FAIRFIELD, CT — A $25 million estate on Long Island Sound tops Fairfield's most expensive homes for sale, and the No. 2 listing on Zillow.com has a Broadway pedigree: it was once the home of Richard Rodgers, who wrote the music for "The Sound of Music."
No. 1 on the list is Sasco Point, at the end of 1131 Sasco Hill Road, asking $25,000,000. The 2002 house blends Swedish, Dutch and Moorish influences, according to the listing, and sits behind a gated entrance on 11.12 acres with 450 feet directly on the Sound. It has 19,569 square feet, six bedrooms, seven full bathrooms and four half bathrooms, along with a new pool, a birch garden, a private dock and a new multi-car garage with an art studio upstairs. It has been on Zillow for 564 days.
Just behind it is the former Rodgers home at 4800 Congress St., listed at $9,975,000 after a $2 million price cut on Oct. 5. The 1965 modern house on 10.92 acres was recently renovated and expanded for one-floor living, with skylights, walls of glass, a hidden screening room, a Moroccan lounge and a guest wing. It has seven bedrooms, seven full bathrooms and three half bathrooms; Zillow doesn't list its square footage. A barn pool house holds a kitchen and a gym, and the grounds include an office pavilion, an orchard and high stone walls next to a nature preserve. It has been on Zillow for 160 days.
Rounding out the top three is a stone-and-stucco house to be built by Coastal Luxury Homes at 640 Hulls Farm Road in Southport, listed at $8,696,000. Construction begins in April, according to the listing. The 8,559-square-foot plan on 2 acres has seven bedrooms, six full bathrooms and two half bathrooms. It has been on Zillow for 220 days.
No. 4 is 541 Sasco Hill Road, a 1931 estate behind iron gates flanked by stone lions, listed 11 days ago at $6,500,000. The 11,999-square-foot house spans four levels and has five bedrooms, six full bathrooms and three half bathrooms on 1.25 acres, plus a heated pool and spa, an outdoor kitchen and an apartment above the garage that has been roughed in.
Closing out the top five is a beachfront property on Long Island Sound at 1859 Fairfield Beach Road, at $6,499,000. The sale covers two parcels, 1845 and 1859 Fairfield Beach Road, totaling 0.55 acres with nearly 100 feet of beach. The 1992 main house has 3,511 square feet, four bedrooms, four full bathrooms and one half bathroom. It has been on Zillow for 33 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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