Aerial view of the converted barn estate and heated pool at 101 Drake Road
Pleasant Valley · Near Millbrook, NY

A Converted 19th-Century Barn, Reimagined

An artful post-and-beam estate of two restored barns, a heated pool, and eleven private acres of lawns, pastures, and wildflowers — 65 minutes from Manhattan.

$1,195,000
3Bedrooms
2.5Baths
2,820Sq Ft
±11Acres
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The Property

Artsy and beautiful best describe a place the grounds make unforgettable.

A converted 19th-century barn with a complete glass wall overlooks a magical, very private pastoral setting — manicured lawns, horse pastures, wildflowers, and pine trees, with metal sculptures dotting the landscape. A second converted barn, down a long private driveway, serves as a pool and summer guest house. Meticulously restored, it blends contemporary ease with classic post-and-beam character — ideal for families and couples alike.

$1.195MFor Immediate Sale
3 / 2.5Beds / Baths
2,820Square Feet
20×40Heated Pool
65 minTo Manhattan
$22KAnnual Taxes
A Film of the Estate

Walk the property, in motion.

The glass-walled great room with post-and-beam ceilings
The Great Room
Dining area beside the glass wall
The Main Barn

A wall of glass, open to the woods.

The main barn was meticulously restored to mix contemporary comfort with classic post-and-beam craft — soaring vaulted ceilings, original hand-hewn beams, and wide-plank floors. A complete glass wall dissolves the line between the great room and the pastoral landscape beyond.

  • 3 bedrooms + sitting area with double day bed
  • Sleeps 6–8 guests comfortably
  • Commercial kitchen with ample storage
  • 2.5 bathrooms
  • Brand-new HVAC & hot water
  • Music room & art-filled loft
The 20 by 40 foot heated pool surrounded by English garden
Pool & Garden
Pool house interior opening to the grounds
The Second Barn

A pool house, and an English garden.

Down a long private driveway, the second converted barn serves as a pool and summer guest house. The large 20×40-foot heated pool is wrapped in an English garden with total privacy. The grounds here are extraordinary.

  • Own kitchen, bath & bedroom
  • 20 × 40 ft heated pool
  • Private English garden setting
  • Convertible back to a 3-stable barn
  • Strong summer rental history
  • Complete seclusion
Aerial of the estate grounds, lawns and pine trees
Eleven Acres
The restored barn exterior with gardens
The Grounds

Lawns, pastures & metal sculptures.

Manicured lawns give way to horse pastures, wildflowers, and stands of pine. Metal sculptures are scattered across the landscape like an open-air gallery. It is the kind of privacy and beauty that is increasingly rare this close to the city.

  • Manicured lawns & horse pastures
  • Wildflower meadows & pine groves
  • Sculptures across the landscape
  • Total privacy, long private drive
The Location

Three minutes off the Taconic.

101 Drake Road sits in Pleasant Valley, NY — moments from the charming village of Millbrook and the heart of the Hudson Valley, yet an easy run to the city. Wineries, farm stands, and rail are all close at hand.

To the Taconic Parkway3 min
Village of Millbrook5 min
Local wineries10 min
Amtrak & Metro-North15 min
Manhattan by car~70 min
Seller Says Sell Now
$1,195,000
101 Drake Road, Pleasant Valley, NY 12569 · Annual taxes $22,000 · MLS #951502
Owner — Direct

James G.

Speak with the owner directly
EmailJamesg62@gmail.com
Listing Agent

Jake Garay

SERHANT.
Call(914) 772-2603Emailjakegaray@serhant.com
View the full SERHANT. listing →