101 Drake Road, Pleasant Valley, NY 12569

• 3 beds |
• 3 baths |
• 2,820 sqft

Property Description

Historic Barn Conversion Meets Modern Luxury in the Hudson Valley Tucked away along a quiet country road in Pleasant Valley, this extraordinary estate offers a rare opportunity to own a meticulously restored 19th-century barn conversion that seamlessly blends historic character with modern luxury. Originally two separate barns, the property has been thoughtfully reimagined into a one-of-a-kind residence and companion pool house, creating a private retreat unlike anything else available in the Hudson Valley. From the moment you arrive, the home’s timeless architecture tells a story. Inside, soaring vaulted ceilings, original hand-hewn beams, wide-plank floors, and authentic post-and-beam construction showcase the craftsmanship of a bygone era while providing the comfort and functionality today’s buyers expect. Expansive walls of glass flood the interior with natural light and frame views of the surrounding countryside, creating a seamless connection between indoor and outdoor living. The main residence offers warm, inviting living spaces designed for both everyday living and entertaining. Rich architectural details, exposed timber framing, and carefully preserved historic elements create a sense of authenticity rarely found in modern construction. Every room balances rustic elegance with refined finishes, resulting in a home that feels both sophisticated and welcoming. Complementing the main residence is a beautifully converted barn pool house, providing exceptional flexibility for guests, entertaining, creative pursuits, or a private wellness retreat. The outdoor spaces are equally impressive, offering a peaceful setting to relax, gather, and enjoy the natural beauty of Dutchess County. Located just minutes from Millbrook, Rhinebeck, Poughkeepsie, and the region’s renowned farms, wineries, restaurants, and outdoor recreation, this property delivers the best of Hudson Valley living while remaining easily accessible to New York City. Whether you’re searching for a luxury barn conversion, a post-and-beam home, a historic country estate, or a weekend retreat in the Hudson Valley, 101 Drake Road represents a truly rare offering where history, architecture, and modern comfort come together in perfect balance.

Listing Status:

Active

Data Last Updated:

June 26, 2026 at 7:20AM

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: A-FrameBarndominiumCabinCarriage HouseFarmhouseMini 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