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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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Saddle Lakes
$400ks - $500ks
Saddle Lakes, Riverhead, NY
Resale Only | 55+ age-restricted | Built 2000 - 2002 | 196 homes
Regency at Prospect
$300ks - $400ks
Regency at Prospect, Prospect, CT
Resale Only | 55+ age-restricted | Built 2006 - 2020 | 379 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 Village at Buckingham
$300ks - $400ks
The Village at Buckingham, Avon, CT
Resale Only | 55+ age-restricted | Built 2002 - 2006 | 56 homes
The Powder Forest Homes
$500ks - $700ks
The Powder Forest Homes, Simsbury, CT
Resale Only | 55+ age-restricted | Built 2006 - 2016 | 182 homes
Want to learn more about 55+ communities in Connecticut? 55places can help!
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5 rating (3 reviews) Founders Ridge
$300ks - $400ks
Founders Ridge, Middletown, CT
New Construction | 55+ age-restricted | Built 2017 - present | 75 homes
Billingsgate
$400ks - $600ks
Billingsgate, Simsbury, CT
Resale Only | 55+ age-restricted | Built 2003 - 2006 | 37 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
Whitney Glen
$500ks - $600ks
Whitney Glen, Westport, CT
Resale Only | 55+ age-restricted | Built 1982 - 1982 | 62 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.
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
Strathmore Gate East
$300ks
Strathmore Gate East, Coram, NY
Resale Only | 55+ age-restricted | Built 1970 - 1975 | 174 homes
Country Village Estates
$300ks
Country Village Estates, Coram, NY
Resale Only | 55+ age-restricted | Built 1993 - 2001 | 195 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
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
The Seasons at East North...
$700ks
The Seasons at East North..., East Northport, NY
New Construction | 55+ age-restricted | Built 2023 - present | 190 homes
Country Pointe Preserve
$600ks - $900ks
Country Pointe Preserve, Yaphank, NY
New Construction | 55+ age-restricted | Built 2024 - present | 152 homes
The Cottages at Wire Mill
$1Ms
The Cottages at Wire Mill, Stamford, CT
New Construction | 55+ age-restricted | Built 2026 - present | 9 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.
South Pond Village
$300ks - $400ks
South Pond Village, Bloomfield, CT
Resale Only | 55+ age-restricted | Built 1999 - 2005 | 151 homes
Cobblestone Court
$400ks - $500ks
Cobblestone Court, Essex, CT
New and Resale | 55+ age-restricted | Built 2017 - present | 8 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
Summer Wind Estates
$300ks - $400ks
Summer Wind Estates, North Haven, CT
New Construction | 55+ age-restricted | Built 2015 - present | 18 homes
RiverBend Estates
$400ks
RiverBend Estates, Oxford, CT
New and Resale | 55+ age-restricted | Built 2012 - present | 25 homes
Park Glen
$300ks - $500ks
Park Glen, New Milford, CT
Resale Only | 55+ age-restricted | Built 2006 - 2015 | 17 homes
Oak Meadow Estates
$200ks - $300ks
Oak Meadow Estates, Torrington, CT
New and Resale | 55+ age-restricted | Built 2013 - present | 31 homes
Want to learn more about 55+ communities in Connecticut? 55places can help!
Questions? Call us: (888) 625-4885
Hopmeadow Place
$200ks - $300ks
Hopmeadow Place, Simsbury, CT
Resale Only | 55+ age-restricted | Built 2005 - 2005 | 66 homes
Gloria Commons
$200ks - $300ks
Gloria Commons, Milford, CT
Resale Only | 55+ age-restricted | Built 2007 - 2015 | 50 homes
Eastport Meadows
$400ks
Eastport Meadows, Eastport, NY
Resale Only | 55+ age-restricted | Built 2009 - 2016 | 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.
Boulder Brook
$200ks
Boulder Brook, Prospect, CT
Resale Only | 55+ age-restricted | Built 2004 - 2006 | 35 homes
The Atrium of Portland
<$100k
The Atrium of Portland, Portland, CT
Resale Only | 55+ age-restricted | Built 2004 - 2004 | 56 homes
Autumn Estates
$500ks - $600ks
Autumn Estates, Farmington, CT
Resale Only | 55+ age-restricted | Built 2011 - 2017 | 30 homes
The Seasons at Plainview
$500ks - $600ks
The Seasons at Plainview, Plainview, NY
Resale Only | 55+ age-restricted | Built 2006 - 2007 | 134 homes
Bartlett Hollow
$200ks - $400ks
Bartlett Hollow, Middletown, CT
New Construction | 55+ age-restricted | Built 2015 - present | 25 homes
77 Sunset Lane
$400ks - $700ks
77 Sunset Lane, Ridgefield, CT
Resale Only | 55+ age-restricted | Built 2016 - 2018 | 54 homes
Clockmaker's Hill
$100ks
Clockmaker's Hill, Winsted, CT
Resale Only | 55+ age-restricted | Built 2005 - 2014 | 38 homes
The Summit at Bethel
$500ks - $700ks
The Summit at Bethel, Bethel, CT
Resale Only | 55+ age-restricted | Built 2010 - 2021 | 235 homes
Want to learn more about 55+ communities in Connecticut? 55places can help!
Questions? Call us: (888) 625-4885
Setauket Meadows
$500ks - $600ks
Setauket Meadows, Setauket, NY
Resale Only | 55+ age-restricted | Built 2005 - 2007 | 150 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.
Greenwood Village 5107 VILLAGE CIR, BROOKHAVEN, NY, 11949, Brookhaven, NY 11949
$265,000

