RIDGEFIELD, CT — In a town that sells itself on history, it's fitting that the most expensive listing in Ridgefield right now comes with Main Street's oldest house attached. A pair of side-by-side landmarks downtown tops the list of the five priciest homes for sale in town, according to listings on Zillow.com, followed by a house that hasn't been built yet, a converted Gilded Age carriage house and two estates tied at the same asking price.
No. 1 on the list is a two-house compound at 236 & 250 Main St., listed at $7,995,000. The package includes the Hawley House at 236 Main St., which the listing calls Ridgefield's oldest home, built in 1713 for the Rev. Thomas Hawley, the town's first pastor and town clerk. Next door is 250 Main St., a brightly painted Gothic Revival Victorian built around 1826 by Hawley descendants. The listing says more than $10 million has gone into restoring and updating the properties, which share 3.16 acres and two barns. One barn has an indoor basketball court. The other is a pool and carriage house with a gym and sauna, an arcade, a poker room and a movie theater with more than 30 seats, opening onto a heated saltwater pool and spa. Zillow combines the two houses into 8,934 square feet with eight bedrooms, seven full bathrooms and two half bathrooms. The listing has been on Zillow for 179 days, and the price was cut by $250,000 on Oct. 15. Buyers who want only the Victorian can have it on its own: 250 Main St. is separately listed at $5,495,000 for 5,778 square feet, four bedrooms, four full bathrooms and one half bathroom on 1.94 acres, along with the carriage and pool house.
Just behind it is a house that exists only on paper so far. The new-construction listing at 399 Ridgebury Road is asking $3,600,000 for a proposed 5,000-square-foot home on a 3-acre lot that the listing calls one of the last premier building sites in Ridgefield. Plans show five bedrooms, four full bathrooms and two half bathrooms, with an open floor plan and four or five en-suite bedrooms. It has been on Zillow for 417 days, the longest of any home on this list.
Rounding out the top three is 269 West Lane, a carriage house built by George G. Haven in 1900 for his prize horse, Davey, and its stablemates, according to the listing. It's asking $2,450,000 after a $250,000 price cut on Oct. 15. The renovated 6,671-square-foot home has six bedrooms and six full bathrooms on 2.11 acres. Original herringbone brick floors greet visitors in the entry foyer, and an in-law or caretaker apartment in the rear still has an original horse stall, now a bedroom. The grounds include a gunite pool, fenced perennial gardens and a garden cottage, less than a mile from Ridgefield center. It has been on Zillow for 52 days.
No. 4 and No. 5 are tied at $2,295,000 each. The newer of the two listings, 351 Wilton Road West, has been on Zillow for 17 days. The 5,410-square-foot home has five bedrooms, five full bathrooms and two half bathrooms on 1.43 acres, with a heated pool, a chef's kitchen with a butler's pantry, a library with a fireplace and wet bar, front and rear staircases and an elevator.
Closing out the top five is 351 Old Sib Road, an estate the listing calls "The Retreat." The 5,725-square-foot home has five bedrooms, four full bathrooms and two half bathrooms on 4.39 wooded acres. The walk-out lower level has a full bar, a wine cellar and a cigar room with its own smoke-extraction system. There's also a heated gunite pool, an indoor spa with a hot tub and sauna and a separate cottage with a legal studio apartment. It has been on Zillow for 46 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 available as new construction were included; pending, coming-soon and land-only listings were left out.
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