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You are here: Home / 95 Judson Road, Montgomery, NY 12549 (MLS # 1006189)

95 Judson Road, Montgomery, NY 12549 (MLS # 1006189)

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Price $2,499,900
Status Active
Beds 3
Baths 3 Baths
Home size 3,448 sqft
Lot Size 38.30 ac
Days on Market 2
Welcome to one of the Hudson Valley's most iconic private estates; an extraordinary 38+ acre retreat offering luxury, recreation, equestrian amenities, abundant space for custom vehicle enthusiasts and unmatched entertaining spaces. Known locally as the famed "Orange County Choppers House," this remarkable property blends rustic elegance with modern comfort in a setting designed for those who appreciate both refined living and outdoor adventure. Beyond the gated entrance, a winding driveway passes fenced paddocks, open meadows, and animal outbuildings before arriving at the impressive log home, complete with a wraparound covered porch, metal roof, and expansive courtyard driveway with ample space for oversized vehicles and equipment. Inside, the home showcases rich wood craftsmanship, soaring ceilings, and breathtaking views of the surrounding mountains, koi ponds, and manicured gardens. The chef's kitchen features custom wood cabinetry, granite countertops, a center island, and spacious dining area, while a practical mudroom includes a convenient dog washing station. The dramatic great room serves as the heart of the home with floor-to-ceiling windows and a striking stone fireplace. The main level offers a private office, full bathroom, and a luxurious primary suite complete with a walk-in closet and spa-inspired ensuite featuring a floating jetted soaking tub, oversized tiled shower, and double vanity. Nearly every room opens directly to inviting outdoor living spaces that seamlessly connect the home to its natural surroundings. Upstairs, two generously sized bedrooms share a full bath, while a peaceful loft-style sitting area overlooks both the great room below and the picturesque grounds beyond. The partially finished lower level provides endless potential with a full bathroom and bar area already in place, awaiting your personal finishing touches. Step outside and discover a true resort-style oasis. The spectacular multi-level heated pool features a slide, wading area, and extensive lounging spaces. The pool house includes a tiki bar, full bathroom, and outdoor shower, while dual Thor grills, granite serving stations, and a shaded pergola create the ultimate setting for unforgettable gatherings. The estate continues to impress with a heated two-story showroom garage offering over 7,000 square feet of space. The upper level includes two guest apartments, each with kitchenettes, bedrooms, and bathrooms, creating exceptional opportunities for extended family, guests, or staff accommodations. Equestrian enthusiasts will appreciate the substantial two-story barn currently configured for five horses with room for expansion, along with a massive hay loft, multiple fenced paddocks, and supporting outbuildings. A separate mechanic's garage and workshop sits farther down the drive, providing privacy and flexibility for hobbyists, collectors, or business pursuits. Completing this extraordinary offering is a stunning 1+ acre pond featuring docks, a waterfall, and waterside grilling patio"”an idyllic backdrop for fishing, entertaining, or simply enjoying the peace and beauty of the Hudson Valley countryside. Rarely does a property offer this level of privacy, recreation, functionality, and luxury. Whether envisioned as a family compound, equestrian estate, entertainer's paradise, or Hudson Valley retreat, this iconic property delivers a lifestyle unlike any other.
Property Type(s): Single Family
Last Updated 6/6/2026 Year Built 2004
Garage Spaces 20.0 County Orange

SCHOOLS

Elementary School E J Russell Elementary School
Jr. High School Crispell Middle School
High School Pine Bush Senior High School

Additional Details

AIR Central Air
AIR CONDITIONING Yes
APPLIANCES Dryer, Oven, Range, Refrigerator, Stainless Steel Appliance(s), Washer
BASEMENT Storage Space, Unfinished, Walk-Out Access, Yes
CONSTRUCTION Log
EXTERIOR Dock, Fire Pit, Garden, Gas Grill, Lighting
FIREPLACE Yes
GARAGE Yes
HEAT Baseboard, Forced Air, Oil, Radiant, Radiant Floor
INTERIOR Beamed Ceilings, Breakfast Bar, Built-in Features, Cathedral Ceiling(s), Ceiling Fan(s), Double Vanity, Eat-in Kitchen, Granite Counters, High Ceilings, In-Law Floorplan, Kitchen Island, Master Downstairs, Natural Woodwork, Open Floorplan, Soaking Tub, Storage, Walk-In Closet(s), Wet Bar, Wired for Sound
LOT 38.3 acre(s)
LOT DESCRIPTION Garden, Landscaped, Private, Rolling Slope, Sloped
PARKING Driveway, Garage, Garage Door Opener, Heated Garage, Oversized, Storage
POOL Yes
POOL DESCRIPTION Fenced, In Ground, Private
SEWER Septic Tank
STORIES 2
STYLE Estate, Log, Mini Estate
TAXES 49500
UTILITIES Cable Connected, Electricity Connected, Propane, Underground Utilities
VIEW Yes
VIEW DESCRIPTION Panoramic, Trees/Woods, Water
WATER Private, Well
WATERFRONT DESCRIPTION Pond, Waterfront Access

Location

 

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Listed with Howard Hanna Rand Realty
HGMLS logo Copyright 2026 Hudson Gateway Multiple Listing Service, Inc. All rights reserved.
The data relating to real estate for sale or lease on this web site comes in part from HGMLS. Real estate listings held by brokerage firms other than Suburban Realty are marked with the HGMLS logo or an abbreviated logo and detailed information about them includes the name of the listing broker. Information deemed reliable but not guaranteed.
Date Last Updated: 6/7/26 9:26 PM PDT

This IDX solution is (c) Diverse Solutions 2026.

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About Janet

I have been a Realtor since 1982, and loving it. Serving Rockland County, New York, as well as Bergen County, New Jersey. I am with you every step of the way.

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Janet Eisenberg

Licensed Real Estate Broker in
New York, & New Jersey

31 Drexel Court
New City, NY 10956

info@suburban-realty.com
Phone: (845) 425-3379
Cell: (914) 714-2004

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Janet Eisenberg – Broker at Suburban Realty Inc.

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Whether you are listing your property or looking for your new home, we make the process easy. 30+ years of experience and many happy clients make us a trusted partner in a life-changing event. We are looking forward to your call.