399 Gregory Road
Monticello, NY 12701
14
Bed
17
Bath
17,570Sqft
20Acres(Lot)
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
Property Details
Map
Map
What's Nearby
Nearby Areas
Features
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Bedroom Information
Total beds: 14Bathroom Information
Total Baths: 17 Full Baths: 12 Half Baths: 5Room Information
Rooms Total: 9 Basement: Partial, Storage Space, Unfinished -
Flooring Information
Carpet, Ceramic Tile, Hardwood, Vinyl -
Interior Features
Chandelier, Entrance Foyer, Granite Counters, High Ceilings, High Speed Internet, Sound System, Storage Appliances: Dishwasher, Dryer, Exhaust Fan, Freezer, Gas Oven, Oven, Refrigerator, Washer, Tankless Water Heater Laundry Features: Multiple Locations Window Features: Skylight(s) -
Heating & Cooling
Has Heating: Yes Heating: Forced Air Has Cooling: Yes Cooling: Central Air
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Building Information
Year Built: 1989 Construction Materials: Stone Patio And Porch Features: Deck, Patio Pool Features: In Ground, Indoor, Private Private Pool: Yes Water front Features: Stream, Waterfront Access View: Trees/Woods -
Exterior Features
Exterior Features: Fire Pit, Gas Grill, Lighting, Playground
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Lot Information
Lot Size Acres: 20 Lot Size Square Feet: 871200 Lot Description: Back Yard, Front Yard, Landscaped, Private, Views, Wooded
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Listing Price Information
Listing Price: $5000000
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Tax Information
Parcel Number: 4689-056-0-0001-056-002 Tax Lot: 1 Tax Block: 56 Annual Tax: $31248
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Parking Information
Parking Total: 20 Covered, Driveway, Garage, Parking LotGarage Information
Has Garage: Yes Garage Space: 2
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School Information
Elementary School: George L Cooke SchoolJunior High School: Robert J Kaiser Middle SchoolSenior High School: Monticello High School -
Utility Information
Electricity Connected -
Location Information
Direction: GPS to 399 Gregory Road, Monticello, NY 12701. WaterSource: Private, Well Security Features: Smoke Detector(s)
How much is this property worth?
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Nearby Home Value
| Address | Estimate | Bed | Bath | Sq. Ft | Lot Size |
|---|---|---|---|---|---|
| 13.-3-14.2 Rock Ridge D.., Monticello, NY, 12701 | $495,000 | 3 | 3 | 2,192 | 2,192 SqFt |
| 119 Cimarron Road, Monticello, NY, 12701 | $349,999 | 3 | 3 | 1,795 | 1,795 SqFt |
| 33 Melody Lake Drive, Monticello, NY, 12701 | $199,999 | 3 | 1 | 1,248 | 1,248 SqFt |
| 139 Haddock Road, Monticello, NY, 12701 | $399,999 | 3 | 2 | 1,200 | 1,200 SqFt |
| 174 Rock Ridge Avenue, Monticello, NY, 12701 | $368,500 | 2 | 1 | 1,100 | 1,100 SqFt |
| 541 Cold Spring Road, Monticello, NY, 12701 | $524,999 | 3 | 2 | 1,512 | 1,512 SqFt |
| 36 Waverly Avenue #34, Monticello, NY, 12701 | $450,000 | 3 | 1 | 1,516 | 1,516 SqFt |
| 8 Waverly Avenue #44, Monticello, NY, 12701 | $585,000 | 3 | 2 | 1,354 | 1,354 SqFt |
| 20 Nelshore Drive, Monticello, NY, 12701 | $275,000 | 2 | 1 | 964 | 964 SqFt |
| 74 Nelshore Drive, Monticello, NY, 12701 | $399,000 | 4 | 3 | 1,693 | 1,693 SqFt |
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ByOwner last updated this listing 06/06/2026 @ 04:02
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