Winston Flowers
A family-owned luxury florist providing flower delivery, floral gifts, corporate services, and event design.
Last updated October 14, 2026
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Overview
Winston Flowers is a third-generation, family-owned floral retailer based in Boston, Massachusetts. It began in 1944 when Robert Winston and his teenage son, Maynard Winston, operated a flower pushcart outside Boston's original Ritz-Carlton hotel near Arlington Street and Newbury Street. The business later established its first permanent retail shop at 131 Newbury Street in the late 1950s, a location that remains associated with the company. Maynard Winston took control after Robert Winston's death in 1970 and is credited with developing the company's modern sourcing and retail model. During the 1970s, he formed relationships with local farms and international growers, including suppliers in the Netherlands, Italy, France, and Ecuador. The business expanded its range beyond conventional bouquets to include distinctive seasonal flowers, plants, and higher-end floral designs. A Boylston Street shop focused on green plants opened in 1975, followed by a Chestnut Hill Mall location in the early 1980s. David and Ted Winston, Maynard's sons, took over leadership in 1988, continuing the family's direct involvement and making Winston Flowers a three-generation enterprise. Under their leadership, the company invested in operational infrastructure, technology, design capacity, delivery, and customer-service systems. Computers were introduced into workplace operations in 1990, and the company established a larger South End facility for design, delivery, and client services. It subsequently acquired a much larger industrial property on Southampton Street in stages during 1992 and 1993 to serve as its headquarters. Winston Flowers operates as a high-end florist rather than solely as a traditional neighborhood flower shop. Its offerings include seasonal floral collections, roses, sympathy arrangements, baby baskets, plants, gourmet gifts, subscriptions, corporate floral programs, residential services, holiday décor, weddings, and other special events. Its gift collections are refreshed throughout the year around seasonal and gifting occasions, including Valentine's Day, Mother's Day, autumn, and the holiday period. Designs are generally presented in vessels or containers sourced internationally. Mother's Day is identified as the company's busiest floral holiday, followed by Valentine's Day. The company emphasizes freshness, longevity, color, and visual design in product selection. It works with local growers whenever possible; in late summer and early fall, a substantial share of its flowers may come from New England and New York suppliers. Some farms grow flowers specifically for Winston Flowers, while specialty varieties are imported from overseas growing regions. Imported flowers are transported by commercial airlines, with much international product entering through New York's John F. Kennedy International Airport. The retail network has included locations in Boston, Chestnut Hill, Wellesley, Hingham, Concord, and Greenwich, Connecticut. The company currently describes four Massachusetts retail shops and one in Greenwich, Connecticut, while several earlier locations have closed. Its operating reach expanded significantly in New York in 2018 with a 12,000-square-foot design studio in Long Island City and the acquisition of Manhattan florist Surroundings. The company followed that move with the 2019 acquisition of the high-end New York florist L'Olivier. Its own studios provide daily delivery in core metropolitan areas, while a partner-florist network supports delivery across the continental United States. Winston Flowers also operates a philanthropic program, Charity in Bloom, through which a portion of the purchase price of selected custom-designed arrangements is donated to nonprofit organizations. The initiative has supported organizations concerned with health, medical research, food access, youth development, and mentorship. Overall, the brand is positioned around luxury floral design, personalized service, freshness, regional and international sourcing, and family continuity.
History
Winston Flowers was founded in 1944 by Robert Winston and his teenage son, Maynard Winston, initially as a flower pushcart positioned outside Boston's original Ritz-Carlton hotel. The family later opened a permanent store at 131 Newbury Street in the late 1950s. The Winstons lived above the shop, making the original retail location both a business premises and a family home. After Robert Winston died, Maynard assumed control in 1970. His tenure shaped the company's sourcing philosophy and expansion. He developed relationships with local farmers and international growers, introducing a broader selection of flowers and building supplier relationships that in some cases lasted for decades. In 1975, the company opened a Boylston Street shop oriented toward green plants. A store at Chestnut Hill Mall followed in the early 1980s. David and Ted Winston, Maynard's sons, succeeded him in 1988. Their leadership represented the third generation of Winstons to operate the company. They expanded the business beyond retail bouquets into seasonal gift collections, corporate accounts, residential floral services, wedding and special-event design, holiday décor, subscriptions, plants, and gourmet gifts. Operational modernization began in 1990 with the introduction of computers into the workplace. That year, Winston Flowers also purchased an 8,000-square-foot building on Malden Street in Boston's South End for design, delivery, and client-services functions. As the company outgrew that facility, it acquired a 75,000-square-foot industrial building on Southampton Street in stages during 1992 and 1993. The property became the company's headquarters and supported larger-scale design and delivery operations. From 2000 through 2012, Winston Flowers opened or operated additional locations in Boston, Chestnut Hill, Wellesley, Hingham, Concord, and Greenwich, Connecticut. Some of these sites were later closed. The company launched its philanthropic Charity in Bloom program in 2010, using custom floral arrangements to direct a portion of sales to nonprofit organizations. The initiative began with Perkins School for the Blind and subsequently supported organizations in areas including medical research, food access, youth programs, and mentorship. The company expanded into New York in 2018. It opened a 12,000-square-foot design studio in Long Island City for New York design and delivery teams and acquired Manhattan florist Surroundings. This move allowed Winston Flowers to provide same-day service in Manhattan while extending its direct reach to Fairfield County and Westchester County. In 2019, the company acquired another high-end New York florist, L'Olivier. Winston Flowers' present model combines a limited network of company retail shops with dedicated design studios and a national partner-florist network. Its direct delivery areas include Greater Boston, New York City, Fairfield County, and Westchester County, while partner florists support orders across the continental United States. Product sourcing combines New England and New York growers with specialist overseas suppliers. The company continues to present itself as a luxury, service-oriented florist with a strong emphasis on design, freshness, seasonal merchandising, and family ownership.
