James Lane Post has partnered with Saunders & Associates to create the series “The Saunders Stewardship Impact,” which shines a light on the organizations that are close to the hearts of its agents. This is the fifth installment, featuring Saunders & Associates’ real estate agent, Penelope Moore, who spotlights East Hampton Library’s Authors Night, of which Saunders is a sponsor.
Some real estate professionals focus on the sale. Penelope Moore never saw it that way. She’s made a career — almost three decades — caring for Shelter Island as if it were her own home, not just a collection of addresses on a map. She’s as invested in the island’s traditions as she is in finding buyers for its historical farmhouses or shingle cottages.
Moore’s dedication goes beyond real estate: she’s been at the heart of the island’s nonprofits, thrown her energy into local traditions, and worked to protect the quirks that make Shelter Island feel different from anywhere else. In a conversation for the Saunders Stewardship Series, Moore opens up about how a true sense of community holds its value longer than any market trend. Moore admits that even now, after all these years, the island’s enduring spirit still surprises her.
You’ve built an extraordinary career representing Shelter Island and the East End. What first drew you to this unique market, and what continues to inspire you nearly three decades later?
I first visited Shelter Island in May of 1995, and as soon as I got on the ferry, a sense of tranquility came over me. The salt air, the buoyancy of the waves, the ferry purser who came up to chat, painted a picture of a bygone day that was immensely appealing. I had previously summered in Nantucket, but reaching it required considerably more time and planning. Shelter Island offered that same feeling of escape, yet was much closer to Manhattan. As I arrived at the North Ferry landing, my first thought was to go to a real estate office to see what was going on in the market. The real estate agent took me to see six properties, and I asked her, “Because this is my first time on the island, can you tell me what you would pick for me if I were your daughter?” She selected one house, saying it was close to everything I wanted (beach, golf, proximity to the ferry) and within my price range. I made an offer on the spot and am still in that same house. It was the genuine friendliness of the people and the respect everyone seemed to have for the island’s natural beauty that drew me here and which continues to inspire me every day.
Shelter Island has a distinct personality from the Hamptons. How do you describe its appeal to buyers who may be discovering it for the first time?
Some buyers immediately feel that special something about living on an island surrounded by salt water, just like I did. Shelter Island has some of the best waters in the country for sailors and boaters looking for a dock that suits their boat. We are also situated between the North and South Forks, each of which offers unique experiences, so we truly have the best of both worlds. Whether you are a nature lover who enjoys a stroll in the meadows at Mashomack in the springtime when birds are at their most active, a music lover who who loves to see young, gifted musicians at the Perlman Music Center, an art lover who looks forward to the summertime open houses at artists homes called “ARTSI,” someone who thrives on a bustling social scene and people watching at Sunset Beach, a golf lover (there are two courses here, one public and the other private)… the list is endless, there is truly something for everyone.
Many of the homes you represent have rich histories and architectural significance. What role does storytelling play in helping buyers connect with a property?
I grew up in Washington, D.C., where my family had a townhouse in Georgetown that backed up to the C&O Canal. Every weekend was spent going to the Smithsonian Institution and then to open houses all over town; my parents, you see, were “aspirational” buyers, always looking for the next place. My father was a writer/producer at NASA and a journalist, and my mother an artist, so they were always curious about history, what a house had to say, and the pros and cons of its design. When I’m showing a home, I’m not just pointing out square footage or bedroom counts. I’m trying to help buyers understand why the house was built the way it was, what prior owners have contributed to the home, and how the buyers might become a part of its evolving story. I think that’s what transforms a house into a home that people remember long after they have finished a tour. Some houses here on the island I have seen change hands a half dozen times and know the finishing touches each owner brought to it.
Today’s luxury buyers are looking for more than just beautiful homes. What lifestyle trends are shaping the market on Shelter Island and across the East End?
On Shelter Island, buyers’ preferences vary, but I continue to see strong demand for both restored/turnkey homes and vintage homes waiting for their next steward. Privacy, acreage, and a relationship with the water remain enduring priorities.
Looking ahead, what do you hope remains unchanged about Shelter Island, even as demand continues to grow?
I hope that the natural beauty we have here remains unchanged — however, property owners also have the right to change their properties as they see fit within the zoning code. We are fortunate to have a proactive Community Preservation Fund that earmarks properties meaningful to the island’s character and environment. It seems like people who have come to the island over the years want to preserve the life they grew up in for their own kids, regardless of where they actually grew up. There is a timeless feeling about this place that is hard to find within 100+ miles of Manhattan.
You’ve long been involved in supporting the East Hampton community. What makes Authors Night (held August 8) such a meaningful event for you personally?
My father was a writer and journalist (whose claim to fame was turning down an offer from Stanley Kubrick to co-write “2001: A Space Odyssey”) who encouraged my sisters and me to talk about what we were reading and what we loved about the book. Televisions were forbidden in the household, and most nights after dinner, we would walk to the library where we knew the librarians, so libraries like East Hampton Library were an important part of my childhood. My maternal grandfather was a Japanese artist, a “National Living Treasure,” and although he didn’t speak English, he pored over books with a magnifying glass and dictionary and would go to book fairs and to the Library of Congress (he was commissioned by the Federal government to do a woodblock print of the library, in fact). We all had allergies from the book dust!
