This is a carousel with tiles that activate property listing cards. Use the previous and next buttons to navigate.
1/23
$1,295,000
This is a carousel with tiles that activate property listing cards. Use the previous and next buttons to navigate.
1/23
Property Description
Anchored gracefully along four hundred feet of shoreline on the coveted 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. The light-flooded contemporary chalet is tucked within an exclusive 2,500-acre gated wilderness preserve, offering unparalleled privacy 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.
Full Property Details
Full Property Details for 51 Homestead Trail
General
- Price: $1,295,000
- HOA FEE: $167/month
- HOA FEE FREQ.: Annually
- Taxes: $25,632
- Status: Active
- Type: Single Family
- Source: Long_Island
- MLS ID: 989403
- Updated: 5/21/2026
- Added to Site: 30 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: 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, Heated Garage
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: $2,000
- Assoc Fee Freq.: Annually
- Tax Amount: $25,632
Disclosures and Reports
- Special Conditions: None
- Property ID: 2000-055-E-0001-003-000
Listed by Boller Properties
Get Pre-Approved Today
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
4/23/2026
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# 989403) is a Single Family property with 4 bedrooms, 3 full bathrooms and 1 partial bathroom. 51 Homestead Trail is currently listed for $1,295,000 and was received on April 23, 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.
