433 N Osprey Avenue Sarasota, FL 34236

Price Improvement | Own a Sarasota Landmark in Gillespie Park
Now offered at a compelling new price, this one-of-a-kind property—The Boathouse & The Lighthouse—is a rare opportunity to own a nationally recognized architectural gem in Sarasota’s walkable Gillespie Park neighborhood. Featured on HGTV’s Zillow Gone Wild, this iconic compound blends history, artistry, and income potential in a way few properties across the country can match.
Built in 1933 by master boatbuilder Oliver Blackburn for Captain Arthur Rowe—who served both John Ringling and William Selby—this property is a tribute to Sarasota’s maritime legacy. The Boathouse and Lighthouse were designed as a land-based accomodation between a houseboat and a traditional home, and today they stand as a testament to creative living and historic preservation.
The Boathouse offers 2 bedrooms, 2 baths, sunlit living spaces, a modern kitchen, and a spiral staircase leading to a private suite with balcony access.
The Lighthouse is a vertical 1-bedroom, 1-bath retreat with three levels, including a panoramic observation room ideal for a studio, office, or creative escape.
Set on a lushly landscaped lot, this property is the only available parcel in Gillespie Park, a neighborhood experiencing rapid transformation with new luxury homes—including a $2M+ build next door—raising values and expanding downtown Sarasota’s footprint northward.
Whether you're:
An investor seeking high-performing short-term rentals
A visionary looking for a live/work compound
A history lover drawn to Sarasota’s storied past
This property offers unmatched flexibility and character. Live in one, rent the other, or reimagine both as a boutique retreat or artistic haven. With its central location just blocks from downtown Sarasota’s dining, arts, and waterfront, and only 4.2 miles to Lido Beach, this is more than a home—it’s a legacy.
Bring all offers. The seller is motivated, and this iconic residence is ready for its next chapter