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Connecticut 55+ active adult communities & homes for sale

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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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
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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 reviews) Beckley Farms
$300ks - $400ks
Beckley Farms, Berlin, CT
New and Resale | 55+ age-restricted | Built 2010 - present | 170 homes
4 rating (8 reviews) Glenwood Village
$100ks - $200ks
Glenwood Village, Riverhead, NY
New and Resale | 55+ age-restricted | Built 1959 - present | 588 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.
The Waterways at Moriches
$300ks - $600ks
The Waterways at Moriches, Moriches, NY
Resale Only | 55+ age-restricted | Built 1985 - 1999 | 343 homes
3.7 rating (3 reviews) Greenwood Village
$100ks
Greenwood Village, Manorville, NY
Resale Only | 55+ age-restricted | Built 1980 - 2000 | 512 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
Leisure Village
$100ks - $300ks
Leisure Village, Ridge, NY
Resale Only | 55+ age-restricted | Built 1969 - 1986 | 1,500 homes
Leisure Glen
$300ks - $400ks
Leisure Glen, Ridge, NY
Resale Only | 55+ age-restricted | Built 1985 - 2010 | 646 homes
5 rating (1 reviews) Encore Atlantic Shores
$500ks - $800ks
Encore Atlantic Shores, Eastport, NY
Resale Only | 55+ age-restricted | Built 2004 - 2011 | 240 homes
Want to learn more about 55+ communities in Connecticut? 55places can help!
Questions? Call us: (888) 625-4885
Harmony Place
$400ks - $500ks
Harmony Place, Rutland, MA
New Construction | 55+ age-restricted | Built 2023 - present | 142 homes
Country Pointe Plainview
$700ks - $1Ms
Country Pointe Plainview, Plainview, NY
New Construction | 55+ age-restricted | Built 2017 - present | 660 homes
Stoneleigh Woods at River...
$500ks
Stoneleigh Woods at River..., Riverhead, NY
Resale Only | 55+ age-restricted | Built 2007 - 2016 | 176 homes
Leisure Knoll
$200ks - $400ks
Leisure Knoll, Ridge, NY
Resale Only | 55+ age-restricted | Built 1972 - 1982 | 701 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.
5 rating (1 reviews) Westhampton Pines
$900ks - $1Ms
Westhampton Pines, Westhampton, NY
Resale Only | 55+ age-restricted | Built 2005 - 2013 | 189 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
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
Vineyards at Brookfield
$400ks - $500ks
Vineyards at Brookfield, Center Moriches, NY
New Construction | 55+ age-restricted | Built 2019 - present | 146 homes
Liberty at Newtown
$300ks - $400ks
Liberty at Newtown, Newtown, CT
Resale Only | 55+ age-restricted | Built 2003 - 2007 | 96 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
5 rating (1 reviews) Newtown Woods
$300ks - $500ks
Newtown Woods, Newtown, CT
New and Resale | 55+ age-restricted | Built 2011 - present | 178 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
Woodridge Strathmore Terr...
$200ks - $300ks
Woodridge Strathmore Terr..., Mount Sinai, NY
Resale Only | 55+ age-restricted | Built 1974 - 1985 | 226 homes
3.5 rating (2 reviews) Foxwood Village
$200ks - $400ks
Foxwood Village, Calverton, NY
Resale Only | 55+ age-restricted | Built 1986 - 2007 | 294 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.
Country Pointe Preserve
$600ks - $900ks
Country Pointe PreserveYaphank, NY
New Construction | 55+ age-restricted | Built 2024 - present | 152 homes
The Cottages at Wire Mill
$1Ms
The Cottages at Wire Mill, Stamford, CT
New Construction | 55+ age-restricted | Built 2026 - present | 9 homes
The Summit at Bethel
$500ks - $700ks
The Summit at Bethel, Bethel, CT
Resale Only | 55+ age-restricted | Built 2010 - 2021 | 235 homes
Baldwin Station
$400ks
Baldwin Station, Milford, CT
Resale Only | 55+ age-restricted | Built 2001 - 2003 | 82 homes
Saddle Lakes
$400ks - $500ks
Saddle Lakes, Riverhead, NY
Resale Only | 55+ age-restricted | Built 2000 - 2002 | 196 homes
Newbury Village
$400ks - $500ks
Newbury Village, Brookfield, CT
New and Resale | 55+ age-restricted | Built 2005 - present | 120 homes
Granite Woods
$600ks - $700ks
Granite Woods, Middlebury, CT
New Construction | 55+ age-restricted | Built 2020 - present | 24 homes
Shaker Heights
$400ks - $500ks
Shaker Heights, Enfield, CT
New Construction | 55+ age-restricted | Built 2018 - present | 77 homes
Want to learn more about 55+ communities in Connecticut? 55places can help!
Questions? Call us: (888) 625-4885
12...3
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 Heritage Village 738 HERITAGE VLG A, SOUTHBURY, CT, 06488, Southbury, CT 06488
$329,900

