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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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Strathmore Gate East
$300ks
Strathmore Gate East, Coram, NY
Resale Only | 55+ age-restricted | Built 1970 - 1975 | 174 homes
5 rating (3 reviews) Founders Ridge
$300ks - $400ks
Founders Ridge, Middletown, CT
New Construction | 55+ age-restricted | Built 2017 - present | 75 homes
Country Village Estates
$300ks
Country Village Estates, Coram, NY
Resale Only | 55+ age-restricted | Built 1993 - 2001 | 195 homes
Billingsgate
$400ks - $600ks
Billingsgate, Simsbury, CT
Resale Only | 55+ age-restricted | Built 2003 - 2006 | 37 homes
Founders Village
$400ks - $500ks
Founders Village, Southold, NY
Resale Only | 55+ age-restricted | Built 1981 - 1985 | 92 homes
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The Vineyards at Miller P...
$500ks
The Vineyards at Miller P..., Miller Place, NY
Resale Only | 55+ age-restricted | Built 2004 - 2005 | 85 homes
Hopmeadow Place
$200ks - $300ks
Hopmeadow Place, Simsbury, CT
Resale Only | 55+ age-restricted | Built 2005 - 2005 | 66 homes
Stone Ridge Estates
$500ks - $600ks
Stone Ridge Estates, Dix Hills, NY
Resale Only | 55+ age-restricted | Built 2004 - 2013 | 76 homes
Park Glen
$300ks - $500ks
Park Glen, New Milford, CT
Resale Only | 55+ age-restricted | Built 2006 - 2015 | 17 homes
Kensington Estates
$1Ms
Kensington Estates, Woodbury, NY
New Construction | 55+ age-restricted | Built 2019 - 2021 | 80 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.
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 Seasons at Elwood
$800ks - $900ks
The Seasons at Elwood, East Northport, NY
Resale Only | 55+ age-restricted | Built 2018 - 2020 | 256 homes
Regency Meadows
$500ks
Regency Meadows, Trumbull, CT
Resale Only | 55+ age-restricted | Built 2003 - 2005 | 51 homes
Bidwell Village
$300ks - $400ks
Bidwell Village, Coventry, CT
New Construction | 55+ age-restricted | Built 2020 - present | 37 homes
South Pond Village
$300ks - $400ks
South Pond Village, Bloomfield, CT
Resale Only | 55+ age-restricted | Built 1999 - 2005 | 151 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
Vineyards at Moriches
$500ks - $600ks
Vineyards at Moriches, Center Moriches, NY
Resale Only | 55+ age-restricted | Built 2008 - 2014 | 92 homes
Granite Woods
$600ks - $700ks
Granite Woods, Middlebury, CT
New Construction | 55+ age-restricted | Built 2020 - present | 24 homes
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
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.
Saddle Lakes
$400ks - $500ks
Saddle Lakes, Riverhead, NY
Resale Only | 55+ age-restricted | Built 2000 - 2002 | 196 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
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
Want to learn more about 55+ communities in Connecticut? 55places can help!
Questions? Call us: (888) 625-4885
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
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
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
Newbury Village
$400ks - $500ks
Newbury Village, Brookfield, CT
New and Resale | 55+ age-restricted | Built 2005 - present | 120 homes
Clockmaker's Hill
$100ks
Clockmaker's Hill, Winsted, CT
Resale Only | 55+ age-restricted | Built 2005 - 2014 | 38 homes
Bartlett Hill
$300ks - $400ks
Bartlett Hill, Portland, CT
Resale Only | 55+ age-restricted | Built 2005 - 2011 | 82 homes
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
Want to learn more about 55+ communities in Connecticut? 55places can help!
Questions? Call us: (888) 625-4885
North Woods of Colchester
$300ks - $400ks
North Woods of Colchester, Colchester, CT
New and Resale | 55+ age-restricted | Built 2007 - present | 140 homes
Chimney Hill
$500ks - $700ks
Chimney Hill, Farmington, CT
Resale Only | 55+ age-restricted | Built 2006 - 2013 | 44 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
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 226A S DURKEE HILL RD 226A, SOUTHBURY, C..., Southbury, CT 06488
$338,500

