Lifestyle
Home to a rich maritime history and a stunning shoreline on the Long Island Sound, Connecticut is a wonderful state for retirees to call home. The Nutmeg State is small, but makes up for its quaintness by being close to New York, where seniors can access museums, entertainment, medical care, and more—although it should be noted that Connecticut has much of these amenities, as well. The state is known for its picturesque natural beauty, calming beaches, and historically-significant architecture.
C.E Larusso
Published March 2nd, 2026
Updated March 2nd, 2026
C.E Larusso
•
Published March 2nd, 2026
•
Updated March 2nd, 2026
Table of Contents
Key Takeaways
Connecticut is a beautiful state, with many towns and cities surrounded by lakes, parks, and rivers
Some retirement locations are situated right on the Long Island Sound, giving seniors the opportunity to enjoy waterfront living
New York City is accessible by train from much of Connecticut
While winters are on the colder side, the state overall has mild weather and four very distinct seasons
Connecticut taxes Social Security (in addition to all other retirement income) unless you are below a certain AGI
Is Connecticut a good place to live for retirees?
Connecticut is a draw for retirees looking for natural beauty, charming, historic towns, and easy access to major cities such as New York. The state also has bountiful cultural activities throughout the year, including events such as the Connecticut Wine Festival and the Connecticut Folk Festival.
While winters are snowy and cold, summers are relatively mild and the other seasons boast exceptional beauty with changing leaf colors and spring flowers—seasons are distinct, and overall pleasant in Connecticut.
That said, Connecticut has a higher cost-of-living than many other states. There are affordable towns—with several listed here—but the state does exceed the national average, with housing and healthcare costs the most expensive factors.
Is Connecticut tax-friendly for seniors?
Connecticut is not tax-friendly for retirees. Social Security and all other forms fo retirement income are taxed, although there are some exceptions for the Social Security taxation if you fall below a certain AGI. Single filers with an adjusted gross income below $75,000 will not pay taxes on Social Security; joint filers can make up to $100,000.
Connecticut also has a higher property tax rate, coming in at 1.66%, but there is some good news: the state has a single, blanket sales tax of 6.35%, with no additional sales tax on the local level.
Do seniors in Connecticut pay property taxes over 65?
Seniors over 65 do indeed need to pay taxes, however there is a program for lower-income seniors to help lessen the burden.
The Homeowner Program offers property tax credits from $150 to $1,250 and is intended for low-income seniors or disabled homeowners on their primary residence. To qualify, the property owner must be 65 years of age as of December 31 preceding the filing period, or is at least 50 years old and the widow(er) of a previously approved applicant, or is considered totally disabled. The applicant’s income must be $46,300 or less (single filers) or $56,500 (joint filers). What benefits do seniors get in Connecticut?
In addition to property tax breaks for low-income seniors as well as federal Medicaid, the state has a few additional programs and services to support retirees, including:
- Free public transportation: this varies by municipality, but many in the state offer free (or reduced) CT transit
- Discounted education: Many public colleges and universities in Connecticut offer tuition-free classes
- Utilities: The state has two programs (CEAP and CHAP) to help low-income residents offset the cost of their heating bills
- Support network: The Grandparents Raising Grandchildren program is designed to connect grandparents, relative caregivers, and providers to swap information about services, opportunities, and join together in community
Where is the best place to retire in Connecticut?
Connecticut has many different types of environments for retirees to choose from, between its busier cities—like Stamford—and beachfront resort towns like Madison. The state is close to New York, allowing for those who choose a quieter spot to access a metropolis and all of its amenities. Ultimately, choosing the best place to retire in Connecticut will depend on your priorities, preferences, and budget.
1. Mystic
CITY POPULATION: 4,483
SHARE OF POPULATION 65+: 39%
COST OF LIVING FOR RETIREES: 6% above the national average
MEDIAN HOME VALUE: $397,751
MEDIAN RENT: $2,005
TAX RATING FOR RETIREES: Not Tax Friendly
A coastal town, Mystic has a distinct maritime feel, due largely to its history: it was once a shipyard, and manufactured hundreds of ships starting in the 1700s. Even though it’s a small town, it’s home to numerous cultural attractions, including the Seaport Museum, a museum of art, and a local cinema. Between these and the stunning waterfront, seniors can stay active and engaged during retirement.
2. Southbury
CITY POPULATION: 19,973
SHARE OF POPULATION 65+: 30%
COST OF LIVING FOR RETIREES: 9% above the national average
MEDIAN HOME VALUE: $432,546
MEDIAN RENT: $2,300
TAX RATING FOR RETIREES: Not Tax Friendly
Southbury is located near multiple other towns such as Woodbury, Newton, Oxford, as well as Danbury, which has a highly-ranked hospital. The median age in Southbury is 51, so retirees will feel at ease with other empty nesters around. Active seniors can enjoy hiking, walking, or fishing at Naugatuck State Forest or Southford Falls State park, which has a picturesque waterfall.
3. New Milford
CITY POPULATION: 28,115
SHARE OF POPULATION 65+: 16%
COST OF LIVING FOR RETIREES: 6% above the national average
MEDIAN HOME VALUE: $447,823
MEDIAN RENT: $2,000
TAX RATING FOR RETIREES: Not Tax Friendly
New Milford, located on the Housatonic River, has small-town charm and ample outdoor recreation opportunities. Between the river and nearby Candlewood Lake, locals can spend time boating, fishing, or going on scenic walks. The town does an excellent job catering to the needs of the older community, with numerous senior centers, social clubs, and recreation programs available.
