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

$130,000

1050203 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.

Lot 3 Chapin Trail, White Lake

$425,000

3 Beds ⋅ 2 Baths ⋅ 1049558 MLS

Three bedrooms two Baths with one having stall shower and washer/ dryer. White oak floors refinished. All windows replaced and have been tinted allowing you to see out and nobody see in. All new shades most are remote. Front door has three panel each is motorized. Custom crown moldings in living and dining area. Two driveways with lots of room for cars. All appliances are included. Kitchen cabinets with pull-out doors for double storage and ceiling done to match cabinets. Generator with cross over panel. The home has 200- amp electric service. Home converted from electric to oil heat. Trek decking front and back. Full dry basement with storm drain. Low Taxes

142 N Emerald Drive, Rock Hill

$625,000

4 Beds ⋅ 3 Baths ⋅ 1047015 MLS

Welcome to this meticulously maintained and thoughtfully updated home in the desirable Emerald Green community, where comfort, quality, and resort-style living come together. With 4 bedrooms and 2.5 bathrooms, this pristine property is filled with carefully considered details designed for both everyday living and effortless entertaining. Enjoy a fully matted garage, durable Trex decking, and electric awnings that provide shade and comfort while you relax or entertain outdoors. Inside, the home offers an impressive array of amenities, including an 8-person cedar sauna, a Harman pellet stove insert, a beautifully appointed primary bathroom finished with Carrara marble, and custom wood cabinetry in the kitchen. An energy-efficient geothermal heating and cooling system provides an added benefit, offering the potential for significant savings on heating and cooling costs. Emerald Green offers an exceptional lifestyle centered around three lakes totaling approximately 330 acres. Residents enjoy two in-ground pools overlooking a lakeside sandy beach, a renovated indoor clubhouse with a gym, tennis, pickleball and basketball courts, playgrounds, and a dog run. Whether you're looking for recreation, relaxation, or a welcoming community atmosphere, Emerald Green has something for everyone. With its extensive updates, exceptional amenities, and access to one of the area's most sought-after communities, this home is ready to be enjoyed. Schedule your private showing today and make this beautiful Emerald Green property your own. The seller is also open to and would prefer having all furniture, rugs, Weber grill, crystal, and Lazy Boy furniture convey with the property, providing an opportunity for a truly turnkey experience.

