106 Tennessee Ave S

This beautifully renovated 3-bed, 2-bath apartment sits above one of the town’s most recognizable commercial blocks—a place that has welcomed locals and tourists alike. Whether you choose to make this your own home or continue using it as an income-producing rental, the space feels warm, inviting, and full of character. Large windows look out over downtown, and the thoughtful updates make it easy to move right in or start renting from day one. But what truly sets this property apart is the story it tells. This apartment is part of a four-parcel collection that once housed Boots and Brews—a beloved downtown hangout known for its ice cream parlor, bar, axe-throwing lanes, mechanical bull room, and even a hidden speakeasy. Every corner of this block carries a little piece of Cowan’s personality, and now it’s ready for its next chapter. For an investor, this is a rare chance to own a mixed-use block with built-in foot traffic and multiple revenue possibilities. For a homeowner, it’s an opportunity to live downtown with walkable access to shops, restaurants, and community events. And for anyone dreaming of reviving a unique entertainment venue or launching something new, the potential here is tremendous. Cowan’s central location puts you minutes from Decherd, Winchester, and Sewanee—making it a natural stop for both locals and visitors exploring the surrounding area. If you’re drawn to properties with history, character, and unreal potential, this one is worth a look.