399 Gregory Road
About This Property
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.
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What does this mean?
Based on our analysis, the cap rate of this property is 1.25%. A negative cap rate indicates that the property might not be feasible as an income-producing asset. The median cap rate for a near zip code 11238 is 4.23%.
How much can I actually make?
Actual monthly rental income may vary between $4,760 and $7,140 depending on unit-specific characteristics. You can change the amount using the slider to further explore.
How is cap rate calculated?
Cap Rate = Net Operating Income (NOI) / Property Asset Value.
When calculating the cap rate, we assume 100% occupancy. Leverage (mortgage) is not considered.
Cap Rate provided by RealtyHop and RentHop, learn more about cap rate here.
Price History
| Date / Event | Date | Event | Price |
|---|---|---|---|
| Apr 8, 2026 | Listed by Catskills Home Services | $5,000,000 | |
| Listed by Catskills Home Services | |||
| May 16, 2022 | Sold | ||
| Sold | |||
| Jan 19, 2022 | No longer available | - | |
| No longer available | |||
| Nov 30, 2021 | Relisted | $1,999,999 | |
| Relisted | |||
| Nov 29, 2021 | No longer available | - | |
| No longer available | |||
Phone: 425-283-2930
Address: 335 Madison Avenue, New York, NY 10017