Top 5 Most Expensive Homes in Southampton

Waterfront. World class. Some of the most luxurious, most expensive homes money can buy are in Southampton—and the Top 5 are right here.

160 Ox Pasture, Southampton, $49,000,000

This Southampton Luxury estate by architect Grosvenor Atterbury was originally built in 1915. It has been lovingly restored during a three and one half year renovation to its original grandeur. No expense was spared as the finest of design and construction were executed during this complete overhaul and refitting. Luxurious interiors boast intimate elegant rooms, many with fireplaces, for the most discriminating buyer desiring a residence with the finest of details and comfort. The gracious floor plan spans nearly 18,000 sq. ft. within this beautiful comfortable Southampton Village country home. The grand entry hall leads to the main living room with leaded glass doors overlooking 9.11 acres of incredible landscaping. Old trees, flowering shrubs, evergreen perimeters, rose gardens, just a few of the garden tour features of this property. Private resort-like amenities include fantastic indoor pool, outdoor pool with pavilion, tennis court, paddle court, gymnasium, carriage house, 4-car garage and too many more to mention. A unique opportunity to own an historical world class residence in the prime estate sections of Southampton.

2. World Class Oceanfront, Southampton, $34,000,000

Listed with Tim Davis of Corcoran. This exceptional residence in pristine condition and perfectly sited on nearly 4 acres of shimmering dunes and white sand beach. Beautiful interiors designed by renowned Bunny Williams boast high ceilings and walls of glass opening out to protected views of the Atlantic Ocean and Shinnecock Bay. This very special home offers the finest in luxury lifestyle living spanning approximately 8600 sq. ft. Outdoors invites the sun lover to swim in the Oceanside pool and dip in one of two hot tubs, there is also a championship tennis court which is in excellent condition. This is A great home for seaside living and entertaining. Conveniently located with access to New York City and International airports. Available for immediate occupancy.

3. 385 Great Plains Road, Southampton, $30,000,000

Listed with the Breitenbach team with Corcoran, This is one of the most admired homes in the Southampton Estate area with 3.4 acres in prime location. Unparalleled custom one-of-a-kind construction with 10 fireplaces, imported French fireplace mantles including an amazing master suite with paneled sitting room, fireplace and built-in cabinetry, circular tower alcove, outdoor deck, and antique French tub. Hand-painted walls in master suite, entrance all and powder rooms by American painter, Kevin Paulson. Architecture design by Peter Schulte to resemble one the famous traditional estates of the past including a beautifully done covered Porte Cochere with barrel-vaulted wood ceiling. True elegance, with 13,000 sq. ft. of custom living space, every amenity, plus salt water pool, pool house, staff apartment, gym, custom wine cellar with vaulted plaster ceiling, and tennis court with herringbone paneled brick walls and Rebound Ace surface.

4. Modern Contemporary, Southampton, $30,000,000

Listed with William Wolff from Prudential Douglas Elliman. This one-of-a-kind property is situated on over 5 acres of unobstructed 360-degree views of both Shinnecock Bay and the ocean. It includes 200 feet of ocean frontage, a north/south tennis court, specimen trees, slate outdoor barbeque area, and extensive decking. The interior of the house includes a spacious master suite with separate baths and closets, private walk-out decks, fireplace, and office/sitting area. There are four additional bedrooms, 4 1/2 baths, a 40 x 20′ indoor heated pool with connecting pool house with sauna, and entertaining area complete with its own kitchen. The combination sunken living room with fireplace and dining area with second floor decking offers spectacular views of ocean and bay. An updated kitchen offers state-of-the-art equipment, dumb waiter and its own second-floor deck overlooking Shinnecock Bay.

5. Waterfront, Southampton Village, $29,000,000

Listed with John P. Vitello of Brown Harris Stevens. Natural tranquility graces this expansive and secluded waterfront property. Located in the very heart of Southampton Village’s estate section on Shinnecock Bay’s Heady Creek, this nearly 8 acre property encompasses broad, sweeping lawns, mature trees, over 1000′ of pristine waterfront and an original six-bedroom residence. Unsurpassed in the area, the vistas are truly breathtaking, extending over the bay to the ocean beyond. One of the largest waterfront parcels available, the property provides a host of possibilities, including the creation of a new major estate with a manor house, pool, tennis and potential guest house. Ideally located at the end of a quiet cul-de-sac, yet only moments from the finest ocean beaches, world-class shops and restaurants.

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