If you've been struggling to find the balance between retaining privacy while also being in town, then it's time to take a look at 37 Jackson Ave! This 2 Bedroom, 1 Bathroom home on the outskirts of downtown Winchester is ready for your personal touches. Rooms have been emptied, walls and trims have been painted, and the porches are ready to see entertaining again. Hardwood floors flow in and out of this 1940s home in the abundance of natural sunlight, from the spacious Living Room right into a Main Level Bedroom. A Full Bath sits adjacent to this Bedroom with the Kitchen and a "Bonus Room" that could be used for a Dining Space, Breakfast Nook, Den, etc. right around the corner for convenient one-level living. In addition, you'll find another Bedroom upstairs with TWO additional spaces attached! Whether you've been needing that Walk-In Closet, Office, or Studio, this home provides options galore. The Unfinished Basement provides two separate rooms for storage or other, as well as Washer and Dryer hookups. Your mornings can start with coffee on your large Front Porch and end in the Back Yard oasis with your favorite people or pets, surrounded by a fenced in Back Yard with a fish pond and several fruit trees! In case you need additional storage space, a Shed is already here and there's even a Detached Garage. Explore spacious living in the city at 37 Jackson Ave!