Luxury Real Estate Property Market Insights

American Royalty: The Timeless Allure of Legacy Properties

From Connecticut to California, take a tour of five homes with rich history and celebrated provenance—and discover the investment opportunities they offer

The world of trophy real estate represents the best on offer in the marketplace—properties that are one-of-a-kind assets, with a prime location, expansive square footage, and attributes that amplify a luxury lifestyle. Perhaps the most exclusive category, however, are homes with a storied history: legacy properties, the extraordinary estates of American “royalty.”

Although the term trophy might be applied to ultra-prime real estate, legacy seems more fitting for many of these one-of-a-kind, historical residences. This unique asset class combines a long-term investment strategy and the satisfaction of acquiring something no one else can possess—like a classic car or fine artwork, a legacy real estate asset’s value stems from its uniqueness.

One-of-a-Kind Historical Residences

Throughout American history, the number of properties that meet the definition of “legacy property” is extremely limited. Still more limited is the number that are available for purchase, as they often remain in the family. “This is certainly the case in Newport, Rhode Island,” says Kendra Toppa, sales manager at Lila Delman Real Estate. “Here, this category of property has been in some, often socially prominent, families for generations—and the buyers of these estate homes envision their own family occupying them for generations to come.”

In owning a legacy property you become part of the history of that unique real estate asset. You are writing your own story—Sonja Cullaro

Newport’s history stretches back to the 1800s, when wealthy families looked to greener, more tranquil areas outside increasingly crowded cities to establish new homes. By the turn of the 20th century, wealthy East Coast American families—many of whom had earned their fortune building railroad or oil empires—had built expansive homes on the coastline.

Lands's End in Newport Rhode Island
Land’s End was built in 1864 for Boston banker Samuel Gray Ward and was home to Robert Livingston Beeckman, a US Open Tennis finalist who later became governor of Rhode Island, before being purchased by novelist Edith Wharton.

These homes, such as Edith Wharton’s Land’s End, the Vanderbilts’ The Breakers, and the Wideners’ Miramar continue to be occupied. In fact, Land’s End—situated on 5.6 oceanfront acres (2.3 ha)—recently sold for $8.6 million. “Its buyers appreciated the property’s unique history and architectural importance,” says Toppa, who represented the seller. “But it’s a residence that also strikes the perfect balance of elegance and comfort.”

Glittering Pasts

“Legacy properties have maintained their cultural significance over multiple generations,” adds Sonja Cullaro, Executive Vice President for Christie’s International Real Estate, Northern New Jersey. “They are set apart from other exclusive real estate in the market because their distinct provenance cannot be replicated.”

“I remind potential buyers that by owning such a legacy property, they become part of the history of that unique real estate asset—they are writing their own story,” she says. One such property, which would allow a buyer to combine a glittering past with the present, is Darlington, on the market with Christie’s International Real Estate, Northern New Jersey.

Darlington mansion in New Jersey
Built of Harvard brick and Indiana limestone, Darlington's palatial architecture and beautiful grounds have earned it the nickname "the American Versailles."

Today, the 58-room, three-story mansion is listed on the National Register of Historic Places, but it was originally the dream of George Crocker, son of railroad magnate Charles Crocker. Constructed in 1907, the majestic dwelling was modeled after an English castle by architect James Brite, who along with his partner, Henry Bacon, also created the original Madison Square Garden in New York City. It has undergone a complete renovation over the last seven years and is now equipped with state-of-the-art amenities—while retaining its original architecture. “The perfect fusion of the past, present, and future,” says Cullaro.

Knowing that a property has history, was loved, and impeccably cared for by someone of notable importance adds to its allure—Shaylene Neumann

Architectural Heritage

Another property which seamlessly fuses past and present is High Point Estate in Middletown, New Jersey, thanks to its combination of architecture by an American icon with exquisite European style. The estate’s majestic 18,000-square-foot (1,672 sq m) main house, inspired by grand French chateaux, was designed in 1999 by architect Robert A.M. Stern, whose other celebrated works include 15 Central Park West.

