Leave a Message

Thank you for your message. We will be in touch with you shortly.

Explore Our Properties

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 Status
For Sale
Lot Size
2.94 Acres
MLS ID
951502
Property Type
Residential
Year Built
1900

Features & Amenities

Architecture Styles
A-Frame, Barndominium, Cabin, Carriage House, Farmhouse, Mini Estate
Garage Spaces
1.0
Water Source
Well
Utilities
Electricity Connected, Trash Collection Private
Parking
Attached, Garage
Heat Type
Baseboard
Air Conditioning
None
Laundry Room
Inside
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
Sewer
Septic Tank
Substructure
Pillar/Post/Pier
Elementary School
Traver Road Primary School
Middle School
TITUSVILLE INTERMEDIATE
High School
Arlington High School
School District
Arlington
Sales Price
$1,195,000
Real Estate Tax
$22,775/yr

Downloads

101 Drake Road

Schedule a Tour

We would love to help you see this beautiful home! As a full-service brokerage, we can help you tour. Please submit an offer, and answer questions about the buying process.

Thank you

for your interest in 101 Drake Road, Pleasant Valley, NY 12569

101 Drake Road
Navigate

Mortgage Calculator

Estimate your monthly mortgage payment, including the principal and interest, property taxes, and HOA. Adjust the values to generate a more accurate rate.
$0,000 Your Payment 20 15 65
$0,000 Your Payment

I'm Interested In

101 Drake Road

or
  • CallJake Garay

    License #10301216829

    (914) 772-2603
  • Browse Our

    Featured Properties

    • 213 Greenhaven Road For Sale

      $24,875,000

      213 Greenhaven Road, Poughquag, NY 12570

      Courtesy of Serhant LLC

    • 15 Wild Turkey Road For Sale

      $7,750,000

      15 Wild Turkey Road, Lake George, NY 12845

      Courtesy of Serhant LLC

      • 4 Beds
      • 4 Baths
      • 5,283 Sq.Ft.
    • 618 Quaker Hill Road For Sale

      $4,750,000

      618 Quaker Hill Road, Pawling, NY 12564

      Courtesy of Serhant LLC

      • 8 Beds
      • 13 Baths
      • 15,000 Sq.Ft.
    • 30 High Ridge Road For Sale

      $3,995,000

      30 High Ridge Road, Warwick, NY 10990

      Courtesy of Serhant LLC

      • 3 Beds
      • 6 Baths
      • 6,668 Sq.Ft.
    • 51 Redder Road For Sale

      $3,500,000

      51 Redder Road, Pine Bush, NY 12566

      Courtesy of Serhant LLC

      • 15,000 Sq.Ft.
    • 19 Greentree Lane For Sale

      $3,400,000

      19 Greentree Lane, Chester, NY 10918

      Courtesy of Serhant LLC

      • 4 Beds
      • 4 Baths
      • 7,750 Sq.Ft.
    • 95 Jersey Avenue For Sale

      $2,800,000

      95 Jersey Avenue, Greenwood Lake, NY 10925

      Courtesy of Serhant LLC

      • 5 Beds
      • 4 Baths
      • 5,920 Sq.Ft.
    • The Ridge on 214 Coming Soon

      Price Upon Request

      2595 Route 214, Lanesville, NY 12450

      • 3 Beds
      • 2 Baths
      • 1,777 Sq.Ft.
    • 127 Boutonville Road For Sale

      $2,500,000

      127 Boutonville Road, Pound Ridge, NY 10576

      Courtesy of Serhant LLC

      • 4 Beds
      • 5 Baths
      • 5,575 Sq.Ft.
    • 3 Leon Macglashan Road For Sale

      $2,495,000

      3 Leon Macglashan Road, Windham, NY 12496

      • 8 Beds
      • 4 Baths
      • 3,350 Sq.Ft.
    • 3 Leon Macglashan Road For Sale

