Oak Park’s most prolific architect isn’t Frank Lloyd Wright—it's E.E. Roberts. The turn-of-the-last-century master practiced Prairie with the best of ‘em, and paralleled Wright’s career arc through early intersections with Queen Anne and other traditional styles. With some 200 works in Oak Park, Roberts was a favorite of the wealthy homebuilding set.

Two of Roberts’ grandest homes listed for sale in mid-May on the same block of North Kenilworth Avenue, one block east of the village’s greatest concentration of Wright homes, including Wright’s home and studio. Each estate has nearly an acre of land and deep setbacks, and an orientation toward side and back yards (which is handy when roving bands of historic sightseers come around).

Tackling the houses chronologically, we have Roberts’ transitional Queen Anne built in 1897 for Joseph K. Dunlop, grandson of Oak Park’s founding settler Joseph Kettlestrings. It’s on the market for $2.25 million. A wide, deep porch gives balance to the very tall, sharply pitched structure and the 6,600 square-foot six-bedroom behemoth casts one of the most striking profiles in town—bone white against the lawn and old growth oaks. An L-shaped lot creates a nicely defined compound, with a coach house, garage, and pool in the larger rear stretch of property.

Inside, the main floor has 11-foot ceilings, large leaded windows, and curly birch cladding. I visited on a sunny day, but still, I can’t remember a naturally brighter interior. And that’s not even counting the climate controlled English conservatory serving as family room. Gorgeous wood-burning fireplaces accent living and dining rooms, and a 1990s rear addition includes a newer kitchen with reclaimed Southern Yellow Pine cabinetry and marble counters. There’s also a non-functioning antique stove that comes with the sale—and it makes for quite an ornament.

Several doors south on Kenilworth, another E.E. Roberts-designed spectacle is for sale: It's the Benjamin Porter Horton Residence, newly listed for $3 million. This is a resounding Prairie Style home from 1913, the confident work of an architect in his prime.

The home’s double lot has some of Oak Park’s oldest trees and is protected from future development by a preservation easement. Its award-winning landscaping, executed over several years, divides open space into “rooms”—a reflecting pond room, front lawn room, and pebble pond room—with a very old lofted barn/coach house at the far end, generations older than the main house.

The home’s recorded square footage is 4,835, but that doesn’t include the finished basement with a fitness center, sauna, and wine cellar, and another 1,500 square feet of coach house. The property underwent a total restoration in the last decade, during which the owners confined themselves to the third floor. Most of the woodwork on the lower two floors is original and much of the old art glass has been restored, while some doors and lighting are new. A two-way hearth was built for the family and dining rooms complete with an abstract landscape mural.

The narrow, sequestered kitchen and dining area has handcrafted cherry woodwork, high-end appliances, granite counters, inset lighting, and the brick of the hearth. All of the main floor spaces are wired for sound and security. The second floor was completely re-imagined during the whole-house renovation. It functions as a huge master suite, with rooms for dressing, bathing, and reading, along with a large back terrace.

In another instance of architectural trickery, most of the home’s rooms look south and east to the verdant landscaping. “To find a piece of property like this so close to the city is really unusual,” says listing agent and Oak Park native Greer Haseman of Gagliardo Realty Associates. “Two on the same block? Even more so.”

Both sellers are downsizing, according to Haseman, and neither wished to be quoted for this story.