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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 convenient regional access. Fairfield County and the New Haven shoreline sit closest to New York City,…

Connecticut offers a classic New England retirement lifestyle coupled with convenient regional access. Fairfield County and the New Haven shoreline sit closest to New York City, while Hartford-area towns are within driving distance of Boston. The scenic Long Island Sound shoreline runs the length of the state, and the Litchfield Hills provide a peaceful, rural alternative.

 Yale New Haven Health and Hartford HealthCare are two of the state's largest health systems. The state's four distinct seasons include New England's famous autumn foliage. Winters and home prices are real factors, so many buyers weigh staying close to family against a move to a warmer market.

Among Connecticut's senior housing and senior living options, 55 and over communities are designed for active adults who live independently. Connecticut is home to more than 60 active adult communities, with properties ranging from the mid-$100Ks to over $1M and averaging around $550K. Heritage Village in Southbury (2,580 homes) is the state's largest 55+ community.

Active adults seeking mid-sized options gravitate toward Oronoque Village in Stratford (929 homes) and Spring Lake Village in Southington (640 homes). Those prioritizing modern layouts favor new-construction neighborhoods like Chatfield Farms in Beacon Falls and The Village at Oxford Greens in Oxford.

55places has profiled every local development with verified pricing tiers, resident reviews, and direct local agent connections.

Quick Facts About Retiring in Connecticut


106 communities near Connecticut

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Setauket Meadows
$500ks - $600ks
Setauket Meadows, Setauket, NY
Resale Only | 55+ age-restricted | Built 2005 - 2007 | 150 homes
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
Want to learn more about 55+ communities in Connecticut? 55places can help!
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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
Kensington Estates
$1Ms
Kensington Estates, Woodbury, NY
New Construction | 55+ age-restricted | Built 2019 - 2021 | 80 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
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
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.
Stoneleigh Woods at River...
$500ks
Stoneleigh Woods at River..., Riverhead, NY
Resale Only | 55+ age-restricted | Built 2007 - 2016 | 176 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
Vineyards at Moriches
$500ks - $600ks
Vineyards at Moriches, Center Moriches, NY
Resale Only | 55+ age-restricted | Built 2008 - 2014 | 92 homes
Country Pointe Preserve
$600ks - $900ks
Country Pointe Preserve, Yaphank, NY
New Construction | 55+ age-restricted | Built 2024 - present | 152 homes
Evergreen
$400ks - $500ks
Evergreen, Cromwell, CT
New and Resale | 55+ age-restricted | Built 2005 - present | 52 homes
Want to learn more about 55+ communities in Connecticut? 55places can help!
Questions? Call us: (888) 625-4885
The Cottages at Wire Mill
$1Ms
The Cottages at Wire Mill, Stamford, CT
New Construction | 55+ age-restricted | Built 2026 - present | 9 homes
5 rating (2 reviews) Benson Woods
$400ks - $600ks
Benson Woods, Middlebury, CT
New and Resale | 55+ age-restricted | Built 2004 - present | 79 homes
The Summit at Bethel
$500ks - $700ks
The Summit at Bethel, Bethel, CT
Resale Only | 55+ age-restricted | Built 2010 - 2021 | 235 homes
The Bridges at Oxford Gre...
$600ks
The Bridges at Oxford Gre..., Oxford, CT
New Construction | 55+ age-restricted | Built 2025 - present | 99 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.
O'Meara Farm
$400ks
O'Meara Farm, Farmington, CT
Resale Only | 55+ age-restricted | Built 1998 - 2005 | 104 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 review) The Villages at Mount Sin...
$600ks
The Villages at Mount Sin..., Mount Sinai, NY
Resale Only | 55+ age-restricted | Built 2005 - 2007 | 185 homes
Founders Village
$400ks - $500ks
Founders Village, Southold, NY
Resale Only | 55+ age-restricted | Built 1981 - 1985 | 92 homes
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
Want to learn more about 55+ communities in Connecticut? 55places can help!
Questions? Call us: (888) 625-4885
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
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
Applegate Estates
$500ks - $400ks
Applegate Estates, Southington, CT
New and Resale | 55+ age-restricted | Built 2010 - 2025 | 94 homes
Rivington Landing
$500ks
Rivington Landing, Danbury, CT
New Construction | Age-targeted | Built 2025 - 2026 | 25 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
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
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.
New Greenwood Village 5147 VILLAGE CIR, BROOKHAVEN, NY, 11949, Brookhaven, NY 11949
$247,500

