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Maybe it makes sense that a city founded by Ransom E. Olds, of Oldsmobile automobile fame, was until recently mostly thought of as a place you had to drive through to get somewhere else. Indeed, for decades Oldsmar was best known for its huge flea market and the nearby Tampa Bay Downs horse track. But local boosters wised up in recent years, recognizing that the city’s strategic location at the top of Tampa Bay and on Pinellas County’s border with Hillsborough County made it a desirable relocation destination for business, manufacturing and industry.

And even as road widening made the trip through the center of Oldsmar faster, motorists started finding more reasons to slow down and stop. One of the region’s largest movie houses, AMC Woodlands 20, is located here and a variety of retailers have put down roots. Oldsmar is two distinct communities in many ways. The southern part, tucked between Tampa Road and Old Tampa Bay, is the portion founded by R.E. Olds.

But many of the modest older homes that sit on the city’s long shoreline on the top of Tampa Bay are being demolished and replaced with pricey mansions and several master-planned communities are under way.

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