How about FL 44 in New Smyrna Beach, FL? It has a mainline and a Business route, but both go through the city's downtown area. The east end of Business SR 44 is in the business district where its parent comes in and takes over.
Then FL 44 itself is an oddity as it goes completely across the Florida Penisula what usually even number routes ending in "0" do. Plus, it is signed as two segments, but it is silently multiplexed with US 441 from Leesburg to Mt. Dora and has a Lake County Route 44 from East of Leesburg to FL 19 in Eustis.
FL A1A is one as it is in many segments all, but two that actually loop back to US 1. Plus it has two letters in its designation. To avoid an actual SR 1 to confuse with US 1, FDOT decided to call it A-1-A instead as trying to keep a grid similar to the US numbering scheme by having the lowest odd number to the east.
Then FL 535 is called a "State Road" in Lake Buena Vista, FL even where Orange County maintains it. Usually all FL highways are shielded with blue and gold county route markers where FDOT is not maintaining it. Here you will find FL 535 shields from I-4 to Winter Garden- Vineland Road where State Maintainence ends at I-4 and has a small black on white sign to inform motorists there. FL 527 is that in Downtown Orlando, but city maintained and FDOT does let Orlando keep the road signed as SR 527.
FL 527 in Orlando, is not signed along NB Rosalind Avenue where SB FL 527 is Orange Avenue. On US 17, US 92, and FL 50 (Colonial Drive) there is no NB FL 527 shield at Magnolia Avenue (NB 527 at this location), but signed for SB FL 527 at Orange Avenue its counterpart one block west.
US 17, 92, and 441 is only shielded as US 441 from Central Florida Parkway in Southern Orange County, FL.
FL 482 is signed as both ways as East and West off of Exit 74A on I-4 when it does not even go west of I-4.
FL 438 is signed both ways (East and West) on US 441, though technically ends one block east at Princeton and Rio Grande, should really not be for that short distance. In my opinion FL 438 should continue on Princeton ( WB on Smith Street where Princeton is one way EB) all the way to US 17/ US 92.
On US 1 in our Nation's Capital, there is a no left turn sign where US 1 turns left from Constitution Avenue to SW 14th Street. So following US 1 SB here is illegal. However, a TO US 1 assembly lies on SW 7th Street directing through US 1 SB motorists through the 7th Street Tunnel to I-395 SB back to US 1 at the 14th Street Bridge. (US 1 is like a state route in DC as Washington is like a state almost).