FROM MANHATTAN TO MARITIME

I wasn’t just looking at a beautiful piece of real estate. I was experiencing something New Yorkers rarely admit they need: the ability to exhale. A true pause. The kind that sticks.

The island itself is 2.3 acres, and feels like a secret passed between generations. Listed at $2.9 million, Wayland isn’t just a home—it’s a compound, a memory-maker, and for someone like me, a revelation. I didn’t expect to fall for it. But that’s how the best love stories begin, isn’t it? 

What an Island Feels Like This place doesn’t open with grandeur—it unfolds. The approach is simple: a private dock, some granite ledges, trees swaying in rhythm with the tide. It’s not showy. It’s subtle. Intentional. The kind of beauty that doesn’t need an introduction. The moment your feet touch the dock, your shoulders drop. And that familiar New York tension? Gone. 

What an Island Feels Like
This place doesn’t open with grandeur—it unfolds. The approach is simple: a private dock, some granite ledges, trees swaying in rhythm with the tide. It’s not showy. It’s subtle. Intentional. The kind of beauty that doesn’t need an introduction. The moment your feet touch the dock, your shoulders drop. And that familiar New York tension? Gone. 

As someone who thrives on adrenaline—deadlines, interviews, boardrooms—Wayland offered me something foreign: peace without loneliness. Space without disconnection. I stood at the edge of the wraparound porch, looked out at the Sound, and for the first time in a long while, didn’t think about my phone.

More Than One Home
There are three houses on the island, each with its own soul. One is a 1900s Victorian—complete with porches, gables, and fireplaces that practically beg you to curl up with a glass of red and a great book. The others feel more laid back—think guest quarters, creative spaces, even a perfect setup for multi-generational living. 

In total, there are 14 bedrooms and seven baths spread over more than 6,000 square feet. That’s not a typo. Fourteen bedrooms. You could host a family reunion and still find a quiet corner to write your memoir. Or not speak to anyone until the second day.  

As I walked through each house, I wasn’t thinking in square footage or comps—I was picturing birthdays. Holiday dinners. Long weekends with friends who’ve become family. This isn’t a showplace for Instagram. This is where your kids and grandkids come to know your stories. Where traditions start. 

 

The Magic of the Everyday
The interiors aren’t overdone. They’re authentic. Hardwood floors, built-ins, exposed beams, working fireplaces. Everything whispers of time and presence. There are windows in every room—some small, some panoramic—all framing water like living art.

You won’t find central air here, or climate-controlled wine cellars. You will find sea breezes, propane heat, outdoor showers, and mornings that smell like salt and sunshine. There’s public water and septic. Reliable. Simple. It reminded me of summers in Montauk when it was still a secret. Before things got complicated. 

I took my coffee out to the deck and watched a heron fish off the rocks. The wind pushed ripples across the surface like a painter’s brush. I sat there longer than I usually allow myself to sit anywhere. It wasn’t until I went back inside that I realized—this was what I’d been looking for.  

I took my coffee out to the deck and watched a heron fish off the rocks. The wind pushed ripples across the surface like a painter’s brush. I sat there longer than I usually allow myself to sit anywhere. It wasn’t until I went back inside that I realized—this was what I’d been looking for.

The Thimble Islands: The East End Without the Ego The Thimble Islands are legendary among those in the know—rugged, small, dotted with homes that aren’t easy to access and don’t come on the market often. Rogers Island, Money Island, Pot Island... all iconic in their own way. But Wayland, Little Pumpkin, is different. It’s less about prestige, more about peace. 

I thought about that as I walked the grounds. What would it feel like to bring your child here every summer? To teach them how to fish off the dock? To read bedtime stories under a sky not competing with city lights?  

That’s the thing about islands: they don’t just change your pace. They change your priorities.  

Less Than Two Hours from Midtown From Manhattan, it’s under two hours by car or train to Branford. From there, it’s a ten-minute ride by boat. That means you can leave the office on Friday afternoon and be grilling on your island by sunset. 

Less Than Two Hours from Midtown
From Manhattan, it’s under two hours by car or train to Branford. From there, it’s a ten-minute ride by boat. That means you can leave the office on Friday afternoon and be grilling on your island by sunset. 

For the New Yorker Who’s Ready Wayland Island isn’t for everyone. And that’s exactly why it’s so special. It’s for someone who doesn’t need to be seen to feel successful. Someone who’s measured life in deadlines and now wants to measure it in tides.  

For the New Yorker Who’s Ready
Wayland Island isn’t for everyone. And that’s exactly why it’s so special. It’s for someone who doesn’t need to be seen to feel successful. Someone who’s measured life in deadlines and now wants to measure it in tides.