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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


62 communities near Connecticut

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Long Hill Village
$300ks - $400ks
Long Hill Village, Trumbull, CT
Resale Only | 55+ age-restricted | Built 1997 - 1999 | 71 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
Cobblestone Court
$400ks - $500ks
Cobblestone Court, Essex, CT
New and Resale | 55+ age-restricted | Built 2017 - present | 8 homes
Want to learn more about 55+ communities in Connecticut? 55places can help!
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The Coach Homes at Ridgef...
$300ks - $400ks
The Coach Homes at Ridgef..., Ridgefield, CT
New Construction | 55+ age-restricted | Built 2019 - present | 30 homes
Whitney Glen
$500ks - $600ks
Whitney Glen, Westport, CT
Resale Only | 55+ age-restricted | Built 1982 - 1982 | 62 homes
Regency at Woodbridge
$500ks - $700ks
Regency at Woodbridge, Woodbridge, CT
New Construction | 55+ age-restricted | Built 2023 - present | 70 homes
The Bridges at Oxford Gre...
$600ks
The Bridges at Oxford Gre..., Oxford, CT
New Construction | 55+ age-restricted | Built 2025 - present | 99 homes
Rivington Landing
$500ks
Rivington Landing, Danbury, CT
New Construction | Age-targeted | Built 2025 - 2026 | 25 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.
Granite Woods
$600ks - $700ks
Granite Woods, Middlebury, CT
New Construction | 55+ age-restricted | Built 2020 - present | 24 homes
Founders Village
$400ks - $500ks
Founders Village, Southold, NY
Resale Only | 55+ age-restricted | Built 1981 - 1985 | 92 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
Want to learn more about 55+ communities in Connecticut? 55places can help!
Questions? Call us: (888) 625-4885
Sonoma Woods
$300ks
Sonoma Woods, Middletown, CT
Resale Only | 55+ age-restricted | Built 2005 - 2015 | 68 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
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.
Newington Ridge Preserve
$300ks - $400ks
Newington Ridge Preserve, Newington, CT
New Construction | 55+ age-restricted | Built 2014 - present | 16 homes
5 rating (3 reviews) Founders Ridge
$300ks - $400ks
Founders Ridge, Middletown, CT
New Construction | 55+ age-restricted | Built 2017 - present | 75 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
New Heritage Village 804 HERITAGE VLG B, SOUTHBURY, CT, 06488, Southbury, CT 06488
$259,000

2 beds

|

2 baths

|

1,432 sq ft

|

Condo

804 HERITAGE VLG B, SOUTHBURY, CT, 06488
Community: Heritage Village
New Oronoque Village 89 S TRL A, STRATFORD, CT, 06614, Stratford, CT 06614
$649,000

1 beds

|

3 baths

|

1,438 sq ft

|

Condo

89 S TRL A, STRATFORD, CT, 06614
Community: Oronoque Village
New Oak Meadow Estates 197 OAK MEADOW LN 197, TORRINGTON, CT, 0..., Torrington, CT 06790
$399,000

2 beds

|

2 baths

|

1,419 sq ft

|

Condo

197 OAK MEADOW LN 197, TORRINGTON, CT, 0...
Community: Oak Meadow Estates
New Heritage Village 301 HERRITAGE VLG B, SOUTHBURY, CT, 0648..., Southbury, CT 06488
$235,000

2 beds

|

2 baths

|

1,365 sq ft

|

Condo

301 HERRITAGE VLG B, SOUTHBURY, CT, 0648...
Community: Heritage Village
New Billingsgate 14 BILLINGSGATE DR 14, SIMSBURY, CT, 060..., Simsbury, CT 06070
$750,000

2 beds

|

3 baths

|

2,729 sq ft

|

Condo

14 BILLINGSGATE DR 14, SIMSBURY, CT, 060...
Community: Billingsgate
Want to learn more about 55+ communities in Connecticut? 55places can help!
Questions? Call us: (888) 625-4885
New Heritage Village 184 HERITAGE VLG A, SOUTHBURY, CT, 06488, Southbury, CT 06488
$209,000

1 beds

|

1 baths

|

928 sq ft

|

Condo

184 HERITAGE VLG A, SOUTHBURY, CT, 06488
Community: Heritage Village
New The Powder Forest Homes 6 PROSPECT RDG 6, SIMSBURY, CT, 06070, Simsbury, CT 06070
$715,000

3 beds

|

3 baths

|

2,183 sq ft

6 PROSPECT RDG 6, SIMSBURY, CT, 06070
New Heritage Village 333 HERITAGE VLG B, SOUTHBURY, CT, 06488, Southbury, CT 06488
$335,000

