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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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The Cottages at Wire Mill
$1Ms
The Cottages at Wire Mill, Stamford, CT
New Construction | 55+ age-restricted | Built 2026 - present | 9 homes
Long Hill Village
$300ks - $400ks
Long Hill Village, Trumbull, CT
Resale Only | 55+ age-restricted | Built 1997 - 1999 | 71 homes
Liberty at Newtown
$300ks - $400ks
Liberty at Newtown, Newtown, CT
Resale Only | 55+ age-restricted | Built 2003 - 2007 | 96 homes
Park Glen
$300ks - $500ks
Park Glen, New Milford, CT
Resale Only | 55+ age-restricted | Built 2006 - 2015 | 17 homes
Setauket Meadows
$500ks - $600ks
Setauket Meadows, Setauket, NY
Resale Only | 55+ age-restricted | Built 2005 - 2007 | 150 homes
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The Summit at Bethel
$500ks - $700ks
The Summit at Bethel, Bethel, CT
Resale Only | 55+ age-restricted | Built 2010 - 2021 | 235 homes
Founders Village
$400ks - $500ks
Founders Village, Southold, NY
Resale Only | 55+ age-restricted | Built 1981 - 1985 | 92 homes
Country Pointe Preserve
$600ks - $900ks
Country Pointe PreserveYaphank, NY
New Construction | 55+ age-restricted | Built 2024 - present | 152 homes
Bidwell Village
$300ks - $400ks
Bidwell Village, Coventry, CT
New Construction | 55+ age-restricted | Built 2020 - present | 37 homes
The Village at Buckingham
$300ks - $400ks
The Village at Buckingham, Avon, CT
Resale Only | 55+ age-restricted | Built 2002 - 2006 | 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.
South Pond Village
$300ks - $400ks
South Pond Village, Bloomfield, CT
Resale Only | 55+ age-restricted | Built 1999 - 2005 | 151 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 Moriches
$500ks - $600ks
Vineyards at Moriches, Center Moriches, NY
Resale Only | 55+ age-restricted | Built 2008 - 2014 | 92 homes
Vineyards at Brookfield
$400ks - $500ks
Vineyards at Brookfield, Center Moriches, NY
New Construction | 55+ age-restricted | Built 2019 - present | 146 homes
5 rating (3 reviews) Founders Ridge
$300ks - $400ks
Founders Ridge, Middletown, CT
New Construction | 55+ age-restricted | Built 2017 - present | 75 homes
Sonoma Woods
$300ks
Sonoma Woods, Middletown, CT
Resale Only | 55+ age-restricted | Built 2005 - 2015 | 68 homes
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The Seasons at East North...
$700ks
The Seasons at East North..., East Northport, NY
New Construction | 55+ age-restricted | Built 2023 - present | 190 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
Pond Spring Village
$300ks
Pond Spring Village, Beacon Falls, CT
New and Resale | 55+ age-restricted | Built 2005 - present | 92 homes
Billingsgate
$400ks - $600ks
Billingsgate, Simsbury, CT
Resale Only | 55+ age-restricted | Built 2003 - 2006 | 37 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 at Prospect
$300ks - $400ks
Regency at Prospect, Prospect, CT
Resale Only | 55+ age-restricted | Built 2006 - 2020 | 379 homes
Gloria Commons
$200ks - $300ks
Gloria Commons, Milford, CT
Resale Only | 55+ age-restricted | Built 2007 - 2015 | 50 homes
Hopmeadow Place
$200ks - $300ks
Hopmeadow Place, Simsbury, CT
Resale Only | 55+ age-restricted | Built 2005 - 2005 | 66 homes
Oak Meadow Estates
$200ks - $300ks
Oak Meadow Estates, Torrington, CT
New and Resale | 55+ age-restricted | Built 2013 - present | 31 homes
RiverBend Estates
$400ks
RiverBend Estates, Oxford, CT
New and Resale | 55+ age-restricted | Built 2012 - present | 25 homes
Summer Wind Estates
$300ks - $400ks
Summer Wind Estates, North Haven, CT
New Construction | 55+ age-restricted | Built 2015 - present | 18 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
Want to learn more about 55+ communities in Connecticut? 55places can help!
Questions? Call us: (888) 625-4885
Cobblestone Court
$400ks - $500ks
Cobblestone Court, Essex, CT
New and Resale | 55+ age-restricted | Built 2017 - present | 8 homes
Forest Mews
$300ks - $400ks
Forest Mews, Avon, CT
Resale Only | 55+ age-restricted | Built 2001 - 2004 | 40 homes
The Village at Hunt Glen
$300ks
The Village at Hunt Glen, Granby, CT
Resale Only | 55+ age-restricted | Built 2003 - 2006 | 69 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.
O'Meara Farm
$400ks
O'Meara Farm, Farmington, CT
Resale Only | 55+ age-restricted | Built 1998 - 2005 | 104 homes
The Coach Homes at Ridgef...
$300ks - $400ks
The Coach Homes at Ridgef..., Ridgefield, CT
New Construction | 55+ age-restricted | Built 2019 - present | 30 homes
Evergreen
$400ks - $500ks
Evergreen, Cromwell, CT
New and Resale | 55+ age-restricted | Built 2005 - present | 52 homes
Rivington Landing
$500ks
Rivington Landing, Danbury, CT
New Construction | Age-targeted | Built 2025 - 2026 | 25 homes
Whitney Glen
$500ks - $600ks
Whitney Glen, Westport, CT
Resale Only | 55+ age-restricted | Built 1982 - 1982 | 62 homes
Eastport Meadows
$400ks
Eastport Meadows, Eastport, NY
Resale Only | 55+ age-restricted | Built 2009 - 2016 | 50 homes
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
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
Autumn Fields
$200ks - $300ks
Autumn Fields, Enfield, CT
Resale Only | 55+ age-restricted | Built 2004 - 2006 | 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.
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 Glenwood Village 1661 OLD COUNTRY RD 516, RIVERHEAD, NY, ..., Riverhead, NY 11901
$410,000

