The Fascinating Story Behind the Sears & Roebuck Founder’s Vintage Florida Home

A charming Craftsman-style home in Gulfport, Florida, just found a buyer days after being listed for $600,000. This isn’t just any house—it’s the work of Alvah Roebuck, the Sears & Roebuck founder himself. Built in 1925, the place sits among the colorful cottages and creative energy that define Gulfport, a coastal town where artists and free spirits have always felt at home.

Step inside, and you’ll see the old and new living side by side. Original details from a century ago—hardwood floors, crown molding, tall windows—still shine, blending seamlessly with modern updates in the kitchen and bathrooms. It’s not a huge house, just three bedrooms and two-and-a-half baths packed into 1,536 square feet, but it feels open and bright. Rooms connect easily. There’s a sense of flow, of warmth, that’s hard to miss.

Roebuck’s story adds another layer. Born in Indiana, Alva left the company after Sears bought him out for $20,000 in 1895 and headed south for Florida. He built his dream home here, mixing Craftsman style with Colonial Revival touches. But the 1929 crash hit hard. Roebuck lost much of his fortune and ended up returning to the very business that made his name.

His influence on American homes is still felt, thanks to those famous Sears kit houses that started selling in 1908. Even though he was no longer with the company when they launched, his name remained on every catalog. In Florida, his legacy lives on through this home—a piece of history that is a truly remarkable example of craftsmanship and design.

Walk outside and you’re surrounded by brick streets and echoes of the 1920s. The home stands in Gulfport’s historic district, close enough to stroll down to the bay or wander a few blocks to the lively Gulfport Art District. Here, more than 20 restaurants, live music, dancing, and cozy cafés draw both locals and visitors. On Tuesdays, Beach Drive transforms for the outdoor fresh market, where local produce and crafts fill the street.

Roebuck picked Gulfport as his retirement spot, and you can still feel that personal touch—the kind you can’t fake. Nearly 100 years after Roebuck built it, this Gulfport retreat feels as inviting and full of character as ever—a fitting tribute to the man behind it.