The hotel operated seasonally until 1961 when it became home to Trinity College. In 1988, Trinity College moved to Pasco County. In 1991, Schiller International University purchased the property and kept it until 2005.
The Tampa Bay Times called the hotel building Dunedin's "most historically valuable structure". Herman Everett Wendell, who also designed the Suwannee Hotel (a landmark that was lost to development), was the building's architect.
The 110-room hotel was home to radio station WGHB, the first in Pinellas County, which began broadcasting in 1925.  The station was named after developer George H. Bowes, and was the precursor to WFLA. 
Guests included Harley M. Kilgore, Kenesaw Mountain Landis, Stephen Early, Alfred M. Landon, Charles Kettering, Clarence Darrow, Alanson B. Houghton, James H. McGill and J.M. Donaldson. Robert A. Bartlett, an arctic explorer, stayed at the hotel and presented a talk on his journeys.
As a private club in the 1950s, the hotel hosted an exclusive clientele of mostly Northerners during the winter months, changing owners in 1956 when it was bought for $300,000.
Plans to restore the hotel and add two independent wings to the building, creating "a hotel with 132 rooms, a spa, a ballroom and a 150-seat restaurant, all surrounded by lush landscaping and a 6-foot-tall masonry wall", developed in 2007, raising traffic concerns from some residents. An earlier plan for a larger redevelopment was rejected. Redevelopment of the Jazz Age hotel stalled in 2010 over legal disputes and a foreclosure proceeding.
On June 13, 2014, the Taoist Tai Chi Society of the USA purchased the hotel for $2.8M to become its new national headquarters and a new international centre for its parent society, the Fung Loy Kok Institute of Taoism.     The Society had proposed a two-phase development, renovation and restoration of the hotel building and grounds to suit the Society`s purposes, then construction of 27 three-story town homes behind the hotel on the landward half of the 5.2 acre property, but later withdrew the town homes phase. The amended development proposal was approved by the Dunedin City Commission on March 5, 2015. 
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- "Dunedin hotel changes hands". The Evening Independent. August 1, 1925. Retrieved February 13, 2012.
- Hill, Norma Jean (August 23, 1956). "Fenway at Dunedin sold for more than $300,000". St. Petersburg Times. Retrieved February 13, 2012.
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- El-Khoury, Tamara (May 17, 2007). "Developer scales back project". St. Petersburg Times. Retrieved February 13, 2012.
- Harwell, Drew (February 10, 2010). "Developer for Fenway hotel in Dunedin hit with foreclosure lawsuit". Tampa Bay Times. Retrieved February 13, 2012.
- "Taoist Tai Chi Society to Locate National Headquarters and International Conference Center in Tampa Bay Area". Herald Online. June 13, 2014. Retrieved June 13, 2014.
- Frago, Charlie (June 13, 2014). "Fenway Hotel bought by Tai Chi nonprofit for $2.8 million". Tampa Bay Times. Retrieved June 17, 2014.
- Summers, Keyonna (September 3, 2014). "Taoist group's renovation of Dunedin's Fenway Hotel to include townhomes". Tampa Bay Times. Retrieved 28 March 2015.
- "Tai Chi Society's plans for Fenway look promising". Tampa Bay Times. September 11, 2014.
- "Dunedin Commission Meeting". City of Dunedin. Retrieved 29 March 2015.