Two seasons, one house that never misses

Aspen runs on two seasons. Winter from mid-December through the end of the ski year, when the house on Red Mountain fills with family and guests and the kitchen never quite closes. Then summer — June through Labor Day — which many families now consider the better season: the Music Festival, Ideas, hiking out the back door. Between them sit the shoulder months, when the town exhales and the house waits.

That rhythm makes the year-round caretaker the most important hire in the valley. Someone local who watches the property through mud season, manages snow removal and the contractors you can never quite schedule, and has the house warm, plowed, and provisioned before your plane lands. Domestic couples do this work beautifully here, and the good ones are known up and down the valley.

The hard truth of Aspen staffing is housing. Local candidates are scarce and expensive to house; a property with staff quarters or an ADU can hire from anywhere. Altitude, mountain driving, and the seasonal surge of guests round out what we screen for — this is not a market where a city résumé transfers automatically.