Monticello Homes with Covered Parking features

Welcome to Monticello, New York – a hidden gem nestled in the heart of Sullivan County. Known for its vibrant community and stunning natural beauty, Monticello offers a perfect blend of small-town charm and modern conveniences. With its rich history, diverse culture, and proximity to the breathtaking Catskill Mountains, this city is an ideal place to call home.

Monticello is not just a haven for outdoor enthusiasts; it also boasts a thriving downtown area filled with unique shops, delightful restaurants, and engaging entertainment options. Whether you're exploring the local farmer's market or enjoying a leisurely stroll through the picturesque parks, you'll find plenty of opportunities to connect with your neighbors and soak in the community spirit.

One of the standout features of homes in Monticello is the availability of properties with covered parking. Imagine stepping out of your car and into your home, sheltered from the elements! Covered parking not only provides protection for your vehicle but also adds an extra layer of convenience to your daily routine. Whether you’re braving the winter snow or enjoying a sunny summer day, having a designated space for your car enhances your living experience.

Monticello's real estate market offers a range of homes that cater to various lifestyles, making it easy to find the perfect fit for you and your family. Discover the comfort and ease of life in Monticello, where every day feels like a getaway, and your dream home awaits with the added benefit of covered parking. Come explore the possibilities in this charming city!

Newest Monticello Homes with Covered Parking features

$5,000,000

14 Beds ⋅ 17 Baths ⋅ 976893 MLS

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.

399 Gregory Road, Monticello

Start Your Search

© 2026 TReND. All Rights Reserved.
The data relating to real estate for sale on this website appears in part through the TReND Internet Data Exchange (IDX) program, a voluntary cooperative exchange of property listing data between licensed real estate brokerage firms in which Real Broker NY LLC participates, and is provided by TReND through a licensing agreement. Real estate listings held by brokerage firms other than Real Broker NY LLC are marked with the IDX icon and detailed information about each listing includes the name of the listing broker.
All information provided is deemed reliable but is not guaranteed. Some properties which appear for sale on this website may no longer be available because they are under contract, have sold or are no longer being offered for sale. The information being provided is 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.

Listings courtesy of OneKey® MLS as distributed by MLS GRID. Based on information submitted to the MLS GRID as of . 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.