26905 Main Rd, Southold, NY 11935

Description

26905 Main Rd aka 115 Highland Rd. A rare opportunity to own a remarkable piece of history, this beautifully preserved residence seamlessly blends Colonial origins with timeless Georgian elegance. Originally built circa 1770, the home has evolved through generations of thoughtful additions and renovations while retaining its extraordinary architectural character.

The gracious center hall floor plan welcomes you with a historic staircase and spacious rooms filled with period charm. A stunning 14 x 25 country kitchen, added around 1820, features soaring cathedral ceilings, a loft overlooking the space, ample room for everyday dining, and direct access to a private terrace—perfect for entertaining or enjoying peaceful mornings outdoors.

Historic details abound throughout the home, including exposed hand-hewn oak beams in the formal dining room, exceptionally wide-plank wood floors measuring up to 18 inches on the second level, elegant period moldings, and beautiful marble fireplaces. A major Georgian-style renovation completed between 1850 and 1860 introduced the stately entrance portico, the full two-story roofline, and the impressive 40-inch-wide staircase, enhancing both the home’s beauty and functionality.

Offering four bedrooms and two full bathrooms—one on each level—the home combines historic craftsmanship with comfortable everyday living.

Complementing the residence is a carriage barn-style garage, built in 2003, featuring space for three vehicles, a spacious second-floor loft ideal for a studio, workshop, storage, or future possibilities, plus an attached tool shed.

Situated on a generously sized parcel with .93 acres, the property is framed by mature trees that provide privacy while the expansive lawn offers endless opportunities for gardening, recreation, entertaining, or future enhancements.

Rich in history, craftsmanship, and character, this one-of-a-kind property offers the rare chance to own a home where over 250 years of architectural heritage meet the comforts of modern living.