Here Are The Most Recent Property Sales In Chester

CHESTER, CT — From a condo on Oakwood Trail to a pair of Goose Hill Road homes, Chester's housing market has been anything but sleepy this fall.

There were five properties sold in Chester between Sept. 11 and Oct. 15, 2026, with a top price of $1.2 million, according to Zillow.com.

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112 Oakwood Trail #112 sold Oct. 15 for $645,000. The two-bedroom, three-bath condo unit was built in 2006 and has 2,000 square feet.

11 Castle View Drive sold Oct. 2 for $502,500. The three-bedroom, two-bath home was built in 1963 and has 2,103 square feet on 0.47 acres.

136 Goose Hill Road sold Oct. 1 for $825,000. The four-bedroom, three-bath home was built in 1989 and has 3,343 square feet on 2.05 acres.

19 Denlar Drive sold Sept. 30 for $1.2 million. The two-bedroom, two-bath multifamily property was built in 1972 and has 5,886 square feet on 0.66 acres.

25 Goose Hill Road sold Sept. 11 for $430,000. The two-bedroom, two-bath home was built in 1965 and has 1,454 square feet on 2.39 acres.

What this says about the Chester market: Prices in this batch ran from $430,000 at 25 Goose Hill Road to $1.2 million at 19 Denlar Drive. The mix included three single-family homes, one condo and one multifamily property. Per-square-foot prices ranged from about $204 at 19 Denlar Drive to about $322 at 112 Oakwood Trail #112. The oldest, at 11 Castle View Drive, dates to 1963; the newest, at 112 Oakwood Trail #112, was built in 2006.

Sourced from Zillow.com's recently sold listings for Chester, as of Oct. 17, 2026.