2 beds

|

2 baths

|

1,432 sq ft

|

Condo

333 HERITAGE VLG B, SOUTHBURY, CT, 06488
Community: Heritage Village
New The Village at Oxford Greens 443 TEE SHOT DR 443, OXFORD, CT, 06478, Oxford, CT 06478
$689,900

3 beds

|

3 baths

|

2,759 sq ft

|

Condo

443 TEE SHOT DR 443, OXFORD, CT, 06478
New Hopmeadow Place 1 W ST 310, SIMSBURY, CT, 06070, Simsbury, CT 06070
$385,000

2 beds

|

2 baths

|

1,430 sq ft

|

Condo

1 W ST 310, SIMSBURY, CT, 06070
Community: Hopmeadow Place
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.
Oronoque Village 448 HAMMERSTONE LN B, STRATFORD, CT, 066..., Stratford, CT 06614
$525,000

1 beds

|

3 baths

|

1,438 sq ft

|

Condo

448 HAMMERSTONE LN B, STRATFORD, CT, 066...
Community: Oronoque Village
The Powder Forest Homes 6 RONAN WAY 6, SIMSBURY, CT, 06070, Simsbury, CT 06070
$739,900

2 beds

|

3 baths

|

1,864 sq ft

6 RONAN WAY 6, SIMSBURY, CT, 06070
Spring Lake Village 402 LAKEVIEW DR 402, SOUTHINGTON, CT, 06..., Southington, CT 06489
$324,900

2 beds

|

2 baths

|

1,188 sq ft

|

Condo

402 LAKEVIEW DR 402, SOUTHINGTON, CT, 06...
Community: Spring Lake Village
Newtown Woods 832 BROOKSIDE CT 832, NEWTOWN, CT, 06470, Newtown, CT 06470
$585,000

2 beds

|

2 baths

|

1,807 sq ft

|

Condo

832 BROOKSIDE CT 832, NEWTOWN, CT, 06470
Community: Newtown Woods
Heritage Village 945 HERITAGE VLG A, SOUTHBURY, CT, 06488, Southbury, CT 06488
$414,900

2 beds

|

2 baths

|

1,432 sq ft

|

Condo

945 HERITAGE VLG A, SOUTHBURY, CT, 06488
Community: Heritage Village
Heritage Village 339 HERITAGE VLG A, SOUTHBURY, CT, 06488, Southbury, CT 06488
$335,000

2 beds

|

2 baths

|

1,398 sq ft

|

Condo

339 HERITAGE VLG 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
Rivington 82 WINDING RIDGE WAY 82, DANBURY, CT, 06..., Danbury, CT 06810
$925,000

3 beds

|

4 baths

|

2,388 sq ft

|

Condo

82 WINDING RIDGE WAY 82, DANBURY, CT, 06...
Community: Rivington
The Village at Oxford Greens 567 INVERNESS CT 567, OXFORD, CT, 06478, Oxford, CT 06478
$665,000

2 beds

|

2 baths

|

2,008 sq ft

567 INVERNESS CT 567, OXFORD, CT, 06478
The Powder Forest Homes 15 BANTRY RD 15, SIMSBURY, CT, 06070, Simsbury, CT 06070
$949,000

4 beds

|

3 baths

|

1,878 sq ft

15 BANTRY RD 15, SIMSBURY, CT, 06070
Oronoque Village 283 AGAWAM DR A, STRATFORD, CT, 06614, Stratford, CT 06614
$625,000

2 beds

|

3 baths

|

1,415 sq ft

|

Condo

283 AGAWAM DR 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.
Meadow Brook Estates 211 MEADOW BROOK RD 211, OXFORD, CT, 064..., Oxford, CT 06478
$625,000

3 beds

|

3 baths

|

2,201 sq ft

|

Condo

211 MEADOW BROOK RD 211, OXFORD, CT, 064...
Heritage Village 10 HERITAGE CIR A, SOUTHBURY, CT, 06488, Southbury, CT 06488
$364,000

3 beds

|

2 baths

|

1,716 sq ft

|

Condo

10 HERITAGE CIR A, SOUTHBURY, CT, 06488
Community: Heritage Village
Rivington 104 CENTER MEADOW LN 104, DANBURY, CT, 0..., Danbury, CT 06810
$510,000

2 beds

|

2 baths

|

1,330 sq ft

|

Condo

104 CENTER MEADOW LN 104, DANBURY, CT, 0...
Community: Rivington
Spring Lake Village 342 SONGBIRD LN 342, SOUTHINGTON, CT, 06..., Southington, CT 06489
$259,900

2 beds

|

1 baths

|

912 sq ft

|

Condo

342 SONGBIRD LN 342, SOUTHINGTON, CT, 06...
Community: Spring Lake Village
Liberty at Newtown 49 JO AL CT 49, NEWTOWN, CT, 06470, Newtown, CT 06470
$635,000