2 beds

|

2 baths

|

1,592 sq ft

|

Condo

5147 VILLAGE CIR, BROOKHAVEN, NY, 11949
Community: Greenwood Village
Leisure Village 177 VENTRY CT A, BROOKHAVEN, NY, 11961, Brookhaven, NY 11961
$449,500

2 beds

|

1 baths

|

1,085 sq ft

|

Condo

177 VENTRY CT A, BROOKHAVEN, NY, 11961
Community: Leisure Village
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
New Whitney Glen 39 WHITNEY GLN 39, WESTPORT, CT, 06880, Westport, CT 06880
$925,000

2 beds

|

2 baths

|

1,600 sq ft

|

Condo

39 WHITNEY GLN 39, WESTPORT, CT, 06880
Community: Whitney Glen
New The Vineyards at Miller Place 6 HALLEY LN, BROOKHAVEN, NY, 11764, Brookhaven, NY 11764
$559,000

2 beds

|

2 baths

|

1,291 sq ft

|

House

6 HALLEY LN, BROOKHAVEN, NY, 11764
Want to learn more about 55+ communities in Connecticut? 55places can help!
Questions? Call us: (888) 625-4885
New Heritage Village 809 HERITAGE VLG B, SOUTHBURY, CT, 06488, Southbury, CT 06488
$329,900

2 beds

|

2 baths

|

1,432 sq ft

|

Condo

809 HERITAGE VLG B, SOUTHBURY, CT, 06488
Community: Heritage Village
New The Greens at Half Hollow 1149 SAVOY DR, HUNTINGTON, NY, 11747, Huntington, NY 11747
$678,888

2 beds

|

2 baths

|

1,150 sq ft

|

Condo

1149 SAVOY DR, HUNTINGTON, NY, 11747
New Sonoma Woods 2 SONOMA LN 2, MIDDLETOWN, CT, 06457, Middletown, CT 06457
$549,900

2 beds

|

3 baths

|

1,903 sq ft

2 SONOMA LN 2, MIDDLETOWN, CT, 06457
Community: Sonoma Woods
New Leisure Knoll 434 KINGSTON DR 434, BROOKHAVEN, NY, 119..., Brookhaven, NY 11961
$499,000

2 beds

|

2 baths

|

1,646 sq ft

|

Condo

434 KINGSTON DR 434, BROOKHAVEN, NY, 119...
Community: Leisure Knoll
New The Villages at Mount Sinai Park 93 LOUDEN LOOP, BROOKHAVEN, NY, 11766, Brookhaven, NY 11766
$799,000

2 beds

|

2 baths

|

2,234 sq ft

|

House

93 LOUDEN LOOP, BROOKHAVEN, NY, 11766
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.
Leisure Glen 277 GLEN DR, BROOKHAVEN, NY, 11961, Brookhaven, NY 11961
$535,900

2 beds

|

2 baths

|

1,542 sq ft

|

Condo

277 GLEN DR, BROOKHAVEN, NY, 11961
Community: Leisure Glen
Heritage Village 45 HERITAGE VLG A, SOUTHBURY, CT, 06488, Southbury, CT 06488
$289,900

2 beds

|

2 baths

|

1,032 sq ft

|

Condo

45 HERITAGE VLG A, SOUTHBURY, CT, 06488
Community: Heritage Village
Heritage Village 198 HERITAGE VLG B, SOUTHBURY, CT, 06488, Southbury, CT 06488
$325,000

2 beds

|

2 baths

|

1,432 sq ft

|

Condo

198 HERITAGE VLG B, SOUTHBURY, CT, 06488
Community: Heritage Village
Meadowbrook Pointe Links & Spa 146 AUGUSTA DR, BROOKHAVEN, NY, 11763, Brookhaven, NY 11763
$800,000

