In a sea of stucco and symmetry, 433 N Osprey Avenue stands out like a technicolor buoy — and soon, the rest of the country will get a good look at it.
The Boathouse and Lighthouse, a pair of wildly unique residences located just blocks from downtown Sarasota, are set to appear on Zillow Gone Wild, HGTV’s hit show that celebrates the quirkiest real estate listings in America.
Airing Friday, August 1st, the episode will give viewers a tour of this one-of-a-kind compound, which includes a boat-shaped house and a freestanding lighthouse-style tower — each designed to be fully livable and fully unforgettable.
A Sarasota listing unlike anything else that’s on the market today
Built in the 1930s by master boat builder Oliver Blackburn, the HGTV-featured property fuses local history, eccentric architecture, and unmistakable charm. And its unique design has been capturing people’s eyes for over 50 years, as evidenced by this New York Times interview with the home’s owner that dates back all the way to the early 1970s.
Now on the market for $795,000, the listing offers a rare opportunity for creatives, investors, or anyone with a love of the offbeat. From its rooftop views to its spiral staircases and retro color palette, every corner is packed with personality. And potential!
At a glance: a two-for-one historic property with income potential
Listed with Christine del Monte of Coldwell Banker Realty, the $795K property includes two separate dwellings: a two-bedroom, two-bath Boathouse and a one-bedroom, one-bath Lighthouse.
Both are currently operating as successful short-term rentals and are located just five blocks from downtown Sarasota and 4.2 miles from Lido Beach.
Set on a lushly landscaped lot in the Gillespie Park neighborhood, the property’s central location makes it an ideal setup for vacation rentals, a live/work compound, or a private artistic retreat. Each structure has its own entrance and private features, offering flexibility for future owners.
The Boathouse: 2BR, 2BA, and a whole lot of character
Built to resemble a boat moored on land, the two-story Boathouse is the larger of the two structures. Its quirky footprint includes a bright living room, updated kitchen, and whimsical detailing throughout — including porthole windows and a spiral staircase leading to a second-floor suite with private balcony access.
Nautical themes meet homey comfort in a way that makes this place as fun as it is functional.
The Lighthouse: 1BR, 1BA, and rooftop views for days
The freestanding Lighthouse is a vertical 1-bedroom residence with three stacked levels, topped by an observation room that could be used as a creative studio, workspace, or reading nook with a view.
With its curved lines and distinctive profile, this structure doubles as a local landmark and a surprisingly efficient living space.
Historic roots with Ringling ties
Beyond its visual flair, the property has a rich local history. It was built in 1933 by Oliver Blackburn for Arthur Rowe, a former yacht captain to John Ringling and William Selby — two towering figures in Sarasota’s development.
“Dad was the captain of John Ringling’s yacht from 1910 until World War I,” Rowe explained to the New York Times in his 1971 interview. “After his stint with the circus entrepreneur, he took time out for the war, then skippered the yacht owned by William Selby of the Selby Foundation until World War II.”
That backstory gives the home a connection to the city’s circus-era golden age, adding a layer of historical charm that’s hard to replicate.
Ideal location near beaches, parks, and the arts
The compound’s Gillespie Park location puts it within walking distance of Sarasota’s downtown shops, restaurants, and waterfront. The Bay Park, Sarasota Opera House, and Marie Selby Botanical Gardens are all a short drive away.
For beachgoers, Lido Beach and Siesta Key offer turquoise waters and powdery sand just minutes from the front door.
AirBnB goldmine or one-of-a-kind creative compound?
Whether you’re looking to generate short-term rental income or searching for an inspiring place to live and work, this property checks both boxes. Live in one structure and rent the other, keep both operating as high-performing AirBnBs, or dream up something new entirely.
With its imaginative architecture, central location, and upcoming national exposure on HGTV, 433 N Osprey Avenue is ready for its next chapter — and for someone bold enough to write it.
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The post Quirky $795K boathouse and lighthouse duo in Sarasota to star in this week’s ‘Zillow Gone Wild’ appeared first on Fancy Pants Homes.
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