2019 Best Places to Live in Fairfield CountyAbout this List

Southport

• Suburb in Connecticut
• 1 review

Current Resident: I moved from the Lake Hills section of Fairfield to Southport about 13 years ago, and I love it here! There is a great sense of community and it feels like you are back in time when you enter the Southport Historic District. Everything is walking or biking distance away, which is a great plus. The restaurant scene is very nice with the Artisan and the Gray Goose representing the posh side of Southport. Southport cares a lot about the environment and nature, with Southport Park being a great little destination, and there is an ecological restoration taking place east of Pease Ave, South of Mill Hill Terrace, and north of I-95.
Read 1 Review

• A+

• A+

• 1,687 Population

Westport

• Suburb in Connecticut
• 38 reviews

Current Resident: The schools are excellent! Staples High School is a great school and colleges know that! This is the reason I moved here and it was worth it. The beach is very pretty, although after 13 years I’m not as excited by it! There is a mix of people... some nice and some spoiled/arrogant, so find your people. The town is safe, people leave their doors unlocked (although I never would). Main Street is fun and the restaurants are pretty good. Overall, I moved here for the kids and it was worth it. Now that I’m getting older, I’m ready to live in a place that’s warm all year!
Read 38 Reviews

• A+

• A+

• 27,777 Population

Old Greenwich

• Suburb in Connecticut
• 6 reviews

Current Resident: Old Greenwich is an incredible community — the absolute best in Connecticut. Safe, picturesque with highly regarded schools, Old Greenwich is an absolute treasure for those raising a family. There is a real sense of community making it town like no other. 40 minutes to Manhattan makes this town easily accessible to the world’s financial district and some of the most prestigious multinational business organizations. Real estate in town tends to range from $1.5M to around $8M making it a very expensive place to live, however, the personal and family-oriented benefits entirely outweigh the costs.

Simply put: Old Greenwich is a community worth experiencing!
Read 6 Reviews

• A+

• A+

• 6,860 Population

Ridgefield

• Town in Connecticut
• 104 reviews

Former Resident: Ridgefield is an upper middle class town in Fairfield County. Living in a town like Ridgefield comes with many positives. World class school system, a safe town center with little to no crime. Also the convenience to lower Westchester and New York City makes Ridgefield a very desirable place to live. Ridgefield is a family town, so to be single in Ridgefield is not that enjoyable. Ridgefield falls in line with surrounding towns such as New Canaan, Wilton and Westport. As you could imagine your bank account needs to fall in line as well. The pressures of wealth and status does not escape you in Ridgefield even though Ridgefield seems to be a more well rounded town. Ridgefield may give the effect of being snobby and pretentious but hey its Connecticut!
Read 104 Reviews

• A+

• A+

• 25,206 Population

Cos Cob

• Suburb in Connecticut
• 1 review

Current Resident: It's a quiet town with what seems to be a lot of wealthy residents in the area. One thing that is clear though is that the public high school - Greenwich High school - is a very well developed structure in this area. The school is bigger than most and has a diverse set of classes and faculty that really does help with the student's growth. There's so many classes that a student can choose from that it could honestly be said that the school caters to everyone's needs.
Read 1 Review

• A+

• A+

• 6,840 Population

Greenwich

• Suburb in Connecticut
• 70 reviews

Current Resident: Greenwich is by far the best place to live in the NYC metro area. Dramatically lower taxes, relaxing beaches (islands too) multiple Audubon preserves for hiking, excellent Greenwich management of facilities.
Recommendations: Take the beautiful drive on Round Hill Road, Lake Avenue, Clapboard Ridge Road, North Street - these roads are understandably called the Golden Triangle - nothing like this residential area, every home has estate like grounds surrounded with timeless stonewalls. Formal dining: L'Escalier and Harvest Wine Bar Casual /Family Dining: Meli Melo and Beach House . If visiting during the day don't miss seeing Tod's Point, you will instantly feel like you are on a vacation far from NYC (but you are only a 50 minute train ride away).
Read 70 Reviews

• A+

• A+

• 62,782 Population

Newfield

• Neighborhood in Stamford, CT
• 48 reviews

Niche User: The environment is great for young professionals with a great downtown environment, lots of restaurants and activities, access to the train and NYC, and Stamford one of the safest cities in America. Many people wish the schools were better or would get better. As young people start having kids they have to move away because the school system is on the low-end. An underlying issue is the cost of living in Fairfield County is outrageous with average monthly rents in Stamford at $2,700 for 2015.
Read 48 Reviews

