399 Gregory RD, Monticello, NY 12701
399 Gregory RD, Monticello, NY 12701
399 Gregory RD, Monticello, NY 12701
399 Gregory RD, Monticello, NY 12701
399 Gregory RD, Monticello, NY 12701
399 Gregory RD, Monticello, NY 12701
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$ 5,000,000
Est. payment | /mo

14 Beds

17 Baths

17,570 SqFt


Save
$ 5,000,000
Est. payment | /mo
Save

14 Beds

17 Baths

17,570 SqFt

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 $31,248

Lot Size 20.000 Acres

Acres 20.0

Property Sub-Type Single Family Residence

Source onekey2

Property Description

399 Gregory Rd, Monticello, NY – A Private Estate Like No Other

Set on 20 breathtaking acres in Monticello, this extraordinary nearly 18,000sf 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 Monticello Motor Club, Resorts World Catskills, Kartrite Indoor Water Park, Monster Golf Course, Bethel Woods Center for the Arts, 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 a brand new dehumidifier and heater for the indoor pool, new heating and cooling systems, upgraded electric, low-voltage wiring, security cameras, and a brand-new high-capacity septic system. The estate also offers a fully equipped kitchen, a fully equipped game room, a detached garage, and a separate, private suite on the upper level. 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, Storage Space, Unfinished

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, Vinyl

Fireplaces Number 2

Fireplaces Type Wood Burning

Fireplace Yes

Appliance Dishwasher, Dryer, Exhaust Fan, Freezer, Gas Oven, Oven, Refrigerator, Washer, Tankless Water Heater

Laundry Multiple Locations

Exterior

Exterior Feature Fire Pit, Gas Grill, Lighting, Mailbox, Playground

Parking Features Covered, Driveway, Garage, Parking Lot

Garage Spaces 2.0

Fence Partial

Pool In Ground, Indoor

Utilities Available Electricity Connected

Waterfront Description Stream

View Trees/Woods

Total Parking Spaces 20

Garage true

Private Pool Yes

Building

Lot Description Back Yard, Front Yard, Landscaped, Part Wooded, Private, Views, Wooded

Foundation Concrete Perimeter

Sewer Septic Tank

Water Well

Level or Stories Two

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

OneKey MLS/ Hudson Gateway (HGAR)/ Long Island MLS (MLSLI)/ Mid Hudson MLS
Listed by Catskills Home Services • Rivky Klagsbrun
Nearby Locations
Michael & Tara Holmes

"My job is to find and attract mastery-based agents to the office, protect the culture, and make sure everyone is happy! "

+1(914) 774-5684

mikeholmesrealestate@gmail.com

777 Westchester Ave, White Plains, NY, 10604, USA

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399 Gregory RD