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

$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

$1,050,000

4 Beds ⋅ 3 Baths ⋅ 1017659 MLS

LAKEFRONT TURN-KEY RETREAT ON 5.08 ACRES – BLACK LAKE ESTATES Welcome to 25 Water's Edge Dr, a meticulously reimagined 4-bedroom, 3-bath lakefront home in the gated community of Black Lake Estates. Nestled on 5.08 private acres with deeded dock rights on Big Black Lake, this 2,530 sq ft gem blends rustic charm with premium modern finishes throughout. MAIN LEVEL: A mud room welcomes you from the entry with lake views, flowing into an open-concept living space with vaulted ceilings, ceiling fans, and a stunning wall of glass overlooking the lake. The living room features a brick fireplace, and ceramic wood tile floors with sliders opening to a wrap-around deck — perfect for morning coffee or evening entertaining. CHEF'S KITCHEN: Completely remodeled with Bosch appliance package, butcher block countertops, and a custom copper farm sink — the heart of the home is as functional as it is beautiful. Two main-level bedrooms and a full double vanity bath complete this floor. UPPER LEVEL PRIVATE SUITE: A true retreat. The primary bedroom features a full ensuite bath, plus your own private loft space — ideal as a home office, studio, or reading nook, all with sweeping lake views. The loft overlooks the living room below, adding an airy, open feel. LOWER LEVEL – FINISHED WALKOUT: Radiant heat throughout. The entertainment area opens via slider to the yard and lake. A unique kids bunk room sleeps four with built-in bunks. The spa-like full bath features a steam shower. Separate laundry room and utility room with oil tank furnace, water softener, and HVAC unit. OUTDOORS: Professional landscaping surrounds the property. An outbuilding provides equipment storage. Hammocks perfect for snoozing! A private dock on Big Black Lake awaits your canoe, kayak, or paddleboard. Low HOA of just $1,100/year. EXTRA $: Whole-house propane generator | Water softener system | Radiant heat on lower level| Black Lake Estates gated community | Just minutes to Bethel Woods, shopping, dining, and all the Catskills have to offer. Delight in this move-in ready year-round retreat! 2 hrs to NYC. Call for an appointment today!

25 Waters Edge Drive, 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

$695,000

6 Beds ⋅ 3 Baths ⋅ 1005435 MLS

Perched on the eastern end of Treasure Lake, this spacious 6 bedroom lakefront 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

$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

$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

$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

$140,000

923105 MLS

Build Your Dream Home on 8.89 Private Acres in Black Lake Estates Nestled within the exclusive gated community of Black Lake Estates in Bethel, NY, this expansive 8.89-acre homesite offers a rare opportunity to create your private escape in a peaceful, natural setting. This gently wooded parcel offers privacy, tranquility, and direct access to Little Black Lake, which connects seamlessly to the stunning 250-acre Big Black Lake, perfect for boating and waterside relaxation. The land is level and build-ready, featuring a dock for easy water access, a rough timber shed, picnic table, and partially cleared areas for ease of development. The property is also graced with beautiful natural stone walls that add timeless character and rustic charm to the landscape. A driveway has already been cut providing a head start for your custom home plans. Black Lake Estates is known for its serene atmosphere, abundant wildlife, and large lot sizes. Residents enjoy access to a private beach, community caretaker, and motorboat-friendly waters. Little Black Lake offers a more secluded, intimate waterfront experience while still connecting to the larger lake for extended adventures. Surrounding lands include protected NYS forest, ensuring long-term peace and unspoiled views. Whether you're into kayaking, paddle boarding, or simply stargazing under the clear Catskills skies, this is the perfect place to recharge. Located minutes from Bethel Woods Center for the Arts, waterfront dining, craft breweries, hiking trails, skiing, casinos, and more—yet you'll feel a world away from it all. Additional Highlights: Private gated lake community with a yearly association fee of $1,100 Motorboat access to Big Black Lake Dock, shed, picnic table, and natural stone walls included Soil type: Unknown Abundant mature trees and natural landscape Close to Catskills attractions and outdoor recreation Don’t miss this chance to create your own sanctuary in one of Sullivan County’s most coveted lake communities.

Lot 4 Deer Meadow Road, White Lake

$625,000

903335 MLS

This stunning home site, adjacent to Lot 1, consists of lush forests full of evergreens and hardwoods. However, the change in elevation allows for 2 home sites. The first site is close to the 413’ of Lake Frontage that is facing north to the mountains and surrounded by mature trees. The second site, much higher, allows for longer views with a gravel driveway to the water below. An old carriage trail runs along the shoreline here and there is a high cliff on one end of the lot and a more gradual access on the other for access to Swinging Bridge Reservoir. Located at the Chapin Estate, a 4-season gated residential preserve on 2500 acres of pristine forest lands bordering 14,000 acres of forever wild conservation properties. Unique attributes include: 1,750 acres of fresh water lakes and trout streams; 9+ miles of hiking, biking and snow shoe trails; Members only Lake Club; Security patrolled and Concierge Services. Also located within our gates is The Chatwal Lodge - a wonderful amenity for the residents and guests. Book a weekend to see what the Chapin lifestyle has to offer. Conveniently located less than 2 hours from Mid-Town Manhattan and even less from North Jersey. Bring your own builder or use on of the recommended craftsmen from our area. Nestled in the heart of the Catskills, Sullivan County offers a rare blend of natural grandeur and cultural sophistication. Known for its pristine lakes, protected forests, and sweeping mountain vistas, the region is a sanctuary for those seeking tranquility without sacrificing access to world-class amenities. From the storied banks of the Delaware River to the exclusive enclaves of The Chapin Estate, Sullivan County is home to some of New York’s most coveted private retreats. Residents enjoy four-season recreation—kayaking, hiking, fly fishing, and snowshoeing—alongside curated experiences like concerts at Bethel Woods Center for the Arts, farm-to-table dining, and boutique shopping in towns like Narrowsburg and Callicoon. With its proximity to Manhattan and North Jersey, Sullivan County offers effortless escape and enduring value. Whether you're seeking a legacy estate, a waterfront haven, or a modern mountain lodge, this region invites you to live beautifully, surrounded by nature and steeped in possibility. Located at Captivating lake front view at the Chapin Estate, Lumberland, New York 12737, this Land is for Sale with a price of $625,000. This listing encompasses a lot of 5.65 Acre(s). See all Homes for Sale in Lumberland.

Lot 2 Woodstone Trail, Lumberland

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