399 Gregory RD Monticello, NY 12701
14 Beds
17 Baths
17,570 SqFt
UPDATED:
Key Details
Property Type Single Family Home
Sub Type Single Family Residence
Listing Status Active
Purchase Type For Sale
Square Footage 17,570 sqft
Price per Sqft $284
MLS Listing ID 976893
Style Estate
Bedrooms 14
Full Baths 12
Half Baths 5
HOA Y/N No
Rental Info No
Year Built 1989
Annual Tax Amount $30,436
Lot Size 20.000 Acres
Acres 20.0
Property Sub-Type Single Family Residence
Source onekey2
Property Description
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.
Location
State NY
County Sullivan County
Rooms
Basement Partial
Interior
Interior Features Chandelier, Entrance Foyer, Granite Counters, High Ceilings, High Speed Internet, Primary Bathroom, Open Kitchen, Sound System, Storage
Heating Forced Air
Cooling Central Air
Flooring Carpet, Ceramic Tile, Hardwood
Fireplaces Number 2
Fireplace Yes
Appliance Dishwasher, Dryer, Freezer, Gas Oven, Oven, Refrigerator, Washer
Laundry Multiple Locations
Exterior
Exterior Feature Fire Pit, Gas Grill, Lighting, Mailbox, Playground
Parking Features Covered, Driveway, Parking Lot
Fence Partial
Pool In Ground, Indoor
Utilities Available Electricity Connected
View Trees/Woods
Total Parking Spaces 18
Garage false
Private Pool Yes
Building
Lot Description Back Yard, Front Yard, Landscaped, Part Wooded, Private, Views, Wooded
Sewer Septic Tank
Water Well
Structure Type Stone
Schools
Elementary Schools George L Cooke School
Middle Schools Robert J Kaiser Middle School
High Schools Monticello
School District Monticello
Others
Senior Community No
Special Listing Condition None
Nearby Locations