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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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Vineyards at Moriches
$500ks - $600ks
Vineyards at Moriches, Center Moriches, NY
Resale Only | 55+ age-restricted | Built 2008 - 2014 | 92 homes
5 rating (1 reviews) Sunken Pond Estates
$400ks
Sunken Pond Estates, Riverhead, NY
Resale Only | 55+ age-restricted | Built 2003 - 2005 | 194 homes
Strathmore Gate East
$300ks
Strathmore Gate East, Coram, NY
Resale Only | 55+ age-restricted | Built 1970 - 1975 | 174 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
Want to learn more about 55+ communities in Connecticut? 55places can help!
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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
Vineyards at Brookfield
$400ks - $500ks
Vineyards at Brookfield, Center Moriches, NY
New Construction | 55+ age-restricted | Built 2019 - present | 146 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
Granite Woods
$600ks - $700ks
Granite Woods, Middlebury, CT
New Construction | 55+ age-restricted | Built 2020 - present | 24 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 Woodbridge
$500ks - $700ks
Regency at Woodbridge, Woodbridge, CT
New Construction | 55+ age-restricted | Built 2023 - present | 70 homes
Regency at Prospect
$300ks - $400ks
Regency at Prospect, Prospect, CT
Resale Only | 55+ age-restricted | Built 2006 - 2020 | 379 homes
Newbury Village
$400ks - $500ks
Newbury Village, Brookfield, CT
New and Resale | 55+ age-restricted | Built 2005 - present | 120 homes
5 rating (3 reviews) Founders Ridge
$300ks - $400ks
Founders Ridge, Middletown, CT
New Construction | 55+ age-restricted | Built 2017 - present | 75 homes
Hopmeadow Place
$200ks - $300ks
Hopmeadow Place, Simsbury, CT
Resale Only | 55+ age-restricted | Built 2005 - 2005 | 66 homes
Park Glen
$300ks - $500ks
Park Glen, New Milford, CT
Resale Only | 55+ age-restricted | Built 2006 - 2015 | 17 homes
Want to learn more about 55+ communities in Connecticut? 55places can help!
Questions? Call us: (888) 625-4885
Regency Meadows
$500ks
Regency Meadows, Trumbull, CT
Resale Only | 55+ age-restricted | Built 2003 - 2005 | 51 homes
South Pond Village
$300ks - $400ks
South Pond Village, Bloomfield, CT
Resale Only | 55+ age-restricted | Built 1999 - 2005 | 151 homes
The Bridges at Oxford Gre...
$600ks
The Bridges at Oxford Gre..., Oxford, CT
New Construction | 55+ age-restricted | Built 2025 - present | 99 homes
Applegate Estates
$500ks - $400ks
Applegate Estates, Southington, CT
New and Resale | 55+ age-restricted | Built 2010 - 2025 | 94 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.
Rivington Landing
$500ks
Rivington Landing, Danbury, CT
New Construction | Age-targeted | Built 2025 - 2026 | 25 homes
Eastport Meadows
$400ks
Eastport Meadows, Eastport, NY
Resale Only | 55+ age-restricted | Built 2009 - 2016 | 50 homes
The Seasons at Plainview
$500ks - $600ks
The Seasons at Plainview, Plainview, NY
Resale Only | 55+ age-restricted | Built 2006 - 2007 | 134 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
Country Village Estates
$300ks
Country Village Estates, Coram, NY
Resale Only | 55+ age-restricted | Built 1993 - 2001 | 195 homes
Want to learn more about 55+ communities in Connecticut? 55places can help!
Questions? Call us: (888) 625-4885
Stone Ridge Estates
$500ks - $600ks
Stone Ridge Estates, Dix Hills, NY
Resale Only | 55+ age-restricted | Built 2004 - 2013 | 76 homes
3.5 rating (2 reviews) Harvest Pointe
$800ks - $3Ms
Harvest Pointe, Cutchogue, NY
New Construction | 55+ age-restricted | Built 2017 - present | 124 homes
Jessup's Landing
$1Ms
Jessup's Landing, Quogue, NY
New and Resale | 55+ age-restricted | Built 2009 - 2016 | 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.
The Pines at Bohemia
$400ks - $500ks
The Pines at Bohemia, Bohemia, NY
New Construction | 55+ age-restricted | Built 2019 - present | 20 homes
The Polo Club at Islandia
$600ks - $700ks
The Polo Club at Islandia, Islandia, NY
New Construction | 55+ age-restricted | Built 2019 - present | 72 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
Pond Spring Village
$300ks
Pond Spring Village, Beacon Falls, CT
New and Resale | 55+ age-restricted | Built 2005 - present | 92 homes
Want to learn more about 55+ communities in Connecticut? 55places can help!
Questions? Call us: (888) 625-4885
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.
New 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
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 Heritage Village 886 HERITAGE VLG B, SOUTHBURY, CT, 06488, Southbury, CT 06488
$414,900

