A redeveloped cleveland circle

CitiBank is actually getting rid of a lot of their retail presence and focusing more on financial services. So you are going to see a lot more dead Citibank spots.

Hard to be more dead than they are already, short of being shuttered.

Here's hoping the spots don't just get gobbled up by other banks.
 
Don't forget, the Chestnut Hill Star Market was built at a weird angle to avoid Brookline NIMBY issues

https://www.google.com/maps/@42.3231036,-71.1661701,422m/data=!3m1!1e3

Reading this one year later, not to be too pedantic, but I still feel the need to correct you: Chestnut Hill Star Market is in Newton. The town line roughly skirts the building footprint, and having the building in one town rather than straddling two very likely makes far more sense from a permitting and taxation perspective... I don't have any hard info on this, but I doubt the layout of this is just because of "NIMBYs".
 
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revisiting this, all these parcels seem to be in the Aberdeen Architectural Conservation District. As absurd as it seems, this includes CVS, Mary Anns, Dunkin Donuts.

http://www.cityofboston.gov/images_documents/Aberdeen District Map_tcm3-13350.pdf

I don't have expertise in what challenges this presents, but it seems like it could block anything that doesn't preserve the current structures or restore the parcels to a historic state.
 
Much of what you put in red is actually part of the circle that once was there - Beacon laid out in Brookline bracketed by two circles, here and at Audobon. Audobon is being restored as such, and I think someday CC will do it too. At any rate, the red markings mostly cover non-developable parcels, it's just road.
 
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I hadn't seen Justin's pic above when I put this together - somewhat of the same idea, although even more emphasis on pedestrian movements and safe protected bike lanes that cross tracks at safe perpendiculars wherever possible.

Another innovation here is the ALL TURNS access road from westbound beacon to Chestnut Hill Ave. That would be on a separate signal cycle. That minimizes a lot of bike and pedestrian conflicts. Also, eastbound Beacon can no longer turn left onto Chestnut Hill Ave - they must use the turnaround by CVS and then the access road to do so.

The all-turns access road would be paved with pavers, be low-speed, and be extremely easy to cross to access the large plaza, which I'd hope could be a lively space.
 
Edit to above -

Can't believe I didn't see this obvious awesomeness when I laid out the intersection as I did...

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If you're going to be completely redoing CC, you might as well put in a fully double-tracked wye so that B<->C, B<->D, and C<->D are all viable moves. The weirdly aligned D -> B track and the lack of a B -> C track are odd results of the old circle being turned into a four-way intersection. The B -> C move can be made through the yard currently, but a direct connection would be better.
 
An idea I've been playing with for a while:
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The pool should be sold off for redevelopment, with the stipulation whatever is built there have to put in a new public pool.
 
The modern roundabout makes an excellent visual, but I have to say that in my opinion a roundabout - despite the historical layout - is the wrong intervention.

Look at how many times cars, cyclists, pedestrians and trolleys must cross each other in free-flowing traffic. I understand that part of the allure of this setup is that traffic will slow and self-regulate. I agree with that to an extent, but I also think you'd be 1) creating needless conflict zones, and 2) substituting the existing dead space in and around the intersection for new traffic-calming greenspace and the inaccessible roundabout center.

Cleveland Circle is just a simple X intersection (Sutherland is rather inconsequential) with an inscribed trolley wye. If the intersection is pulled back to its essentials, and the dead space where cars rarely/shouldn't go is eliminated, then you can create some real, usable pedestrian and shared space. (Cleveland Circle after snowfall really illustrates this point well.)

Here are some inspiration pics I used to come up with my preferred scheme:

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