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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 unparalleled regional access — New York City and Boston are each under two hours away, the scenic Long…
Connecticut offers a classic New England retirement lifestyle coupled with unparalleled regional access — New York City and Boston are each under two hours away, the scenic Long Island Sound shoreline runs the length of the state, and the Litchfield Hills provide a peaceful, rural alternative. The state boasts an exceptional healthcare network, anchored by Yale New Haven Health and Hartford HealthCare, alongside four distinct seasons featuring world-renowned autumn foliage.Connecticut is home to 62 active adult communities, with properties ranging from the mid-$100Ks to over $1M and averaging around $547K. Heritage Village in Southbury (2,580 homes) is the crown jewel of the state — ranking as one of the largest and most established 55+ communities in all of New England. Active adults seeking mid-sized options gravitate toward Oronoque Village in Stratford (929 homes) and Spring Lake Village in Southington (640 homes), while those prioritizing modern layouts favor new construction neighborhoods like Chatfield Farms in Beacon Falls and The Village at Oxford Greens in Oxford. 55places has thoroughly profiled every local development with verified pricing tiers, honest resident reviews, and direct local agent connections.

Quick Facts About Retiring in Connecticut


106 communities near Connecticut

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Hopmeadow Place
$200ks - $300ks
Hopmeadow Place, Simsbury, CT
Resale Only | 55+ age-restricted | Built 2005 - 2005 | 66 homes
Regency Meadows
$500ks
Regency Meadows, Trumbull, CT
Resale Only | 55+ age-restricted | Built 2003 - 2005 | 51 homes
Regency at Woodbridge
$500ks - $700ks
Regency at Woodbridge, Woodbridge, CT
New Construction | 55+ age-restricted | Built 2023 - present | 70 homes
The Cottages at Wire Mill
$1Ms
The Cottages at Wire Mill, Stamford, CT
New Construction | 55+ age-restricted | Built 2026 - present | 9 homes
1 rating (1 reviews) Plymouth Estates at Mount...
$400ks - $500ks
Plymouth Estates at Mount..., Mount Sinai, NY
Resale Only | 55+ age-restricted | Built 2006 - 2013 | 285 homes
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Saddle Lakes
$400ks - $500ks
Saddle Lakes, Riverhead, NY
Resale Only | 55+ age-restricted | Built 2000 - 2002 | 196 homes
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 (1 reviews) 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
Setauket Meadows
$500ks - $600ks
Setauket Meadows, Setauket, NY
Resale Only | 55+ age-restricted | Built 2005 - 2007 | 150 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.
Strathmore Gate East
$300ks
Strathmore Gate East, Coram, NY
Resale Only | 55+ age-restricted | Built 1970 - 1975 | 174 homes
Country Village Estates
$300ks
Country Village Estates, Coram, NY
Resale Only | 55+ age-restricted | Built 1993 - 2001 | 195 homes
Windcrest East
$400ks - $500ks
Windcrest East, Calverton, NY
Resale Only | 55+ age-restricted | Built 2004 - 2005 | 126 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
Stone Ridge Estates
$500ks - $600ks
Stone Ridge Estates, Dix Hills, NY
Resale Only | 55+ age-restricted | Built 2004 - 2013 | 76 homes
Kensington Estates
$1Ms
Kensington Estates, Woodbury, NY
New Construction | 55+ age-restricted | Built 2019 - 2021 | 80 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 Vineyards at Mount Si...
$800ks - $1Ms
The Vineyards at Mount Si..., Mount Sinai, NY
New Construction | 55+ age-restricted | Built 2020 - present | 91 homes
Oak Meadow Estates
$200ks - $300ks
Oak Meadow Estates, Torrington, CT
New and Resale | 55+ age-restricted | Built 2013 - present | 31 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.
Granite Woods
$600ks - $700ks
Granite Woods, Middlebury, CT
New Construction | 55+ age-restricted | Built 2020 - present | 24 homes
Clockmaker's Hill
$100ks
Clockmaker's Hill, Winsted, CT
Resale Only | 55+ age-restricted | Built 2005 - 2014 | 38 homes
The Bridges at Oxford Gre...
$600ks
The Bridges at Oxford Gre..., Oxford, CT
New Construction | 55+ age-restricted | Built 2025 - present | 99 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
Applegate Estates
$500ks - $400ks
Applegate Estates, Southington, CT
New and Resale | 55+ age-restricted | Built 2010 - 2025 | 94 homes
Gloria Commons
$200ks - $300ks
Gloria Commons, Milford, CT
Resale Only | 55+ age-restricted | Built 2007 - 2015 | 50 homes
Rivington Landing
$500ks
Rivington Landing, Danbury, CT
New Construction | Age-targeted | Built 2025 - 2026 | 25 homes
Want to learn more about 55+ communities in Connecticut? 55places can help!
Questions? Call us: (888) 625-4885
Jessup's Landing
$1Ms
Jessup's Landing, Quogue, NY
New and Resale | 55+ age-restricted | Built 2009 - 2016 | 31 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
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.
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
5 rating (3 reviews) Founders Ridge
$300ks - $400ks
Founders Ridge, Middletown, CT
New Construction | 55+ age-restricted | Built 2017 - present | 75 homes
Newington Ridge Preserve
$300ks - $400ks
Newington Ridge Preserve, Newington, CT
New Construction | 55+ age-restricted | Built 2014 - present | 16 homes
RiverWalk
$500ks - $600ks
RiverWalk, Branford, CT
New and Resale | 55+ age-restricted | Built 2007 - present | 60 homes
Chimney Hill
$500ks - $700ks
Chimney Hill, Farmington, CT
Resale Only | 55+ age-restricted | Built 2006 - 2013 | 44 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
Eastport Meadows
$400ks
Eastport Meadows, Eastport, NY
Resale Only | 55+ age-restricted | Built 2009 - 2016 | 50 homes
Founders Village
$400ks - $500ks
Founders Village, Southold, NY
Resale Only | 55+ age-restricted | Built 1981 - 1985 | 92 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.
Heritage Village 345 HERITAGE VLG A, SOUTHBURY, CT, 06488, Southbury, CT 06488
$386,000

