Searching for a classic Vermont farmhouse offering endless possibilities? You have just found it! Welcome to 183 Pleasant St. a quaint Victorian home in the vibrant town of Chester VT. Enter through a large mudroom, perfect for ski and board storage. The first floor boasts an eat-in kitchen with a new refrigerator, a pantry/laundry room combo recently updated, a formal dining room complete with a pellet stove for cozy winter dinners, a living room, and a bedroom with an ensuite half bath. Ascend the staircase in the formal entryway to the second floor to find three additional bedrooms, two full baths, two huge bonus rooms, and a walk-in closet/storage space. Continue down the back steps that bring you to the mudroom and enter the huge 1600 sq ft semi-finished two-story barn that is perfect for a workshop, artist studio, or storage OR finish the space for more living space, in-law suite, or rental property. Set on a flat.55 acres at the edge of town, lawn care is a breeze and there is a newer stone firepit and tons of room for gardening or activities. Walk to the village green, the local swimming hole, and Chester schools. This location is also ideal for ski and board enthusiasts, close to Okemo and Magic (20 mins), Bromley (30 mins), Killington (40 mins), and Snow (50 mins). Did we mention fiber optic internet, allowing lightning-fast speed to work from home? This expansive home would be perfect for a primary residence, vacation home, or investment. Move-in ready!