The Priciest Pads in the Hamptons

  • What Wall Street Bonuses Can Buy in the Hamptons

    The East Coast may currently be covered in snow, but summer's coming and Wall Street bonuses are bigger than ever. Just as water runs down hill, Wall Street money often flows out to the Hamptons where an army of real estate agents eagerly await all the fat cat financiers, big business barons and hedge fund honchos to swoop in with their newly bulging bank accounts and trophy house dreams. While the average asking price for the 10 most expensive houses in the Hamptons tops $50 million, there’s a wide variety of properties that should please just about any demanding buyer with several tens of millions of dollars to dump on a weekend house that will likely be used less than 6 months out of the year. Photo Credit: jenschapter3
    For the Club Swingers
  • For the Club Swingers

    Three Ponds Farm, currently the second most expensive private home for sale in the Hamptons, has been languishing on the market for a staggering 10 years. The asking price, available only on request, was reported to be a mind-numbing $68 million in late 2009. The sprawling estate, located on the less desirable north side of the Montauk Highway and named after the three fish-stocked ponds on the property, encompasses 60 manicured acres in Bridgehampton, one of the hoitiest of the uber-toity Hamptons neighborhoods. Photo Credit: HREO / Sotheby’s International Realty
    Got Golf?
  • Got Golf?

    As lovely as the three ponds at Three Ponds Farm may be, they are not the posh property’s most distinguishing or desirable characteristic. It’s the private, PGA-rated 18-hole Rees Jones-designed golf course and wood paneled pro shop that features a second floor bar and bathroom that will attract deep-pocketed club swingers tired of fighting for a good tee time at one of the many private clubs in the Hamptons. The clubhouse also includes a separate one bedroom and one bathroom apartment that will house a resident golf pro. Photo Credit: HREO / Sotheby’s International Realty
    The Main House
  • The Main House

    The main house at Three Ponds Farm — a monolithic, two-story Mediterranean affair surrounded by terraces, loggias and pergolas that drip with fragrant flowers — measures in at a monstrous 20,000+ sq. ft. and includes eight bedrooms and 12 bathrooms. Photo Credit: HREO / Sotheby’s International Realty
    A French Influence
  • A French Influence

    The lavishly appointed interior spaces include a double-height living room with a barrel-vaulted ceiling, hardwood floors, an antique fireplace surround shipped from a castle in France, and several sets of French doors that allow the ocean breeze to float through the humongous house. Photo Credit: HREO / Sotheby’s International Realty
    Swimming Pool Complex
  • Swimming Pool Complex

    A long, wisteria-strewn pergola leads from the main house to the swimming pool complex that includes a pool house with double changing rooms, a bathroom and facilities for storing the multitude of sun loungers and pool toys in the off-season. For sporty types, there is a perfectly clipped grass tennis court on the other side of the property. Photo Credit: HREO / Sotheby’s International Realty
    A Gardener's Dream
  • A Gardener's Dream

    The main house is ringed by a dozen or more meticulously maintained gardens. At one end of the walled and perfectly symmetrical rose garden, a glass-wrapped garden house has a great room, kitchenette, full bathroom and heat and air conditioning systems that ensure year-round comfort. Other structures that dot the estate are, according to listing information, a “fish house,” an antique barn and another cottage equipped with the same amenities as the garden house. Photo Credit: HREO / Sotheby’s International Realty
    Have Some Friends Stay Over
  • Have Some Friends Stay Over

    At the front of the property, near the main entrance gates, a vintage farmhouse with three bedrooms and 3.5 bathrooms provides perfect guest accommodations or caretaker quarters. Three Ponds Farm can also be accessed by another long, gated driveway that runs along the pastures of the 30-acre horse farm Madonna recently bought from Kelly Klein. Want more info? Click here. Photo Credit: HREO / Sotheby’s International Realty
    For High Fallutin' Horsey Types
  • For High Fallutin' Horsey Types

    The most expensive property currently available in the Hamptons is not the $68 million Three Ponds Farm, but a Bridgehampton horse farm called Two Trees, listed at a spine-tingling $75 million. Like Three Ponds, Two Trees sits far from the ocean on the less desirable north side of Montauk Highway. The horsey spread sprawls across 115 acres of farm and pasturelands and is equipped with full equestrian facilities that include 100 stalls, eight grooms’ apartments, three barns with kitchens, two indoor arenas, a number of paddocks and two competition-sized polo fields. Photo Credit: HREO / Sotheby’s International Realty
    A Farmhouse Feel
  • A Farmhouse Feel

    The main house at Two Trees is a historic and classic Hamptons-style cedar-shingled farmhouse. The approximately 2,500 square-foot, fully renovated and restored residence has four bedrooms, 3.5 bathrooms, four fireplaces, a gunite swimming pool and all-weather tennis court. A second residence, for guests or staff, contains four bedrooms and two bathrooms. Want more info? Click here. Photo Credit: HREO / Sotheby’s International Realty
    For Montauk Multi-Millionaires
  • For Montauk Multi-Millionaires

    Next up, a $50 million modern mansion in Montauk sits high on a bluff overlooking the Atlantic Ocean. The half-mile-long private drive winds through the secluded, 35.5-acre estate and leads to an approximately 7,000 square-foot house with five bedrooms, four bathrooms, radiant heat marble floors and massive walls of glass. The house is built to withstand winds of up to 150 miles per hour. The property’s nearest neighbor is the legendary estate Eothen, formerly owned by Andy Warhol and now owned by J. Crew CEO Mickey Drexler, who paid $27 million for the quirky, 40-acre property in 2007. Want more info? Click here. Photo Credit: HREO / Corcoran Group
    For Boat People
  • For Boat People

