139 Forest Trail
More Ways to Live. More Ways to Own. 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, a second home with proven rental history, multi-generational living, shared ownership, or the opportunity to offset ownership costs while enjoying everything Winter Park has to offer. The upper residence serves as the primary living space, featuring three bedrooms, two bathrooms, an open-concept kitchen with custom cabinets built from old growth redwood from a 100+year old barn, quartz countertops and a large center island, an expansive great room with a gas fireplace, an oversized primary suite, and a private deck showcasing mountain views. Warm wood flooring and accents, contemporary mountain finishes, radiant heat, 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 anchored by 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 to provide comfort and privacy, it functions beautifully for extended family, visitors, shared ownership, or private rental use. A proven rental history provides the opportunity to generate meaningful supplemental income while preserving the lifestyle that makes mountain ownership so rewarding. Thoughtful updates throughout create a turnkey home ready to enjoy from day one. 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 an additional 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.
Getting a property under contract is about a quarter of the work.
The other seventy-five percent -- inspection and objection, negotiation, title, due diligence and HOA nuance -- happens after. That is where a transaction succeeds or falls apart, and it is exactly where a solo agent runs out of hours. Roughly twenty agents do more than eighty percent of the business in this market, out of four to five hundred who transact here each year. We are one of them, and we are a team of ten rather than one person with a phone.
Two owners, four Mountain Property Specialists, dedicated transaction management and finance. $835 million closed and 852 transactions over the past decade, all of it in Grand County.
School assignments come from the MLS listing and can change. Confirm with the district before you rely on them.
Tell us when works and the team will confirm the showing with the listing brokerage.
Listing data is provided by the Grand County Association of REALTORS® MLS (GCARMLS).
Information in this listing has not been verified by the Grand County Association of REALTORS® MLS (GCARMLS) and should be independently verified by consumers. Information is deemed reliable but not guaranteed and is subject to change without notice. This data is provided for consumers’ personal, non-commercial use only to identify potential properties for purchase. Unauthorized reproduction or redistribution of this information is prohibited. Listing data and the compilation thereof are protected by copyright and other applicable law.
Listing data last updated 9/8/2026, 6:00 PM MDT.