2 beds

|

2 baths

|

1,624 sq ft

|

Manufactured Home

1661 OLD COUNTRY RD 516, RIVERHEAD, NY, ...
Community: Glenwood Village
New Meadow Brook Estates 802 SAGE HILL DR 802, OXFORD, CT, 06478, Oxford, CT 06478
$675,000

2 beds

|

3 baths

|

2,258 sq ft

|

Condo

802 SAGE HILL DR 802, OXFORD, CT, 06478
New Leisure Knoll 346 EDINBURGH DR, BROOKHAVEN, NY, 11961, Brookhaven, NY 11961
$419,000

2 beds

|

1 baths

|

1,050 sq ft

|

Condo

346 EDINBURGH DR, BROOKHAVEN, NY, 11961
Community: Leisure Knoll
New Sunken Pond Estates 3102 AMEN COR, RIVERHEAD, NY, 11901, Riverhead, NY 11901
$525,000

2 beds

|

2 baths

|

1,587 sq ft

|

Condo

3102 AMEN COR, RIVERHEAD, NY, 11901
Community: Sunken Pond Estates
Want to learn more about 55+ communities in Connecticut? 55places can help!
Questions? Call us: (888) 625-4885
New Rivington 71 WARRINGTON ROUND 71, DANBURY, CT, 068..., Danbury, CT 06810
$669,900

3 beds

|

3 baths

|

1,704 sq ft

|

Condo

71 WARRINGTON ROUND 71, DANBURY, CT, 068...
Community: Rivington
New Rivington 3 HUMBER HILL RD 3, DANBURY, CT, 06810, Danbury, CT 06810
$774,900

3 beds

|

4 baths

|

2,120 sq ft

|

Condo

3 HUMBER HILL RD 3, DANBURY, CT, 06810
Community: Rivington
New Leisure Knoll 177 CANTERBURY DR, BROOKHAVEN, NY, 11961, Brookhaven, NY 11961
$379,900

2 beds

|

1 baths

|

1,116 sq ft

|

Condo

177 CANTERBURY DR, BROOKHAVEN, NY, 11961
Community: Leisure Knoll
New The Greens at Half Hollow 1067 SAVOY DR, HUNTINGTON, NY, 11747, Huntington, NY 11747
$699,000

2 beds

|

2 baths

|

1,150 sq ft

|

Condo

1067 SAVOY DR, HUNTINGTON, NY, 11747
New Strathmore Gate East 46 FORGE LN, BROOKHAVEN, NY, 11727, Brookhaven, NY 11727
$429,999