2 beds

|

2 baths

|

1,398 sq ft

|

Condo

226A S DURKEE HILL RD 226A, SOUTHBURY, C...
Community: Heritage Village
New Greenwood Village 124 VILLAGE CIR 124, BROOKHAVEN, NY, 119..., Brookhaven, NY 11949
$179,997

2 beds

|

2 baths

|

116 sq ft

|

Condo

124 VILLAGE CIR 124, BROOKHAVEN, NY, 119...
Community: Greenwood Village
New The Seasons at East Northport 40 AUGUST CIR 40, HUNTINGTON, NY, 11731, Huntington, NY 11731
$772,150

2 beds

|

2 baths

|

1,536 sq ft

|

Condo

40 AUGUST CIR 40, HUNTINGTON, NY, 11731
Want to learn more about 55+ communities in Connecticut? 55places can help!
Questions? Call us: (888) 625-4885
New Plymouth Estates at Mount Sinai 55 ROSE LN, BROOKHAVEN, NY, 11766, Brookhaven, NY 11766
$548,888

2 beds

|

2 baths

|

1,272 sq ft

|

Condo

55 ROSE LN, BROOKHAVEN, NY, 11766
New Fairfield at St. James 1102 GOTHAM PATH, SMITHTOWN, NY, 11780, Smithtown, NY 11780
$639,900

3 beds

|

3 baths

|

1,601 sq ft

|

Condo

1102 GOTHAM PATH, SMITHTOWN, NY, 11780
New Leisure Knoll 257 EDINBURGH DR, BROOKHAVEN, NY, 11961, Brookhaven, NY 11961
$539,900

2 beds

|

2 baths

|

1,000 sq ft

|

Condo

257 EDINBURGH DR, BROOKHAVEN, NY, 11961
Community: Leisure Knoll
New Beckley Farms 91 SCENIC DR 91, BERLIN, CT, 06037, Berlin, CT 06037
$679,900

3 beds

|

3 baths

|

2,068 sq ft

|

Condo

91 SCENIC DR 91, BERLIN, CT, 06037
Community: Beckley Farms
New Foxwood Village 1407 MIDDLE RD 45, RIVERHEAD, NY, 11933, Riverhead, NY 11933
$315,000

2 beds

|

2 baths

|

1,100 sq ft

|

House

1407 MIDDLE RD 45, RIVERHEAD, NY, 11933
Community: Foxwood 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 162 HERITAGE VLG D, SOUTHBURY, CT, 06488, Southbury, CT 06488
$249,000

2 beds

|

2 baths

|

1,076 sq ft

|

Condo

162 HERITAGE VLG D, SOUTHBURY, CT, 06488
Community: Heritage Village
New Woodridge Strathmore Terrace 55 STANDISH DR, BROOKHAVEN, NY, 11766, Brookhaven, NY 11766
$499,000

2 beds

|

2 baths

|

1,501 sq ft

|

House

55 STANDISH DR, BROOKHAVEN, NY, 11766
New Greenwood Village 33A LIMETREE DR, BROOKHAVEN, NY, 11949, Brookhaven, NY 11949
$99,999

1 beds

|

1 baths

|

460 sq ft

|

Condo

33A LIMETREE DR, BROOKHAVEN, NY, 11949
Community: Greenwood Village
New Country Pointe Plainview 52102 BEECH TREE LN, OYSTER BAY, NY, 118..., Oyster Bay, NY 11803
$1,664,990

3 beds

|

3 baths

|

1,730 sq ft

|

Condo

52102 BEECH TREE LN, OYSTER BAY, NY, 118...
New Heritage Village 397 KRUEGER CIR A, SOUTHBURY, CT, 06488, Southbury, CT 06488
$439,700

