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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
5 rating (3 reviews) Founders Ridge
$300ks - $400ks
Founders Ridge, Middletown, CT
New Construction | 55+ age-restricted | Built 2017 - present | 75 homes
5 rating (1 reviews) Sunken Pond Estates
$400ks
Sunken Pond Estates, Riverhead, NY
Resale Only | 55+ age-restricted | Built 2003 - 2005 | 194 homes
5 rating (1 reviews) Encore at Lake Grove
$500ks - $700ks
Encore at Lake Grove, Lake Grove, NY
Resale Only | 55+ age-restricted | Built 2006 - 2007 | 228 homes
Newbury Village
$400ks - $500ks
Newbury Village, Brookfield, CT
New and Resale | 55+ age-restricted | Built 2005 - present | 120 homes
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Park Glen
$300ks - $500ks
Park Glen, New Milford, CT
Resale Only | 55+ age-restricted | Built 2006 - 2015 | 17 homes
The Summit at Bethel
$500ks - $700ks
The Summit at Bethel, Bethel, CT
Resale Only | 55+ age-restricted | Built 2010 - 2021 | 235 homes
Strathmore Gate East
$300ks
Strathmore Gate East, Coram, NY
Resale Only | 55+ age-restricted | Built 1970 - 1975 | 174 homes
Founders Village
$400ks - $500ks
Founders Village, Southold, NY
Resale Only | 55+ age-restricted | Built 1981 - 1985 | 92 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
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.
Stone Ridge Estates
$500ks - $600ks
Stone Ridge Estates, Dix Hills, NY
Resale Only | 55+ age-restricted | Built 2004 - 2013 | 76 homes
Autumn Fields
$200ks - $300ks
Autumn Fields, Enfield, CT
Resale Only | 55+ age-restricted | Built 2004 - 2006 | 56 homes
Kensington Estates
$1Ms
Kensington Estates, Woodbury, NY
New Construction | 55+ age-restricted | Built 2019 - 2021 | 80 homes
The Seasons at Elwood
$800ks - $900ks
The Seasons at Elwood, East Northport, NY
Resale Only | 55+ age-restricted | Built 2018 - 2020 | 256 homes
South Pond Village
$300ks - $400ks
South Pond Village, Bloomfield, CT
Resale Only | 55+ age-restricted | Built 1999 - 2005 | 151 homes
Vineyards at Brookfield
$400ks - $500ks
Vineyards at Brookfield, Center Moriches, NY
New Construction | 55+ age-restricted | Built 2019 - present | 146 homes
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Questions? Call us: (888) 625-4885
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
Billingsgate
$400ks - $600ks
Billingsgate, Simsbury, CT
Resale Only | 55+ age-restricted | Built 2003 - 2006 | 37 homes
Jessup's Landing
$1Ms
Jessup's Landing, Quogue, NY
New and Resale | 55+ age-restricted | Built 2009 - 2016 | 31 homes
The Pines at Bohemia
$400ks - $500ks
The Pines at Bohemia, Bohemia, NY
New Construction | 55+ age-restricted | Built 2019 - present | 20 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 Polo Club at Islandia
$600ks - $700ks
The Polo Club at Islandia, Islandia, NY
New Construction | 55+ age-restricted | Built 2019 - present | 72 homes
The Bridges at Oxford Gre...
$600ks
The Bridges at Oxford Gre..., Oxford, CT
New Construction | 55+ age-restricted | Built 2025 - present | 99 homes
5 rating (2 reviews) Benson Woods
$400ks - $600ks
Benson Woods, Middlebury, CT
New and Resale | 55+ age-restricted | Built 2004 - present | 79 homes
Clockmaker's Hill
$100ks
Clockmaker's Hill, Winsted, CT
Resale Only | 55+ age-restricted | Built 2005 - 2014 | 38 homes
The Village at Buckingham
$300ks - $400ks
The Village at Buckingham, Avon, CT
Resale Only | 55+ age-restricted | Built 2002 - 2006 | 56 homes
Bartlett Hill
$300ks - $400ks
Bartlett Hill, Portland, CT
Resale Only | 55+ age-restricted | Built 2005 - 2011 | 82 homes
Sonoma Woods
$300ks
Sonoma Woods, Middletown, CT
Resale Only | 55+ age-restricted | Built 2005 - 2015 | 68 homes
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Questions? Call us: (888) 625-4885
Pond Spring Village
$300ks
Pond Spring Village, Beacon Falls, CT
New and Resale | 55+ age-restricted | Built 2005 - present | 92 homes
Castle Heights of Cheshir...
$500ks - $600ks
Castle Heights of Cheshir..., Cheshire, CT
Resale Only | 55+ age-restricted | Built 2007 - 2022 | 88 homes
North Woods of Colchester
$300ks - $400ks
North Woods of Colchester, Colchester, CT
New and Resale | 55+ age-restricted | Built 2007 - present | 140 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.
Chimney Hill
$500ks - $700ks
Chimney Hill, Farmington, CT
Resale Only | 55+ age-restricted | Built 2006 - 2013 | 44 homes
RiverWalk
$500ks - $600ks
RiverWalk, Branford, CT
New and Resale | 55+ age-restricted | Built 2007 - present | 60 homes
Newington Ridge Preserve
$300ks - $400ks
Newington Ridge Preserve, Newington, CT
New Construction | 55+ age-restricted | Built 2014 - present | 16 homes
The Powder Forest Homes
$500ks - $700ks
The Powder Forest Homes, Simsbury, CT
Resale Only | 55+ age-restricted | Built 2006 - 2016 | 182 homes
77 Sunset Lane
$400ks - $700ks
77 Sunset Lane, Ridgefield, CT
Resale Only | 55+ age-restricted | Built 2016 - 2018 | 54 homes
Bartlett Hollow
$200ks - $400ks
Bartlett Hollow, Middletown, CT
New Construction | 55+ age-restricted | Built 2015 - present | 25 homes
Autumn Estates
$500ks - $600ks
Autumn Estates, Farmington, CT
Resale Only | 55+ age-restricted | Built 2011 - 2017 | 30 homes
The Atrium of Portland
<$100k
The Atrium of Portland, Portland, CT
Resale Only | 55+ age-restricted | Built 2004 - 2004 | 56 homes
Want to learn more about 55+ communities in Connecticut? 55places can help!
Questions? Call us: (888) 625-4885
Boulder Brook
$200ks
Boulder Brook, Prospect, CT
Resale Only | 55+ age-restricted | Built 2004 - 2006 | 35 homes
Gloria Commons
$200ks - $300ks
Gloria Commons, Milford, CT
Resale Only | 55+ age-restricted | Built 2007 - 2015 | 50 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 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
$410,000

