The original house that is today known as the Herlong Mansion was originally a simple "cracker style" pine farm home built circa 1845. It was a two-story affair with a detached kitchen built by the Simonton family, one of the original settlers of Micanopy. The site of the mansion was along an Indian trading route, now known as Cholokka Boulevard. After its construction, the pine farmhouse came into the possession of Natalie Simonton, who married Zeddy Clarence ("ZC") Herlong in 1910. ZC was a young and prosperous entrepreneur whose lumber mills, railroad, cattle, citrus and farming operations generated the wealth necessary to remodel the once humble farm house in the grand style of the mansion today.

Together, Mr. Zetty & Mrs. Natalie Herlong created the Greek Revival Mansion over the old home to make a home for their family in the style to which they were accustomed. In 1910, the original structure was “encased within a brick classic revival imitation of a Southern colonial design.” Natalie Herlong maintained title to the property, and when she passed away in 1950, she left the Herlong Mansion to her six children equally, with the understanding that their father could live there until his death. He was to live for another ten years, during which time the mansion fell into disrepair. When old Mr. Herlong died, all of the six siblings wanted the Mansion. What followed was eighteen years of family feuding.

In 2000, the Herlong was under another change of ownership until 2003. The current innkeepers, Linda Barrett and Mark Gregg purchased the mansion in 2003 and have upgraded the mansion and its grounds while remaining ever faithful to its impressive architecture. Today, the Herlong Mansion is one of the most popular retreats in the area, and is open year round as a bed and breakfast. Still retaining its Victorian beauty, it has six beautifully decorated guest rooms, three suites, and three charming cottages.

The Carriage House once sheltered the Herlong's horses and the Pump House housed the original pump and generator. The pump was used to pump water from the well up to the water tower (also still standing). The water tower was connected to the mansion by a pipe that gravity fed water to the mansion. Therefore, the Herlongs benefited from electricity and pressurized indoor plumbing long before "modern" electric service became available to the town of Micanopy in 1938. Listed on the National Register of Historic Places, The Herlong is set back from the street and is surrounded by a lovely garden with statuesque old oak and pecan trees. The Innkeepers meticulously maintain the grounds, filled with azaleas and roses which bloom nearly year-round in the warm weather of North Central Florida. The Herlong is part of the small community of Micanopy which houses antique shops, eateries, a cozy ambiance, and a warm Southern hospitality befitting this stately home away from home.