“It’s highly unusual for A.M. Stern to design a single-family home and at High Point Estate he created a rare and special property, comparable to owning an exquisite work of art,” says Gloria Nilson.

A view of High Point across its lawns
Spaciousness combines with architectural splendor at High Point, which offers six bedroom suites, a three-bedroom guest house, and a loft-style recording studio in its former stables.

Situated just an hour from New York City, High Point nonetheless offers its residents a privileged outdoor lifestyle thanks to its 37 acres (15 ha) of landscaped grounds and a private dock on 700 feet (213 m) of frontage on the Navesink River. “The house has been positioned on its grounds with the utmost care to ensure exceptional views, from watching the sun rise over the Atlantic to seeing it set over the Navesink River,” Nilson adds.

Legacy properties are set apart from other exclusive real estate because their distinct provenance cannot be replicated—Sonja Cullaro

Everlasting Art

While also on the East Coast, the one-of-a-kind appeal of Herrick House in Connecticut is thanks to both its architecture and legacy of art. The late Melva Bucksbaum, a trustee of the Whitney Museum of American Art, modernized the 19th-century home in 2005, adapting the 9,000-square-foot (836 sq m) main house to complement her contemporary collection. Today, it’s a space dedicated to displaying, and living with, art.

Herrick House, the estate owned by art patron Melva Bucksbaum
Set on 52 acres (21 ha) in Connecticut’s serene Litchfield Hills, Herrick House comprises the original 1920s farmhouse, a barn, and several outbuildings—as well as a custom-built private art gallery, the Granary.

“The Herrick House estate was previously owned by Frank Oz, the creator and writer of The Muppets, who would do his writing there. It’s easy to see why it still remains an inspiring and creative place today,” adds Shaylene Neumann, a partner at Neumann Real Estate, which is representing the sale of the estate. “But to me the property’s most striking feature is the Granary—a modern 14,000-square-foot (1,300 sq m) private art gallery that was designed by renowned architect Steven Learner, and which has hosted many artists in residence.”

Glorious Grounds

In legacy properties, the unrivaled amenities you’d expect of trophy homes have been given the time and care they need to develop into something truly special. This is especially evident in the expansive grounds of Green Gables, the Woodside, California, estate built by banker and philanthropist Mortimer Fleishhacker in 1911, which is currently on the market through Christie’s International Real Estate.

Green Gable's vast grounds include gardens and natural woodlands. "Not only is it a legacy property, it's also situated on ultra-prime real estate," says Wright. "No one could possibly deny it the title of 'trophy property.'"

Spread over 74 acres (30 ha)—a rare size in the Silicon Valley area—the estate houses orchards and large vegetable and flower gardens alongside natural woodlands filled with majestic old-growth trees, such as giant redwoods. “The main house, designed by renowned craftsman-era architects Henry and Charles Green, is one of the most outstanding examples of the American Arts and Crafts movement,” adds Zackary Wright, Executive Director, Western Regional Manager at Christie’s International Real Estate. “And the gardens are complemented by a football-field-length Roman reflecting pool and scenic lily pond—it’s a masterpiece of refined, elegant country living.”

The buyers of these iconic homes respond to the story behind the legacy, and hold onto it when the property is in their possession—Shaylene Neumann

Legacy Investments

Who, then, are the potential buyers for these iconic homes? “Those who respond to the story behind the legacy, and hold onto it when the property is in their possession,” says Neumann. “Knowing that a property has history, was loved, respected, and impeccably cared for by someone of notable importance adds to its allure.”

She also points out that the pool of potential buyers may have increased due to the current global health crisis. “High-net-worth buyers are seeking space and privacy, along with amenities that they and their families can enjoy in safety. With that in mind, and possible work and lifestyle changes ahead, a legacy property can be an excellent investment.”

Banner image: High Point Estate, Middletown, New Jersey