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North of Mount Dora, SR 44 leaves US 441, which curves south towards Orlando and Miami. SR 44 turns north then narrows from four lanes to two lanes before it curves between Lake Joanna and Loch Leven before passing by the Mid Florida Air Service Airport in Eustis. From there the road turns right onto East Orange Avenue, which continues Route 44 ...
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In Leesburg, SR 44 leaves US 441 heading toward Wildwood, Inverness, and Crystal River, while US 441 curves to the northwest, then intersects U.S. Route 27 in another concurrency, and as a result, the hidden state routes are officially SR 25-500. The concurrency with SR 25 is short-lived, because in Lady Lake, SR 25 branches away as County Road 25.
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One-way street, inbound access only; SR 44 west traffic joins SR 273 north traffic along Pine Street north: L0.17R: SR 273 south (Tehama Street west / Historic US 99) East end of SR 273 / Historic US 99 overlap; SR 44 east traffic splits onto Tehama Street east: L0.31L– L0.38R: Liberty Street
A fatal crash that killed two people in their 80s was caused when a truck turned off of Paradise Bay Road onto Highway 104.