Property Details

Welcome to what many know as *The Jewel of Winchester* - a landmark stone century home offering exceptional scale, flexibility, and opportunity in the heart of town. Built in 1885 and situated on an extraordinary 203 x 114 ft lot, this iconic property combines historic charm with possibilities rarely found within town limits. Offering over 3,800 sq ft above grade, the home features 4 bedrooms, 2.5 bathrooms, generous living spaces, and architectural character that has stood the test of time. A rare and valuable feature of this property is its split zoning configuration, creating unique flexibility for future owners (buyers to confirm intended use). Formerly operated as a bed and breakfast, the property offers a layout and setting that naturally lend themselves to a variety of possibilities while functioning beautifully as an exceptional residence. The main floor includes a bedroom with ensuite and private exterior entrance - ideal for multi-generational living, guest accommodations, professional office space, or a flexible work-from-home setup. Outside, the opportunities continue with extensive parking and impressive outbuildings including a heated 50' x 24' shop and an additional 50' x 30' building with oversized bays. Whether for hobbies, storage, workspace, future income potential, or entrepreneurial pursuits, this type of space is increasingly difficult to find. Not to be overlooked are the impressive gardens and grounds flanking the north west side of the property, featuring a beautiful permanent gazebo structure, a great place for an afternoon tea, perhaps? Imagine a boutique wellness space, professional office, studio, expanded hospitality concept, workshop environment, or simply enjoying one of Winchester's most distinctive homes as your own private residence. Rich in history. Rare in opportunity. Endless in possibility. A truly special offering in the heart of Winchester.