- 2019
L'Olivier acquisition
[1]The company acquires the high-end New York florist L'Olivier.
- 2018
New York design studio opens
[1]A Long Island City design and delivery studio opens alongside the acquisition of Manhattan florist Surroundings.
- 2010
Charity in Bloom launches
[1]The company introduces a recurring philanthropic program that directs part of the price of selected floral arrangements to nonprofit partners.
- 1992
Southampton Street headquarters expansion
[1]Winston Flowers begins acquiring a larger industrial property on Southampton Street, completing the purchase in stages through 1993.
- 1990
Operations are computerized
[1]The company introduces computers into workplace operations and purchases a South End building for design, delivery, and client services.
- 1988
Third-generation leadership
[1]Maynard Winston's sons, David and Ted, assume leadership of the company.
- 1975
Boylston Street plant shop opens
[1]Winston Flowers opens a Boylston Street location focused on green plants.
- 1970
Maynard Winston takes over
[1]Following Robert Winston's death, Maynard Winston assumes control and begins a period of sourcing and retail development.
- 1950
First permanent Newbury Street shop
[1]The company opens its first permanent retail location at 131 Newbury Street in the late 1950s.
- 1944
Business begins as a Boston flower pushcart
[1]Robert Winston and his son Maynard start the business with a floral pushcart outside Boston's original Ritz-Carlton hotel.
Products and positioning
Luxury, design-led floral retailer combining family ownership, local and international sourcing, metropolitan delivery, and event services.
Floral gifts
Seasonal floral collections
Winston Flowers refreshes its principal gift collections throughout the year around seasonal and occasion-based moments such as winter, Valentine's Day, spring, Mother's Day, summer, autumn, and the holidays. The collections are designed as ready-to-order arrangements and are generally presented in decorative vessels or containers. They form the core of the brand's premium consumer offering and are supported by local and international flower sourcing.
Premium floral arrangements
Luxe Collection
The Luxe Collection is a permanent premium range built around more elaborate floral presentations and upscale gifting. It complements the seasonal collections and expresses Winston Flowers' high-end positioning through distinctive flower selection, design treatment, and presentation vessels. Specific arrangements vary over time and are offered through the company's retail and delivery channels.
Plants · 1975
Plant Collection
The Plant Collection extends the brand beyond cut flowers with potted and decorative greenery. Plants became an important part of the business during Maynard Winston's expansion, including the 1975 Boylston Street shop focused on green plants. The collection serves ongoing home, office, and gifting needs and is distinct from the company's seasonal cut-flower ranges.
Gourmet gifts
Gourmet Collection
The Gourmet Collection adds food and specialty gift products to floral orders. It is intended for customers seeking a broader gift presentation rather than flowers alone and can be paired with arrangements for seasonal, corporate, and personal occasions. The collection is part of the company's broader strategy of combining flowers with premium gifting.
Permanent occasion collections
Sympathy, Roses, and Baby Baskets
These permanent collections address recurring gifting occasions and needs. Sympathy products are designed for condolence and memorial settings, roses provide a dedicated category for a widely requested flower type, and baby baskets serve birth and family celebrations. Their continuing availability gives the retailer stable occasion-based offerings alongside its frequently changing seasonal ranges.
Floral delivery service
Subscriptions
Weekly and monthly subscriptions provide recurring floral delivery for homes, offices, and ongoing gifting. Subscription service supports Winston Flowers' relationship-based luxury positioning by turning individual purchases into continuing delivery arrangements. Designs and flower selections can vary by season and availability, using the company's local and international sourcing network.
Professional floral services
Corporate, wedding, and event floral design
The company's professional services cover corporate accounts, residential floral programs, weddings, special events, and holiday décor. These services extend beyond catalog ordering into consultation, custom design, installation, and scheduled delivery. Design studios in Boston and Long Island City support larger projects and metropolitan fulfillment.
Marketing campaigns
- 2010Charity in Bloom
Boston · New York · United States
Charity in Bloom is Winston Flowers' philanthropic platform. Each month, the company offers a custom-designed arrangement connected to a nonprofit partner and donates 20 percent of the purchase price. The program began with Perkins School for the Blind and has included organizations such as the Breast Cancer Research Foundation, Greater Boston Food Bank, City Harvest, Boys & Girls Clubs of Boston, and Madison Square Boys & Girls Clubs.
Outcome. The initiative created a recurring mechanism for linking floral purchases with nonprofit fundraising across the company's core metropolitan markets.
Brand decisions
2019
Acquire L'OlivierM&ABackground
After establishing a dedicated New York studio and acquiring Surroundings, Winston Flowers continued consolidating and expanding its presence in the New York luxury-florist market.
Action taken
The company acquired high-end New York florist L'Olivier.
Aftermath
The acquisition further strengthened Winston Flowers' New York presence, although the available reference material does not provide transaction terms or later operating details.
2018
Expand direct New York operationsM&ABackground
Winston Flowers sought to extend its delivery and design capabilities beyond Greater Boston into New York City and adjacent Connecticut and New York markets.
Action taken
The company opened a 12,000-square-foot design studio in Long Island City and acquired Manhattan florist Surroundings.
Aftermath
The studio housed New York design and delivery teams and enabled same-day service in Manhattan, while the broader network continued to support additional regional and national orders.
Sources2 sources
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