Second Home Exit Strategies

Second Home Exit Strategies: Planning Your Next Chapter

If you own a second home or rental property in Vail, Breckenridge, or elsewhere in the High Country, now is the time to take a proactive look at your long-term plan.

Markets shift. Tax laws evolve. Personal priorities change. The most successful property owners aren't reacting in the moment. They're planning ahead.

This class is designed for second homeowners and rental property owners who want to take control of their next move before they are forced into one.

Whether your property is a personal getaway, a short term or long term rental, or part of a larger real estate portfolio, having a clear exit or transition strategy is key. It can help you unlock equity, reduce ongoing management, protect assets from unnecessary taxes, and free up time for what matters most.

In this educational workshop, you will learn:

• How to evaluate when it makes sense to exit, hold, or reposition a second home
• How to use exit strategies as part of retirement and lifestyle planning
• Diversification approaches for real estate holdings that preserve income while reducing hands-on involvement
• Key tax considerations every second homeowner should know before selling or transitioning property
• Market timing strategies tailored to ski resort and mountain communities

This class is ideal for property owners who are asking bigger questions about their real estate:

• Is this property still aligned with my goals?
• Am I managing real estate, or is real estate managing me?
• What would my ideal next chapter look like?

If you want clarity, options, and a plan rather than guesswork, this class is for you.

Seats are limited. Join us for a practical discussion on second-home exit strategies and a live Q&A with Anne Skinner.

Presented by Anne Skinner, lead agent of The Skinner Team with over a decade of experience guiding second-home and investment property owners plan strategic real estate decisions.