2 beds

|

3 baths

|

2,341 sq ft

|

Condo

49 JO AL CT 49, NEWTOWN, CT, 06470
Community: Liberty at Newtown
Heritage Village 1 HERITAGE VLG C, SOUTHBURY, CT, 06488, Southbury, CT 06488
$248,000

2 beds

|

2 baths

|

1,044 sq ft

|

Condo

1 HERITAGE VLG C, SOUTHBURY, CT, 06488
Community: Heritage Village
Heritage Village 24 HERITAGE VLG A, SOUTHBURY, CT, 06488, Southbury, CT 06488
$237,000

2 beds

|

2 baths

|

1,076 sq ft

|

Condo

24 HERITAGE VLG 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 59 HERITAGE VLG B, SOUTHBURY, CT, 06488, Southbury, CT 06488
$249,000

2 beds

|

2 baths

|

1,076 sq ft

|

Condo

59 HERITAGE VLG B, SOUTHBURY, CT, 06488
Community: Heritage Village
Oronoque Village 93 SEMINOLE LN B, STRATFORD, CT, 06614, Stratford, CT 06614
$559,000

2 beds

|

3 baths

|

2,542 sq ft

|

Condo

93 SEMINOLE LN B, STRATFORD, CT, 06614
Community: Oronoque Village
Heritage Village 196 HERITAGE VLG E, SOUTHBURY, CT, 06488, Southbury, CT 06488
$229,900

2 beds

|

2 baths

|

1,044 sq ft

|

Condo

196 HERITAGE VLG E, 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.
Newbury Village 46 GREAT HERON LN 46, BROOKFIELD, CT, 06..., Brookfield, CT 06804
$699,000

2 beds

|

4 baths

|

2,560 sq ft

|

Condo

46 GREAT HERON LN 46, BROOKFIELD, CT, 06...
Community: Newbury Village
Liberty at Newtown 25 FRANKLIN CT 25, NEWTOWN, CT, 06470, Newtown, CT 06470
$545,000

2 beds

|

2 baths

|

1,413 sq ft

|

Condo

25 FRANKLIN CT 25, NEWTOWN, CT, 06470
Community: Liberty at Newtown
Regency at Prospect 6 LILAC LN 6, PROSPECT, CT, 06712, Prospect, CT 06712
$474,900

2 beds

|

3 baths

|

1,552 sq ft

|

Condo

6 LILAC LN 6, PROSPECT, CT, 06712
Community: Regency at Prospect
Rivington 11 ORWICH CT 11, DANBURY, CT, 06810, Danbury, CT 06810
$649,900

3 beds

|

4 baths

|

1,572 sq ft

|

Condo

11 ORWICH CT 11, DANBURY, CT, 06810
Community: Rivington
Heritage Village 912 HERITAGE VLG B, SOUTHBURY, CT, 06488, Southbury, CT 06488
$359,000

3 beds

|

2 baths

|

1,716 sq ft

|

Condo

912 HERITAGE VLG B, SOUTHBURY, CT, 06488
Community: Heritage Village
The Village at Oxford Greens 527 PUTTING GREEN LN 527, OXFORD, CT, 06..., Oxford, CT 06478
$699,000

3 beds

|

3 baths

|

2,008 sq ft

|

Condo

527 PUTTING GREEN LN 527, OXFORD, CT, 06...
Regency at Prospect 10 ASH LN 10, PROSPECT, CT, 06712, Prospect, CT 06712
$539,000

2 beds

|

3 baths

|

1,928 sq ft

|

Condo

10 ASH LN 10, PROSPECT, CT, 06712
Community: Regency at Prospect
Newtown Woods 1011 BROOKSIDE CT 1011, NEWTOWN, CT, 064..., Newtown, CT 06470
$500,000

2 beds

|

2 baths

|

1,483 sq ft

|

Condo

1011 BROOKSIDE CT 1011, NEWTOWN, CT, 064...
Community: Newtown Woods
Want to learn more about 55+ communities in Connecticut? 55places can help!
Questions? Call us: (888) 625-4885
Heritage Village 18 HERITAGE CRST D, SOUTHBURY, CT, 06488, Southbury, CT 06488
$434,981

3 beds

|

2 baths

|

1,735 sq ft

|

Condo

18 HERITAGE CRST D, SOUTHBURY, CT, 06488
Community: Heritage Village
Fairview at Oxford Greens 1131 ST ANDREWS DR 50, OXFORD, CT, 06478, Oxford, CT 06478
$713,775

2 beds

|

3 baths

|

2,536 sq ft

|

Condo

1131 ST ANDREWS DR 50, OXFORD, CT, 06478
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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© 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: Jun 27, 2026.
This application does not include information on all of the properties available for sale at this time.

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