Joseph Kettlestrings Dunlop, grandson of Joseph Kettlestrings, the first settler of Oak Park, was a wealthy banker and realtor who built this house on land he inherited from his grandfather.  The house, where the Dunlops lived for only two years before building the house immediately to the north, was a frame Queen Anne with a turret on the the southeast corner and a massive front gable with a Palladian window.

Between 1908 and 1914 the Dunlop house was greatly altered in style when the second owners made two major additions.  The living room, dining room and master bedroom were greatly enlarged, glass enclosed sunrooms were added, and elaborate interiors were created.  The architect of the remodelling is not definitively known, but is thought to perhaps be Charles White, Jr.  The house is now in a "complex rectilinear" style characterized by flat surfaces, a gabled roof, rectilinear masses and patterned windows, a style common in Oak Park between 1900 and 1915.  In this example there are also decorative wood strips under the eaves.  The gable with the Palladian window is all that remains of the original front façade, click here for a picture of the original house.

When Joseph sold this house in 1896, he retained ownership of the rear portion of the lot.  This gave him an L-shaped parcel on which he built a barn and later the house at 407 Kenilworth.