DURHAM, CT — Two farms on Wallingford Road, together covering more than 400 acres, top the list of Durham's most expensive homes for sale on Zillow.com. An 18th-century saltbox restored by The 18th Century Company closes out the top five.
No. 1 on the list is 153 Wallingford Road, a farm complex listed at $2,800,000 that the listing says has been operating for more than 100 years. Zillow lists 273.52 acres, which the listing rounds to nearly 280, with a pond, pasture, rolling hills and stalls for more than 40 horses, including a two-story horse barn. The price covers five houses, two used by the current owners and three rented out, and the listing pitches it to multigenerational owners or an investor. Zillow combines them into 10,623 square feet with 15 bedrooms, seven full bathrooms and one half bathroom, while the listing counts 22 bedrooms across the five houses. It has been on Zillow for 776 days.
Just behind it is 148 Wallingford Road, which the listing calls the Greenbacker's Brookfield Farm, listed at $1,999,000. The 141-acre farm has two houses, a dairy barn and other outbuildings, and the listing says about 92 acres of cropland and 20 acres of pasture are leased to other farmers, with more income from Durham Fair parking and a hunt club lease. Zillow lists a 1916 house with 3,308 square feet, seven bedrooms, two full bathrooms and one half bathroom. It has also been on Zillow for 776 days.
Rounding out the top three is 29 Casa Lane, a 1996 modern country Colonial in a neighborhood with underground utilities, listed at $999,000. The 4,490-square-foot house has four bedrooms, three full bathrooms and one half bathroom on 1.62 acres, with a chef's kitchen that has a cherry and granite island, a butler's pantry and a Wolf induction range, plus a stone fireplace with a wood stove. It has been on Zillow for 35 days.
No. 4 is 100-R Foot Hills Road, a private country estate listed at $995,000 after a $55,000 price cut on Oct. 4. Of its 25.17 acres of pasture and woods, about 9.17 are in Durham and the rest are in neighboring Haddam, according to the listing. The 1996 house has 3,474 square feet, three bedrooms, three full bathrooms and one half bathroom, and has been on Zillow for 54 days.
Closing out the top five is 64 Haddam Quarter Road, the Samuel Fairchild House, which the listing dates to about 1727, listed at $899,900. Restored by The 18th Century Company, it keeps its raised paneling, chamfered summer beam, wide board floors, original doors and hardware, original front staircase and five fireplaces, two with bake ovens. The current owner built a bar in the old kitchen from wood found on the property. The 3,306-square-foot house has four bedrooms, two full bathrooms and one half bathroom on 3.54 acres and has been on Zillow for 54 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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