Ray leads his clients through the crumbling, faded streets of central Havana, just off the city's Malecón where you can taste salt in the air coming off the Florida Straits. The 65-year-old walks with purpose, though he asks foreigners to keep a few paces behind him and talk among themselves lest police hassle him. "This next one is lovely," he says slyly turning to his clients. "It has a view of the sea from the balcony and you have all the shops nearby." In the three-bedroom, third-floor apartment, Ray shows off a "big bathroom" which has barely enough space to walk around. Typical of many Cuban homes, its furniture and electrical equipment — such as a large transistor radio — would fit nicely into a museum. The entire place will cost $30,000, though, Ray advises, it "needs work."

Ray's spiel is as practiced as estate agents the world over. But in Cuba, there's one difference: his work is illegal. For it, he will receive 10 percent of the sale price and perhaps a tip from the buyers, he suggests with a smile in the living room he is showing off.

In November 2011, the buying and selling of property on this Communist island became legal, in one of many cautious reforms enacted by the government of President Raúl Castro to open up the country's economy. Ray's commission makes him a broker and puts him on the wrong side of the law. "I do this because I make money," says Ray. Just as in nearby Venezuela, capitalism is at its most naked in countries governed by hard-left economies. Ray, like many Cubans, has found a way around the average wage of some $20 a month here. "Cubans are nothing but resilient and will always find a way to monetize things," says Ann Louise Bardach, a long-time Cuba analyst and author of Without Fidel: A Death Foretold in Miami, Havana and Washington.