Those dreams of new beach resorts, golf courses and condos seemed a little closer to reality after this past December, when presidents Raul Castro and Barack Obama declared Cuba and the U.S. would try to normalize relations after 53 years.
But Cuba's top North American envoy has a special message to all those dreamers — keep dreaming.
"We are not against selling property, but not freely," said Julio Garmendia Pena, the Cuban ambassador to Canada.
"We want to keep the country for Cubans."
In a recent speech in Ottawa to an audience of diplomats, academics and government officials, Pena made clear Cuba may be open to foreign investment, but buying land is not on the table.
Many obstacles remain to a full-on Cuban-American rapprochement, including two big ones — establishing diplomatic relations and lifting the crippling U.S. economic embargo, which Cuba simply calls the blockade.
But the biggest one is a long-running feud over property, valued at billions of dollars.
After Fidel Castro's communist revolution in 1959, the new Cuban government seized and nationalized U.S. assets across the country. These included the American-owned telephone company, utilities, sugar cane fields, and various properties, including several Hilton hotels.
When heiress Paris Hilton recently visited Havana and posted selfies in front of the old Hilton hotel, she was castigated online for thumbing her nose at the legacy that underwrites her current life of celebrity leisure.
The value of seized American assets has been estimated at as much as $7 billion, much of it claimed by the very angry and influential Cuban expatriate community in Florida that reviles the Castros.
Like many other informed observers, Mark Entwistle, Canada's ambassador to Cuba from 1993-97, said Monday some sort of compensation agreement will have to be reached before Cuba and the U.S. can move forward.
As one of the founders of a Toronto-based boutique merchant bank (his partners include Belinda Stronach and former Onex executive Anthony Melman), Entwistle has spent a lot of time in Cuba the United States recently.
One refrain he is hearing in the U.S. these days goes like this: "How do I buy that piece of beachfront, how do I buy a downtown city block of Havana to redevelop it?"
No time soon, is Entwistle's standard answer, because Cuba views land as a national asset that belongs to the state.
"There's a sense, especially in the United States, that there's some gold rush bonanza is about to happen," said Entwistle.
"This is largely informed by a tremendous lack of information and understanding of Cuba itself, and where the Cubans have come from, and who they are and where they're going."
Pena himself made clear that Cuba had learned lessons from its pre-revolution era of American influence.
"We already went through this," he said. "And at the end of the day, when we began to see who is owning these properties, it was a frightening list. So we decided to be more careful in that direction."
Eventually, Entwistle said, Cuba will have to open itself up to more foreign investment if it wants to grow an economy hobbled by a half century of economic isolation from its massive neighbour 135 kilometres to the north.
But that doesn't mean Cuba will start selling off deeds and titles to hoteliers and developers, especially from the United States, he added.
"A situation in the past, in Cuban history, where one country owned two-thirds of the national economy and all the utilities and phones and electricity and over 80 per cent of the fertile sugar lands and agricultural lands — that's not going to happen again."