Connor Craig Wayne Taylor, of Prospect Crescent, Scarborough, and the teenager who cannot be named for legal reasons, were sentenced at York Crown Court on Thursday.
Taylor was imprisoned for five years and the teenager has to spend one year in youth detention.
They pleaded guilty to a series of burglaries towards the end of November and December last year, making off with thousands of pounds worth of goods as well as causing thousands of pounds of damage to the homes and a car.
They were jointly charged with burglaries at Overgreen View, Burniston, on 13 December; Church Walk, Staxton, on 15 December; Throxenby Lane, Scarborough, 8 December; and Alexandra Park, Scarborough, on 1 December 2017.
Linked to the burglary in Burniston on 13 December, Taylor and the youth also pleaded guilty to aggravated vehicle taking after taking a Vauxhall Astra.
Additional offences for Taylor included driving without a licence, driving without insurance and possession of a knife.
Taylor was also charged with breaking a curfew related to bail conditions on 28 December.
Taylor asked for burglaries he committed on Gladstone Road, Scarborough, on 25 June 2017, Thompson Close, Scarborough, on 19 June 2017, and another on Settrington Road, Scarborough, on 14 December 2017, to be taken into consideration for the sentencing.
Following an investigation by local detectives, the suspects were arrested after the burglary in Staxton on 15 December.
The officers were able to piece together their web of offending and secure the convictions.
Detective Constable James Temple, of the Scarborough Serious Crime Team, said: “Connor Taylor and his teenage accomplice have caused so much misery, anguish and fear in the Scarborough area.
“The burglary spree they went on is truly shocking and this type of behaviour cannot be tolerated.
“It is bad enough to break in and steal from people’s homes, but to then to deliberately flood the houses on Overgreen View at Burniston and Thompson Close and Gladstone in Scarborough, is shameful and wicked beyond belief.
“We are pleased that the outcome at court will bring some comfort to their victims, knowing that those responsible for the terrible time they have endured have now been brought to justice.”