15 Best Places to Live in Connecticut

By PropertyClub Team
Jan 14th 2022
There are so many great cities and small towns throughout Connecticut that it can be tough to know where to start your search. So here is a look at 15 of the best places to live in the Constitution State.

hash-mark15 Best Places to Live in Connecticut

hash-markNew Haven

New Haven is quite possibly the best place to live in Connecticut thanks to it's wonderful cultural and entertainment scenes as well as it's abundance of beautiful green spaces. Often known as the cultural capital of Connecticut, New Haven is home to Yale University and a variety of parks, art galleries, museums, and famous restaurants. New Haven blends the colonial charm of a classic New England town with the cosmopolitan amenities of a major city. It’s one of the most walkable cities in America, with picturesque brick-paved streets that are lined with independent shops and restaurants. Plus, it has a reliable public transportation system with commuter trains into New York City, Springfield, and Hartford.  

hash-markGreenwich

The largest city in Connecticut’s Gold Coast, Greenwich is one of the best towns in Connecticut. It's also one of the oldest towns in the state and features a bustling economy and rich history. It’s only an hour outside of New York City, making it a popular commuter town for working professionals. Greenwich has a small-town charm with big-city amenities easily accessible. It offers a variety of shopping and dining options, as well as multiple public parks and close to 150 acres of beaches along the Long Island Sound. One of its most popular neighborhoods, Cos Cobb, is located along the shoreline and features various national landmarks and art galleries.

hash-markWest Hartford

Located five miles west of downtown Hartford, West Hartford is a community that is also consistently ranked one of the best places to live in the country. The town is home to the University of Hartford and the University of Saint Joseph, offering a plethora of employment and educational opportunities. The town’s downtown center, also known as the West Hartford Center, is located along Farmington Road and Main Street and features a variety of world-class shops and restaurants. Elizabeth Park is another local attraction with greenhouses, nature walks, and picturesque flower and rock gardens. West Hartford is well known for its quaint, old-world charm and affordable real estate compared to other popular areas in the state, making it an excellent destination for growing families.

hash-markNew Canaan

New Canaan is a small city within Connecticut’s Gold Coast. Situated under an hour from Manhattan, it’s a popular commuter city and consistently ranked among the wealthiest areas in the country. The city is famous for its unique mid-century architecture, boasting picturesque homes designed by famous architects such as Marcel Breuer, Eliot Noyes, and Philip Johnson. New Caanan is also known for its exceptional schools, low crime rate, and gorgeous parks. Residents enjoy a variety of world-class restaurants, designer boutiques, upscale gyms, and nearby ski mountains, offering something for everyone. New Canaan is a peaceful town in the northwest corner of the state that offers a quiet escape from the hustle and bustle of the city.

hash-markSimsbury

Simsbury is a popular suburb of Hartford, located in the Farmington River Valley beside the Metacomet Ridge. The town offers the perfect blend of suburban convenience and rural serenity. Talcott Mountain State Park is a popular destination for outdoor enthusiasts with hiking trails, waterfalls, clifftop lookouts, and ponds for fishing and swimming. Plus, the town is full of gorgeous historic homes, fabulous restaurants, and public parks. Simsbury is a great town for those in search of quality schools, employment opportunities, and a relaxed pace of life.

hash-markOld Greenwich

Old Greenwich is a neighborhood in Greenwich, Connecticut, that is known for being one of the wealthiest communities in America. The city’s oldest neighborhood, Old Greenwich, was first settled in 1640. It offers a quick commute into Manhattan and gorgeous views of the Long Island Sound. The community has a sparse, suburban feel with multiple parks and open green spaces, including the 147-acre Greenwich Point, which features stretches of sandy beaches and scenic views of New York City across the water. The downtown area is full of quaint local shops and restaurants that range from fine dining to seafood. Old Greenwich offers comfort and sophistication, which is why it’s consistently ranked one of the best places to live in America.

hash-markWeatogue

Weatogue is a small village in Hartford County. Situated along the Farmington River, Weatogue offers gorgeous scenery, great schools, and high quality of life. The town features a variety of amazing local coffee shops, restaurants, and parks. Residents have an easy commute into downtown Hartford or Springfield. Plus, it has a low crime rate and affordable housing prices, which attract young families. Weatogue is a peaceful suburb with friendly neighbors and a small-town charm that attracts residents of all backgrounds. It’s one of the best places to live in Connecticut if you’re looking for a cozy, small-town vibe with a tight-knit community. 

