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101 Drake Road
101 Drake Road
101 Drake Road
101 Drake Road
101 Drake Road
101 Drake Road
101 Drake Road
101 Drake Road
101 Drake Road
101 Drake Road
101 Drake Road
101 Drake Road
101 Drake Road
101 Drake Road
101 Drake Road
101 Drake Road
101 Drake Road
101 Drake Road
101 Drake Road
101 Drake Road
101 Drake Road
101 Drake Road
101 Drake Road
101 Drake Road
101 Drake Road
101 Drake Road
101 Drake Road
101 Drake Road
101 Drake Road
101 Drake Road
101 Drake Road
101 Drake Road
101 Drake Road
101 Drake Road
101 Drake Road
101 Drake Road
101 Drake Road
101 Drake Road
101 Drake Road
101 Drake Road
101 Drake Road
101 Drake Road
101 Drake Road
101 Drake Road
101 Drake Road
101 Drake Road
101 Drake Road
Courtesy of Serhant LLC, Jake Garay Listing Contact: 9147722603 

101 Drake Road

101 Drake Road, Pleasant Valley, NY 12569

$1,195,000

  • 3 BEDS
  • 2 FULL BATHS
  • 1 HALF BATH
  • 2,820 Sq.Ft.

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.

Overview

Property Type
Residential
Location
101 Drake Road, Pleasant Valley, NY 12569
MLS ID
951502
Listing Last Updated

Property Features & Amenities

Interior

Total Bedrooms
3
Full Bathrooms
2
Half Bathrooms
1
Appliances
Dishwasher, Dryer, Microwave, Range, Refrigerator, Washer
Other Interior Features
Beamed Ceilings, Built-in Features, Eat-in Kitchen, High Ceilings, High Speed Internet, Open Floorplan, Open Kitchen, Original Details, Primary Bathroom, Recessed Lighting, Smart Thermostat, Storage, Walk-In Closet(s), Washer/Dryer Hookup

Exterior

Garage Spaces
1.0
Water Source
Well
Utilities
Electricity Connected, Trash Collection Private
Parking
Attached, Garage
Heat Type
Baseboard
Air Conditioning
None
Sewer
Septic Tank
Substructure
Pillar/Post/Pier

Details

Architecture Styles
A-Frame, Barndominium, Cabin, Carriage House, Farmhouse, Mini Estate

Financial

Price
$1,195,000
Real Estate Tax
$22,775/yr

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Exclusive Listing Agents

Jake Garay

Founding Agent || SERHANT. Hudson Valley & CEO, The Garay Team

(914) 772-2603
101 Drake Road

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    Jake Garay
    Jake Garay
    Founding Agent || SERHANT. Hudson Valley & CEO, The Garay Team
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