Top 25 Cities To Live In Connecticut

Connecticut is a small but mighty state located along the eastern coast of the United States. It only spans 70 miles from north to south and 110 miles from east to west, but there are so many exciting things within that small area. From the fantastic coastline to the incredible nature to explore, it’s no surprise that Connecticut is a highly desirable place to call home. There are plenty of amazing options for cities to settle down in as well. 


Simsbury is a beautiful suburb in Hartford County and is a town of affluence. It has a welcoming atmosphere and a low crime rate. It boasts excellent schools, so it’s an excellent place for individuals of all lifestyles. It’s a bit on the expensive side compared to the US average, but it’s a highly desirable place to call home. There’s plenty of nature to explore for outdoor enthusiasts, parks to enjoy, and history to learn about for those interested. 

Population: 24,979

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West Hartford

West Hartford is a city that welcomes people from all different lifestyles. For those who love a night out, there are some fantastic restaurants to enjoy, shopping to be had and plenty of things to do. The city is great for families with some of the best schools in the state and low crime rates. West Hartford’s economy is thriving, and there are plenty of opportunities to grow your career. It’s considered one of the most desirable areas in the state. The average home cost is around $320,000, with a median income of just under $100,000 per year. 

Population: 63,063

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While the small population of 18,000 makes Avon one of the smaller suburbs, it’s genuinely one of the best. Property values are a bit high, with the average sitting around $380,000, but there’s a reason why. The city is packed full of perks, and people are noticing. The economy is thriving, the crime rate is essentially non-existent, the school system is outstanding, and the convenient location allows residents to visit the other amazing cities around the state with ease. West Hartford, Simsbury, Farmington, and Collinsville are all next door. If you’re looking for something you can’t find in Avon, chances are you won’t have to go far to find it. 

Population: 18,302

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The smallest community on the list with a whopping 1,700 residents is Southport. It may be small, but it has so much to offer. The average household income is over $200,000 per year, and the school system is nothing short of incredible. Residents love calling Southport home. It has an old-fashioned vibe and a welcoming community atmosphere. 

Population: 1,661

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Westport is an affluent suburb where a three-bedroom home will run you over $1.2 million. The area offers an incredible quality of life, a convenient location, and so much more. The neighbors are welcoming, and it offers a place for everyone to fit in. It’s a special place with a slower pace, an incredible arts and theater scene, and a quick commute into NYC. It’s no surprise that residents love Westport and consider it well worth the high price tag. 

Population: 28,115

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Only 3,000 people call Weatogue home, but it’s surprising that more people don’t. The city offers incredible schools, beautiful parks and nature, low crime rates, and always something to do. The community constantly puts on events, festivals, concerts, and so much more. It’s the perfect place to meet your neighbors and make close friends. It’s a wonderful suburb that allows for a comfortable life. 

Population: 2,738

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Shelton is a relatively small city with a population of around 40,000 residents. It boasts a thriving economy, with a high household median income and a low cost of living. The average home price in the city is around $350,000. Shelton is the perfect community for older individuals to relocate or retire because the average age is around 47. 

Population: 41,141

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Milford is a beach lover’s dream. The city is located on the coastline and has a population of around 52,000 residents. The schools in the city have a low student-to-teacher ratio, which allows Milford to have the lowest drop-out rate in the state. With an average housing price of around $310,000, Milford is one of the most expensive places to buy a home in Connecticut. 

Population: 52,732

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Located about 15 minutes from New Britain, Middletown is home to nature and education. The Wesleyan University and Wadsworth Falls State Park both call the city of 46,000 residents home. With an exceptionally low unemployment rate, the commute time is one of the shortest in the state. Middletown boasts a low crime rate as well, making it a desirable place to raise a family. 

Population: 46,511

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Bristol is an affordable city just west of New Britain. It has low poverty and unemployment numbers and is home to just over 60,000 residents. Bristol is also incredibly safe, so it’s a great place to raise a family. The community is very liberal, so depending on your political affiliations, that might be a bonus for you. There’s also direct access to Lake Compounce, an exciting amusement park, and a water park. 

Population: 60,218

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Located in eastern Connecticut, Groton is home to a young population with the average age being around 35. There is a naval submarine base in the city, so it’s easy to join the navy. There’s plenty to see and do in this beautiful city and plenty of history to learn about. 

Population: 38,692

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Old Greenwich

Old Greenwich is the epitome of the best family-friendly community in the state. In fact, it’s rated number one among the best places in Connecticut to raise a family. It has massive appeal for couples looking to settle down or families looking to relocate. It’s not cheap, however, with homes costing over $1.4 million. Old Greenwich is a solid investment, and it will continue to be a desirable and popular community to call home. Its convenient location next to NYC, thriving economy, outstanding schools, first-class amenities, low crime rate, beautiful nature, sandy beaches, and welcoming community make it an idealistic place to call home. 

