Rarely does a Woodstock home come along with this much soul, flexibility, and built-in opportunity. Tucked away on just over an acre off private Chipmunk Lane, this charming 2265 sq ft Cape Cod cottage style home captures the feeling people come to Woodstock hoping to find: a little privacy, a little magic, a little room to create, and a home that feels deeply personal from the moment you arrive. At the heart of the main house is a wonderfully memorable kitchen, full of color, character, and warmth. This is not a showroom kitchen trying too hard. It is the kind of kitchen where meals stretch into stories, friends gather around the island, coffee starts slowly, and the house begins to feel like home. The adjoining living areas continue that same spirit, offering inviting spaces for conversation, quiet mornings, winter nights in front of the wood stove, and the everyday rhythm of country life. The main home offers two bedrooms and two full baths, along with a highly useful first-floor office/flex room off the living room that can easily function as a guest room, studio, work-from-home space, or possible first-floor sleeping area. Upstairs, vaulted ceilings and exposed beams bring classic Cape Cod charm to a second living area that could become a media room, playroom, creative workspace, or future bedroom or bath, depending on your needs. What makes this property especially rare is the legal, fully licensed short-term rental component. Connected through the center mudroom yet able to live entirely separately, the one-bedroom guest suite creates meaningful income potential without compromising the privacy or normal function of the main home. With its own entrance, separate driveway, private parking, and established Airbnb history, it feels less like an afterthought and more like a thoughtful second world on the property. For artists, makers, musicians, remote workers, weekenders, or anyone looking for a Woodstock home that can support both lifestyle and income, the versatility here is exceptional. Live in the main house and rent the guest suite. Keep the suite for visiting friends and family. Use it as a detached-feeling studio, wellness space, or creative retreat. The layout gives you options now and flexibility for whatever comes next. The setting is equally compelling. Over an acre gives the property breathing room, with mature trees, garden moments, and a tucked-away feeling that still keeps you close to the village proper of Woodstock. Historic Kingston, Saugerties, hiking, restaurants, music, shops, and farm-to-table favorites are all within easy reach, and the Kingston Thruway exit is less than 10 minutes away for a more convenient connection back to New York City. This is the rare Woodstock combination buyers keep hoping to find but almost never do: character, privacy, legal short-term rental income, separate living spaces, creative flexibility, and a location that feels both hidden away and connected to everything. A cottage home with charm, a property with purpose, and a lifestyle that is ready to begin on day one.