399 Gregory Rd , Monticello, NY 12701
$5,000,000
- 14
- beds
- 12 full · 3 half
- baths
- 17,570
- sqft
- 1989
- year built
$5,000,000
399 Gregory Rd , Monticello, NY 12701
- 14
- beds
- 12 full · 3 half
- baths
- 17,570
- sqft
- 1989
- year built
- Status:
- Active
- MLS #:
- 976893
- County:
- Sullivan
- Listed By:
- Rivky Klagsbrun - Catskills Home Services
- Office Phone:
- (845) 397-7768
- Agent Email:
- theklagsbrunpromise@gmail.com
Sponsoring Broker: Steven Domber, Berkshire Hathaway HomeServices Hudson Valley Properties
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.
Highlights
- Residential
- Single Family Residence
- Built in 1989
- 20.0 Acre Lot
- 2 Car Garage
- 207 days on Market
-
- Bedrooms
- 14
-
- Bathrooms
- 12 full · 3 half
-
- Year Built
- 1989
-
- Architectural Style
- Estate
-
- Construction Materials
- Stone
-
- Garage Spaces
- 2.0
-
- Parking Features
- Driveway, Garage, Covered, Parking Lot
-
- Living Area
- 17570.0
-
- Interior Features
- High Speed Internet, Storage, Granite Counters, High Ceilings, Entrance Foyer, Chandelier, Sound System
-
- Appliances
- Dryer, Dishwasher, Refrigerator, Washer, Tankless Water Heater, Oven, Gas Oven, Freezer, Exhaust Fan
-
- Flooring
- Hardwood, Vinyl, Carpet, Ceramic Tile
-
- Exterior Features
- Lighting, Gas Grill, Fire Pit, Playground
-
- Patio And Porch
- Patio, Deck
-
- Pool Features
- In Ground, Private, Indoor
-
- Security Features
- Smoke Detector(s)
-
- Cooling
- Central Air
-
- Heating
- Forced Air
-
- Basement
- Partial, Unfinished, Storage Space
-
- Acres
- 20.0
-
- Lot Features
- Wooded, Views, Private, Landscaped, Back Yard, Front Yard
-
- Water Front Features
- Stream, Waterfront Access
-
- View
- Trees/Woods
-
- Utilities
- Electricity Connected
-
- Water
- Private, Well
-
- County
- Sullivan
-
- City
- Monticello
-
- Zip Code
- 12701
-
- High School
- Monticello High School
-
- Middle School
- Robert J Kaiser Middle School
-
- Elementary School
- George L Cooke School
-
Ask a Question
ez Mortgage Calculator
Enter your details below to estimate your monthly mortgage payment with taxes, fees and insurance.
Please enter a valid number
Cost of the current home: $5000000
Please enter a valid number
Cash you pay when you close
Affects interest rates. 30- or 15- year loans are standard.
Default rate is illustrative, set internally by ez Home Search and updated periodically; actual rates vary by lender, credit score, and market conditions.
Please enter a valid number
Please enter a valid number
Typically 0.25% of home value per year.
Please enter a valid number
Homeowners association dues.
$ 0
Monthly
Principal and interest:
Property Taxes:
Homeowners Insurance:
HOA Dues:
$0 (0%)
$0 (0%)
$0 (0%)
$0 (0%)
The ez Mortgage Calculator is for educational purposes only. Real-world interest rates and payments can differ due to factors like market trends, location, and loan specifics. Calculations are based on your inputs and might not consider extra costs a lender may add, such as insurance, taxes, and fees; thus, actual repayments could surpass estimates. Please note, ez Home Search does not provide loans, and this tool does not promise lending.
Price History
| 04/18/2026 | Listed | $5,000,000 |
| Source: OneKey MLS #976893 | ||
Source: MLS Data
Deed History
| 05/16/2022 | Deed | $1,378,500 |
| 07/30/2010 | Intrafamily Transfer - Transaction is between related parties for any reason & no consideration. | $0 |
| 02/02/2010 | Intrafamily Transfer - Transaction is between related parties for any reason & no consideration. | $0 |
| 02/28/2003 | Quit Claim Deed (non-arm's length) | $0 |
| 01/10/2003 | Intrafamily Transfer - Transaction is between related parties for any reason & no consideration. | $0 |
| 12/30/2002 | Deed | $345,000 |
| 05/27/1998 | Deed | $188,000 |
Source: Public records via Constellation Data Labs
Mortgage History
| 02/02/2024 | Stand Alone Refi (Refinance of Original Loan) | $178,250 |
| 05/16/2022 | Commercial | $2,102,400 |
| 03/18/2019 | Stand Alone Refi (Refinance of Original Loan) | $43,263 |
Source: Public records via Constellation Data Labs
What's your home worth?
