Barbieri estimates that as many as 10 more properties in that range may come to market by year's end. He said he'll list two new ones in the next month.
Stanley Cheslock says he hopes this is the year his 21-acre (8.5-hectare) Hillcrest Estate, with its 50-foot indoor lap pool and "Siberian spruce sauna," will find a buyer. He first put the property up for sale in 2006, asking $31 million.
'Huge Estate'
"The kids were all moved out and the house was larger than we needed," said Cheslock, 65, founding partner of Cheslock Bakker & Associates, an investment firm in Greenwich. "Right now we're taking care of this big, huge estate, and while it's fun, I'd like to do other things."
Cheslock and his wife spent about $19 million to acquire the land and build the house, plus "a couple million" more for renovations over time.
In 2008, the couple hired an auction company to handle the sale, ahead of what Cheslock viewed was a softening real estate market. Bids starting at $19 million were solicited over five weeks. None of the would-be buyers sealed the deal with a check or agreed to the sale terms, according to Cheslock and Ward of Prudential, who represented him in the auction.
Cheslock returned to the market in October 2009, separately listing the home along with the 21 acres, and an adjacent 8-acre parcel with a cottage.
The parcel and cottage sold last June for $4.5 million, and the remaining estate, priced at $15.95 million, is still available for a "unique buyer" who craves the privacy of a gated compound at a discount.
"Somebody's going to get the deal of a lifetime," said Jason Kinard, managing partner of the Higgins Group of Greenwich, the broker that most recently listed Cheslock's home. "In anywhere from five to seven years they're going to be very happy with what the house will be worth and what it can fetch on the open market."