On the Market: 9 Properties That are the Perfect North Shore Escape

Long Island’s well-known North Shore has long been a destination for those looking to escape the city, but who still want to live just a train ride away. With its beaches, lush landscapes, vineyards and more, Long Island has much to offer. These waterfront properties on the North Shore provide just the right blend of privacy, connection to nature and old-world splendor. From the Village of Nissequogue to Manhasset, the choice of neighborhoods are endless for your next sweeping estate.


2 Wallis Lane, NIssequogue, NY | $14,600,000 | Agent: Tom Postilio, Mickey Conlon

Inspired by the Governor’s Palace in Williamsburg, Virginia, this notable estate was completed in 1935 and remains a crown jewel of Long Island’s fabled North Shore. Commanding nearly 15 level, waterfront acres overlooking Long Island Sound, Somerset enjoys an unassuming approach that leads to the end of a long, private road adjacent to the lush David Weld Sanctuary; a tranquil, wooded nature preserve. The property, with its specimen plantings and exceptional privacy, boasts a staggering span of nearly 900-feet of unobstructed waterfrontage (just shy the equivalent of three football fields) along the shoreline, the toe of which has been fortified by a newly constructed seawall of steel and stone. The unparalleled views of Smithtown Bay and Long Island Sound defy description, literary or artistic, though Daniel Webster liked to call the Sound, “our American Mediterranean.” Recently heralded as a mellower Hamptons by The New York Times, the Village of Nissequogue, just 50 miles east of Manhattan, affords its residents a quiet escape that includes two private beaches, a private golf and ?tennis club, multiple equestrian facilities, hiking trials, vineyards, and dedicated Village police and fire departments. Showings by private appointment only.

95 Lake Road, Manhasset, NY | $11,800,000 | Agent: Maria Babaev

While paying homage to its “Great Gatsby Era” opulent origins, this home has been thoroughly updated with Twenty-First-Century comfort and state-of-the-art amenities. Today, the fourteen-room estate includes the largest private dock in Manhasset Harbor and a private beach and guest house. The main house includes walls of glass windows and doors throughout with an indoor heated pool and spa, a ballroom-sized “club room” with stone fireplace, and multiple patios and decks. Known as “The Whitney Boathouse” this fully-renovated masterpiece was the former weekend retreat of John Hay “Jock” Whitney. It was originally built in 1910 by William Payne Whitney, tycoon and philanthropist, as a gift to his son, to serve as a dock and hanger for his 40-foot seaplane.

200 Sunset Cove, Oyster Bay Cove, NY | $8,100,000 | Agents: Regina Rogers, Jyll Kata

Designed by Kimball Husted and built in 1937, this estate was purchased in 1950 by George O’Neill and his wife, Abby Rockefeller O’Neill, great granddaughter of John D. Rockefeller, for nearly seventy years. It is set on a magnificent and rare 31.5 acres with a delightful range of vistas from woodland to sweeping lawns and gardens. At the end of a scenic drive, a spacious circular courtyard welcomes you to this stately eleven-bedroom, seven-and-a-half-bath, Georgian brick manor. To the left, a service courtyard provides access to three garages, totaling nine bays, and a two-bedroom guest cottage. To the right in the distance, hidden by Japanese maples, an in-ground gunite pool with bluestone patio, babbling rock waterfall, and pool house stands ready for an afternoon swim. The interiors offer high ceilings rimmed by intricate crown molding and lustrous hardwood floors. French doors with transom lights open to two loggias and several bluestone patios, and tall mahogany doors beneath frieze entablatures, a bridal staircase, oversized windows,  and six inviting fireplaces are just part of this homes enduring charm. A lovely reception hall, ballroom sized living room, banquet-sized dining room, and study were designed for grand year-round entertaining – all with easy access to the grounds and serviced from a wing with butlers pantry, kitchen, laundry, back stairs, and cooks quarters. Extensive accommodations for family, guests, and staff can be found on the second floor as can the palatial and romantic master suite.

