Tara Gayle

Is a landscape designer with an emphasis in resilient ecological design. In addition to becoming a certified soil consultant, her education has taken her across the country and the world, studying permaculture design and regenerative agricultural systems. At the core of her philosophy is a mission to encourage people to look at their environments holistically, [...]

By |2025-07-15T22:46:27-04:00July 15th, 2025||Comments Off on Tara Gayle

Matt Flanders

Has been providing quality property services to discerning clients, both on Martha's Vineyard and elsewhere, over the past thirty years. As an individual with island roots many generations deep, Matt's integrity and reputation are well known and he considers them to be the foundation on which he stands. His reputation for being dependable, honest, trustworthy [...]

By |2025-07-15T22:46:13-04:00July 14th, 2025||Comments Off on Matt Flanders

Thomas Enders

Is a Senior Managing Director with Manatt Health, the integrated consulting, policy, and legal division of Manatt, Phelps, and Phillips, a leading national law firm. Tom works with academic health centers, medical schools, and children’s hospitals on the unique organizational, financial, and operational challenges posed by academic medicine. Tom is a graduate of Phillips Exeter, [...]

By |2025-07-15T22:46:04-04:00July 13th, 2025||Comments Off on Thomas Enders

Ellen Harley

Holds a Master’s degree in City and Regional Planning from the University of Pennsylvania and holds a B.A. in English from Monmouth University. In 2004, she founded and chaired the Southern Women’s Campaign School, a non-partisan organization that provides training and information for women seeking to run competitive campaigns. In 1995, she founded the Center [...]

By |2025-07-16T11:48:03-04:00July 12th, 2025||Comments Off on Ellen Harley

Matthew Dix

Moved to Martha’s Vineyard in 1990. He and his wife, Rebecca Miller, own and operate North Tabor Farm. They also have three children who were born and raised on the farm. Matthew recently retired from the Martha’s Vineyard Land Bank after 27 years, much of those spent as their property foreman. He has a strong [...]

By |2025-07-15T22:44:38-04:00July 12th, 2025||Comments Off on Matthew Dix

Ben Martin

Ben is an avid runner and surfer and lives on the Island with his wife, Hilary Dreyer, and their husky mix rescue dog, Potato. Having met Hilary on one of the Island’s trails back in college, Ben has a deep love of preserving the Island’s lands to be enjoyed by all. Ben originally began visiting [...]

By |2025-07-18T16:41:31-04:00July 11th, 2025||Comments Off on Ben Martin

Megan Greenglass

was born and raised on Martha’s Vineyard and is now a seasonal resident of Edgartown. She grew up horseback riding at Crowhollow Farm and running cross-country and track at the Martha’s Vineyard Regional High School. Megan remains closely connected to the Island and enjoys spending time on the water with her husband and children.  

By |2025-07-16T11:45:48-04:00July 11th, 2025||Comments Off on Megan Greenglass

Jonathan Steinberg

has summered since 1962 at his family retreat off of Lighthouse Road in Aquinnah. He studied at Putney School, UC Berkeley, the Université d’Aix/Marseille, and UCLA School of Law.  He was a partner at Irell & Manella LLP for three decades, where he focused on congressional redistricting, voting rights and intellectual property litigation.  As a [...]

By |2025-07-14T13:55:11-04:00July 11th, 2025||Comments Off on Jonathan Steinberg

William A. Plapinger

Was a partner, in New York and London, for almost three decades (and is now Senior Counsel) at the global law firm Sullivan & Cromwell LLP. Bill and his wife Cassie Murray have been seasonal, and more recently permanent, residents of the Vineyard since 1968. They built a home near Cedar Tree Neck in the [...]

By |2025-07-16T11:51:50-04:00July 11th, 2025||Comments Off on William A. Plapinger

Brien O’Brien

Brien and his wife Mary Hasten make their primary residence in Chicago but have been seasonal residents of Martha’s Vineyard since the 1980s. Brien is Chairman and CEO of Port Capital, a global investment management firm which manages domestic and developed markets global equity strategies. In addition to his career in the financial industry over [...]

By |2025-07-18T16:43:06-04:00July 11th, 2025||Comments Off on Brien O’Brien
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