Inside Five of the Most Storied Homes on the Market Right Now

Every historic home has a story. Some were shaped by influential families, others welcomed notable guests, and a few have been carefully preserved using the same techniques that built them centuries ago. Here are five properties where history is woven into everyday life. 

Waterman Farm: Restored from the Land Itself 

Waterman Farm dates to the late 1700s and has long been part of North Haven’s farming heritage. During its recent restoration, the owners harvested trees from the property and milled them in the estate’s own historic sawmill to repair the original buildings—a rare approach that preserved the farm using materials from the land itself. 

1816 Morgan Horse Farm Road: A Vermont Landmark Since 1825 

Built in 1825 by Asaph Drake, this distinguished Federal home has ties to Vermont’s renowned Morgan Horse Farm and was later owned by a Middlebury College president. Nearly 200 years later, it remains listed on the National Register of Historic Places. Thoughtfully renovated in recent years, the home now blends original pumpkin pine floors, historic brickwork, and other period details with carefully considered updates. 
 

The Margaret Cummings Estate: A Grand Beginning  

This 1909 Tudor Revival residence was designed by noted architect Charles Cummings for his sister, Margaret, as part of the original 571-acre Coolidge Estate. Today, more than 500 surrounding acres are protected by the Essex County Greenbelt, preserving the landscape that first inspired The Margaret Cummings Estate.

Blueberry Hill: A Gathering Place for Icons 

Built in 1782 for prominent shipbuilder Stephen Perkins, Blueberry Hill later became the home of internationally acclaimed singer Jane Morgan. During her ownership, the estate welcomed guests including George and Barbara Bush, along with Hollywood legends Joan Fontaine and Myrna Loy. 

Frisky Hill: A Village of Historic Buildings 

Located on 113 acres of land and surrounded by mountain views, Frisky Hill brings together centuries of New England history in one remarkable property. This collection of historic buildings—including a home originally built in Massachusetts in 1665—was carefully dismantled, relocated, and meticulously reconstructed by renowned preservationist Henry Page and a team of master craftsmen. The property includes an original one-room schoolhouse, a historic barn featured on the cover of Pottery Barn, a 41-foot water tower, and a traditional corn crib. 

Whether preserved in place, thoughtfully restored, or carefully relocated, these homes offer more than exceptional architecture. Each reflects a unique chapter of New England’s history and the enduring craftsmanship that continues to define the region.