Welcome to 47 Highland Street, a distinctive turn-of-the-century New Englander offering character, space, and flexibility in the heart of Ashland. With approximately 2,600 square feet of living space, this property presents an exciting opportunity for an owner-occupant, investor, or buyer looking for a property with multiple possibilities. Potential to configure the home as two units: one 2-bedroom, 1-bathroom unit, and one 3 bedroom, 1 bath unit. The property also features a three-story barn, offering additional space and the possibility to explore further uses or expansion, subject to approvals. The barn has been updated and includes a charging station for an electric vehicle. Set on approximately 0.43 acres, the property features a mostly level city lot, paved driveway, attached one-car garage with direct entry and storage above. The yard borders the backside of Ashland Elementary, creating a convenient in-town setting.There is even an electric vehicle charger at barn. Inside, the home offers a mix of classic character and practical updates, including split heating and cooling units throughout, radiator-style wall heaters in the bathrooms, and many updates throughout the property. The sunroom has been updated with new windows, adding comfort and natural light to this inviting space. Public water and sewer, high-speed internet availability, and a convenient Ashland location make this property both comfortable and practical. Located just off Route 3, 47 Highland Street is close to the conveniences of downtown Ashland while offering easy access to the Lakes Region and the surrounding White Mountains. The town beach on Little Squam Lake is just a 5 minute drive. Whether you're looking for an income-producing property, a home with room to grow, or a unique New England property to make your own, 47 Highland Street offers character, flexibility, and opportunity.