399 Gregory Road
Description
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...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.
- Listed by: Rivky Klagsbrun 845.397.7768 theklagsbrunpromise@gmail.com • Catskills Home Services
- Listed by: Alan R. Wieder 845.397.7768 Alan@catskillshomeservices.com • Catskills Home Services
Location
$29,297 per month
30 year fixed, 7.03% Interest
$26,693
$2,604
$0
1Property Information for 399 Gregory Road
Property Details
- Taxes: $31,248 / year
- MLS Type: Single Family
- County: Sullivan County
- City/Township: Thompson
- View: Trees/Woods
- Architectural Style: Estate
- Garage Spaces: 2
- Waterfront: Yes
- Section Area: Sackett Lake Road- Starlight Road
Building Information
- Year Built: 1989
- Lot Size: 20.00 AC / 871,200 SF
Summary
- Hamlet: Swinging Bridge
- Senior Community YN: No
- Directions: GPS to 399 Gregory Road, Monticello, NY 12701.
- Tax Block: 56
- Tax Lot: 1
- Year Built Effective: 2022
- Property Attached: No
- Structure Type: Detached
- Levels: Two
- Property Condition: Updated/Remodeled
- Country: US
- State Or Province: NY
- Water Access YN: Yes
- School District: Monticello
- Elementary School District: Monticello
- Elementary School: George L Cooke School
- Middle Or Junior School District: Monticello
- Middle Or Junior School: Robert J Kaiser Middle School
- High School District: Monticello
- High School: Monticello High School
Rental
- Lease Considered: No
Unit Information
- Building Units Total: 1
Taxes and HOA Information
- Parcel Number: 4689-056-0-0001-056-002
- Tax Assessed Value: $749,200.00
- Additional Fees: No
- Tax Source: Municipality
- Tax Year: 2026
- Association: No
Interior and Exterior Features
- Amenities: Carpet, Ceramic Tile, Chandelier, Deck, Entrance Foyer, Estate, Fire Pit, Gas Grill, Granite Counters, Hardwood Floors As Seen, High Ceilings, High Speed Internet, In Ground, Indoor, Lighting, Mailbox, Multiple Locations, Open Kitchen, Partial, Patio, Playground, Primary Bathroom, Shed(s), Sky Light, Smoke Detector(s), Sound System, Storage, Stream, Trees/Woods, Video Cameras, Vinyl, Well, Wood Burning
- Interior Features: Chandelier, Entrance Foyer, Granite Counters, High Ceilings, High Speed Internet, Primary Bathroom, Open Kitchen, Sound System, Storage
- Appliances: Dishwasher, Dryer, Exhaust Fan, Freezer, Gas Oven, Oven, Refrigerator, Washer, Tankless Water Heater
- Number Of Kitchens: 2
- Total Rooms: 9
- Basement: Partial, Storage Space, Unfinished
- Attic Description: Scuttle
- Fireplace: Yes
- Fireplaces Total: 2
- Fireplace Features: Wood Burning
- Location Amenities: Hardwood Floors As Seen, Entry Foyer, Foyer, Granit Countertops, High Ceilings, High Speed Internet, Open Kitchen, Storage, Privacy, Scenic View, Deck, Patio, In Ground Pool, Pool Indoor, Sky Light
- Laundry Features: Multiple Locations
- Security Features: Smoke Detector(s), Video Cameras
- Spa: No
- Window Features: Skylight(s)
- Flooring: Carpet, Ceramic Tile, Hardwood, Vinyl
- Living Area: 17570
- Foundation Details: Concrete Perimeter
- Basement: Yes
- Exterior Features: Fire Pit, Gas Grill, Lighting, Mailbox, Playground
- Exterior Property Features: Fire Pit, Gas Grill, Lighting, Mailbox, Playground, In Ground, Indoor, Deck, Patio, Covered, Driveway, Garage, Parking Lot, Partial, Skylight(s), Back Yard, Front Yard, Landscaped, Part Wooded, Private, Views, Wooded
