$1,195,000
 $6,415 est/mo Sourced by Back At You

101 Drake Road,Pleasant Valley, NY 12569

Pleasant Valley, NY 12569

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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.

Details

MLS #951502
Listing TypeFor Sale
StyleHouse
Sub-TypeResale
StatusActive
Year1900
Days On Site197
Listing Provided BySerhant LLC | Jake Garay

Features

Bed(s)3
Bath(s) 3 Total
SQ Feet2,820
Garage1
PoolYes
Acreage2.94

Interior

CoolingNone
HeatingBaseboard
Interior FeaturesBeamed 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
AppliancesDishwasher, Dryer, Microwave, Range, Refrigerator, Washer

Exterior

Construction MaterialsFrame
Foundation DetailsPillar/Post/Pier

Parking

Garage Yes / NoYes
Parking FeaturesAttached, Garage

Utilities

UtilitiesElectricity Connected, Trash Collection Private
SewerSeptic Tank

Taxes

Tax Year2025
Tax Assessed Value540800
Tax Annual Amount22775.2

Area Information

StateNY
CountyDutchess County
CityPleasant Valley
Zip Code12569
School DistrictArlington High School
Elementary SchoolTraver Road Primary School
High SchoolArlington High School
Listing VS Median (in 12569)
Price:
$1,195,000
low | high
Med:
$495,000
100% of Average
sqft:
2,820
low | high
Med:
2,169
73.085106382979% of Average
$ / sqft:
$424
low | high
Med:
$228
96.14489834893% of Average
On site:
197
low | high
Med:
82
100% of Average
Sourced by Back At You

Market Activity 12569

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Learn More About This Property

StateNY
CountyDutchess County
CityPleasant Valley
Zip Code12569
School DistrictArlington High School
Elementary SchoolTraver Road Primary School
High SchoolArlington High School
Listing VS Median (in 12569)
Price:
$1,195,000
low | high
Med:
$495,000
100% of Average
sqft:
2,820
low | high
Med:
2,169
73.085106382979% of Average
$ / sqft:
$424
low | high
Med:
$228
96.14489834893% of Average
On site:
197
low | high
Med:
82
100% of Average
Sourced by Back At You
Listing Updated: August 17, 2026 at 8:01:28 AM PDT