161 Whalesback Road, Red Hook, NY 12571
Local realty services provided by:ERA Caputo Realty



161 Whalesback Road,Red Hook, NY 12571
$1,799,000
- 5 Beds
- 5 Baths
- 5,490 sq. ft.
- Single family
- Pending
Listed by:ann c. stettner
Office:neil charles real estate, llc.
MLS#:885582
Source:One Key MLS
Price summary
- Price:$1,799,000
- Price per sq. ft.:$327.69
About this home
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.
Contact an agent
Home facts
- Year built:1900
- Listing Id #:885582
- Added:37 day(s) ago
- Updated:August 01, 2025 at 07:40 AM
Rooms and interior
- Bedrooms:5
- Total bathrooms:5
- Full bathrooms:4
- Half bathrooms:1
- Living area:5,490 sq. ft.
Heating and cooling
- Cooling:Central Air
- Heating:Baseboard, Hot Water, Propane, Radiant
Structure and exterior
- Year built:1900
- Building area:5,490 sq. ft.
- Lot area:15.1 Acres
Schools
- High school:Red Hook Senior High School
- Middle school:Linden Avenue Middle School
- Elementary school:Mill Road-Primary Grades
Utilities
- Water:Well
- Sewer:Septic Tank
Finances and disclosures
- Price:$1,799,000
- Price per sq. ft.:$327.69
- Tax amount:$20,586 (2024)
New listings near 161 Whalesback Road
- New$189,900Active3 Acres
109 Deer Run Road, Red Hook, NY 12571
MLS# 899115Listed by: HOULIHAN LAWRENCE INC. - New$330,000Active2 beds 1 baths996 sq. ft.
74 Hapeman Hill, Red Hook, NY 12571
MLS# 900634Listed by: BHHS HUDSON VALLEY PROPERTIES - New$995,000Active5 beds 4 baths2,500 sq. ft.
7441 S Broadway, Red Hook, NY 12571
MLS# 899544Listed by: BHHS HUDSON VALLEY PROPERTIES - New$260,000Active5 Acres
TBD Deer Run Road, Red Hook, NY 12571
MLS# 898181Listed by: WEICHERT REALTORS - New$350,000Active2 beds 1 baths806 sq. ft.
82 Rokeby Road, Red Hook, NY 12571
MLS# 898768Listed by: K. FORTUNA REALTY, INC. - New$455,000Active3 beds 2 baths1,296 sq. ft.
96 Old Post N Road, Red Hook, NY 12571
MLS# 862118Listed by: BHHS HUDSON VALLEY PROPERTIES - New$65,000Active1.08 Acres
Beaver Rd (jackson Crs), Red Hook, NY 12571
MLS# 897150Listed by: COLDWELL BANKER VILLAGE GREEN - $165,000Pending1.6 Acres
25 Fraleigh Lane, Red Hook, NY 12571
MLS# 896127Listed by: MARGARET MONDELLO REAL ESTATE - $299,900Active3 beds 1 baths967 sq. ft.
10 Amherst Road, Red Hook, NY 12571
MLS# 895459Listed by: COLDWELL BANKER ADVISOR REALTY - $639,000Active4 beds 3 baths2,300 sq. ft.
297 Turkey Hill Road, Red Hook, NY 12571
MLS# 894072Listed by: MONDELLO UPSTATE PROPERTIES