Welcome to 99 Acorn Lane, a desirable Southport address set on a quiet cul-de-sac just minutes to Westport, Southport Village, and Downtown Fairfield. This expanded Cape sits on 1.24 beautiful acres, offering privacy within a charming neighborhood and ample opportunity for expansion or a pool, subject to approvals. Thoughtfully upgraded, the home offers more than 3,000 square feet of flexible living space with 4 bedrooms, 3.5 baths, 2 fireplaces, and hardwood floors through most of the house. The main level is the heart of the home, with an inviting open layout, soaring ceilings, and an eat-in kitchen overlooking two spacious living areas with fireplaces. A pretty dining room, with oversized windows, is currently used as a study. A first-floor primary suite features a walk-in closet and full bath, while the second floor includes two additional bedrooms and a shared bath. Above the garage, a bonus bedroom with full bath offers flexible space for guests or work. A screened porch overlooks the property for enjoying warmer months. At the cul-de-sac, Aspetuck Land Trust's Acorn Lane Upland Preserve offers wooded trails connecting to Fairfield's Mill Hill Open Space. A rare Southport opportunity with space, charm, and convenience.