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    1 home
    1 home available
    42 Prospect Ave + Part 23 Serpentine Drive, Shelter Island, NY 11964
    $7,950,000
    3beds
    3.5bath
    4,133sqft
    3.41acres
    House for Sale

    42 Prospect Ave + Part 23 Serpentine Drive, Shelter Island, NY 11964

    Listing by: Saunders & Associates
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    Copyright © 2025 OneKey® MLS LLC
    Display of MLS Data is usually deemed reliable but is NOT guaranteed accurate by the MLS. Buyers are responsible for verifying the accuracy of all information and should investigate the data themselves or retain appropriate professionals.
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    42 Prospect Ave + Part 23 Serpentine Drive, Shelter Island, NY 11964
    42 Prospect Ave + Part 23 Serpentine Drive, Shelter Island, NY 11964
    42 Prospect Ave + Part 23 Serpentine Drive, Shelter Island, NY 11964
    42 Prospect Ave + Part 23 Serpentine Drive, Shelter Island, NY 11964
    42 Prospect Ave + Part 23 Serpentine Drive, Shelter Island, NY 11964
    42 Prospect Ave + Part 23 Serpentine Drive, Shelter Island, NY 11964
    42 Prospect Ave + Part 23 Serpentine Drive, Shelter Island, NY 11964
    42 Prospect Ave + Part 23 Serpentine Drive, Shelter Island, NY 11964
    42 Prospect Ave + Part 23 Serpentine Drive, Shelter Island, NY 11964
    42 Prospect Ave + Part 23 Serpentine Drive, Shelter Island, NY 11964
    42 Prospect Ave + Part 23 Serpentine Drive, Shelter Island, NY 11964
    42 Prospect Ave + Part 23 Serpentine Drive, Shelter Island, NY 11964
    42 Prospect Ave + Part 23 Serpentine Drive, Shelter Island, NY 11964
    42 Prospect Ave + Part 23 Serpentine Drive, Shelter Island, NY 11964
    42 Prospect Ave + Part 23 Serpentine Drive, Shelter Island, NY 11964
    42 Prospect Ave + Part 23 Serpentine Drive, Shelter Island, NY 11964
    42 Prospect Ave + Part 23 Serpentine Drive, Shelter Island, NY 11964
    42 Prospect Ave + Part 23 Serpentine Drive, Shelter Island, NY 11964
    42 Prospect Ave + Part 23 Serpentine Drive, Shelter Island, NY 11964
    42 Prospect Ave + Part 23 Serpentine Drive, Shelter Island, NY 11964
    42 Prospect Ave + Part 23 Serpentine Drive, Shelter Island, NY 11964
    42 Prospect Ave + Part 23 Serpentine Drive, Shelter Island, NY 11964
    42 Prospect Ave + Part 23 Serpentine Drive, Shelter Island, NY 11964
    42 Prospect Ave + Part 23 Serpentine Drive, Shelter Island, NY 11964
    42 Prospect Ave + Part 23 Serpentine Drive, Shelter Island, NY 11964
    42 Prospect Ave + Part 23 Serpentine Drive, Shelter Island, NY 11964
    42 Prospect Ave + Part 23 Serpentine Drive, Shelter Island, NY 11964
    42 Prospect Ave + Part 23 Serpentine Drive, Shelter Island, NY 11964
    42 Prospect Ave + Part 23 Serpentine Drive, Shelter Island, NY 11964
    42 Prospect Ave + Part 23 Serpentine Drive, Shelter Island, NY 11964
    42 Prospect Ave + Part 23 Serpentine Drive, Shelter Island, NY 11964
    42 Prospect Ave + Part 23 Serpentine Drive, Shelter Island, NY 11964
    42 Prospect Ave + Part 23 Serpentine Drive, Shelter Island, NY 11964
    42 Prospect Ave + Part 23 Serpentine Drive, Shelter Island, NY 11964
    42 Prospect Ave + Part 23 Serpentine Drive, Shelter Island, NY 11964
    42 Prospect Ave + Part 23 Serpentine Drive, Shelter Island, NY 11964
    42 Prospect Ave + Part 23 Serpentine Drive, Shelter Island, NY 11964
    42 Prospect Ave + Part 23 Serpentine Drive, Shelter Island, NY 11964
    42 Prospect Ave + Part 23 Serpentine Drive, Shelter Island, NY 11964
    42 Prospect Ave + Part 23 Serpentine Drive, Shelter Island, NY 11964
    42 Prospect Ave + Part 23 Serpentine Drive, Shelter Island, NY 11964
    42 Prospect Ave + Part 23 Serpentine Drive, Shelter Island, NY 11964
    42 Prospect Ave + Part 23 Serpentine Drive, Shelter Island, NY 11964
    42 Prospect Ave + Part 23 Serpentine Drive, Shelter Island, NY 11964
    42 Prospect Ave + Part 23 Serpentine Drive, Shelter Island, NY 11964
    42 Prospect Ave + Part 23 Serpentine Drive, Shelter Island, NY 11964
    42 Prospect Ave + Part 23 Serpentine Drive, Shelter Island, NY 11964
    42 Prospect Ave + Part 23 Serpentine Drive, Shelter Island, NY 11964
    42 Prospect Ave + Part 23 Serpentine Drive, Shelter Island, NY 11964
    42 Prospect Ave + Part 23 Serpentine Drive, Shelter Island, NY 11964
    $7,950,000
    3beds
    3full,1half bath
    4,133sqft
    3.41acres

    42 Prospect Ave + Part 23 Serpentine Drive, Shelter Island, NY 11964

    City/Town:Shelter Island   Post Office: Shelter Island     

    House for Sale by Penelope A. MooreSaunders & Associates.