2 beds

|

2 baths

|

1,112 sq ft

|

House

46 FORGE LN, BROOKHAVEN, NY, 11727
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 Foxwood Village 1407 MIDDLE RD 271, RIVERHEAD, NY, 11933, Riverhead, NY 11933
$465,000

3 beds

|

2 baths

|

1,792 sq ft

|

Manufactured Home

1407 MIDDLE RD 271, RIVERHEAD, NY, 11933
Community: Foxwood Village
New The Greens at Half Hollow 581 VERONA DR, HUNTINGTON, NY, 11747, Huntington, NY 11747
$1,199,900

2 beds

|

3 baths

|

1,941 sq ft

|

Condo

581 VERONA DR, HUNTINGTON, NY, 11747
New Granite Woods 35 NUTMEG RD B5, MIDDLEBURY, CT, 06762, Middlebury, CT 06762
$250,000

2 beds

|

1 baths

|

890 sq ft

|

Condo

35 NUTMEG RD B5, MIDDLEBURY, CT, 06762
Community: Granite Woods
New Kensington Estates 46 PLAINVIEW RD, OYSTER BAY, NY, 11797, Oyster Bay, NY 11797
$2,049,888

6 beds

|

5 baths

|

4,333 sq ft

|

House

46 PLAINVIEW RD, OYSTER BAY, NY, 11797
Community: Kensington Estates
New Greenwood Village 33 DOGWOOD LN, BROOKHAVEN, NY, 11949, Brookhaven, NY 11949
$225,000

2 beds

|

2 baths

|

1,134 sq ft

|

House

33 DOGWOOD LN, BROOKHAVEN, NY, 11949
Community: Greenwood Village
New Windcrest East 90 GOLDEN SPRUCE DR, RIVERHEAD, NY, 1193..., Riverhead, NY 11933
$799,000

3 beds

|

3 baths

|

2,620 sq ft

|

Condo

90 GOLDEN SPRUCE DR, RIVERHEAD, NY, 1193...
Community: Windcrest East
Want to learn more about 55+ communities in Connecticut? 55places can help!
Questions? Call us: (888) 625-4885
New Windcrest East 29 GOLDEN SPRUCE DR, RIVERHEAD, NY, 1193..., Riverhead, NY 11933
$799,990

3 beds

|

3 baths

|

2,531 sq ft

|

Condo

29 GOLDEN SPRUCE DR, RIVERHEAD, NY, 1193...
Community: Windcrest East
New Leisure Glen 9 AMAGANSETT CT, BROOKHAVEN, NY, 11961, Brookhaven, NY 11961
$519,900

2 beds

|

2 baths

|

1,476 sq ft

|

Condo

9 AMAGANSETT CT, BROOKHAVEN, NY, 11961
Community: Leisure Glen
New Long Hill Village 48 CIDER MILL LN, TRUMBULL, CT, 06611, Trumbull, CT 06611
$499,900

2 beds

|

2 baths

|

1,070 sq ft

|

Condo

48 CIDER MILL LN, TRUMBULL, CT, 06611
Community: Long Hill Village
New Meadow Brook Estates 130 MEADOW BROOK RD 130, OXFORD, CT, 064..., Oxford, CT 06478
$599,000

2 beds

|

3 baths

|

1,920 sq ft

|

Condo

130 MEADOW BROOK RD 130, 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.
Greenwood Village 10 GREENWOOD BLVD, BROOKHAVEN, NY, 11949, Brookhaven, NY 11949
$179,999

2 beds

|

1 baths

|

938 sq ft

|

Condo

10 GREENWOOD BLVD, BROOKHAVEN, NY, 11949
Community: Greenwood Village
Leisure Knoll 148 LAURANCE LN, BROOKHAVEN, NY, 11961, Brookhaven, NY 11961
$499,000

2 beds

|

2 baths

|

1,096 sq ft

|

Condo

148 LAURANCE LN, BROOKHAVEN, NY, 11961
Community: Leisure Knoll
Fairfield at St. James 1406 GOTHAM CT, SMITHTOWN, NY, 11780, Smithtown, NY 11780
$579,803

