Monticello Homes with Security Amenities

Monticello Homes with Security Amenities

Welcome to Monticello, New York, where the charm of small-town living meets the vibrancy of a community rich in culture and opportunity. Nestled in Sullivan County, Monticello is not just a picturesque town; it’s also home to a highly regarded school district that prioritizes academic excellence and holistic development. The Monticello Central School District offers a diverse curriculum and a range of extracurricular activities, ensuring that students are well-prepared for their future endeavors. With dedicated teachers and modern facilities, families can rest assured that their children will receive a quality education in a supportive environment.

In addition to its exceptional educational offerings, Monticello boasts a variety of homes equipped with state-of-the-art security amenities. Whether you’re a first-time homebuyer or looking to relocate, you’ll find properties that prioritize your safety and peace of mind. Many homes in the area feature advanced security systems, including surveillance cameras, smart locks, and alarm systems, allowing you to feel secure in your new abode.

Living in Monticello means enjoying a blend of tranquility and convenience, with easy access to outdoor recreational activities, local dining, and shopping. The community is known for its welcoming atmosphere, making it an ideal place to raise a family or enjoy a serene lifestyle.

Discover the perfect blend of quality education and secure living in Monticello, NY. Explore the available homes today and take the first step towards your new beginning in this delightful community!

Newest Monticello Homes with Security Amenities

$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
$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
$479,000
3 Beds ⋅ 3 Baths ⋅ 987303 MLS
Crisp mountain air, pristine lakes, spacious pools, and numerous activities await you at Emerald Green in the Sullivan County Catskills. Welcome home to 20 Bristol Circle, a charming colonial situated on a serene and spacious lot. The house is move-in ready and offers central heating and air conditioning, three bedrooms, two and a half bathrooms, a finished basement, and a two-car garage. Enjoy your morning coffee on the covered front porch, on the massive back deck, or in the Zen garden in the backyard. This house is situated on one of the nicest lots in Emerald Green, come see it today! Upon entering the foyer, you are greeted by double height ceilings and an airy interior. The first floor features a large, eat-in kitchen with ample cabinet space, an island breakfast bar, and a pantry closet. A slider in the kitchen leads to a massive deck which faces the woods, the perfect spot for grilling or entertaining. There is a formal dining room, a spacious living room with a propane fireplace, and a bonus den/family room that can be used as a home office or first floor guest room. This level has a half bathroom and coat closet in the foyer. The second floor has a spacious landing with a linen closet, a full bathroom with a bathtub, and three good-sized bedrooms. The primary bedroom is massive and offers cathedral ceilings, a walk-in closet, and an over-sized bathroom with a jacuzzi tub, walk-in shower, and double vanity. The finished basement offers another large and flexible space, which could be used as a playroom or home office, and it has a laundry area as well. The over-sized two-car garage can accommodate two large vehicles, as well as plenty of storage. It’s hard not to fall in love with the peaceful setting upon which the house is located. The front and rear yards are beautifully landscaped and offer plenty of space to enjoy. There are no houses behind this one, so the woods create a tranquil oasis with vibrant wildlife. There is a serene Zen garden in the backyard, a little slice of Catskill mountain paradise. The house is located right near the Entertanium, outdoor sports courts, dog run, and clubhouse. Emerald Green is Sullivan County’s premier private community. It offers two brand new pools that are located at the lakeside sand beach. There are three lakes for boating (non-gas boats only) fishing, and swimming. Boat slips are available for rent. There are also communal playgrounds, basketball courts, tennis courts, pickleball courts, a dog run, and an indoor clubhouse with a gym. Emerald Green offers community events such as holiday celebrations, seasonal fireworks, activities for all ages, exercise classes, game nights, etc. It is the perfect way to experience the quiet of country living in a friendly and serene neighborhood setting. This property offers the benefits of municipal water and sewer, as well as road maintenance and snowplowing provided by the town. Rock Hill is the perfect place for a country getaway or full-time home. With its small-town charm, convenient shopping options and proximity to the city, this is the place to be in Sullivan County!

20 Bristol Circle, 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
$589,000
3 Beds ⋅ 2 Baths ⋅ 986218 MLS
Beautiful Renovated Lake House with Prime Lakefront Location on Treasure Lake & Community Amenities located in Emerald Green. This is great for all year round living or for your weekend gateway! Enjoy the areas amenities such as Resort's Casino, Water Park, Monster golf course Restaurants and many local breweries and fishing lakes and even skiing for the winter! Experience lakeside living at its finest in this beautifully renovated lake house, perfectly situated on serene lake frontage. This charming home offers a modern, updated interior done in 2025 with spacious living areas, stylish finishes, and breathtaking waterfront views. Enjoy direct access to the lake for swimming, kayaking, or fishing right from your backyard. The community features a range of amenities, including a private dock, swimming pool, clubhouse, walking trails, and recreational areas—ideal for relaxing weekends or active outdoor lifestyles. There wasn't a room that hasn't been touched in this home. The basement is fully finished and ready to entertain guests. Whether you're seeking a peaceful retreat or a fun-filled getaway, this lake house combines comfort, convenience, and natural beauty in a sought-after community setting.

