A new generation is skipping the 'starter home' and betting heavily on high-end real estate. Two years ago, when he was 26, Matt Winter paid a little over $1 million for a four-bedroom, Mediterranean-style house in Culver City, an artsy, formerly industrial section of Los Angeles. This month, the now 28-year-old Mr. Winter, who runs his own interior design firm, paid about $1.7 million for his second home, a three-bedroom, Spanish-revival in Westwood, a neighborhood near UCLA. "I have always felt that having your money in property is the safest and best thing to do if you want to grow your personal wealth," says Mr. Winter, who founded his design company at 23. None of Mr. Winter's assets are in the stock market—he says the market "spooks him" and that he prefers to invest in real estate. Mr. Winter is part of a growing group of wealthy young buyers who are making inroads in the world of high-end real estate, acquiring properties...