BOSTON–Two of Boston’s largest publicly traded companies are preparing for significant headquarters relocations, with both moves expected to reshape the city’s corporate landscape in 2027.
According to reporting by the Boston Business Journal (BBJ), DraftKings will relocate from Back Bay to downtown’s Post Office Square, while Wayfair will consolidate its headquarters into the Boylston Street tower DraftKings will vacate.
DraftKings Returning to Downtown, as Reported by BBJ
DraftKings (Nasdaq: DKNG) will move its headquarters to 225 Franklin St., a 32-story tower owned by Oxford Properties. As reported by BBJ, the move marks a return to downtown for the sports gaming giant, which operated at 125 Summer St. before relocating to Back Bay in 2014. The company said the new space will support a “modern, flexible work environment” with improved amenities and central access for employees.
DraftKings has expanded rapidly alongside the national surge in legalized sports betting. According to BBJ, the company most recently leased 125,000 square feet through 2029 and continues to outgrow its existing footprint.
Wayfair Consolidates Into 500 Boylston St., According to BBJ
Wayfair (NYSE: W) will take over the headquarters space at 500 Boylston St. and its connected 222 Berkeley St. building. The e-commerce retailer, which previously occupied more than 1.3 million square feet across multiple Back Bay properties, will consolidate operations into a long-term lease that keeps the company in the neighborhood. As reported by BBJ, Wayfair has been reducing its office footprint in recent years amid challenges in the competitive online retail sector.
Oxford Properties, which owns both 225 Franklin St. and 500 Boylston/222 Berkeley, said the two moves demonstrate strong, sustained commitments from both companies to the city of Boston. The Boylston Street building has recently added new retail anchors including Trader Joe’s, Starbucks, and the Cactus Club Cafe.
A Significant Shift in Boston’s Office Market
According to the Boston Business Journal, the DraftKings and Wayfair relocations represent some of the most impactful headquarters moves announced this year. The deals were first reported by Banker & Tradesman.
Oxford Properties currently markets approximately 117,000 square feet of available space at 225 Franklin St. and roughly 44,000 square feet at 500 Boylston St., positioning both properties to remain key assets in Boston’s evolving commercial real estate market.
Wayfair reported revenues below $12 billion last year amid restructuring, while DraftKings continues strong growth, reporting nearly $4.8 billion in revenue.
Both companies expect their new headquarters to support long-term talent attraction, workplace modernization, and strategic growth—moves that will keep them firmly rooted in Boston’s economic and innovation ecosystem.
