Fenway Hotel
Corporate brand
UnclaimedA historic Jazz Age waterfront hotel in Dunedin, Florida, restored and operated as a boutique property.
Last updated August 24, 2026
Overview
Fenway Hotel is a historic waterfront hotel in Dunedin, Florida, whose origins date to a 1924 construction project and whose building was completed in 1927. Designed by architect Herman Everett Wendell, the hotel was conceived during the Florida land-boom era and became one of Dunedin's prominent seasonal hospitality properties. Its scale, architecture, location on the Saint Joseph Sound, and association with early radio broadcasting made it an important local landmark. The original 110-room hotel operated seasonally for much of its early life, serving winter visitors, including affluent guests from the northern United States. In the 1950s it also functioned as a private club. The property hosted a varied group of public figures, politicians, businesspeople, legal figures, and explorers, including Arctic explorer Robert A. Bartlett, who gave a talk about his expeditions at the hotel. The building was also associated with WGHB, identified as the first radio station in Pinellas County. Founded in 1925 and named after developer George H. Bowes, the station later became part of the lineage leading to WFLA. The hotel's hospitality role ended in 1961 when the building became home to Trinity College. After Trinity College moved to Pasco County in 1988, Schiller International University acquired the property in 1991 and retained it until 2005. Subsequent redevelopment proposals sought to preserve the historic structure while adding new accommodation, event, dining, and wellness facilities. A major proposal developed in the late 2000s encountered opposition over traffic and scale, and redevelopment stalled in 2010 amid legal disputes and foreclosure proceedings. On June 13, 2014, the Taoist Tai Chi Society of the USA purchased the property. The organization initially proposed restoring the hotel as part of a broader institutional development that also included town homes on the landward portion of the site. The town-home phase was later withdrawn, and local approvals were amended in 2015. Following public discussion, the project was revised so that more than 100 rooms would continue to serve as a public hotel, while the building would also accommodate the headquarters and related activities of the Taoist Tai Chi Society. Plans included a rooftop terrace and bar intended to add contemporary activity without displacing the building's principal hotel identity. The restored property is associated with Marriott International's Autograph Collection Hotels, a portfolio of independently characterized hotels. Its current positioning combines historic architecture, waterfront setting, boutique accommodation, food and beverage, events, and connections to Dunedin's local cultural and recreational attractions. A related property, Fenway Cottage, was built beside the hotel in 1938 and has historically been used for seasonal rentals. The cottage remains part of the wider Fenway property story, although it is a distinct residential accommodation building rather than a standard hotel room block.
History
Fenway Hotel emerged from the speculative growth of 1920s Florida. Building plans and financing arrangements were secured in 1924, and construction started that year. Financial difficulties interrupted the work, but construction resumed and the hotel was completed in 1927. Architect Herman Everett Wendell, who also designed the Suwannee Hotel in St. Petersburg, Florida, designed the building. Its position beside the Saint Joseph Sound gave it a strong resort identity, while its Jazz Age form made it one of Dunedin's notable architectural landmarks. The original property contained 110 rooms and operated seasonally, reflecting the importance of winter tourism to Florida's early hospitality economy. During the 1950s, the building was used as a private club and attracted a predominantly northern clientele during the winter season. It changed ownership in 1956. The hotel also became part of the region's communications history when WGHB began broadcasting there in 1925. The station, named for developer George H. Bowes, was the first radio station identified with Pinellas County and later became a predecessor of WFLA. Fenway's guest list included figures from politics, law, business, science, and exploration. Among those associated with stays at the hotel were 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. Arctic explorer Robert A. Bartlett also stayed at Fenway and presented a public talk about his journeys. These associations reinforced the building's reputation as a significant local gathering place. The hotel ceased operating in its original role in 1961, when Trinity College occupied the building. Trinity moved to Pasco County in 1988. Schiller International University then acquired the property in 1991 and held it until 2005. The structure's historical importance remained recognized locally; the Tampa Bay Times described it as Dunedin's most historically valuable building. In the 2000s, developers explored ways to restore the historic hotel while expanding its commercial capacity. A proposal developed in 2007 envisioned a 132-room hotel, spa, ballroom, 150-seat restaurant, two independent wings, and extensive landscaping enclosed by a masonry wall. Some residents raised concerns about traffic and the scale of redevelopment, and an earlier, larger concept had already been rejected. By 2010, the project had stalled because of legal disputes and foreclosure proceedings. The Taoist Tai Chi Society of the USA bought Fenway on June 13, 2014, for use as its national headquarters and as a center linked to its parent organization, the Fung Loy Kok Institute of Taoism. Its initial two-phase plan involved restoring the hotel and grounds for institutional purposes and building 27 three-story town homes on the landward half of the approximately 5.2-acre property. The town-home component was later abandoned. The amended plan received approval from the Dunedin City Commission on March 5, 2015. Public feedback subsequently influenced how much of the building the society would occupy. The final concept retained the building primarily as a public hotel, with more than 100 rooms planned for operation under Marriott International's Autograph Collection Hotels brand. The design also included a rooftop terrace and bar. This approach sought to balance preservation, institutional use, and the property's return to hospitality. The adjacent Fenway Cottage, constructed in 1938, forms a related but separate part of the site. It was historically rented seasonally and later acquired by Mainsail in 2016. Together, the hotel and cottage represent Dunedin's transition from early seasonal resort development to heritage-oriented boutique tourism.
