by RH Advisors

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Sullivan 12701
399 Gregory Road
$5,000,000
● House - For Sale

399 Gregory Road

Thompson, NY 12701
bedrooms
14 Beds
bathrooms
12 Baths, 5 Half Baths
square feet
17,570 Ft²
$27,155
Est. Monthly

About This Property

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.
Unit Size
17,570 Ft²
Days on Market
202 days
Land Size
20.00 acres
Price per sqft
$285
Property Type
House
Property Taxes
$2,604
HOA Dues
-
Year Built
1989

Listed By

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Last updated: 7 months ago (OneKey MLS #KEY976893)

Price History

Date / Event Date Event Price
Apr 8, 2026 Listed by Catskills Home Services $5,000,000
Listed by Catskills Home Services
May 16, 2022 Sold
Sold
Jan 19, 2022 No longer available -
No longer available
Nov 30, 2021 Relisted $1,999,999
Relisted
Nov 29, 2021 No longer available -
No longer available
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Property Highlights

Garage
Parking Available
Air Conditioning
Fireplace
Parking Details
Has Garage
Parking Features: Covered, Driveway, Garage, Parking Lot
Garage Spaces: 2
Interior Details
Half Bathrooms: 5
Full Bathrooms: 12
Interior Features: Chandelier, Entrance Foyer, Granite Counters, High Ceilings, High Speed Internet, Sound System, Storage, Primary Bathroom, Open Kitchen
Appliances: Dishwasher, Dryer, Exhaust Fan, Freezer, Gas Oven, Oven, Refrigerator, Washer, Tankless Water Heater
Flooring Type: Carpet, Ceramic Tile, Hardwood, Vinyl
Laundry Features: Multiple Locations
Rooms: 9
Has Fireplace
Fireplace Features: Wood Burning
Fireplaces: 2
Basement: Partial, Storage Space, Unfinished
Exterior Details
Square Footage: 17570
Square Footage Source: $0
Security Features: Smoke Detector(s), Video Cameras
Property Condition: Updated/Remodeled
Architectural Style: Estate
Year Built: 1989
Waterfront Features: Stream
Levels: Two
Other Structures: Shed(s)
Building Area Units: Square Feet
Window Features: Skylight(s)
Construction Materials: Stone
Patio and Porch Features: Deck, Patio
Pool Features: In Ground, Indoor
Pool is Private
Lot Features: Back Yard, Front Yard, Landscaped, Private, Views, Wooded, Part Wooded
Lot Size Area: 871200
Lot Size Units: Square Feet
Lot Size Acres: 20
Lot Size Square Feet: 871200
Tax Lot: 1
Water Source: Well
Financial Details
Tax Assessed Value: $749,200
Tax Annual Amount: $31,248
Utilities Details
Cooling Type: Central Air
Heating Type: Forced Air
Sewer : Septic Tank

Building Info

Overview

    General

  • Year Built: 1989
  • Effective Year Built: 1989
  • Total Rooms: 8
  • Bedroom Count: 6
  • Bathroom Count: 4
  • Full Bathrooms: 4
  • Partial Bathrooms: 4
  • Building Condition: 6
  • Building Quality: 7
  • Construction Type: 0
  • Building Style: 21
  • Exterior Walls Type: 17
  • Interior Walls Type: 0
  • Roof Shape Type: 0
  • Roof Cover Type: 0
  • Floor Count: 200
  • Floor Cover: 0
  • Basement Type: 6
  • Basement Area: 0
  • Garage Type: 10
  • Garage Square Area: 2,180
  • Parking Space Count: 7
  • Patio Type: 0
  • Porch Type: 7
  • Pool Type: 10

    Dimensions

  • Lot Size Square Feet: 871,200
  • Total Building Area: 16,476
  • Building Area: 16,476
  • Building Area Measurement: L

    Heating and Cooling

  • Air Conditioning: 0
  • Heating: 10
  • Heated Square Feet: 16,476
  • Heating Fuel Type: 6

    Utilities

  • Sewer System: 4
  • Water Service: 5

Building

  • Building Type: 0
  • Property Class: R
  • Land Acres: 0000020000
  • Standard Land Use Code: 1008
  • County Land Use Code: 240

Neighborhood

  • School District Name: Monticello Central School District
  • School Tax School District: MONTICELLO
  • Census Tract: 951600

Zoning

  • Zoning: RR2

Geography

  • District: 484689
  • Section: 56
  • Parcel: 484689 56.-1-56.2
  • Block: 1
  • Lot: 56.002
  • Municipality: THOMPSON (TOV)
  • Latitude: 41.6063
  • Longitude: -74.7744

    Address

  • Full Address: 399 Gregory Rd
  • Address - House Number: 399
  • Address - Street Name: Gregory
  • Address - Suffix Type: Rd
  • State: NY
  • City Name: Monticello
  • Carrier Code: R001
  • 4-Digit Zip Code: 4735
  • Zip Code: 12701

Valuation

    Tax

  • Tax Year: 2022
  • Tax Amount: $0
  • Tax Rate Code Area: 484601

    Appraisal Valuation

  • Standard Deviation: 0.1646
  • Valuation Date: Mar 13, 2024
  • Confidence Score: 67
  • Final Value: 1,637,706
  • High Value: 1,907,379
  • Low Value: 1,368,032

    Market Valuation

  • Market Total Value: $1,498,400
  • Market Land Value: $128,000
  • Market Improvement Value: $1,370,400

    Assessments Valuation

  • Assessed Year: 2023
  • Assessed Total Value: $749,200
  • Assessed Land Value: $64,000
  • Assessed Improvements Value: $685,200

    Sales

  • Current Sale Contract Date: May 04, 2022
  • Current Sale Recording Date: May 16, 2022
  • Current Sale Price:
  • Current Sale Document Type: 27
  • Current Sale Input Document Number: 2022-5236
  • Previous Sale Recording Date: Dec 30, 2002
  • Previous Sale Contract Date: Dec 06, 2002
  • Previous Sale Amount: $345,000
  • Previous Sale Document Type: 27
Data used for valuation calculations is provided by RealtyHop, and other third party sources

Comparables

Unit
Status
Type
Beds
Baths
ft²
Price/ft²
Asking Price
Listed On
Closing Price
Sold On
HOA + Taxes

About Sullivan


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Nearby Rentals

Unit for rent at 11 Richards Avenue, Monticello, NY, 12701

$2,000 /mo

  • 3 Beds
  • 2 Baths
  • 1,428 ft²
11 Richards Avenue, Monticello, NY, 12701 Listing by Shaool Nehari


Frequently Asked Questions

When was property at 399 Gregory Road built and last sold?
The property at 399 Gregory Road was built in 1989 and last sold on May 4, 2022 for $1,378,500.
How much is this home worth?
The estimated value of the home located at 399 Gregory Road is $4,943,602.
What are some comparable homes to 399 Gregory Road?
There are currently no comparable homes to 399 Gregory Road.