Newly updated! A rare offering in Charlottesville's beloved Frys Spring neighborhood; a beautifully updated nineteen twenties home on one acre within city limits, featuring a thoughtfully designed addition, a detached income-generating cottage, and a detached two-car garage with loft and office space. Lush, mature landscaping provides privacy and year-round color, with dedicated garden space and off-street parking for four or more vehicles. The main house retains its original hardwood floors throughout, paired with a newly added gourmet kitchen appointed with quartz countertops, freshly painted white cabinetry, and high-end KitchenAid appliances. A generous living room with gas fireplace opens to a formal dining room with incredible views of the lush back yard. The new main-level primary suite offers single-floor living with a spa-inspired bath, custom walk-in closet, and screened porch access. Four additional bedrooms on the upper level share a full hall bathroom. The detached two-car garage includes a ground-floor office and workout space, half bathroom, and loft. The private two-bedroom cottage with kitchenette, full bathroom, living room, and newly refinished hardwood floors offers immediate income potential or flexible guest accommodations.