The West End Road Compound

Among the native foliage and professionally landscaped grounds, you’ll discover 500 feet of ocean frontage, unobstructed sunrise to sunset views, the last working boathouse on the pond, a clay tennis court, a nearly 14,000-square-foot main residence, and room for thoughtful guest house additions with architectural plans already in place.

With award-winning design, bespoke craftsmanship, and a provenance that reads like a chapter of American cultural history, 69 & 75 West End Road is a peerless residence ready to greet its next generation of proud stewards.

History

Completed in 1894 by Laura Brevoort Sedgwick James, the residence known as Sedgwick Cottage is thought to be one of the oldest homes on the Georgica Dunes. At the time of its construction, East Hampton was already a coveted summer escape for affluent New Yorkers, where vacation retreats were tucked alongside small dairies, potato farms and pristine beaches. The Long Island Railroad reached East Hampton in 1895, cementing the community’s popularity.

Unlike the unbridled opulence of the North Shore’s Gold Coast, the architecture of East Hampton estates at the time was informed by the village’s colonial roots and agricultural heritage. Sedgwick Cottage’s original architect, the prolific J. Greenleaf Thorp, popularized the unassuming style, building a number of Shingle Style cottages throughout the area. The most well-known among them is the famous Grey Gardens, also designed by Thorp and situated just a half-mile from Sedgwick.

Provenance

The history of the West End Road compound reads like a Who’s Who of New York Society: Gilded Age socialites, an aviation titan and an undisputed fashion icon.

Laura Brevoort Sedgwick — granddaughter of Henry Brevoort Jr., a pioneer of Manhattan's Fifth Avenue Gold Coast — commissioned the original home just months before her marriage to Henry Ammon James, a key figure in the East Hampton summer colony. Together, the couple cemented their position in East Hampton society as founding members of the Maidstone Club, the exclusive golf and beach club founded the same year Sedgwick Cottage broke ground. The estate was later used by their son William and his wife Louise Russell Hoadley — known as “Mrs. East Hampton” — who continued the family's deep civic roots through the Ladies Village Improvement Society and beyond.

In 1935, Sedgwick Cottage was sold to Juan Trippe, founder of Pan American World Airways and a pioneer of luxury international air travel. Trippe expanded the compound by acquiring surrounding property from a descendant of one of East Hampton's original Puritan founding families. He also made lasting infrastructure improvements to Georgica Beach and, controversially, excavated a deep hole in the pond as a landing spot for his seaplane. Juan served as president of the Maidstone Club from 1940 to 1944, while his wife, Betty, also served as president of the Ladies Village Improvement Society.

Following Juan Trippe's death in 1981, the property was acquired by fashion designer Calvin Klein and his wife, Kelly Rector Klein, who launched a meticulous transformation of the home under renowned French architect Thierry Despont — known for his restoration of the Statue of Liberty, the Woolworth Building and the Ritz Paris. The living room was reimagined to its current double-height form, the historic boathouse was restored, and the compound was thoughtfully expanded. Throughout their separation and subsequent divorce, the Kleins remained devoted stewards of the property, committed to its care and preservation.

Residence Overview

Completed in 1894 with an iconic tower added in 1899, the primary residence is a classic Shingle Style abode featuring charming gambrel roofs and over 5,000 square feet of decks, patios, and gardens for seamless indoor-outdoor living. Meticulously maintained and updated over the years — including a thorough 2024 renovation spearheaded by a team of leading architects and designers — the showplace expertly pairs glamorous contemporary design with original elements for a timeless aesthetic spanning more than a century of elegant living.

Luxurious interiors span three levels laid with original wide-plank pine, new oak flooring and imported French stone. Soaring beamed and coffered ceilings rise above custom millwork and eight warm fireplaces. A gracious foyer with two-story stone fireplace surround makes a dramatic first impression, while the adjacent formal dining room sets the stage for lavish gatherings. Linger each morning in the charming tearoom, or gather with guests in the sun-drenched double-height living room topped by a glass catwalk. Boasting a fireplace and floor-to-ceiling French doors, the attached screened-in porch delivers all-season enjoyment of the extraordinary landscape thanks to its wraparound floor-to-ceiling glass. Entertaining is effortless with three kitchens — a main kitchen, prep kitchen and staff kitchen — equipped with high-end appliances by La Cornue, Viking and Sub-Zero. The chic bar/lounge keeps refreshments within easy reach.

Across the deck, the home’s iconic tower beckons as a retreat within a retreat, featuring a gracefully curved staircase and handsome paneling that extend to the rounded dome. Here, a spacious family room includes its own wet bar with a private bedroom suite above. The home’s serene upper-level accommodations include a palatial owner’s suite featuring a fireplace, two separate bathrooms with walk-in closets, and access to a large deck. Three secondary suites on this level enjoy sweeping water vistas, while a large study and wraparound viewing decks complete the top floor. The thoughtfully appointed lower level — complete with a fifth bedroom suite, staff quarters, mudroom, laundry and sauna — ensures the estate runs as effortlessly as it lives.

Upgrades/Features

Extensively updated for modern living, the residence features new hurricane-rated Reilly Architectural windows and doors, geothermal systems, a whole-house generator, and fully integrated security — ensuring comfort, safety and resilience in every season. Smart home automation places intuitive control of environment, lighting and entertainment throughout the entire residence.

Property

Thanks to its unrivaled location flanked by Georgica Beach and Georgica Pond, this 8.22-acre sanctuary commands virtually unimpeded, 360-degree views from dawn to dusk. Start your day with a sunrise stroll along the beach or head to the boathouse and dock for a sunset paddle on the pond. Perfect your backhand on the European red clay tennis court while your fans cheer from the 280-square-foot viewing terrace.

Throughout the compound, garden paths amble past irrigated professional landscaping, native plantings and imported fountains, while the outdoor shower rinses sandy toes and paws. An automated entry, locked garden gates, a four-car garage, and ample parking complete a property that is as private and secure as it is breathtaking.

Expansion

Alongside the tennis court, the recreational corridor offers an ideal setting for a two-bedroom, two-and-a-half-bathroom guest cottage and pool/spa addition. On the adjacent 1.63-acre parcel at 69 West End Road, architectural plans envision a new three-story, 3,000-square-foot residence with a two-car garage.

Designs for both additions have been developed and will be permitted as part of the sale — a rare opportunity to thoughtfully continue the growth and improvement of one of the Hamptons' most storied compounds.

Location

Positioned on a bluff near the end of West End Road, this singular property offers unrivaled peace, privacy and direct access to both Georgica Beach and Georgica Pond — all within minutes of the celebrated restaurants, boutiques and storied Maidstone Club that define East Hampton village.

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