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101 Drake Road, 
Pleasant Valley, NY 12569

$1,375,000


3

Beds


3

Baths


2,820

Sq Ft


Single Family

Active

Listed by

Jake Garay

Serhant LLC.

Last updated:

February 11, 2026, 12:41 PM

MLS#

951502

Source:

OneKey MLS

About This Home

101 Drake Road

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.

Home Facts

Single Family

3 Baths

3 Bedrooms

Built in 1900

Price Summary

1,375,000

$487 per Sq. Ft.

MLS #:

951502

Last Updated:

February 11, 2026, 12:41 PM

Added:

a month ago


Rooms & Interior

Bedrooms

Total Bedrooms:

3

Bathrooms

Total Bathrooms:

3

Full Bathrooms:

2

Interior

Living Area:

2,820 Sq. Ft.


Structure

Structure

Architectural Style:

Farmhouse, Mini Estate

Building Area:

2,820 Sq. Ft.

Year Built:

1900


Lot

Lot Size (Sq. Ft):

128,066


Finances & Disclosures

Finances

Price:

$1,375,000

Price per Sq. Ft:

$487 per Sq. Ft.

Source:OneKey MLS
Copyright 2026 OneKey MLS. All rights reserved. Listings courtesy of OneKey MLS as distributed by MLS GRID . OneKey MLS provides content displayed here (“provided content”) on an “as is” basis and makes no representations or warranties regarding the provided content, including, but not limited to those of non-infringement, timeliness, accuracy, or completeness. Individuals and companies using information presented are responsible for verification and validation of information they utilize and present to their customers and clients. OneKey MLS will not be liable for any damage or loss resulting from use of the provided content or the products available through Portals, IDX, VOW, and/or Syndication. Recipients of this information shall not resell, redistribute, reproduce, modify, or otherwise copy any portion thereof without the expressed written consent of OneKey MLS.

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Contact an Agent

Yes, I would like more information. Please use and/or share my information with a Coldwell Banker ® affiliated agent to contact me about my real estate needs. By clicking Contact, I request to be contacted by phone or text message and consent to being contacted by automated means. I understand that my consent to receive calls or texts is not a condition of purchasing any property, goods, or services. Alternatively, I understand that I can access real estate services by email or I can contact the agent myself.

If a Coldwell Banker affiliated agent is not available in the area where I need assistance, I agree to be contacted by a real estate agent affiliated with another brand owned or licensed by Anywhere Real Estate (BHGRE®, CENTURY 21®, Corcoran®, ERA®, or Sotheby's International Realty®). I acknowledge that I have read and agree to the terms of use and privacy notice.