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

$524,000

4 Beds ⋅ 3 Baths ⋅ 1049763 MLS

Experience the best of both worlds with this furnished 2500 sq ft country home. You'll wake up in the mornings with deer in the backyard, yet you're only 15 minute drive from grocery stores and attractions. In the Rec Room, you'll find ballet barres and mirrors for a variety of home fitness activities. After your workout the sauna and hot tub will be your favorite place to recover. The wood burning fireplace is wonderful for those cold Catskills nights. Two decks and a patio to enjoy the mountain breezes, sunsets, and stars here in the Catskills. This home has a seven year track record as a successful short term rental. The existing management team is excited and willing to work with a new owner, and will convey with hundreds of positive reviews. Home can be purchased furnished if you desire to continue it as a STR/second home. For those wishing to purchase the home as primary residence, the home can be delivered empty and unencumbered by rentals. Full financials are available. Main Level Rooms: Open concept living area with large kitchen, bar seating, dining area and wood burning fireplace. The principal bedroom accommodates a king bed and has an ensuite full bathroom with shower. Bedroom 2 is queen size, and bedroom three will accommodate a full bed. There is an additional full bath on the main level with a shower/tub combo. Lower Level Rooms: The massive recreation room has ballet barres and a wall of mirrors. The media room opens out to a covered patio. The flex room is currently set up as bedroom four that accommodates a queen bed. The full bath with shower also includes an indoor infrared sauna. A full laundry room and multiple storage closets provide plenty of room for all your belongings or supplies for your short term rental. Outdoors: You will find multiple decks and a patio at the home. There is a fire pit in the backyard.

140 Starlight Drive, Monticello

$1,295,000

2 Beds ⋅ 2 Baths ⋅ 1045159 MLS

For those who believe the garage is the most important room in the house, welcome to Motor Club Estates. Set within the exclusive Monticello Motor Club community, this beautifully appointed two-bedroom, two-bath condo offers a rare combination of sleek and modern comfort, serious car storage, and a front-row seat to the Catskills’ most distinctive lifestyle destination. Offered fully furnished and move-in ready, the residence makes an effortless weekend escape or full-time home base. However the real showstopper may be right outside: a private garage with two installed lifts and capacity to accommodate up to eight cars - an exceptional setup for the car collector, enthusiast, or anyone whose idea of a well-appointed upstate escape includes ample for the collection. To keep your driving physique in tip-top shape, a fully equipped gym and indoor pool are right outside the condo’s front door. The Monticello Motor Club brings the country-club concept into decidedly higher gear. Its professionally designed circuit features 4.1 miles of race-grade asphalt, with a 3.6-mile Full Course offering 20 turns and 450 feet of elevation change. Club offerings include professional driving instruction, access to a high-performance fleet featuring BMW, Porsche, and Mazda race cars, karting, off-road experiences, vehicle maintenance and storage, and concierge services. Beyond the track, Monticello Motor Club offers the polish of a private club, with a member clubhouse overlooking the start/finish area, farm to table dining featuring seasonal Hudson Valley and Catskills specialities, private locker rooms, trackside viewing areas, event spaces, and a 16,000-square-foot Collector Car Gallery. Whether you're chasing lap times, collecting cars, or simply looking for an exceptionally fun Catskills escape, this is upstate living with a little more horsepower. Arrive, unpack, garage the toys, and enjoy. Vroom vroom!

11 Serenity Lane Unit #1A, Monticello

$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

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