This extraordinary 1937 Colonial is a rare opportunity to own a truly one-of-a-kind property where timeless craftsmanship, historic character, and modern versatility come together seamlessly. Overlooking picturesque golf course views, the main residence features 4 bedrooms, 2.5 bathrooms, original hardwood floors, custom-crafted woodwork and finishing, historic picture rail molding and multiple wood-burning fireplaces that showcase the home's classic charm. The updated kitchen blends style and function with marble countertops, stainless steel appliances, soft-close cabinetry, and recessed lighting. Upstairs, the spacious primary suite includes a private en suite bath and fireplace, while two additional bedrooms share a traditional Jack-and-Jill bathroom. Outside, a majestic mature Live Oak anchors the expansive backyard, complemented by a circular driveway, patio pavers, storage shed, and oversized side driveway with room for a boat or RV. Adding exceptional value is the highly sought-after detached guest residence featuring a spacious living area, large bedroom with walk-in closet, full bathroom, and kitchenette. Ideal for multigenerational living, guest accommodations, a private office, long-term rental income, or short-term rental potential, this flexible space offers multiple exit strategies rarely found in today's market. Blending architectural elegance with modern updates and income-producing potential, this remarkable Colonial stands in a class of its own. See attachments and/or reach out to listing agent for additional details and numbers regarding all possible income producing avenues.