4. New Haven
CITY POPULATION: 137,562
SHARE OF POPULATION 65+: 8%
COST OF LIVING FOR RETIREES: 9% above the national average
MEDIAN HOME VALUE: $384,535
MEDIAN RENT: $1,850
TAX RATING FOR RETIREES: Not Tax Friendly
New Haven is home to Yale University, which provides lifelong learning opportunities for seniors as well as endless cultural activities. The university also has local medical facilities, which consistently rank among some of the best in the country. A very walkable town, New Haven allows retirees to enjoy shops, cafes, restaurants, and parks on foot. Bonus: it’s renowned for its pizza, with the historic Frank Pepe’s serving pies since 1925.
5. West Hartford
COUNTY POPULATION: 64,083
SHARE OF POPULATION 65+: 20%
COST OF LIVING FOR RETIREES: 4% above the national average
MEDIAN HOME VALUE: $468,632
MEDIAN RENT: $2,231
TAX RATING FOR RETIREES: Not Tax Friendly
West Hartford frequently makes it to lists of the best places to live and retire in Connecticut, largely due to its relative affordability and walkability. The town has a vibrant downtown with many shops and restaurants, as well as parks and walking trails for outdoor exercise. West Hartford also has many locals over the age of 65, helping retirees feel at home and a part of a community.
6. Norwich
CITY POPULATION: 39,993
SHARE OF POPULATION 65+: 18%
COST OF LIVING FOR RETIREES: 6% above the national average
MEDIAN HOME VALUE: $282,154
MEDIAN RENT: $1,685
TAX RATING FOR RETIREES: Not Tax Friendly
Norwich, Connecticut is known as “the rose of New England” due to its rolling hills that are said to resemble rose petals. The city invests heavily in recreation, parks, infrastructure, and more, giving residents a very high quality of life. But, the real reason it made this list? It has lots of affordable housing options, especially for a state with a higher cost-of-living—most homes come in 30% below the national average.
7. Stamford
CITY POPULATION: 139,134
SHARE OF POPULATION 65+: 21%
COST OF LIVING FOR RETIREES: 30% above the national average
MEDIAN HOME VALUE: $672,970
MEDIAN RENT: $2,725
TAX RATING FOR RETIREES: Not Tax Friendly
Stamford is one of the more dense cities listed here, which may be a draw for retirees who want easy access to amenities, culture, and vibrant community. The city is also a short train ride away from New York, giving seniors access to an enormous metropolis and all the benefits that come with one. In addition, Stamford is rich with green spaces and parks, so those who want the balance of city life and quiet, nature-forward suburbia will be happy to call it home.
8. Danbury
CITY POPULATION: 88,683
SHARE OF POPULATION 65+: 21%
COST OF LIVING FOR RETIREES: 7% above the national average
MEDIAN HOME VALUE: $464,570
MEDIAN RENT: $2,500
TAX RATING FOR RETIREES: Not Tax Friendly
Danbury is known for being a family-friendly place to live, and works hard to maintain this image by hosting many community events throughout the year such as the Danbury Street Festival. It’s also home to Western Connecticut State University, offering retirees continuing education opportunities. Perhaps most importantly, the cost-of-living in Danbury is reasonable for New England, with median home prices lower than the national average.
9. Simsbury
CITY POPULATION: 24,747
SHARE OF POPULATION 65+: 26%
COST OF LIVING FOR RETIREES: 4.8% above the national average
MEDIAN HOME VALUE: $507,293
MEDIAN RENT: $2,213
TAX RATING FOR RETIREES: Not Tax Friendly
Simsbury is ideal for retirees looking for a slower-paced town with lots of nature and green spaces. The town is located in Central Connecticut, an area that is home to many local wineries—retirees can enjoy an afternoon touring them and their bucolic surroundings. In addition, Simsbury is only a 20-minute drive to Bradley International Airport, making travel a breeze.
10. Madison
CITY POPULATION: 17,688
SHARE OF POPULATION 65+: 25%
COST OF LIVING FOR RETIREES: 9% above the national average
MEDIAN HOME VALUE: $685,115
MEDIAN RENT: $3,500
TAX RATING FOR RETIREES: Not Tax Friendly
Once a shipping hub for commercial fishing and shipbuilding, Madison has a rich history and is known for its abundance of natural beauty, including its beaches. The town has a bustling downtown district—perfect for Sunday afternoon scrolls—plus stunning historic buildings. Madison is an excellent location for retirees looking for a waterfront, resort town lifestyle, with all the quaint features that go with that.
Bottom Line
Connecticut is a historic state—in fact, it was the fifth state to ratify the Constitution—with awe-inspiring natural beauty and proximity to beaches on the Long Island Sound. While it is one of a handful of states that taxes Social Security, it allows deductions for retirees under a certain income level and there are several towns that have housing prices below the national average. If you have your heart set on Connecticut, consider one of the locations on our list, and be sure to speak to a financial advisor at Retirable to review your investments and budget so you can determine which will allow you to live out your golden years in comfort.
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A professional content writer, C.E. Larusso has written about all things home, finance, family, and wellness for a variety of publications, including Angi, HomeLight, Noodle, and Mimi. She is based in Los Angeles.
Share this advice
A professional content writer, C.E. Larusso has written about all things home, finance, family, and wellness for a variety of publications, including Angi, HomeLight, Noodle, and Mimi. She is based in Los Angeles.