Population: 6,844

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Downtown, New Haven

The downtown area of most cities is always a great place to be. It’s one of the smaller areas, but it’s among the best in New Haven. It’s a very affordable place to call home, with the average home price being $160,000. It’s a typical college town, but a surprising flourishing restaurant scene is emerging, making it a place for foodies to flock. 

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Ridgefield is a first-class community with an average income of over $150,000 per year. In this area, you can expect nothing but the best. The streets are clean, schools are incredible, everyone is friendly, and the welcoming community is extremely safe. You can always find somewhere to explore, whether that’s a new restaurant or local shop or a nature trail and park. There’s always something to do, and the community will keep you busy throughout the year with a calendar full of events, festivals, and concerts. Ridgefield residents love entertainment. 

Population: 8,244

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Woodbridge is a well-educated, family-friendly community of almost 9,000 welcoming residents. The average home price is just under $500,000 with an annual income of around $140,000. 40% of Woodbridge residents have a master’s degree or higher, and 28% have a bachelor’s degree. Woodbridge boasts some of the best education for students, so it’s a great place to raise a family. Throughout the year, residents stay busy with all the amazing amenities and group events, concerts, and so much more. 

Population: 8,907

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Farmington is a popular and desirable community that is a bit on the expensive side. The average home price falls around $330,000, but it provides an excellent quality of life. There is plenty of history in Farmington to learn about, and it’s located conveniently, so it’s easy to explore some of the other cities on this list. There is a low crime rate, natural beauty, and phenomenal schools. It’s a beautiful community to raise a family and has so much to offer. 

Population: 25,430

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Cos Cob

In another ultra-luxe community close to NYC, the average three-bedroom home will set you back over a million dollars. However, that’s about the only disappointing part of Cos Cob. There are excellent job opportunities everywhere, fantastic amenities, incredible nightlife, endless dining options, and so much more. It’s the perfect place to go and hang out while meeting new friends. If you’re a lover of entertainment, nightlife, and delicious food, Cos Cob is the place to be. 

Population: 6,990

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Glastonbury has it all. It has opportunities, first-class amenities, attractions, a low crime rate, exceptional schools, and all the recreational activities you could ask for. Housing in the area is a bit expensive, but the lifestyle it affords residents is why they pay the higher prices. The average income is just over $110,000. There is so much to do in Glastonbury that residents are never bored. 

Population: 34,427

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Greenwich is well-known for how highly desirable it is as a community. Greenwich sounds like the ideal place for anyone to call home with plenty of job opportunities, a solid police presence, exceptional schools, and endless nature activities. Residents have access to every outdoor activity they could dream of in their backyard, include incredible beaches, hikes, parks, and playgrounds. A sizeable family home will cost you around $1.3 million in Greenwich. 

Population: 62,396

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Newfield, Stamford

One of the go-to communities in Stamford, it’s the highlight of the city. With only 25,000 residents, it has a small-town atmosphere with big-city amenities. The crime rate is almost zero, the school system is great, and the scenery is a big reason why people relocate to the area. The downtown area is always bustling with some excellent restaurants, nightlife, endless entertainment, and shopping. 

Population: 24,440

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New Canaan

The ultra-luxe community of New Canaan has some of the most beautiful estate homes around. With an average cost of almost $1.5 million, the city is anything but affordable. The suburb is close to NYC, so its convenient location and scenery make it very popular among those who can afford it. The median income for the area is around $175,000. The clean streets, low crime rate, and incredible parks are just the cherry on top of everything else it has to offer. 

Population: 20,213

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Fairfield is an exciting city in Connecticut that always has something to do or see. It has plenty of marvelous amenities like shopping, beaches, festivals, events, and much more. It’s a popular tourist area and welcomes many guests each year. It is one of the more expensive communities with an average home price of close to $600,000. Fairfield is a great place to call home for residents who love to live an exciting lifestyle attending events, socializing, and making friends.

Population: 62,105

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Orange is a small family-friendly town with around 11,000 residents. The average income is around $110,000 per year, and the average home price for a sizeable family home is just under $400,000. It has a low crime rate, exceptional schools, and a tight-knit community. It’s a great place to raise a family. 

Population: 13,956

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Mansfield is an affordable city, with housing prices falling around an average of just $235,000. The family-friendly community has excellent schools, nature to explore, parks to enjoy, and a welcoming atmosphere. It’s an affordable and ideal community to raise a family. 

Population: 26,543

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Riverside is the ultimate in luxurious Connecticut living. The school system is superior as one of the best in the state, but homes are well over a million dollars to own. It’s next door to New York and is an affluent community, with the average income being around $200,000 per year. 

Population: 8,604

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