PORTLAND, CT — None of Portland's most expensive homes for sale tops $600,000, and No. 1 is a hilltop house with views the listing puts at more than 30 miles, according to Zillow.com.
No. 1 on the list is a 2002 house at an undisclosed address in Portland, listed at $580,000. It has 3,427 square feet, three bedrooms, three full bathrooms and one half bathroom on 1.32 acres, an open-concept design, a primary bath remodeled in 2020 and a kitchen from 2021. It has been on Zillow for 10 days.
Just behind it is 726 William St. Extension, a 1965 raised ranch listed at $539,900 after a $10,000 price cut on Oct. 26. Zillow lists four bedrooms and two full bathrooms in 2,288 square feet on 0.6 acres; the listing counts a fifth bedroom on the lower level. It has a living room with a wood fireplace and a bay window, and a lower-level den with another fireplace. It has been on Zillow for 10 days.
Rounding out the top three is 18 Michele Drive, a 1974 Colonial with a pool, listed at $525,000. It has 2,138 square feet, four bedrooms, two full bathrooms and one half bathroom on 1 acre, a remodeled eat-in kitchen and a family room with a pellet stove. It has been on Zillow for three days.
No. 4 is 57 Summer St., a 10-room 1995 ranch listed at $499,900. It has 4,390 square feet, four bedrooms, three full bathrooms and one half bathroom on 1.2 acres and a full basement, and the listing pitches it to a buyer ready to bring their own vision. It has been on Zillow for 136 days.
Closing out the top five is 132 Pepperidge Road, a 1969 house cared for by its original owners, listed at $460,000 after a $25,000 price cut on Oct. 15. It has 2,223 square feet, four bedrooms, one full bathroom and one half bathroom on 1.06 acres, hardwood floors and a living room with a fireplace. It has been on Zillow for 18 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.
Sign up for free local newsletters and alerts for the
East Hampton Patch
Patch.com is the nationwide leader in hyperlocal news.
Visit Patch.com to find your town today.