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$1,250,000
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Property Description
PRICE DROP! A MAGNIFICENT LEGACY INVESTMENT, ON THE PENINSULA OF THE CHAPIN ESTATE. One of a kind, by its very nature. An incomparable trophy property 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-built, one owner 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.
Full Property Details
Full Property Details for 51 Homestead Trail
General
- Price: $1,250,000
- HOA FEE: $167/month
- Taxes: $25,632
- Status: Active
- Type: Single Family
- Source: Long_Island
- MLS ID: 1034443
- Updated: 9/21/2026
- Added to Site: 45 day(s) ago
Interior
- Number of Rooms: 10
- Interior Features: First Floor Bedroom, First Floor Full Bath, Beamed Ceilings, Built-in Features, Cathedral Ceiling(s), Ceiling Fan(s), Chandelier, Double Vanity, Eat-in Kitchen, Entrance Foyer, High Ceilings, High Speed Internet, Kitchen Island, Natural Woodwork, Open Floorplan, Open Kitchen, Original Details, Primary Bathroom, Recessed Lighting, Sauna, Soaking Tub, Speakers, Walk-In Closet(s), Wired for Sound
- Fireplace: Yes
- Number of Fireplaces: 1
- Fireplace(s): Wood Burning
- Appliances: Dishwasher, Exhaust Fan, Gas Range, Microwave, Oven, Stainless Steel Appliance(s), Gas Water Heater
- Laundry Facilities: Yes
- Flooring: Carpet, Concrete, Hardwood, Wood
Rooms
Bathrooms
- Total Bathrooms: 4
- Full Bathrooms: 3
- Half Bathrooms: 1
Bedrooms
- Total Bedrooms: 4
Other Rooms
- Laundry: Laundry Room
Additional Information
- Shared Amenities: Boat Dock, Clubhouse, Gated, Landscaping, Maintenance, Maintenance Grounds, Pool, Powered Boats Allowed, Recreation Facilities, Sauna, Security, Snow Removal
- Security/Safety: Gated Community, Security Gate, Security Lights, Security System, Smoke Detector(s)
Exterior
- Exterior Features: Awning(s), Balcony, Dock, Fire Pit, Gas Grill, Juliet Balcony, Lighting, Speakers
- Porch/Patio/Deck: Deck
Parking
- Garage: Yes
- Garage Spaces: 2
- Parking Features: Garage, Garage Door Opener
Location
- County: Sullivan County
- Subdivision: The Chapin Estate
- Neighborhood: White Lake
- Direction Faces: East
School Information
- High School District: Monticello
- Elementary School: Emma C Chase School
- Middle School: Robert J Kaiser Middle School
- High School: Monticello High School
Community
- Association: Yes
- Assoc. Fees Include: Common Area Maintenance, Grounds Care, Snow Removal
Heating & Cooling
- Central air: Yes
- Cooling Type: Central Air
- Heating Type: Forced Air, Propane
Utilities
- Sewer: Septic Tank
- Water: Well
- Utility Description: Cable Connected, Electricity Connected, Phone Connected, Sewer Connected, Trash Collection Private, Underground Utilities, Water Connected
Structural Information
- Architectural Style: Chalet, Contemporary, Craftsman
- Detached/Attached: Detached
- Construction: Stone, Wood Siding
- Unfinished Attic: Yes
- Windows: Insulated Windows, Oversized Windows, Screens
- Sq. Ft. Source: Measured
- Year Built: 2003
Lot Features
- Lot Size (Acres): 5.04
- Lot Size (Sq. Ft.): 219,542
- Frontage Feet: 409 Feet
- Road Maintenance: Road Maintenance Agreement
- 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
Water Features
- Water Front: Yes
- Water Front View: Lake Front, Water Access, Waterfront
Financial Considerations
- Association Fee: Yes
- Association Fee: $167
- Assoc Fee Freq.: Monthly
- Tax Amount: $25,632
Disclosures and Reports
- Special Conditions: None
- Property ID: 2000-055-E-0001-003-000
Listed by Boller Properties
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Schools
Schools serving 51 Homestead Trail
School District:Monticello Central School District
| Name | Grades | Distance |
|---|---|---|
Kenneth L Rutherford School 26 Patricia Place, Monticello, NY 12701 | 3-5 | 7.8 mi |
Robert J Kaiser Middle School 45 Breakey Avenue, Monticello, NY 12701 | 6-8 | 7.7 mi |
Monticello High School 39 Breakey Avenue, Monticello, NY 12701 | 9-12 | 7.7 mi |
Disclaimer:
School attendance boundaries provided by ATTOM Data Solutions and are for reference only. Contact the school directly to verify enrollment eligibility.
Price & Sales History for 51 Homestead Trail
Date
Details
Price
Change
Source
9/10/2026
Price Reduced
$1,250,000
-3.47%
MLS
8/28/2026
Listed
$1,295,000
—
MLS
Disclaimer: Historical sales information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.
Estimate the Cost
Estimate the Cost for 51 Homestead Trail
51 Homestead Trail, White Lake, NY 12786 (MLS# 1034443) is a Single Family property with 4 bedrooms, 3 full bathrooms and 1 partial bathroom. 51 Homestead Trail is currently listed for $1,250,000 and was received on August 28, 2026. Want to learn more about 51 Homestead Trail? Do you have questions about finding other Single Family real estate for sale in White Lake? You can browse all White Lake real estate or contact a Coldwell Banker agent to request more information.