      $2,495,000

      3 Leon Macglashan Road, Windham, NY 12496

      Courtesy of Serhant LLC

      • 8 Beds
      • 4 Baths
      • 3,350 Sq.Ft.
    • 218 Carriage Way For Sale

      $2,400,000

      218 Carriage Way, Hyde Park, NY 12538

      Courtesy of Serhant LLC

      • 4 Beds
      • 5 Baths
      • 4,648 Sq.Ft.
    • 212 Carriage Way Coming Soon

      $2,000,000

      212 Carriage Way, Hyde Park, NY 12538

      • 4 Beds
      • 5 Baths
      • 4,648 Sq.Ft.
    • Bellwether Farm For Sale

      $1,995,000

      310 Mt Holly Rd, Katonah, NY 10536

      • 7 Beds
      • 6 Baths
      • 3,300 Sq.Ft.
    • 212 Carriage Way For Sale

      $1,950,000

      212 Carriage Way, Hyde Park, NY 12538

      Courtesy of Serhant LLC

      • 4 Beds
      • 5 Baths
      • 4,648 Sq.Ft.
    • 15 Somers Hills Road For Sale

      $1,875,000

      15 Somers Hills Road, Carmel, NY 10512

      Courtesy of Serhant LLC

      • 4 Beds
      • 6 Baths
      • 5,460 Sq.Ft.
    • Exclusive Listing For Sale
    • 3 Bristol Drive For Sale

      $1,799,999

      3 Bristol Drive, Middletown, NY 10941

      • 5 Beds
      • 9 Baths
      • 7,794 Sq.Ft.
    • 5 - 7 Downer Lane For Sale

      $1,700,000

      5 - 7 Downer Lane, Woodstock, NY 12498

      Courtesy of Serhant LLC

      • 5 Beds
      • 5 Baths
      • 4,628 Sq.Ft.
    • 1 Kings Grant Way For Sale

      $1,599,000

      1 Kings Grant Way, Briarcliff Manor, NY 10510

      Courtesy of Serhant LLC

      • 4 Beds
      • 3 Baths
      • 4,928 Sq.Ft.
    • 162 Crum Elbow Road For Sale

      $1,575,000

      162 Crum Elbow Road, Hyde Park, NY 12538

      Courtesy of Serhant LLC

      • 5 Beds
      • 6 Baths
      • 5,698 Sq.Ft.
    • 169 Albany Avenue For Sale

      $1,500,000

      169 Albany Avenue, Kingston, NY 12401

      Courtesy of Serhant LLC

      • 5 Beds
      • 5 Baths
      • 4,962 Sq.Ft.
    • 19 Blues Quarry For Sale

      $1,350,000

      19 Blues Quarry, Woodstock, NY 12498

      Courtesy of Serhant LLC

      • 4 Beds
      • 4 Baths
      • 2,613 Sq.Ft.
    • 17 Meadow Crest Drive For Sale

      $1,300,000

      17 Meadow Crest Drive, Mahopac, NY 10541

      Courtesy of Serhant LLC

      • 4 Beds
      • 4 Baths
      • 3,342 Sq.Ft.
    • 327 Phillips Road For Sale

      $1,250,000

      327 Phillips Road, Saugerties, NY 12477

      Courtesy of Serhant LLC

    • 5 Downer Lane For Sale

      $1,200,000

      5 Downer Lane, Woodstock, NY 12498

      Courtesy of Serhant LLC

      • 4 Beds
      • 4 Baths
      • 3,172 Sq.Ft.
    • 101 Drake Road For Sale

      $1,195,000

      101 Drake Road, Pleasant Valley, NY 12569

      Courtesy of Serhant LLC

      • 3 Beds
      • 3 Baths
      • 2,820 Sq.Ft.
    • 326 Ralph Vedder Road For Sale

