

In the fall, when the flurry of East End festivities are finito, it’s hard to return to real life — and apartment living.
That’s when our envious eyes wander north, where the leaves are drenched in color and a flush of dramatic estates are now on the market.
Behold, Arrow Hill at 2525 Purchase St. in Westchester County. Built in 1927 on 40-plus green acres, it’s one of the most significant properties to list in the area in years.
“In almost three decades of being in the real estate industry, I have never experienced a more inherently unique and versatile property than Arrow Hill,” says broker Louis Katsoris of Julia B. Fee Sotheby’s International Realty, who has it listed at $28.5 million.
And dig this for grandeur: The recently reno’d neoclassical pile expands over 14,000 square feet in the main house with eight bedrooms and nine full bathrooms.
The grounds have two guest residences, a do-what-thou-wilt “hanger,” a pool house and formal landscape architecture with enough fountains and garden statuary to make a duke feel at ease.
The tennis court, indoor sports court, gym and, yes, “catacombs” offer all the venues needed for your own game of “Traitors.”
Follow your compass about 18 miles northeast to the town of Pound Ridge for a completely different take on a surreal estate.
Here lies 51 Old Stone Hill Road, an award-winning rectangular home built into 19.5 acres of wooded and boulder-strewn landscape by Philly-based designer KieranTimberlake.
Reflect upon its mirror, glass, steel and zinc-coated copper jigsaw facade. Compass broker Brian Milton calls it “a rare, collectible work,” and like a lesser Rothko, has it listed for $15 million. Inside, the four-bed, four-bath, 4,485-square-footer has “gallery-like interiors,” floating staircases and walls of glass blended with natural materials like stone and warm woods.
Of course architecture isn’t enough, so how about a 2,400-bottle wine cellar, an outdoor kitchen and a media room built by audiovisual pros?
Additional autumnal attitude can be attained by driving another two hours north and turning right.
Sneak just five miles over the Massachusetts border to find another estate that’s a once-in-a-generation buy. Designed in 1893 by Peabody & Stearns in the style of a 16th-century Florentine palazzo, with 21-acre grounds by Frederick Law Olmsted, the Wheatleigh at 11 Hawthorne Road in Stockbridge is a rare surviving example of a Gilded Age “Berkshire cottage.”
It hit the market asking $14.5 million in July after five decades operating as a boutique five-star hotel.
It has 19 bedrooms, 25 bathrooms and almost 20,000 square feet of space, plus a cellar ready for 6,500 of your best bottles. Pool, tennis court, gym, it’s got it all.
Does it need a residential redo after years of gallivanting guests? Sure it does. But that’s just turning over a new leaf.
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