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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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Pond Spring Village
$300ks
Pond Spring Village, Beacon Falls, CT
New and Resale | 55+ age-restricted | Built 2005 - present | 92 homes
The Cottages at Wire Mill
$1Ms
The Cottages at Wire Mill, Stamford, CT
New Construction | 55+ age-restricted | Built 2026 - present | 9 homes
Vineyards at Moriches
$500ks - $600ks
Vineyards at Moriches, Center Moriches, NY
Resale Only | 55+ age-restricted | Built 2008 - 2014 | 92 homes
Stoneleigh Woods at River...
$500ks
Stoneleigh Woods at River..., Riverhead, NY
Resale Only | 55+ age-restricted | Built 2007 - 2016 | 176 homes
The Seasons at East North...
$700ks
The Seasons at East North..., East Northport, NY
New Construction | 55+ age-restricted | Built 2023 - present | 190 homes
Want to learn more about 55+ communities in Connecticut? 55places can help!
Questions? Call us: (888) 625-4885
Regency at Prospect
$300ks - $400ks
Regency at Prospect, Prospect, CT
Resale Only | 55+ age-restricted | Built 2006 - 2020 | 379 homes
5 rating (1 review) Encore at Lake Grove
$500ks - $700ks
Encore at Lake Grove, Lake Grove, NY
Resale Only | 55+ age-restricted | Built 2006 - 2007 | 228 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
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
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.
Strathmore Gate East
$300ks
Strathmore Gate East, Coram, NY
Resale Only | 55+ age-restricted | Built 1970 - 1975 | 174 homes
5 rating (2 reviews) Benson Woods
$400ks - $600ks
Benson Woods, Middlebury, CT
New and Resale | 55+ age-restricted | Built 2004 - present | 79 homes
Regency Meadows
$500ks
Regency Meadows, Trumbull, CT
Resale Only | 55+ age-restricted | Built 2003 - 2005 | 51 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
Bidwell Village
$300ks - $400ks
Bidwell Village, Coventry, CT
New Construction | 55+ age-restricted | Built 2020 - present | 37 homes
Want to learn more about 55+ communities in Connecticut? 55places can help!
Questions? Call us: (888) 625-4885
Vineyards at Brookfield
$400ks - $500ks
Vineyards at Brookfield, Center Moriches, NY
New Construction | 55+ age-restricted | Built 2019 - present | 146 homes
5 rating (3 reviews) Founders Ridge
$300ks - $400ks
Founders Ridge, Middletown, CT
New Construction | 55+ age-restricted | Built 2017 - present | 75 homes
The Summit at Bethel
$500ks - $700ks
The Summit at Bethel, Bethel, CT
Resale Only | 55+ age-restricted | Built 2010 - 2021 | 235 homes
The Village at Buckingham
$300ks - $400ks
The Village at Buckingham, Avon, CT
Resale Only | 55+ age-restricted | Built 2002 - 2006 | 56 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 Village at Hunt Glen
$300ks
The Village at Hunt Glen, Granby, CT
Resale Only | 55+ age-restricted | Built 2003 - 2006 | 69 homes
Rivington Landing
$500ks
Rivington Landing, Danbury, CT
New Construction | Age-targeted | Built 2025 - 2026 | 25 homes
Granite Woods
$600ks - $700ks
Granite Woods, Middlebury, CT
New Construction | 55+ age-restricted | Built 2020 - present | 24 homes
The Bridges at Oxford Gre...
$600ks
The Bridges at Oxford Gre..., Oxford, CT
New Construction | 55+ age-restricted | Built 2025 - present | 99 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
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
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.
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
Baldwin Station
$400ks
Baldwin Station, Milford, CT
Resale Only | 55+ age-restricted | Built 2001 - 2003 | 82 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 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 Plymouth Estates at Mount Sinai 262 POND CIR 262, BROOKHAVEN, NY, 11766, Brookhaven, NY 11766
$599,000

2 beds

|

2 baths

|

1,820 sq ft

|

Condo

262 POND CIR 262, BROOKHAVEN, NY, 11766
New Foxwood Village 1407 MIDDLE RD 103, RIVERHEAD, NY, 11933, Riverhead, NY 11933
$449,000

2 beds

|

2 baths

|

1,586 sq ft

|

Manufactured Home

1407 MIDDLE RD 103, RIVERHEAD, NY, 11933
Community: Foxwood Village
Want to learn more about 55+ communities in Connecticut? 55places can help!
Questions? Call us: (888) 625-4885
New Foxwood Village 1407 MIDDLE RD 233, RIVERHEAD, NY, 11933, Riverhead, NY 11933
$405,000

3 beds

|

2 baths

|

3,133 sq ft

|

Manufactured Home

1407 MIDDLE RD 233, RIVERHEAD, NY, 11933
Community: Foxwood Village
New Greenwood Village 402 VILLAGE CIR, BROOKHAVEN, NY, 11949, Brookhaven, NY 11949
$250,000

2 beds

|

2 baths

|

1,122 sq ft

|

Condo

402 VILLAGE CIR, BROOKHAVEN, NY, 11949
Community: Greenwood Village
New Leisure Village 449 ARLINGTON DR, BROOKHAVEN, NY, 11961, Brookhaven, NY 11961
$310,000

