45 Bromfield Street | Downtown Crossing

Those are both good examples. Atlantic Wharf, in particular, manages melding old and new deftly.

A counter example: The Kensington. It doesn’t consume the whole block, but falls flat both fitting in and standing apart.
 
There's a little bit of info in the article about the potential height of the larger tower:
Midwood Investment & Development has told the city it plans to develop 918 apartments on two Bromfield Street sites. One tower, at the corner of Washington and Bromfield streets, could reach 500 feet and house 760 apartments, while a second property up the block at 45 Bromfield St. could include 158 apartments in a 17-story building. Together, the two buildings would have about 180 units set aside at affordable rents.
 
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