Weston sits in an interesting position within Fairfield County. It’s more affordable than the Gold Coast towns, Westport averages around $2.03M, Darien around $2.36M, and Greenwich around $2.3M, but it commands a meaningful premium over Wilton (approximately $1.25M) and towns further north like Ridgefield (approximately $994K). Weston’s value proposition is a combination of factors: large lots with two-acre zoning in many parts of town, one of the best school districts in the state (Weston High School earned National Blue Ribbon recognition), a rural character that’s genuinely hard to find this close to New York City, and a safety record that has ranked it among the safest communities in the country. For buyers who want space, privacy, and good schools without paying Westport prices, Weston is a compelling alternative, and that sustained demand is a key reason values have held up so well.