Two years ago, worried about potential increases in the capital gains tax, Milton Wood decided to sell the Tudor mansion that he and his wife, Barbara, had bought in 1976. “I lived in that house long enough that my capital gains are substantial,” says Wood, whose company provides corporate strategy and executive recruitment services.

Wood declined to say what he originally paid for the house—which was designed in 1922 by Solon S. Beman Jr. (his father was the architect for the town of Pullman) and christened Meadow Pool—and the figure cannot be determined from public records. The Woods did make several improvements, upgrading the basement and putting on an addition that included a family room with ceilings two and a half stories high. But given the local real-estate market 30 years ago, the Woods probably paid below $1 million for the place—which means they likely have turned a profit of at least $2.5 million.

When Dinny Dwyer, of Jean Wright Real Estate, got the listing in February 2007, the 22-room house, on the market since 2006, had an asking price of $4.6 million. She and the Woods cut the price to $3,999,999 before landing a buyer in January 2008. The deal closed the same month, and the Woods moved to Kenilworth. The buyer could not be identified from public records.

Photograph: VHT Studios