433 N Osprey Avenue

Price Drop Alert | Now Under $600K!
Own Sarasota’s Most Talked-About Landmark in Walkable Gillespie Park
Where else can you find a walkable downtown Sarasota parcel with two separate, income-producing structures—each brimming with character and short-term rental potential—for under $600K?
Welcome to The Boathouse and The Lighthouse, a nationally recognized, whimsical compound featured on HGTV’s Zillow Gone Wild and celebrated in multiple media write-ups. This one-of-a-kind property is a magnet for attention and bookings, offering savvy investors and creative buyers a rare chance to own a piece of Sarasota’s circus-inspired charm.
Built in 1933 by master boatbuilder Oliver Blackburn for Captain Arthur Rowe—who worked for both John Ringling and William Selby—this property is steeped in local lore and maritime history. The Boathouse features 2 bedrooms, 2 baths, a spiral staircase, and a private suite with balcony access. The Lighthouse is a vertical 1-bed, 1-bath retreat with three levels and a panoramic observation room perfect for a studio, office, or creative escape.
Why This Property Stands Out:
Two Distinct Structures = Double the rental opportunity
Circus-Themed Sarasota Legacy = Built-in marketing appeal
Walkable Location = Steps to downtown, dining, arts and culture
4.2 Miles to Lido Beach = Beach lifestyle meets city convenience
Short-Term Rental Ready = Just stage it and start earning
Next to a $2M+ New Build = Rising neighborhood values
Whimsical and Quirky Design = Instagrammable, unforgettable stays
Whether you're:
An investor looking for high-performing Airbnb potential
A creative seeking a live/work compound
A history lover drawn to Sarasota’s storied past
This property offers unmatched flexibility, charm, and income potential. Live in one, rent the other—or transform both into a boutique retreat or artistic haven.
Motivated Seller | Bring All Offers
This is more than a home—it’s a legacy waiting for its next chapter. Don’t miss your chance to scoop up one of Sarasota’s most iconic properties at a compelling new price.