61 Lake Shore Drive S, Rock Hill

$1,250,000

4 Beds ⋅ 4 Baths ⋅ 1034443 MLS

PRICE DROP! A magnificent legacy home in the Catskills’ most exclusive gated preserve. Discretely tucked beneath a canopy of mature oaks on five enchanting acres, Whispering Oak Landing is a custom, owner-built retreat within The Chapin Estate - a prestigious 2,500-acre gated wilderness preserve in the Western Catskills, surrounded by 14,000 acres of protected conservation land. Upon arrival, the rhythm of nature sets the pace: birdsong at first light, afternoons spent hiking or horseback riding along the preserve’s trails, and evenings that end with an indoor or outdoor fire crackling in your private sanctuary. Intentionally oriented to follow the suns path, morning light rises over the vaulted timber living room, while evening light settles beyond the foyer, where a crystal chandelier captures the last rays and scatters them in soft rainbows throughout the house. Inside, a soaring vaulted foyer opens onto expansive, sunlit gathering spaces. Just off the entrance, a convenient powder room sits opposite a bright, oversized laundry room complete with utility sink, exterior access, and direct entry to the two-car garage. The main level centers on a warm, vaulted living room anchored by a stone wood-burning fireplace, a professionally appointed kitchen with double sinks, and a seamless indoor-outdoor dining areas that include a propane grill. The vaulted, east-facing primary suite occupies this primary level for effortless single-floor living. An oversized picture window frames tranquil wooded lake views, while the en-suite bath offers a private sanctuary of indulgence: a windowed soaking tub, dual vanities, walk-in shower, and refined finishes. A stately walk-in closet, discreetly reached via a private hallway, completes the suite with both elegance and practicality. Upstairs, two well-proportioned bedrooms sit at opposite ends of the home, linked by an open corridor with railings that overlook the living spaces below. A naturally lit shared bathroom serves both. One bedroom opens onto a charming Juliet balcony; the other includes a spacious, unfinished dormer room above the garage, ready for future expansion. The lower level provides a cozy, versatile space for relaxation, featuring a fourth full bedroom and an additional flexible room ideal as a fitness studio, reading lounge, or fifth bedroom. Designed for comfort and entertaining, this level also includes a full wet bar, cedar sauna, full bath, and an expansive secondary living room that opens directly onto a graceful flagstone terrace, perfect for indoor-outdoor living. Architectural details throughout include soaring ceilings with exposed pine beams, wide-plank hardwood floors, granite countertops, and central air conditioning, all thoughtfully integrated for true year-round enjoyment. Life at The Chapin Estate unfolds across 2,000 acres of freshwater reservoirs and trout streams, with membership options that include a private Lake Club, tennis and pickleball courts, and a network of trails that winding through the preserve in every season. The property borders the 900 acre Toronto Reservoir, offering panoramic water views from the home itself. Minutes away you'll find the Eldred Preserve and its Homestead Restaurant for farm-to-table dining (with a large spa expansion coming soon), the Bethel Woods Center for the Arts, and the Monticello Motor Club. While homes within The Chapin Estate rarely change hands, and many are still held by their original owners, this is a unique opportunity to acquire a legacy property on the coveted Peninsula at a compelling price. Just two hours from Manhattan by car and fifteen minutes from the newly renovated Sullivan County International Airport, Whispering Oak Landing offers a rare seclusion that never feels remote.

51 Homestead Trail, White Lake

$3,595,000

4 Beds ⋅ 8 Baths ⋅ 1037747 MLS

Discover the Mayfly Inn at The Chapin Estate, an Adirondack-inspired lakefront sanctuary where rustic elegance meets refined leisure. Tucked within a private natural setting, this exceptional compound has been thoughtfully curated for those who value craftsmanship, comfort, and the timeless allure of waterfront living. From the moment you arrive, Mayfly Inn reveals itself in layers. Warm wood tones, lodge-style architecture, and bespoke details create an atmosphere that feels both elevated and effortless. The main living spaces are designed for gathering—grand yet inviting, with a natural flow that encourages conversation, connection, and quiet moments by the fire. Beyond the traditional bedrooms, the home offers additional bunkrooms and flexible recreational spaces, ideal for hosting extended family and accommodating guests with ease and sophistication. Curated furnishings ensure the home is ready to enjoy from the very first day. Exceptional features of this home include a full dog wash station, billiard's corner, full bar in lower den with lake view and a stone archway leading to an artfully designed wine cellar. Outdoors, the property is truly a private resort. An oversized connecting breezeway serves as a covered deck for outdoor dining and fireside chats. In the distance, a dock extends into the waters of the Toronto Reservoir, offering a front-row seat to sunrise paddles, afternoon swims, and evenings when the lake turns to glass. The grounds are enriched with thoughtful amenities, including a charming putting green perfect for leisurely practice or friendly competition. A 4-seater ATV makes navigating these 5 acres a breeze. Every corner of Mayfly Inn is designed to elevate the experience of being here—whether it’s a summer weekend filled with laughter, a crisp autumn escape, or a winter retreat where the world feels wonderfully still. This is more than a lake house; it’s a place where memories gather, traditions deepen, and the beauty of the Catskills becomes part of your everyday rhythm. Mayfly Inn invites you to live luxuriously while being connected to the water, the land, and the people that matter most. Located at the Chapin Estate, a 4-season gated residential preserve on 2,500 acres of pristine forest lands bordering 14,000 acres of forever wild conservation properties. Unique attributes include: 1,750 acres of freshwater lakes and trout streams; 9+ miles of hiking, biking and snowshoe trails; Members only Lake Club; Security patrolled and Concierge Services. Conveniently located less than 2 hours from Mid-Town Manhattan and even less from North Jersey.

60 Top Ridge Trail, White Lake

$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

$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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