A Conversation with Lewis Ranieri About “Treetops,” an Award-Winning Shelter Island Modern

Perched 162 feet above sea level on one of Shelter Island’s highest natural elevations, the modern residence at 42 Prospect Avenue + Part 23 Serpentine Drive, known as “Treetops,” is recognized for both its architecture and its wide-ranging views. Built in 2002 and designed by architect Frederick Stelle, who was honored with an AIA Archi Award, the home was inspired by the original structure on this site that was designed by Peter Schladermundt—whose work was featured at the 1964 New York World’s Fair.

Set on 3.41 acres, the three-story residence overlooks Peconic Bay, the North Fork, Long Island Sound, and, on clear days, has views to the Connecticut shoreline. The design uses expanses of glass to open the house to its surroundings, keeping the landscape in constant view.

Owned by financier Lewis Ranieri, widely recognized for his role in developing the mortgage-backed securities market, the property serves as a counterpoint to the pace of his professional life.

Born in New York, Ranieri has a longstanding interest in history and the arts, with an keen eye for aesthetics. While the design of the house had meaning, it was the soaring elevation, the views, and the sense of quiet that made a lasting first impression. 

Listing broker Penelope Moore of Saunders & Associates, recently visited with Ranieri at Treetops for a conversation.

Penelope Moore: Well, it looks like I caught you in the middle of welcoming spring, putting out your deck pillows! It’s nice to finally have the sun come out and to see you in person after a long winter.

Lewis Ranieri: Yes! This is a place I think about when I’m away from here. In my mind’s eye it is ethereal, and driving out, I think to myself: how much will it have changed since the snow has melted, for example. Then, as I open the front door, there is the realization that the ethereal is in fact a reality…and the seasonal changes are aligned with the changes that happen over the course of a day. It is hard to describe, but Treetops is a living and breathing entity in so many respects. 

Moore: What were your first impressions of the house when you toured it, and what made you go on to purchase it?

Ranieri: I have had many homes over the years, always leaning toward the traditional. And those traditionals, I have always loved tweaking and improving upon. When we pulled up in the driveway here, I really had no intention of buying a modern home but thought, well we are here so let’s take a look.  When I walked in, the eyeful of sky, trees, blue water and the sound of rustling leaves and birds was like nothing I had ever seen on Long Island, and I should add that there are very few places in the world that have a view like this.

Moore: Yes I remember your home search was geared toward traditional, waterfront homes.  We had seen some pretty expansive ones, too. 

Ranieri: The one thing I realized was that although I originally wanted to be on the water and in a classic “Hamptons” style house, what Treetops had and continues to have were materials and textures that were well designed and…timeless even though they are considered modernist. This home is not fussy, it is confident in its own skin, straightforward, and by the same token, it doesn’t fall into the trap that many modern homes seem to fall into of being “cold”.  Frederick Stelle capitalized on the site and the soft touches that Peter Schladermundt incorporated into his design. Do you remember how elegant the structures at the 1964 Worlds Fair were? Timeless, and yet they were called modern.

Moore: What do you enjoy doing when you’re at Treetops?

Ranieri: Above all, literally and figuratively, I love taking in the view—and being within the quiet. I feel removed from all the madness when I am here. Where you and I are sitting, looking out to Southold, over the North Fork and to Connecticut..the scenery that captures the angles of the sun is enough to bring my blood pressure down in a nanosecond! The view actually has very few structures that are visible to the eye, and the way we trim the trees keeps the vista natural, although we have subtly manicured it so it doesn’t appear untamed. So that’s probably what I love first and foremost.

This house and its outdoor spaces are where I catch up with family and friends. They love the pool and the deck, of course. We grill on the eastern deck and then make a phenomenal tomato and sausage pasta. And I can almost see my friend Itzak [Perlman] conducting over there at Perlman Music Camp!

Moore: Now that you mention it, I have come to visit when you are “air-conducting” and listening to classical music…

Ranieri: Well, as you know, I love opera, classical music…really any good music…Treetops and the sense of tranquility, and of being above the clouds seem to go hand in hand with music. 

Moore: The rooftop terrace is literally above the clouds, isn’t it?

Ranieri: Oh yes, what a vantage point! For July 4th festivities, we are above the fireworks that are going off over the bay. How many places are like that around here?

Moore: None that I know of! From the rooftop terrace, you can see the garden you created too.

Ranieri: The first year we were here, I had an idea of designing a curved bluestone garden path just beyond the pool, with the focus being a burst of color from a variety of florals and leaves, with textures and patterns that complement the stone and metal that are a part of the house.

The key to moderns, I think, is adding rounded accents to the right angles that modern homes inherently have, and doing that with plants and flowers in a way that doesn’t overshadow the house. This is what gives me visual joy, and a feeling of connection with my surroundings.

Moore: Just beyond the garden path, you have this rolling expanse of meadow.

Ranieri: The kids sled there when it snows. In the summer, it’s a scenic buffer. That slope also got me thinking about an addition to the house built into the hill, which I designed as a sort of phase two, with a subterranean gallery with expanses of wall space and shafts of natural light with a separate guest wing.

Additional features of the approximately 4,100-square-foot residence include three bedrooms, three full baths and one half bath, radiant heated floors, multiple fireplaces, a glass-lined staircase illuminated by nineteen-foot etched windows, a gym and sauna, and a lower level that opens to a 57-foot heated Gunite pool surrounded by established perennial gardens.

As noted by Hamptons Cottages & Gardens, the setting has an almost otherworldly quality: “Clouds floating by overhead appear within reach, and the sunsets are cinematic events.”

For Ranieri, however, the takeaway is simple: “This is a place that comes once in a lifetime and I haven’t taken for granted.”