Virginia Avenue starts to get really interesting as the grade begins to climb as we head up the hill towards Meramec Street. On the left, we see the huge mass of the long-abandoned Cleveland High School, which has suffered a series of arsons in the last year.

The Public Schools found such as large parcel of land by buying the old Villa Padua property, and constructed the massive Ittner-designed school in its place.

We don’t know much about what the house looked like, but it was probably Italianate in style, and we have a group photo of the Haydel Family out in front of the villa from 1895.

The large parcels to the north became these apartment buildings in the mid-Twentieth Century, which are turned away from the street, leaving blank walls.

Moving north on the west side of Virginia Avenue, there are a whole host of very cool houses from a wide range of decades. The upper middle class to upper class typically lived on higher elevations such as the hill that crests along Meramec Avenue.

Arriving at the southwest corner of Virginia and Meramec, which is now one of the busiest intersections in Dutchtown, there was once an incredibly ornate Italianate villa with some almost Orientalist elements on the cupola.

Today, the villa has been replaced by Winkelmann Sons Drug Company in the corner space with apartments above and a barbershop behind along Virginia Avenue.

Turning around at Meramec, we go back south, looking at the east side of Virginia Avenue, where a stately building houses the offices of the Dutchtown South Community Development non-profit.

As the Meramec and Virginia commercial corridors developed, storefronts squeezed in where ever they could find the space.

Slowly, however, the storefronts, including some built in front of what were obviously houses originally, transition back over to residential character.

The so-called Virginia Manor apartment building is still sitting empty.

Then the lavish houses begin, though I realized the one below has most likely been converted into an apartment building, as there’s a large wing covered in vinyl siding sticking out the back. Also, note the small windows inserted into the larger holes.

There is this wonderful shingle style house below, as well.

There are more houses sitting high up on what is most likely the original topography of the hill, while Virginia Avenue was graded so that there would be a nice rise for horses, wagons and streetcars.