MIDDLEFIELD, CT — Middlefield's most expensive homes for sale all list for under $750,000, and two of the top five are cottages on Lake Beseck, according to Zillow.com.
No. 1 on the list is 88 Powder Hill Road, an 1880 house listed at $749,900. It has 2,458 square feet, four bedrooms, two full bathrooms and one half bathroom on 1 acre, with an open kitchen and dining area, a sunroom-style flex space and a living room with a working fireplace, close to Powder Ridge, according to the listing. It has been on Zillow for 108 days.
Just behind it is 19 High St., the Chilson Bailey House, a center-chimney Colonial from about 1750 with a 2008 addition, listed at $699,000 after a $50,000 price cut on Sept. 21. Zillow lists 4,073 square feet with four bedrooms, two full bathrooms and one half bathroom on 1.2 acres. The listing says two of the bedrooms are in the original 1750 section, which isn't livable now and needs renovation, so day-to-day life happens in the 2,963-square-foot addition. It has been on Zillow for 84 days.
Rounding out the top three is 34 Fowler Development, a for-sale-by-owner house on Lake Beseck, listed at $634,900 after a $12,800 price cut on Sept. 7. Gut-renovated in 2019, the 1940 house has 1,008 square feet, two bedrooms and one full bathroom, with lake views and an open floor plan. It has been on Zillow for 54 days.
No. 4 is 18-A Lake Shore Drive, a 1930 direct-waterfront cottage on Lake Beseck with private docks and a floating dock, listed at $595,000. Motorboats are allowed on the lake, according to the listing. The 961-square-foot cottage has two bedrooms, one full bathroom and a sunroom on a 5,227-square-foot lot. It has been on Zillow for 27 days.
Closing out the top five is 4 Stowe St., a 1972 raised ranch on 0.78 acres, listed at $439,900. It has 1,792 square feet, three bedrooms, two full bathrooms and one half bathroom, a fireplaced living room, a finished lower level with a second brick fireplace and an under-house garage. It has been on Zillow for 13 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.
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