About this home

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.

Facts and features

Schools

• Monticello High School

  high · 9-12 · 4.7 mi

  3

• Robert J Kaiser Middle School

  middle · 6-8 · 4.7 mi

  2

• Kenneth L Rutherford School

  elementary · 3-5 · 4.9 mi

  3

• George L Cooke School

  elementary · K-2 · 5.8 mi

• Emma C Chase School

  elementary · K-5 · 15.2 mi

  7

Price history

• Jun 30, 2026 · Listing Removed$1
• Jun 30, 2026 · Listing Removed$2,300,000
• May 7, 2026 · Listing Removed$5,000,000
• Apr 20, 2026 · Listed$5,000,000
• May 7, 2024 · Listing Removed$3,999,999
• May 7, 2024 · Listing Removed$1,999,999
• May 16, 2022 · Sold$1,378,500
• May 15, 2022 · Listing Removed$2,499,000

Tax history

• 2026$31,248 tax · $749,200 assessed
• 2025$30,844 tax · $749,200 assessed
• 2024$30,120 tax · $749,200 assessed
• 2023$29,082 tax · $747,200 assessed
• 2022$29,027 tax · $747,200 assessed
• 2021$29,277 tax · $747,200 assessed
• 2020$46,082 tax · $747,200 assessed
• 2017$44,506 tax · $747,200 assessed

Home value

$4,801,900

• Cotality$4,801,900
• Collateral Analytics$4,950,000
• Quantarium$2,238,596

Where it is