25 Winchell Trail, Pine Plains, NY 12567
OFF MARKET

25 Winchell Trail
Pine Plains, NY 12567

  • 5 Beds
  • 5 Baths
  • 5,935 sqft (on 28.84 acres)
5 Beds
5 Baths
5,935 sqft
(on 28.84 acres)

Local Information

Map showing home location
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-- mins to
Commute Destination

Description

Stretching across the top of 29 wildflower-blanketed acres on the southern ridge of Winchell Mountain, w/commanding Catskills views, lies High View Farm. Inspired by the rolling farmland & expansive blue skies of this very special part of the Hudson Valley, the Architectural & Interior Design duo HallidayGreer collaborated with Architect Graydon Yearick & LaGuardia Design Group Landscape Architects to create a one-of-a-kind living experience. Using sustainable natural materials & state-of-the-art building technology, High View Farm is a perfect synthesis of contemporary modernism & rural barn. Working primarily with local artisans, they have created the ultimate combination of comfort & understated luxury. Relying on the endless power of the sun & the constant, cool temperature of geothermal energy they've realized a passive, architecturally-inspired EcoLux compound that will excite and endure for generations.

The 5900 sf, 5 BR/5 BA main house has 3 primary suites and 2 additional ensuite guest rooms. The baths are all appointed with Waterworks fixtures & custom cabinets. The bedrooms, all with spectacular views, are generously proportioned with custom millwork closets with oak interiors. The kitchen is a chef's dream with an AGA Mercury induction stove, a Thermador fridge, an appliance pantry, 2 dishwashers, full butler's pantry with wine refrigeration, and a Miele integrated coffee system. The great room has a masonry fireplace & dining for 14 people. The ground floor has a Tonal Smart personal training machine, free weights, a yoga/stretching area, surround-sound cinema, and a cedar sauna. The piece-de-resistance is the four season indoor/outdoor room with a wood-burning fireplace-a dream for entertaining in a country home.

The 50x11ft. saltwater gunite infinity pool, w/sun-shelf & tub spa, overlooks Stissing Mtn. and has a pool house with a ''live'' green roof, full kitchen & bath, & lounge/sleeping area. It's united to the pool by floor-to-ceiling sliding glass panel doors running the length of the pool. A lovely fire pit area for cooler summer & autumn evenings is just past the pool and up the ridge from the built-in BBQ. Closer to the main house, with its own wood-burning built-in BBQ, is the Maple Grove; another idyllic outdoor moment for more elaborate summer parties & alfresco dining.

There are 2 add'l structures on the property. First, a 30x40 mortice & tenon barn w/pine & oak hand-hewn beams assembled by local Connecticut barn builders, with room for 2 cars, and a hayloft easily convertible to additional living space. Second, an atmospheric potting shed, inspired by an outbuilding on the grounds of the Parrish Art Museum in Southampton, NY made of pine & clad with perforated stainless steel...a sculptural solution to a utilitarian need.

Among the many eco-lux features are fumed white oak wide plank flooring, radiant floor heating, forced geothermal cooling to maintain absolute climate control, ultra-efficient top-quality windows throughout, sustainable radiata pine Abodo siding, and an aesthetically pleasing Tesla solar tile roof that generates almost 20KW of electricity-enough to power the whole property. It also has smart home features like programmable solar roof power generation distribution control, 3 car-charging connections, remote-controlled audio sound system, landscape lighting, window shades, security cameras & automated entry gates.

The home comes fully furnished w/bespoke soft furnishings, and fully outfitted, from luxurious sheets to elegant knife sets, all displaying the designers' impeccable style. The interiors blend European & American classical, modernist, & contemporary pieces (primarily sourced from local antique dealers & Hudson Valley craftsmen) in a palette that reflects the rich colors & textures of the surrounding landscape. High View Farm is a homage to the rich history and diversity of the area's rural farming community with an equally engaged commitment to the future
This property is off market, which means it's not currently listed for sale or rent on Trulia. This may be different from what's available on other websites or public sources. This description is from May 09, 2026

Home Highlights

Parking
2 Car Garage
Outdoor
Deck, Pool
A/C
Heating & Cooling
HOA
None
Price/Sqft
No Info
Listed
180+ days ago

Home Details for 25 Winchell Trail

Active Status

MLS Status: Closed

Interior Features

Interior Details
Basement: FinishedNumber of Rooms: 12Types of Rooms: Master Bedroom, Bedroom, Master Bathroom, Bathroom, Exercise Room, Great Room, Kitchen, Laundry, Media Room, Sauna
Beds & Baths
Number of Bedrooms: 5Number of Bathrooms: 5Number of Bathrooms (full): 5
Dimensions and Layout
Living Area: 5935 Square Feet
Appliances & Utilities
Appliances: Wine Refrigerator, Water Softener Owned, Water Purifier Owned, Washer/Dryer Stacked, Solar Hot Water, Induction Cooktop, ENERGY STAR Qualified Refrigerator, ENERGY STAR Qualified Washer, ENERGY STAR Qualified Freezer, ENERGY STAR Qualified Dryer, ENERGY STAR Qualified Dishwasher, ENERGY STAR Qualified Appliances, Dryer, Built-In Gas RangeDryerLaundry: Laundry Room
Heating & Cooling
Heating: Active Solar,Radiant FloorHas CoolingAir Conditioning: Central Air,GeothermalHas HeatingHeating Fuel: Active Solar
Fireplace & Spa
Number of Fireplaces: 2Fireplace: Fire Pit, Living Room, See RemarksSpa: Gunite, In GroundHas a FireplaceHas a Spa
Gas & Electric
Electric: 200+ Amp Service
Windows, Doors, Floors & Walls
Window: ENERGY STAR Qualified WindowsDoor: ENERGY STAR Qualified DoorsFlooring: Hardwood
Levels, Entrance, & Accessibility
Stories: 3Levels: Three Or MoreFloors: Hardwood
View
Has a ViewView: Mountain(s), Panoramic, Valley
Security
Security: Security Service

