Winchester was nominated for the Best Country Male Vocalist award at the Juno Awards of 1990.
In 2002, he moved back to the United States,  settling in Memphis with his girlfriend, Cindy.
That year, his song "Step by Step", from the album Let the Rough Side Drag, was used as background music for the montage that ended the first season of the television program The Wire.
He received a Lifetime Achievement Award from the American Society of Composers, Authors and Publishers in 2007.
Winchester continued to record and perform throughout the United States and Canada, releasing his tenth studio album, Love Filling Station, in 2009.

In 2011, Winchester was diagnosed with cancer of the esophagus and underwent treatment for the next couple of months.
He was later given a clean bill of health from his doctor and resumed touring.
Quiet About It, a tribute record to Winchester, was released in 2012, featuring James Taylor, Lyle Lovett, Lucinda Williams, Rosanne Cash and Jimmy Buffett, who spearheaded the project, among others.

In April 2014, it was revealed that Winchester was gravely ill and receiving hospice care at his home, in Charlottesville, Virginia.
He died there on the morning of April 11, 2014, aged 69, from bladder cancer.
He is survived by his wife, Cindy and three children from a previous marriage: James, Alice and Marcus Lee.

Winchester’s final CD, A Reasonable Amount of Trouble, was released in September 2014, with liner notes by his friend Jimmy Buffett.
It was nominated for two Grammy awards.
 Rolling Stone called it "a gentle collection of playful songs about love, memory and gratitude that amounts to one of the most moving, triumphant albums of Winchester's 45 year career."
Winchester was nominated for the Best Country Male Vocalist award at the Juno Awards of 1990. In 2002, he moved back to the United States,  settling in Memphis with his girlfriend, Cindy. That year, his song "Step by Step", from the album Let the Rough Side Drag, was used as background music for the montage that ended the first season of the television program The Wire. He received a Lifetime Achievement Award from the American Society of Composers, Authors and Publishers in 2007. Winchester continued to record and perform throughout the United States and Canada, releasing his tenth studio album, Love Filling Station, in 2009.
In 2011, Winchester was diagnosed with cancer of the esophagus and underwent treatment for the next couple of months. He was later given a clean bill of health from his doctor and resumed touring. Quiet About It, a tribute record to Winchester, was released in 2012, featuring James Taylor, Lyle Lovett, Lucinda Williams, Rosanne Cash and Jimmy Buffett, who spearheaded the project, among others.
In April 2014, it was revealed that Winchester was gravely ill and receiving hospice care at his home, in Charlottesville, Virginia. He died there on the morning of April 11, 2014, aged 69, from bladder cancer. He is survived by his wife, Cindy and three children from a previous marriage: James, Alice and Marcus Lee.
Winchester’s final CD, A Reasonable Amount of Trouble, was released in September 2014, with liner notes by his friend Jimmy Buffett. It was nominated for two Grammy awards.  Rolling Stone called it "a gentle collection of playful songs about love, memory and gratitude that amounts to one of the most moving, triumphant albums of Winchester's 45 year career."
Jesse Winchester