2 beds

|

2 baths

|

1,624 sq ft

|

Manufactured Home

1661 OLD COUNTRY RD 516, RIVERHEAD, NY, ...
Community: Glenwood Village
New Fairfield at St. James 403 CABOT CT, SMITHTOWN, NY, 11780, Smithtown, NY 11780
$425,000

1 beds

|

1 baths

|

1,017 sq ft

|

Condo

403 CABOT CT, SMITHTOWN, NY, 11780
New Meadow Brook Estates 107 MEADOW BROOK RD 107, OXFORD, CT, 064..., Oxford, CT 06478
$625,000

3 beds

|

3 baths

|

1,922 sq ft

|

Condo

107 MEADOW BROOK RD 107, OXFORD, CT, 064...
New Heritage Village 40 HERITAGE VLG F, SOUTHBURY, CT, 06488, Southbury, CT 06488
$270,000

2 beds

|

2 baths

|

1,308 sq ft

|

Condo

40 HERITAGE VLG F, SOUTHBURY, CT, 06488
Community: Heritage Village
Want to learn more about 55+ communities in Connecticut? 55places can help!
Questions? Call us: (888) 625-4885
New Heritage Village 28 HERITAGE CRST B, SOUTHBURY, CT, 06488, Southbury, CT 06488
$429,900

2 beds

|

2 baths

|

1,420 sq ft

|

Condo

28 HERITAGE CRST B, SOUTHBURY, CT, 06488
Community: Heritage Village
New The Summit at Bethel 14 GREAT HILL DR 14, BETHEL, CT, 06801, Bethel, CT 06801
$719,000

3 beds

|

3 baths

|

2,744 sq ft

|

Condo

14 GREAT HILL DR 14, BETHEL, CT, 06801
New Oronoque Village 615 CHEROKEE LN A, STRATFORD, CT, 06614, Stratford, CT 06614
$574,900

2 beds

|

3 baths

|

1,426 sq ft

|

Condo

615 CHEROKEE LN A, STRATFORD, CT, 06614
Community: Oronoque Village
New The Waterways at Moriches 606 BAY VIEW CIR 6, BROOKHAVEN, NY, 1195..., Brookhaven, NY 11955
$749,000

2 beds

|

3 baths

|

1,860 sq ft

|

Condo

606 BAY VIEW CIR 6, BROOKHAVEN, NY, 1195...
New Founders Ridge UNIT 2-41 WEBSTER LN 145, MIDDLETOWN, CT..., Middletown, CT 06457
$689,000

