Connecticut home buyers searching for an exclusive tristate enclave should focus their search on New Canaan, CT. Nestled in Fairfield County, New Canaan offers a captivating blend of history and modern living. 

Established in the 1700s, New Canaan has a stark colonial heritage providing an excellent counterpoint for folks who commute to NYC or New Haven. New Canaan has plenty of history, art, and a strong sense of community. 

To provide a perspective of this storied Town, the team at Prevu Real Estate put together a guide on the top reasons people choose to live in New Canaan, CT. 

Reasons to live in New Canaan

• Historical heritage 

• Stunning architecture 

• Beautiful outdoor spaces 

• Easy access to the tristate area

• Quaint downtown 

• Fine dining 

Historical heritage 

Part of the beauty of the Northeast is that you can live in timeless towns and cities that preserve America's founding history. For generations, New Canaan served as an agricultural community, and it was not until 1801 that the area became a town, albeit without a main street, town hall, or market square. 

Shoemaking became the town's leading trade, and throughout the 19th century, storied homes popped up in Ponus Ridge, West Road, and Talmadge Hill. However, the introduction of the New York, Hartford, and New Haven Railroad lines marked a turning point in the town's development. Wealthy NYC residents came to love the area's beauty, building summer homes that eventually became primary residences, allowing for easy commutes to and from the Big Apple. 

Today, many make the same trek, living in historic homes preserved from the 1800s in places like Oenoke Ridge while commuting daily to New York City. Oenoke Ridge is where you can find the New Canaan Museum & Historical Society, which has a treasure trove of historical data about the town. 

Stunning architecture 

A trip through New Canaan will expose a mosaic of varied home-styles, from colonial grandeur to modernist marvel. New Canaan's architecture reflects the area's rich history of innovation. In the heart of New Canaan, you can find plenty of modernized Victorian, Georgian, and Colonial homes from yesteryear, all adorned with columns, symmetrical woodwork designs, and charming interiors evoking a pastoral time. 

The architectural marvels from the Harvard Five make New Canaan stand out. In the mid-20th century, a group of modernist architects from the Harvard School of Design used New Canaan as a canvas to build liveable works of art. 

These upstart designers ushered in mid-century modernism in the Northeast by using open floor plans and blending steel, glass, brick, and other materials. One of the most famous homes from this era is the Glass House, built by Philip Johnson. 

Though it used to be his private estate, the Glass House now serves as a museum where locals and tourists can appreciate Johnson’s unique designs, including floor-to-ceiling glass panes that open up to vivid panoramas of the surrounding nature. 

Beautiful outdoor spaces 

One of the most coveted features of New Canaan homes is their large plot sizes. 

Most properties often come with multiple acres of well-manicured lawns and mature trees. Byways like Ponus Ridge Road and Frogtown Road have uninterrupted stretches of trees overhanging the road as you make your way through the area.

While New Canaan lacks the shorefront of Darien to the south, it makes up for it with its pristine parks and forests. Folks looking for a tranquil time in the woods should visit the Calhoun Preserve on Davenport Ridge Road. A well-beaten path winds through the trees, offering ample space for rest and relaxation after a long work day. 

If you like to relax by the water, you can travel to Laurel Reservoir by the New York border to rest by the shoreline or go for a paddle. Just make sure to look for submerged tree stumps. 

If the untamed woods do not appeal to you, you can find an unparalleled golfing experience at the Country Club of New Canaan, which has tennis and pickleball courts and a spa-like pool. 

Easy access to the Tri-State area 

Part of what makes New Canaan desirable is the myriad of routes folks can take to get to other parts of the northeast. Commuters can get to NYC and parts of Connecticut's Gold Coast in several ways. 

The Metro-North’s New Canaan line connects directly to Stamford, where folks can hop on a train towards New York City’s Grand Central Station or head east to New Haven. 

The Merritt Parkway, meanwhile, provides a convenient commute for drivers. Located on the south side of New Canaan, the Merritt connects directly to the Hutchinson Parkway, leading folks to the Bronx and parts of Manhattan and Queens. Plus, proximity to he I-95 is also an option but can get congested depending on the time of day. 

Quaint downtown 

With brick-faced facades and white trim, the buildings of Downtown New Canaan blend historical charm with a modern retail scene. Tree-lined Main Street is the centerpiece of this sizable part of town, from which smaller streets branch out to offer unique retail and dining options. 

Many locals head to Elm Street to check out high-end fashion at boutiques like Soleil Toile or shop for jewelry at places such as Pennyweights. When it comes to a quick bite between stores, many folks head to one of the many restaurants on Forest Street.

Downtown New Canaan has outlets for athletic shoes and bicycles, florists, and high-end antique shops. You can even find specialized stores like Goldenberry Coin, which trades in rare and valuable coins. 

Visual arts also have a strong presence here, on display at local galleries like Heather Gaudio Fine Art and Jean Jacobs Gallery. Silvermine Arts Center is another favorite, featuring paintings, sculptures, and contemporary installations. 

Fine dining 

Retail therapy may be one of its biggest highlights, but Downtown New Canaan also has an impressive selection of dining options. 

From quaint cafes serving artisanal coffee to fine dining establishments offering exquisite cuisine, the town's culinary experience can take weeks to explore. Folks looking for a fun brunch can head to Rosie, which offers farm-to-table fare and great libations. Just make sure to get here early to beat the rush. 

Those looking for an evening of fun dining should head to Tequila Mockingbird, famous for its Mexican cuisine and refreshing drinks. 

You'll want to visit The White Buffalo if you're looking for a nice pint after your post-work commute. The convenient location right across from the train station makes it easy to grab a drink before heading home. From unique cocktails like the spicy buffalo margarita to unique seasonal beers, there is a libation for you. 

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