Judge David Dixon sentenced Charles Jenkinson, 71, of Moorbank Close, Sandygate, Sheffield to 10 months in prison, after the pensioner pleaded guilty to two breaches of his restraining order.
Jenkinson's courageous victim, who used to be his neighbour, described the devastating impact his 19-year long campaign of harassment had had on her when she read out her statement at Sheffield Crown Court, via video link.
She said: "This man has blighted my life now for 19 years. I have suffered from anxiety and depression [as a result]. I have trouble feeling safe in my own home.
"Much of the time I feel upset and agitated, and I'm a prisoner in my own home.
"I'm unable to open the windows and doors, and feel scared to pick up post or open the door.
"I feel like I'm being observed all of the time.
"He's taken out memberships in my name, threatened to take me abroad and to keep me in his house.
"I don't feel safe. The only time I've felt relief is when the police have told me they have him in custody.
"He has breached the restraining order a number of times and I don't understand why he's been allowed to continue the harassment.
"He makes me feel sick. I find him disgusting and repulsive.
"He was told this would be his last chance and I'm just devastated that this has happened again."
Beverley Tait, prosecuting, told the court how Jenkinson had 'developed an obsession' with the woman soon after moving onto the same Sheffield street as her in 1998.
The court was told how Jenkinson would watch the woman in her garden, send her letters and come to her door.
Ms Tait said Jenksons's harassment of the woman only began to relent when he moved away in 2002. But he stepped up his campaign once again in 2014, and in May of that year Jenkinson was convicted of harassing her and a restraining order was taken out against him.
Jenkinson breached the order in October 2014, August 2015 and September 2016, but managed to escape prison on each occasion, being dealt with at court by way of suspended sentence or community orders instead.
His latest breaches took place last month.
On July 14, the woman's neighbour, who had been informed of the restraining order, saw Jenkinson walk past her house and get into a car.
He made a note of Jenkinson's registration number. Two days later on July 16, the same neighbour saw Jenkinson walk towards the complainant's house again.
Ms Tait told the court: "The neighbour shouted towards the defendant: 'Excuse me, you're not supposed to be down here'.
"The defendant said: 'Yes, I know I shouldn't'."
Defending, Rebecca Tanner, told the court that Jenkinson suffered from paranoid schizophrenia as well as an additional mental health disorder that gave him the 'wrongful belief' that the complainant felt a level of affection for him.
She said: "But for this prosecution, he has lived a blameless, law-abiding life and it's as a result of the defendant's mental health that he has caused the problems he has towards the complainant."
Sentencing Jenkinson, Judge Dixon said: "Your behaviour is wrecking her life. She doesn't even feel safe in her own home."
He also commended the complainant for her bravery, as well as her neighbour for his 'neighbourly spirit' which had resulted in Jenkinson's latest conviction.