What is now 427 / Ronald Reagan used to be part of the Sanford-Orlando Road, and the original Dixie Highway (17-92 path became the new Dixie Highway in 1927). Roads in the old days did not use to be as straight and smooth as today. They were more meandering and often took angles, especially in towns. This section between Sanford and Winter Park was paved in brick in 1916.
Where the modern highway takes a smooth jaunt to the northeast toward Sanford, the old road took a line through what is now this brick neighborhood road. It then took a right angle on to Palmetto for a block before rejoining the northeasterly direction.
This narrow middle section is part of the original road. It was re-discovered and preserved in the early 2000s when the city was undertaking a historic brick paved roads project. It actually uncovered the original brick! It had been covered up in asphalt over the years. Quick thinking on the part of city officials kept it in place with its original brick and curbing. They scraped off as much of the old black top as possible to resurface the old brick.