You may or may not be aware of this, but in the early days, Cleveland Park was referred to as Cleveland Heights (i.e., Columbia Heights, and Adams Morgan formerly known as Washington Heights).
Below is a cool article that we came across in The Washington Post from June 22nd, 1890.
Three hundred feet above the tidewaters of the Potomac River lies Cleveland Heights, which, prior to its purchase by a real estate syndicate, was known as the Yturbide property. As soon as the syndicate obtained this tract of land the work of improvement began, and it is now considered one of the most attractive subdivisions contiguous to Washington.
Besides being graded, paved, and guttered, the system of parking and tree-planting adopted has made each lot doubly attractive and valuable for residence purposes. Lying as it does, between two of the principal thoroughfares of the District, Connecticut avenue extended and Tennallytown Road, upon which electric cars have been placed,d no trouble is experienced in reaching the Heights a short time after leaving the business center of the city. To-morrow afternoon promises to be a red-letter day in the history of this tract, for the remaining quarter of the property will be sold at auction, there being twenty-five lots to be disposed of. A conveyance will leave the Atlantic Building at 5 o’clock p. m., but those who cannot avail themselves of this method for reaching the sale can take either the Avenue or Metropolitan line of horse-cars, and change at High street, Georgetown, to the electric line, which runs past the tract.
Oak View, formerly the country seat of President and Mrs. Cleveland, adjoins the Yturbide property, and Twin Oaks, another pretty country seat, is but a few rods distant. Owing to the persistent efforts of a large force of laborers the face of nature in this locality has been materially changed, and it would be difficult to find a more eligibly situated and pleasanter spot for a suburban residence than is now offered to purchasers of a lot at Cleveland Heights. From the hill upon which the Heights are situated, a magnificent panorama spreads away southward, and the surroundings on every hand are such as to invite only favorable comment from the most ardent admirer of natural beauty. It will certainly be an opportunity rarely presented to get a lot in a subdivision where art and nature seems to have blended harmoniously to produce the most desirable effects, and the auction sale should not fail to attract a large attendance of persons who want beautiful villa sites.
Here are two maps of the area from 1892, showing the topography. The first map is directly west of the second one. At the bottom of it, you’ll see the Georgetown and Rockville Road, today Wisconsin Avenue.
And, in this one, you should see Pierce’s Mill Road (different spelling).