401 Centre Island Rd, Centre Island, NY | $8,995,000 | Agent: Regina Rogers

This Centre Island waterfront property, offers direct, private beach front, a guest cottage, 100-foot deep-water dock, three-car garage, in-ground gunite pool with spa and cabana, tennis court, and greenhouse, plus formal, cutting, and cooks gardens set on 9.54 acres. Sized for grand year-round entertaining and designed for guests’ comfort, the 10,000 foot manor house features 11 bedrooms 7 full baths and 4 half baths along with gracious living spaces including a gracious two-story foyer with twin floating staircases, expansive bluestone patios, regal living and dining rooms, a delightful spacious solarium, a cozy library and more.

107 Lake Road, Manhasset, NY | $7,298,000 | Agents: Traci Clinton & Lorraine (Lori) Downey

Step inside this sun-drenched Hamptons style showplace which offers stunning architectural details & finishes that sets a new standard for luxury No detail has been missed in this newly completely rebuilt & expanded 6 bedroom, 6.5 bath residence with its own private sandy beach on 1.32 acres of prime Manhasset Bay waterfront. Imagine breathtaking sunsets with panoramic vistas from any of the gorgeous principal entertaining spaces. Be mesmerized by the property which is truly a tranquil retreat offering a 22 x 42 heated in-ground salt water pool & spa, a summer kitchen, multiple terraces including one w a cozy outdoor fireplace This custom state of the art smart home offers 11 zones of radiant heat, 5 fireplaces, newly built 250 ft dock & stone sea wall, 10 ft plus ceilings, sonos sound sytem water filtration system, Central Air Conditioning, Security System w cameras, bespoke cabinetry, a true gourmet kitchen with a La Cornue Range & much more. Over 7800 sq. ft of luxury on 3 open levels.

6 Wincoma Drive, Huntington Bay, NY | $7,000,000 | Agents: Risa Ziegler, Jyll Kata

With a spectacular approach, this outstanding exclusive waterfront home sits on an unparalleled 2.25-acre property with 200’ of waterfront and priceless views.  A Cobblestone motor court leads to a glorious 2-story entry, and the home offers a superbly scaled eat-in kitchen, dining room, family room, and sunroom, all w/direct water views. There is also a double en-suite main bedroom with 2 en-suite bathrooms, a private sitting room, fireplace, balcony & full 360 water views. Three additional en suite bedrooms offer balconies and water views. On the grounds, there is a perfect 2-bedroom guest cottage  cottage with bull bath, and in-ground heated pool, cabana, putting green and three-car garage. Wincoma Beach Association with deeded beach and mooring rights-due required.

5 Bouton Point, Lloyd Harbor, NY | $6,750,000 | Agent: Maria Babaev

Come experience the quintessence of luxury Gold Coast living in this sumptuous, brand new waterfront haven on the eastern shore of Lloyd Harbor, with 400-feet of shoreline, deeded dock rights, convenient to golf, equestrian and cross country ski trails, and the thriving shopping districts of both Huntington and Cold Spring Harbor villages. Known as Villa Marina, this magnificent new Mediterranean villa, designed by Granoff Architects, sits on a breathtaking 2-acre property, located at the entrance of Huntington Harbor and offering panoramic vistas of Huntington Bay with the Huntington Harbor Light house twinkling in the distance.

44 Crane Neck Rd, Old Field, NY | $5,999,000 | Agent: Maria Orlandi

Located on the Gold Coast of Long Island in the village of Old Field, on over 7 acres of waterfront property with beach rights to a private beach, this luxurious Mediterranean-inspired estate is perfectly poised for outdoor living with lush landscaping, verandas, a gunite pool, and stone patios. The home offers well-proportioned rooms that are grand in scale and airy with beautiful outdoor light streaming through walls of windows and French doors. With custom millwork throughout,  there are many dramatic elements, décor and details including an elegant dual story entry foyer with marble floors, a breathtaking great room with high ceilings and stunning waterviews, a spacious gourmet granite kitchen with beautiful Tuscan accents, six bedrooms, 7.2 bathrooms, a full basement, wine cellar and gym.

Find your next home on Long Island’s North Shore today.

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