2 beds

|

3 baths

|

2,047 sq ft

|

Condo

146 AUGUSTA DR, BROOKHAVEN, NY, 11763
Strathmore Gate East 46 FORGE LN, BROOKHAVEN, NY, 11727, Brookhaven, NY 11727
$429,999

2 beds

|

2 baths

|

1,112 sq ft

|

Condo

46 FORGE LN, BROOKHAVEN, NY, 11727
Greenwood Village 40 GREENWOOD BLVD, BROOKHAVEN, NY, 11949, Brookhaven, NY 11949
$139,999

2 beds

|

1 baths

|

938 sq ft

|

Condo

40 GREENWOOD BLVD, BROOKHAVEN, NY, 11949
Community: Greenwood Village
Want to learn more about 55+ communities in Connecticut? 55places can help!
Questions? Call us: (888) 625-4885
Greenwood Village 5115 VILLAGE CIR, BROOKHAVEN, NY, 11949, Brookhaven, NY 11949
$299,999

2 beds

|

2 baths

|

1,134 sq ft

|

House

5115 VILLAGE CIR, BROOKHAVEN, NY, 11949
Community: Greenwood Village
The Greens at Half Hollow 387 ALTESSA BLVD, HUNTINGTON, NY, 11747, Huntington, NY 11747
$1,599,000

3 beds

|

3 baths

|

2,700 sq ft

|

Condo

387 ALTESSA BLVD, HUNTINGTON, NY, 11747
Heritage Village 62 HERITAGE VLG A, SOUTHBURY, CT, 06488, Southbury, CT 06488
$186,000

2 beds

|

2 baths

|

1,032 sq ft

|

Condo

62 HERITAGE VLG A, SOUTHBURY, CT, 06488
Community: Heritage Village
Oronoque Village 638 ONONDAGA LN A, STRATFORD, CT, 06614, Stratford, CT 06614
$499,000

1 beds

|

3 baths

|

1,175 sq ft

|

Condo

638 ONONDAGA 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.
Pond Spring Village 41 PONDVIEW CIR 41, BEACON FALLS, CT, 06..., Beacon Falls, CT 06403
$485,000

2 beds

|

2 baths

|

1,501 sq ft

|

Condo

41 PONDVIEW CIR 41, BEACON FALLS, CT, 06...
Community: Pond Spring Village
Rivington 19 WARRINGTON ROUND 19, DANBURY, CT, 068..., Danbury, CT 06810
$749,000

3 beds

|

3 baths

|

2,196 sq ft

|

Condo

19 WARRINGTON ROUND 19, DANBURY, CT, 068...
Community: Rivington
Heritage Village 786 HERITAGE VLG C, SOUTHBURY, CT, 06488, Southbury, CT 06488
$295,000

2 beds

|

2 baths

|

1,000 sq ft

|

Condo

786 HERITAGE VLG C, SOUTHBURY, CT, 06488
Community: Heritage Village
Village Vistas 11 THERESA LN, BROOKHAVEN, NY, 11777, Brookhaven, NY 11777
$1,249,000

3 beds

|

4 baths

|

3,075 sq ft

|

Condo

11 THERESA LN, BROOKHAVEN, NY, 11777
Community: Village Vistas
Evergreen 5 HARWOOD GDNS 5, CROMWELL, CT, 06416, Cromwell, CT 06416
$479,900

2 beds

|

2 baths

|

1,436 sq ft

|

Condo

5 HARWOOD GDNS 5, CROMWELL, CT, 06416
Community: Evergreen
Benson Woods 203 SUGAR MAPLE WAY 203, MIDDLEBURY, CT,..., Middlebury, CT 06762
$589,900

2 beds

|

3 baths

|

2,442 sq ft

|

Condo

203 SUGAR MAPLE WAY 203, MIDDLEBURY, CT,...
Community: Benson Woods
Leisure Village 379C WOODBRIDGE DR C, BROOKHAVEN, NY, 11..., Brookhaven, NY 11961
$459,900