3 beds

|

2 baths

|

1,716 sq ft

|

Condo

345 HERITAGE VLG A, SOUTHBURY, CT, 06488
Community: Heritage Village
Greenwood Village 105 W VILLAGE CIR 105, BROOKHAVEN, NY, 1..., Brookhaven, NY 11949
$245,000

2 beds

|

2 baths

|

1,130 sq ft

|

Condo

105 W VILLAGE CIR 105, BROOKHAVEN, NY, 1...
Community: Greenwood Village
Glenwood Village 1661 OLD COUNTRY RD 516, RIVERHEAD, NY, ..., Riverhead, NY 11901
$419,000

2 beds

|

2 baths

|

1,624 sq ft

|

Manufactured Home

1661 OLD COUNTRY RD 516, RIVERHEAD, NY, ...
Community: Glenwood Village
New 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
New Encore Atlantic Shores 101 MOZART CT, BROOKHAVEN, NY, 11941, Brookhaven, NY 11941
$779,000

2 beds

|

2 baths

|

2,044 sq ft

|

House

101 MOZART CT, BROOKHAVEN, NY, 11941
Want to learn more about 55+ communities in Connecticut? 55places can help!
Questions? Call us: (888) 625-4885
New Heritage Village 1041 HERITAGE VLG A, SOUTHBURY, CT, 0648..., Southbury, CT 06488
$244,000

2 beds

|

2 baths

|

1,000 sq ft

|

Condo

1041 HERITAGE VLG A, SOUTHBURY, CT, 0648...
Community: Heritage Village
New Rivington 12 OLD PASTURE DR 12, DANBURY, CT, 06810, Danbury, CT 06810
$839,000

3 beds

|

4 baths

|

1,794 sq ft

|

Condo

12 OLD PASTURE DR 12, DANBURY, CT, 06810
Community: Rivington
New Greenwood Village 205 VILLAGE CIR, BROOKHAVEN, NY, 11949, Brookhaven, NY 11949
$125,000