• A+

• B+

• 24,755 Population

New Canaan

• Suburb in Connecticut
• 33 reviews

Current Resident: New Canaan is an amazing community driven town with things to do for everyone! The volunteer opportunities are boundless and offer ways for everyone to get involved and make everyone feel they can be a part of an amazing community. There are many family focused, elderly focused, new resident focused, child & teen focused activities and one doesn't have to look far to become involved. The schools are top notch; the public places are beautifully maintained; the library & YMCA are top notch, town parks & pool are beautiful; there are art exhibits, parades, gatherings, pop up parks, broadway like shows at the high school, amazing restaurants and shops in the walkable downtown district and truly something for everyone!
Read 33 Reviews

• A

• A+

• 20,357 Population

Fairfield

• Suburb in Connecticut
• 90 reviews

Current Resident: We love the (relative) diversity, higher level of social awareness, walkability, food, access to nature. There is still a bit of "gold coast" that you have to roll your eyes at, but for the most part there's a lot of really good people. We went from late-20s young professionals to 30s parents of a young child during our four years so far in Fairfield. Both experiences were/have been great.

Each neighborhood in Fairfield has a really distinct personality, so I would do some additional research to see what neighborhood fits for you. We love that we can WALK to 6 parks/playgrounds, 5 beaches, hiking trails, fishing, a library that rivals some children's museums, national-act concerts, & the train to NYC or New Haven. At the same time, we have our own driveway and backyard where I can garden & have a bonfire with friends over without imposing on neighbors. The town amenities & services are great, much better than other area towns- tax $ actually worth it.
Read 90 Reviews

• A

• A+

• 61,611 Population

Riverside

• Suburb in Connecticut
• 6 reviews

Parent: My parents and my husband's parents were also born in the town of Greenwich so we have deep roots here. We have family throughout the town and I love raising my kids near their cousins and grandparents. We enjoy what the town has to offer in the way of sports and leisure activities. The downside is that it is expensive to live here and many people have lots of money.
Read 6 Reviews

• A

• A+

• 8,385 Population

Darien

• Suburb in Connecticut
• 34 reviews

Current Resident: Even though the community isn't very diverse, there are a lot of great opportunities to find there. The people are generally very nice, the school system is very well acclaimed, and having access to the beaches is a fantastic plus. The biggest downside would be the prices of housing and prices in general, but that's the case in the majority of Fairfield County.
Read 34 Reviews

• A

• A+

• 21,742 Population

Wilton

• Suburb in Connecticut
• 30 reviews

Current Resident: Just for reference, I have lived here my whole life. It is a wealthy suburban town with a large community, yet a very small-town feel. We have such a close-knit bond that we often refer to this as the "Wilton bubble." A great place for families and to raise kids, our school systems are very highly ranked and it is not uncommon to see kids here going off to very competitive and prestigious colleges such as Ivys when they leave. Plus, its very close to NYC! An hour train ride gets you right to the heart of Manhattan where you can find any opportunity that the small town lacks. Great for day trips, daily commutes to work, or even to take classes on weekend. Many people work in the city, which is why the houses here are huge and gorgeous and expensive cars are very common. Although if you don't fit into this "big house, expensive car" category, you never feel excluded or different. I have never felt unsafe here. All around great town.
Read 30 Reviews

• A

• A+

• 18,659 Population

Weston

• Suburb in Connecticut
• 19 reviews

Current Resident: Awesome community! Community is very diverse and accepting across ALL demographics. Schools are like a private education. Educators are some of the best in the nation! Although an expensive town to live, proud to be a resident. Quiet relative to events with the Memorial Fair as the big event of the year. Great for families , seniors and LGBTQ. Small town center that provides all the necessities without a far drive when needed. If you can make this town your home, you won't be disappointed,
Read 19 Reviews

• A

• A+

• 10,369 Population

Redding

• Town in Connecticut
• 28 reviews

Current Resident: Love the school system! The community is relaxed. Residents place a high value on the natural environment. You can hike for 60 miles on open space and be to the best malls and dining within 15 minutes. 60 minutes door to door drive to mid-town, or you can take the train from Redding station going direct to grand central in peak hours. Takes a little longer but I read a book, or the morning paper, or get ahead on my email. So worth it!
Read 28 Reviews