2 beds

|

1 baths

|

1,074 sq ft

|

Condo

449 ARLINGTON DR, BROOKHAVEN, NY, 11961
Community: Leisure Village
New The Greens at Half Hollow 849 MADEIRA BLVD, HUNTINGTON, NY, 11747, Huntington, NY 11747
$738,888

2 beds

|

2 baths

|

1,150 sq ft

|

Condo

849 MADEIRA BLVD, HUNTINGTON, NY, 11747
New Heritage Village 399 HERITAGE VLG B, SOUTHBURY, CT, 06488, Southbury, CT 06488
$275,000

2 beds

|

2 baths

|

1,076 sq ft

|

Condo

399 HERITAGE VLG B, 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.
New Woodridge Strathmore Terrace 41 CHIPPENDALE DR, BROOKHAVEN, NY, 11766, Brookhaven, NY 11766
$599,000

2 beds

|

2 baths

|

1,501 sq ft

|

Condo

41 CHIPPENDALE DR, BROOKHAVEN, NY, 11766
New The Vineyards at Miller Place 48 AVERY LN, BROOKHAVEN, NY, 11764, Brookhaven, NY 11764
$619,996

2 beds

|

3 baths

|

1,486 sq ft

|

Condo

48 AVERY LN, BROOKHAVEN, NY, 11764
New Leisure Glen 562 LEISURE DR, BROOKHAVEN, NY, 11961, Brookhaven, NY 11961
$670,000

2 beds

|

2 baths

|

1,652 sq ft

|

House

562 LEISURE DR, BROOKHAVEN, NY, 11961
Community: Leisure Glen
New Leisure Glen 3 BALDWIN CT, BROOKHAVEN, NY, 11961, Brookhaven, NY 11961
$519,900

2 beds

|

2 baths

|

1,542 sq ft

|

Condo

3 BALDWIN CT, BROOKHAVEN, NY, 11961
Community: Leisure Glen
New Greenwood Village 24 GREENWOOD BLVD, BROOKHAVEN, NY, 11949, Brookhaven, NY 11949
$79,999

1 beds

|

1 baths

|

812 sq ft

|

Condo

24 GREENWOOD BLVD, BROOKHAVEN, NY, 11949
Community: Greenwood Village
New Leisure Village 470B DARWEN DR, BROOKHAVEN, NY, 11961, Brookhaven, NY 11961
$339,000

2 beds

|

1 baths

|

1,074 sq ft

|

Condo

470B DARWEN DR, BROOKHAVEN, NY, 11961
Community: Leisure Village
Want to learn more about 55+ communities in Connecticut? 55places can help!
Questions? Call us: (888) 625-4885
New Meadow Brook Estates 107 MEADOW BROOK RD 107, OXFORD, CT, 064..., Oxford, CT 06478
$569,900

3 beds

|

3 baths

|

1,922 sq ft

|

Condo

107 MEADOW BROOK RD 107, OXFORD, CT, 064...
The Vineyards at Miller Place 40 AVERY LN, BROOKHAVEN, NY, 11764, Brookhaven, NY 11764
$625,000

3 beds

|

3 baths

|

1,700 sq ft

|

Condo

40 AVERY LN, BROOKHAVEN, NY, 11764
Leisure Glen 488 LEISURE DR, BROOKHAVEN, NY, 11961, Brookhaven, NY 11961
$659,000

2 beds

|

2 baths

|

1,652 sq ft

|

Condo

488 LEISURE DR, BROOKHAVEN, NY, 11961
Community: Leisure Glen
Stoneleigh Woods at Riverhead 904 BALTUSROL BLVD, RIVERHEAD, NY, 11901, Riverhead, NY 11901
$510,000

2 beds

|

2 baths

|

1,258 sq ft

|

Condo

904 BALTUSROL BLVD, RIVERHEAD, NY, 11901
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 27 HERITAGE CRST C, SOUTHBURY, CT, 06488, Southbury, CT 06488
$390,000

2 beds

|

2 baths

|

1,447 sq ft

|

Condo

27 HERITAGE CRST C, SOUTHBURY, CT, 06488
Community: Heritage Village
Regency at Prospect 146 SYCAMORE DR, PROSPECT, CT, 06712, Prospect, CT 06712
$550,000

2 beds

|

3 baths

|

1,850 sq ft

|

Condo

146 SYCAMORE DR, PROSPECT, CT, 06712
Community: Regency at Prospect
Fairfield at St. James 508 GOTHAM CT, SMITHTOWN, NY, 11780, Smithtown, NY 11780
$609,000

3 beds

|

3 baths

|

1,700 sq ft

|

Condo

508 GOTHAM CT, SMITHTOWN, NY, 11780
Kensington Estates 48 PLAINVIEW RD, OYSTER BAY, NY, 11797, Oyster Bay, NY 11797
$2,099,999

6 beds

|

5 baths

|

4,333 sq ft

|

House

48 PLAINVIEW RD, OYSTER BAY, NY, 11797
Community: Kensington Estates
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

|

Condo

43101 SILVER BIRCH LN, OYSTER BAY, NY, 1...
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
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
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
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
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
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 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
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
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
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: Nov 05, 2026.
This application does not include information on all of the properties available for sale at this time.

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