2 beds

|

2 baths

|

1,168 sq ft

|

Condo

379C WOODBRIDGE DR C, BROOKHAVEN, NY, 11...
Community: Leisure Village
Want to learn more about 55+ communities in Connecticut? 55places can help!
Questions? Call us: (888) 625-4885
Leisure Glen 14 FLANDERS CT, BROOKHAVEN, NY, 11961, Brookhaven, NY 11961
$450,000

2 beds

|

2 baths

|

1,212 sq ft

|

House

14 FLANDERS CT, BROOKHAVEN, NY, 11961
Community: Leisure Glen
Heritage Village 219 HERITAGE VLG B, SOUTHBURY, CT, 06488, Southbury, CT 06488
$250,000

2 beds

|

2 baths

|

1,398 sq ft

|

Condo

219 HERITAGE VLG B, SOUTHBURY, CT, 06488
Community: Heritage Village
Heritage Village 974 HERITAGE VLG A, SOUTHBURY, CT, 06488, Southbury, CT 06488
$299,900

2 beds

|

2 baths

|

1,432 sq ft

|

Condo

974 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.
Heritage Village 847 HERITAGE VLG B, SOUTHBURY, CT, 06488, Southbury, CT 06488
$500,000

3 beds

|

2 baths

|

1,716 sq ft

|

Condo

847 HERITAGE VLG B, SOUTHBURY, CT, 06488
Community: Heritage Village
Country Pointe Preserve 103 FOXWOOD DR 73, BROOKHAVEN, NY, 11980, Brookhaven, NY 11980
$935,000

2 beds

|

3 baths

|

2,187 sq ft

|

Condo

103 FOXWOOD DR 73, BROOKHAVEN, NY, 11980
Heritage Village 369 HERITAGE VLG A, SOUTHBURY, CT, 06488, Southbury, CT 06488
$185,000

1 beds

|

1 baths

|

928 sq ft

|

Condo

369 HERITAGE VLG A, SOUTHBURY, CT, 06488
Community: Heritage Village
Heritage Village 26 HERITAGE VLG A, SOUTHBURY, CT, 06488, Southbury, CT 06488
$379,900

2 beds

|

2 baths

|

1,432 sq ft

|

Condo

26 HERITAGE VLG A, SOUTHBURY, CT, 06488
Community: Heritage Village
Heritage Village 24 HERITAGE CRST B, SOUTHBURY, CT, 06488, Southbury, CT 06488
$383,000

2 beds

|

2 baths

|

1,217 sq ft

|

Condo

24 HERITAGE CRST B, SOUTHBURY, CT, 06488
Community: Heritage Village
The Waterways at Moriches 129 CAPTAINS CT, BROOKHAVEN, NY, 11955, Brookhaven, NY 11955
$749,000

2 beds

|

2 baths

|

1,762 sq ft

|

Condo

129 CAPTAINS CT, BROOKHAVEN, NY, 11955
Rivington 42 COUNTRY VIEW RD 42, DANBURY, CT, 0681..., Danbury, CT 06810
$1,175,000

3 beds

|

4 baths

|

2,709 sq ft

|

Condo

42 COUNTRY VIEW RD 42, DANBURY, CT, 0681...
Community: Rivington
The Village at Buckingham 10 CHELSEA PL 10, AVON, CT, 06001, Avon, CT 06001
$614,900

3 beds

|

3 baths

|

2,430 sq ft

10 CHELSEA PL 10, AVON, CT, 06001
Want to learn more about 55+ communities in Connecticut? 55places can help!
Questions? Call us: (888) 625-4885
Sunken Pond Estates 1504 PEBBLE BEACH PATH, RIVERHEAD, NY, 1..., Riverhead, NY 11901
$545,000

2 beds

|

2 baths

|

1,258 sq ft

|

House

1504 PEBBLE BEACH PATH, RIVERHEAD, NY, 1...
Community: Sunken Pond Estates
Bidwell Village 94 STONEHOUSE RD 6, COVENTRY, CT, 06238, Coventry, CT 06238
$449,900

3 beds

|

3 baths

|

1,905 sq ft

|

Condo

94 STONEHOUSE RD 6, COVENTRY, CT, 06238
Community: Bidwell 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.



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: Oct 30, 2026.
This application does not include information on all of the properties available for sale at this time.

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