433 N Osprey Ave

Off Market

433 N Osprey Ave

Sarasota FL 34236

2242 sq. ft.

6565 sq. ft.

Single-Family

Last sold for $522,500

Christine del Monte, last sold this property on 23 December 2025 after 276 days on market.

Overview

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.

Features

3 bedrooms

3 bathrooms

2242 sq. ft. floor area

6565 sq. ft. lot size

Single-Family

Estimated Value

Based on this property and similar 3 bedroom single-family properties sold in Sarasota over the last 12 months, the estimated median property value of 433 N Osprey Ave is $1.7m.

Median value

$1.7m

Estimated value range

$522.5k - $7.82m

Median days on market

Estimated value trend

-6%

decrease over the last 12 months

Average days on market is based on recent, comparable sales in Sarasota. It is only an indication of the time a property is actively listed and should not be relied upon as an accurate representation of how soon a property will be sold.

Property history for 433 N Osprey Ave

2025

Sold

$522,500

23 Dec 2025 by Christine del Monte, of COLDWELL BANKER REALTY

2017

Sold

$725,000

08 Mar 2017

Happy sellers in Sarasota

90%

90% of sellers in Sarasota reported that their sale price either exceeded or met their price expectations.

Sarasota stands out for consistently delivering exceptional satisfaction and strong market results for homeowners.

This is based on voluntary sentiment collected from 11 reviews in Sarasota over the last 12 months.

Local market activity for 3 bedroom single-family properties in Sarasota

In the last 12 months, 31 three-bedroom single-family properties similar to 433 N Osprey Ave, have been sold.

This represents a 44% increase in three-bedroom single-family properties sales when compared to the previous 12 months.

Sold

For Sale

Interested in selling?

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Nearby agents

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