This elegant Dutch Colonial, built in 1917, sits 150 feet off the road providing serene privacy & picturesque surroundings. Situated in Fairfield's University area, a short walk to the train, town, public schools, and Fairfield University. Loved by only three owners, this home boasts exquisite craftsmanship: carved fireplace mantels w/dental moldings, plate rails, pocket doors, hardwood floors throughout, & a stunning transom light around the front door. Modern updates blend seamlessly with historical charm. The kitchen opens to the family room & garden room, leading to a beautiful patio & private fenced backyard. The three-story addition allows for a perfect circular flow, ideal for large gatherings. The living room features a fireplace and an adjoining study, one of two potential home offices, the second found on the second floor, complete with its own fireplace. The primary suite boasts a walk-in closet, cathedral ceiling, and private bath. The fully finished third floor, with its private bath & large, light-filled space, serves as a versatile area for teenagers, au pairs, in-laws, or recreation space. Additional features include a 6-zone heat system, replacement windows throughout, two-car detached oversized garage w/attic storage, outdoor shower, & more... The perennial garden that blooms throughout the seasons showcases a stunning array of flowers. The timeless beauty and tranquility found in this home are the essence of 399 N. Benson Rd.