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USANYMonticello399 Gregory Rd
Listing image | Image 1

399 Gregory Rd, Monticello, NY

House

For Sale

Listed price in listed location currency (USD).
$5,000,000

141718

MLS® 976893

Overview

Key Facts

Type Single Family Residence
Levels Residential
Size 17570 sqft
Garage 
Taxes $30,437
Days Active 0
Lot Size 
Approx. Age 1989
Avg. Price Per Sqft $284
MLS® Number 976893

Property Address: 399 Gregory Rd, Monticello, NY, 12701-4735

Average square foot calculated using Size range provided by listing agent.

Description

399 Gregory Rd, Monticello, NY – A Private Estate Like No Other Set on 20 breathtaking acres in Monticello, this extraordinary nearly 18, 000 sq ft gated estate delivers an unmatched combination of scale, luxury, and privacy. Surrounded by a perfect blend of open land and natural beauty—including a picturesque stream and sweeping views—this property offers a rare sense of seclusion just minutes from the area’s top destinations. Ideally located near Resorts World Catskills, Bethel Woods Center for the Arts, Monticello Motor Club, and the scenic Catskill Mountains, this estate combines tranquility with convenience and access to year-round attractions. Inside, the home is designed for both grand entertaining and everyday comfort. Amenities include a spectacular indoor pool, full bar, pizza oven, game room, private theater, gym, multiple fireplaces, sauna, and hot tub—creating a true resort-style experience. With 14+ bedrooms, this property has successfully hosted weddings, retreats, and large gatherings. Nearly every aspect of the home has been thoughtfully upgraded by the current owners. Improvements include new heating and cooling systems, upgraded electric, low-voltage wiring, security cameras, a brand-new high-capacity septic system, The estate also offers a fully equipped kitchen, A fully equipped game room an additional exterior garage structure, and a private suite upstairs. The entire property is fully winterized and move-in ready. Zoned RR2, this estate presents exceptional flexibility and investment potential. With planning board approval, it is well-suited for use as a retreat center, summer camp, or event venue. A discerning buyer can enjoy this home as a private luxury escape while also generating substantial income through rentals, weddings, and organizational use throughout the year. This is truly a property that must be experienced in person to fully appreciate the scale, craftsmanship, and atmosphere it offers—photos simply don’t capture the full picture of what this mansion entails. A rare opportunity for the buyer who values privacy, prestige, and potential—this is more than a home, it’s a legacy estate. Reach out today to schedule your private tour.
MLS® Number976893
Laundry Level
Central VacNo
FireplaceNo
Acreage
Exterior
Garage
Approx. Age1989
BasementPartial
DrivewayCovered, Driveway, Parking Lot
Garage Spaces
Heat
A/C
Heating Fuel

Extras

Price History

-End Date
Not Sold YetSold Price

For Sale

Apr 20, 2026List Date
$5,000,000List Price

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