SIMSBURY, CT — Nothing for sale in Simsbury right now tops $1 million, but the town's five priciest homes on Zillow.com still offer plenty: a pond, a 14-acre estate on the Metacomet Ridge, a 19th-century farm and a deal that comes with two houses and a set of historic barns.
No. 1 on the list is 10 Whitman Pond Road, a custom Colonial on a pond, asking $999,000 after a $76,000 price cut on Oct. 23. Built in 1992, the 5,418-square-foot house has four bedrooms, four full bathrooms and two half bathrooms on 2.23 acres on a cul-de-sac. The family room has a two-story fireplace and a floor-to-ceiling window, and there's a butler's pantry, a wood-paneled screened porch, and a new composite deck. Zillow shows it has been listed for two days.
Just behind it is what the listing calls the Metacomet Ridge Estate at 2 Quarry Road, listed at $975,000. Most of the value is in the land: 14.74 acres with a private pond, a 60-by-25-foot open pole barn and a garage, which the listing pitches for a hobby farm or horses. The house, built in 1917, has 2,432 square feet, four bedrooms, and two full bathrooms. It has been on Zillow for 32 days.
Rounding out the top three is 15 Sand Hill Road in Weatogue, at $951,000. The listing says most of the 4,883-square-foot house was built in 2004 on a 1975 original. It has eight bedrooms, seven full bathrooms, and one half bathroom on 0.92 acres. The kitchen, by Soraghan, has a Sub-Zero refrigerator, a six-burner Wolf cooktop, and two islands, and two of the bedrooms have private entrances. It has been on Zillow for 178 days.
No. 4 is a farm on 500 Firetown Road, asking $919,000. The farmhouse dates to 1862 and has 2,671 square feet, four bedrooms, two full bathrooms and one half bathroom on 3.24 acres, with front and back staircases, a screened porch, bluestone patios, a firepit and outbuildings surrounded by pastoral views. It has been on Zillow for 26 days.
Closing out the top five is a three-parcel package at 66 Hartford Road, listed at $800,000. The sale includes 66, 68, and 72 Hartford Road: two Colonial homes and a lot with historic post-and-beam barns, almost 3 acres in all. Zillow lists the combined 3,656 square feet with eight bedrooms, five full bathrooms, and one half bathroom, and the oldest part dates to 1853. It has been on Zillow for 31 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, and land-only listings were left out.
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