Holiday House Tours: Opulent, Historical Homes and Where to Find Them

The Hamptons and North Fork comprise a rare mix of luxurious estates and historical homesteads, often hidden from the public eye. This holiday season, the East End community is invited to peek inside lavish, unique and vintage homes, marvel at the eccentric amenities and take note of the posh interior design and holiday decorations. It’s almost time to embark on the East Hampton House & Garden Tour and the Cutchogue Holiday House Tour.

The East Hampton Historical Society has selected five houses that encapsulate the spirit of Hamptons living, showcasing contemporary architecture, classic shingle cottages and coveted south-of-the-highway real estate. “The East Hampton House Tour is a must-see event for people out here who enjoy design, are historical enthusiasts or are renovating a house,” event chairman Joseph Aversano says. “We’ve put together a wonderful collection of houses highlighting the different architectural trends that are happening, and this year we really made an effort to go beyond East Hampton Village.” The tour is scheduled for Saturday, November 30 from 1–4:30 p.m. with a holiday cocktail party at the Maidstone Club on Friday from 6–8 p.m. Tickets raise much-needed funds for the historical society’s children’s programs and the maintenance of their historic structures.

The first stop on the East Hampton House & Garden Tour offers stunning views across Hook Pond to the ocean, the bay and beyond. The Hamptons beach house was designed by famed architect Robert A.M. Stern who helped revive and bolster shingle-style architecture to the lofty status it holds on the East End today. The open, modern design exudes seaside elegance, blowing salty sea air throughout each expansive room.

Located on Davids Lane in East Hampton, the second home, Dowager Inn, pays homage to the local, historical inns that line the village’s Main Street. The homeowners have created a warm, inviting haven with intimate rooms, outdoor spaces and all the elements required for spirited entertaining.

Amagansett’s Promise Land comprises a collection of all-natural barns connected by glass hallways on a property boasting dramatic sculptures and stunning views of Napeague Bay. The original section of the house is modeled after the De Menil Barn that became the East Hampton Clerk’s Office.

Marshall Watson, known for his European-inspired style, creates textured, detailed, simple interiors, which can be found in abundance at his Federal-style house by the bay. The tour offers a rare chance to see how the nationally acclaimed designer stages his own home, right here in East Hampton.

With a nod to the East End’s agrarian roots, the final stop on the tour puts a modern spin on the minimalist, shingled potato barn. Millhouse, originally shipped from Montauk for use as an army barracks, is now a homogeneous, light-filled space that stands apart from other potato barns found in the Hamptons.

North Fork architecture and interior design lovers needn’t feel left out, as Sannino Vineyard’s seventh annual Cutchogue Holiday House Tour takes place on Saturday, December 7. Tourgoers will wine and dine their way through four breathtaking homes and The Old House, built in 1649, making it the longest-standing, English-style medieval home in New York. The self-guided tour begins at 11 a.m., with the last entry time at 3:30 p.m. Each stop offers a full sensory experience with the scents of paired drinks, hors d’oeuvres and desserts by local eateries and wineries—including Michelangelo’s, Touch of Venice, Sparkling Pointe, Suhru Wines, NoFoDoCo, Backyard Brine and Woodside Cidery—wafting through each room. A portion of ticket proceeds helps stock the shelves of Community Action Southold Town, Inc. (CAST) and supports the Cutchogue-New Suffolk Historical Council. A Toys for Tots collection box will also be available.

“There is a combination of historic and newer homes on the tour, each with their own unique style of holiday décor,” Sannino Vineyard B&B innkeeper and founder Lisa Sannino says. “I paired local businesses together carefully to complement each other, and all of the businesses involved are happy to give back to the community that we live in.”

The first stop on the North Fork tour is Bay Breeze Inn, which features a newly renovated 1860 house and cottage with all the latest amenities and chic, country-coastal décor. The restaurant on premises, Sea & Salt Bistro, will provide delectable bites as guests explore the historic inn.

Blue Iris Bed & Breakfast has spacious rooms, manicured two-acre grounds and modern amenities, while maintaining the image of a classic farmhouse. A popular spot for photos and special occasions, the unmatched charm of the B&B has attracted guests for nearly two decades.

Constructed in the 1850s, the Milford T. Benjamin House was purchased and restored by the Goerler family in 1985 and now houses the family’s winery and tasting room, Jamesport Vineyards. Sip this season’s top wines as you explore the property’s patio, wine bar and beautifully decorated rooms.

The Tuscan-style suite and villa at Sannino Vineyard Bed & Breakfast offer gorgeous views of the main estate, with the balcony patio overlooking the vines. The B&B isn’t normally open to tours, so guests should take full advantage of this exclusive look at a truly marvelous property.

The tour ends with a lively after party at Sannino Vineyard’s new Cutchogue tasting house at 5 p.m. Feast on a full buffet dinner prepared by Ammirati’s Catering from Mattituck’s Love Lane as you discuss the immaculate homes enjoyed throughout the day.

For tickets to the Cutchogue Holiday House Tour, visit cutchogueholidayhousetour.com.

And for tickets to the East Hampton House & Garden Tour, visit easthamptonhistory.org.