99 High St. (center) looks out over Dewy Square in front of Boston's South Station and the Rose Kennedy Greenway. Photo courtesy of Synergy Investments
Synergy Investments is the new owner of 99 High St., a prominent office building on Boston’s Rose Kennedy Greenway and a building many in the real estate industry saw as a key indicator of where downtown office building values are headed.
A deed filed today in the Suffolk Registry of Deeds shows an affiliate of Synergy paid an affiliate of pension giant TIAA’s Nuveen real estate arm $227 million for the 32-story tower. City assessing records peg the 1971-vintage building at 801,343 square feet.
The Thursday sale’s price per square foot of $283.27 ‘s 18.7 percent less than the most recent mortgage on the building, from September of last year.
“The addition of 99 High Street to our portfolio solidifies Synergy’s prominence as one of Downtown Boston’s premier owners and operators,” David Greaney, founder and CEO Of Synergy, said in a statement. “Synergy will continue to invest in high-quality assets in prime locations across the city.”
In the last two years, Synergy has also bought the 101 Arch St. and 179 Lincoln St. office buildings in downtown Boston, both at a discount off their pre-COVID prices.
Unlike other recent high-profile office sales downtown, 99 High St. is relatively highly occupied. The property is currently 78 percent leased to 32 tenants, including Mercer, Marsh McLennan, AIG and Karuna Therapeutics, Synergy said in its announcement of the deal, adding that leasing activity has been “robust” at the building this year.
Boston’s availability rate declined 0.5 percent in the first quarter of 2025 to 22.7 percent, including an 18.1 percent direct vacancy rate, Avison Young reported. It marks the third straight quarter of declines – albeit small – in the overall vacancy rate.
The Boston Globe first reported the deal, adding that Synergy is assuming the remaining balance on the mortgage from insurance giant MetLife’s real estate lending arm.
Nuveen acquired the property for $273 million in 2005, just as the removal of the elevated Central Artery upgraded tenants’ views to the new Rose Kennedy Greenway.
The existing mortgage was issued by MetLife for $277 million in 2018 and upgraded to $279.2 million in September. MetLife subsequently forgave $50 million of the debt, according to Suffolk County Registry of Deeds documents.
Nuveen placed the property on the market last year and hired CBRE to recruit potential buyers.
Originally completed in 1971, 99 High St. was most recently renovated in 2020 with designs by local architecture firm SGA. Nuveen updated the lobby, facade and entry areas in a project estimated at $7.5 million. The main entrance was also relocated to the corner of Congress and High streets, creating an additional ground-floor retail space.
Industry sources say the previous owners had consulted architecture firms about the possibility of a residential conversion, but it’s not clear if Synergy will pursue those plans or keep the building as a purely office building.
