Boston, in order, within 25 miles, in my opinion:
Essex
Myopia
TCC (really interchangable with the above two)
Old Sandwich
Boston GC
Salem CC
Winchester
Concord CC (neck and neck with Winch)
Charles River
Brae Burn
Tedesco
In my Mass. rankings, Tedesco is #17...so Kittansett, Taconic, Eastward Ho, Longmeadow, Oyster Harbors, and Plymouth slot in amongst the above. My next Boston-area course after Tedesco is Black Rock at #21 (Oak Hill, Vesper, Orchards slot in between). Among Boston-area courses, the only prominent private courses I have not seen are Belmont and Cohasset. In Mass. as a whole, I have not seen the Nantucket courses, Woods Hole, Worcester, Blue Hill and a few other lesser ones.
Boston publics are a bit harder, as most of our high-end publics are in Central/Western Mass or on the Cape...too far to be considered "Boston area":
George Wright (Ross)
South Shore CC (Stiles)
Franklin Park (Ross and others before him)
Butter Brook (Mungeam)
Beverly Golf & Tennis (Stiles, maybe some Tull)
Sandy Burr (Ross)
Gannon Municipal (Stiles)
Granite Links (Sanford)
Brookline GC (Stiles)
Really stretching here as there just aren't many candidates....Fresh Pond (Walter Johnson) and Salem Muni (Stiles) are decent 9-holers but not very exciting. Ponkapoag, if ever restored in any way would be pretty good...there are/were 18 Ross holes out there, but it might be America's worst-maintained 36 holes...which may be 27 today as I believe they have let one 9 go...unfortunately I'm pretty sure it was one of the Ross 9s.