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.
Pending
$1,799,000
161 Whalesback Road, Red Hook, NY 12571
5beds
5,490sqft
Single Family Residence, Residential
Built in 1900
15.1 Acres Lot
$-- Zestimate®
$328/sqft
$-- HOA
What's special
Modern luxuryGuest spaceFlagstone patioOpen floor planConverted barnStunning in-ground poolOversized rooms
- 43 days
- on Zillow |
- 570 |
- 54 |
Zillow last checked: 8 hours ago
Listing updated: August 01, 2025 at 12:11am
Listing by:
Neil Charles Real Estate, LLC 845-266-8374,
Ann C. Stettner 917-660-3266
Source: OneKey® MLS,MLS#: 885582

Travel times
Facts & features
Interior
Bedrooms & bathrooms
- Bedrooms: 5
- Bathrooms: 5
- Full bathrooms: 4
- 1/2 bathrooms: 1
Primary bedroom
- Description: Stunning, light-filled large bedroom with radiant heat, large dressing room/closet and primary bath
- Level: Second
Bedroom 1
- Description: Currently set up as large bedroom suite with bathroom en suite and radiant heat throughout, but could be gym, family room, media room etc
- Level: First
Bedroom 3
- Description: Large bedroom with wood floors, and bathroom en suite
- Level: Second
Bedroom 4
- Description: Light-filled corner bedroom with new large bath en suite
- Level: Second
Bedroom 5
- Description: Nice bedroom with bathroom en suite
- Level: Second
Primary bathroom
- Description: Double sinks, large soaking tub, large stall shower, custom make up vanity, radiant heat
- Level: Second
Bathroom 1
- Description: Modern full bathroom on main floor in bonus suite
- Level: First
Bathroom 2
- Level: First
Bathroom 3
- Level: Second
Bathroom 4
- Level: Second
Bathroom 5
- Level: Second
Dining room
- Description: Wood floors, light-filled, high ceiling, open floor plan to kitchen
- Level: First
Family room
- Description: Wood floors, high ceiling, currently set up as game room with ping pong table
- Level: First
Kitchen
- Description: Light-filled, counter seating, center Island, new flooring with radiant heat, open floor plan
- Level: First
Laundry
- Description: Large laundry room
- Level: First
Living room
- Description: Large, light-filled living room with fireplace, high ceiling, wood floors and open floor plan
- Level: First
Office
- Level: Second
Office
- Level: First
Heating
- Baseboard, Hot Water, Propane, Radiant
Cooling
- Central Air
Appliances
- Included: Cooktop, Dishwasher, Dryer, Oven, Refrigerator, Stainless Steel Appliance(s), Washer
- Laundry: Laundry Room
Features
- First Floor Bedroom, First Floor Full Bath, Beamed Ceilings, Cathedral Ceiling(s), Ceiling Fan(s), Chefs Kitchen, Double Vanity, Eat-in Kitchen, Entrance Foyer, Formal Dining, High Speed Internet, His and Hers Closets, Kitchen Island, Open Floorplan, Original Details, Pantry, Primary Bathroom, Master Downstairs, Soaking Tub, Stone Counters
- Flooring: Carpet, Hardwood, Tile
- Basement: Partial,Storage Space,Unfinished,Walk-Out Access
- Attic: Partial,Pull Stairs,Unfinished
- Number of fireplaces: 1
- Fireplace features: Living Room, Wood Burning
Interior area
- Total structure area: 5,490
- Total interior livable area: 5,490 sqft
Property
Parking
- Total spaces: 8
- Parking features: Driveway, Garage, Off Street, Private
- Garage spaces: 4
- Has uncovered spaces: Yes
Features
- Levels: Two
- Patio & porch: Patio, Porch, Screened
- Exterior features: Garden
- Has private pool: Yes
- Pool features: In Ground
- Has view: Yes
- View description: Open, Park/Greenbelt
Lot
- Size: 15.1 Acres
- Features: Back Yard, Cleared, Front Yard, Garden, Landscaped, Level, Near School, Near Shops, Private, Views
- Residential vegetation: Partially Wooded
Details
- Additional structures: Garage(s)
- Parcel number: 1348896273000857130000
- Special conditions: None
- Other equipment: Generator
Construction
Type & style
- Home type: SingleFamily
- Architectural style: Other,Traditional
- Property subtype: Single Family Residence, Residential
Materials
- Blown-In Insulation, HardiPlank Type
- Foundation: Slab, Stone
Condition
- Updated/Remodeled
- Year built: 1900
Utilities & green energy
- Sewer: Septic Tank
- Utilities for property: Cable Available, Phone Available, Propane, Sewer Connected, Trash Collection Private, Water Connected
Community & HOA
Community
- Security: Security System, Smoke Detector(s)
HOA
- Has HOA: No
Location
- Region: Red Hook
Financial & listing details
- Price per square foot: $328/sqft
- Tax assessed value: $1,005,500
- Annual tax amount: $20,586
- Date on market: 7/8/2025
- Listing agreement: Exclusive Right To Sell
- Electric utility on property: Yes
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