Monticello Homes with Oversized Parking features

Welcome to Monticello, New York—a charming town nestled in the heart of Sullivan County, renowned for its vibrant community and excellent educational opportunities. The Monticello School District is dedicated to fostering a nurturing and stimulating environment for students, making it a top choice for families seeking quality education. The district boasts a range of programs designed to cater to diverse learning needs, from innovative STEM initiatives to arts and athletics, ensuring that every child has the opportunity to thrive.

In addition to its outstanding educational offerings, Monticello is the perfect place to call home, especially for those in need of oversized parking options. Many properties in the area feature spacious parking solutions, accommodating everything from multiple vehicles to recreational toys like boats and RVs. This added convenience allows residents to enjoy the beautiful Sullivan County landscape without the hassle of finding parking space.

Imagine coming home to a lovely residence that not only meets your needs but also offers the luxury of ample parking. Whether you're hosting family gatherings, embarking on weekend adventures, or simply enjoying the serenity of your surroundings, having oversized parking can make all the difference.

Monticello is more than just a place to live; it’s a community where education flourishes, and families can create lasting memories. Explore the homes available in this delightful town, and discover how you can enjoy the perfect blend of comfort, convenience, and community in Monticello, NY!

Newest Monticello Homes with Oversized Parking features

$469,000

3 Beds ⋅ 2 Baths ⋅ 1017024 MLS

Nestled on more than 5 private acres in beautiful Sullivan County, this move-in-ready home offers the perfect blend of comfort, space, and convenience. Known for its abundant outdoor recreation, Sullivan County provides endless opportunities for fishing, boating, hiking, and enjoying nature. The home features two first-floor bedrooms, including a spacious primary suite complete with its own fireplace and a luxurious en-suite bath featuring a soaking tub. Hardwood floors flow throughout the main living areas, while the oversized living room showcases a cozy wood-burning fireplace. A formal dining room and a full bathroom with double sinks add both functionality and charm. The well-appointed kitchen offers stainless steel appliances, a breakfast bar, a premium Viking range, and sliding glass doors leading to the fenced backyard and detached two-car garage. Upstairs, you'll find two additional rooms with newer carpeting, offering flexibility for guest rooms, home offices, or hobby spaces. The partially finished full basement provides additional living space ideal for a family room, recreation room, or home gym. Conveniently located just minutes from Highway 17, this property is ideal for commuters while still offering privacy and tranquility. Enjoy easy access to popular destinations including Resorts World Catskills, The Kartrite Resort & Indoor Waterpark, Bethel Woods Center for the Arts, and LEGOLAND. Come experience the beauty, privacy, and endless possibilities this exceptional property has to offer!

