Monticello Homes with Landscaping Amenities

Welcome to the enchanting Monticello School District, nestled in the heart of Sullivan County, NY. This vibrant community is not only known for its scenic beauty but also for its commitment to providing an exceptional educational experience for its students. The Monticello School District prides itself on fostering a nurturing environment where children can thrive academically and socially. With a variety of programs, dedicated educators, and a focus on innovative learning, families can feel confident that their children are receiving a top-notch education.

As you explore the Monticello area, you’ll discover a range of stunning homes that truly reflect the beauty of the region. Many properties boast exquisite landscaping amenities, creating a picturesque setting that complements the natural charm of Sullivan County. Imagine stepping into your backyard, surrounded by lush gardens, vibrant flowers, and meticulously maintained lawns—perfect for family gatherings, outdoor entertaining, or simply unwinding after a long day.

The combination of quality education and beautiful homes makes Monticello an ideal destination for families looking to settle down. With easy access to local parks, recreational activities, and community events, residents can enjoy a well-rounded lifestyle in a welcoming atmosphere. Whether you’re searching for a cozy cottage or a spacious family home, Monticello offers a variety of options to suit your needs.

Experience the charm of Monticello, where exceptional schools and beautiful homes with landscaping amenities come together to create a perfect place to call home. Discover your dream property today and become part of this vibrant community!

Newest Monticello Homes with Landscaping Amenities

$475,000

3 Beds ⋅ 3 Baths ⋅ 1031746 MLS

Nestled within the sought-after Greentree community, this beautifully renovated three-bedroom, three-bath residence offers an exceptional blend of timeless design, quality craftsmanship, and low-maintenance living. Thoughtfully renovated throughout, the home showcases a custom KraftMaid kitchen with abundant cabinetry, quality finishes, and an open layout that flows effortlessly into the spacious living and dining areas. Rich oak flooring extends throughout the main level, while soaring vaulted ceilings, skylights, and oversized windows fill the home with natural light, creating an inviting atmosphere designed for both everyday living and effortless entertaining. The well-appointed floor plan offers three generously sized bedrooms, including a distinctive loft-style upper-level suite that provides flexible space for guests, a home office, or an additional family room. Two beautifully renovated bathrooms feature marble flooring, classic beveled subway tile, and timeless finishes that reflect the home’s thoughtful attention to detail. Greentree is a private lakeside community known for its beautifully maintained grounds and exceptional amenities, including a clubhouse, heated swimming pool, tennis and basketball courts, playground, and a full calendar of community events. The homeowners association also provides exterior maintenance, roof care, snow removal, trash service, and upkeep of the common areas, allowing for a truly turnkey lifestyle. Whether you’re seeking a full-time residence or a seasonal getaway, this thoughtfully renovated home offers a rare opportunity to enjoy refined interiors, outstanding community amenities, and the ease of carefree ownership.

42 Lakeview Terrace, Monticello

$389,000

2 Beds ⋅ 3 Baths ⋅ 1020730 MLS

Welcome to 2 Sylvia Lane, a spacious 3-bedroom, 3-bathroom duplex home located in the desirable Greentree Community of Monticello. This well-maintained property offers comfort, convenience, and low-maintenance living. Enjoy parking right in front of the home, a short walk to the community clubhouse, and easy access to Resorts World Casino, Kartrite Waterpark, and local shopping. The HOA takes care of snow removal, garbage, exterior painting, and even roof replacement, making homeownership simple and worry-free. Community amenities include a pool, clubhouse, and serene lake access perfect for kayaking. Priced to sell and ready for summer enjoyment