    Data checked -. Listing last updated 4 days ago.
    1. Overview
    2. Details
    3. More 

    Built in 2002, "Treetops" is an AIA Archi Award-winning modern classic that boasts some of the most sweeping and unobstructed views on Eastern Long Island-stretching across the North Fork, Peconic Bay, Long Island Sound, and reaching to Connecticut. Positioned at 162 feet above sea level on "Divinity Hill" in Shelter Island Heights, it sits at one of the island's highest natural elevations. The home is the result of a thoughtful evolution of an original design by Peter Schladermundt, renowned for his iconic structures at the 1964 New York World's Fair, brought to its current form by noted architect Frederick Stelle. The architectural concept centers around two clean-lined volumes joined by a glass pavilion, using a restrained palette of stone, steel, and glass, executed with clarity and elegance. On the view-facing side of the home, a dramatic pavilion wrapped in 9-foot floor-to-ceiling glass walls provides unobstructed vistas. These are framed with anodized aluminum windows, hand-laid aluminum inlay mouldings, and solid core doors that reflect the home's refined craftsmanship. The main living area is open, featuring a fireplace, radiant heat floors, a screened dining area, and access to two decks, one with a built-in barbecue. An elevated kitchen is outfitted with Poliform cabinetry, high-end appliances, and a butler's pantry. Additional spaces on this level include a family room with Scandinavian fireplace, powder room, laundry, office/library, and a first-floor en-suite guest bedroom. A sculptural bluestone staircase, with treads subtly suspended one inch from a glass wall, rises beside 19-foot acid-etched glass windows, filtering natural light through the space, offering a graceful ascent to the primary en-suite bedroom. An aerie above the canopy of treetops, this suite features a covered rooftop terrace, steam shower, soaking tub, and a Scandinavian propane stove, offering a serene and secluded experience. The at-grade lower level includes recently installed travertine flooring, a guest bedroom with direct access to the pool area, a mirrored gym/exercise studio, Finnleo sauna, full bath, second laundry area, walk-in cedar closet, Eurocave 150-bottle wine cooler, and a Sub-Zero side-by-side refrigerator and freezer. Outdoors, a 57-foot heated freeform Gunite pool is bordered by Arizona buff stone and surrounded by lush perennial gardens. Pathways lead to a separate garden with multilevel bluestone decking and grandfathered steel cord railings, blending natural and architectural elements. As Hamptons Cottages & Gardens once wrote: "This place is indeed divine... not only in the sense of 'oh how divine,' but also in its distinctive sense of other-worldliness. Here the air, the light, the very atmosphere, feels celestial. Clouds floating by overhead appear within reach, and the sunsets are cinematic events." A rare Shelter Island offering, "Treetops" is as much a sanctuary as it is a landmark, complete with a protective vegetative buffer and unmatched architectural pedigree.

    Details
      Property type
    Residential
      Year built
    2002
      Heating
    Forced Air, Oil, Radiant
      Cooling
    Central Air
      Total rooms
    10
      Garage
    No
      City/Town
    Shelter Island
      Post Office
    Shelter Island
      Parking spots
    -
    846909
    MLS ID
    Active
    Status
    04/09/2025
    On Market Date
      Laundry features
    In Basement, Inside, Laundry Room, Multiple Locations
      Flooring
    Hardwood
      Fireplace
    Yes
      Pets allowed
      Architectural Style
    Modern
      View
    Neighborhood, Open, Panoramic, Trees/Woods, Water
    Interior features
    First Floor Bedroom, First Floor Full Bath, Breakfast Bar, Cathedral Ceiling(s), Double Vanity, Eat-in Kitchen, Entrance Foyer, Formal Dining, Granite Counters, Kitchen Island, Primary Bathroom, Open Floorplan, Open Kitchen, Pantry, Recessed Lighting, Sauna, Walk-In Closet(s)
    Exterior features
    Lot features
    Back Yard, Corner Lot, Front Yard, Landscaped, Near Public Transit, Private, Views
    Appliances included
    Dishwasher, Disposal, Dryer, Freezer, Gas Cooktop, Microwave, Oven, Range, Refrigerator, Stainless Steel Appliance(s), Washer, Oil Water Heater, Wine Refrigerator
    Construction materials
    Frame, Stone, Stucco, Wood Siding
    Monthly taxes
    $1,858
    Yearly taxes
    $22,298
    Community Features
    -
    School district
    Shelter Island
    Schools
    Shelter Island School
    Senior community
    No
    Common Charges
    -
    Maintenance
    -
    Additional Fees
    -
    Open Houses
    In-Person
    No upcoming in-person open houses
    Virtual
    No upcoming virtual open houses
    Contact Agent
    Penelope A. Moore
    Penelope A. Moore
    Associate Real Estate Broker, Saunders & Associates
    Direct Number 
     
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    For Sale Nearby
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    Listing by:
    42 Prospect Ave + Part 23 Serpentine Drive, Shelter Island, NY 11964, is a 3 bedroom, 3 bathroom, 4133 sqft. Single Family Residence built in 2002. This property is currently available for sale and was listed on OneKey® MLS on 4-9-2025. The MLS# for this Single Family Residence is MLS# 846909.
    Display of MLS Data is usually deemed reliable but is NOT guaranteed accurate by the MLS. Buyers are responsible for verifying the accuracy of all information and should investigate the data themselves or retain appropriate professionals.
    Copyright ©2025
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