When I attend Authors Night, that excitement of being around books and the Authors comes back. I already know so many people from Shelter Island whose books are featured there — clients, tenants, friends — so it’s a wonderful opportunity to catch up with people I truly adore under one tent. I also meet new people and share stories, like with Neil DeGrasse Tyson about my father’s bad decision about “2001,” Alec Baldwin who was a client of mine in the city when I worked in entertainment, Chris Whipple who is a long time client, Christian John Wikane who shares a love of disco and fashion, Carl Bernstein who was once a client, Susan Morrison who is a Shelter Island friend… well the list is lengthy!
Authors Night has become one of the Hamptons signature cultural events. Why do you think it continues to resonate with both year-round residents and summer visitors?
Although there are author festivals across the country, the East Hampton Library Authors Night is a very unique event because it brings together people across a wide age range under one tent, and those who would like to spend an evening with their favorite author can enjoy a cozy dinner with them at the home of a host. Attendees can meet authors or celebrities they admire, learn something new, and get that feeling of excitement that I have every year. I always invite friends who have no idea what to expect and who always leave with a couple of large bags of inscribed books; the timing of the event is perfect too for beach reading, and I tend to do most of my Christmas shopping there.
Literature, history, and real estate all revolve around stories. Do you see a connection between introducing someone to a home and introducing them to a great book?
Oh absolutely! All three of these subjects share common threads, such as surprise endings, twists and turns along the way, insight into a person’s motivations, and their quest for happiness. Often, while showing houses, something arises that leads to a conversation about a book. Very often I have that book at home from Authors Night and end up giving it to my customer to enjoy. I love the idea that a conversation about a house can lead someone to discover a wonderful story as well.
Community involvement seems to be an important part of your professional life. How has giving back enriched your career and your connection to the East End?
One of the nicest things about living in a small community is that your professional life and your personal life naturally overlap. You aren’t just selling someone’s house — you run into them at the grocery store, at the ferry, at a charity event, or years later when they’re introducing you to their grandchildren. Supporting organizations like Authors Night, the Perlman Music Program, Bay Street Theater, Turtle Rescue Center of the Hamptons, Gimme Shelter Animal Rescue, and many local nonprofits has allowed me to become part of the fabric of the community rather than simply someone who works in it. It has also introduced me to remarkable people I never would have met otherwise. Those relationships have enriched my life far beyond real estate, and I think people appreciate doing business with someone who genuinely cares about where they live.
When you think about the future of the Hamptons and Shelter Island, what gives you the greatest sense of optimism, both professionally and personally?
I feel optimistic for the future of the Hamptons and Shelter Island seeing people discover the area for the the first time and watching them experience the same simple pleasures that have always existed here — fishing from a dock, learning to sail, picking strawberries or pumpkins in a farmfield, riding bikes to the beach, going to a concert, and exploring the East Hampton Library and the Shelter Island Library, which is in the midst of expansion. Professionally, I also see an appreciation for quality over quantity. Buyers are looking for homes that allow them to slow down, spend meaningful time together, and enjoy nature. Those values have always been part of Shelter Island’s identity, and I think they’ll continue to attract people for generations.
If you could introduce someone who’s never visited the East End to just one place, one home, one book, and one local tradition, what would you choose, and why?
One home, “Kemah,” which was built around 1750, encompasses 17.35 acres and has had only three owners since it was built. Obadiah Havens, a Patriot whose family was the first owners, signed the 1775 Shelter Island Declaration of Independence. The Indigenous people who came before them treasured Fresh Pond, the hidden body of water behind this house, for its fresh water source. Its center hall colonial home and gracious barns have been immortalized in paintings and sketches by residents and visitors alike. Even today, if you stand at Kemah and look toward the South Fork, it isn’t difficult to imagine Indigenous people keeping watch across the water centuries ago, or later, Obadiah Havens contemplating the uncertain future of a new nation.
One book would be “The Manor: Three Centuries at a Slave Plantation on Long Island” by Mac Griswold, who was a featured author at Authors Night a few years ago. It is a riveting book that chronicles the intertwined histories of Indigenous people, enslaved Africans, European settlers, and emancipation through the remarkable story of Sylvester Manor, the families who shaped Shelter Island and the East End, and gives readers an appreciation for the history of the East End that extends far beyond its beautiful beaches and homes.
Choosing just one tradition is difficult, but I always look forward to the Snapper Derby over Labor Day Weekend. Children spend weeks preparing for this event: finding a good fishing spot, creating colorful hand-painted murals, and eagerly awaiting the official weigh-in. After the trophies are awarded and the best mural recognized, the day ends with a community barbecue at the American Legion Hall. It’s a tradition that has introduced a new generation to the joys of fishing and reminds everyone what small-town life is all about.
To learn more about Moore, visit hamptonsrealestate.com.
