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$1,250,000

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.

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

$115,000

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.

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

$550,000

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.

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