Tudor estate built on grounds of a historic NY orchard is asking for $25M

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...