Exterior Features

Exterior Home Features
Roof: See RemarksPatio / Porch: DeckFencing: PerimeterOther Structures: Barn(s), Pool House, Shed(s)Foundation: Concrete Perimeter
Parking & Garage
Number of Garage Spaces: 2Number of Covered Spaces: 2No CarportHas a GarageHas an Attached GarageNo Open ParkingParking Spaces: 2Parking: Electric Gate,Electric Vehicle Charging Station(s)
Pool
Pool: Gunite, Heated, In Ground, Infinity, Pool Cover, Pool/Spa Combo, Salt WaterPool
Frontage
Road Surface Type: Gravel
Water & Sewer
Sewer: Private Sewer
Finished Area
Finished Area (above surface): 5484 Square FeetFinished Area (below surface): 451 Square Feet

Property Information

Year Built
Year Built: 2023
Property Type / Style
Property Type: ResidentialProperty Subtype: Single Family ResidenceArchitecture: Contemporary
Building
Construction Materials: Concrete, Wood SidingIs a New Construction
Property Information
Included in Sale: see remarksParcel Number: 972980

Price & Status

Price
List Price: $8,950,000
Status Change & Dates
Off Market Date: Mon May 19 2025

Location

Direction & Address
City: Pine Plains
School Information
Elementary School: Seymour Smith Elementary SchoolHigh School District: Pine Plains Central School District

Building

Building Area
Building Area: 5935 Square Feet

Lot Information

Lot Area: 28.84 Acres

Offer

Listing Terms: Cash, Conventional

Miscellaneous

BasementMls Number: 20243158Above Grade Unfinished Area: 5484
Last check for updates: about 16 hours ago
Listed by Gary Dimauro, (518) 755-3973
Four Seasons Sotheby's Int.
Bought with: Four Seasons Sotheby's Int.
Source: HVCRMLS, MLS#20243158

Price History for 25 Winchell Trail

DatePriceEventSource
07/03/2025$8,350,000Sold
HVCRMLS #20243158
05/19/2025$8,950,000PendingOneKey® MLS as distributed by MLS GRID #H6318222
05/12/2025$8,950,000ContingentHVCRMLS #153621
05/12/2025$8,950,000PendingToActiveHVCRMLS #153621
05/12/2025$8,950,000ContingentHVCRMLS #153621
09/30/2024$8,950,000PriceChange
Columbia Greene Northern Dutchess MLS #153621
07/17/2024$9,800,000Listed For SaleColumbia Greene Northern Dutchess MLS #153621
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Comparable Sales for 25 Winchell Trail

Address
Distance
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Sold Price
Sold Date
Bed
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17 Forest Lane, Millerton, NY
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53 Brooks Rd, Pine Plains, NY
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525 Winchell Mountain Road, Millerton, NY
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$365,000
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3807 Route 199, Pine Plains, NY
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Assigned Schools

These are the assigned schools for 25 Winchell Trail.
View nearby schools on GreatSchools
The GreatSchools Rating compares schools on a variety of school quality indicators including test scores, college readiness, equity and more. Learn more.

What Locals Say about Pine Plains

At least 17 Trulia users voted on each feature.

  • 95 % Say parking is easy

  • 95 % Say yards are well-kept

  • 94 % Say it's dog friendly

  • 89 % Say there's wildlife

  • 86 % Say there's holiday spirit

  • 85 % Say people would walk alone at night

  • 81 % Say kids play outside

  • 78 % Say car is needed

  • 76 % Say it's walkable to restaurants

  • 72 % Say it's quiet

  • 70 % Say there are sidewalks

  • 68 % Say it's walkable to grocery stores

  • 65 % Say they plan to stay for at least 5 years

  • 64 % Say there are community events

  • 63 % Say neighbors are friendly

  • 61 % Say streets are well-lit

Sourced by Trulia users. Learn more about our methodology.
  • hill_js
    "Neighbors are friendly and for the most part don’t mind if a dog barks. Neighborhoods are walkable and safe too. "
    1
    Flag
  • Martin H.
    "People walk their dogs up and down this street while there are no sidewalks cars are respectful of pedestrians"
    1
    Flag
  • Kate O.
    "I have lived in Pine Plains for most of my life. It is a friendly community. It is a truly beautiful place to live with amazing hiking trails in and around the area."
    2
    Flag
  • Kate O.
    "small town, great school, I have lived here my entire life. nice mix of second home owners and locals. great place for outdoor activities and good food "
    1
    Flag
  • gailtkelly
    "It is close enough to town to walk. The HS is a few blocks away. The fire house is 2 blocks away . Entertainment is in town."
    1
    Flag
  • Ccrizal
    "Have lived in a few places, really like it here, assuming you are an involved parent - good school system, love the views & hiking opportunities - in 20 years have never locked my door & have never had a problem...."
    3
    Flag

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IDX information © 2026 by the Hudson Valley Catskill Region MLS. All Rights Reserved. The data relating to real estate on this website comes in part from the IDX of the Hudson Valley Catskill Region MLS.
Information is deemed reliable but is not guaranteed accurate by the MLS. IDX information is provided exclusively for consumers' personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing.

Homes for rent near 25 Winchell Trail

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25 Winchell Trail, Pine Plains, NY 12567 is a 5 bedroom, 5 bathroom, 5,935 sqft single-family home built in 2023. This property is not currently available for sale. 25 Winchell Trail was last sold on Jul 3, 2025 for $8,350,000 (7% lower than the asking price of $8,950,000).