2 Sylvia Lane, Monticello

$1,295,000

4 Beds ⋅ 4 Baths ⋅ 989403 MLS

Anchored gracefully along four hundred feet of shoreline on the Peninsula at the Chapin Estate, Whispering Oak Landing is a country retreat like no other. This custom-built legacy lakefront home constructed by the current owner, is nestled beneath majestic oaks and surrounded by five enchanting acres of untouched woodland. Discretely tucked within an exclusive 2,500-acre gated wilderness preserve, the property offers the perfect blend of privacy and security, just two hours from Manhattan and fifteen minutes from the new Sullivan County International Airport. Once inside, a vaulted foyer crowned by a crystal chandelier opens to expansive, sunlit gathering spaces. Adjacent to the front entrance, a convenient powder room sits across from a bright, oversized laundry room with a utility sink, exterior door, and interior access to the two-car garage. The main level is composed of a warm and inviting living room with a classic wood-burning fireplace, a professionally appointed kitchen with dual sinks, and seamless indoor-outdoor dining areas complete with a built-in grill. The vaulted, east-facing primary suite, a standout feature, is also located on this level for effortless single-floor living, and features tranquil wooded lake views from an oversized picture window. The en-suite bath is a sanctuary of indulgence, complete with a windowed soaking tub, dual vanities, walk-in shower, and refined finishes. A stately walk-in closet, discreetly accessed from the private hallway, completes this restful retreat with both elegance and practicality. Upstairs, two well-proportioned bedrooms are positioned at either end of the home and connected by an open corridor with railings that overlook the main living area below. A naturally lit shared bathroom serves both rooms. One bedroom features a charming Juliette balcony, while the other includes a spacious, unfinished dormer room above the garage, offering excellent potential for future expansion. Downstairs, the lower level provides a cozy and versatile relaxation space, including a fourth full bedroom and an additional room ideal for fitness, a reading lounge, or a fifth bedroom. Designed with comfort and entertainment in mind, this level is also outfitted with a full wet bar, a cedar sauna, full bath, and an expansive secondary living room that opens to a graceful flagstone terrace, perfect for indoor-outdoor relaxation. Architectural highlights include soaring ceilings with exposed pine beams, wide-plank hardwood floors, granite countertops, and central air conditioning, thoughtfully designed to enhance a true year-round living experience. Sunlight pours into the home from dawn to dusk, creating an inviting atmosphere throughout the day. Additional practical features such as insulated windows and a central alarm system ensure ease of ownership and lasting peace of mind. Surrounding the home, the Chapin Estate spans 2,500 acres of pristine forest and borders 14,000 acres of protected conservation land. Community amenities include 2,000 acres of freshwater reservoirs and trout streams, and over nine miles of hiking and riding trails. With panoramic views of the 900 acre Toronto Reservoir and its untouched wilderness borders, the home is perfectly positioned for serene mornings on the water and adventurous days of boating, swimming, and paddling. Enjoy close proximity to the Eldred Preserve, an upscale boutique hotel featuring the Homestead Restaurant, a local farm to table dining experience. Minutes from the Bethel Woods Center for the Arts and the Monticello Motor Club, Whispering Oak Landing offers a rare lifestyle of timeless design, seamless connection to nature, and effortless access to the best of the Catskills, one that few will ever experience, and even fewer will be fortunate enough to call home.

51 Homestead Trail, White Lake

$130,000

988112 MLS

Distinctly positioned just below the spring-fed source of Black Lake, this iconic woodland homesite stretches along roughly six hundred feet of crystal-clear water. A true four-season stream-side sanctuary, Black Lake Creek is a coveted brook-trout habitat. The property features heritage stone formations, towering oaks, and private woodland seclusion. Set at the headwaters of the Toronto Reservoir and tucked behind the gates of The Chapin Estate, this fully buildable lot is ready for immediate construction. The Chapin Estate encompasses over 2,500 acres of preserved wilderness surrounding approximately 1,750 acres of freshwater lakes. This gated, year-round residential community is renowned for luxury second homes and its close proximity to New York City. Membership to the private, residents-only Lake Club is optional for this homesite. Within the gates, The Chatwal Lodge is located just one mile away, offering dining now and spa services forthcoming. Owners may also obtain a boat slip at the Lake Club, granting access to both Toronto Reservoir and Swinging Bridge Reservoir. Photos and lot lines are provided for marketing purposes only. Buyer to verify all information prior to sale.

Chapin Trail, White Lake

$150,000

951393 MLS

This beautifully wooded and pastured lot is just within the main gates of The Chapin Estate. Just over 5 acres with 584' of stream frontage on Black Lake Creek. Homesite must be 50' from property line. This site requires a septic system, drilled well and underground electric to homesite. This is an approved building lot with electric and cable at road. Driveway cut was made to the most desirable home site. The lot borders Black Lake Creek which feeds into the 900+/- acre Toronto Reservoir. The Toronto Reservoir is known for its fishing, kayaking, paddle boarding, water skiing and swimming. Gasoline engines are permitted with a 20' maximum vessel length. This is a 4 season, gated, residential community that consists of 2500 acres of preserved lands that border 2000 acres of freshwater lakes. This prestigious community is known for its luxury vacation homes and its close proximity to NYC. The member's only Lake Club within the gates is optional or this particular homesite. The Chatwal Lodge is a luxury boutique hotel located a mile from this property within the gates of The Chapin Estate. The hotel is open for business and amenities to be offered to residents in the future. Floor plans for a 4-bedroom New England Style home are included with the purchase of this lot. *Short term rentals are not permitted. Rental minimum of 3 months no more than twice per year. **All appointments requests need 24 Hour notice; the HOA does not permit drive up showings or grant access through the gates without a confirmed appointment for the security of our residents. Owner Financing is Available.

Lot 4 Chapin Trail, Bethel

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