2643 State Route 209, Wurtsboro

$1,359,000

3 Beds ⋅ 3 Baths ⋅ 1009055 MLS

The Builder’s Personal Lakefront Masterwork. Crafted by its original owner, a meticulous contractor who built it for his own home. Designed with intention: cherry cabinetry and floors, cedar ceilings, ductless air, and an over-engineered foundation built to last. Wolf Lake: 1,800private acres of untouched forestland, miles of maintained hiking trails, three pristine spring-fed bodies of water, and a clubhouse with a full calendar of events. Wolf Lake is a community that is unmatched in its natural amenities and desirability, while just 90 min from the GWB. Wolf Lake is a very desirable community with its private lakes and picturesque surroundings, surrounded by natural forests and privacy. Welcome to 164 South Shore Drive, a stunning lakefront home with 4800 sq. ft., located in the picturesque community of Wolf Lake. Located in Rock Hill, New York. This beautiful property was built in 2008 and offers a perfect blend of modern amenities and classic charm. With 2 full bathrooms, 1 half bathroom, a spacious 2,800-square-foot living area, and a 1,800-square-foot walkout semi-finished basement, this three-story home is perfect for those seeking a peaceful retreat in the countryside. The home sits on a 22,000-square-foot lot, providing plenty of space for outdoor activities and entertaining guests. The tranquil surroundings make this property a true oasis away from the hustle and bustle of city life. As you step inside, you will be greeted by a warm, inviting atmosphere, with abundant natural light flooding in through large windows and a cathedral ceiling, overlooking Wolf Lake. The open concept layout of the main floor creates a seamless flow between the living room, dining area, and kitchen, making it the perfect space for hosting gatherings or relaxing with loved ones. The kitchen is a chef's dream, featuring modern appliances, ample cabinet space, and a center island with a second sink for added convenience. This kitchen has everything you need to create delicious dishes. The master suite has 2 closets and an ensuite bathroom, complete with a luxurious soaking air tub and separate oversized shower. Upstairs, you will find 1100 sq. ft. of spacious bedrooms and bathrooms, each offering comfort and privacy. Plus, an expansive balcony area looking out over the lake. The lower level of the home is a versatile space that can be used as a home office, gym, rec area, work, or additional living area. With direct access to the backyard, this area offers endless possibilities for customization to suit your lifestyle. Outside, the backyard is perfect for enjoying the fresh air and soaking up the landscape's natural beauty. An expansive view of the lake can be enjoyed from the deck off the first-floor living room or the patio outside the sliding doors from the basement. Whether you're hosting a barbecue, playing with pets, or simply relaxing on the patio, this outdoor space is sure to become your favorite spot to unwind. Fishing and swimming are optional! Located off the beaten track in a privately owned community featuring a 330-acre lake, 2–30-acre ponds, and 1800 acres of forest and trails, bordering thousands of acres of protected NYS land. The community offers a clubhouse, a sandy beach with lifeguards, and a private rifle range for target practice and trap shooting. This community is shareholder-owned by the community in the town of Rock Hill, NY. This property offers the perfect combination of privacy and community charm. With easy access to local amenities, schools, and outdoor recreational opportunities, this home truly has it all. Don't miss your chance to make 164 South Shore Drive your own slice of paradise in the Hudson Valley. One-time Wolf Lake membership fee of $5,250.

164 S Shore Drive, Wurtsboro

$849,900

3 Beds ⋅ 2 Baths ⋅ 999825 MLS

On any lake, the lot is everything and this property delivers the kind of waterfront that is increasingly difficult to find: level to gently sloping, just three steps down from the deck to the waterfront, a natural pebble-and-sand swimming area, and a private dock, all without the steep grades or soft bottoms that define so many lakefront parcels in the region. The lake-facing wall of windows fills nearly every main living space with water views, while lakeside deck, newly built in 2025, extends the living area directly toward the shoreline. This well-maintained chalet offers 3 bedrooms and 2 full baths across 1,767 square feet, with an open layout that provides genuine first-floor flexibility. Two bedrooms and a full bath are located on the main level, allowing comfortable single-level living if desired. Upstairs, the nearly 24x17 primary suite occupies the entire second floor, complete with its own bath and an open loft-style overlook toward the great room and lake below. Major infrastructure improvements are already in place, including a new house roof (2020), new deck (2025), new garage roof (2025), exterior painting (2021), propane hot water baseboard heat, drilled well, septic, and a detached oversized two-car garage with approximately 600 square feet of space plus a large stand-up storage loft accessible by a legitimate staircase. Located within Wolf Lake, one of Sullivan County’s most sought-after private lake communities, members enjoy access to approximately 1,800 acres of protected forestland, 3 spring-fed lakes, community beach, clubhouse, basketball court, playground, and recreational facilities, all approximately 90 minutes from the George Washington Bridge. Annual HOA: $1,350. One-time new-member fee of $5,250.

