Winston Flowers Moves to The Street Chestnut Hill

After decades in its flagship Newton location, the Tiffany & Co. of bouquets puts down roots in a brand-new retail spot.

Photo courtesy of Winston Flowers

It’s safe to say that Winston Flowers has come a long way since Robert Winston and his teenage son, Maynard, started a floral pushcart in the Back Bay outside the original Ritz-Carlton (now the Newbury Boston hotel) 80 years ago. Today, the iconic Boston brand is like the Tiffany & Co. of flowers: You can find its artful installations at the city’s top hotels, in the lobbies of luxury condominium buildings, and displayed at the ’Quin House. Winston’s bouquets, meanwhile, are a must-have come Valentine’s Day, Mother’s Day, and every occasion in between.

The company’s longevity has as much to do with its ability to respond to changes in the floral industry as it does its gorgeous arrangements. Starting in 2000, Winston’s longtime flagship on Florence Street in Chestnut Hill operated as a garden center complete with greenhouses, a nursery, and outdoor gardens. When their landlord decided to redevelop the property, the team took it as an opportunity to rethink the company’s retail strategy. “The way that customers shop in person and online has shifted and changed over time,” says Ted Winston, who with his brother, David, inherited the business from their father in the 1980s. Noting that there didn’t seem to be as strong of a demand for a full-service garden center, the duo decided to relocate to The Street Chestnut Hill nearby. “Our hope is to reinvigorate hands-on access to the Winston Flowers brand,” says Ted, noting that hosting interactive events is a key part of the new strategy.

The company specializes in the longest-lasting, highest-quality blooms available each season. / Photo courtesy of Winston Flowers

While maintaining their other retail locations and design studios in New York City and locally in the South End, Ted and David designed the new Chestnut Hill space to accommodate demonstrations and workshops, including flower arranging and container gardening, along with wine tastings. In addition to flowers and plants, the shop will also offer Winston’s newly expanded selection of gourmet gift boxes featuring handmade chocolates, cheeses, wines, and cookies purchased in small quantities from local artisans, including Gräem Nuts and Chocolate in Concord and Mrs. Mekler’s Mercantile in Cohasset.

That gourmet division is a rapidly growing segment of the business, which now seems worlds away from the pushcart operation that the Winston brothers’ grandfather started in 1944. “We’re all really excited about what’s next,” Ted says.

Winston’s gourmet gift boxes change with the seasons. / Photo courtesy of Winston Flowers

Artistic and artisanal, elements often include cookies, candy, and cheese. / Photo courtesy of Winston Flowers

Winston Flowers’s multiple locations include: 31 Central St., Wellesley; 131 Newbury St., Boston; and 33 Boylston St., Chestnut Hill at The Street Chestnut Hill, which is scheduled to open in August.

First published in the print edition of the July 2024 issue with the headline, “Budding Empire.”