Middleton Homes For Sale

Middleton was first settled by English colonists in 1659 and officially incorporated as a town in 1728, carved from portions of Salem, Topsfield, Boxford, and Andover. Its very name reflects its origin story: the town sits roughly midway between the important early Massachusetts settlements of Salem and Andover. The Ipswich River winds through the town center, and that river — along with Middleton Pond — has shaped both the town's early mill economy and its present-day character as a wooded, low-density North Shore community.

Middleton's historic character survives in a handful of well-preserved landmarks: the Thomas Fuller House, built in 1684, and the Deacon Edward Putnam Jr. House recall the town's earliest colonial families, while the Richardsonian Romanesque Flint Public Library — funded by a bequest from Charles L. Flint and opened in 1891 — was listed on the National Register of Historic Places in 2002. One of Massachusetts's oldest trees, an oak estimated at roughly 400 years old, still stands on Peabody Street. In 1969, Robert Trent Jones designed the championship 18-hole course at Ferncroft Country Club, which spans 287 acres across Middleton and neighboring Topsfield and hosted the LPGA's Boston Five Classic from 1980 to 1990.

Today Middleton remains a small, largely residential town of roughly 14 square miles with no municipal sewer system (all properties rely on private septic) and no MBTA commuter rail stop of its own — a point of local debate, since the town rejected MBTA Communities Act (Section 3A) multifamily zoning at town meetings in 2024 and, as of early 2026, remains one of a small number of Massachusetts communities still formally noncompliant, having lost a $2 million MassWorks grant and appealed the mandate to the Massachusetts Supreme Judicial Court. That low-density, semi-rural character keeps demand strong: as of May 2026, Redfin reported a median home sale price of $814,513 in Middleton, up 4.8% year-over-year.