On Martha’s Vineyard, where culture, history, and tradition meet, one home stands as both a sanctuary and a symbol. Known as My Angel’s Smile, the property, designed by owner Leslie A. Hayling Jr, D.D.S., to honor his parents, Adrienne Hayling and Leslie A. Hayling D.D.S., affectionately known as “Mom” and “Big Daddy,” holds a name rich with meaning. Beyond its idyllic exterior, the property represents decades of legacy, love, and resilience.
The home was initially purchased by Hayling’s family in 1968 during a time when Black homeownership on the island was far from common. Over time, the residence has become a powerful marker of perseverance. In recent years, Hayling has faced ongoing resistance from a small group of neighbors who have challenged his efforts to preserve and expand the property. Despite the obstacles, he remains steadfast in protecting what his parents began and ensuring the home continues to shine as a beacon of Black heritage on Martha’s Vineyard.
Leeza A. Singh, founder and CEO of The Renaissance Group, is also pushing the legacy of My Angel’s Smile through her creative direction and event curation. For Singh, hosting gatherings at the home is more than just part of her business—it’s a purpose.
“It gives me great joy,” Singh says. “Bringing visions to life in this house means honoring history while creating new stories that will be remembered for generations.”
From intimate dinners to large-scale celebrations, Singh transforms the property into a living canvas where legacies are preserved and new traditions are born. Her events have welcomed some of today’s most influential brands and organizations, including Louis Vuitton, Moët Hennessy, Amazon, Time Magazine, the National Urban League, TD Jakes Enterprises, and Citibank. Each partnership underscores the home’s growing reputation as a hub for connection, celebration, and cultural impact.
Through her work with My Angel’s Smile, Singh is not only preserving a family legacy, she’s also expanding it. Every carefully curated event adds another chapter to the home’s story, reinforcing its role as a sacred space for joy, remembrance, and storytelling.
My Angel’s Smile stands as a reminder that heritage can be honored one gathering, one story, and one generation at a time.