The Highland neighborhood of Waterloo was platted in 1900 and again in 1907. With the help of developers Lewis Lichty and John and Mary Steely, it soon became Waterloo's premier residential district.

Some 24 homes were designed by architect Mortimer Cleveland. The neighborhood itself was placed on the National Register of Historic Places in 1984. Architecturally significant homes include:

- 205 Prospect Avenue
- 215 Prospect Avenue (Mortimer Cleveland's Home)
- 225 Highland Boulevard

Prominent residents of Highland during its peak before 1940 included John and Reuben Rath, presidents of Rath Packing; Keith Funston, later president of the New York Stock Exchange; and A. B. Chambers, later mayor of Des Moines. At that time, the neighborhood consisted largely of business owners, business managers or professionals.

Highland began to decline during the 1950s, as Waterloo's "elite" began moving to the expanding west side of town. The Highland neighborhood underwent a slow transformation into the middle class area it is today.

The Highland Neighborhood Association, formed in 1936, has done much to preserve or restore the architectural integrity and community spirit of this part of Waterloo. Through its newsletter, directory and activities, the Association and its members have helped keep Highland a distinctive and historic neighborhood.