Monticello Homes with Gated Amenities

Welcome to Monticello, New York, a charming village nestled in the heart of Sullivan County. Known for its picturesque landscapes and vibrant community, Monticello offers a unique blend of small-town charm and modern conveniences. One of the standout features of this area is its highly regarded school district, which is committed to providing quality education and fostering a nurturing environment for students. Monticello Central School District is dedicated to academic excellence, offering a variety of programs and extracurricular activities designed to engage students and prepare them for future success.

Families looking to settle in Monticello will be pleased to discover an array of homes with gated amenities, ensuring both security and a sense of community. These gated properties not only offer peace of mind but also provide a luxurious lifestyle with access to beautiful landscapes and well-maintained common areas. Imagine enjoying your morning coffee surrounded by serene nature or hosting gatherings in your spacious backyard, all within the safety of a gated community.

In addition to the excellent schools, Monticello boasts a rich history and a variety of recreational opportunities. From nearby hiking trails to local parks and vibrant community events, there’s always something to do. Whether you’re a first-time homebuyer or looking to upgrade your living situation, Monticello’s combination of quality education, gated homes, and community spirit makes it an ideal place to call home. Discover the charm of Monticello and let this vibrant village welcome you into its warm embrace!

Newest Monticello Homes with Gated 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

$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

$99,900

1043615 MLS

Experience the quiet elegance of country living in the private, gated lake community of Black Lake Estates. The community’s main attraction is Black Lake, the pristine 250-acre non-motorboat lake. This gorgeous lake offers exceptional fishing, kayaking, canoeing, and peaceful boating reserved exclusively for property owners. Tucked away at the end of a quiet dead-end road, this beautiful homesite overlooks a tranquil natural pond, creating a private woodland retreat. Surrounded by towering trees, lush ferns, blooming mountain laurel, and moss-covered boulders, the landscape is rich with natural beauty. Deer, wild turkey, rabbits, and a variety of waterfowl are frequent visitors, making this a truly enchanting setting for your future home. Ideally located just 90 miles from New York City, you're also minutes from hiking trails, excellent restaurants, Bethel Woods Center for the Arts, Resorts World Catskills Casino, the exclusive Monticello Motor Club, and everything the Sullivan Catskills has to offer. Whether you're envisioning a weekend escape or a full-time residence, this is a rare opportunity to own a piece of one of the area's most desirable private lake communities.

Lot 23 Deer Meadow Road, Bethel

$1,299,900

4 Beds ⋅ 2 Baths ⋅ 1041178 MLS

Black Lake Cedar contemporary offers a rare combination of pristine waterfront, complete privacy, and direct access to hundreds of acres of protected New York State land. This meticulously maintained 4-bedroom, 2-bath lakefront home enjoys breathtaking panoramic views and an unmatched natural setting that will remain forever preserved. The warm, inviting interior features rich cedar accents throughout, creating the perfect Adirondack-inspired retreat. A spacious open great room is framed by dramatic floor-to-ceiling windows that fill the home with natural light while showcasing the spectacular lake views. Step outside to the expansive, private deck or relax in the screened porch, where you can enjoy the sights and sounds of nature in every season. The full walk-out basement offers exceptional custom storage, built-in workbenches, and an oversized one-car garage. A paved driveway leads directly to the waterfront, complete with electric lighting for easy evening access. At the shoreline, you'll find a cantilever dock and electricity at the water's edge - perfect for charging your electric watercraft and enjoying effortless days on the lake. Bordering Lake Superior State Park, the property benefits from permanently protected land, ensuring unobstructed views and exceptional privacy for generations to come. Spend your days hiking, picking wild blueberries, swimming, boating, or fishing on one of the area's most beautiful lakes. Lovingly enjoyed by the same owners for 46 years and impeccably maintained since the home was built 30 years ago, this exceptional property is truly move-in ready. Whether you're seeking a year-round residence or a cherished lakeside getaway, this is a place where memories will be made for years to come. Near to Bethel Woods for world-class entertainment, fantastic restaurants, farmers’ markets, motorboat lakes and all the wonderful things the Sullivan County Catskills has to offer!

