When Robert Winston and his teenage son, Maynard, first wheeled their pushcart of flowers down Boston’s fashionable Newbury Street in 1944, they could not have foreseen how their humble enterprise would one day become one of New England and New York’s most highly regarded businesses. It was from this pushcart outside of the original Ritz-Carlton hotel in Boston that the father-son team would lay the guiding principles and philosophies of a company that would eventually become ‘Florist of the Year,’ a frequent ‘Best of Boston’ award winner, and a perennial client favorite.

It was Maynard Winston who expanded the business and helped it evolve into one of the country’s premier florists. Under his guidance, Winston Flowers made its name as a forward-looking Newbury Street boutique with the finest floral designers available and a discerning clientele. Acting on a tip from a Dutch employee, the company was the first florist in the country to import flowers directly from overseas, delighting Bostonians with exotic new varieties of freesia, lilac, and tulips flown in from Holland exclusively for Winston Flowers.

Maynard emphasized hard work, innovation, and friendly service. As the owner, he also did not hesitate to personally deliver flowers to a client, often taking public transportation or walking through Back Bay or Beacon Hill to do so. Likewise, he always encouraged his young sons David and Ted to do the same. 

Today, the third-generation, family-owned company is run by David and Ted Winston and is recognized as one of the country’s most highly esteemed florists, with a worldwide online presence and seven shops throughout Massachusetts and Greenwich, CT, as well as a new location in New York City. With over seventy years of experience and a reputation for unparalleled service, award-winning floral design, spectacular special events, innovative garden design, and more, Winston Flowers is not only one of Boston’s first florists, but one of the country’s leaders in floral artistry, touching clients in Boston, Greenwich, Manhattan, and beyond. From pushcart roots to the world-class reputation it holds today, the guiding tenets of warm service and innovation have never wavered.