Everything You Need to Know About Moving to Westport

Everything You Need to Know About Moving to Westport

Welcome to Westport, Connecticut. A quaint little town situated on the coast of Connecticut’s Gold Coast. With its charming seaside cottages and modern beach homes, a mix of traditional New England lifestyle, and plenty of spillover culture from New York City just 40 miles away, Westport is a rare suburban find. Read on to learn more about moving to Westport with coastal vibes on your mind, including the lifestyle, neighborhoods, restaurants, activities, transportation, and cost of living. Perhaps you’ll discover that moving to Westport is the next best move for you!


Relaxed coastal vibe

What sets Westport apart from other Connecticut towns? Simple: it offers a relaxed coastal lifestyle not found elsewhere in the state. Steeped in history, and once known as an artist’s community, there is an emphasis on living life to its fullest in Westport, especially on the weekends – take a morning walk along the water, hit the town for outdoor dining and upscale shopping, have an afternoon paddle board or boat ride, then lounge on the deck with a good drink or two and share in the relaxation with your family and friends.

Residents enjoy access to a number of beaches along the Long Island Sound. With Compo Beach being a hub of the town social scene, there is also Old Mill Beach, Burying Hill Beach, and Sherwood Island and while not a beach, Longshore Club Park is set on the Sound and offers plenty of outdoor activities – golf, tennis, sailing, kayaking, (ice skating in the winter!) — there’s always something to do.

Water centric neighborhoods

For the best water and beach neighborhoods, consider checking out one of these.

Compo Beach

Compo Beach is a wildly popular beach neighborhood that offers its residents stunning views of the shore. This neighborhood is small, walkable, and highly exclusive, desired for its quick and easy access to the popular beach of the same name.  There is a marina, snack bar, plenty of green space, and outdoor fun like pickleball and grilling areas.

Saugatuck Island and Saugatuck Shores

One of the most luxurious and peaceful neighborhoods in all of Westport, Saugatuck Shores offers a wonderful array of boating and beach life. The island offers many homes with private docks, and oh, it's just a hop skip and a jump from the Westport Train Station!

Old Mill Beach + Compo Mill Cove

The homes set on the hill overlooking Old Mill Beach bring all the California vibes. While its pure New England summer on the pedestrian-only island of Compo Mill Cove, a small enclave of home accessible only by footbridge and surrounded by the gorgeous Sherwood Millpond and Long Island Sound.

Restaurants and cafes

Westport is home to a rich foodie culture of its own thanks to its proximity to New York City. Here are just a few favorites to visit and take in the water views.

The Whelk

The Whelk is the premier destination for sustainable food and locally sourced produce. You may enjoy your meal within the restaurant, or bask in the pleasant weather with their outdoor seating.

Rive Bistro

Rive Bistro is a riverfront bistro offering classic French dishes and brunch in a comfortable, welcoming setting. Indulge your taste buds while relaxing beside the Saugatuck River.

Old Mill Grocery

Old Mill Grocery is an institution near the beach of the same name.  The cute little beach shack offers a wide variety of sandwiches, salads, coffee, smoothies, and grab-and-go items like fresh flowers! It’s a perfect stop for a quick lunch or dinner by the water.

Things to do

Aside from beach days, there are plenty of other activities to enjoy in Westport. Here are just three out of hundreds of activities perfect for you and your family.


The Earthplace is a non-profit organization dedicated to the study and sustainability of the natural world. Guests are welcome to learn and hike the trails at their leisure.

Westport Museum for History and Culture

The Westport Museum for History and Culture is a cultural museum that houses various tidbits of American history and unique aspects of American culture. It also hosts summer camps and other seasonal events.

Westport Observatory

The Westport Observatory is operated by the Westport Astronomical Society, devoted to the study of the sky and the universe we live in. It sits on the highest elevation in the town and invites guests to learn with them.


Proximity to New York City

One of the advantages of living in Westport is the town’s proximity to New York City. The town is intersected by Interstate 95 and the Merritt Parkway, granting residents an easy path to New York City by car. The Grand Central Terminal is another transportation option as well if you’d rather unwind during the commute. Trains to and from the terminal are about an hour long both ways.
To learn more about moving to Westport and looking for Westport homes for sale, reach out to The Leslie Clarke Team. With over 40 years of combined sales experience, Leslie Clarke and Jeannette Floto are the teams to help you find the Westport home of your dreams. Let’s start a conversation today!

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