hash-markSouthport

Located along the Long Island Sound in between Mill River and Sasco Brook, Southport is a seaside town in Fairfield County. Conveniently located just an hour outside New York City, the hamlet is popular for commuters. The village features picturesque tree-lined blocks, classic New England architecture, and a seaport with a yacht club. Southport features a designated historic district with homes in various popular architectural styles, including Greek Revival, Georgian, Victorian, Romanesque, and Federal. It’s a bit pricier than other areas, but it features an air of sophistication that many residents love.

hash-markDarien

Darien is a seaside town in Fairfield County, located within Connecticut’s Gold Coast. Situated just 37 miles northeast of New York City, the town is popular amongst commuters and features two Metro-North Stations which stop at Grand Central. The town features a variety of recreational opportunities with two beaches, eleven parks, multiple country clubs, and two yacht clubs. Darien is great for those in search of a peaceful, seaside community with an abundance of recreational opportunities nearby.

hash-markGlastonbury

Glastonbury is a town in Hartford County, located along the Connecticut River. The town features a family-friendly community with excellent schools, plenty of parks, and low crime. Downtown Hartford is only about 10 minutes away, and it’s under an hour’s drive to the beach. Rose’s Berry Farm is a popular weekend destination in Glastonbury and allows visitors to pick their own strawberries, blackberries, raspberries, peaches, and pears. The Cotton Hollow Preserve is another local attraction with 80 acres of preserved woodlands where residents can fish or go hiking. Glastonbury is a laidback suburb with a high quality of life that attracts both families and working professionals. 

hash-markWeston

Weston is a small town in Fairfield County, located 4 miles east of New York City. With the highest median income in the state of Connecticut, Weston is one of the wealthiest communities in the United States. The town is primarily known as a bedroom community for those who work in New York. The Devil’s Den Nature Preserve is mostly located in Weston and features close to 1800 acres of animal habitats and hiking trails. The town offers the perfect balance of country living and modern conveniences, making it an ideal location for commuters looking for a peaceful escape from the city.  

hash-markAvon

Avon is a town in the Farmington Valley region of Hartford County. It offers the charm of a small New England town with a variety of amenities close at hand. Residents will find a plethora of shops and restaurants down at Avon Marketplace or Riverdale Farms Shopping. There is also plenty of opportunity for outdoor recreation down at Buckingham Park, Sycamore Hills Recreation Area, or nearby Talcott Mountain. Plus, the small town offers excellent public schools, affordable homes, and a low crime rate, making it one of the most desirable towns in Connecticut. 

hash-markCheshire

Cheshire is a gorgeous residential community located in New Haven County. Ranked by Money Magazine as one of the top 50 places to live in the US, Cheshire is a safe community with great schools and a high quality of life. In a prime location between New Haven and Hartford, Cheshire offers rural serenity with easy access to popular cities. Sleeping Giant State Park is a local favorite that features two miles of mountain tops with a lookout tower, nature trails, and picnic areas. Plus, every year the city hosts an annual Strawberry Festival with live music, craft goods made by local artisans, and plenty of fresh fruit. Cheshire is a great place for those searching for a family-friendly community in a gorgeous natural setting.

hash-markRidgefield

Ridgefield is a picturesque town in Fairfield County, located in the foothills of the Berkshire Mountains. The charming New England village has a historic downtown area that features a variety of shops and restaurants. Local attractions include the Aldrich Contemporary Art Museum, Prospector Theater, and downtown Ballard Park. Plus, the community features a highly rated public school system, a low crime rate, and plenty of employment opportunities. Ridgefield is perfect for those in search of gorgeous scenery and unique local culture.

hash-markWoodbridge

Woodbridge is a quiet suburb of New Haven that offers safe neighborhoods, excellent schools, and easy access to shopping. The town is in a convenient location 80 miles east of New York City, 40 miles south of Hartford, and 130 miles southwest of Boston, with easy access to local highways. But it has a rural, small-town feel with acres of lush countryside and woodlands with miles of hiking trails and ponds for fishing. Plus, it features a renowned school system with a low teacher-to-student ratio, making it the perfect place to raise a family.