2 beds

|

2 baths

|

1,123 sq ft

|

Condo

5107 VILLAGE CIR, BROOKHAVEN, NY, 11949
Community: Greenwood Village
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 Leisure Village 8 GUILFORD CT A, BROOKHAVEN, NY, 11961, Brookhaven, NY 11961
$388,000

2 beds

|

1 baths

|

1,085 sq ft

|

Condo

8 GUILFORD CT A, 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 Leisure Village 348 WOODBRIDGE DR B, BROOKHAVEN, NY, 119..., Brookhaven, NY 11961
$379,000

2 beds

|

2 baths

|

1,168 sq ft

|

House

348 WOODBRIDGE DR B, BROOKHAVEN, NY, 119...
Community: Leisure Village
New The Greens at Half Hollow 603 BARDINI DR, HUNTINGTON, NY, 11747, Huntington, NY 11747
$1,349,999

3 beds

|

3 baths

|

2,500 sq ft

|

Condo

603 BARDINI DR, HUNTINGTON, NY, 11747
New Country Village Estates 44 THEODORE DR, BROOKHAVEN, NY, 11727, Brookhaven, NY 11727
$490,000

2 beds

|

2 baths

|

1,386 sq ft

|

Condo

44 THEODORE DR, BROOKHAVEN, NY, 11727
New Oak Meadow Estates 25 OAK MEADOW LN 25, TORRINGTON, CT, 067..., Torrington, CT 06790
$444,900

2 beds

|

3 baths

|

2,164 sq ft

|

Condo

25 OAK MEADOW LN 25, TORRINGTON, CT, 067...
Community: Oak Meadow Estates
New Long Hill Village 71 CIDER MILL LN, TRUMBULL, CT, 06611, Trumbull, CT 06611
$595,000

1 beds

|

3 baths

|

2,660 sq ft

|

Condo

71 CIDER MILL LN, TRUMBULL, CT, 06611
Community: Long Hill 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 504 CARRIAGE DR 504, SOUTHINGTON, CT, 06..., Southington, CT 06489
$319,900

2 beds

|

2 baths

|

1,313 sq ft

|

Condo

504 CARRIAGE DR 504, SOUTHINGTON, CT, 06...
Community: Spring Lake Village
New Heritage Village 425 HERITAGE VLG A, SOUTHBURY, CT, 06488, Southbury, CT 06488
$200,000

2 beds

|

2 baths

|

1,432 sq ft

|

Condo

425 HERITAGE VLG A, SOUTHBURY, CT, 06488
Community: Heritage Village
New Oronoque Village 161 BISON LN A, STRATFORD, CT, 06614, Stratford, CT 06614
$575,000

2 beds

|

3 baths

|

1,426 sq ft

|

Condo

161 BISON LN A, STRATFORD, CT, 06614
Community: Oronoque Village
New Chatfield Farms 6 FIELDSTONE LN 6, BEACON FALLS, CT, 064..., Beacon Falls, CT 06403
$639,000

2 beds

|

3 baths

|

2,184 sq ft

|

Condo

6 FIELDSTONE LN 6, BEACON FALLS, CT, 064...
Community: Chatfield Farms
New Saddle Lakes 176 SCENIC LAKE DR, RIVERHEAD, NY, 11901, Riverhead, NY 11901
$575,000

2 beds

|

2 baths

|

1,247 sq ft

|

Condo

176 SCENIC LAKE DR, RIVERHEAD, NY, 11901
Community: Saddle Lakes
New Pond Spring Village 127 PONDVIEW CIR 127, BEACON FALLS, CT, ..., Beacon Falls, CT 06403
$465,000

2 beds

|

3 baths

|

1,328 sq ft

|

Condo

127 PONDVIEW CIR 127, BEACON FALLS, CT, ...
Community: Pond Spring Village
Want to learn more about 55+ communities in Connecticut? 55places can help!
Questions? Call us: (888) 625-4885
Glenwood Village 1661 OLD COUNTRY RD 77, RIVERHEAD, NY, 1..., Riverhead, NY 11901
$289,000

2 beds

|

2 baths

|

1,248 sq ft

|

Manufactured Home

1661 OLD COUNTRY RD 77, RIVERHEAD, NY, 1...
Community: Glenwood Village
Leisure Glen 8 FLANDERS CT, BROOKHAVEN, NY, 11961, Brookhaven, NY 11961
$559,000

