An Agent’s Guide for Where to Park Your Yacht

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75 Cliff Drive in Sag Harbor, listed recently for $4.395 million by Douglas Elliman agents Jonathan Davis and John Giruzzi.

The captain’s seat on the South Ferry is like home for Jon Westervelt, where he’s made nine trips a day across the channel for the past 40 years.

Every summer, like clockwork, he can almost feel them coming — the sailboats, the powerboats, the yachts.

And they only get bigger. And bigger. And bigger.

“These days, it’s not uncommon to see a 160-foot or 180-foot yacht come through the ferry channel, and that’s a big yacht,” he said, just after docking the ferry one recent afternoon. “A lot of times, they have helicopters on the back, they have cars on the back of them. It’s real wealth coming through here. It’s the über-rich. Just take a ride into Sag Harbor, have a cup of coffee and walk down the waterfront there. You’ll see what I mean. It looks like Palm Beach after Memorial Day.”

In the boating-saturated culture of the Hamptons, waterfront properties with deepwater docks are prime real estate, and in high demand, explained Westervelt, who is also a real estate agent for Georgiana B. Ketcham, Licensed Real Estate Broker — a sentiment widely echoed by his comrades across the East End.

“If people can afford it, they come out here for the water. Waterfront is golden, and it holds its value,” said Andrea Ackerman, a licensed associate real estate broker for Brown Harris Stevens. “We have a decent amount of inventory. But, of course, it’s limited because waterfront is limited, and dock permits are limited, and so a dock just adds value — real value — to a property. You’re not just getting a view. You’re getting the ability to dock a boat if you want to.

“I have found a lot of my waterfront buyers may not even own a boat, but plan on getting one if they buy the property.”

A waterfront property without a dock can be a deal breaker for many boat owners, explained James Keogh of Douglas Elliman, whose nearly $3 million listing at 139 North Ram Island Drive on Shelter Island is currently dock-less, but has the potential for one.

“You can have a mooring, which could probably get a 50-foot boat, and we’ve looked into adding a dock and it should be doable,” he said. “The access from the property, you could really be anywhere in the Hamptons very quickly — and the North Fork, as well.”

15 Mashomuck Drive in North Haven, listed by Mala Sander of Corcoran for $9.25 million.

The dock permitting process is one that can take years, and real estate agents are often quick to apply before the home is even sold — as is the case with 15 Mashomuck Drive in North Haven, listed for $9.25 million with associate broker Mala Sander of Corcoran.

Even without the dock, the house stands on its own, she said.

“It’s a one-of-a-kind experience. It feels like you’re on a boat,” she said. “It’s all floor-to-ceiling glass, it’s all renovated, there’s nothing to do — and at this price point, there really is nothing else where you can have a dock. A dock is very appealing to people, obviously, because people want to be able to walk right out to their boat. We do have a couple of properties that are waterfront that are beautiful, but don’t have possibilities of docks. But if you’re a boater, that’s 70 percent of the equation out here.”

The deepwater dock at 75 Cliff Drive in Sag Harbor once housed a 32-foot Cobalt, as well as paddleboards and jet skis, recalled listing agent Jonathan Davis of Douglas Elliman — a nearly $4.4 million property nestled on a creek without a wake zone.

“It’s only 5-mile-an-hour no-wake once you go in through Baron’s Cove, so you can go fast with a jet-ski, tubing,” he said. “You really get to make the most out of your water sports there, and you have Long Beach, as well, and you can zoom over to Baron’s Cove on the boat for dinner and come back. You really check everything.”

While it’s impossible to pinpoint the exact value of a deepwater dock, Ackerman estimates “it could be millions.” Her three-bedroom traditional listing at 59 Glover Street in Sag Harbor is on the market for nearly $7.9 million, while a vacant 2.5-acre parcel on Noyac Road is asking just shy of $4 million — and both would fetch far less without deepwater docks already in place, she said.

“There are properties in North Haven, major properties that have been on the market for $16 million, $17 million. Without a dock, it diminishes their value tremendously,” she said. “Deepwater docks are for big boats, if one wants. That’s a whole other category. A dock on Sag Harbor Cove can probably accommodate a 30- to 36-foot boat, whereas a deepwater dock can accommodate a yacht.”

Inside 4 Little Ram Island Drive, listed for $5.545 million by Penelope Moore of Saunders & Associates.

The grandfathered, 125-foot, two-tier dock at 4 Little Ram Island Drive on Shelter Island is the definition of quintessential deepwater — with electric, water, upper and lower levels, and approximately 5 feet at low mean tide, according to listing agent Penelope Moore of Saunders & Associates. The property is currently on the market for just over $5.5 million.

“Five feet at low tide would accommodate a sailboat,” she said. “He’s also got room on the dock for four boats, and he has a mooring with more depth, and he’s got two levels, so you don’t have to bounce around and hop into your boat. You can actually step down and be below your boat. It’s very unique.”

More often than not, potential buyers are less interested in the home than they are in the dock, Moore explained.

“Boating is the number one thing. People who are boaters really want a body of water that fits their vessel, and they want the dock that fits their vessel,” she said. “Most people with a boat seem more open to doing something with a house that’s not exactly perfect to their needs, when the dock is.

“Shelter Island is known as one of the best places to have a dock out on the East End,” she added. “People who are inveterate sailors, who do sailboat racing throughout the world, you can ask them about Shelter Island and they know exactly how special it is. There are people on Shelter Island who go to England for major sailboat races and they keep their boats in Derring Harbor, in Coecles Harbor, so that seems to draw a lot of people — the boating aspect.”

31 Dickerson Drive, Shelter Island listed for $2.495 million by Jon Westervelt of Georgiana B. Ketcham Real Estate.

From the deepwater dock at 31B Dickerson Drive on Shelter Island, it’s about three minutes to open water, Westervelt said — a trip that comes with a contemporary three-bedroom home on 1 acre, and a $2.5 million price tag.

“The real estate market here over the last 40 years? You bet it’s changed. I wish I had a crystal ball, I’da bought a lot of it,” Westervelt said. “Things have evolved; the waterfront has changed. I had two listings I sold last year, one on West Neck Harbor for just over $4.5 million, and another on Coecles Harbor, a much older house that needed renovation, but it sold at land value at about $3.4 million.

“The waterfront values have exploded here,” he continued. “You see when people come over from the Hamptons — from Sag Harbor, East Hampton and Amagansett — and they’re finding they can buy a nice waterfront house for $5 million and they just sold theirs for eight or 10, so it feels like it’s a bargain. They buy older, little cottages and renovate them into big, beautiful houses, and then the boats coming through the ferry channel, they’re just getting bigger and bigger and bigger. It’s quite a circus out here.”

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