Which Jazz Albums are similar to Kind of Blue

Oops, it was "Waltz for Debby" not W 'with' Debby. Hifimaniac has the right idea... the 1500 series of BlueNotes is great. Another way to do research would be to open a couple of browser windows and dig through the Allmusic.com site on one hand (good data on who plays on what albums generally, along with discography with generally good coverage) and Amazon on the other (better/longer sound clips than allmusic's) to give you an idea of what you might want to buy. Best of luck.

try Oliver Nelson's The Blues and The Abstract Truth...along with kinda blue one of my all time favorites

Agree with Henry, great call. Another one I would recommend is Herbie Hancock's Maiden Voyage. It doesn't actually sound like KOB, but it is similarly accessible and lyrical with spare arrangements and wonderful playing. The young Herbie along with the young Freddie Hubbard, the very young Tony Williams (whose brilliance is abundant on this record), and George Coleman and Ron Carter. It's a jazz album that has managed to penetrate my DNA in almost the same way KOB has.

anything with Ben Webster will likely give you a bit of that ease and magic. Ben has that combination of 'cool jazz' but with great tone and subtle energy that Miles had in KOB. Ben is my favorite Sax player.

i particularly like 'At the Renaissance'.

'Chet' from Chet Baker is another winner in that same vein.

Within Miles, try Round About Midnight