I was walking by and could not resist following up on this building. It covers the full blockfront of Central Park West between 103rd and 104th Streets and there are at least three distinct pieces visible from the street: the old masonry on the north and south sides (the north facade is on the right, above the red car), the top floor, and the east facade-and-a-bit facing the park.
My first thought – being (a) familiar with the kinds of alterations that buildings in Manhattan have undergone in the past and (b) having a somewhat suspicious nature – was that this was an old apartment house to which someone added a new top story and a new east facade. There are a number of pieces here that are very difficult to fit without that explanation: the jarring difference between the side-facade masonry at the first through fifth floors and the other masonry, the basement floor that looks half-sunk on the front, the fact that the north and south ends of the building appear to have floor levels a few feet higher than everything in the middle. The north and south facades look to be pre-1920 and maybe pre-1900, but the current building is listed in various sources as built 1930 and 1969. A date of 1969 sounds about right for the front facade; the fact that the DoB records say 1930 is meaningless, as the database s known to contain incorrect dates for many hidings constructed before 1938.
Here’s a city tax photo from 1940 or shortly afterward:

And suddenly the front facade matches the sides (sort of) and the building is only five stories tall. The first story is a good match, as are parts of the upper floors. If we assume that whomever was altering the building replaced some of the windows with larger ones and removed the terra cotta ornament around the widows, it makes sense. Note that the south end of the building (the part above the “29” on the sign) is slightly higher than the middle portion, as it true today. Here’s a 1930 map:

(The Protestant Half-Orphan Asylum was a charity dating back to 1834 that provided assistance and optional shelter to children with only one parent.) Our building is shown as nine buildings, apparently constructed as a row of tenements, including, per the Old Tenement Law, airshafts (shown as squares at the lot lines). Looking back at the 1940 photo, it’s clear that there are separate entrances to each of the nine sections. These buildings were constructed to fill the lots to the maximum allowed under the Old Law, which meant small rear yards for the mid-block sections and 100 percent lot coverage less two long and narrow airshafts for each of the two end sections. Let’s try 1898:

And there’s our evidence that the sections were treated by the owner/developer as one building, even though physically they were separate buildings. It was “The Parkview,” and may have been built under the Old Law but had pretensions to be something more than tenements.
There are no DoB records readily available that go back before 1971, but there was a temporary Certificate of Occupancy issued that year for a 6-story building encompassing seven separate lots making up the full site. That sure sounds like the final stages of an alteration, which suggests that 1969 date is when all the work was done.
I could keep going but I feel like this is enough to explain how the current appearance came to be. The changes in windows and doors, the changes in fire escape locations, and the changes in minimum apartment requirements between the Old Tenement Law and the modern Multiple-Dwelling Law all suggest that the interior was gutted down to the bare wood floors.
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