Westport, Connecticut: A New York City Suburb
Westport, Connecticut should have failed as a suburb. It's too far from New York, too close to less expensive towns, too small of a population to support the amenities, spread across too large of an area to have low taxes.
But it didn't fail. In fact, it thrived and became one of Connecticut's most admired towns. Residents have made it exceptional. The schools, the beaches, the food, the New England charm, the open vibe. It shouldn't work, but it does. Let me show you why.
Hi, my name's Charlie. Today I'll be your guide or your sherpa as my friend Tom calls me. Over the last decade, I've helped hundreds of families move here from all over the world. What I learned from them might surprise you. You'll want to stay tuned until the end because I'll share with you two resources that'll help you avoid the single biggest mistake that I'm seeing buyers make over and over again in this market.
Coastal Westport: Compo Beach and Longshore
We're going to start in coastal Westport.
It's a warm Saturday morning and you walk down to Compo Beach with a coffee in hand. The sand is dotted with families setting up umbrellas, kids chasing each other along the shore, and locals greeting one another. You take a seat on the bench, and the view stretches wide. Long Island Sound sparkling in front of you. Sailboats gliding in the distance.
You feel the rhythm of the town here. Parents are catching up while kids are in summer swim lessons. Pickle ball and tennis courts are alive with activity. On the baseball fields behind you, weekend leagues are warming up. You might even hear the thump of a basketball from the nearby courts. For many, this is the heartbeat of Westport, a place I'm sure you'll visit again and again.
But the experience doesn't end at the beach. You also have Longshore Club Park just moments from your front door. All town residents are welcome here. It's the kind of setting where business relationships naturally develop over a round of golf and where your family can enjoy tennis, swimming, and sailing without ever leaving town and without a membership.
You'll notice the homes here vary beautifully. From charming beach homes that feel like permanent vacation retreats to grand properties set a bit farther back from the beach. You might even find a rare opportunity on Hall Island where you can own one of about a dozen homes with direct water access. Or Compo Mill Cove. You'll have access to this hidden gem by crossing a private foot bridge. No cars.
If you like the idea of convenience paired with this same coastal charm, wait until you see what's up river.
Saugatuck: Food, Trains, and the River
It's a vibrant, convenient lifestyle. You can step off the train and walk to some of Westport's best restaurants right here in Saugatuck. The industrial buildings once supported the town's oyster industry. Now, this location is a true foodie destination.
You'll likely find your favorite spot for Italian, a classic pub, or an amazing canoli, all within a few blocks. My clients are always blown away by the food scene here. You just don't expect this level of dining in a town of this size.
If you're commuting into the city, this will likely be your hub. The main Westport train station is here with express service getting you to Grand Central in just over an hour.
You've got one of the world's best 9-hole golf courses over at Birwood Country Club. And if you're into boating, the Saugatuck Harbor Yacht Club is just minutes from here.
Saugatuck Shore and Saugatuck Island
If you love this location, but crave that coastal nautical style, that's when you'll want to head to Saugatuck Shore.
It's Friday afternoon and the city feels a million miles away. Should you paddle out to Kaini Island and relax on the beach or grill on the deck as you watch the sunset over the sound and hear the gentle tapping of the howiards in the background?
When you arrive on the peninsula of Saugatuck Shore, you'll immediately notice the coastal charm from the seashell line driveways to the kids building castles on the private community beaches. The peninsula is actually divided by a narrow canal creating two distinct sections. On one side is Saugatuck Shore. On the other side is Saugatuck Island.
Saugatuck Shore offers the tranquil Bermuda lagoon. It's one of the best and most protected places for a private dock in the entire Gold Coast. On Saugatuck Island, you'll find the Cedar Point Yacht Club, which is big into sailboat racing. During the riata season, you'll see them from the shore.
The views from these homes are breathtaking. To the east, you can see Canfield Island and Sprite Island with a cluster of Norwok Islands just beyond. To the south, Kaini Island beckons. A public island with a perfect crescentshaped beach that you can reach by kayak or boat. The best part, it feels like a vacation community, yet it's just minutes from downtown.
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Why Families Choose Westport
So, you've begun to explore the town and feel the different vibes, but what makes families choose Westport over all the other options? My clients tell me it comes down to a unique combination of factors that create something truly special.
First, Staples High School consistently ranks in the top five public high schools in Connecticut and holds the prestigious National Blue Ribbon School designation. With 27 AP courses in college acceptance rates that rival elite private schools, you're giving your children an education that will impact the rest of their lives.
In addition, Neighborhood Scout reports a violent crime rating nearly 22 times below the national median along with property crime rates about 40% lower. It's a piece of mind that you can't put a price on.
And then there's the cultural richness. This isn't just a bedroom community for New York. You have a longheld, thriving art scene right here. It's a place where your family can engage with culture right in your backyard.
