Monticello Homes with Maintenance Amenities

Welcome to Monticello, NY – a charming town nestled in the heart of Sullivan County, where vibrant community spirit meets the tranquility of nature. Known for its rich history and stunning landscapes, Monticello is not just a picturesque place to live, but also home to an exceptional school district that prioritizes educational excellence.

The Monticello Central School District is dedicated to fostering a nurturing environment for students, offering a diverse curriculum that caters to various learning styles. With a commitment to academic achievement, the district boasts innovative programs in the arts, technology, and athletics, ensuring that every child has the opportunity to thrive. Parents will appreciate the dedicated staff and small class sizes that allow for personalized attention, helping students reach their full potential.

In addition to its educational offerings, Monticello presents a selection of homes with maintenance amenities designed for a hassle-free lifestyle. These residences often feature landscaping services, snow removal, and other conveniences that allow homeowners to enjoy their surroundings without the burden of upkeep. Imagine coming home to a beautifully maintained property, where you can relax and unwind after a busy day, all while knowing that your investment is well taken care of.

Whether you’re seeking a family-friendly environment or a peaceful retreat, Monticello offers the perfect blend of community and comfort. Discover the joys of living in a town that values education and convenience, making it an ideal place to call home. Experience the charm of Monticello, where your dream home awaits!

Newest Monticello Homes with Maintenance 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

$389,000

2 Beds ⋅ 3 Baths ⋅ 1020730 MLS

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

2 Sylvia Lane, Monticello

$499,990

2 Beds ⋅ 2 Baths ⋅ 999731 MLS

Set directly on the shores of Treasure Lake within the highly sought-after Emerald Green community, this beautifully reimagined waterfront retreat offers approximately 100 feet of lake frontage and breathtaking sunset views looking west across the water. Nestled within a premier 1,400-acre private community featuring Lake Louise Marie, Treasure Lake, and Davis Lake, residents enjoy access to over 250 acres of water ideal for swimming, fishing, kayaking, paddleboarding, and electric boating. Completely renovated down to the studs, this move-in-ready home was thoughtfully designed to capture its incredible lakefront setting. The open-concept main living area is highlighted by dramatic floor-to-ceiling windows that flood the home with natural light while showcasing panoramic lake views from nearly every angle. A wood-burning fireplace adds warmth and charm, while sliding glass doors lead to an expansive deck and screened-in porch — the perfect places to relax and take in the spectacular evening sunsets over Treasure Lake. The updated kitchen features stone countertops and stainless steel appliances, seamlessly connecting to the dining and living spaces for effortless entertaining. The home offers two generously sized bedrooms, including a private primary suite with its own full bath, plus an additional full bathroom and convenient laundry area. Individual heating zones throughout the home provide comfort and efficiency, complemented by a newer ductless heating and cooling system. Beneath the home, a spacious crawlspace offers ideal storage for kayaks, paddleboards, floats, life jackets, and all your waterfront gear. Outside, the level backyard leads directly to the lake and creates the ultimate outdoor setting with a private dock, sandy beach area, firepit, and endless opportunities to enjoy the waterfront lifestyle. Emerald Green residents enjoy an impressive collection of amenities including indoor and outdoor pools, fitness center, indoor walking track, tennis and pickleball courts, basketball courts, dog park, clubhouse, sandy beach, and a vibrant social calendar featuring live entertainment, community gatherings, fitness classes, fireworks, and more. Conveniently located near destinations like Bethel Woods Center for the Arts, Resorts World Catskills, and The Kartrite Resort & Indoor Waterpark, along with skiing, hiking trails, wineries, and countless outdoor attractions, this is a rare opportunity to own a fully updated lakefront home with stunning western sunset exposure in one of the region’s most desirable private lake communities.

117 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

$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

$429,000

2 Beds ⋅ 2 Baths ⋅ 979575 MLS

Some homes are where you live. Others are where you finally exhale. Set along the peaceful shoreline of Forestburgh Pond, this two-bedroom, two-bathroom waterfront cabin offers something that's becoming increasingly difficult to find: privacy, water access, and a slower pace of life just 90 minutes from New York City. Whether you're searching for a full-time residence, a weekend retreat, or a property with short-term rental potential, this home is designed to make every season feel like a getaway. The open living space welcomes you with vaulted ceilings, a floor-to-ceiling stone fireplace, warm hardwood floors, and oversized windows that keep the water in view. The kitchen blends style and function with quartz countertops, stainless steel appliances, open shelving, and a cozy dining area overlooking the pond. The primary bedroom features its own updated en suite bathroom with a walk-in shower, while the second bedroom and additional full bath provide comfortable space for guests. Outside is where this property truly shines. Launch a kayak from your own shoreline, spend the afternoon fishing or canoeing, unwind around the fire pit beneath the stars, or simply enjoy the peaceful views from the wraparound deck. Every part of the property invites you to slow down and enjoy the setting. Beyond the water, you'll appreciate being just minutes from local favorites including the Forestburgh Tavern, Forestburgh Playhouse, scenic walking trails, Bethel Woods Center for the Arts, and charming local shops. It's a location that feels tucked away while still keeping some of Sullivan County's best destinations close by. If you've been waiting for a waterfront property that offers both everyday comfort and the kind of lifestyle people travel to experience, this is one worth seeing.

10 Stag Forest Road, Forestburgh

$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

$600,000

903323 MLS

This gorgeous home site has a most dramatic elevation change on over 5+ acres with build site facing the northern mountain range. This lot consists of lush forests full of evergreens and hardwoods. The improved gravel driveway leads to the elevated home site and then to 336’ of frontage on the shores of the Swinging Bridge Reservoir. The opposite shoreline has building restrictions which limit the private residents to building 300' from their shoreline. This essentially offers forever wild views from this property and it's shoreline. 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. 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. Conveniently located less than 2 hours from Mid-Town Manhattan and even less from North Jersey. Building your dream home: bring your own builder or use a reputable builder that is familiar with the guidelines in the community. The 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 Homesite With Forever Wild Views at The Chapin Estate, Lumberland, New York 12737, this Land is for Sale with a price of $600,000. This listing encompasses a lot of 5.67 Acre(s). See all Homes for Sale in Lumberland.

Lot 1 Woodstone Trail, Lumberland

$550,000

903318 MLS

This beautiful lot is on the water with a quiet cove for privacy. This property also features a small fishing pond with a natural spring-fed stream running close to the homesite. The lot is one of the widest available properties on the Swinging Bridge Reservoir with 535' of frontage. Hardwood and pine forests are thick and lush for a natural barrier between you and the neighboring homes. The water activities include waterskiing, kayaking, paddle boarding, fishing, canoeing and sailing. This lot is a short drive to our member’s only lake club. 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 and Security patrolled. Conveniently located less than 2 hours from Mid-Town Manhattan and even less from North Jersey. Building your dream home: bring your own builder or use a reputable builder that is familiar with the guidelines in the community. The 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.

Lot 23 Woodstone Trail, White Lake

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