      $1,000,000

      326 Ralph Vedder Road, Saugerties, NY 12477

      • 5 Beds
      • 4 Baths
      • 2,476 Sq.Ft.
    • Traver Hollow For Sale

      $970,000

      23 Traver Hollow Road, Boiceville, NY 12412

      • 3 Beds
      • 3 Baths
      • 2,100 Sq.Ft.
    • 116 Valleyview Road For Sale

      $959,000

      116 Valleyview Road, Irvington, NY 10533

      Courtesy of Serhant LLC

      • 3 Beds
      • 3 Baths
      • 2,480 Sq.Ft.
    • 10 Eastman Terrace For Sale

      $950,000

      10 Eastman Terrace, Poughkeepsie, NY 12601

      Courtesy of Serhant LLC

      • 4,488 Sq.Ft.
    • 23 Traver Hollow Road For Sale

      $945,000

      23 Traver Hollow Road, Boiceville, NY 12412

      • 3 Beds
      • 3 Baths
      • 2,100 Sq.Ft.
    • 20 Division Street For Sale

      $899,000

      20 Division Street, Cold Spring, NY 10516

      Courtesy of Serhant LLC

      • 4 Beds
      • 3 Baths
      • 2,002 Sq.Ft.
    • 21 Woodland Lane For Sale

      $875,000

      21 Woodland Lane, Palenville, NY 12463

      Courtesy of Serhant LLC

      • 3 Beds
      • 2 Baths
      • 2,028 Sq.Ft.
    • 30 Coleman Drive For Sale

      $875,000

      30 Coleman Drive, Campbell Hall, NY 10916

      Courtesy of Serhant LLC

      • 3 Beds
      • 3 Baths
      • 2,104 Sq.Ft.
    • 168 Cooper Lake Road For Sale

      $865,000

      168 Cooper Lake Road, Woodstock, NY 12498

      • 3 Beds
      • 3 Baths
      • 2,264 Sq.Ft.
    • 25 Ridge Road For Sale

      $865,000

      25 Ridge Road, East Chatham, NY 12060

      • 3 Beds
      • 3 Baths
      • 2,623 Sq.Ft.
    • 9 Homestead Lane For Sale

      $699,000

      9 Homestead Lane, New City, NY 10956

      • 3 Beds
      • 2 Baths
      • 1,638 Sq.Ft.
    • 210 Cherrytown Road For Sale

      $695,000

      210 Cherrytown Road, Kerhonkson, NY 12446

      Courtesy of Serhant LLC

    • Shovel-Ready Sanctuary For Sale

      $695,000

      83 Jansen Road, New Paltz, NY 12561

    • 120 Old Westbrookville Road For Sale

      $675,000

      120 Old Westbrookville Road, Wurtsboro, NY 12790

      Courtesy of Serhant LLC

      • 4 Beds
      • 3 Baths
      • 2,395 Sq.Ft.
    • 18 English Way For Sale

      $650,000

      18 English Way, Pleasant Valley, NY 12569

      Courtesy of Serhant LLC

      • 4 Beds
      • 3 Baths
      • 3,078 Sq.Ft.
    • 62 Riverview Mary Powell For Sale

      $650,000

      62 Riverview Mary Powell, Port Ewen, NY 12429

      Courtesy of Serhant LLC

      • 2 Beds
      • 3 Baths
      • 2,168 Sq.Ft.
    • 250 Highview Road For Sale

      $599,900

      250 Highview Road, Dover Plains, NY 12522

      Courtesy of Serhant LLC

      • 3 Beds
      • 4 Baths
      • 2,737 Sq.Ft.
    • 26 Bowdoin Lane For Sale

      $519,000

      26 Bowdoin Lane, Wappingers Falls, NY 12590

      Courtesy of Serhant LLC

      • 4 Beds
      • 2 Baths
      • 1,596 Sq.Ft.
    • 12 Talbot Drive For Sale

      $518,900

      12 Talbot Drive, Pleasant Valley, NY 12569

      Courtesy of Serhant LLC

      • 3 Beds
      • 2 Baths
      • 1,928 Sq.Ft.
    • 106 Main Street For Sale

      $510,000

      106 Main Street, Kingston, NY 12401

      Courtesy of Serhant LLC

      • 3,031 Sq.Ft.
    • 19 Miron Drive For Sale

      $509,000

      19 Miron Drive, Poughkeepsie, NY 12603

      Courtesy of Serhant LLC

      • 4 Beds
      • 3 Baths
      • 1,924 Sq.Ft.
    • 175 Nevis Road For Sale

      $460,000

      175 Nevis Road, Tivoli, NY 12583

      Courtesy of Serhant LLC

      • 2 Beds
      • 2 Baths
      • 1,606 Sq.Ft.
    • Exclusive Listing For Sale
    View All

    Follow Us On Instagram