3 beds

|

2 baths

|

1,716 sq ft

|

Condo

397 KRUEGER CIR A, SOUTHBURY, CT, 06488
Community: Heritage Village
New The Village at Oxford Greens 1073 AUGUSTA DR 1073, OXFORD, CT, 06478, Oxford, CT 06478
$629,900

2 beds

|

3 baths

|

2,232 sq ft

|

Condo

1073 AUGUSTA DR 1073, OXFORD, CT, 06478
Want to learn more about 55+ communities in Connecticut? 55places can help!
Questions? Call us: (888) 625-4885
New Fairview at Oxford Greens 1073 AUGUSTA DR 1073, OXFORD, CT, 06478, Oxford, CT 06478
$629,900

2 beds

|

3 baths

|

2,232 sq ft

|

Condo

1073 AUGUSTA DR 1073, OXFORD, CT, 06478
New Oronoque Village 55 BLACK HAWK LN B, STRATFORD, CT, 06614, Stratford, CT 06614
$639,000

2 beds

|

3 baths

|

1,360 sq ft

|

Condo

55 BLACK HAWK LN B, STRATFORD, CT, 06614
Community: Oronoque Village
New Meadowbrook Pointe Links & Spa 38 AUGUSTA DR, BROOKHAVEN, NY, 11763, Brookhaven, NY 11763
$400,697

2 beds

|

3 baths

|

1,440 sq ft

|

Condo

38 AUGUSTA DR, BROOKHAVEN, NY, 11763
New Oronoque Village 209 ACORN LN B, STRATFORD, CT, 06614, Stratford, CT 06614
$554,000

2 beds

|

3 baths

|

1,438 sq ft

|

Condo

209 ACORN LN B, 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.
New Spring Lake Village 764 KETTLE PATH 764, SOUTHINGTON, CT, 06..., Southington, CT 06489
$355,000

2 beds

|

2 baths

|

1,445 sq ft

|

Condo

764 KETTLE PATH 764, SOUTHINGTON, CT, 06...
Community: Spring Lake Village
New Heritage Village 633 HERITAGE VLG A, SOUTHBURY, CT, 06488, Southbury, CT 06488
$400,000

2 beds

|

2 baths

|

1,432 sq ft

|

Condo

633 HERITAGE VLG A, SOUTHBURY, CT, 06488
Community: Heritage Village
New Heritage Village 626 HERITAGE VLG B, SOUTHBURY, CT, 06488, Southbury, CT 06488
$300,000

2 beds

|

2 baths

|

1,432 sq ft

|

Condo

626 HERITAGE VLG B, SOUTHBURY, CT, 06488
Community: Heritage Village
The Seasons at Plainview 53 AUTUMN DR, OYSTER BAY, NY, 11803, Oyster Bay, NY 11803
$829,000

2 beds

|

2 baths

|

1,379 sq ft

|

Condo

53 AUTUMN DR, OYSTER BAY, NY, 11803
The Village at Buckingham 3 CAVENDISH PL 3, AVON, CT, 06001, Avon, CT 06001
$689,000

3 beds

|

3 baths

|

2,730 sq ft

3 CAVENDISH PL 3, AVON, CT, 06001
Fairfield at St. James 705 ALDEN CT, SMITHTOWN, NY, 11780, Smithtown, NY 11780
$559,803

2 beds

|

2 baths

|

954 sq ft

|

Condo

705 ALDEN CT, SMITHTOWN, NY, 11780
Rivington 11 MERCY ST 11, DANBURY, CT, 06810, Danbury, CT 06810
$600,000

2 beds

|

4 baths

|

1,572 sq ft

|

Condo

11 MERCY ST 11, DANBURY, CT, 06810
Community: Rivington
Want to learn more about 55+ communities in Connecticut? 55places can help!
Questions? Call us: (888) 625-4885
Heritage Village 149 HERITAGE VLG A, SOUTHBURY, CT, 06488, Southbury, CT 06488
$198,000