2 beds

|

2 baths

|

1,398 sq ft

|

Condo

738 HERITAGE VLG A, SOUTHBURY, CT, 06488
Community: Heritage Village
New Granite Woods 35 NUTMEG RD B2, MIDDLEBURY, CT, 06762, Middlebury, CT 06762
$239,900

1 beds

|

1 baths

|

889 sq ft

|

Condo

35 NUTMEG RD B2, MIDDLEBURY, CT, 06762
Community: Granite Woods
Want to learn more about 55+ communities in Connecticut? 55places can help!
Questions? Call us: (888) 625-4885
New Woodridge Strathmore Terrace 6 COBBLESTONE WAY, BROOKHAVEN, NY, 11766, Brookhaven, NY 11766
$430,000

2 beds

|

2 baths

|

1,151 sq ft

|

Condo

6 COBBLESTONE WAY, BROOKHAVEN, NY, 11766
New Oronoque Village 393 OTTAWA LN B, STRATFORD, CT, 06614, Stratford, CT 06614
$350,000

1 beds

|

3 baths

|

1,118 sq ft

|

Condo

393 OTTAWA LN B, STRATFORD, CT, 06614
Community: Oronoque Village
New Foxwood Village 1407 MIDDLE RD 265, RIVERHEAD, NY, 11933, Riverhead, NY 11933
$469,999

3 beds

|

2 baths

|

1,792 sq ft

|

Manufactured Home

1407 MIDDLE RD 265, RIVERHEAD, NY, 11933
Community: Foxwood Village
New The Greens at Half Hollow 602 BARDINI DR, HUNTINGTON, NY, 11747, Huntington, NY 11747
$1,199,000

2 beds

|

4 baths

|

1,941 sq ft

|

Condo

602 BARDINI DR, HUNTINGTON, NY, 11747
New Leisure Village 463 B OLDHAM CT, BROOKHAVEN, NY, 11961, Brookhaven, NY 11961
$389,990

2 beds

|

1 baths

|

1,074 sq ft

|

Condo

463 B OLDHAM CT, BROOKHAVEN, NY, 11961
Community: Leisure 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 Leisure Village 472 DARWEN DR, BROOKHAVEN, NY, 11961, Brookhaven, NY 11961
$408,000

2 beds

|

2 baths

|

1,200 sq ft

|

Condo

472 DARWEN DR, BROOKHAVEN, NY, 11961
Community: Leisure Village
New South Pond Village 78 SILO WAY 78, BLOOMFIELD, CT, 06002, Bloomfield, CT 06002
$289,500

3 beds

|

3 baths

|

1,639 sq ft

|

Condo

78 SILO WAY 78, BLOOMFIELD, CT, 06002
Community: South Pond Village
New Plymouth Estates at Mount Sinai 7 POND CIR, BROOKHAVEN, NY, 11766, Brookhaven, NY 11766
$665,000

2 beds

|

2 baths

|

1,274 sq ft

|

Condo

7 POND CIR, BROOKHAVEN, NY, 11766
New Leisure Knoll 152A LAURANCE LN A, BROOKHAVEN, NY, 1196..., Brookhaven, NY 11961
$399,999

2 beds

|

1 baths

|

724 sq ft

|

Condo

152A LAURANCE LN A, BROOKHAVEN, NY, 1196...
Community: Leisure Knoll
New Newbury Village 23 STILL WATER CIR 23, BROOKFIELD, CT, 0..., Brookfield, CT 06804
$735,000

3 beds

|

4 baths

|

2,684 sq ft

|

Condo

23 STILL WATER CIR 23, BROOKFIELD, CT, 0...
Community: Newbury Village
New Leisure Glen 6 OAKDALE CT, BROOKHAVEN, NY, 11961, Brookhaven, NY 11961
$559,000

2 beds

|

2 baths

|

1,666 sq ft

|

Condo

6 OAKDALE 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
New 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
New Oronoque Village 138 BISON LN B, STRATFORD, CT, 06614, Stratford, CT 06614
$480,000

