A Massachusetts couple has been vacationing with their family in Cape Cod for over 30 years, and thanks to a scratch-off jackpot, they're buying a dream home there! David must work fast to help them snatch up their perfect place in this hot market.

David gets to stay at home as he helps lucky newlyweds find their dream home in Orlando, Florida. After winning a million dollars on their anniversary, this couple wants a two-story house where they can feel like royalty overlooking the neighborhood.

After a $250,000 scratch-off win, a couple of empty nesters is finally moving back to her native Mandeville, Louisiana. While they need a fabulous in-law suite and plenty of space for visitors, David also has to find a home with a fishing hole nearby.

In North Carolina, David helps his youngest winner yet put her $390,000 towards buying a home to share with her mom and sister. There aren't many 22-year-olds with a property portfolio, so David is thrilled to find a home with pretty livestreaming spaces.

After winning big on a scratch-off, a couple is all smiles as they hunt for their dream home near Canton, Ohio. David braves the cold to help them find the perfect compromise between city and country living in a snow-covered winter wonderland adventure.

David meets his newest winners in the semi-rural countryside of the border between New York and Canada. Despite the winter chill, they're looking forward to the summers as they search for a home with country charm and a pool.

Thanks to a million-dollar win on a scratch-off, a couple and their baby can finally move out of their one-bedroom apartment. David is happy to help this family find a bigger home hear Binghamton, New York, even if he does struggle with the city's name.

The Florida lottery gives a couple of government employees a fabulous early retirement gift of six-million dollars! With their teens in tow, David shows the whole family how to revel in luxury as they embark on a spree full of sun, sand and lavish homes.

A Portland man was homeless when he inherited $1.4 million after his mother passed away. Now, he and his partner are moving to warm Cape Coral, Florida, and David is ready to find them a house where they can fish, boat and soak up the sunshine in style!

After tragically losing a husband and father, a mother and her two daughters are given a million dollars of comfort thanks to a scratch ticket. Ready to find their dream home in Leechburg, Pennsylvania, David leads the way one silly walk after another.