2 beds

|

2 baths

|

1,398 sq ft

|

Condo

886 HERITAGE VLG B, SOUTHBURY, CT, 06488
Community: Heritage Village
New Encore at Lake Grove 39 SYMPHONY DR, BROOKHAVEN, NY, 11755, Brookhaven, NY 11755
$625,000

2 beds

|

3 baths

|

1,700 sq ft

|

Condo

39 SYMPHONY DR, BROOKHAVEN, NY, 11755
Want to learn more about 55+ communities in Connecticut? 55places can help!
Questions? Call us: (888) 625-4885
New Regency Meadows 17 REGENCY CIR 17, TRUMBULL, CT, 06611, Trumbull, CT 06611
$765,000

4 beds

|

4 baths

|

2,597 sq ft

|

Condo

17 REGENCY CIR 17, TRUMBULL, CT, 06611
Community: Regency Meadows
New Billingsgate 8 BILLINGSGATE DR, SIMSBURY, CT, 06070, Simsbury, CT 06070
$700,000

2 beds

|

3 baths

|

2,471 sq ft

|

Condo

8 BILLINGSGATE DR, SIMSBURY, CT, 06070
Community: Billingsgate
New Oronoque Village 71 DAKOTA LN A, STRATFORD, CT, 06614, Stratford, CT 06614
$600,000

1 beds

|

2 baths

|

1,375 sq ft

|

Condo

71 DAKOTA LN A, STRATFORD, CT, 06614
Community: Oronoque Village
New Stone Ridge Estates 154 CHRISTINE DR, HUNTINGTON, NY, 11746, Huntington, NY 11746
$760,000

2 beds

|

2 baths

|

1,695 sq ft

|

Condo

154 CHRISTINE DR, HUNTINGTON, NY, 11746
Community: Stone Ridge Estates
New The Summit at Bethel 15 BRIAR RIDGE DR 15, BETHEL, CT, 06801, Bethel, CT 06801
$689,000

2 beds

|

3 baths

|

2,104 sq ft

|

Condo

15 BRIAR RIDGE DR 15, BETHEL, CT, 06801
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 Waterways at Moriches 612 BAY VIEW CIR 12, BROOKHAVEN, NY, 119..., Brookhaven, NY 11955
$799,000

2 beds

|

3 baths

|

1,874 sq ft

|

Condo

612 BAY VIEW CIR 12, BROOKHAVEN, NY, 119...
New Country Pointe Preserve 128 JUNIPER LN 26, BROOKHAVEN, NY, 11980, Brookhaven, NY 11980
$895,000

2 beds

|

3 baths

|

1,998 sq ft

|

Condo

128 JUNIPER LN 26, BROOKHAVEN, NY, 11980
New Leisure Village 167 VENTRY CT D, BROOKHAVEN, NY, 11961, Brookhaven, NY 11961
$259,000

1 beds

|

1 baths

|

684 sq ft

|

Condo

167 VENTRY CT D, BROOKHAVEN, NY, 11961
Community: Leisure Village
New Windcrest East 90 GOLDEN SPRUCE DR, RIVERHEAD, NY, 1193..., Riverhead, NY 11933
$799,000

