This beautifully maintained 1920s building is located in the heart of downtown Bennington. Lovingly cared for and meticulously maintained, 211 School Street is ready for the next entrepreneur, medical professional, or visionary to make it their own. For decades, the main level operated as a successful orthodontic office and its layout still lends itself perfectly to a range of professional or commercial uses. The first floor features a welcoming reception and waiting area, several patient rooms, functional workspaces, a private office, and a convenient 1/2 bath. The thoughtful design makes it ideal for health and wellness practices, boutique businesses, or creative studios. Upstairs, a bright and inviting 2BR/1BA apartment offers additional value and flexibility. Complete with a full kitchen and laundry hookups, the apartment has its own separate entrance making it perfect for owner-occupancy, short-term rental, or steady long-term income. Just a block away from shops, cafs, and restaurants, this property enjoys all the benefits of downtown convenience while being tucked away on a quieter street, ideal for clients seeking discretion or professionals who value a peaceful setting. The building is impeccable with a dry basement and generous parking for clients or tenants. With multiple permitted uses, this is a rare opportunity to live upstairs while running your business below, or to invest in a versatile, income-producing property in Bennington's thriving downtown!