Listing photo for 399 Gregory Road, Monticello, NY
Listing photo for 399 Gregory Road, Monticello, NY
Listing photo for 399 Gregory Road, Monticello, NY
Listing photo for 399 Gregory Road, Monticello, NY
Listing photo for 399 Gregory Road, Monticello, NY
Listing photo for 399 Gregory Road, Monticello, NY
Listing photo for 399 Gregory Road, Monticello, NY
Listing photo for 399 Gregory Road, Monticello, NY
Listing photo for 399 Gregory Road, Monticello, NY
Listing photo for 399 Gregory Road, Monticello, NY
Listing photo for 399 Gregory Road, Monticello, NY
Listing photo for 399 Gregory Road, Monticello, NY
Listing photo for 399 Gregory Road, Monticello, NY
Listing photo for 399 Gregory Road, Monticello, NY
Listing photo for 399 Gregory Road, Monticello, NY
Listing photo for 399 Gregory Road, Monticello, NY
Listing photo for 399 Gregory Road, Monticello, NY
Listing photo for 399 Gregory Road, Monticello, NY
Listing photo for 399 Gregory Road, Monticello, NY
Listing photo for 399 Gregory Road, Monticello, NY
Listing photo for 399 Gregory Road, Monticello, NY
Listing photo for 399 Gregory Road, Monticello, NY
Listing photo for 399 Gregory Road, Monticello, NY
Listing photo for 399 Gregory Road, Monticello, NY
Listing photo for 399 Gregory Road, Monticello, NY
Listing photo for 399 Gregory Road, Monticello, NY
Listing photo for 399 Gregory Road, Monticello, NY
Listing photo for 399 Gregory Road, Monticello, NY
Listing photo for 399 Gregory Road, Monticello, NY
Listing photo for 399 Gregory Road, Monticello, NY
Listing photo for 399 Gregory Road, Monticello, NY
Listing photo for 399 Gregory Road, Monticello, NY
Listing photo for 399 Gregory Road, Monticello, NY
Listing photo for 399 Gregory Road, Monticello, NY
Listing photo for 399 Gregory Road, Monticello, NY
Listing photo for 399 Gregory Road, Monticello, NY
Listing photo for 399 Gregory Road, Monticello, NY
Listing photo for 399 Gregory Road, Monticello, NY
Listing photo for 399 Gregory Road, Monticello, NY
Listing photo for 399 Gregory Road, Monticello, NY
Listing photo for 399 Gregory Road, Monticello, NY
Listing photo for 399 Gregory Road, Monticello, NY
Listing photo for 399 Gregory Road, Monticello, NY
Listing photo for 399 Gregory Road, Monticello, NY
Listing photo for 399 Gregory Road, Monticello, NY
Listing photo for 399 Gregory Road, Monticello, NY
Listing photo for 399 Gregory Road, Monticello, NY
Listing photo for 399 Gregory Road, Monticello, NY
Listing photo for 399 Gregory Road, Monticello, NY
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399 Gregory Road,

Monticello, NY

$5,000,000

14 Beds
17 Baths
17,570 Sqft
20.00 Acres

Discover unparalleled luxury in this meticulously renovated almost 18,000 square foot mansion nestled on 20 acres of mostly flat land in rapidly developing Monticello, just moments from the thriving recently approved Satmar year-round community. This extraordinary RR2-zoned property offers tremendous versatility, comfortably accommodating large amount of people and perfectly suited for a yeshiva, organization headquarters, retreat center, or summer camp (with planning board approval). Boasting a spectacular indoor swimming pool, separate suite with private entrance, picturesque stream alongside the property, expansive decks and patios with premium outdoor furniture, ample storage throughout, and a brand new high-capacity septic system, this estate provides both privacy and convenience in a fully winterized, completely renovated, move-in ready package that represents a rare opportunity for discerning buyers seeking both prestige and practicality. INVESTMENT POTENTIAL Development Opportunity: RR2 zoning allows for summer camp use with planning board approval Subdivision Potential: Possibility for additional buildable lot, enhancing investment value Growing Area: Located in Monticello's rapidly developing region, promising future appreciation This rare offering combines luxury living with exceptional versatility and investment potential. The property's pristine condition, strategic location, and extensive amenities create an unmatched opportunity. Contact us today for a private showing of this extraordinary estate.

Facts & Features
MLS® # 858111
Price $5,000,000
Bedrooms 14
Bathrooms 17.00
Full Baths 12
Half Baths 5
Square Footage 17,570
Acres 20.00
Year Built 1989
Type Residential
Sub-Type Single Family Residence
Style Estate
Status Active
MLS hgmls
Community Information
Address 399 Gregory Road
City Monticello
County Sullivan
State NY
Zip Code 12701
Amenities
Utilities Electricity Connected
Parking Spaces 18
Parking Covered, Driveway
View Trees/Woods
Is Waterfront No
Has Pool Yes
Pool In Ground, Indoor
Interior
Interior Carpet, Ceramic Tile, Hardwood
Interior Features Chandelier, Entrance Foyer, Granite Counters, High Speed Internet, Primary Bathroom, Open Kitchen, Sound System, Storage, Washer/Dryer Hookup
Appliances Dishwasher, Dryer, Freezer, Oven, Refrigerator, Washer
Heating Forced Air
Cooling Central Air
Has Basement Yes
Basement Partial
Fireplace Yes
# of Fireplaces 2
Exterior
Exterior Features Gas Grill, Playground
Lot Description Back Yard
Windows Skylight(s)
Construction Stone
School Information
District Monticello
Elementary Contact Agent
Middle Robert J Kaiser Middle School
High Monticello High School
Additional Information
Date Listed May 6th, 2025
Days on Market 46
Short Sale No
RE / Bank Owned No
Listing Details
Listing Courtesy of Master Realty Group Inc.
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Listing information last updated on June 23rd, 2025 at 11:20am EDT.