101 Drake Road, Pleasant Valley, NY 12569

• 3 beds |
• 3 baths |
• 2,820 sqft

Property Description

Tucked behind a quiet country approach, two meticulously restored 19th-century barns have been reimagined into a refined luxury residence and companion pool house that feel timeless in character and elevated in execution. Inside the main residence, soaring vaulted ceilings, original hand-hewn beams, and wide-plank floors establish a sense of warmth and permanence, while expansive walls of glass invite natural light and create a seamless connection to the surrounding landscape. At the heart of the home, a beautifully appointed country kitchen anchored by a wood-burning fireplace is designed for both slow mornings and elegant entertaining. A dramatic great room and adjoining music room provide generous gathering spaces, while three bedrooms offer private, hotel-level comfort for guests. Outdoors, a heated in-ground pool is set among stone terraces and anchored by a fully outfitted luxury pool house with kitchen, bedroom, and bath, ideal for hosting, unwinding, or extended stays. The setting offers exceptional privacy while remaining effortlessly connected. Located less than 75 miles from New York City and just 10 minutes from the center of Millbrook, the property delivers the best of Hudson Valley living. World-class wineries, scenic hiking trails, equestrian estates, and farm-to-table dining are moments away, creating a lifestyle defined by balance, where weekend escape meets full-time retreat. This is not a conversion. It is a destination. A rare offering where historic architecture, modern luxury, and the rhythms of country life converge, all within easy reach of the city.

Listing Status:

Active

Data Last Updated:

March 26, 2026 at 6:23AM

Listing Office:

Serhant LLC : 646-480-7665

MLS ID:

951502

Interior

• General: Beamed CeilingsBuilt-in FeaturesEat-in KitchenHigh CeilingsHigh Speed InternetOpen FloorplanOpen KitchenOriginal DetailsPrimary BathroomRecessed LightingSmart ThermostatStorageWalk-In Closet(s)Washer/Dryer Hookup
• Appliances: DishwasherDryerMicrowaveRangeRefrigeratorWasher
• Laundry: Inside
• Basement: None
• A/C: None
• Heating: Baseboard
• Fireplace: FireplaceFireplaces: 1

Exterior

• Style: CabinFarmhouseMini Estate
• Parking: AttachedGarageParking spaces: 10

Location

• Originating MLS: onekey2
• School District: Arlington
• County: Dutchess County

Lot

• Zoning: 134400-6463-02-782662-0000

Utilities

• Utilities: Electricity ConnectedTrash Collection Private
• Water: Well
• Sewer: Septic Tank

Financial

• Source: onekey2