Historic Lakefront Compound on .66 Acres in the Hourglass District. Rare opportunity to acquire two adjoining properties totaling approximately .66 acres on scenic Lake Hourglass in Orlando's highly desirable Hourglass District. Combining Old Florida charm, income-producing potential, and future flexibility, this unique R-2-zoned offering presents a truly exceptional ownership opportunity. The centerpiece is a beautifully preserved Florida Vernacular cottage (2/1) dating back 100 years, featuring original heart-of-pine flooring throughout the living areas and bedrooms, original glass windows, a wood-burning fireplace, and a charming screened porch that captures the timeless character of early Florida living. Surrounded by thoughtfully designed Florida-native landscaping, the home enjoys a peaceful and private setting rarely found so close to Downtown Orlando. The adjoining property at 1802 Chamberlin Street (2/2) includes a charming, renovated income-producing residence updated in 2019 and currently generating approximately $34,000 in annual gross rental income. Highlights include vaulted ceilings, Mexican Saltillo tile in the lakeside unit, generous outdoor living spaces, and a large covered deck overlooking the beautifully landscaped grounds. Additional features include irrigation throughout both properties, full perimeter fencing, mature landscaping, lake frontage, and R-2 zoning providing exceptional flexibility for a variety of future uses. Whether envisioned as a private family compound, multigenerational retreat, income-producing investment, or long-term legacy property, the possibilities are extraordinary. Lake Hourglass is a peaceful, non-motorized lake, offering a serene natural setting free from powerboat traffic while providing beautiful water views and abundant wildlife. The property's exceptional privacy and mature landscaping create a tranquil retreat in the heart of the city. Ideally located within the highly regarded Lake Como K-8 and Boone High School districts, this one-of-a-kind property also offers convenient access to Downtown Orlando, Orlando Health, Orlando International Airport, and the dining, shopping, entertainment, and cultural amenities that make this one of Orlando's most sought-after neighborhoods. A truly rare opportunity to own a historic lakefront compound offering character, income potential, privacy, and future possibilities in the heart of Orlando.