For several years Connecticut has experienced a rise in house prices as more people are looking to settle in the suburbs while remaining close to a major city. This trend has shifted downward since 2018, but home prices remain extraordinarily high as more people consider this lovely Gold Coast state. Known for its top-notch school system, proximity to New York City, and quaint, colonial style, Fairfield County remains one of the most sought-after areas to live in Connecticut, comprising the top 5 most expensive places to buy a home in the Constitution State.
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Darien
This coastal town in Fairfield County is located just 37 miles northeast of New York City and boasts one of the most competitive school systems in the state. Outside of Connecticut and the east coast in general, Darien is ranked in the top 10 richest places in the country, with a median home value of $1,250,000. The town is situated on the Long Island Sound and many residents commute to Manhattan by way of two Metro-North railroad stations. Locals live lavishly, as the town of Darien offers 11 parks, two public beaches, a private beach club, three country clubs, a hunt club, the public Darien Boat Club, and Noroton Yacht Club.
Greenwich
Greenwich is the largest town on Connecticut’s Gold Coast, and it is the home to many hedge funds and financial service firms. It is known for its affluence and presence in various media, like television shows and films, and the median home price is $1,207,544. Greenwich is consistently ranked as one of the richest cities in America. It has much to offer, from extensive shopping to some of the best dining options outside of New York City. If you can afford the price tag, you’ll also get top-ranked private and public schools, parks, and beautiful beaches.
New Canaan
New Canaan is an affluent town in Fairfield County, where about a third of the residents commute to New York City for work. New Canaan schools consistently rank among the top public schools in the nation, and it is a wonderful setting for families. It’s no surprise that New Canaan ranks as the third most expensive place to buy a home in Connecticut, with a median home price of $1,207,544. The quaint downtown is lined with high-end boutiques and gourmet restaurants, and the town has an unrivaled sense of community.
Westport
Westport’s scenic waterfront and endless shopping and dining options make it one of the most unique and sought-after places to buy a home in Connecticut. The town has a median home price of $1,050,000. While most residents live there full-time, there is also an active summer rental market. The town offers a diverse array of activities and sights like shopping, dining, outdoor concerts, theatres, and arts — with two historic and quaint “downtown” areas full of small boutiques, businesses, and waterfront dining.
Weston
Weston is a quiet, wooded town in Fairfield County with top-notch schools and an affluent community of highly accomplished residents. The median home price is $685,000, which is significant drop from the top four most expensive towns. The town is like Westport in a way, but the biggest difference many people share is that it feels more laid back than your typical Fairfield County town, and it’s where people tend to go to have a little more space and quiet. Weston is a beautiful rural town where many residents look to Westport, Wilton, and surrounding areas for dining, shopping, and entertainment.