1 beds

|

1 baths

|

928 sq ft

|

Condo

149 HERITAGE VLG A, SOUTHBURY, CT, 06488
Community: Heritage Village
Bidwell Village 94 STONEHOUSE RD 13, COVENTRY, CT, 06238, Coventry, CT 06238
$385,000

3 beds

|

4 baths

|

1,810 sq ft

|

Condo

94 STONEHOUSE RD 13, COVENTRY, CT, 06238
Community: Bidwell Village
The Greens at Half Hollow 119 MADEIRA BLVD, HUNTINGTON, NY, 11747, Huntington, NY 11747
$1,525,000

3 beds

|

3 baths

|

2,700 sq ft

|

Condo

119 MADEIRA BLVD, 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.
Sunken Pond Estates 3704 AMEN COR, RIVERHEAD, NY, 11901, Riverhead, NY 11901
$529,000

2 beds

|

3 baths

|

1,350 sq ft

|

Condo

3704 AMEN COR, RIVERHEAD, NY, 11901
Community: Sunken Pond Estates
Leisure Village 395 WOODBRIDGE DR E, BROOKHAVEN, NY, 119..., Brookhaven, NY 11961
$322,900

2 beds

|

1 baths

|

875 sq ft

|

Condo

395 WOODBRIDGE DR E, BROOKHAVEN, NY, 119...
Community: Leisure Village
Plymouth Estates at Mount Sinai 240 IRA RD, BROOKHAVEN, NY, 11766, Brookhaven, NY 11766
$599,999

2 beds

|

2 baths

|

1,396 sq ft

|

Condo

240 IRA RD, BROOKHAVEN, NY, 11766
Windcrest East 29 GOLDEN SPRUCE DR, RIVERHEAD, NY, 1193..., Riverhead, NY 11933
$825,000

3 beds

|

3 baths

|

2,531 sq ft

|

House

29 GOLDEN SPRUCE DR, RIVERHEAD, NY, 1193...
Community: Windcrest East
Leisure Knoll 473 STRATFORD LN, BROOKHAVEN, NY, 11961, Brookhaven, NY 11961
$539,000

2 beds

|

2 baths

|

1,350 sq ft

|

House

473 STRATFORD LN, BROOKHAVEN, NY, 11961
Community: Leisure Knoll
Heritage Village 13 HERITAGE VLG B, SOUTHBURY, CT, 06488, Southbury, CT 06488
$223,000

2 beds

|

2 baths

|

1,032 sq ft

|

Condo

13 HERITAGE VLG B, SOUTHBURY, CT, 06488
Community: Heritage Village
Sonoma Woods 35 SONOMA LN 35, MIDDLETOWN, CT, 06457, Middletown, CT 06457
$589,000

2 beds

|

3 baths

|

1,798 sq ft

|

Condo

35 SONOMA LN 35, MIDDLETOWN, CT, 06457
Community: Sonoma Woods
Heritage Village 955 HERITAGE VLG B, SOUTHBURY, CT, 06488, Southbury, CT 06488
$269,900

2 beds

|

2 baths

|

1,398 sq ft

|

Condo

955 HERITAGE VLG B, SOUTHBURY, CT, 06488
Community: Heritage Village
Want to learn more about 55+ communities in Connecticut? 55places can help!
Questions? Call us: (888) 625-4885
The Village at Oxford Greens 155 COUNTRY CLUB DR 155, OXFORD, CT, 064..., Oxford, CT 06478
$659,000

3 beds

|

3 baths

|

2,008 sq ft

|

Condo

155 COUNTRY CLUB DR 155, OXFORD, CT, 064...
Spring Lake Village 28 COACH DR 28, SOUTHINGTON, CT, 06489, Southington, CT 06489
$230,000

2 beds

|

1 baths

|

985 sq ft

|

Condo

28 COACH DR 28, SOUTHINGTON, CT, 06489
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.



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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 29, 2026.
This application does not include information on all of the properties available for sale at this time.

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