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.
For sale
$5,000,000
399 Gregory Road, Monticello, NY 12701
14beds
17,570sqft
Single Family Residence, Residential
Built in 1989
20 Acres Lot
$-- Zestimate®
$285/sqft
$-- HOA
What's special
Indoor swimming poolExpansive decks and patiosPremium outdoor furniture
- 45 days
- on Zillow |
- 871 |
- 34 |
Zillow last checked: 7 hours ago
Listing updated: May 14, 2025 at 02:07am
Listing by:
Master Realty Group Inc. 845-208-2115,
Rivky Klagsbrun 845-662-5046
Source: OneKey® MLS,MLS#: 858111

Travel times
Tour with a buyer’s agent
Tour with a buyer’s agent
Facts & features
Interior
Bedrooms & bathrooms
- Bedrooms: 14
- Bathrooms: 17
- Full bathrooms: 12
- 1/2 bathrooms: 5
Heating
- Forced Air
Cooling
- Central Air
Appliances
- Included: Dishwasher, Dryer, Freezer, Oven, Refrigerator, Washer
- Laundry: Washer/Dryer Hookup, Multiple Locations
Features
- Chandelier, Entrance Foyer, Granite Counters, High Speed Internet, Primary Bathroom, Open Kitchen, Sound System, Storage
- Flooring: Carpet, Ceramic Tile, Hardwood
- Windows: Skylight(s)
- Basement: Partial
- Attic: None
- Number of fireplaces: 2
Interior area
- Total structure area: 17,570
- Total interior livable area: 17,570 sqft
Property
Parking
- Total spaces: 18
- Parking features: Covered, Driveway
- Has uncovered spaces: Yes
Features
- Patio & porch: Deck, Patio
- Exterior features: Gas Grill, Playground
- Has private pool: Yes
- Pool features: In Ground, Indoor
- Fencing: Partial
- Has view: Yes
- View description: Trees/Woods
Lot
- Size: 20 Acres
- Features: Back Yard
Details
- Parcel number: 468905600001056002
- Special conditions: None
- Other equipment: Dehumidifier
Construction
Type & style
- Home type: SingleFamily
- Architectural style: Estate
- Property subtype: Single Family Residence, Residential
Materials
- Stone
Condition
- Updated/Remodeled
- Year built: 1989
- Major remodel year: 2022
Utilities & green energy
- Sewer: Septic Tank
- Utilities for property: Electricity Connected
Community & HOA
Community
- Security: Smoke Detector(s), Video Cameras
HOA
- Has HOA: No
Location
- Region: Monticello
Financial & listing details
- Price per square foot: $285/sqft
- Tax assessed value: $749,200
- Annual tax amount: $30,436
- Date on market: 5/7/2025
- Listing agreement: Exclusive Right To Sell
- Electric utility on property: Yes
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