2 beds

|

2 baths

|

1,555 sq ft

UNIT 2-41 WEBSTER LN 145, MIDDLETOWN, CT...
Community: Founders Ridge
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 Glen 20 WAINSCOTT CT, BROOKHAVEN, NY, 11961, Brookhaven, NY 11961
$599,999

2 beds

|

2 baths

|

1,666 sq ft

|

Condo

20 WAINSCOTT CT, BROOKHAVEN, NY, 11961
Community: Leisure Glen
New Leisure Glen 9 OAKDALE CT, BROOKHAVEN, NY, 11961, Brookhaven, NY 11961
$619,000

2 beds

|

2 baths

|

1,882 sq ft

|

House

9 OAKDALE CT, BROOKHAVEN, NY, 11961
Community: Leisure Glen
New Country Pointe Plainview 43101 SILVER BIRCH LN, OYSTER BAY, NY, 1..., Oyster Bay, NY 11803
$1,750,000

2 beds

|

2 baths

|

2,178 sq ft

|

House

43101 SILVER BIRCH LN, OYSTER BAY, NY, 1...
Strathmore Gate East 39 FREEMONT LN, BROOKHAVEN, NY, 11727, Brookhaven, NY 11727
$375,000

2 beds

|

2 baths

|

1,112 sq ft

|

Condo

39 FREEMONT LN, BROOKHAVEN, NY, 11727
Fairfield at St. James 704 FENWAY RD, SMITHTOWN, NY, 11780, Smithtown, NY 11780
$519,000

2 beds

|

2 baths

|

1,292 sq ft

|

Condo

704 FENWAY RD, SMITHTOWN, NY, 11780
The Village at Oxford Greens 84 LINKS WAY 84, OXFORD, CT, 06478, Oxford, CT 06478
$710,000

3 beds

|

3 baths

|

3,496 sq ft

84 LINKS WAY 84, OXFORD, CT, 06478
Want to learn more about 55+ communities in Connecticut? 55places can help!
Questions? Call us: (888) 625-4885
Autumn Fields 24 QUAIL HOLW 24, ENFIELD, CT, 06082, Enfield, CT 06082
$339,000

1 beds

|

2 baths

|

1,235 sq ft

|

Condo

24 QUAIL HOLW 24, ENFIELD, CT, 06082
Community: Autumn Fields
Heritage Village 722 HERITAGE VLG A, SOUTHBURY, CT, 06488, Southbury, CT 06488
$310,000

2 beds

|

2 baths

|

1,432 sq ft

|

Condo

722 HERITAGE VLG A, SOUTHBURY, CT, 06488
Community: Heritage Village
Country Pointe Plainview 30101 SPRUCE POND CIR, OYSTER BAY, NY, 1..., Oyster Bay, NY 11803
$1,200,000

2 beds

|

2 baths

|

1,379 sq ft

|

Condo

30101 SPRUCE POND CIR, OYSTER BAY, NY, 1...
Heritage Village 970 HERITAGE VLG A, SOUTHBURY, CT, 06488, Southbury, CT 06488
$309,000

2 beds

|

2 baths

|

1,432 sq ft

|

Condo

970 HERITAGE VLG A, 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.
Rivington 44 WARRINGTON ROUND 44, DANBURY, CT, 068..., Danbury, CT 06810
$628,000

3 beds

|

3 baths

|

1,600 sq ft

|

Condo

44 WARRINGTON ROUND 44, DANBURY, CT, 068...
Community: Rivington
Leisure Glen 477 LEISURE DR, BROOKHAVEN, NY, 11961, Brookhaven, NY 11961
$589,000

2 beds

|

2 baths

|

1,434 sq ft

|

Condo

477 LEISURE DR, BROOKHAVEN, NY, 11961
Community: Leisure Glen
Country Pointe Plainview 38204 WINTERBERRY DR, OYSTER BAY, NY, 11..., Oyster Bay, NY 11803
$1,585,000

2 beds

|

2 baths

|

1,989 sq ft

|

Condo

38204 WINTERBERRY DR, OYSTER BAY, NY, 11...
Heritage Village 411 HERITAGE VLG B, SOUTHBURY, CT, 06488, Southbury, CT 06488
$427,500

2 beds

|

2 baths

|

1,398 sq ft

|

Condo

411 HERITAGE VLG B, SOUTHBURY, CT, 06488
Community: Heritage Village
Heritage Village 620 HERITAGE VLG B, SOUTHBURY, CT, 06488, Southbury, CT 06488
$319,000

2 beds

|

2 baths

|

1,432 sq ft

|

Condo

620 HERITAGE VLG B, SOUTHBURY, CT, 06488
Community: Heritage Village
Country Pointe Preserve 119 MIA LN 76, BROOKHAVEN, NY, 11980, Brookhaven, NY 11980
$940,000