• A

• A+

• 9,274 Population

Trumbull

• Suburb in Connecticut
• 79 reviews

Current Resident: I've lived in Trumbull since I was born, I've attended public schools here. I am very comfortable and feel safe here. My friends and I meet up in the many parks that this town has to offer. We enjoy biking around town and hiking through the trails. There are a few lakes, I belong to a private one, and we can go kayaking, fishing...There is also 2 town outdoor pools and an indoor pool. We also have the Trumbull Mall we could go to, and we have a theatre with 16 screens! I would recommend this town to others, especially people with children.
Read 79 Reviews

• A

• A+

• 36,455 Population

Westover

• Neighborhood in Stamford, CT
• 26 reviews

Niche User: Its a great town to live in very clean, has enough room for everyone, schools provide kids what they need.
Read 26 Reviews

• A

• B+

• 18,509 Population

Newtown

• Town in Connecticut
• 102 reviews

Current Resident: I love almost everything about Newtown. I have had very pleasant experiences with the schools, and I have thoroughly enjoyed participating in some of the extracurricular activities, such as the Newtown High School Marching Band, where we won a US Bands State Championship and a US Bands National Championship in 2017. The community itself is very welcoming and friendly, and I have loved living here for my entire life!
Read 102 Reviews

• A

• A+

• 28,030 Population

Pemberwick

• Suburb in Connecticut

• A

• A+

• 4,281 Population

Turn of River

• Neighborhood in Stamford, CT
• 15 reviews

Niche User: Although crimes seem to have increased in Stamford, I would say that it is mostly concentrated in some areas of the city. The police do a good job of making sure that the general public is safe.
Read 15 Reviews

• A

• B+

• 6,996 Population

Byram

• Suburb in Connecticut
• 2 reviews

• A

• A+

• 4,601 Population

Easton

• Suburb in Connecticut
• 15 reviews

Current Resident: We love the lifestyle, the close knit community, the nature. Cute town, helpful people and a stones throw from many amenities around neighboring communities and New York City metro area. Great schools and great community!
Read 15 Reviews

• A-

• A+

• 7,607 Population

North Stamford

• Neighborhood in Stamford, CT
• 13 reviews

Current Resident: I’ve lived here 26 yrs and that’s longer than I’ve ever lived anywhere. Clean healthy air and a great place to raise children. Close enough to walk to LaRocca’s Market and Long Ridge Tavern. Five minute drive to house of Worship, Merritt and other shopping. Nice neighbors
Trees , grass, birds, flowers. To me, it’s a little corner of paradise.
Read 13 Reviews

• A-

• B+

• 22,791 Population

Brookfield

• Town in Connecticut
• 76 reviews

Current Resident: Brookfield is a quaint town in which I have lived for more than 13 years. I have done my K-12 education here, and with the high school programs, I have attended, I am prepared to move onto college in the year 2020. Brookfield is a very safe town, no crimes of violence. Everyone is amiable, and there is a great community feel. There are plenty of great restaurants, stores, a family-friendly park. Brookfield may not have a movie theatre or mall but Danbury, the neighboring town, does and its a short drive to both locations. Brookfield also has access to two large lakes which are bound to keep you cool and having fun all summer long!
Read 76 Reviews

• A-

• A

• 17,064 Population

Springdale

• Neighborhood in Stamford, CT
• 3 reviews

Current Resident: I have lived in Springdale in Stamford, CT for my entire life. Through the 18 years, I have noticed a lot of positives in the neighborhood. This is a very kid friendly neighborhood with Springdale little league and playground located directly in the center of town. You can find a ton of people walking into the shopping center just about a mile down the street with a skating rink, trampoline park, restaurants, and other shops. Springdale has a lot of housing and you can find many kids outside playing by turning down almost any street.
Read 3 Reviews

• A-

• B

• 16,590 Population

Bethel

• Town in Connecticut
• 32 reviews

Current Resident: Bethel is a lovely, quaint little town. Downtown Bethel is filled with adorable little shops and the best place to get breakfast, O'Neils. Bethel has lots of places to eat, many Italian restaurants. Bethel recently opened up a fantastic brewery. Bethel expands and has great shopping stores such as Target and Big Y. Another great feature of Bethel is the safety. The Bethel Police are always watching out. Bethel has a great public school system. Unfortunately, living in Bethel is expensive. The location is great because depending on where in Bethel you reside, there are many routes you can take to travel around the state or you can get on the highway.
Read 32 Reviews

• A-

• A

• 19,526 Population