We are proud to exclusively market for sale Harbor Inn on Main, a rare generational asset located in the heart of one of America's most celebrated small towns. With 155 feet of frontage on vibrant Main Streetrecently ranked #10 Best Main Street in the U.S. and #5 Best Small Town in the South by USA Todaythis mixed use property offers unmatched charm, versatility, and income potential. Built in 1918 and meticulously maintained, the property features 9,605 SF under roof and 2,599 SF of balcony space. Zoned Main Street Marketplace (MSM), this historic gem supports a wide variety of permitted uses including retail, multi family, office, hospitality, and entertainment. Currently operating as a hybrid LTR/STR top rated Airbnb Superhost with (8) turnkey apartment units(6) one bedrooms and (2) studioseach with full kitchens and baths. This income generating property is perfect for investors or owner occupiers. An opportunity also exists to expand with a 9th additional unit or owner/managers suite. The ground floor retail space is elevated above street level and flooded with natural light, offering excellent visibility and a welcoming Main Street presence. Total retail square footage is equal to 2,983 SF and is currently rented month to month offering flexibility for an owner operator to occupy or generate longer term income. Recent capital improvements include a new roof (2020) on the primary building and new HVAC with ductwork (2023) in the retail space. Additional highlights: 14 private parking spaces, Garage/storage space, Located in Flood Zone X, Just blocks from the iconic Safety Harbor Spa, Two majestic Great Oaks on site, Steps away from the lively Third Friday Street Festivala monthly downtown celebration of music, art, food, and community. This is more than a propertyits a piece of Safety Harbor history with modern upside. Contact us today for details or to schedule a private tour.