Zestimates are a reasonable starting point for curiosity, but they’re not a pricing strategy, especially in Fairfield County, CT. The county’s internal price variation is extreme. Homes in Southport, Greenfield Hill, and Grasmere are all within the town of Fairfield, but they can differ by $500,000 or more depending on school assignments, lot characteristics, proximity to the water, and recent updates. Zillow’s algorithm doesn’t know that your kitchen was renovated in 2023, or that your street backs up to a nature preserve, or that the comparable sale down the road had a significantly smaller footprint. A local CMA accounts for all of that. Zestimates don’t, and in a market where the median single-family home in Fairfield County is $1,365,000, the difference between an algorithmic guess and an accurate price can be a very large number.