Top 5 Hamptons Estates for Sale with Old-World Flair

The Hamptons has long been home to some of the grandest estates imaginable. Here, we present five homes for sale that still carry that special old-world flair and all the trappings of the bygone Summer Colony days of yore.

315 Rose Hill Road, Water Mill
$39,000,000

This stunner was built in 2005, but it was clearly designed to resemble elegant estates of generations past while offering the convenience and ease of modern construction and amenities. Standing on more than 4 acres on Mecox Bay, the 20,000-square-foot home includes 8 bedrooms, 11 baths and 8 fireplaces with early 19th century mantels, coffered ceilings, more than 120 exterior architectural brackets and roomy balconies overlooking the stately grounds. The grand entrance is an old-world vision opening to a cast bronze double staircase and 19th century stained glass skylight. The property also has an infinity-edge pool, Jacuzzi, tennis court, wine cellar, gym, theater, sauna, dock, koi pond, and a spectacular kitchen by world-renowned designer Mark Stech-Novak, with separate prep-kitchen, bakery and main kitchen. In new-world fashion, the estate can be controlled and monitored from anywhere in the world through its Crestron security camera and entertainment system. Douglas Elliman Realty

217 Rose Hill Road, Water Mill

217 Rose Hill Road, Water Mill, Photo: Richard Taverna, Courtesy Sotheby’s International Realty

217 Rose Hill Road, Water Mill
$27,500,000

This circa 1920s elegant Georgian-style red brick country home rests on more than 5 acres with a long, tree-lined driveway, open rolling lawn, Mecox Bay vistas and 330 feet of direct waterfront with dock. Designed by Goodwillie and Moran, the residence is a classic. Whispers of the past come through the carved wood-trimmed front door, the formal dining room with fireplace, walnut-paneled living room with Grinling Gibbons carvings over the fireplace mantel, and the elliptically-shaped outdoor loggia that opens on to an outdoor dining porch and swimming pool. The former billiards room, now a library/den retains its knotty pine wainscoting and kitchenette, while an area once used for outdoor sleeping is now an oversized family room with fireplace and porch. The property and residence exude old-world charm, but they’re outfitted with modern systems and mechanicals for the new-world homeowner. Sotheby’s International Realty

Greek Revival/Italianate, Sag Harbor

Greek Revival/Italianate, Sag Harbor, Photo: Courtesy Brown Harris Stevens

Greek Revival/Italianate in Sag Harbor
$21,000,000

Originally built in 1833, this large Greek Revival style home was enlarged and renovated in 1850 in the Italianate style. Modern amenities balance harmoniously with original details within this 10,000-square-foot, 7-bedroom residence on more than an acre with 4 levels of living space, serviced by both stairs and elevator. Outside, the house has a swimming pool, gardens and specimen trees. Inside features grand parlors, covered porches, high windows and a third-floor loft with bathroom leading up to a widow’s walk with 360-degree views of the historic whaling village. A finished lower level with full bath and 4-bay, climate-controlled garage with art studio, bathroom and shower complete the picture. Brown Harris Stevens

Watchcase Penthouse 400, 15 Church Street

Watchcase Penthouse 400, 15 Church Street, Sag Harbor, Photo: Courtesy Corcoran Group

Watchcase Penthouse: 15 Church Street, Sag Harbor
$7,900,000

Among the crown jewels of Sag Harbor’s Watchcase condominiums, Penthouse 400 is everything this project promised. With 2,848 square feet in an octagonal tower, this harbor-facing 3-bedroom, 3- and 2-half-bath home has fabulous views from every well-appointed room. Built in an existing 1881 brick factory building, the condo calls forth its historic provenance with over 12-foot-high pine-beamed ceilings, oversized windows, and Watchcase’s signature exposed brick. The sprawling layout offers a gracious master bedroom with huge walk-in closet and luxurious 5-fixture bath, and 2 en-suite guest rooms. A grand staircase ascends from the living room to a glamorous, window-encased library with remarkable views from the highest interior elevation of the factory. A double-sided fireplace is open to the library on one side and to the immense, 1,848-square-foot rooftop terrace on the other. Corcoran Group

352 Mitchells Lane, Bridgehampton Sotheby's International Realty

352 Mitchells Lane, Bridgehampton, Photo: Sotheby’s International Realty

352 Mitchells Lane, Bridgehampton
$1,975,000

Adjacent to a horse farm and covered with beautiful creeping ivy, this circa 1900s traditional home is on one manicured acre, accented by mature landscaping, sweeping lawns and pool. It offers 2,800 square feet of living space, 5 bedrooms, including master suite with fireplace, 4.5 baths, living room with fireplace, open living and dining area, country kitchen with breakfast area, media room, staff quarters and screened-in porch. Sotheby’s International Realty

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