    The south side of the Hamptons fronts the Atlantic Ocean while the north side faces the Great Peconic Bay where Tyndal Point, a 55-acre parcel in the North Haven area is listed at $49.9 million. The heavily wooded and largely unspoiled property stretches 3,000 feet on the water and offers three primary residences and two carriage houses. Perhaps the most notable features on the property are the two deep-water docks for parking yachts and the protected lagoon with additional docks for providing boats safe harbor during storms. Want more info? Click here. Photo Credit: HREO / Corcoran Group
    For Thrill Seekers and Entertainment Junkies
  • For Thrill Seekers and Entertainment Junkies

    The newly built Bridgehampton estate known as Sand Castle comes in at $49 million. The shingled beast, desirably situated on 11.5 acres south of the Montauk Highway, weighs in at a hotel-sized 31,000 square feet and contains 14 bedrooms and 19 bathrooms, a count that includes commodious staff quarters and a gigantic, 2,800 square-foot master suite. Photo Credit: HREO / Prudential Douglas Elliman Bridgehampton
    You Will Never Be Bored
  • You Will Never Be Bored

    Besides its hulking size, Sand Castle’s calling cards are the many entertainment amenities (in addition to the expected swimming pool and tennis court), including a children’s lounge, a virtual golf room, media room with five plasma TVs, a squash and racquetball court, a two-lane bowling alley, a full-on disco, rock climbing wall, complete spa facilities and an indoor half pipe for skateboarding. Want more info? Click here. Photo Credit: HREO / Prudential Douglas Elliman Bridgehampton
    For Swimming Pool Lovers
  • For Swimming Pool Lovers

    Also priced at $49.5 million is Linden, a 9.1-acre property in the historic and super swank Southampton estate section. The freshly renovated, multi-winged mansion was built in 1915, measures 18,000+ square feet and includes 12 bedrooms, 12 full and three half baths plus separate staff quarters. The grand estate, ringed by mature trees and numerous gardens, has a gigantic and dramatic water feature that shoots a stream of water high into the air. Photo Credit: HREO / Sotheby’s International Realty
    Water Features
  • Water Features

    In addition to a carriage house and four-car garage, the estate’s resort-like amenities include an in-home fitness center, tennis and paddleball courts, and an outdoor swimming pool with adjacent pavilion as well as an indoor swimming pool for winter-time water babies. Want more info? Click here. Photo Credit: HREO / Sotheby’s International Realty
    For Investors and Developers
  • For Investors and Developers

    For a still insanely expensive $49 million, there are 40 acres of farmland in sleepy Sagaponack. The pond-front property currently has three houses on busy Montauk Highway, but it’s an investor’s delight since there is plenty of potential for further subdividing the property or developing a working vineyard. Want more info? Click here. Photo Credit: HREO / Engel & Voelkers
    For Architecture Buffs
  • For Architecture Buffs

    The most expensive property on the market in the historic and quaint village of East Hampton is a recently renovated mansion more than a century old facing uber-exclusive Georgica Pond. Listed at $39.5 million, the residence was originally designed by noted architect Stanford White. The current owner carefully had the 12,000+ square-foot house lifted and turned 90 degrees so that the 30-foot high living room would have direct views of the pond. The house sits on 1.9 manicured acres and includes six bedrooms, seven bathrooms, a water-side swimming pool and a detached guest cottage. Want more info? Click here. Photo Credit: HREO / Corcoran Group
    For Francophiles
  • For Francophiles

    Sitting on 42 perfectly-located acres in itty-bitty Water Mill is Beechnut Hill Farm. The mansion stretches a stunning 225 feet, measures 16,800 square feet and contains seven bedrooms and 7.5 bathrooms. Listed at $39.5 million, the traditional, gambrel-roofed “cottage” is filled with French chalked oak paneling, antique French fireplace surrounds and wide-plank black walnut floors along with all the modern luxuries such as a gourmet kitchen, an elevator serving all three floors and a detached pool house adjacent to a 50-foot long pool surrounded by a Turkish limestone terrace. Want more info? Click here. Photo Credit: HREO / Prudential Douglas Elliman Bridgehampton
    For Old-School Hamptonites
  • For Old-School Hamptonites

    The 10th most expensive house listed in the Hamptons has an asking price that is only available on request. A little research indicates the asking price is most likely more than $35 million but less than $40 million. The pristine 10.2-acre property in the swish, old-school Southampton estate section includes a three-story, 12,000+ square-foot shingled Dutch Colonial with nine bedrooms, nine full and three half bathrooms and nine fireplaces. Photo Credit: HREO / Sotheby’s International Realty
    Landscaping to Die For
  • Landscaping to Die For

    The tirelessly maintained grounds have a reflecting pond, brick-terraced pool with a new pool house, a newly built two-story guest cottage with two bedrooms and 2.5 bathrooms, a Har-Tru tennis court, basketball court, wide stretches of well-watered lawns and a working greenhouse and vegetable garden. Want more info? Click here. Photo Credit: HREO / Sotheby’s International Realty
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