$3,850,000

WhistleWood Farm A rare multi-use estate set on just under 40 acres in the heart of Rhinebeck, NY. Currently operating as a successful bed-and-breakfast, event venue, and horse boarding facility, WhistleWood Farm offers exceptional flexibility for both residential and commercial buyers seeking a true Hudson Valley destination property. Comprised of three parcels totaling… Read More nearly 40 acres, the property is equally suited as a private compound, gentleman’s farm, equestrian retreat, boutique hospitality venture, or wellness-focused escape. Existing hospitality and equestrian infrastructure provide a strong foundation for continued or expanded use. The main residence spans approximately 4,500 square feet and features 5 bedrooms, 5 full baths, and 2 kitchens—offering remarkable flexibility for private living, guest accommodations, or hospitality operations. Complementing the main house is an beautifully appointed 1,500-square-foot carriage house with three bedrooms and three baths, rich in character and perfectly suited for guests, extended stays, or expanded event and hospitality use. Walking trails through the woods create a rare sense of privacy and connection to the landscape just moments from the heart of Rhinebeck Village—with its celebrated dining, farm-to-table restaurants, boutiques, and nearby Amtrak access. For the tennis enthusiast, premier tennis facilities conveniently located next door further enhance the property’s lifestyle appeal. Open meadows, mature trees, and a coveted Village-adjacent setting make WhistleWood Farm a truly rare offering—equally compelling as a private estate, hospitality investment, or legacy property in the Hudson Valley. Additional features include solar power, further enhancing the property’s efficiency and long-term sustainability. HOME FEATURES: • Approx. 4,600-square-foot main residence • Five bedrooms • Multiple gathering and entertaining spaces • Apartment within the main house • Two kitchens • Beamed and cathedral ceilings • Fireplaces • Separate 1,500-square-foot carriage house • Two-bedroom, two-bath carriage house • Additional apartment above the barn • Country views from many rooms • Flexible layout for private residential • Minutes to Rhinebeck Village and Rhinecliff Amtrak LOT FEATURES: • Nearly 40 acres in Rhinebeck, New York • Original stone walls throughout the property • Seven fenced pastures and one paddock • Two ponds • Over two miles of walking and riding trails • Keep Safe fencing throughout • Grass riding ring • Riding arena with TravelRight footing • Mature trees and open meadows • Minutes to Rhinebeck Village and Rhinecliff Amtrak HORSE FACILITY FEATURES: • Up to 12 stalls • Southern pine stalls with rubber stall mats • Stalls configured as 12x12 or 12x24 • Dutch doors from each stall leading outdoors • Wash racks • Tractor barn with four bays • Grass riding ring • Riding arena with TravelRight footing • Seven pastures and one paddock • Keep Safe fencing throughout • Apartment above the barn for staff, guests, or caretakers Read Less

Listing Courtesy of Four Seasons Sothebys Intl.

Listing Snapshot

Days Online

142

Last Updated

Oct 12, 2026

Property Type

Single Family Residence

Beds

Full Baths

Partial Baths

Square Ft.

6,089

Lot Size

14.75 Acres

Year Built

1955

Property Tax

$23,471

MLS Number

1003365

Additional Details

Property Access

Frontage Type: County Road, Road Responsibility: Public Maintained Road

Appliances & Equipment

Dryer, Range, Refrigerator, Washer

Basement

Storage Space

Building

Built in 1955, Living area: 6089, Construction Materials: Wood Siding

Cooling

Wall/Window Unit(s)

Energy Saving

Energy Generation: Solar

Fence

Fenced, Wood

Fireplaces

1 fireplace

Floors

Wood

Foundation

Slab

Garage

2 spaces

Heating

Propane

Interior Features

First Floor Bedroom

Lot

39 acres, Dimensions: (3) Lots total

Parking

Covered, Detached, Garage, Parking Lot

Sewer

Septic Tank

Taxes

Additional parcels description:, Parcel Number: 135089-6270-00-794934-0000, Annual Amount: $23,470.6, Assessed Value: $1.7847e+06, Year: 2025

Utilities

Electricity Connected, Water Source: Well

Water Features

Pond

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