399 Gregory Rd Monticello, NY 12701
Property details
About 399 Gregory Rd
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.
Highlights
Summary
- Partial Bathrooms: 5
- Full Bathrooms: 12
- Appliances: Dishwasher, Dryer, Freezer, Oven, Refrigerator, Washer
- Basement: Yes
- Flooring Type: Carpet, Ceramic Tile, Hardwood
- Interior: Chandelier, Entrance Foyer, Granite Counters, High Speed Internet, Primary Bathroom, Open Kitchen, Sound System, Storage, Washer/Dryer Hookup
- Total Bedroom Count: 14
- Private Pool: Yes
- Parking: Covered, Driveway
- View: Trees/Woods
- Exterior: Gas Grill, Playground, Fence, Deck, Patio
- Architectural Style: Estate
- Heating: Forced Air
- Cooling: Central Air
- List Price: $5,000,000
- Price/SqFt: $284
- Annual Tax Amount: $44,795
- Tax Year: 2021
- Lot: Back Yard
- Year Built: 1989
- Living Area: 17,570 SqFt
- Lot Size: 20 Acres
- MLS Number: 858111
- MLS Name: ONEKEY2
- Office Name: Master Realty Group Inc.
- Office Phone: (845) 208-2115
Listings courtesy of OneKey MLS as distributed by MLS GRID.
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Last updated on: 7/24/2025, 12:41:29 PM Eastern. If you have any questions regarding the accuracy of this data, please contact us at help@rockethomes.com.
Price information
Property sales
| Date | Event | Price |
|---|---|---|
| May 16, 2022 | Home Sold | $1,378,500 |
Tax history
| Year | Assessment | Property Tax |
|---|---|---|
| 2023 | $749,200 | $- |
| 2022 | $747,200 | $- |
| 2021 | $747,200 | $44,795 |
| 2020 | $747,200 | $44,795 |
| 2019 | $747,200 | $46,082 |
| 2018 | $747,200 | $44,683 |
| 2017 | $747,200 | $44,506 |
History based on county public records data.
Nearby schools
3
Kenneth L Rutherford School
Public District 3-5
4.8 mi
•26 Patricia Pl
5
George Ross Mackenzie Elementary School
Public District PK-6
8.9 mi
•1045 Proctor Rd
3
Benjamin Cosor Elementary School
Public District PK-6
12.3 mi
•15 Old Falls Rd
School ratings are a score out of 10, where 10 is the highest and 1 is the lowest.
Neighborhood
The neighbors living near this home have an average income of $40,217. The most common annual income of people living in Monticello, NY is less than $<35k. The most common type of family is single, no kids. Residents of this area typically have post secondary degree education.
How much money do the neighbors make?
What level of education do the neighbors have?
What types of families live nearby?
Are the neighbors home owners or renters?
How old are people in this area?
What do the neighbors do for fun?
Hunting
NASCAR
Monster Trucks
Where do the neighbors shop?
Dick's Sporting Goods
Dillards
Wal-Mart
Where do the neighbors go to eat?
Texas Roadhouse
Cracker Barrel
Hardee's
What do the neighbors drive?
Subaru
Cadillac
Ram
What do the neighbors listen to?
New Country
News/Talk/Information
Classic Country
Frequently asked questions
About 399 Gregory Rd
The listing price of 399 Gregory Rd property is $5,000,000.
The property 399 Gregory Rd is a house located in Monticello, New York, 12701.
Active Listing: 399 Gregory Rd is For Sale (Active/New) which means the seller is accepting offers.
The nearby schools for 399 Gregory Rd are: Kenneth L Rutherford School (GreatSchools Rating 3/10), George Ross Mackenzie Elementary School (GreatSchools Rating 5/10), Benjamin Cosor Elementary School (GreatSchools Rating 3/10), Robert J Kaiser Middle School (GreatSchools Rating 2/10), Liberty Middle School (GreatSchools Rating 2/10), Damascus Area School (GreatSchools Rating 6/10), Monticello High School (GreatSchools Rating 3/10), Eldred Junior-Senior High School (GreatSchools Rating 4/10), Fallsburg Junior Senior High School (GreatSchools Rating 2/10).
According to the records, the last property tax for 2021 is $44,795 (source: MLS/based on county public records data).
The last sale was on May 16, 2022 for $1,378,500 (source: MLS/tax record).
The property at 399 Gregory Rd has 14 bedrooms and 12 full and 5 half bathrooms.
The property 399 Gregory Rd is 17,570 SqFt (source: MLS/tax record).
The year of construction for 399 Gregory Rd is 1989.
This home is located at 399 Gregory Rd in Monticello, NY and zip code 12701. This 17,570 square foot home, which was built in 1989, sits on a 20.00 acre lot. Features: 14 bedrooms, 17 bathrooms. It has been listed on Rocket Homes since May 7, 2025 and is currently priced at $5,000,000.
In June 2025, from all listings sold in Monticello, NY there were more than 3 sold above asking price, over 6 sold below and more than 2 were sold right at the asked price. Between May and June 2025, Monticello, NY real estate market has seen increase in the number of listings by 17.1%. In June 2025 median list price was $315,000 and the average listing age was 47 days.