Countless historic buildings and homes paint New England’s landscape with unparalleled picture-perfect charm.  From old farm houses and barns, to elegant Victorians and Colonial homes, with the founding of each small town or village came the foundation of a freshly constructed home with roots that certainly run deep.

Here are three residences that emerged with the establishment of their town, each constructed and owned by prominent, local founding fathers and town residents of their day.

566 Boston Post Road—Madison, CT

Out on the beautiful coastline of Connecticut rests a Colonial saltbox style residence long-believed to be Madison’s oldest home.  The landmark property, now for sale and listed by Madison agent Margaret Muir for $729,000, was said for years to be built in 1675, although recent research reveals the possibility of the home having been constructed circa 1720.  Located on 1.3 acres of land across from the Town Green, this period residence represents a true piece of New England history.  Previously owned by the locally prominent Dudley family, the home once operated as a tavern, where, in 1776, General George Washington was served what was reputedly known as the best food in the area known then as “East Guilford.”

Over the generations, the 2,241 square-foot, three-bedroom residence has been preserved to maintain many of its original features including fireplaces, corner cupboards, wide plank floors, paneling, beams, hand-wrought hardware and more. While authentically antique in style, the white, wood-roofed house is also highly adaptable and livable for modern use.

75 Meadow Street—Winsted, CT

A Victorian home in Winsted, CT, built in 1849 by the town’s founding father John Hinsdale, is another home full of great history.  The property, which includes an architecturally detailed two-story barn presumably believed to have once been part of the Underground Railroad, is represented by Lakeville agent Gregg Stallings, and offered at $329,000.


Over the years, the quaint home, known as the John Hinsdale House, has been meticulously maintained, with up-to-date features and amenities.  A wraparound porch greets visitors entering the residence, where one will find a total of ten rooms, with five bedrooms and two baths.  Its historic barn is currently zoned for commercial use, offering opportunities for studio space, an art gallery, antique store and more.  Neighborhood residents even choose to start and end all community parades at this notable Winsted property, highlighting its undeniable landmark in the town.

1 Buffington Road—Worthington, MA

The Jonathan Woodbridge House, a stunning, high-style Georgian-Federal mansion, has proudly stood since 1806 in the village of Worthington, located in the eastern Berkshire foothills. The home, which is now for sale and listed by Great Barrington agents Gladys Montgomery and Jeff Loholdt for $795,000, was constructed by Jonathan Woodbridge, a Berkshire native and the grandson of fire-and-brimstone Puritan preacher Jonathan Edwards.  As a prominent town member, Woodbridge was the driving force behind many early town developments, and his sophisticated eye for construction is evident through this home’s exquisite Georgian-Federal design and preserved original features.


General Marquis de Lafayette, a key individual in obtaining French support for the American colonies, even visited the house during his tour of the United States in 1824.  It’s no wonder why this incredible estate is listed in the National Register of Historic Places, distinguished as being one of the most-well documented homes in the Historic American Buildings Survey of the U.S. Library of Congress—a home whose links to the area’s founding fathers, as well as overall American history, are well worth preserving.

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