Bethany's 5 Priciest Homes On The Market Right Now

BETHANY, CT — The most expensive home for sale in Bethany is a horse property where you can ride straight from the yard onto miles of trails, according to listings on Zillow.com. Two houses each on Judd Hill Road and Wooding Hill Road fill out the rest of the list.

No. 1 on the list is 395 Sperry Road, listed at $1,375,000 after a $124,000 price cut on Sept. 29. The 1997 house has 4,008 square feet, four bedrooms, three full bathrooms and one half bathroom on 7.3 acres. The listing pitches it to riders who want to saddle up at home and head out on the trails, and highlights a welcoming front porch, dormer rooflines, a cupola-topped garage and multiple fireplaces. It has been on Zillow for 137 days.

Just behind it is 35 Judd Hill Road, a 2002 Colonial on a quiet cul-de-sac, listed at $1,300,000. Zillow lists four bedrooms, four full bathrooms and one half bathroom in 4,353 square feet on 2.45 acres; the listing calls it a four- to five-bedroom home. A two-story foyer with marble floors leads to a chef's kitchen with a six-burner Bertazzoni gas range, a center island and a wine cooler. It has been on Zillow for 13 days.

Rounding out the top three is 24 Judd Hill Road, a 2004 house on 2.59 wooded acres that its original owner has kept for 19 years, according to the listing. It's listed at $975,000. The 4,364-square-foot home has four bedrooms, four full bathrooms and two half bathrooms, an open-concept main level, hardwood floors throughout and a family room with a fireplace. It has been on Zillow for 38 days.

No. 4 is 298 Wooding Hill Road, a new-construction Colonial listed at $950,000 that is still being built; the listing says its photos will be updated monthly. Plans call for 3,277 square feet with four bedrooms, three full bathrooms and one half bathroom on 1.28 acres, with hardwood floors, solid wood interior doors and recessed LED lighting. It has been on Zillow for eight days.

Closing out the top five is 285 Wooding Hill Road, a 1979 house on 4.56 acres with a brook, listed at $749,000 after a $30,000 price cut on Sept. 7. The 2,642-square-foot home has four bedrooms and three full bathrooms, with hand-hewn beams, wide plank floors and a kitchen renovated top to bottom in 2019. It has been on Zillow for 125 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.