Prospect Ave & Part 23 Serpentine Drive

Shelter Island Heights | New York

The Standard of

Cottage Living

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Penelope Moore

Presented At

$7,950,000

Bedrooms

Bathrooms

Living

4,133

SQFT

Fireplace

Library

Office

Fitness Center / Gym

Laundry Room

Sauna

Terrace

Garden

Pool

Privacy

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Prospect Ave & Part 23 Serpentine Drive

Shelter Island Heights | New York

42 Prospect Ave & Part 23 Serpentine Drive, Shelter Island Heights, New York, United States. , Shelter Island Heights , New York

Residential in Shelter Island

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.

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Property Location

42 Prospect Ave & Part 23 Serpentine Drive, Shelter Island Heights, New York, United States., Shelter Island Heights New York

Local Weather & Climate

Shelter Island Heights, New York

Current Conditions Updated recently

38 °F

Overcast clouds

Feels Like 31°F

Humidity 58%

Wind 10 mph

Visibility 2.1 mi

Sunrise 11:04 AM

Sunset 10:53 PM

5-Day Forecast

Fri 13 Mar

Rain

High 38°

Low 38°

Sat 14 Mar

Clouds

High 43°

Low 38°

Sun 15 Mar

Clouds

High 40°

Low 33°

Mon 16 Mar

Rain

High 52°

Low 39°

Tue 17 Mar

Rain

High 53°

Low 35°

Data from OpenWeatherMap

Walkability & Transit Scores

How easy is it to get around Shelter Island Heights?

Walkability and transit scores for this address come from the EPA National Walkability Index.

Mortgage Calculator

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Home Price

Down Payment

$100,000

Interest Rate

Loan Term

Estimated Monthly Payment $3,160

Monthly Payment Breakdown

Principal & Interest $2,528

Loan Amount $400,000

Total Interest $337,621

Total Cost $737,621

Potential Tax Benefits (United States)

$0 Est. First Year Interest Deduction

$0 Est. Annual Tax Savings

*Based on post-2017 tax law. Actual deductions depend on filing status, itemization, and current tax laws.

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Important Information

This calculator is for illustrative purposes only and does not constitute a loan offer, pre-approval, or commitment to lend.
Monthly payment estimates do not include property taxes, homeowner's insurance, HOA fees, or other applicable costs which may significantly increase your actual payment.
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Frequently Asked Questions

Common questions about this property

How many bedrooms and bathrooms does 42 Prospect Ave & Part 23 Serpentine Drive, Shelter Island Heights, New York, United States have?

This house at 42 Prospect Ave & Part 23 Serpentine Drive, Shelter Island Heights, New York, United States features 3 bedrooms with 4,133 square feet of living space.

What is the size of 42 Prospect Ave & Part 23 Serpentine Drive, Shelter Island Heights, New York, United States?

This property offers 4,133 square feet of living space.

What is the listing price for 42 Prospect Ave & Part 23 Serpentine Drive, Shelter Island Heights, New York, United States?

This property is listed at $795,000,000, which equals $192354 per square foot.

What type of property is 42 Prospect Ave & Part 23 Serpentine Drive, Shelter Island Heights, New York, United States?

This is a house located in Shelter Island Heights, New York. The property is situated in an established neighborhood with convenient access to local amenities and services.