Listing photo for 101 Drake Road, Pleasant Valley, NY
Listing photo for 101 Drake Road, Pleasant Valley, NY
Listing photo for 101 Drake Road, Pleasant Valley, NY
Listing photo for 101 Drake Road, Pleasant Valley, NY
Listing photo for 101 Drake Road, Pleasant Valley, NY
Listing photo for 101 Drake Road, Pleasant Valley, NY
Listing photo for 101 Drake Road, Pleasant Valley, NY
Listing photo for 101 Drake Road, Pleasant Valley, NY
Listing photo for 101 Drake Road, Pleasant Valley, NY
Listing photo for 101 Drake Road, Pleasant Valley, NY
Listing photo for 101 Drake Road, Pleasant Valley, NY
Listing photo for 101 Drake Road, Pleasant Valley, NY
Listing photo for 101 Drake Road, Pleasant Valley, NY
Listing photo for 101 Drake Road, Pleasant Valley, NY
Listing photo for 101 Drake Road, Pleasant Valley, NY
Listing photo for 101 Drake Road, Pleasant Valley, NY
Listing photo for 101 Drake Road, Pleasant Valley, NY
Listing photo for 101 Drake Road, Pleasant Valley, NY
Listing photo for 101 Drake Road, Pleasant Valley, NY
Listing photo for 101 Drake Road, Pleasant Valley, NY
Listing photo for 101 Drake Road, Pleasant Valley, NY
Listing photo for 101 Drake Road, Pleasant Valley, NY
Listing photo for 101 Drake Road, Pleasant Valley, NY
Listing photo for 101 Drake Road, Pleasant Valley, NY
Listing photo for 101 Drake Road, Pleasant Valley, NY
Listing photo for 101 Drake Road, Pleasant Valley, NY
Listing photo for 101 Drake Road, Pleasant Valley, NY
Listing photo for 101 Drake Road, Pleasant Valley, NY
Listing photo for 101 Drake Road, Pleasant Valley, NY
Listing photo for 101 Drake Road, Pleasant Valley, NY
Listing photo for 101 Drake Road, Pleasant Valley, NY
Listing photo for 101 Drake Road, Pleasant Valley, NY
Listing photo for 101 Drake Road, Pleasant Valley, NY
Listing photo for 101 Drake Road, Pleasant Valley, NY
Listing photo for 101 Drake Road, Pleasant Valley, NY
Listing photo for 101 Drake Road, Pleasant Valley, NY
Listing photo for 101 Drake Road, Pleasant Valley, NY
Listing photo for 101 Drake Road, Pleasant Valley, NY
Listing photo for 101 Drake Road, Pleasant Valley, NY
Listing photo for 101 Drake Road, Pleasant Valley, NY
Listing photo for 101 Drake Road, Pleasant Valley, NY
Listing photo for 101 Drake Road, Pleasant Valley, NY
Listing photo for 101 Drake Road, Pleasant Valley, NY
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101 Drake Road,

Pleasant Valley, NY

$1,375,000

3 Beds
3 Baths
2,820 Sqft
2.94 Acres
1 Garages

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.

Facts & Features
MLS® # 951502
Price $1,375,000
Bedrooms 3
Bathrooms 3.00
Full Baths 2
Half Baths 1
Square Footage 2,820
Acres 2.94
Year Built 1900
Type Residential
Sub-Type Single Family Residence
Style Cabin, Farmhouse, Mini Estate
Status Active
MLS hgmls
Community Information
Address 101 Drake Road
City Pleasant Valley
County Dutchess
State NY
Zip Code 12569
Amenities
Utilities Electricity Connected, Trash Collection Private
Parking Spaces 10
Parking Attached, Garage
# of Garages 1
Is Waterfront No
Has Pool Yes
Interior
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
Appliances Dishwasher, Dryer, Microwave, Range, Refrigerator, Washer
Heating Baseboard
Cooling None
Has Basement Yes
Basement None
Fireplace Yes
# of Fireplaces 1
Exterior
Construction Frame
School Information
District Arlington
Elementary Traver Road Primary School
Middle TITUSVILLE INTERMEDIATE
High Arlington High School
Additional Information
Date Listed February 10th, 2026
Days on Market 67
Short Sale No
RE / Bank Owned No
Listing Details
Listing Courtesy of Serhant LLC
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Listing information last updated on April 19th, 2026 at 12:50am EDT.