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Win Baker

Vice President of Operations
(774) 357-1495(office)

Win comes to Martha's Vineyard after many years in the media business in New York, the Internet and technology worlds of Silicon Valley, and the luxury hospitality field in Newport, Rhode Island. He now oversees operations at both the sales and rental divisions.


Throughout his entrepreneurial journey, his leadership and management style have been pivotal in building and scaling up a number of sales, support, marketing, production, and operation teams at both the start-up and corporate level from guiding a group of small luxury hotels to become Rhode Island's top-rated AAA 4-Diamond hospitality group, to co-founding an influential cloud video technology platform, to the launch of a Cable TV network and streaming service, to overseeing a $2-Billion acquisition and integration of several technology companies with hundreds of employees.


He is a recognized specialist in several areas: customer service and guest experience; real estate, vacation rental, and hospitality technology platforms; digital and social media marketing; as well as an Emmy award-winning video producer/writer/director and professional photographer. He has produced thousands of hours of live, on-demand, and streaming video, and published photographic work in Architectural Digest, the New York Times, Wall Street Journal, and the Boston Globe among others.


A seasoned property investor, the Vineyard has been a natural fit for Win, where he and his wife have renovated and sold three homes, as well as owning and operating several luxury vacation rentals. They live in Edgartown, where they're working together on their fifth project.