2 beds

|

2 baths

|

1,138 sq ft

|

House

205 VILLAGE CIR, BROOKHAVEN, NY, 11949
Community: Greenwood Village
New 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...
New Spring Lake Village 321 SONGBIRD LN 321, SOUTHINGTON, CT, 06..., Southington, CT 06489
$269,900

2 beds

|

1 baths

|

912 sq ft

|

Condo

321 SONGBIRD LN 321, 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 Setauket Meadows 2 EMILYS WAY, BROOKHAVEN, NY, 11733, Brookhaven, NY 11733
$799,500

2 beds

|

3 baths

|

1,842 sq ft

|

Condo

2 EMILYS WAY, BROOKHAVEN, NY, 11733
Community: Setauket Meadows
New Oronoque Village 546 N TRL A, STRATFORD, CT, 06614, Stratford, CT 06614
$539,000

2 beds

|

3 baths

|

1,434 sq ft

|

Condo

546 N TRL A, STRATFORD, CT, 06614
Community: Oronoque Village
New The Greens at Half Hollow 1118 SAVOY DR, HUNTINGTON, NY, 11747, Huntington, NY 11747
$695,000

2 beds

|

2 baths

|

1,100 sq ft

|

Condo

1118 SAVOY DR, HUNTINGTON, NY, 11747
New Rivington 11 MERCY ST 11, DANBURY, CT, 06810, Danbury, CT 06810
$630,000

2 beds

|

4 baths

|

1,572 sq ft

|

Condo

11 MERCY ST 11, DANBURY, CT, 06810
Community: Rivington
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
Leisure Glen 272 GLEN DR, BROOKHAVEN, NY, 11961, Brookhaven, NY 11961
$549,000

2 beds

|

2 baths

|

1,456 sq ft

|

Condo

272 GLEN DR, BROOKHAVEN, NY, 11961
Community: Leisure Glen
Want to learn more about 55+ communities in Connecticut? 55places can help!
Questions? Call us: (888) 625-4885
Woodridge Strathmore Terrace 62 HEARTHSIDE DR, BROOKHAVEN, NY, 11766, Brookhaven, NY 11766
$425,000

2 beds

|

2 baths

|

1,105 sq ft

|

Condo

62 HEARTHSIDE DR, BROOKHAVEN, NY, 11766
Meadow Brook Estates 107 MEADOW BROOK RD 107, OXFORD, CT, 064..., Oxford, CT 06478
$639,000

3 beds

|

3 baths

|

1,922 sq ft

107 MEADOW BROOK RD 107, OXFORD, CT, 064...
Shaker Heights 12 COPLEY CIR 12, ENFIELD, CT, 06082, Enfield, CT 06082
$589,900

2 beds

|

2 baths

|

1,897 sq ft

|

Condo

12 COPLEY CIR 12, ENFIELD, CT, 06082
Community: Shaker Heights
The Powder Forest Homes 9 GRISWOLD PL 9, SIMSBURY, CT, 06070, Simsbury, CT 06070
$1,250,000

3 beds

|

5 baths

|

2,774 sq ft

9 GRISWOLD PL 9, SIMSBURY, CT, 06070
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 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
$260,000

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
Heritage Village 1016 HERITAGE VLG A, SOUTHBURY, CT, 0648..., Southbury, CT 06488
$245,000

1 beds

|

1 baths

|

928 sq ft

|

Condo

1016 HERITAGE VLG A, SOUTHBURY, CT, 0648...
Community: Heritage Village
Spring Lake Village 504 CARRIAGE DR 504, SOUTHINGTON, CT, 06..., Southington, CT 06489
$330,000

2 beds

|

2 baths

|

1,313 sq ft

|

Condo

504 CARRIAGE DR 504, SOUTHINGTON, CT, 06...
Community: Spring Lake Village
Stoneleigh Woods at Riverhead 158 STONELEIGH DR, RIVERHEAD, NY, 11901, Riverhead, NY 11901
$699,000

2 beds

|

3 baths

|

2,071 sq ft

|

Condo

158 STONELEIGH DR, RIVERHEAD, NY, 11901
Country Pointe Preserve 128 JUNIPER LN 26, BROOKHAVEN, NY, 11980, Brookhaven, NY 11980
$875,000

