Extraordinary Estates

Our shores are practically bursting with beautiful homes. To limit our annual composite of the most extraordinary to just five is an exercise in restraint as much as it is anything else. We asked around, scouring the seasides and bay fronts and everywhere in between in search of unique expressions of style and charm. From Great Neck to Greenport, Long Beach to Montauk, our list crisscrossed the Island. Then we deliberated over our favorites—this home’s kitchen versus another’s pool—until the list was a handsome collection of the brightest, presented on the following pages.

This Gold Coast habitat is situated near one of the cultural hubs of Long Island. The Tilles Center for the Performing Arts is less than two miles away. This affluent burb is also ideal for a NYC commuter who wants to keep the family in lavish style. Brookville is one of the wealthiest towns in America and one of the most private—it has no commercial development, no public parking and few sidewalks. It does have plenty of country clubs though (three within village limits, two bordering).

Following suit, this traditional six-bedroom cedar-shingled colonial was designed to ensure comfort, luxury and seclusion. Architectural millwork and Brazilian walnut wood floors add warmth and style throughout. The real stunner in this home is the bespoke kitchen: Stainless-steel farmhouse sink, high-end fridge and appliances hidden behind ornate wood scrollwork, and a recessed stove hood bookended by decorative corbels, for instance. In other words, a gourmand’s dream kitchen. This breathtaking two-acre setting also comes with five fireplaces a bluestone patio, recreation room, master study, three-car garage and sparkling in-ground saltwater gunite pool and spa.

List price: $3.9 million |
Taxes: $51,776
Style: Colonial
Year built: 2003 | Rooms: 14
Bedrooms: 6
Bathrooms: 6 1/2 Lot size: 2 acres
Listing agency: Daniel Gale Sotheby’s International Realty

Lloyd Harbor
Long and squat between the shores of Cold Spring Harbor and Huntington Harbor sits this estate. It’s a study in rustic ambience, fully embracing Lloyd Harbor’s commitment to seclusion and preservation. The community has a long history, dating back to 1926, of enacting ordinances to maintain its natural beauty and privacy. The area is an outdoorsman’s dream: Hundreds of acres of undeveloped land, two parks, a nature preserve, rolling hills and dense woods.

Pulpit Rock is a one-of-kind traditional French Provincial estate that is both bucolic and grand. Clad in brick with a slate roof, copper gutters and gracefully arched windows, it’s the picture of countryside chic. Step inside the soaring entry hall where warm wood tones, from the herringbone hardwood flooring beneath to the darker mahogany moldings above, keep the feel formal. Here a grand staircase allows anyone to make a fashionable entrance, perhaps after reading a book in the upstairs library with built-in seating. The two-toned wood theme continues in the kitchen with custom cabinetry and intricate scrollwork but its mood is lighter, thanks to a bank of windows. Out back the mahogany deck feels warm (and lavish) too, while the heated gunite pool offers a different kind of coziness.

List price: $3.5 million
Taxes: $41,468
Style: Traditional
Year built: 1976
Rooms: 10
Bedrooms: 5
Bathrooms: 5
Lot size: 2 acres
Listing agency: Daniel Gale Sotheby’s International Realty

Situated in the enchantingly quaint Salt Lake Village, this is a charming North Fork home that displays tranquil views of Great Peconic Bay where it meets James Creek. The abode is just steps from a sandy beach and water views that stretch across to the Hamptons. It’s within easy walking distance of local restaurants and bars, a coffeehouse, a grocery store and a district park on the decidedly laid back fork.

The views shine through palladium windows in the spacious master bedroom with shaded deck. Built for water sport enthusiasts who can enjoy the view from starboard side, this modern waterfront gem not only includes boat docking rights, but is just a short trip from a boater’s paradise. Peconic Bay’s calm waters in summer and fresh sou’westers in late afternoon have made it an upscale vacation area ideal for sailing and showing off new toys. After a day of beach activity, retire for a bite in the well-appointed kitchen/dining area, which sports modern, high-end stainless-steel appliances. An inviting counter-height fireplace set into the wall really ties it all together and is a great way to relax weary, sun-soaked bodies at the end of the day.

List Price: $2.7 million
Taxes: $21,182
Style: Colonial
Year Built: 2006
Rooms: 9
Bedrooms: 3
Bathrooms: 3
Lot Size: .35 acres
Listing Agency: Daniel Gale Sotheby’s International Realty

Sands Point
This Gatbsy-era Dutch colonial is nestled on some of Long Island’s most treasured waterfront. The area has a wealthy lineage that dates back to the Sands, Vanderbilts and Cornwells who once resided here. Out back there’s a private dock for a boat—a must when owning a home on the sound. The property is ideal for those who want to ensconce themselves in Gold Coast opulence with a healthy dose of privacy. The views of the Manhattan skyline and costal Connecticut make a tony backdrop when entertaining inside or on the lawn.

Meticulously restored in 1997, Bay Winds is set on the cloistered peninsula of Plum Beach Point with 300 feet of shoreline and sandy beach. Step into the inviting two-story foyer and let the warmth of the hardwood flooring, traditional wainscoting and crown molding carry you through the spacious hallway to the formal banquet-style dining room. The estate’s six bedrooms and nine baths can handle a small army of overnight guests and the outdoor amenities can entertain many more during the day—a rear brick patio wraps around an in-ground pool with plenty of lawn space for a game of croquet or bocce. Inside, French doors open to complementing patios, porches and balconies.

List price: $10 million
Taxes: $84,225
Style: Dutch colonial
Year built: 1926
Rooms: 12
Bedrooms: 6
Bathrooms: 7 full, 2 half
Lot size: 1.5 acres
Listing agency: Douglas Elliman Real Estate

South of Montauk Highway along the Speonk River sits an elegant yet unpretentious estate. With access to Dune Road on the barrier island, shopping and restaurants, the house offers all the best of casual Hamptons living. The calming colors inside immediately melt away the stresses of the workweek, and the yoga studio doesn’t hurt either. A home like this makes a weekend slip seamlessly into an impromptu three day-long mini vacation.

This estate’s most stunning feature is its saltwater infinity pool and Jacuzzi adjoining verdant lawns that abut a picturesque river. Local East End architect Nick Vero designed this 6,500-square-foot post-modern gem, which sits on 2 acres of lush waterside property offering sun-filled respite and entertainment. Two patios perfectly situated for lounging and soaking in the sun or late-night gatherings rim the space. Adjourn to the game room decked with dark hardwood floors and corner bar and enjoy a spirited game of billiards. Retire to the spacious living room sure to stir rousing conversation in front of the floor-to-ceiling rustic brick fireplace. Feeling peckish? Linger over a snack in the huge gourmet kitchen with gathering room and floor-to-ceiling window-lined walls displaying views of the back pool area. A separate carriage house with guest quarters makes this a dream home for entertaining and relaxation.

List price: $3.8 million
Taxes: $18,735
Style: Postmodern
Year built: 2004
Rooms: 10
Bedrooms: 5
Bathrooms: 4 1/2
Lot size: 2 acres
Listing agency: Douglas Elliman Real Estate