WOODBURY, CT — An 1890 Greek Revival estate with six barns on the Pomperaug tops Woodbury's most expensive homes for sale, and two of the top five date to the 1700s, according to listings on Zillow.com.
No. 1 on the list is 920 Main St. South, which the listing calls Warren's Landing on the Pomperaug, listed at $2,995,000. The 1890 Greek Revival house has 5,316 square feet, four bedrooms, four full bathrooms, two half bathrooms and four fireplaces on 18.23 acres. The six-barn complex includes a retail shop, equipment storage, a two-car garage and a pool cabana, plus a new temperature-controlled 3,800-square-foot post-and-beam barn. It has been on Zillow for 136 days.
Just behind it is 348 Weekeepeemee Road, a 2004 Colonial set well back from the road, listed at $2,149,900. It has 5,973 square feet, five bedrooms, four full bathrooms and one half bathroom on 9.48 acres, a kitchen that opens to a covered porch overlooking a gunite pool, and garage and barn space the listing pitches to car enthusiasts, including a heated three-car garage. It has been on Zillow for 29 days.
Rounding out the top three is 40 Ruffin Road, a vintage estate at the end of a private lane, listed at $1,590,000 after a $200,000 price cut on Aug. 31. The 1881 house has 2,732 square feet, four bedrooms, two full bathrooms and one half bathroom on 6.3 acres framed by stone walls and gardens, with a two-story pole barn, an in-ground pool, a three-bay garage and a potting shed. Its kitchen has handmade cabinetry, soapstone counters and a Vulcan stove around a brick fireplace. It has been on Zillow for 129 days.
Tied for No. 4 at $1,395,000 each are two 18th-century houses. The first, 509 Weekeepeemee Road, is a 1747 saltbox on 5.19 acres with original wide-plank floors, two fireplaces, twin staircases and a kitchen with Viking appliances; it has 2,346 square feet, three bedrooms, two full bathrooms and one half bathroom and has been on Zillow for 94 days. The second, 30 Hollow Road, is the Jabez Bacon House, built in 1760 and listed on the National Register of Historic Places, according to the listing, which says it has been featured in Early American Life and Historic Homes magazines. It has 4,884 square feet, five bedrooms, four full bathrooms and one half bathroom on 2.24 acres, and its price was cut by $100,000 on Aug. 8. It has been on Zillow for 187 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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