MIDDLETOWN, CT — A log home on nearly 40 acres tops the list of Middletown's most expensive homes for sale. Leaving aside the apartment buildings at the top of the city's market, the five priciest homes on Zillow.com also include a modern farmhouse with its own waterfall and a house beside the Mount Higby Reservoir.
No. 1 on the list is 1409 Millbrook Road, a custom log home on 39.36 acres with panoramic views, asking $1,295,000. Built in 2005 with an addition in 2014, the 2,656-square-foot house has four bedrooms, three full bathrooms and one half bathroom, according to Zillow, although the description mentions three full bathrooms only. It has cathedral ceilings, a two-sided fireplace, German-made windows with roll shutters and two oversized garages on the lower level. The land is three separately deeded parcels with rolling acreage and a man-made pond. It has been on Zillow for 119 days.
Just behind it is new construction at 145 Monarca Drive, a modern farmhouse-style ranch listed at $1,200,000. It sits on 2.38 acres at the end of a cul-de-sac on a private road, where stone walls line a circular drive with a waterfall feature. The 3,456-square-foot house has three bedrooms, three full bathrooms and one half bathroom, board-and-batten siding, black windows, a front door custom-built on site and 10-foot garage doors. It has been on Zillow for 59 days.
Rounding out the top three is 49 Partridge Lane, on a cul-de-sac next to the Mount Higby Reservoir, at $898,000 after a $50,000 price cut on Aug. 25. Built in 1991, the 4,234-square-foot house has four bedrooms, three full bathrooms and two half bathrooms on 3.23 acres, with Viking appliances in the kitchen. It has been on Zillow for 118 days.
No. 4 is a new modern Colonial under construction at 85 Freeman Road, due to be finished in mid-November and listed at $749,900. The 2,232-square-foot house sits on 1.8 acres of rolling hills and has four bedrooms, two full bathrooms and one half bathroom, white oak floors, quartz counters and a Trex front porch. It has been on Zillow for 53 days.
Closing out the top five is a new single-level home at Founders' Ridge, a 55-and-over community in the Westfield section: 41 Webster Lane, Unit 2-145, asking $689,000. The 1,555-square-foot Kirby II model has two bedrooms and two full bathrooms, quartz counters and a walk-in pantry, and it's ready for immediate occupancy. 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 offered as new construction were included; pending, coming-soon, land-only and multifamily listings were left out. The city's three priciest listings, multifamily buildings on East Main, Main and Portland streets, were among those left out.
Sign up for free local newsletters and alerts for the
Middletown Patch
Patch.com is the nationwide leader in hyperlocal news.
Visit Patch.com to find your town today.