MILFORD, CT — Every one of Milford's five most expensive homes for sale on Zillow.com is near the water, and the priciest has a view that can never be built over: a public park sits permanently between it and Long Island Sound.
No. 1 on the list is 40 Hawley Ave. in Woodmont, asking $2,890,000. Trubee Doolittle Park lies between the house and the Sound, so the listing promises panoramic water views that future development can't block. Built in 2014 and perched 43 feet above sea level, the 4,092-square-foot house is in FEMA's Zone X, so no flood insurance is required, according to the listing. It has four bedrooms and four full bathrooms, geothermal heating and cooling and solar power. It has been on Zillow for 156 days.
Just behind it is 33 Pearl St., a 2020 house a block from Silver Sands State Park and the boardwalk, at $1,599,000. The 2,564-square-foot home has three bedrooms, two full bathrooms and one half bathroom, a great room with a floor-to-ceiling fireplace and live-edge mantel, a front balcony and a rear deck. It has been on Zillow for 168 days.
Rounding out the top three is 125 Ridgewood Drive, rebuilt in 2023 around its original stone fireplace and listed at $1,499,000 after a $76,000 price cut on Sept. 14. The 3,861-square-foot house has five bedrooms and four full bathrooms and is steps from bluffs over the Sound with water access for swimming and kayaking. It has been on Zillow for 107 days.
No. 4 is 114 Merwin Ave., a 2023 house with ocean views in front and a pond out back, listed at $1,460,000. The 3,209-square-foot home has three bedrooms, three full bathrooms and one half bathroom, 9-foot ceilings, a kitchen island 9 feet long, heated floors in the primary bath and a third-floor retreat. It has been on Zillow for 40 days.
Closing out the top five is a year-round waterfront cottage at the end of a dead-end street, 138 Shorefront St., listed at $1,449,900 after a $50,100 price cut on Oct. 24. The 1890 house has 1,570 square feet, three bedrooms and two full bathrooms, plus a fireplace and unobstructed views of the Sound and Charles Island. It has been on Zillow for 38 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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