Classic character meets thoughtful, long-term investment in this circa-1900 two-story wood-frame home located on charming Chestnut Street in the heart of Red Bank. Offering approximately 1,745 square feet of living space across three floors, this home is complemented by 3 nice-sized bedrooms, 1 full and 1 half bath, hardwood floors, a full 7-foot-high basement, and a rebuilt attic studio that adds flexibility and function. The kitchen features serpentine green marble countertops, a convection oven, and updated refrigerator and dishwasher. The 350-SF attic workspace, rebuilt in 2008, includes a work sink and its own mini-split HVAC system—ideal for a studio, home office, or creative retreat. Over the years, the owner has made substantial structural, mechanical, and exterior improvements, prioritizing durability, efficiency, and peace of mind. Major upgrades include fully renovated front and rear porches, a 12' x 24' detached single-story heated garage, and a 6-inch-thick, 75-foot reinforced concrete driveway. The home is supported by a 200-amp electrical service (2008), high-efficiency gas furnace (2024), new roof (2024), tankless natural gas water heater (2025), and a 20-kW Kohler natural-gas standby generator installed in 2022. The basement has been structurally enhanced with a new 4"- thick reinforced concrete floor slab and 6"- diameter concrete-filled steel Lally columns added in 2025, reinforcing the main support beams. Energy-conscious buyers will appreciate the fully OWNED 12 solar panels installed between 2020-2022 on the garage roof. Adding to the home's appeal is its walkable location- just minutes from the Red Bank train station, downtown restaurants and theaters, as well as easy walking access to St. James Elementary School, Red Bank Catholic High School, and the Red Bank Charter School - offering both convenience and long-term value.This is a home with strong bones, meaningful upgrades, and room for the next owner to add their own vision. Offered strictly "As-is", this property is ideal for buyers who value historic charm, infrastructure investment, and the opportunity to begin their next chapter in a fantastic Red Bank location.