2 beds

|

2 baths

|

1,212 sq ft

|

Condo

8 FLANDERS CT, BROOKHAVEN, NY, 11961
Community: Leisure Glen
Long Hill Village 36 CIDER MILL LN, TRUMBULL, CT, 06611, Trumbull, CT 06611
$525,000

2 beds

|

2 baths

|

1,370 sq ft

|

Condo

36 CIDER MILL LN, TRUMBULL, CT, 06611
Community: Long Hill Village
Encore at Lake Grove 9 SONATA CT, SMITHTOWN, NY, 11755, Smithtown, NY 11755
$599,000

2 beds

|

2 baths

|

1,685 sq ft

|

Condo

9 SONATA CT, SMITHTOWN, NY, 11755
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.
Plymouth Estates at Mount Sinai 53 ROSE LN, BROOKHAVEN, NY, 11766, Brookhaven, NY 11766
$499,999

2 beds

|

2 baths

|

1,272 sq ft

|

Condo

53 ROSE LN, BROOKHAVEN, NY, 11766
Sunken Pond Estates 1504 PEBBLE BEACH PATH, RIVERHEAD, NY, 1..., Riverhead, NY 11901
$545,000

2 beds

|

2 baths

|

1,258 sq ft

|

Condo

1504 PEBBLE BEACH PATH, RIVERHEAD, NY, 1...
Community: Sunken Pond Estates
Greenwood Village 33A LIMETREE DR, BROOKHAVEN, NY, 11949, Brookhaven, NY 11949
$144,999

2 beds

|

1 baths

|

800 sq ft

|

House

33A LIMETREE DR, BROOKHAVEN, NY, 11949
Community: Greenwood Village
Glenwood Village 1661 OLD COUNTRY RD 291, RIVERHEAD, NY, ..., Riverhead, NY 11901
$259,000

2 beds

|

2 baths

|

1,200 sq ft

|

Mobile Home

1661 OLD COUNTRY RD 291, RIVERHEAD, NY, ...
Community: Glenwood Village
Woodridge Strathmore Terrace 74 HEARTHSIDE DR, BROOKHAVEN, NY, 11766, Brookhaven, NY 11766
$549,990

2 beds

|

2 baths

|

1,240 sq ft

|

Condo

74 HEARTHSIDE DR, BROOKHAVEN, NY, 11766
Woodridge Strathmore Terrace 9 CHIPPENDALE DR, BROOKHAVEN, NY, 11766, Brookhaven, NY 11766
$439,000

2 beds

|

2 baths

|

1,240 sq ft

|

Condo

9 CHIPPENDALE DR, BROOKHAVEN, NY, 11766
Rivington 79 WINDING RIDGE WAY 79, DANBURY, CT, 06..., Danbury, CT 06810
$1,112,000

3 beds

|

4 baths

|

2,596 sq ft

|

Condo

79 WINDING RIDGE WAY 79, DANBURY, CT, 06...
Community: Rivington
Want to learn more about 55+ communities in Connecticut? 55places can help!
Questions? Call us: (888) 625-4885
Spring Lake Village 261 CARRIAGE DR 261, SOUTHINGTON, CT, 06..., Southington, CT 06489
$375,000

2 beds

|

2 baths

|

1,207 sq ft

|

Condo

261 CARRIAGE DR 261, SOUTHINGTON, CT, 06...
Community: Spring Lake Village
The Powder Forest Homes 4 ASHTON CIR 4, SIMSBURY, CT, 06070, Simsbury, CT 06070
$729,000

2 beds

|

4 baths

|

2,381 sq ft

4 ASHTON CIR 4, SIMSBURY, CT, 06070
Leisure Knoll 259 EDINBURGH DR, BROOKHAVEN, NY, 11961, Brookhaven, NY 11961
$599,000

2 beds

|

2 baths

|

1,135 sq ft

|

Condo

259 EDINBURGH DR, BROOKHAVEN, NY, 11961
Community: Leisure Knoll
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 Riverhead 47 STONELEIGH DR, RIVERHEAD, NY, 11901, Riverhead, NY 11901
$599,999

2 beds

|

3 baths

|

1,942 sq ft

|

Condo

47 STONELEIGH DR, RIVERHEAD, NY, 11901
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
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
Foxwood Village 1407 MIDDLE RD 233, RIVERHEAD, NY, 11933, Riverhead, NY 11933
$405,000

3 beds

|

2 baths

|

1,792 sq ft

|

Manufactured Home

1407 MIDDLE RD 233, RIVERHEAD, NY, 11933
Community: Foxwood Village
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
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
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
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
Want to learn more about 55+ communities in Connecticut? 55places can help!
Questions? Call us: (888) 625-4885
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
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
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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© 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 11, 2026.
This application does not include information on all of the properties available for sale at this time.

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