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101 Drake Road

Pleasant Valley, NY 12569
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Bed 3

Bed

Bath 3

Bath

SqFt2,820

Sqft

Acres2.94

Acres(Lot)

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.

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Detail Ic Property Details

Property Type : Residential

Price : $1,195,000

AD Id : 74916145

MLS Id : 951502

Beds : 3

Lot Size : 2.94 Acres

Living Area Size : 2,820

Year Built : 1900

Garage : 1

County : Dutchess

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Feature Features

  • Bedroom Information

    Total beds: 3

    Bathroom Information

    Total Baths: 3 Full Baths: 2 Half Baths: 1

    Room Information

    Rooms Total: 9 Basement: None
  • Interior Features

    Beamed Ceilings, Built-in Features, Eat-in Kitchen, High Ceilings, High Speed Internet, Open Floorplan, Recessed Lighting, Smart Thermostat, Storage, Walk-In Closet(s) Appliances: Dishwasher, Dryer, Microwave, Range, Refrigerator, Washer Laundry Features: Inside
  • Heating & Cooling

    Has Heating: Yes Heating: Baseboard Cooling: None

  • Building Information

    Year Built: 1900 Construction Materials: Frame Pool Features: Private Private Pool: Yes

  • Lot Information

    Lot Size Acres: 2.94 Lot Size Square Feet: 128066

  • Listing Price Information

    Listing Price: $1195000 Original Price: $1375000

  • Tax Information

    Parcel Number: 134400-6463-02-782662-0000 Annual Tax: $22775.2

  • Parking Information

    Parking Total: 10 Attached, Garage

    Garage Information

    Has Garage: Yes Has Attached Garage: Yes Garage Space: 1

  • School Information

    Elementary School: Traver Road Primary School
    Junior High School: TITUSVILLE INTERMEDIATE
    Senior High School: Arlington High School
  • Utility Information

    Electricity Connected
  • Location Information

    WaterSource: Private, Well
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Nearby Home Value

Address Estimate Bed Bath Sq. Ft Lot Size
32 Cole Road, Pleasant Valley, NY, 12569 $800,000 4 3 3,263 3,263 SqFt
2846 Route 82, Pleasant Valley, NY, 12569 $389,000 2 1 1,508 1,508 SqFt
2846 Route 82, Pleasant Valley, NY, 12569 $389,000 2 1 1,508 1,508 SqFt
176 Downing Road, Pleasant Valley, NY, 12569 $495,000 3 2 1,824 1,824 SqFt
8 Trillium Road, Pleasant Valley, NY, 12569 $499,000 3 2 1,738 1,738 SqFt
145 Drake Road, Pleasant Valley, NY, 12569 $595,000 2 2 1,368 1,368 SqFt
21 Straub Drive, Pleasant Valley, NY, 12569 $675,000 4 4 3,400 3,400 SqFt
41 Meddaugh Road, Pleasant Valley, NY, 12569 $695,000 4 3 3,019 3,019 SqFt
60 Traver Road, Pleasant Valley, NY, 12569 $849,999 4 3 3,114 3,114 SqFt
47 Mountain View Drive, Pleasant Valley, NY, 12569 $475,000 4 3 2,356 2,356 SqFt

The data relating to real estate for sale on this website comes in part from the Internet Data exchange of OneKey MLS. IDX information is provided exclusively for consumers' personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Information deemed reliable but not guaranteed. Copyright © 2026 OneKey MLS. All Rights Reserved

ByOwner last updated this listing 07/19/2026 @ 12:48

MLS: 951502 LISTED BY: Jake Garay, Serhant LLC 646-480-7665 SOURCE: OneKey MLS

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