R
ichard Gere’s 2022 purchase of the former Paul Simon estate in New Canaan, Connecticut, sparked controversy. The 10.8‑million‑dollar deal, reported by CT Insider, was followed by a public spat when Simon’s daughter Lulu posted that she still despises Gere, accusing him of buying her father’s childhood home, failing to occupy it, and selling it to developers as nine separate parcels. Simon and his wife Edie Brickwell had lived there for two decades before selling to Gere.

    Gere and his wife, Alejandra Silva, initially intended to transform part of the property into a farm, producing mushrooms, honey, and eventually goats. In a 2023 town meeting they declined to subdivide the land or add new homes, though the zoning board expressed concerns about the goats, which Gere said were a future plan. By April 2024, Gere announced a move to Spain to be near Silva’s family, seemingly abandoning the Connecticut site, though he later said the couple would return to the U.S. in a few years. The property was sold again for $10.75 million in October 2024, according to Mansion Global.

    The New Canaan Inland Wetlands and Planning & Zoning Commission approved a subdivision of the estate into nine lots—the town’s largest split since 2007—connected by a cul‑de‑sac on Brookwood Road. The original house was demolished in September, with salvaged pieces auctioned by Hudson Valley House Parts, drawing widespread criticism. On November 10, two lots went on sale: 48 Brookwood Lane, a 4.01‑acre parcel with a 1940s three‑bed, two‑bath cottage priced at $2.95 million, and 122 Brookwood Lane, a 2.16‑acre lot listed for $2.495 million. The remaining seven lots, ranging from 2.5 to 4.8 acres, have yet to be marketed.

    Other notable transactions include Bill Belichick’s Nantucket cottage selling for $4 million, Dave Portnoy’s $28 million Florida Keys mansion, and Thomas DeVesto’s $12.5 million waterfront home in Cotuit.