- 2016
Fenway Cottage acquired by Mainsail
[1]Mainsail acquired the adjacent Fenway Cottage.
- 2015
Amended development plan approved
[1]Dunedin approved the revised plan after the proposed town-home phase was withdrawn.
- 2014
Taoist Tai Chi Society purchases Fenway
[1]The Taoist Tai Chi Society of the USA acquired the property for headquarters and international-center purposes.
- 1991
Schiller International University acquires the property
[1]Schiller International University purchased Fenway and retained it until 2005.
- 1988
Trinity College relocates
[1]Trinity College moved to Pasco County.
- 1961
Conversion to educational use
[1]The building became home to Trinity College after its seasonal hotel operation ended.
- 1938
Fenway Cottage is built
[1]A separate five-bedroom cottage was constructed beside the hotel, facing the Saint Joseph Sound and Intracoastal Waterway.
- 1927
Hotel construction completed
[1]The 110-room hotel building was completed.
- 1925
WGHB starts broadcasting
[1]WGHB began broadcasting from the hotel and was identified as the first radio station in Pinellas County.
- 1924
Construction begins
[1]Plans and financing were obtained and construction of Fenway Hotel began, although the work later paused because of financing problems.
Products and positioning
Historic waterfront boutique hospitality combining Jazz Age architecture, local Dunedin character, dining, events, and contemporary hotel amenities.
Hotel accommodation · 1927
Fenway Hotel guest rooms
The property's principal offering is historic boutique accommodation in the restored Fenway Hotel building. The development concept retained more than 100 rooms for public hotel use, preserving the building's primary hospitality function while integrating contemporary amenities with its Jazz Age architecture and waterfront setting.
Food and beverage
Rooftop terrace and bar
The restoration concept includes a rooftop terrace and bar designed to provide a contemporary social venue and views associated with the hotel's waterfront location. The feature is intended to add activity to the property while supporting its boutique-hotel positioning.
Hospitality events
Events and meeting spaces
Historic interior spaces and planned ballroom facilities support private functions, meetings, celebrations, and other group events. Event use is part of the property's broader strategy to combine heritage preservation with a commercially active hotel operation.
Vacation rental accommodation · 1938
Fenway Cottage
Fenway Cottage is a separate five-bedroom, four-and-a-half-bath residence built adjacent to the hotel in 1938. It faces the Saint Joseph Sound and the Intracoastal Waterway and was historically rented to seasonal guests. Its layout includes private bathrooms for the first-floor bedrooms and former servants' quarters on the second floor.
Brand decisions
2015
Revision toward a public hotelStrategyBackground
The original development plan included 27 three-story town homes behind the hotel, but the town-home phase was later withdrawn. Public opinion also influenced how much space the society would occupy.
Action taken
The amended plan approved by Dunedin retained more than 100 rooms for public hotel use and incorporated a rooftop terrace and bar.
Aftermath
The revised direction allowed the property to preserve its hotel identity while accommodating the society's institutional needs.
2014
Taoist Tai Chi Society acquisitionM&ABackground
After earlier redevelopment difficulties, the Taoist Tai Chi Society of the USA sought a permanent national headquarters and an international center for its parent organization.
Action taken
The society purchased Fenway Hotel and proposed restoring the building and grounds for institutional use.
Aftermath
The project evolved toward a mixed institutional and public-hotel model, with the hotel remaining the principal use of the historic building.
Purchase price. $2.8 million (June 13, 2014)
2007
Historic hotel expansion proposalStrategyBackground
Redevelopers sought to restore the Jazz Age building while increasing its capacity and adding a spa, ballroom, restaurant, independent wings, and landscaping.
Action taken
A proposal for a 132-room hotel and expanded facilities was developed, but some residents raised traffic concerns and an earlier larger proposal had been rejected.
Aftermath
The redevelopment effort later stalled amid legal disputes and foreclosure proceedings.
Recent events
- 2015
Dunedin approves amended Fenway redevelopment proposal[1]
Regulation
The Dunedin City Commission approved an amended development proposal after the town-home phase was withdrawn and the project was revised following public discussion.
- 2014
Taoist Tai Chi Society of the USA purchases Fenway Hotel[1]
M&A
The Taoist Tai Chi Society of the USA purchased the property for use as its national headquarters and as an international center connected with the Fung Loy Kok Institute of Taoism.
- 2010
Restoration and expansion proposal stalls[1]
Lawsuit · Other
A redevelopment effort involving restoration, additional wings, rooms, a spa, ballroom, restaurant, and landscaping stalled amid legal disputes and foreclosure proceedings.
- 1991
Schiller International University acquires Fenway Hotel[1]
M&A
Schiller International University purchased the property and retained it until 2005.
- 1988
Trinity College leaves the property[1]
Other
Trinity College relocated to Pasco County, ending its use of the Fenway building.
- 1961
Fenway Hotel becomes home to Trinity College[1]
Other
After operating seasonally as a hotel, the property was converted for educational use by Trinity College.
- 1927
Fenway Hotel building is completed[1]
Other
The hotel building was completed after the earlier construction hiatus.
- 1925
WGHB begins broadcasting from Fenway Hotel[1]
Other
WGHB, described as the first radio station in Pinellas County, began broadcasting from the hotel. The station was named after developer George H. Bowes and became a precursor to WFLA.
- 1924
Construction of Fenway Hotel begins after plans and financing are obtained[1]
Other
Construction began in 1924, although financing problems caused an interruption before the building was completed.
Sources1 sources
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