Winston Flowers, a beloved Boston institution renowned for its elegant floral arrangements, is set to open a new chapter at The Street Chestnut Hill this August. From its humble beginnings 80 years ago as a floral pushcart by Robert Winston and his son Maynard outside the original Ritz-Carlton, the brand has evolved into a symbol of sophistication akin to Tiffany & Co. for flowers. Today, Winston Flowers graces the city’s finest hotels, luxury condos, and exclusive venues like the ’Quin House, with its exquisite bouquets a perennial favorite for occasions ranging from Valentine’s Day to Mother’s Day.
Adapting to shifts in consumer preferences and the floral industry landscape has been key to Winston Flowers’ enduring success. The company’s flagship garden center on Florence Street in Chestnut Hill, which included greenhouses and outdoor gardens, faced redevelopment prompting a strategic rethink. “Customer shopping habits, both in-store and online, have evolved significantly,” notes Ted Winston, who alongside his brother David, inherited the business in the 1980s. Responding to diminished demand for traditional garden services, the brothers saw an opportunity to relocate to nearby The Street Chestnut Hill, aiming to revitalize direct engagement with the Winston Flowers brand through interactive experiences.
While maintaining existing retail locations and design studios in New York City and Boston’s South End, Ted and David have meticulously crafted the new Chestnut Hill space. Designed to accommodate workshops in flower arranging, container gardening, and even wine tastings, the new location reflects their commitment to enhancing customer interaction. Beyond flowers and plants, the shop will feature an expanded selection of gourmet gift boxes showcasing locally sourced delicacies such as handmade chocolates, cheeses, wines, and cookies from artisans like Gräem Nuts and Chocolate and Mrs. Mekler’s Mercantile.
This gourmet division marks a burgeoning segment for Winston Flowers, underscoring its evolution from its modest beginnings to a diversified luxury brand. “We are incredibly excited about the future,” affirms Ted, reflecting on the journey from their grandfather’s initial pushcart venture.
Winston Flowers will continue to operate at its other locations, including 31 Central St., Wellesley; 131 Newbury St., Boston; and 33 Boylston St., Chestnut Hill at The Street Chestnut Hill. The new location promises to redefine the Winston Flowers experience, blending tradition with innovation in floral artistry and gourmet craftsmanship.