Calculate your current home value within seconds.
Frequently Asked Questions
How do I schedule a tour of 399 Gregory Rd?
We can make that happen quickly. Click Tour This Home and we'll connect you directly with our vetted local partner to schedule your visit to 399 Gregory Rd.
They know residentials in the area well and can give you the guidance you need to buy with confidence.
How do I get more information about 399 Gregory Rd?
Click Ask a Question to talk with our team. You already know it is a 14 bed, 12 bath, listed for $5,000,000. We can talk through recent upgrades, potential seller motivation, how this single family residence compares to others in Monticello, and can even get you in to see the property quickly.
How much is the monthly mortgage payment for 399 Gregory Rd?
With a 20% down payment and a 30-year fixed loan at an illustrative 7.25% rate, the ez Mortgage Calculator estimates the monthly payment for 399 Gregory Rd at around $31,058. This includes estimated property taxes and insurance.
Want to see how this changes with different down payments or interest rates? Jump to the calculator to run the numbers and fine-tune your plan.
How do I get pre-approved to buy 399 Gregory Rd?
Stand out in a competitive market by getting pre-approved today. Our quick and private pre-approval process helps you understand your true buying power—no credit pull required to explore all of your options.
Or, let us connect you with our preferred local lender in Sullivan County. They will give you all of your available financing options, based on your specific situation and what is available to you.
Can I negotiate the asking price for 399 Gregory Rd?
In most cases, yes. Whether 399 Gregory Rd is priced competitively or not, your best offer depends on your personal situation, the seller's timeline, and recent activity in Monticello's market. Our preferred local partner will help you craft a strategy—factoring in comparable properties that have sold, timing, and deal structure—to make a smart, strong offer. Click here to ask about negotiation opportunities.
How do I make an offer on 399 Gregory Rd?
We can handle that for you. Our preferred local agent specializes in residentials in Monticello and can guide you through every step of the offer process.
You need an expert who is looking out for your best interests. From market valuation to contingencies and timing, they'll help you present a compelling offer that fits your goals. Click Ask a Question to get started today.
What is the price per square foot for this home?
This home is listed at $5,000,000 with 17,570 sqft of space—that comes out to approximately $285 per square foot.
How long has this property been on the market?
399 Gregory Rd was listed on April 18, 2026, which means it's been on the market for 207 days.
Want to keep tabs on it? Click the ♥ to favorite this home and get notified of price drops or changes.
When was this house built?
This home was built in 1989, making it approximately 37 years old.
What is the lot size of this property?
399 Gregory Rd sits on a 20.0-acre lot, which is 871,200 square feet.
What schools are assigned to this property?
Based on MLS info, this home is zoned for:
- Elementary: George L Cooke School
- Middle: Robert J Kaiser Middle School
- High: Monticello High School
Want to see how these schools compare? Check out our Sullivan County School Guide to see ratings, reviews, and more for the schools in the area.
What are the property taxes for 399 Gregory Rd?
The most recent public record shows annual property taxes for 399 Gregory Rd were approximately $31,248. This may change with reassessment or exemptions. Our local partner can verify current tax amounts and help you estimate future costs based on your situation.
Is 399 Gregory Rd still available for sale?
Yes, this home is still available! Click the ♥ to favorite it so you don't miss any changes—or ask our local expert to schedule a time to see it in person.
Source: ez Home Search, MLS Data
Popular Home Searches in Monticello, NY
Open Houses Near Monticello, NY
Land for Sale Near Monticello, NY
Townhomes for Sale Near Monticello, NY
Waterfront Homes for Sale Near Monticello, NY
Waterfront Condos for Sale Near Monticello, NY
Homes with Pools for Sale Near Monticello, NY
Gated Community Homes for Sale Near Monticello, NY
Homes with No Hoa for Sale Near Monticello, NY
Homes in Adult Communities for Sale Near Monticello, NY
Search Nearby Cities
Search Nearby Postal Codes
Listing information 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. Information deemed reliable but not guaranteed by the MLS. The listing broker’s offer of compensation is made only to participants of the MLS where the listing is filed. Copyright 2026, OneKey MLS. All rights reserved.
Last Updated: November 11, 2026 at 12:17AM | Source: OneKey MLS | MLS#: 976893
