This Shelter Island estate may be one of the last of its kind. Cherry Tree Farm is a vintage lover’s dream, set on 3.1 acres in the estate area known as Greenlawns.
The area faces west toward Southold and south toward Southampton, sub-divided in the late 1800s to be an exclusive enclave, according to listing agent Penelope Moore of Saunders & Associates.
“The properties here all have the benefit of elevation, panoramic water views, generous acreage, excellent boating and prevailing breezes during the summertime,” she said.
Built in 1890, Cherry Tree Farm is sequestered from the road by a long driveway hugged by established trees. Driving up to the entrance, you’ll pass the home’s tennis court.
The colonial-style home remains as authentic as ever.
“The home has many original details intact,” Moore said, “including beadboard, iron fireplace fenders, original mouldings and woodwork.”
Upon entering the 5,431 square foot estate’s foyer, windows and double doors in the living room provide a view out to the green lawn and blue water.
“The proportion of the rooms throughout the house speaks to the fact that in 1890, this was a special property,” she said. “There are two sections of the home: the main area which was built for the owners and guests, and separate living quarters, which were built for staff after the turn of the last century.”
On the first floor, the traditional home’s living room opens up to a spacious porch with picture perfect lawn views. There’s also a dining room with a gorgeous fireplace, and a butler pantry with original cabinetry, kitchen and a two-story staff wing.
Upstairs is six impressive bedrooms — three have immaculate water views. The master suite has a luxurious vintage tub and pedestal sink also topped off with its own dramatic water view.
The interior of this estate is just the beginning of an experience that feels like the clock has turned back. On the grounds, you’ll find a three-bay garage, barn with high rafters and a rarely-found dog-leg deep water dock. An original beach cabana with old-fashioned dressing areas is another classic edition.
The hard to find L-shaped dock with deep water and a built-in seawall will appeal to those who are avid sailors, Moore mentioned.
“So many vintage homes have already been renovated and, in the process, the configuration of the rooms has changed and details have been stripped or augmented with newer details,” Moore said. “Cherry Tree Farm has been in one family since 1903, and the feeling on the green lawns, under the grand old trees, standing on the beach and just being inside the home is almost like being transported to another era.”
A dream for those who value the traditional feel of a turn-of-the-century home, Moore said, this estate tells tales of the olden days.
is such amazing history in this area,” she said. “Steamboats back in the day
would drop off passengers around the corner on Bootleggers’ Alley, where
stewards would come in horse and buggy to pick up steamer trunks to deliver to
summer homes and hotels.”
The estate is listed at $9,250,000.