- Elevation Certificate: No
- Fencing: Partial
- Patio And Porch Features: Deck, Patio
- Construction Materials: Stone
- Road Frontage Type: Municipal
- Road Responsibility: Public Maintained Road
- Other Structures: Shed(s)
- Waterfront Features: Stream
- Horse: Yes
- Pool Private: Yes
- Pool Features: In Ground, Indoor
- Pool Details: In Ground,Indoor
- Lot Features: Back Yard, Front Yard, Landscaped, Part Wooded, Private, Views, Wooded
- Additional Parcel: No
- Site Features: Back Yard, Front Yard, Landscaped, Part Wooded, Private, Views, Wooded
- Building Area Units: Square Feet
- Parking Features: Covered, Driveway, Garage, Parking Lot
- Parking Total: 20.00
- Garage: Yes
- Carport: No
- Cooling: Central Air
- Heating: Forced Air
- Heat Fuel Type: Forced Air
- Sewer: Septic Tank
- Water Source: Well
- Utilities: Electricity Connected
- Green Features: Skylight(s), Dishwasher, Dryer, Exhaust Fan, Freezer, Gas Oven, Oven, Refrigerator, Washer, Tankless Water Heater, Forced Air, Fire Pit, Gas Grill, Lighting, Mailbox, Playground, In Ground, Indoor
Agent
- Down Payment Resource: No
Property History for 399 Gregory Road
| Date | Event & Source | Price | Appreciation |
|---|---|---|---|
| May 7, 2026 | Expired ONEKEY #858111 | $5,000,000 | — |
| Apr 19, 2026 | Listed (Active) ONEKEY #976893 | $5,000,000 | — |
| Oct 30, 2025 | Temporarily Off Market ONEKEY #858111 | $5,000,000 | — |
| May 7, 2025 | Listed (Active) ONEKEY #858111 | $5,000,000 | — |
| May 4, 2022 | Sold (Public Record) Public Record #1490743573 | $1,378,500 | — |
| Oct 31, 2021 | Expired ONEKEY #H6124665 | $2,499,000 | — |
| Jun 22, 2021 | Listed (Active) ONEKEY #H6124665 | $2,499,000 | — |
| Sep 10, 2018 | Expired ONEKEY #H4812591 | $1,999,999 | — |
| Mar 28, 2018 | Listed (Active) ONEKEY #H4812591 | $2,300,000 | — |
| Aug 17, 2017 | Expired ONEKEY #H4637240 | $1,999,999 | — |
| Nov 10, 2016 | Expired ONEKEY #H4551034 | $3,999,999 | — |
| Aug 17, 2016 | Listed (Active) ONEKEY #H4637240 | $1,999,999 | — |
| Nov 19, 2015 | Listed (Active) HGMLS #4551034 | $3,999,999 | — |
| Nov 19, 2015 | Listed (Active) ONEKEY #H4551034 | $3,999,999 | — |
| Oct 15, 2015 | Expired HVCR MLS #20145293 | $1,290,000 | — |
| Oct 15, 2015 | Expired ONEKEY #H4440532 | $1,290,000 | — |
| Nov 2, 2014 | Listed (Active) ONEKEY #H4440532 | $1,311,111 | — |
| Nov 2, 2014 | Listed (Active) HGMLS #4440532 | $1,311,111 | — |
| Oct 15, 2014 | Listed (Active) HVCR MLS #20145293 | $1,311,111 | — |
| Date | Event & Source | Price |
|---|---|---|
| 05/07/2026 | Expired ONEKEY #858111 | $5,000,000 |
| 04/19/2026 | Listed (Active) ONEKEY #976893 | $5,000,000 |
| 10/30/2025 | Temporarily Off Market ONEKEY #858111 | $5,000,000 |
| 05/07/2025 | Listed (Active) ONEKEY #858111 | $5,000,000 |
| 05/04/2022 | Sold (Public Record) Public Record #1490743573 | $1,378,500 |
| 10/31/2021 | Expired ONEKEY #H6124665 | $2,499,000 |
| 06/22/2021 | Listed (Active) ONEKEY #H6124665 | $2,499,000 |
| 09/10/2018 | Expired ONEKEY #H4812591 | $1,999,999 |
| 03/28/2018 | Listed (Active) ONEKEY #H4812591 | $2,300,000 |
| 08/17/2017 | Expired ONEKEY #H4637240 | $1,999,999 |
| 11/10/2016 | Expired ONEKEY #H4551034 | $3,999,999 |
| 08/17/2016 | Listed (Active) ONEKEY #H4637240 | $1,999,999 |
| 11/19/2015 | Listed (Active) HGMLS #4551034 | $3,999,999 |
| 11/19/2015 | Listed (Active) ONEKEY #H4551034 | $3,999,999 |
| 10/15/2015 | Expired HVCR MLS #20145293 | $1,290,000 |
