More Ways to Live. More Ways to Own. 139 Forest Trail presents one of Winter Park’s most distinctive ownership opportunities. Ideally located within walking distance of downtown Winter Park, this thoughtfully renovated property offers the rare advantage of two fully independent residences under one ownership-creating exceptional flexibility for a private mountain retreat, second home with proven rental history, multi-generational living, shared ownership, or the opportunity to generate meaningful supplemental income while preserving the lifestyle that makes mountain ownership so rewarding. The upper residence serves as the primary living space, featuring three bedrooms, two bathrooms, an open-concept kitchen with quartz countertops and a large center island, an expansive great room with a gas fireplace, an oversized primary suite, and a private deck with mountain views. Warm wood flooring and accents, contemporary mountain finishes, radiant heat, a tankless water heater, new roof, boiler and windows, and abundant natural light create an atmosphere that is both sophisticated and inviting. The fully updated lower residence offers three bedrooms, three bathrooms, a spacious living area with a wood-burning fireplace, a full kitchen, private laundry, and a flexible bonus room ideal for a home office, fitness space, or additional guest accommodations. Designed for comfort and privacy, it functions beautifully for extended family, visitors, shared ownership, or private rental use. Located directly across from the Lift bus stop and just moments from world-class skiing, hiking, biking, restaurants, shopping, and year-round recreation, the property also includes a 0.03-acre adjacent parcel, adding value and future possibilities. Where mountain living, thoughtful design, and remarkable versatility come together-creating an ownership opportunity unlike any other in Winter Park.