399 Gregory Rd

Monticello, NY 12701

$5,000,000
Price
14
Beds
17,570 Sq. Ft.
$285 / Sq. Ft.
17,570
Sq. Ft.
$285
per Sq. Ft.
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a aerial view of a house with swimming pool and green space
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a view of a patio with table and chairs with wooden floor and plants
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a large kitchen with stainless steel appliances kitchen island granite countertop a sink and cabinets
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Description

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...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.
  1. Listed by Rivky Klagsbrun • Catskills Home Services
    P: (845)-397-7768 C: (845)-662-5046 theklagsbrunpromise@gmail.com
  2. Listed by Alan R. Wieder • Catskills Home Services
    P: (845)-397-7768 C: (845)-397-7768 Alan@catskillshomeservices.com

Property Details for 399 Gregory Road

City/Township
Thompson
View
Trees/Woods
Architectural Style
Estate
Garage Spaces
2.00
Waterfront
Yes
Section Area
Sackett Lake Road- Starlight Road
LISTING UPDATED: 04/20/2026 11:10 PM

Property Details for 399 Gregory Road

StatusActive
MLS #976893
Days on Market45
Taxes$31,248 / year
HOA Fees-
Condo/Co-op Fees-
Property TypeSingle Family
MLS TypeSingle Family
Year Built1989
Lot Size20.00 AC / 871,200 SF
CountySullivan County
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Location

Listing Courtesy of Catskills Home Services
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Building Information for 399 Gregory Road

Stories-Year Built1989Building Size-Lot Size20.00 AC / 871,200 SF

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$27,520 per month

30 year fixed, 6.36% Interest

Principal and Interest

$24,916

Property Taxes

$2,604

HOA Dues

$0

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Property Information for 399 Gregory Road

Summary
Location and General Information
  • 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 Information
  • 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
Rental
  • Lease Considered: No
Unit Information
Unit Information
  • Building Units Total: 1
Taxes and HOA Information
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: 2026.0
  • Association: No
Interior and Exterior Features
Interior 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: 2.0
  • 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: 17,570.00
  • Foundation Details: Concrete Perimeter
  • Basement: Yes
Exterior Features
  • 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 Information
  • 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
  • Parking Features: Covered, Driveway, Garage, Parking Lot
  • Parking Total: 20.00
  • Garage: Yes
  • Carport: No
Utilities
  • Cooling: Central Air
  • Heating: Forced Air
  • Heat Fuel Type: Forced Air
  • Sewer: Septic Tank
  • Water Source: Well
  • Utilities: Electricity Connected
Green Features
  • 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
Payment and Rate
  • Down Payment Resource: No

Property History for 399 Gregory Road

DateEvent & SourcePriceAppreciation
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—
DateEvent & SourcePrice
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

For completeness, we often displays two records for one sale: the MLS record and the public record.

Public Records for 399 Gregory Road

Taxable ValueLand$64,000Additions$685,200Total$749,200
Tax Record2024$47,175 ($3,931 / month)
Home Facts
Beds14Baths4Total Finished SqFt16,476 SqFtAbove Grade Finished SqFt16,476 SqFtStories2Lot Size871,200 SqFtStyleMiscellaneous ResidentialYear Built1989ZoningRR2CountySULLIVANAPN484689 56.-1-56.2

Schools near 399 Gregory Road

This home is within Monticello Central School District.
Rating
School
Type
Grades
Distance
Kenneth L Rutherford School
Public - 3 to 5
Robert J Kaiser Middle School
Public - 6 to 8
Monticello High School
Public - 9 to 12
George L Cooke School
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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More information about 399 Gregory Road, Monticello, NY 12701

399 Gregory Road is a single family home for sale in Monticello, NY 12701. This property was listed for sale on April 19, 2026 by Catskills Home Services, it's currently listed at $5,000,000. It has been on the market for a total of 45 days and was last sold on May 4, 2022. This listing's school district is Monticello Central School District. Nearby schools include Kenneth L Rutherford School, Robert J Kaiser Middle School and Monticello High School. 399 Gregory Road is a 14-bed, 17-bath, 17,570 sqft single family home built in 1989.

No guarantee, warranty or representation of any kind is made regarding the completeness or accuracy of descriptions or measurements (including square footage measurements and property condition), such should be independently verified, and Compass, Inc., its subsidiaries, affiliates and their agents and associated third parties expressly disclaims 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 discretion of the seller. 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.