Take A Tour: Middlebury's 5 Priciest Homes On The Market Right Now

MIDDLEBURY, CT — A Colonial Revival estate designed by architect Cameron Clark tops Middlebury's most expensive homes for sale, at about twice the price of No. 2, according to listings on Zillow.com.

No. 1 on the list is 775 South St., which the listing calls Broadview Estate, listed at $2,850,000. The 1939 house sits on 12.6 hilltop acres of fields and woodlands with garden cottages and views to the east, west and north. It has 9,619 square feet, eight bedrooms, six full bathrooms and two half bathrooms. It has been on Zillow for 248 days.

Just behind it is 67 Abbott Farms Road, a custom brick Colonial built in 1999, listed at $1,399,900. A private drive leads to a circular driveway with Belgian block accents, and inside there's a sweeping staircase, a two-story great room with a fireplace, an all-season sunporch and a main-floor primary suite. The 5,237-square-foot house has four bedrooms, three full bathrooms and one half bathroom on 2 acres and has been on Zillow for 66 days.

Rounding out the top three is 135 Washington Drive, a proposed Colonial that will be built once a buyer signs a contract, listed at $999,000. Plans show 3,485 square feet, four bedrooms, three full bathrooms and one half bathroom, a home office, a fireplace and a two-car garage on a 0.92-acre lot. It has been on Zillow for 56 days.

No. 4 is 294 Christian Road, a new-construction house built on what the listing calls the Cambridge Model, listed at $995,000. It has 2,878 square feet, three bedrooms, two full bathrooms and one half bathroom on 1.05 acres, with a two-story foyer, a great room with soaring ceilings and a fireplace and a first-floor primary suite with two walk-in closets. It has been on Zillow for 42 days.

Closing out the top five is 9 Whitehall Court, a 2001 house the listing calls one of a kind within its complex, listed at $979,900. It has 4,261 square feet, four bedrooms, three full bathrooms and two half bathrooms on 0.7 acres, a first-floor primary suite and an open layout. It has been on Zillow for 45 days.

Prices, listing status and days on market are from each property's Zillow.com listing as of Oct. 26, 2026, and may change. Only homes marked "For sale" or offered as new construction were included; pending, coming-soon, land-only and multifamily listings were left out.