| 10/15/2015 | Expired ONEKEY #H4440532 | $1,290,000 |
| 11/02/2014 | Listed (Active) ONEKEY #H4440532 | $1,311,111 |
| 11/02/2014 | Listed (Active) HGMLS #4440532 | $1,311,111 |
| 10/15/2014 | Listed (Active) HVCR MLS #20145293 | $1,311,111 |
For completeness, we often displays two records for one sale: the MLS record and the public record.
Public Records for 399 Gregory Road
Taxable Value
Land
$64,000Additions
$685,200Tax Record
2024
$47,175 ($3,931 / month)Home Facts
Beds
14Baths
4Total Finished SqFt
16,476 SqFtAbove Grade Finished SqFt
16,476 SqFtStories
2Lot Size
871,200 SqFtStyle
Miscellaneous ResidentialYear Built
1989Zoning
RR2County
SULLIVANAPN
484689 56.-1-56.2Schools near 399 Gregory Road
Rating | School | Type | Grades | Distance |
|---|---|---|---|---|
| Public - | 3 to 5 | |||
| Public - | 6 to 8 | |||
| Public - | 9 to 12 | |||
| Public - | PK to 2 |
Rating | School | Distance |
|---|---|---|
Kenneth L Rutherford School Public3 to 5 | ||
Robert J Kaiser Middle School Public6 to 8 | ||
Monticello High School Public9 to 12 | ||
George L Cooke School PublicPK to 2 |
School ratings and boundaries are provided by GreatSchools.org and Pitney Bowes. This information should only be used as a reference. Proximity or boundaries shown here are not a guarantee of enrollment. Please reach out to schools directly to verify all information and enrollment eligibility.
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No guarantee, warranty or representation of any kind is made regarding the completeness or accuracy of any information, descriptions or measurements (including square footage measurements and property condition), such should be independently verified through appropriate means, including, but not limited to, in person inspection and public records, and Compass International Holdings, its subsidiaries, affiliates and independently owned and operated franchisees, and their affiliated agents and associated third parties expressly disclaim any liability in connection therewith. Photos may be virtually staged or digitally enhanced and may not reflect actual property conditions. Offers of compensation are subject to change at the seller's discretion. No financial or legal advice provided. Equal Housing Opportunity. Subject to change at any time. Compass, Inc., its subsidiaries, affiliates and their agents and associated third parties make no guarantee, warranty or representation regarding the accuracy of any waterfront feature, water view or waterfront view.
Listing Courtesy of Catskills Home Services
Based on information submitted to the MLS GRID as of 04/20/2026 11:10 PM. All data is obtained from various sources and may not have been verified by broker or MLS GRID. Supplied Open House Information is subject to change without notice. All information should be independently reviewed and verified for accuracy. Properties may or may not be listed by the office/agent presenting the information. Properties displayed may be listed or sold by various participants in the MLS. IDX information is provided exclusively for consumers’ personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. The data is deemed reliable but is not guaranteed by MLS GRID. Use of the MLS GRID data may be subject to an end user license agreement prescribed by the applicable MLS of the Member Participant, if any, and as amended from time to time.
