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Jack Bailey

Jack Bailey

| Seasonal Rentals

Jack specializes in finding winter seasonal rental homes for WRG customers. Jack’s familiarity with the resort area, proximity to skiing and outdoor activity makes him an invaluable contact for a winter seasonal renter. His work ethic, management skills, contagious kindness, and enthusiasm truly make him an asset to our team at Wohler Realty [...]

Jack specializes in finding winter seasonal rental homes for WRG customers. Jack’s familiarity with the resort area, proximity to skiing and outdoor activity makes him an invaluable contact for a winter seasonal renter. His work ethic, management skills, contagious kindness, and enthusiasm truly make him an asset to our team at Wohler Realty Group. 

For the past 28 years, Jack has worked as a professional alpine ski racing coach, training athletes for national and international competition. Jack’s reputation and honest character are well-regarded in the professional racing community. Based at Stratton Mountain School and Killington Mountain School, Jack’s experience in the racing industry has cultivated a broad range of skills. He applies knowledge and attention to detail to everything he does. He understands the needs of outdoor-oriented families. 

Jack is the founder and director of Vermont Rare, a local nonprofit that raises awareness and donations for patients and families living with rare diseases. Jack organizes and hosts their annual gravel bike race to raise funds for the foundation. 

Jack has a degree in business from the University of Maine at Farmington. Growing up, he learned the importance of hard work and meeting the needs of clients working as an apprentice to his father in their family plumbing business in New Jersey.

Jack and his wife Marybeth have lived in Vermont since 2000. Since raising their two sons Finegan and Shane and their dog Annie, they could not imagine having it any other way. For a whole family of outdoor enthusiasts, there is no better place than Vermont! 

When Jack is not traveling the world coaching athletes or organizing bike race benefits, you can find him biking the many dirt roads and trails around Peru, Landgrove, Weston, Londonderry, and Stratton. As a serious bike racing competitor, outdoor recreation is a way of life for Jack. To him, nothing is better than discovering a quiet swimming hole or enjoying the sunrise with the perfect cup of joe.

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