119 Lake Shore Drive W, Rock Hill
$750,000
4 Beds ⋅ 2 Baths ⋅ 983942 MLS
Experience lakefront living at its finest in this beautifully maintained 4 bedroom, 2 bath contemporary lakefronthome located in a premier 1,400 acre community featuring three private lakes, Lake Louise Marie, Treasure Lake, and Davis Lake, with more than 250 acres of pristine water for swimming, fishing, and electric boating. Designed to showcase breathtaking lake views, the main level features soaring cathedral ceilings and dramatic floor to ceiling windows and glass sliders that flood the home with natural light while providing panoramic waterfront views from the living room, dining area, and kitchen. The spacious living room is anchored by a stunning floor to ceiling stone fireplace with a ceramic sterno insert and accented by skylights and an elegant Murano glass chandelier. Hardwood floors and central air complete the home’s comfortable and inviting interior. The kitchen features a convenient serving bar that opens seamlessly to the dining area, creating an ideal space for entertaining. Glass sliders lead to an expansive full length Trex deck with two electric awnings, providing the perfect setting for outdoor dining, relaxing, and taking in spectacular sunsets over the lake. The main level includes a spacious primary bedroom, a second bedroom, and a beautifully renovated full bath with tasteful designer finishes. The finished walkout lower level offers a large family room, two additional bedrooms, a full bath, and a utility room, providing flexible space for guests, extended family, or recreation. Outside, enjoy your own private waterfront retreat featuring a professionally landscaped lawn, illuminated cobblestone walkway, an oversized Trex deck, private sandy beach, gazebo, and private dock, ideal for a pontoon boat, kayaking, paddleboarding, fishing, or simply enjoying life on the water. A horseshoe driveway accommodates 6 to 8 vehicles, while the home’s attractive wood and cultured stone exterior adds timeless curb appeal. Residents enjoy an outstanding array of resort style amenities including an Olympic size adult pool with lap lanes and a current walking lane, a children’s pool with splash features, sandy beaches, a fitness center, tennis and pickleball courts, basketball courts, playgrounds, a dog park, and year round social activities including yoga, aqua aerobics, book clubs, potlucks, and live entertainment. Conveniently located just minutes from Bethel Woods Center for the Arts, Resorts World Catskills, The Kartrite Resort and Indoor Waterpark, Holiday Mountain Ski and Fun Park, local wineries, scenic hiking trails, farmers markets, and countless outdoor recreational opportunities, this exceptional lakefront home offers the perfect combination of luxury, comfort, privacy, and an unmatched four season lifestyle.

44 Lake Shore Drive S, Rock Hill
$3,475,000
5 Beds ⋅ 6 Baths ⋅ 967444 MLS
A mere two hours from New York City, The Top Ridge Retreat offers a rare combination of modern elegance, natural beauty, and complete privacy within the exclusive 2,500-acre gated community of The Chapin Estate. Set on more than eleven acres, this contemporary residence delivers a refined lifestyle designed for comfort, sophistication, and seamless indoor-outdoor living. Inside, the layout balances openness with intimacy. The home is offered fully furnished, with carefully curated furniture and artwork included to complement its contemporary design and elevate the overall living experience. The primary suite includes a private sitting area, fireplace, and spa-like bath, creating a true sanctuary. Additional bedrooms are spacious and well-appointed for guests. A sunken living room and library—each with a fireplace—add warmth and architectural interest, while a dedicated gym, massage room, and wellness area enhance the home’s retreat-like atmosphere. Every element of the home has been thoughtfully crafted. With 205 oversized windows, natural light fills each space and creates a continuous connection to the surrounding forest. The expansive chef’s kitchen and dining room overlook the saltwater Gunite pool, pool house, and a fully equipped indoor/outdoor kitchen featuring a fireplace, pizza oven, and dining gazebo—an ideal setting for effortless entertaining. A short stroll from the pool leads to a world-class tennis court with its own cabana, offering resort-level recreation right at home. The residence is built with uncompromising attention to quality. Features include a 12-zone radiant and solar heating system, a 12-ton central air conditioning system, custom cabinetry, and bespoke tile work throughout. From the solid wood doors to the precision-crafted finishes, every detail reflects a commitment to excellence. Life within The Chapin Estate offers unmatched access to nature and amenities. The community spans more than 2,500 acres of pristine forest and borders an additional 14,000 acres of protected conservation land. Residents enjoy miles of hiking, biking, and snowshoe trails; freshwater reservoirs and trout streams; concierge services; security patrols; and a members-only Lake Club. From within the community, owners have direct access to both Toronto Reservoir and Swinging Bridge Reservoir, ideal for boating, kayaking, fishing, and quiet days on the water. Just one mile away, the Chatwal Lodge provides elevated dining and hospitality. Located in the hamlet of White Lake, part of historic Bethel—home of the 1969 Woodstock concert—this region is rich with culture and recreation. The Bethel Woods Center for the Arts offers world-class performances and a renowned museum. Nearby, the Monticello Motor Club provides a premier private automotive experience. Farm-to-table dining, boutique cafés, craft breweries, lake activities, skiing, and endless outdoor adventures complete the lifestyle. A true escape from city life, The Top Ridge Retreat delivers privacy, beauty, and resort-style amenities in one of Sullivan County’s most coveted luxury communities. This is contemporary living at its finest—without the stress of the Long Island Expressway.

61 Top Ridge 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
$64,999
2 Beds ⋅ 2 Baths ⋅ 944437 MLS
Welcome to a fantastic opportunity in the sought-after Kinnebrook Community. This 2-bedroom, 1.5-bath home is priced to sell! The home features a functional layout awaiting your personal touch. Enjoy a hassle-free lifestyle with community-provided water, septic, snow, and trash removal, as well as fantastic amenities including an in-ground pool and a dog park. With low lot rent and a motivated seller, this property, sold AS-IS, won't last long. Schedule your showing today!

25 Pansy Lane, Monticello
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