Than's marketing prowess pays off when CT Homes is contacted about a new find. The owner of a 108 year old single family home on New Haven's West Ivy Street is desperate to get rid of the house. After checking the property over, Than takes it off the owner's hands convinced that after some paint and a new roof, CT Homes will stand to make a huge profit from this century-old charmer. However, looks can be deceiving. As demolition begins, rotten exterior siding is revealed as well as some major plumbing issues. On the bright side, after a major clean up of the garage, JD uncovers a '67 Cadillac that is also in need of some tender loving care. Between the house and the car, the team at CT Homes will have to come together--it's time to turn this Caddie Shack into a Cadillac.