Dina Cheney is a Fairfield County-based journalist. She covers lifestyle, including real estate, for many publications and brands. Dina is also the author of six books, including The New Milks.
Highly rated public schools, proximity to Manhattan, charming countryside, beaches. Fairfield County is an in-demand place to live—for good reason. These 10 towns are the best of the bunch. Listed in order by public school ranking, (full story here 2024 Best Public Schools in Fairfield County, CT) they all boast impressive safety stats plus an excess of charm and natural beauty. On the downside, cost can be an issue, with most homes starting around $800,000. Read on for a taste of each town, then get out your wallets!
Best for public schools: New Canaan
Along with the top-rated public school system, this picturesque inland community offers an extensive, vibrant, and walkable downtown. “It’s a central gathering place with great restaurants and shopping,” says resident and real estate agent, Taylor Tait. As another plus, “we do holidays well,” she notes. A few cases in point: the Easter Egg Hunt, December Holiday Stroll, and 4th of July Fireworks, when all residents are invited to its Waveny Park. A boon for those wanting less space, the town offers a “huge selection of condos walkable to downtown,” Tait shares. That said, the median list price is high: $2.4 million.
Most educated: Darien
The population of this waterfront community is the most educated, with 85% of adults having BAs or higher degrees. Plus, the public school system is stellar (it’s the second-highest rated among these towns). Another draw is the friendly and welcoming vibe, notes resident and local realtor, Amanda Spatola. “I really love the small-town feel. If you go to the local shops, you’ll see someone you know.” With two beaches, three country clubs, one yacht club, one boat club, one pool club, and one beach club, residents spend a lot of time outdoors, shares Casey Lange, fellow resident and realtor. On the downside, Darien is arguably the least accessible: it has the highest median listing price ($4.8 million) and highest median household income ($250,000-plus).
Most like a small town: Weston
“With two-acre zoning, Weston has a more rural feel,” says Linda Skolnick, a realtor who sells properties in town. With a mere 10,354 residents and about 3,550 households, this inland town includes just one elementary school, one middle school, and one high school—all highly rated. “The cute little town center has a market, hardware store, drug store, liquor store, and convenience store,” she notes. Despite a high median household income ($220,754), Weston is more accessible to buyers, with a median listing price of $1.5 million. “You’ll get more for your money here,” says Skolnick.
Top community: Wilton
“I love Wilton’s size and vibe,” says real estate agent, Lynne Murphy, who’s been a resident for 27 years. “People are grounded and have such town pride. It’s a tight knit and welcoming community.” Featuring rolling hills, meadows, old barns, and bodies of water, this inland town is scenic, with most of its homes on two-acre lots, she shares. Along with being only 10 minutes from several other towns, Wilton features a town center complete with must-visit donut shop, Rise Doughnuts (on Sunday mornings, stop by for their addictive apple fritters). Fortunately, real estate here is more affordable than in other top County towns. Starting around $595,000, according to Murphy, the median list price is $1.2 million.
Best waterfront: Westport
“Nothing is far from the beach—Westport is a beach town and feels like a vacation spot,” says Skolnick, a resident for more than 30 years. With draws including three beaches, a vibrant downtown and farmer’s market, and proximity to Manhattan, more empty nesters are staying for good, reveals Skolnick. Another bonus: the dynamic cultural scene. Residents can catch concerts at The Levitt Pavilion during the summer and watch shows at the historic Westport County Playhouse (many come here before they hit Broadway). It’s no surprise that many celebrities, like Michael Bolton and fashion designer, Christian Siriano, call Westport home. Accordingly, the median list price is high: $2.9 million.
Safest: Easton
Easton is tops when it comes to safety—which is saying a lot. With both the lowest violent and property crime rates, this inland town of about 7,600 residents is home to more than 20 working farms. Residents are educated, with at least 71% having BAs or higher degrees. Relatively affordable, the median household income is about $182,000 and the median home listing price is $1 million.
Most historic charm: Ridgefield
With its well-preserved downtown, this picture-perfect town is charming and historic. It’s also rich in green space, with its 7,600 residents spread out amongst woods, meadows, wetlands, and fields. Featuring highly regarded public schools, Ridgefield is home to an educated community: 77% of adults have at least BAs. One of the more affordable towns, the median listing price is $998,000 and the median household income is about $140,000.
Accessible to NYC and Hartford: Redding
Roughly equidistant from New York City and Hartford (about 50 miles), Redding is quite rural. Its 9,300 residents are spread out over 32 square miles, featuring valleys, streams, and the Saugatuck Reservoir (the town’s largest body of water). More affordable than many towns in the County, the median listing price is $1.2 million, and the median household income is $121,667.
Closest to NYC: Greenwich
Although coastal Greenwich is the closest County town to Manhattan, many of its 64,000 residents feel no need to leave. The downtown is bustling and extensive, and restaurants and amenities (including two beaches, four libraries, and an ice-skating rink) abound. Providing a sense of community, “Greenwich is made up of four separate neighborhoods offering a little something different for everyone,” says Jenny Allen, resident and real estate agent. “What I love most is that even though it may seem like a large town, Greenwich is a very tight knit community. The culture is characterized by a blend of sophistication, community engagement, and a high quality of life.” Not surprisingly, this comes at a price: the median list price here is a steep $3.8 million.
Most affordable: Fairfield
Comparable to Greenwich in population size and with a similarly bustling downtown, coastal Fairfield is the most affordable among these 10. With 63 homes currently on the market, the median list price is $922,500. Fortunately, residents don’t sacrifice when it comes to amenities: the town boasts two universities, three golf courses, two marinas, a sports plex, parks, and five beaches along five miles of coastline.
What’s Next
For those of you looking to buy a home in Fairfield County, Tomo.com provides free access to the most up to date real estate listings. You also can connect with a free home search advisor to get your journey started – by phone or text.
Want to know more about Public and Private schools in Fairfield County? Check out Tomo’s Best Public Schools in Fairfield County and Best Private Schools in Fairfield County.
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