Victorian Charm Meets Florida History: The Former Fern Court Bed & Breakfast
Welcome to a true architectural treasure nestled in the heart of San Mateo, Florida. Built in 1889 for Henry B. Bailey, a prominent railroad magnate and citrus broker, this Victorian “Painted Lady” stands as one of the area’s most historically significant homes. Spanning 4,624 square feet, this grand residence sits on two lush acres and offers a rare opportunity to own a piece of Florida’s Gilded Age.
A Storied Past
This home was once known as the Fern Court Bed and Breakfast, a well-known destination that hosted distinguished guests and travelers arriving by the San Mateo Express. Among its most notable guests was Mrs. Theodore Roosevelt, who stayed at the home in 1905, adding to the property’s storied legacy. Bailey, the original owner, played a vital role in the development of San Mateo. His close relationship with Henry Flagler helped extend the Florida East Coast Railway through the region, shaping the community’s future and marking this home as a cornerstone of local history.
Architectural Highlights
Step onto the grand wrap-around front porch, and you’ll immediately sense the charm of a bygone era. Inside, you’ll find:
- Original wood floors with the patina of age
- Stained glass windows casting colorful light into hallways
- Transom windows and wide baseboards throughout
- A cozy library perfect for reading and reflection
- Original mantels above fireplaces that once warmed Victorian parlors
- A screened-in porch ideal for enjoying warm Florida evenings
While some past renovations have altered portions of the home, its historic integrity and architectural beauty remain remarkably intact. With a thoughtful restoration, this residence could be returned to its former glory.
Grand Scale & Endless Possibilities
This is a big home with big potential. Offering seven bedrooms, nine bathrooms, and even a hidden room, this property provides endless options for creative reimagining—whether as a bed and breakfast, a multi-generational home, or a private estate.
The yard is massive, providing ample room for gardens, entertaining, or future additions. Towering trees and open space create a tranquil, park-like setting around the home.
A Unique Opportunity
Offered at $399,000, this landmark property is a rare find in today’s market. With deep historical roots, stunning Victorian architecture, and a prestigious past, the former Fern Court Bed and Breakfast invites you to become the next chapter in its legacy.
Whether you’re a lover of old homes, a history enthusiast, or an investor with vision, this remarkable property is your chance to own a living piece of Florida’s past—and its future.
