We pass a waterfront home owned by Wick McNeely, of a fifth-generation Chester summer family from Virginia, who bought the property last year for a rumoured $4-million. I'm told McNeely is in the concrete business and doesn't give interviews. Like many Chester summer families, he's understated, and does things for the community, anonymously.

"You don't have to be wealthy to live here," says Harris. "You can still buy a house in Chester for $200,000, but not on the water." In the village of Chester, the average price for an acre of land on the water, with no buildings, is approximately $1-million. "An acre of land with 200 feet on the water just sold to a man from the U.K. for $1.1-million. Many of the people who come here and pay the big prices, have an ex-patriot as a spouse, or they may both be Canadians returning home after doing well, and Chester is the place they'll buy." says Harris. "Chester has so much to offer, including the yacht club and the Chester Golf Club."

We pass McNeely's magnificent sailboat, a Hinckley 51, and see McNeely in a raft with one of his grandsons. He tells me the sailboat, named Night Train, sells in the seven-figure range. "I hear it's the nicest boat in Chester," I tell him.

"Last year, it was one of the nicest boats in St. Bart's," he informs me. The well-tanned McNeely tells me his great grandmother first came to Chester in 1851. As we continue on our tour, he encourages, "Say something nice about Chester."

But they don't come to Chester only from the United States and Britain. One local artist is from Barcelona. Jose Valverde Alcalde has bridged the gap from Spanish villas to sailboats. When I visit him and his wife, Doreen, in their studio home on the main street of Chester, Valverde sweeps downstairs, dressed more for Spanish dancing in his black pants and crisp white shirt, than for painting.

"When we came to Chester 22 years ago, we loved it, it's so beautiful, the most beautiful place in the world. We raised our kids in Chester." But he admits he winters in the coastal Spanish village of Sitges.

His Nova Scotia sailboat art, he says, was inspired three years ago during some schooner races. He ships pieces around the globe.

"There are people here from every different background," he says. "You go to the yacht club, you see people and you want to give them your trousers [they look so poor], and then you find out that they are multimillionaires. It is a lovely place to live and to do business."