433 N Osprey Ave

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  • 3 Beds
  • 3 Baths
  • 1949 SqFt

Under contract-accepting backup offers. Price Drop Alert | Now Under $600K! Own Sarasota's Most Talked-About Landmark in Walkable Gillespie ParkWhere 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 opportunityCircus-Themed Sarasota Legacy. Built-in marketing appealWalkable Location,Steps to downtown, dining, arts & culture4.2 Miles to Lido Beach = Beach lifestyle meets city convenienceShort-Term Rental Ready;Just stage it and start earningNext to a $2M+ New Build = Rising neighborhood valuesWhimsical & Quirky Design; Instagrammable, unforgettable staysWhether you're:An investor looking for high-performing Airbnb potentialA creative seeking a live/work compoundA history lover drawn to Sarasota's storied pastThis 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 OffersThis 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.

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Amenities

Interior Layout

  • Solid Surface Counters
  • Thermostat

Exterior Features

  • French Doors

Schools

  • Alta Vista Elementary
  • Booker High