Nestled along the Pleasant River in Windham, Maine, Humphrey’s Farm carries a story that began more than two centuries ago. The land was first purchased in 1763 by Dr. Humphrey Devereaux, a physician from Marblehead, Massachusetts, who became one of Windham’s earliest settlers. His 100-acre parcel, known as Lot 115, was part of what was once called “New Marblehead,” the town’s original name.

In 1795, the property passed to James and Elizabeth Bolton, who are believed to have built the original Federal-style farmhouse — a simple yet elegant structure with twin fireplaces, wide pine floors, and a strong fieldstone foundation. Over the generations, the home was expanded, refined, and passed through the hands of several notable Maine families, including the Smalls and Mayberrys, each adding layers of character and craftsmanship that endure to this day.

 

In June 2024, the property found its newest stewards, Ronnie and Nichole Lessard, who renamed it Humphrey’s Farm in honor of its founding owner. The Lessards have lovingly renewed the home, blending its timeless architecture with fresh life and modern hospitality. Their renovations include a large, renovated kitchen designed for gatherings, a sparkling inground pool and pool house, and lush new gardens that echo the beauty of Maine’s natural landscape.

 

Today, Humphrey’s Farm stands as a place where history and celebration meet — a venue that honors its 18th-century roots while opening its doors to new stories and shared joy. From the sweeping grounds to the warmth of the farmhouse itself, every corner of Humphrey’s Farm invites guests to experience something rare and meaningful — a celebration of love, community, and the enduring spirit of Maine.