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161 Whalesback Road, 
Red Hook, NY 12571

$1,799,000


5

Beds


5

Baths


5,490

Sq Ft


Single Family

Active

Listed by

Ann C. Stettner

Neil Charles Real Estate, LLC.

Last updated:

July 13, 2025, 11:39 PM

MLS#

885582

Source:

One Key MLS

About This Home

161 Whalesback Road

Don’t miss this rare opportunity to own a breathtaking, fully renovated 5,500 sq ft converted barn in the heart of the Hudson Valley. Nestled on 15 private, picturesque acres in the safety and tranquility of Red Hook, NY, this extraordinary 5-bedroom, 4.5-bathroom home seamlessly blends historic charm with modern luxury. Originally built in 1900, the barn has been thoughtfully transformed to preserve its character—soaring ceilings, exposed beams, and expansive open spaces—while offering every contemporary convenience. The home features a gracious open floor plan, oversized rooms, and a stunning in-ground pool with a flagstone patio, perfect for entertaining or peaceful country living. Designed for both relaxation and productivity, the home also includes plenty of room for an office, a spacious game/family room, gym, studio, or guest space. Whether you're working remotely, hosting family and friends, or simply unwinding, this home offers space for every lifestyle. Set in the center of equestrian country, this location offers unrivaled access to world-class destinations including Mashomack Preserve Club, Tamarack Preserve, and several notable new clubs emerging in the area. Families will appreciate proximity to top-tier public and private schools, a variety of excellent children’s camps, and some of the best skiing in the region. The vibrant local culture is further enriched by nearby Bard and Vassar Colleges, bringing world-class arts and events to your doorstep. Conveniently located just minutes from the charming villages of Red Hook and Rhinebeck, 20 minutes to Hudson and Pine Plains, 30 minutes to Millbrook, and less than an hour to the Berkshires. You're also just 10 minutes from the Amtrak station with direct service to NYC, and under two hours away by car. This is more than a home—it’s a lifestyle.

Home Facts

Single Family

5 Baths

5 Bedrooms

Built in 1900

Price Summary

1,799,000

$327 per Sq. Ft.

MLS #:

885582

Last Updated:

July 13, 2025, 11:39 PM

Added:

7 day(s) ago


Rooms & Interior

Bedrooms

Total Bedrooms:

5

Bathrooms

Total Bathrooms:

5

Full Bathrooms:

4

Interior

Living Area:

5,490 Sq. Ft.


Structure

Structure

Architectural Style:

Traditional

Building Area:

5,490 Sq. Ft.

Year Built:

1900


Lot

Lot Size (Sq. Ft):

657,756


Finances & Disclosures

Finances

Price:

$1,799,000

Price per Sq. Ft:

$327 per Sq. Ft.

Source:One Key MLS
Copyright 2025 OneKey MLS. All rights reserved. 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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