367 Prospect Hill Road, Pine Plains, NY 12567

• 6 beds |
• 8 baths |
• 12,418 sqft

Property Description

First time on the market! This magnificent 170-acre Modern Adirondack-styled estate near Millbrook, designed by architect Lloyd Taft, features a main house and three elegant guest cabins. Built by a third-generation builder of camps in upstate New York and the Thousand Islands, the cabin serves as the centerpiece of the compound. Meticulously maintained and tailor-made for year-round recreation, the property offers spectacular panoramic views of the Catskills and Taconic Hills from sunrise to sunset. With hand-hewn luxury reminiscent of Ralph Lauren’s aesthetic, the log-and-stone main residence features wraparound porches, a great room with a dramatic stone fireplace, a chef’s eat-in kitchen with Sub-Zero and Wolf appliances, a media room, a billiard room, and a luxurious primary suite with a fireplace and sunset terrace. The main house can accommodate ten people. Each of the three guest cabins, connected by a breezeway, features a fireplace, stone shower, kitchenette, and porch. In total, the guest quarters can accommodate twelve. Incredible amenities include a triple-height sports barn with an indoor sport court featuring pickleball, basketball, badminton, volleyball, a full gym, and a bonus arcade area. In addition, the sports barn can easily be converted into a large-format home theater. Additional outdoor features include an elevated paddle/pickleball court, a fillable freshwater swimming hole, a stocked pond, a full football/soccer field, six heated wildlife-watching perches, hiking trails, and an orchard with apples, peaches, sweet and sour cherry trees, blueberries, raspberries, and a cutting garden with a firepit. The compound also includes a party barn, a fish and game room, a separate office, and a grassy courtyard for croquet, bocce, and picnics. Ninety acres are professionally farmed by a local farmer. Ideally located close to Metro-North, Mashomack Preserve and Polo Club, Tamarack Preserve Club, and Orvis Sandanona, as well as the towns of Millbrook, Millerton, Pine Plains, Rhinebeck, and more. Unmatched privacy and resort-style living in the heart of the Hudson Valley.

Listing Status:

Active

Data Last Updated:

June 26, 2026 at 6:22PM

Listing Office:

Houlihan Lawrence Inc. : 845-677-6161

MLS ID:

882588

Interior

• General: First Floor BedroomFirst Floor Full BathBeamed CeilingsBreakfast BarBuilt-in FeaturesCathedral Ceiling(s)Ceiling Fan(s)Chefs KitchenDry BarEat-in KitchenEntrance FoyerHigh CeilingsHigh Speed InternetKitchen IslandPrimary BathroomNatural WoodworkOpen FloorplanOpen KitchenOriginal DetailsOtherStorageWalk Through KitchenWalk-In Closet(s)Washer/Dryer Hookup
• Rooms: Dining AreaHome OfficeLibrary/DenMedia Room
• Appliances: DishwasherDryerExhaust FanFreezerGas CooktopGas OvenGas RangeRefrigeratorWasher
• Laundry: Laundry Room
• Basement: Partial
• Flooring: HardwoodWood
• A/C: Central Air
• Heating: DuctsForced AirPropaneOther
• Fireplace: BedroomFamily RoomLiving RoomWood BurningFireplaceFireplaces: 6

Exterior

• General: Basketball CourtFire PitGardenOtherRain GuttersTennis Court(s)
• Style: CabinOther
• Other Structures: Barn(s)Garage(s)Guest HouseOutbuildingResidenceShed(s)WorkshopPorchWrap AroundDeckCovered
• Parking: Detached

Location

• Originating MLS: onekey2
• School District: Pine Plains
• County: Dutchess County

Lot

• View: Mountain(s)PanoramicPark/GreenbeltTrees/Woods

Utilities

• Utilities: Trash Collection PrivateUnderground Utilities
• Water: Well
• Sewer: Septic Tank

Financial

• Source: onekey2