95 Judson Road, Montgomery, NY 12549

$2,499,900

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… Read More 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. Read Less

Listing Courtesy of Howard Hanna Rand Realty.

Listing Snapshot

Days Online

Last Updated

Jun 6, 2026

Property Type

Single Family Residence

Beds

Full Baths

Square Ft.

3,448

Year Built

2004

Property Tax

$49,500

MLS Number

1006189

30 Days Snapshot Of 12549

$432k

-10%

(avg) sold price

+66%

homes sold

187

+59%

(avg) days on market

Snapshot

Area Map

Additional Details

Appliances & Equipment

Description: "Dryer", "Oven", "Range", "Refrigerator", "Stainless Steel Appliance(s)", "Washer"

Basement

Description: "See Remarks", "Storage Space", "Unfinished", "Walk-Out Access"

Building

Area: 3448, Architecture: "Estate", "Log", "Mini Estate", Construction Materials: "Log", Levels: "Two", Year Built: 2004

Cooling

Details: "Central Air"

Exterior Features

Features: "Dock", "Fire Pit", "Garden", "Gas Grill", "Lighting", "Speakers", Patio Features: "Covered", "Deck", "Patio", "Porch", "Terrace", "Wrap Around"

Fence

Description: "Full"

Fireplaces

Total Fireplaces: 1

Floors

Flooring: "Hardwood", "Tile"

Garage

Garage Spaces: 20

Heating

Heating: "Baseboard", "Forced Air", "Oil", "Radiant", "Radiant Floor"

Laundry

Description: "In Hall", "Inside", "Laundry Room"

Lot

Features: "Garden", "Landscaped", "Private", "Rolling Slope", "Stone/Brick Wall", Acres: 38.3

Property

Description: "Negotiable", "Pool Equip/Cover"

Pool

Features: "Fenced", "In Ground", Private Pool

Utilities

Sewer: "Septic Tank", Water Source: "Well", Utilities: "Cable Connected", "Electricity Connected", "Propane", "Trash Collection Private", "Underground Utilities"

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