433 N Osprey Avenue, Sarasota, FL 34236
Local realty services provided by:Tomlin St Cyr Real Estate Services ERA Powered
433 N Osprey Avenue,Sarasota, FL 34236
$522,500
- 3 Beds
- 3 Baths
- - sq. ft.
- Single family
- Sold
Listed by: christine del monte
Office: coldwell banker realty
MLS#:A4644435
Source:MFRMLS
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Price summary
- Price:$522,500
About this home
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 & 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 & 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 & 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.
Contact an agent
Home facts
- Year built:1935
- Listing ID #:A4644435
- Added:287 day(s) ago
- Updated:January 03, 2026 at 07:57 AM
Rooms and interior
- Bedrooms:3
- Total bathrooms:3
- Full bathrooms:3
Heating and cooling
- Cooling:Central Air
- Heating:Central, Electric
Structure and exterior
- Roof:Membrane
- Year built:1935
Schools
- High school:Booker High
- Middle school:Booker Middle
- Elementary school:Alta Vista Elementary
Utilities
- Water:Public, Water Connected
- Sewer:Public Sewer, Sewer Connected
Finances and disclosures
- Price:$522,500
- Tax amount:$4,949 (2024)
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