Stack on the fact that Westport attracts many CEOs, financial professionals, and other executives, and for many of them, the tax savings alone can be substantial. And add that authentic New England coastal experience that's hard to find closer to the city, and you can see why Westport is a real winner for so many.
Our tour now continues in one of Westport's most upscale neighborhoods. Afterwards, I'll share with you two essential resources that'll help you sidestep the single biggest mistake I see buyers make in this market.
In-Town Westport
Next, let's explore what many consider the heart of Westport, the in town neighborhood.
This is the only place in the county where you'll find this level of high-end waterfront shopping. You can spend a day strolling past stores like Tiffany, Vineyard Vines, and William Sonoma, all in a historic setting along the Saguk River.
You can feel the vibrant, sophisticated energy here. It's a place to grab coffee, have a great meal, meet friends, and browse the boutiques, but it's also a cultural hub. You have the award-winning Westport Public Library, the renowned Westport Country Playhouse, and the Levit Pavilion, which hosts free concerts all summer long.
Many of my clients who crave a walkable environment explore here. You'll find homes just north of Main Street, where you can walk to just about everything. Or if you prefer a more suburban feel with a larger lot, you can find that too, less than a 5-minute drive away.
If you want to be at the center of it all with worldclass shopping, dining, and culture right outside your door, the in town neighborhood might be for you.
Greens Farms
Next, we're going to head east to the neighborhood of Greens Farms. You can feel the history here. It's one of the oldest and most sought-after parts of town.
The landscape is defined by majestic trees, stone walls, and a sense of New England charm. This is where you'll find some of Westport's most magnificent waterfront estates. You can see yourself looking out from one of these homes over an expansive lawn past a private sandy beach with completely unobstructed views across the Long Island Sound. It's a feeling of tranquility and prestige that's unmatched.
Even if you're not directly on the water, you'll appreciate the convenience of this neighborhood. You have the charming and historic village of Southport nearby and your own train station getting you to Grand Central in about 10 extra minutes when compared to the Westport station.
And for a more intimate beach day, you can head to Barying Hill Beach, a smaller residentonly spot that rarely feels crowded. If you're looking for a timeless, elegant neighborhood that combines stunning coastal beauty with a statelike privacy, Greens Farms is an essential stop.
Old Hill
Just across the river from the bustling in town neighborhood, you'll find the quiet scenic neighborhood of Old Hill. Here there are new builds and stately historic homes on the peaceful treeline roads.
The appeal here is the effortless balance between privacy and proximity. You can live on a quiet street, perhaps in a home overlooking the serene Nash's Pond, yet you're only a minute or two from the high-end shopping and dining in town.
The neighborhood is also home to Earthplace, a 62 acre wildlife sanctuary. It's the perfect spot to take your kids for a hike on the trails and let them connect with nature.
If you appreciate the charm of historic architecture and the convenience of being close to town, but want a more peaceful residential setting, Oldill provides that perfect blend.
Hunt Club and Long Lots
Just a short drive from the center of town, you'll find the Hunt Club and Long Lots neighborhoods. This is an area many families are drawn to because of the schools. Staples High School and Bedford Middle School are located here, and their proximity makes school drop offs and pickups incredibly convenient.
You'll notice a classic suburban feel with beautiful homes on well manicured lots. The Hunt Club is a centerpiece of the community, offering equestrian facilities, tennis, and social activities.
You also have fantastic amenities nearby, including Wakeman Town Farm and Agricultural Center, where you can buy fresh local produce. If your priority is easy access for school pickups in a convenient suburban setting, this area is often the perfect fit.
Northern Westport: Coleytown and Red Coat
So, I'm curious, what's the one thing you still want to know more about? Is it the schools, the commute, or something else entirely? Let me know in the comments what you'd like to see next.
As we head to the northern part of town, you'll enter the neighborhoods of Kolitown and Red Coat. Crossing the Merit Parkway, you'll feel a distinct shift. The landscape opens up, and the atmosphere becomes more rural and peaceful.
This is where you come for privacy and space. It's a tranquil, park-like setting that feels completely removed from the bustle of town, yet you're still only a 10-minute drive from stores along Post Road. You can spend your weekend stargazing at the Westport Astronomical Society or enjoying the quiet of your own backyard.
If your dream is a magnificent home with unparalleled privacy surrounded by natural beauty, you'll find it here in the northern part of Westport.
Avoiding the Biggest Buying Mistake
So, you've just scraped the surface, and it's easy to make the most common mistake, choosing the right house in the wrong area for your daily life.
I have two resources to help you find the perfect place.
- If you're the type of person who likes to gather all the information first, my website is where I've organized all my videos, maps, and custom home searches to make your search easier.
- But if you feel a conversation with me would be more valuable, I'd love to chat, answer your questions, and help you connect the dots.
So, what's best for you? Should you go over to the website and grab all those resources, or give me a call? Either way, I've got your next step covered.