This is not your typical two-for-one deal!! Rare opportunity to own two historic homes side-by-side as one property! Providing character with modern versatility, these beautifully maintained residences offer endless possibilities for multi-generational living, rental income, investment or owner-occupancy. The first home, 100 E High Street, offers over 1,900 square feet and is zoned commercial/residential which creates opportunities for an Airbnb, home business, office space, boutique retail or traditional residential use. Inside, you'll find 3-4 bedrooms and two full baths, including a convenient first-floor bedroom. The spacious kitchen features a stunning oversized window overlooking the private courtyard, bringing natural light into the heart of the home. 104 E High Street boasts over 2,100 square feet of living space and is filled with charm and flexibility. Features include a first-floor den, generous living areas and a large third-floor room that could easily be a fourth bedroom, studio, office or flex space. Step outside to enjoy the covered pavilion, perfect for entertaining family and friends throughout the seasons. Both properties are enhanced by extensive landscaping, creating beautiful outdoor spaces to relax and enjoy. Deeded off-street parking adds convenience, while the unique combination of two historic homes opens the door to many possibilities. Whether you're seeking an investment opportunity, income-producing property, or a one-of-a-kind place to call home, this offering should not be missed!