In 1880, John Nelson Hayes Patrick, a real estate developer, hired Shannon Brothers of Kansas City to construct six homes between 48th and 52nd Streets, Capitol to California. They named the new addition Dundee Place after another successful development the contractors had recently finished in Kansas City. Dundee, Omaha's first suburb, was developed over a century ago. Dundee was built one house at a time. This accounts for the original architecture you find from house to house in the neighborhood.
On October 30, 1888, the Daily Herald ran an ad for Dundee Place. The ad urged prospective buyers to examine covenants that all homeowners would need to abide by. These restrictions included that all dwellings be constructed for residential purposes only and stand at least 25 feet away from the street. The rules also stated that a Dundee residence must cost at least $2500 and that no structure could be used for any immoral or illegal business, nor shall any spirits or malt liquors be sold or bartered away.
The ad did not work as well as hoped and home sales were going poorly. The developers decided to develop Dundee as a village. Underwood Avenue was named after one of the Kansas City real estate men. Because the village seemed so desolate, the developers purchased over 2,000 maple trees and planted them along the roadways. As an enticement to move so far from the city, Walter L. Selby offered a free lot to each buyer. If the buyer built and stayed there for a year, he was offered a bonus of $500.
This did the trick. A housing boom began in 1905. Houses were also being built next to the official village south of Dodge Street and north of Cuming Street, so these two areas were annexed by Dundee. Real estate men C.C. and J.E. George laid out Happy Hollow Boulevard and developed the area south of Dodge and west of 50th to Elmwood Park. They filled in the creek that ran along 50th Street and added sidewalks and the Dundee lights. Homes in the area reflected the Colonial, Georgian and Tudor Revival styles. Omaha annexed Dundee in June of 1915.