367 Prospect Hill Road • Pine Plains, NY 12567

$8,475,000 Beds: 6 • Baths: 7 full 1 partial • Sq. Feet: 12418 • MLS ID: 882588 • Subdivision:School Dist: Pine Plains
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. View this listing at: http://www.laffey.com/lid=179410382

Property Features

  • Garage: 6
  • Taxes: $41,116
  • Basement: Yes
  • Wooded: Yes
  • Exterior: Log
  • Special View Info: Mountain(s),Panoramic,Park/Greenbelt,Trees/Woods
  • Lot Size: 170.00 Acres
  • Heating: Ducts,Forced Air,Propane,Other
  • Cooling: Central Air
  • Year Built: 1991
  • Fireplaces: 6
  • Water: Well
  • Sewer: Septic Tank
  • On Market Date: 2025-07-01
  • Appliances: Dishwasher,Dryer,Exhaust Fan,Freezer,Gas Cooktop,Gas Oven,Gas Range,Refrigerator,Washer
  • Basement: Partial
  • Exterior Features: Basketball Court,Fire Pit,Garden,Other,Rain Gutters,Tennis Court(s)
  • Fireplace Features: Bedroom,Family Room,Living Room,Wood Burning
  • Fireplace Y/N: Yes
  • Flooring: Hardwood,Wood
  • GarageY/N: Yes
  • Interior Features: First Floor Bedroom,First Floor Full Bath,Beamed Ceilings,Breakfast Bar,Built-in Features,Cathedral Ceiling(s),Ceiling Fan(s),Chefs Kitchen,Dry Bar,Eat-in Kitchen,Entrance Foyer,High Ceilings,High Speed Internet,Kitchen Island,Primary Bathroom,Natural Woodwork,Open Floorplan,Open Kitchen,Original Details,Other,Storage,Walk Through Kitchen,Walk-In Closet(s),Washer/Dryer Hookup
  • Laundry: Laundry Room
  • Lot Features: Cleared,Garden,Landscaped,Other,Part Wooded,Private,Rolling Slope,Secluded,Sloped,Views,Waterfront,Wooded
  • Attic: Unfinished
  • Other Structures: Barn(s),Garage(s),Guest House,Outbuilding,Residence,Shed(s),Workshop
  • Parking Features: Detached
  • Patio And Porch: Covered,Deck,Porch,Wrap Around
  • Rental Term: Monthly
  • Rooms Total: 17
  • Utilities: Trash Collection Private,Underground Utilities
  • Waterfront Features: Pond

School Information

  • High School: Stissing Mountain Jr/Sr High School
  • Middle School: Stissing Mountain Junior/Senior High School
  • Elementary School: Seymour Smith Intermediate Lrn Ctr
  • School District: Pine Plains
Printed March 21, 2026


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