3 beds

|

3 baths

|

2,620 sq ft

|

House

90 GOLDEN SPRUCE DR, RIVERHEAD, NY, 1193...
Community: Windcrest East
New Fairfield at St. James 111 FAIRFIELD DR 111, SMITHTOWN, NY, 117..., Smithtown, NY 11780
$599,999

2 beds

|

2 baths

|

1,733 sq ft

|

Condo

111 FAIRFIELD DR 111, SMITHTOWN, NY, 117...
New Founders Village 2555 YOUNGS AVE 11A, SOUTHOLD, NY, 11971, Southold, NY 11971
$605,000

2 beds

|

2 baths

|

1,200 sq ft

|

Condo

2555 YOUNGS AVE 11A, SOUTHOLD, NY, 11971
Community: Founders Village
Want to learn more about 55+ communities in Connecticut? 55places can help!
Questions? Call us: (888) 625-4885
New Oronoque Village 476 COMMANCHE LN A, STRATFORD, CT, 06614, Stratford, CT 06614
$565,000

1 beds

|

3 baths

|

1,426 sq ft

|

Condo

476 COMMANCHE LN A, STRATFORD, CT, 06614
Community: Oronoque Village
New Leisure Village 250A NEWCASTLE CT, BROOKHAVEN, NY, 11961, Brookhaven, NY 11961
$359,000

2 beds

|

1 baths

|

1,085 sq ft

|

Condo

250A NEWCASTLE CT, BROOKHAVEN, NY, 11961
Community: Leisure Village
New Leisure Knoll 330 BROWNFIELD DR, BROOKHAVEN, NY, 11961, Brookhaven, NY 11961
$429,000

2 beds

|

1 baths

|

1,020 sq ft

|

Condo

330 BROWNFIELD DR, BROOKHAVEN, NY, 11961
Community: Leisure Knoll
New Leisure Village 190 VENTRY CT F, BROOKHAVEN, NY, 11961, Brookhaven, NY 11961
$269,000

1 beds

|

1 baths

|

684 sq ft

|

Condo

190 VENTRY CT F, 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 Heritage Village 751 HERITAGE VLG B, SOUTHBURY, CT, 06488, Southbury, CT 06488
$215,000

2 beds

|

2 baths

|

1,000 sq ft

|

Condo

751 HERITAGE VLG B, SOUTHBURY, CT, 06488
Community: Heritage Village
New Newtown Woods 1011 BROOKSIDE CT 1011, NEWTOWN, CT, 064..., Newtown, CT 06470
$495,000

2 beds

|

2 baths

|

1,483 sq ft

|

Condo

1011 BROOKSIDE CT 1011, NEWTOWN, CT, 064...
Community: Newtown Woods
New Leisure Glen 7 SAGAPONACK CT, BROOKHAVEN, NY, 11961, Brookhaven, NY 11961
$599,000

2 beds

|

2 baths

|

1,867 sq ft

|

Condo

7 SAGAPONACK CT, BROOKHAVEN, NY, 11961
Community: Leisure Glen
New The Seasons at East Northport 157 AUGUST CIR, HUNTINGTON, NY, 11731, Huntington, NY 11731
$998,000

2 beds

|

3 baths

|

2,516 sq ft

|

Condo

157 AUGUST CIR, HUNTINGTON, NY, 11731
Regency at Prospect 112 CHERRY CIR 112, PROSPECT, CT, 06712, Prospect, CT 06712
$338,903

3 beds

|

2 baths

|

1,500 sq ft

|

Condo

112 CHERRY CIR 112, PROSPECT, CT, 06712
Community: Regency at Prospect
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
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...
Want to learn more about 55+ communities in Connecticut? 55places can help!
Questions? Call us: (888) 625-4885
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
The Summit at Bethel 14 GREAT HILL DR 14, BETHEL, CT, 06801, Bethel, CT 06801
$699,000

3 beds

|

3 baths

|

2,744 sq ft

|

Condo

14 GREAT HILL DR 14, BETHEL, CT, 06801
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
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 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...
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
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
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
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

|

2,008 sq ft

|

Condo

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
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...
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 19, 2026.
This application does not include information on all of the properties available for sale at this time.

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