Epic $25 Million Tudor Estate Built on the Grounds of a Historic Orchard Is Listed for First Time

An extraordinary generational compound on Long Island’s North Shore has made a dramatic debut on the market, listing for the first time in its decades-long history with an equally impressive asking price of $24.98 million.

Set across 35 picturesque acres—which include land that was once used as a thriving orchard—the compound at 1 Applewood Estate centers around an enormous 19,000-square-foot Tudor-inspired manse that combines old-world craftsmanship with modern luxury. 

Beyond the gated entry, a long tree-lined drive, and its many formal gardens, the stone and brick manor looks like the kind of place you’d happen upon while wandering the English countryside.

Located in an area renowned for its Gilded Age mansions, you could be forgiven for thinking that Applewood dates back to that same era; certainly, it was built to appear that way. Yet the manse was actually constructed in 2005, albeit with careful care and attention paid to its historical inspirations.

"The primary manor itself is already relatively modern by Gold Coast standards," says listing agent Jacob Simon of Serhant East End LLC. "Buyers get the emotional feel of a classic Gold Coast estate, but with a much newer core structure."

However, the property's roots stretch back much further than the house itself.

Initially, the land was used as an apple orchard in the early 1900s, before the estate passed to renowned American portrait artist Montague Flagg.

Though it has been decades since the grounds served as a functioning orchard, that legacy lives on through meticulously maintained grounds and a carefully curated collection of structures, including an attached two-bedroom cottage, a standalone two-bedroom cottage, and a pool house with two bedrooms.

A small piece of the property's legacy also remains intact on the land: a reconstructed circa-1914 stone barn that now serves as a luxury retreat.

The manor's architecture embraces the grandeur traditionally associated with Long Island's Gold Coast. A slate roof sits atop the brick-and-stone exterior, while oversized parquet floors, handcrafted iron fireplaces, extensive millwork, coffered ceilings, and onyx marble detailing create a regal old-world atmosphere.

"Inspired by Tudor Cotswold architecture, the compound is a masterclass in cohesive design, blending old-world craftsmanship with modern luxury across multiple residences and lifestyle amenities," the listing states.

"Constructed with slate, brick, and stone, the home showcases extraordinary craftsmanship through onyx marble accents, oversized parquet flooring, handcrafted iron fireplaces, detailed millwork, and dramatic entertaining spaces throughout."

A dramatic staircase anchors the foyer and leads into multiple formal entertaining rooms and a library loft. But one of the home’s most impressive features is the ballroom. 

"The ability to entertain with spaces such as the ballroom, which is huge with soaring 23-foot ceilings, is incredibly attractive," Simon says. "The layout is also surprisingly modern, something most of Upper Brookville's true estates do not have."

The estate functions more like a private compound than a single-family residence. With 13 bedrooms and 11.5 bathrooms, there’s ample room for extended hosting or large-scale entertaining. 

The sheer scale of the property is even more remarkable on the outside. 

"There are almost no estates with this amount of land on the Gold Coast," says Simon. "The privacy is unmatched, and the level of landscaping throughout the property is not something that can be found anywhere else on the Gold Coast."

Situated in Upper Brookville, one of the most coveted villages along Long Island's North Shore, Applewood Estate also offers convenient access to Manhattan and nearby attractions like Planting Fields Arboretum State Historic Park, Old Westbury Gardens, and the Theodore Roosevelt home at Sagamore Hill. Elite country clubs, equestrian facilities, yacht clubs, and Long Island Sound beaches are also all within a short drive. 

"Rarely does a property offer this level of acreage, architectural integrity, historical significance, and lifestyle versatility within one of the North Shore's most coveted enclaves," the listing concludes. "Applewood Estate is not simply a home—it is a private world crafted for legacy living, grand entertaining, and timeless retreat."