Here Are The Most Recent Property Sales In Middlebury

MIDDLEBURY, CT — From a new-construction condo on North Benson Road to a 1960 home on Northwood Drive, Middlebury closed five sales in eight days.

There were five homes sold in Middlebury between Oct. 8 and Oct. 15, 2026, with a top price of $715,000, according to Zillow.com.

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80 Pine Hollow Drive sold Oct. 15 for $715,000. The four-bedroom, four-bath home was built in 1979 and has 2,806 square feet on 1.65 acres.

90 Fenn Road sold Oct. 9 for $620,000. The four-bedroom, four-bath home was built in 1989 and has 3,162 square feet on 1.67 acres.

112 Joy Road sold Oct. 9 for $499,900. The three-bedroom, two-bath home was built in 1974 and has 1,900 square feet on 0.46 acres.

65 North Benson Road #65 sold Oct. 9 for $573,572. The three-bedroom, three-bath condo unit was built in 2026 and has 2,206 square feet.

123 Northwood Drive sold Oct. 8 for $535,000. The three-bedroom, three-bath home was built in 1960 and has 1,552 square feet on 0.67 acres.

What this says about the Middlebury market: Prices in this batch ran from $499,900 at 112 Joy Road to $715,000 at 80 Pine Hollow Drive. The mix included four single-family homes and one condo. Per-square-foot prices ranged from about $196 at 90 Fenn Road to about $345 at 123 Northwood Drive. The oldest, at 123 Northwood Drive, dates to 1960; the newest, at 65 North Benson Road #65, was built in 2026.

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