CT, 064..., Oxford, CT 06478
$569,900

3 beds

|

3 baths

|

1,922 sq ft

|

Condo

107 MEADOW BROOK RD 107, OXFORD, CT, 064...
The Vineyards at Miller Place 40 AVERY LN, BROOKHAVEN, NY, 11764, Brookhaven, NY 11764
$625,000

3 beds

|

3 baths

|

1,700 sq ft

|

Condo

40 AVERY LN, BROOKHAVEN, NY, 11764
Want to learn more about 55+ communities in Connecticut? 55places can help!
Questions? Call us: (888) 625-4885
Leisure Glen 488 LEISURE DR, BROOKHAVEN, NY, 11961, Brookhaven, NY 11961
$659,000

2 beds

|

2 baths

|

1,652 sq ft

|

Condo

488 LEISURE DR, BROOKHAVEN, NY, 11961
Community: Leisure Glen
Stoneleigh Woods at Riverhead 904 BALTUSROL BLVD, RIVERHEAD, NY, 11901, Riverhead, NY 11901
$510,000

2 beds

|

2 baths

|

1,258 sq ft

|

Condo

904 BALTUSROL BLVD, RIVERHEAD, NY, 11901
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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This application does not include information on all of the properties available for sale at this time.

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