74 Oxford Drive, 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

$695,000

6 Beds ⋅ 3 Baths ⋅ 1034438 MLS

Occupying the eastern point of Treasure Lake, facing due west, this spacious 6 bedroom duplex boasts the most magnificent sunsets in the Catskills, cascading behind a scenic island, mirroring water and sky. Designed and built by a builder as his personal home, this sturdy retreat features an intuitive interior and elevated exterior landscape rarely found in lakefront homes. Built in 2009, This comfortable home offers year-round lakefront living with plenty of room to spread out, entertain, and take in the views. Upon entering the foyer, the home opens into two living levels with three bedrooms on the ground level, and three upstairs. A vaulted great room with dramatic ceiling height features a propane fireplace, built in entertainment center, and wide picture windows framing the lake. The open kitchen features granite countertops, a large center island, stainless refrigerator, and sliding glass doors leading to a covered deck, perfect for outdoor grilling & dining, lounging, and watching the light dance across the water. An additional indoor sitting room can easily convert into a formal dining room. A gallery hallway leads to a spacious primary suite, two sumptuous bedrooms and a recently updated hallway bathroom. Spreading behind its double doors, the primary suite spans the entire northern wing of the upper level. The bedroom itself offers vaulted ceilings and peaceful lake views, leading seamlessly into a generous windowed en-suite bath with a whirlpool soaking tub, standing shower, and dual sinks. Beyond the bath, the suite expands into a large formal dressing room and a sun-filled lake-facing bonus room, accessible through French doors, and can function beautifully as a private sitting room, office, nursery, or additional bedroom. The lower level offers an additional living zone with three more bedrooms, a third full bath, a second propane fireplace, and a walk-out family room with a second expansive deck, a perfect level for guests, multi-generational living, or a dedicated recreation floor. Additional interior features of the home include central heat and air conditioning, an oversized 2-car garage, and double entry door. Exterior highlights include a paved circular driveway, leveled lawns leading to the shoreline, a high-yielding vegetable garden with imported soil, and a garden shed. An adjacent vacant lot is also available for sale, ideal for privacy, future expansion, or an additional homesite. Affectionately considered the crown jewel of the Catskills, Emerald Green is a desirable lake community comprised of three pristine mountain lakes. World class amenities include a newly installed olympic-size pool, splash pool, beach, marina, tennis, pickleball, basketball, fitness center, clubhouse, dog park, and year-round events. Dues are $850/year plus a temporary $725/year assessment for newly upgraded facilities. Dock slips are available at the marina for pontoon boat owners. Short-term rentals are not permitted, and long-term rentals are allowed only after two years of ownership. Centrally located near Rock Hill and Monticello, the region offers a diverse selection of shopping and dining, healthcare facilities, the Bethel Woods performing arts center, Kartrite waterpark, Resorts World casino, a championship golf course, breweries, and charming towns such as Narrowsburg and Livingston Manor. Minutes from a grocery store and acclaimed dining such as Cellio Steakhouse, Lotus, and Dos Gatos. Other nearby attractions include the Monticello Motor Club (currently developing a boutique hotel), the Eldred Preserve (resort and wedding venue), and the premium Chatwal Lodge at the Chapin Estate. Just 90 minutes from Manhattan by car, this home offers the perfect blend of year-round living, weekend escape energy, and lakefront serenity, cradled within one of the Catskills’ most amenity-rich communities.

61 Lake Shore Drive W, Rock Hill

$825,000

3 Beds ⋅ 3 Baths ⋅ 1031460 MLS

Verdant Forest Hideaway- Paradise awaits at 111 Deer Meadow Road; a private woodland retreat nestled within the prestigious gated community of Black Lake Estates. Tucked beneath a canopy of mature trees and surrounded by gently meandering streams, this exceptional contemporary home is perfectly positioned on 5.02 secluded acres, offering a rare combination of luxury, tranquility, and natural beauty. Spanning 2,765 square feet, this thoughtfully designed residence features three spacious bedrooms and three full bathrooms, blending modern comforts with a peaceful, nature-inspired setting. Recent renovations include a beautifully updated chef's kitchen and tastefully remodeled bathrooms, while central air conditioning and a whole-house generator provide year-round comfort and peace of mind. The inviting floor plan offers generous living spaces filled with natural light and picturesque views of the surrounding forest. Whether you're entertaining guests or enjoying a quiet evening at home, every room has been designed to embrace the property's serene setting. The finished basement adds valuable flexible space, perfect for a recreation room, home office, fitness area, media room, or guest accommodations. Step outside and immerse yourself in your own private sanctuary, where the soothing sounds of flowing streams and abundant wildlife create an atmosphere of complete tranquility. Beyond the property, residents of Black Lake Estates enjoy exclusive access to Black Lake, a pristine, approximately 225-acre private lake ideal for swimming, fishing, kayaking, canoeing, paddleboarding, and other non-motorized boating activities. Whether you're spending the day on the water or relaxing along the shoreline, the lake offers an exceptional outdoor lifestyle in a peaceful natural setting. While the home feels wonderfully secluded, it is just a short drive from many of the Catskills' most sought-after destinations, including Lake Superior State Park, Bethel Woods Center for the Arts, White Lake, Resorts World Catskills Casino, and The Kartrite Resort & Indoor Waterpark. This remarkable property offers the perfect balance of privacy, recreation, and convenience, making it an ideal year-round residence or luxurious weekend retreat.