2 beds

|

3 baths

|

1,438 sq ft

138 BISON LN B, STRATFORD, CT, 06614
Community: Oronoque Village
New Leisure Village 134 EASTBOURNE CT A, BROOKHAVEN, NY, 119..., Brookhaven, NY 11961
$349,999

2 beds

|

1 baths

|

836 sq ft

|

Condo

134 EASTBOURNE CT A, BROOKHAVEN, NY, 119...
Community: Leisure Village
New Leisure Glen 454 LEISURE DR, BROOKHAVEN, NY, 11961, Brookhaven, NY 11961
$649,000

2 beds

|

2 baths

|

1,652 sq ft

|

Condo

454 LEISURE DR, 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 Heritage Village 857 HERITAGE VLG A, SOUTHBURY, CT, 06488, Southbury, CT 06488
$235,000

2 beds

|

2 baths

|

1,071 sq ft

|

Condo

857 HERITAGE VLG A, SOUTHBURY, CT, 06488
Community: Heritage Village
New Heritage Village 9 HERITAGE CIR A, SOUTHBURY, CT, 06488, Southbury, CT 06488
$275,000

2 beds

|

2 baths

|

1,071 sq ft

|

Condo

9 HERITAGE CIR A, SOUTHBURY, CT, 06488
Community: Heritage Village
New Heritage Village 353 HERITAGE VLG B, SOUTHBURY, CT, 06488, Southbury, CT 06488
$329,900

2 beds

|

2 baths

|

1,432 sq ft

|

Condo

353 HERITAGE VLG B, SOUTHBURY, CT, 06488
Community: Heritage Village
New Woodridge Strathmore Terrace 89 HEARTHSIDE DR, BROOKHAVEN, NY, 11766, Brookhaven, NY 11766
$409,999

1 beds

|

1 baths

|

720 sq ft

|

Condo

89 HEARTHSIDE DR, BROOKHAVEN, NY, 11766
New Heritage Village 559 HERITAGE VLG B, SOUTHBURY, CT, 06488, Southbury, CT 06488
$315,000

2 beds

|

2 baths

|

1,432 sq ft

|

Condo

559 HERITAGE VLG B, SOUTHBURY, CT, 06488
Community: Heritage Village
Rivington 714 CENTER MEADOW LN 714, DANBURY, CT, 0..., Danbury, CT 06810
$497,000

2 beds

|

2 baths

|

1,258 sq ft

|

Condo

714 CENTER MEADOW LN 714, DANBURY, CT, 0...
Community: Rivington
Eagles Walk at East Quogue 1401 AERIE WAY, SOUTHAMPTON, NY, 11942, Southampton, NY 11942
$565,000

2 beds

|

2 baths

|

1,271 sq ft

|

Condo

1401 AERIE WAY, SOUTHAMPTON, NY, 11942
Want to learn more about 55+ communities in Connecticut? 55places can help!
Questions? Call us: (888) 625-4885
Heritage Village 397 HERITAGE VLG B, SOUTHBURY, CT, 06488, Southbury, CT 06488
$424,900

2 beds

|

2 baths

|

1,432 sq ft

|

Condo

397 HERITAGE VLG B, SOUTHBURY, CT, 06488
Community: Heritage Village
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
Founders Village 2555 YOUNGS AVE 3C, SOUTHOLD, NY, 11971, Southold, NY 11971
$550,000

2 beds

|

2 baths

|

1,100 sq ft

|

Condo

2555 YOUNGS AVE 3C, SOUTHOLD, NY, 11971
Community: Founders 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 Greens at Half Hollow 559 BARDINI DR, HUNTINGTON, NY, 11747, Huntington, NY 11747
$1,299,000

3 beds

|

3 baths

|

2,396 sq ft

|

Condo

559 BARDINI DR, HUNTINGTON, NY, 11747
Leisure Knoll 185 KINGSTON DR, BROOKHAVEN, NY, 11961, Brookhaven, NY 11961
$405,000

2 beds

|

1 baths

|

1,014 sq ft

|

Condo

185 KINGSTON DR, BROOKHAVEN, NY, 11961
Community: Leisure Knoll
Heritage Village 549 HERITAGE VLG D, SOUTHBURY, CT, 06488, Southbury, CT 06488
$164,900

2 beds

|

2 baths

|

1,044 sq ft

|

Condo

549 HERITAGE VLG D, SOUTHBURY, CT, 06488
Community: Heritage Village
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
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
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
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
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
Want to learn more about 55+ communities in Connecticut? 55places can help!
Questions? Call us: (888) 625-4885
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...
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
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: Aug 27, 2026.
This application does not include information on all of the properties available for sale at this time.

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