Jack Callaway

Jack Calloway served as CEO of the Highlands-Cashiers Hospital and Foundation for many years and was integrally involved in relocating the Hospital from the Peggy Crosby site to the present location. Since his retirement from the Hospital in 2006, Jack has been active in the real estate market as a Buyer, Seller, and Broker. He held a North Carolina Commercial Contractors license for a number of years, allowing him a unique insight into the overall area real estate market. Jack is originally from Highlands and has seen exciting and beneficial changes on the Highlands Plateau. The village has emerged from a sleepy settlement where the "season" lasted twelve weeks to a vibrant year round community treasured by all those who call Highlands home, whether seasonally or year round. Jack has successfully assisted clients with the purchase and sale of multimillion dollar properties as well as small mountain cabins and home sites. Jack is excited to be a part of the Sotheby's team which provides unparalleled expertise and service to their clients. He would welcome the opportunity to assist you with any of your real estate needs.

The Highlands-Cashiers area offers a wide range of activities year round to enable the most energetic residents to stay as busy as they prefer. For small communities there is something continuously "going on" in which to participate or attend. And when there is a rainy or snow day, it provides a welcome opportunity catch up on some of that reading that may have been neglected. That's why we lovingly refer to the mountain area as our on little 'bit of heaven."


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  1. Photo of Highlands, NC 28741 (MLS # 86359)
    23
    3 beds,  4 baths
    lot 43,560 sqft
    MLS 86359
  2. Photo of Sapphire, NC 28774 (MLS # 84784)
    24
    5 beds,  5 baths
    lot 27,007 sqft
    MLS 84784
  3. Photo of Bryson City, NC 28713 (MLS # 83377)
    11
    lot 16.25 ac
    MLS 83377
  4. 0 beds,  0 baths
    lot 2.19 ac
    MLS 83000
  5. Photo of Scaly Mountain, NC 28775 (MLS # 81016)
    5
    0 beds,  0 baths
    MLS 81016
  6. 0 beds,  0 baths
    lot 50.45 ac
    MLS 81014
  7. Photo of HIGHLANDS, NC 28714 (MLS # 79146)
    3
    0 beds,  0 baths
    MLS 79146
  8. 0 beds,  0 baths
    lot 26,136 sqft
    MLS 61194
  9. 0 beds,  0 baths
    lot 1.29 ac
    MLS 63086
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Listing information is deemed reliable, but not guaranteed.

This MLS IDX is (c) Diverse Solutions 2017.