111 Deer Meadow Road, White Lake

$175,000

1028197 MLS

Discover the perfect setting for your dream home on this beautiful 10.65+/- acre parcel featuring frontage on Wesserlauf Pond, with land extending on both sides of the pond for a truly unique and private setting. Mostly cleared and level, this property is ready for your custom home, weekend retreat, or peaceful country escape. Enjoy lake rights to Black Lake, a tranquil 250 acre non-motorboat lake ideal for kayaking, canoeing, fishing and relaxing in nature. Conveniently located near shopping, dining, and the renowned Bethel Woods Center for the Arts, you'll have the perfect balance of serenity and accessibility. Best of all, you're just two hours from NYC, making this an ideal getaway or year-round residence. Build your vision in the Sullivan County Catskills, where natural beauty, recreation, and convenience come together.

Lot 33 Black Lake Road, White Lake

$115,000

1021388 MLS

This gorgeous stream-front lot is located just inside the main gate of The Chapin Estate. The lot borders 448 feet of 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, and you have access nearby on Moscoe Road. This is a 4 season, gated, residential community that consists of 2500 acres of preserved lands that border 1750 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 for this particular homesite. Access to Swinging Bridge is also available within the community. As a resident, you may also rent a slip at the Lake Club to grant you access to both reservoirs. *Short term rentals are not permitted. Rental minimum of 3 months no more than twice per year. Confirmed appointment for the security of our residents.

TBD Chapin Trail, White Lake

$115,000

966241 MLS

Here is surely the best opportunity to build your dream home on 5.26 private acres within the elegant sanctuary of Chapin Estates — a premier gated residential preserve celebrated for some of the East Coast’s most breathtaking natural beauty. Residents enjoy exceptional amenities, including a private lake club, sparkling lakes, trout streams, fishing, and miles of scenic hiking trails. Imagine yourself surrounded by distinguished estates valued from $1 million to over $10 million. This property offers an exclusive lifestyle in a peaceful yet convenient location. The Chatwal Lodge is also located within the community, adding an extraordinary touch of hospitality close to home. Not sure where to begin? This engineered lot is offered with custom house plans designed by Chapin Estates founder Steve Dubrovsky. For $844,900, Steve and his team are prepared to build the lodge depicted in the plans, creating a seamless path from vision to completion. Call today for more details and experience the luxury and serenity of living at The Chapin Estate.

Lot 32 Woodstone Trail, Bethel

$949,900

3 Beds ⋅ 3 Baths ⋅ 954068 MLS

*New Construction Let us bring your vision to life—your home, your way. Nestled within the prestigious Swinging Bridge section of Chapin Estates, this exceptional property offers a rare blend of rustic elegance and refined luxury. Located just two hours from New York City and minutes from Bethel Woods Center for the Arts, Resorts World Catskills, the Kartrite Indoor Waterpark and Award-winning golf courses, the homesite is ideally positioned for both serenity and adventure. The 5.28-acre parcel of ready-to-build land offers the perfect canvas for your dream home. A beautiful rock-lined driveway has already been cut in, welcoming you to your future retreat. We proudly offer the construction of a beautifully designed three-bedroom, two and a half -bath residence, tailored to meet your lifestyle and preferences. Whether you choose a fully custom design tailored to your vision or select from our curated collection of beautiful layouts. Each home reflects quality craftsmanship and timeless style, designed to harmonize with the natural surroundings and community aesthetic. Please note: All building plans must be approved by The Chapin Estates Association and must adhere to the community’s architectural guidelines. Images featured are sourced from America's Best House Plans and are used for inspiration purposes only. Residents and guests enjoy year-round access to the renowned Chatwal Lodge, a five-star wilderness retreat offering farm-to-table dining, spa and wellness experiences, and curated outdoor activities like fly fishing, boating, and guided nature walks. The community features private lake access, a members-only marina and clubhouse, and gated security for peace of mind. Recreational amenities include a swimming pool, tennis courts, pickleball and basketball courts, and miles of scenic walking trails. All walking distance from the property. Whether you're seeking a weekend escape or a full-time residence, this property delivers an unparalleled lifestyle defined by luxury, privacy, and natural beauty. On your way, enjoy a stop at Woodbury Commons for some great shopping or LEGOLAND New York and spend more quality time with the family. With its prime location, four-season appeal, and access to world-class amenities, this is more than a property—it’s a legacy in the making.

39 Woodstone Trail, Bethel

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