399 Gregory Rd
Description
Set on 20 breathtaking acres in Monticello, this extraordinary nearly 18,000 sq ft 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 Resorts World Catskills, Bethel Woods Center for the...399 Gregory Rd, Monticello, NY – A Private Estate Like No Other
Set on 20 breathtaking acres in Monticello, this extraordinary nearly 18,000 sq ft 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 Resorts World Catskills, Bethel Woods Center for the Arts, Monticello Motor Club, 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 new heating and cooling systems, upgraded electric, low-voltage wiring, security cameras, a brand-new high-capacity septic system, The estate also offers a fully equipped kitchen, A fully equipped game room an additional exterior garage structure, and a private suite upstairs. 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 • Catskills Home ServicesP: (845)-397-7768 C: (845)-662-5046 theklagsbrunpromise@gmail.com
- Listed by Alan R. Wieder • Catskills Home ServicesP: (845)-397-7768 C: (845)-397-7768 Alan@catskillshomeservices.com
Property Details for 399 Gregory Road
Property Details for 399 Gregory Road
| Status | Active |
|---|---|
| MLS # | 976893 |
| Days on Market | 1 |
| Taxes | $30,437 / year |
| HOA Fees | - |
| Condo/Co-op Fees | - |
| Property Type | Single Family |
| MLS Type | Single Family |
| Year Built | 1989 |
| Lot Size | 20.00 AC / 871,200 SF |
| County | Sullivan County |
Location
Building Information for 399 Gregory Road
Payment Calculator
$27,714 per month
30 year fixed, 6.46% Interest
$25,178
$2,536
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1Property Information for 399 Gregory Road
- Senior Community YN: No
- Tax Block: 56
- Tax Lot: 1
- Year Built Effective: 2022
- Property Attached: No
- Structure Type: Detached
- Property Condition: Updated/Remodeled
- State Or Province: NY
- Water Access YN: No
- 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
- Lease Considered: No
- Building Units Total: 1
- Parcel Number: 4689-056-0-0001-056-002
- Tax Assessed Value: $749,200.00
- Tax Source: Municipality
- Tax Year: 2024.0
- Association: No
- 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, Trees/Woods, Video Cameras, Well
- Interior Features: Chandelier, Entrance Foyer, Granite Counters, High Ceilings, High Speed Internet, Primary Bathroom, Open Kitchen, Sound System, Storage
- Appliances: Dishwasher, Dryer, Freezer, Gas Oven, Oven, Refrigerator, Washer
- Total Rooms: 9
- Basement: Partial
- Attic Description: None
- Fireplace: Yes
- Fireplaces Total: 2
- 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
- Window Features: Skylight(s)
- Flooring: Carpet, Ceramic Tile, Hardwood
- Living Area: 17,570.00
- 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, 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 Responsibility: Public Maintained Road
- Other Structures: Shed(s)
- 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, Parking Lot
- Parking Total: 18.00
- Garage: No
- 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, Freezer, Gas Oven, Oven, Refrigerator, Washer, Forced Air, Fire Pit, Gas Grill, Lighting, Mailbox, Playground, In Ground, Indoor
- Down Payment Resource: No
Property History for 399 Gregory Road
| Date | Event & Source | Price | Appreciation |
|---|---|---|---|
| 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 |
|---|---|---|
| 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, Compass often displays two records for one sale: the MLS record and the public record.
Public Records for 399 Gregory Road
Schools 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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Listing Courtesy of Catskills Home Services
Based on information submitted to the MLS GRID as of 04/20/2026 05:03 AM. 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.