2 beds

|

2 baths

|

1,321 sq ft

|

Condo

1406 GOTHAM CT, SMITHTOWN, NY, 11780
Long Hill Village 36 LONG HILL PL, TRUMBULL, CT, 06611, Trumbull, CT 06611
$550,000

2 beds

|

3 baths

|

1,370 sq ft

|

Condo

36 LONG HILL PL, TRUMBULL, CT, 06611
Community: Long Hill Village
Regency Meadows 17 REGENCY CIR, TRUMBULL, CT, 06611, Trumbull, CT 06611
$765,000

3 beds

|

4 baths

|

2,597 sq ft

17 REGENCY CIR, TRUMBULL, CT, 06611
Community: Regency Meadows
Greenwood Village 1 LIMETREE DR, BROOKHAVEN, NY, 11949, Brookhaven, NY 11949
$268,833

2 beds

|

2 baths

|

1,027 sq ft

|

Condo

1 LIMETREE DR, BROOKHAVEN, NY, 11949
Community: Greenwood Village
Foxwood Village 1407 MIDDLE RD 245, RIVERHEAD, NY, 11933, Riverhead, NY 11933
$349,000

3 beds

|

2 baths

|

1,368 sq ft

|

House

1407 MIDDLE RD 245, RIVERHEAD, NY, 11933
Community: Foxwood Village
Want to learn more about 55+ communities in Connecticut? 55places can help!
Questions? Call us: (888) 625-4885
Setauket Meadows 33 BLAIR RD, BROOKHAVEN, NY, 11733, Brookhaven, NY 11733
$849,999

2 beds

|

3 baths

|

1,700 sq ft

|

Condo

33 BLAIR RD, BROOKHAVEN, NY, 11733
Community: Setauket Meadows
Encore at Lake Grove 163 SYMPHONY DR, BROOKHAVEN, NY, 11755, Brookhaven, NY 11755
$645,000

2 beds

|

3 baths

|

1,378 sq ft

|

Condo

163 SYMPHONY DR, BROOKHAVEN, NY, 11755
Rivington 1 RIVINGTON WAY 306, DANBURY, CT, 06810, Danbury, CT 06810
$565,000

2 beds

|

2 baths

|

1,549 sq ft

|

Condo

1 RIVINGTON WAY 306, DANBURY, CT, 06810
Community: Rivington
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 at Woodbridge 18 HILLCREST DR 18, WOODBRIDGE, CT, 0652..., Woodbridge, CT 06525
$829,900

3 beds

|

3 baths

|

2,412 sq ft

|

Condo

18 HILLCREST DR 18, WOODBRIDGE, CT, 0652...
Heritage Village 2 HERITAGE CRST C, SOUTHBURY, CT, 06488, Southbury, CT 06488
$469,900

2 beds

|

2 baths

|

1,420 sq ft

|

Condo

2 HERITAGE CRST C, SOUTHBURY, CT, 06488
Community: Heritage Village
Spring Lake Village 19 HICKORY HL 19, SOUTHINGTON, CT, 06489, Southington, CT 06489
$256,000

2 beds

|

2 baths

|

1,285 sq ft

|

Condo

19 HICKORY HL 19, SOUTHINGTON, CT, 06489
Community: Spring Lake Village
Heritage Village 4 HERITAGE CRST C, SOUTHBURY, CT, 06488, Southbury, CT 06488
$399,000

2 beds

|

2 baths

|

1,306 sq ft

|

Condo

4 HERITAGE CRST C, SOUTHBURY, CT, 06488
Community: Heritage Village
Heritage Village 682 HERITAGE VLG A, SOUTHBURY, CT, 06488, Southbury, CT 06488
$350,000

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
Stone Ridge Estates 118 JOSEPH LN, HUNTINGTON, NY, 11746, Huntington, NY 11746
$779,000

2 beds

|

2 baths

|

1,447 sq ft

|

Condo

118 JOSEPH LN, HUNTINGTON, NY, 11746
Community: Stone Ridge Estates
Want to learn more about 55+ communities in Connecticut? 55places can help!
Questions? Call us: (888) 625-4885
Heritage Village 883 HERITAGE VLG C, SOUTHBURY, CT, 06488, Southbury, CT 06488
$324,900

2 beds

|

2 baths

|

1,000 sq ft

|

Condo

883 HERITAGE VLG C, SOUTHBURY, CT, 06488
Community: Heritage Village
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
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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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: Oct 11, 2026.
This application does not include information on all of the properties available for sale at this time.

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