WOODBURY, CT — Woodbury's for-sale market right now spans more than 300 years of history, from a home built in 1685 to a working equestrian facility to a lakefront retreat on Lake Quassapaug, according to Zillow.com. Here's a look at the five most expensive homes on the market in town right now.
No. 1 on the list, by a wide margin, is 920 Main Street South, listed at $2,995,000. Known as "Warren's Landing on the Pomperaug," the 5,316-square-foot Greek Revival estate was built in 1890 and sits on 18.23 acres along the Pomperaug River. It has 4 bedrooms, 4 full bathrooms and 2 half bathrooms, four fireplaces, a six-barn complex with a retail shop and pool cabana, and a newly built gunite pool. It has been on the market for 89 days.
Just behind it is 112 West Lake Road, priced at $1,795,000. It's a 1,197-square-foot lakefront retreat on Lake Quassapaug, built in 1955 and renovated in 2020, with 2 bedrooms and 2 full bathrooms, a private beach and dock, and a renovated lakeside cabana. The town of Woodbury classifies it and a handful of neighboring properties as condominiums even though it functions as a standalone lakefront home. It has been on the market for 81 days.
Rounding out the top three is 55 Good Hill Road, listed at $1,790,000. Built in 1685, it's one of the oldest continuously inhabited homes in the county, with 3,324 square feet, 4 bedrooms, 4 full bathrooms and a half bathroom, hand-hewn beams and a historic cooking fireplace, plus a pool, cabana and two barns on 3.67 acres. It has been on the market for 191 days after a $205,000 price cut on Aug. 24.
No. 4 is 138 Minortown Road, priced at $1,600,000. It's a turnkey equestrian facility on 21.68 acres, built in 1978, with a 4-bedroom, 2.5-bathroom colonial spanning 3,122 square feet, 21 horse stalls, a heated indoor riding arena and a 2-bedroom apartment above the garage. It has been on the market for 24 days.
Closing out the top five is 40 Ruffin Road, listed at $1,590,000. Built in 1881 on 6.3 acres at the end of a private lane, the 2,732-square-foot home has 4 bedrooms, 2 full bathrooms and a half bathroom, a primary suite with views of Perkins Ponds, an inground pool and a two-story pole barn. It has been on the market for 82 days after a $200,000 price cut on Aug. 31.
Prices, square footage and days on market reflect Zillow.com listings as of Sept. 9, 2026, and are subject to change.
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