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The view from Lloyd's Lane in Mattituck, where Douglas Elliman Real Estate holds this listing. Click the photo to see the listing.
The view from Lloyd’s Lane in Mattituck, where Douglas Elliman Real Estate holds this listing. Click the photo to see the house.

Scenario 1: It’s 8:28 p.m. and the sun is about to set on Long Island Sound. The waves come in … then go out … then come back in, lapping against the shore gently, yet loudly enough to still mimic the sound of the ocean. A mixture of soft blue and pink scatters the sky in a place far off in the northwest that, as you sit atop a 200-foot bluff, seems thousands of miles away. Yet Connecticut seems so close, you wonder how long it would take to kayak there.

Scenario 2: It’s early in the morning. Looking out at Peconic Bay, a body of water so synonymous with the region people have longed to name a county after it, you walk along the sandy beach occasionally glancing out at the Hamptons. Or maybe you’re looking out over one of the scores of creeks that dot Peconic Bay and spot an osprey swinging down to scoop up bunker. The weekday morning is quiet, but in a few days you may see several dozen boats out on the water in a single area, searching for porgies.

These two scenes offer a glimpse into what it means to live on one of the two bodies of water that surround the North Fork like a glove on a hand. 

The palm side, considered by many to be the more valuable, is Peconic Bay. On the outside — a little farther from the action, yet vital and valuable in its own right — is Long Island Sound.

As when purchasing gloves, one must decide which waterfront property on the North Fork is the better fit.

Tom Uhlinger of Douglas Elliman is quick to point to Long Island’s natural separation from Connecticut as one of the distinct features of the Sound side. That literal separation some 18,000 years ago created high bluffs and rocky beaches. So today’s Soundfront properties require bulkheading and long hikes down to the beach.

Because so many of the European settlers who came to the area beginning in the 1640s gravitated to the bay side, the Sound shore wasn’t developed until much later. This means lots along the Sound tend to be larger.

Most agents will tell you the battle of Soundfront vs. bayfront might not be exactly fair. Not all things are equal. It all depends on what you’re looking for.

“I never like to say ‘versus,’ ” says Corcoran agent Sheri Winter Clarry. “They both have different feels, so it doesn’t mean you can’t appreciate both. It’s more of what will suit your lifestyle better.”

A view from the Peconic Bay in South Jamesport. (Credit: Grant Parpan)
A view from the Peconic Bay in South Jamesport. (Credit: Grant Parpan)

Clarry, who has been selling homes on the North Fork for more than 20 years and recently represented the buyer in a $1.4 million sale in New Suffolk, encourages clients seeking waterfront homes to scope both areas out before getting too serious.

That’s exactly what Mike Osinski and his wife, Isabel, did before buying near Greenport Harbor. Now, the Osinskis run Widow’s Hole Oysters, which they started not long after purchasing their property in the early 2000s. For them, he said, the reasons for buying on the bay side were part personal preference, part natural.

“We don’t get those nasty nor’easter storms as much,” Osinski said. The property, tucked on the west side of Greenport Harbor, is “a little more protected.”

Asked to describe his view of the bay, he said: “Idyllic.”

“That comes up a lot,” he added. “Especially this time of year.”

Yet more than one real estate agent interviewed described the Sound side in a similar fashion, calling the sunsets there “dramatic.”

“A lot of customers really enjoy a good sunset,” said Lori Feilen of Town & Country Real Estate. She has recently sold bayside properties for $2.25 million and $1.8 million and one on the Sound for $1 million. Access to Long Island Sound can be a drawback, she said, especially for aging second-home owners who may want to walk along the water or take a dip.

Mr. Uhlinger, an agent for the past 21 years, estimates that properties on Peconic Bay sell, on average, for 15 percent more than a similar house on the Sound side. However, lots are generally larger on the Sound side and it’s difficult to find an apples to apples comparison between the two locations. He recently represented a Soundfront buyer in a $4.5 million deal, he said.

Easy access to boating and beaches — sandier ones, at that — are generally cited as the main reason the bay is considered a little more luxurious.

But that’s only if the glove fits you.