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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
    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.
    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#: 885582MLS Logo
    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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