Live at Winterland was released by Rykodisc in 1987 and became the best-selling album from an independent label that year. With sales of over 200,000 copies, it sold more than any other Jimi Hendrix recording had in years. In a contemporary review for The Village Voice, music critic Robert Christgau was highly impressed by the performances compiled for the album, which he said is ideal for the emerging CD format and surpasses previous live recordings of Hendrix: "The sound is bigger and better in every way for an artist whose sound was his music". He named Live at Winterland the tenth best album of 1987 in his year-end list for The Village Voice. Christgau remarked on its significance to Hendrix's discography in a retrospective review for Blender magazine:
It's been eclipsed sonically (Berkeley) and conceptually (Woodstock). But this pioneering digitalization, piecing together songs from three San Francisco nights in October 1968 to simulate one uninterrupted concert, redefined posthumous Hendrix and remains a surpassingly realistic live keepsake.
In 1992, Live at Winterland was re-released with a bonus disc, which contained three additional songs from the same concerts. A 4 disc box set (titled Winterland) drawn from all 6 performances was released on September 12, 2011. A limited edition sold exclusively on Amazon.com includes a 5th bonus disc containing a bootleg soundboard recording of a performance at the Fillmore Auditorium on February 4, 1968.