Top Towns on the Long Island Sound

Though the Hamptons is one of Long Island’s most known getaways, don’t overlook what the north side of the island has to offer. Tucked along the coastline of the North Shore and North Fork are just as picturesque towns that have stood the test of time and retained their quaint, small-town charm. Discover these spots along the Gold Coast and beyond that deliver on spectacular vistas, prime relaxation and stunning homes.

Cutchogue
5775 Nassau Point Rd LI sound towns

Called the Sunniest Hamlet in New York, Cutchogue overlooks the Long Island Sound and Connecticut and is known for its magnificent sunsets. Farms and vineyards are plentiful as well as boutique shops like Bloomstrings or delicious restaurants like Touch of Venice.

“Working in Cutchogue is a joy. You are surrounded by beauty, no matter the season,” said agent Karla Dennehy who has worked in the area for 10 years. Enjoy the bucolic surroundings by partaking in the plethora of available outdoor activities like sailing, kayaking or relaxing on the beach.

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Greenport
51 54th St LI sound towns

This charming seaside village has beautiful antique homes and unparalleled waterfront charm. Enjoy stunning views of the harbor from Mitchell Park as you watch the boats come in or walk along Front or Main Streets to enjoy the enchanting small-town charm of whimsical boutiques like Not Just Bows and Goldsmith’s Toys and Electronics. You can also nosh on contemporary eats at Noah’s while you enjoy a table outside or sip a luxurious glass of wine at Kontokosta Winery that overlooks the Sound.

“The streets are a grid like a tiny city, and when the season is in full swing it’s a very lively town,” said Douglas Elliman agent and Greenport native Paul Loeb. “There is truly something for everyone in Greenport.”

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Northport
117 Asharoken Avenue LI sound towns

Agent Kelley Taylor has called Northport home for 23 years, and instantly knew it was the place for her. “When I drove down Main Street Northport for the first time, I knew I was home.”

The beautiful Gold Coast town has everything from a brewery to restaurants to a theater, making it the perfect place that’s quiet and removed from the hustle and bustle of Route 25A, the main artery of the North Fork.

Transport yourself through time along Main Street, where you can stroll along the trolley tracks that lead down to the harbor and take in stunning sunsets over the Long Island Sound. Sit along the dock and in the park to watch the boat traffic or relax, read a book and enjoy the scenery for a peaceful and unbeatable evening.

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Nissequogue
468 River Road LI sound towns

This bucolic area is the eastern-most point of the Gold Coast. Made famous by architect Stanford White who owned a grand country estate in the area, Nissequogue and sister village Head of the Harbor feature spectacular mansions and distinct architecture developed by White and his contemporaries during the Gilded Age.

Only 50 miles east of New York City, Nissequogue is an appealing alternative to the Hamptons for peak relaxation and laid back attitude. Visit one of the fabulous nearby restaurants, or for a special meal head to Harmony Vineyards for brunch and explore their tasting room, circa 1690, to step back in time. If you’d prefer to enjoy the outdoors, the Village has a golf and tennis club, beach club, yacht club and marina. There are also two public beaches and a river where you can canoe, kayak or fish alongside nature preserves perfect for hiking.

“Nissequogue is a year-round community that’s structured for enjoyment in all four seasons,” said agents Mickey Conlon and Tom Postilio. “Time seems to slow down here. With all the stressful demands of the daily grind, it’s nice to wind back the clock a bit and add punctuation to life.”

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