Nestled on one of the most coveted streets in the Los Gatos Mountains, Loma Prieta Ave., this property makes its debut on the market for the first time since its acquisition in the late 1800s. Encompassing 6.48 acres of picturesque land, it presents an idyllic canvas for a vineyard enthusiast, complemented by a serene hiking trail that winds through its breathtaking landscape. The expansive main house, gracing the estate, features 3 bedrooms, an office, and 3 full bathrooms & a 1/2 bath, 3,645 sq.ft,, offering ample space for comfortable living and entertaining. Step into the heart of the home, where a gourmet kitchen awaits, meticulously designed and equipped with high-end appliances, custom cabinetry, and elegant finishes. Ideal for hosting gatherings, the property boasts an expansive deck and pool area where guests can bask in the tranquility of the surroundings. Additionally, a separate beautifully updated 3 bedroomsv+office, 2.5 bathroom, 2305 sq. ft. guest house on the grounds offers an enticing opportunity for rental income or as a private retreat for guests, further enriching the property's allure and potential. Award-winning Los Gatos Schools, Loma Prieta Elementary, C.T. English Middle School, Los Gatos High. Served by Comcast Internet.