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Ashland Park :

Lexington has its own “Millionaires Row” just east of downtown. I’m referring to the collection of gorgeous mansions on well-manicured lawns along Richmond Road next to the Henry Clay Estate. They belong to one of the most distinctive neighborhoods in town, Ashland Park.

The storybook setting of this subdivision makes it a must-see for anyone who appreciates good design and elegant older homes. Its curving lanes and mature trees are the result of thoughtful planning by the famous Olmsted brothers in the late 1800s. In fact, the entire neighborhood is now on the National Register of Historic Places.

Chevy Chase:

Bordering the University of Kentucky, the neighborhood of Chevy Chase is less than one-square mile with a little over 1,000 neighbors. Founded in the 20s and 30s by Henry Clay Simpson, a direct descendent of Statesman Henry Clay, it was originally part of his estate, Ashland.

Whether the reason is city planning, or paying homage to Chevy Chase, there are indeed a few roundabouts nearby. The neighborhood is actually named after a Maryland Golf Course which Simpson once belonged. This is the kind of neighborhood you might like to raise kids. The tree-lined streets, bungalows and cottages abound. Yet, in the center of it all, is a small village of restaurants, bars and shops where everyone knows your name.