$1,295,000

AN EXCEPTIONAL 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… Read More 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. Read Less

Listing Courtesy of Boller Properties.

Listing Snapshot

Days Online

Last Updated

Aug 30, 2026

Property Type

Single Family Residence

Beds

Full Baths

Partial Baths

Square Ft.

3,800

Year Built

2003

Property Tax

$25,632

MLS Number

1034443

30 Days Snapshot Of 12786

$372k

(avg) sold price

-100%

homes sold

144

(avg) days on market

Snapshot

Area Map

Additional Details

Appliances & Equipment

Description: Dishwasher, Exhaust Fan, Gas Range, Microwave, Oven, Stainless Steel Appliance(s), Gas Water Heater

Building

Area: 3800, Architecture: Chalet, Contemporary, Craftsman, Construction Materials: Stone, Wood Siding, Levels: Tri-Level, Year Built: 2003

Cooling

Details: Central Air

Exterior Features

Features: Awning(s), Balcony, Dock, Fire Pit, Gas Grill, Juliet Balcony, Lighting, Speakers, Patio Features: Deck

Fireplaces

Total Fireplaces: 1

Floors

Flooring: Carpet, Concrete, Hardwood, Wood

Garage

Garage Spaces: 2

Heating

Heating: Forced Air, Propane

Home Owner's Association

Dues Frequency: Monthly, Fee: 167, Description: Common Area Maintenance, Grounds Care, Snow Removal

Laundry

Description: Laundry Room

Lot

Features: Back Yard, Cul-De-Sac, Garden, Landscaped, Level, Near Golf Course, Near Public Transit, Near School, Near Shops, Part Wooded, Private, Secluded, Views, Waterfront, Wooded, Acres: 5.04

Utilities

Sewer: Septic Tank, Water Source: Well, Utilities: Cable Connected, Electricity Connected, Phone Connected, Sewer Connected, Trash Collection Private, Underground Utilities, Water Connected

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