2 beds

|

3 baths

|

2,187 sq ft

|

Condo

119 MIA LN 76, BROOKHAVEN, NY, 11980
The Village at Oxford Greens 733 CHAMPIONSHIP DR 733, OXFORD, CT, 064..., Oxford, CT 06478
$624,900

2 beds

|

3 baths

|

1,673 sq ft

|

Condo

733 CHAMPIONSHIP DR 733, OXFORD, CT, 064...
Want to learn more about 55+ communities in Connecticut? 55places can help!
Questions? Call us: (888) 625-4885
Sunken Pond Estates 403 WINGED FOOT WAY, RIVERHEAD, NY, 1190..., Riverhead, NY 11901
$520,000

2 beds

|

2 baths

|

1,350 sq ft

|

Condo

403 WINGED FOOT WAY, RIVERHEAD, NY, 1190...
Community: Sunken Pond Estates
Saddle Lakes 157 SCENIC LAKE DR, RIVERHEAD, NY, 11901, Riverhead, NY 11901
$595,000

2 beds

|

2 baths

|

1,386 sq ft

|

Condo

157 SCENIC LAKE DR, RIVERHEAD, NY, 11901
Community: Saddle Lakes
The Greens at Half Hollow 643 VERONA DR, HUNTINGTON, NY, 11747, Huntington, NY 11747
$1,299,999

3 beds

|

3 baths

|

2,500 sq ft

|

Condo

643 VERONA 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.
Regency at Prospect 133 SYCAMORE DR, PROSPECT, CT, 06712, Prospect, CT 06712
$550,000

2 beds

|

3 baths

|

1,850 sq ft

|

Condo

133 SYCAMORE DR, PROSPECT, CT, 06712
Community: Regency at Prospect
Vineyards at Moriches 19 EMILIE DR, BROOKHAVEN, NY, 11934, Brookhaven, NY 11934
$775,000

2 beds

|

3 baths

|

2,251 sq ft

|

Condo

19 EMILIE DR, BROOKHAVEN, NY, 11934
Leisure Glen 279 GLEN DR, BROOKHAVEN, NY, 11961, Brookhaven, NY 11961
$569,999

2 beds

|

2 baths

|

1,542 sq ft

|

Condo

279 GLEN DR, BROOKHAVEN, NY, 11961
Community: Leisure Glen
Newtown Woods 623 BROOKSIDE CT 623, NEWTOWN, CT, 06470, Newtown, CT 06470
$498,900

2 beds

|

2 baths

|

1,504 sq ft

|

Condo

623 BROOKSIDE CT 623, NEWTOWN, CT, 06470
Community: Newtown Woods
Heritage Village 875 HERITAGE VLG A, SOUTHBURY, CT, 06488, Southbury, CT 06488
$225,000

1 beds

|

1 baths

|

928 sq ft

|

Condo

875 HERITAGE VLG A, SOUTHBURY, CT, 06488
Community: Heritage Village
The Village at Buckingham 13 KENINGTON RD 13, AVON, CT, 06001, Avon, CT 06001
$639,900

3 beds

|

3 baths

|

2,024 sq ft

|

Condo

13 KENINGTON RD 13, AVON, CT, 06001
Heritage Village 23 HERITAGE VLG A, SOUTHBURY, CT, 06488, Southbury, CT 06488
$269,900

2 beds

|

2 baths

|

1,032 sq ft

|

Condo

23 HERITAGE VLG A, SOUTHBURY, CT, 06488
Community: Heritage Village
Heritage Village 4 HERITAGE CIR A, SOUTHBURY, CT, 06488, Southbury, CT 06488
$465,000

2 beds

|

2 baths

|

1,398 sq ft

|

Condo

4 HERITAGE CIR A, SOUTHBURY, CT, 06488
Community: Heritage Village
Want to learn more about 55+ communities in Connecticut? 55places can help!
Questions? Call us: (888) 625-4885
Heritage Village 569 HERITAGE VLG A, SOUTHBURY, CT, 06488, Southbury, CT 06488
$315,000

2 beds

|

2 baths

|

1,032 sq ft

|

Condo

569 HERITAGE VLG A, SOUTHBURY, CT, 06488
Community: Heritage Village
Encore at Lake Grove 20 SONATA CT, BROOKHAVEN, NY, 11755, Brookhaven, NY 11755
$650,000

2 beds

|

3 baths

|

1,378 sq ft

|

Condo

20 SONATA CT, BROOKHAVEN, NY, 11755
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: Sep 14, 2026.
This application does not include information on all of the properties available for sale at this time.

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