2 beds

|

3 baths

|

1,998 sq ft

|

Condo

128 JUNIPER LN 26, BROOKHAVEN, NY, 11980
Want to learn more about 55+ communities in Connecticut? 55places can help!
Questions? Call us: (888) 625-4885
Rivington 424 CENTER MEADOW LN 424, DANBURY, CT, 0..., Danbury, CT 06810
$479,900

2 beds

|

2 baths

|

1,258 sq ft

|

Condo

424 CENTER MEADOW LN 424, DANBURY, CT, 0...
Community: Rivington
Country Pointe Plainview 52102 BEECH TREE LN, OYSTER BAY, NY, 118..., Oyster Bay, NY 11803
$1,669,990

2 beds

|

3 baths

|

1,750 sq ft

|

Condo

52102 BEECH TREE LN, OYSTER BAY, NY, 118...
Glenwood Village 1661 OLD COUNTRY RD 454, RIVERHEAD, NY, ..., Riverhead, NY 11901
$329,000

2 beds

|

2 baths

|

1,152 sq ft

|

Manufactured Home

1661 OLD COUNTRY RD 454, 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.
The Seasons at Elwood 63 WINTER PL, HUNTINGTON, NY, 11731, Huntington, NY 11731
$427,767

2 beds

|

2 baths

|

1,108 sq ft

|

Condo

63 WINTER PL, HUNTINGTON, NY, 11731
Stone Ridge Estates 110 JOSEPH LN, HUNTINGTON, NY, 11746, Huntington, NY 11746
$779,000

2 beds

|

2 baths

|

1,695 sq ft

|

Condo

110 JOSEPH LN, HUNTINGTON, NY, 11746
Community: Stone Ridge Estates
Encore Atlantic Shores 140 CHOPIN PL, BROOKHAVEN, NY, 11941, Brookhaven, NY 11941
$865,000

2 beds

|

3 baths

|

2,236 sq ft

|

Condo

140 CHOPIN PL, BROOKHAVEN, NY, 11941
Leisure Village 89 ENFIELD CT B, BROOKHAVEN, NY, 11961, Brookhaven, NY 11961
$469,000

2 beds

|

2 baths

|

1,308 sq ft

|

Condo

89 ENFIELD CT B, BROOKHAVEN, NY, 11961
Community: Leisure Village
Village Vistas 35 THERESA LN, BROOKHAVEN, NY, 11777, Brookhaven, NY 11777
$1,300,000

3 beds

|

4 baths

|

3,000 sq ft

|

Condo

35 THERESA LN, BROOKHAVEN, NY, 11777
Community: Village Vistas
The Village at Oxford Greens 171 COUNTRY CLUB DR 171, OXFORD, CT, 064..., Oxford, CT 06478
$775,000

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
Leisure Glen 19 SAYVILLE CT, BROOKHAVEN, NY, 11961, Brookhaven, NY 11961
$615,000

2 beds

|

2 baths

|

1,666 sq ft

|

Condo

19 SAYVILLE CT, BROOKHAVEN, NY, 11961
Community: Leisure Glen
Want to learn more about 55+ communities in Connecticut? 55places can help!
Questions? Call us: (888) 625-4885
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
Glenwood Village 1661 OLD COUNTRY RD 258, RIVERHEAD, NY, ..., Riverhead, NY 11901
$389,999

2 beds

|

2 baths

|

1,310 sq ft

|

House

1661 OLD COUNTRY RD 258, 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.



Connecticut 55+ Housing Market Trends

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The listings data displayed on this medium comes in part from the Real Estate Information Network Inc. (REIN) and has been authorized by participating listing Broker Members of REIN for display. REIN's listings are based upon Data submitted by its Broker Members, and REIN therefore makes no representation or warranty regarding the accuracy of the Data. All users of REIN's listings database should confirm the accuracy of the listing information directly with the listing agent.
© 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: Aug 20, 2026.
This application does not include information on all of the properties available for sale at this time.

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