382 S Shore Drive, Rock Hill

$299,000

3 Beds ⋅ 1 Baths ⋅ 987715 MLS

Beautifully preserved and thoughtfully updated, this original 1930 Smallwood cabin offers the perfect balance of rustic charm and modern comfort. Immaculately maintained, the home features restored original wood floors, a bright and airy interior, and an inviting layout designed to bring the outdoors in. The sun-filled living space is complemented by a stone fireplace with insert, providing both ambiance and efficiency, along with a highly effective heating system for year-round comfort and central air for warmer months. Additional features include a renovated bathroom, partial basement with laundry, well and septic systems, and a brand-new paved driveway. Ideally located within walking distance to the lake, mini falls and scenic hiking trails, this property also offers optional membership to the Smallwood Civic Association ($350 annually per household), granting access to the community beach, lake, and amenities including boating. Enjoy close proximity to lakeside dining, Golf Course, Bethel Woods Center for the Arts, with Resorts World Catskills casino just a short drive away. Short-term rentals are permitted in the area, offering excellent investment potential. All of this, just under two hours from New York City.

64 Cumberland Trail, Smallwood

$1,550,000

4 Beds ⋅ 4 Baths ⋅ 967208 MLS

Just 90 minutes from New York City, this custom 4-bedroom, 4-bathroom ranch residence set on 5+ private acres offers a rare balance of craftsmanship, scale, and pastoral beauty. Designed to capture both light and landscape, the home welcomes you with towering windows in the kitchen and main living spaces, where expansive views of open land and sky become part of the daily experience. Inside, the architecture celebrates handcrafted detail and natural materials. Solid wood finishes, artisan carvings, soaring ceiling heights, and a dramatic catwalk overlooking the main living area create warmth and visual impact. A private movie room adds comfort, making the home equally suited for entertaining or quiet evenings. The surrounding acreage invites a slower rhythm of life. Longhorn cattle grazing nearby enhance the authentic ranch setting, while the open land provides space well-suited for equestrian living. Properties offering luxury homes with acreage within 90 minutes of NYC are increasingly rare. Here, buyers can step directly into a completed residence: no construction timelines, no waiting: simply the opportunity to begin living the ranch lifestyle from day one.

55 Chapin Trail, Bethel

$464,900

3 Beds ⋅ 3 Baths ⋅ 938403 MLS

Get ready to fall in love with this charming New England style farmhouse in a most desirable location. Beautifully arranged with plenty of room for entertainment and relaxation this is a real treat. Well-appointed interior with wood floors and warm original details offers space for everyone to spread out and enjoy. The large eat-in kitchen boasts an island and granite counters with cabinets galore and upscale appliances. French doors open to formal living room with gas fireplace, and the cozy formal dining room is just around the corner. Sitting room/ den leads to the glorious sunroom which overlooks the peaceful meadow view. Upstairs offers three bedrooms and full bath with soaking tub and lots of storage space. Lower level is occupied by the finished flex room, full bath, laundry room plus a one car garage and utility room. Spacious yards in front and rear offer expansive areas for gardening, pets and play. The oversized detached 2-car garage is a huge plus and is heated. This is a terrific set up for all sorts of workshops and a hobbyist’s dream come true. Generac whole house generator completes the package. Active farm across the street and Bethel Woods just down the road makes this an ideal location for year-round living or getaway country retreat.

237 Best Road, Swan Lake

$399,999

3 Beds ⋅ 2 Baths ⋅ 886753 MLS

Adorable Spacious 5.02 acre lot with lots of fruit trees, berry trees and garden area. 3 bedrooms, 1.5 Bath. This gem offers the perfect blend of character and functionality. Enter to a spacious mudroom with windows and sky light to find a light-filled living room, a formal dining area with all window walls and sky light. Home features 1 wood burning fireplace and two wood stoves. A workshop is attached to the rear of the home and also has a wood burning fire stove. Home and property features ample storage, multiple wood and storage sheds on property. Oversized 1 car detached garage. Eat in the kitchen to supplement a generous sized dining room with lots of space and a wood burning stove for perfect relaxed evenings. Plenty of gardening areas, most of the land is leveled and cleared. Fruit trees include Mulberry, Chestnut, Peach, Apple, Cherry, Black berry, Raspberry, Grapes and pear. Located just minutes from schools, shopping, restaurants and major highways, this home offers both comfort and convenience in a central location.

139 Haddock Road, Monticello

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