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Clear out junk files and repair common Windows errorsFree Scan →Scan for outdated or missing drivers - takes under a minuteDriver Scan →Repair Windows errors before they cause bigger problemsFix Now →Paul Simon and Edie Brickell sold their New Canaan, Connecticut, estate in July 2022 for $10.8 million, compared with a reported $16.5 million purchase price in 2002. The $5.7 million gap is the difference between those reported prices—not a verified net or after-tax loss.
How much did Paul Simon lose on the Connecticut estate?
The reported sale price was $5.7 million below the reported purchase price. Hearst Connecticut Media cited New Canaan town property records for the 2002 purchase figure and reported the 2022 sale at $10.8 million. The subtraction describes a nominal price difference; it does not establish how much Simon and Brickell ultimately gained or lost financially.
The available transaction reporting does not state the owners’ tax basis, improvement expenses, ownership costs, financing costs, selling expenses, or tax treatment. Without those details, the actual net and after-tax result cannot be calculated from the two sale prices alone.
Purchase, asking prices, and sale
The estate, at 82 Brookwood Lane, covered roughly 32 acres. Its asking price changed during the years it was marketed before the reported 2022 closing.
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Outbyte Driver Updater FREEScan for outdated or missing drivers - takes under a minuteDriver Scan →Outbyte PC Repair FREEClear out junk files and repair common Windows errorsFree Scan →| Date | Reported price | What it represents |
|---|---|---|
| April 2002 | $16.5 million | Purchase price, according to town property records cited by Hearst Connecticut Media. Source |
| April 2019 | $13.9 million | Initial reported asking price. Source |
| November 2020 | $11.9 million | Reported asking price when the property was relisted. Source |
| By March 2021 | $12 million | Reported asking price at that point in the listing history. Source |
| July 2022 | $10.8 million | Reported sale price; the transaction was described as finalized July 1. Source |
The property was first listed in April 2019, removed from the market in August 2020, and relisted that November. Asking prices are not sale prices, so the listing history provides context but does not change the reported $10.8 million closing figure.
Why the $5.7 million difference is not a full loss calculation
A purchase price and a later sale price show only the nominal difference between those two reported transaction amounts. They do not account for costs incurred while owning or selling the property, changes to the property, or taxes. The cited reporting does not quantify those items or explain what caused the sale price to be below the original purchase price.
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Accordingly, it is accurate to say the estate sold for $5.7 million less than its reported 2002 purchase price. Calling that figure a net loss, an after-tax loss, or the couple’s total financial loss would claim more than the available figures establish.
Independent reader supportYour contribution helps us test, update, and keep practical guides available for everyone.What happened to the property after Simon and Brickell sold it?
Later reporting says the buyers in 2022 were Richard Gere and Alejandra Silva. The property then sold to Brookwood Hills LLC for $10.75 million in 2024. Those were subsequent transactions, separate from Simon and Brickell’s sale. CT Insider’s 2024 report
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In April 2025, New Canaan’s Planning and Zoning and Inland Wetlands commissions approved a nine-lot subdivision plan. Town application materials identify the parcel as 31.7932 acres and describe proposed demolition of existing features. In an April 10, 2025 memo, Town Planner/Senior Enforcement Officer Sarah Carey wrote: “Overall, I have no objections to the proposed subdivision and find that it complies with all applicable subdivision regulations.” That assessment concerned the subdivision application, not the earlier sale by Simon and Brickell. New Canaan planning memo
By September 2025, CT Insider reported that the estate house had been demolished. In December 2025, two subdivided lots were reported listed for $2.95 million and $2.495 million. Those amounts were asking prices at the time, not confirmed sale prices. September 2025 report December 2025 lot listings
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