Set along one of Woodland Heights’ most picturesque tree-lined corridors, this 1923 American Foursquare pairs timeless architectural character with bespoke artisan craft and rare modern versatility. Perfectly situated an easy stroll from Forest Hill Park, the James River Park System, local cafes, and minutes to Downtown Richmond, this home delivers the ultimate Southside lifestyle. Curb appeal begins with an arched front porch with swing framed by cobblestone-lined landscaping. Inside the 2,044 sq ft main home, 9+ ft ceilings, heart pine floors, and bespoke custom window ironwork by Phoenix Handcraft elevate the historic charm. You’re greeted at the door with newly refinished original hardwood floors, the living room features a restored gas fireplace, leading into a bright kitchen equipped with granite counters, sunny windows, breakfast bar open to dining, and a Bosch dishwasher (2024). French doors open to a screened porch stepping down to a stamped concrete patio, raised garden beds, and a fully fenced, beautifully landscaped yard. Upstairs, the primary suite features a private enclosed sleeping porch, joined by two guest bedrooms, a second full bath, and a finished third-floor dormer loft. Major systems offer turnkey peace of mind: roof (2022), upstairs HVAC (2022), water heater (2022), inspected chimney (2024), and a waterproofed basement for storage. Out back sits a premier modern asset: a new detached, conditioned, 2-car garage with epoxy floors and ground-floor half bath, crowned by 480 sq ft of fully heated and cooled second-floor living space. Bringing total usable conditioned area to over 2,520 sq ft, this private loft is ideal as an executive office, creative studio, or potentially a detached ADU/guest suite.