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 60 Owl Pine Lane, Highlands, NC 28741 (MLS # 87161)
    20
    3 beds,  2 baths
    lot 21,780 sqft
    MLS 87161
  2. 0 beds,  0 baths
    lot 21,344 sqft
    MLS 87003
  3. 0 beds,  0 baths
    lot 13,503 sqft
    MLS 87002
  4. 0 beds,  0 baths
    lot 13,503 sqft
    MLS 87001
  5. Photo of 10 Hardscrabble Ridge Road, Highlands, NC 28741 (MLS # 87000)
    2
    0 beds,  0 baths
    lot 2.40 ac
    MLS 87000
  6. Photo of 7 Hardscrabble Ridge Road, Highlands, NC 28741 (MLS # 86999)
    2
    0 beds,  0 baths
    lot 3.64 ac
    MLS 86999
  7. Photo of B Tanner Loop, Highlands, NC 28741 (MLS # 86987)
    2
    0 beds,  0 baths
    lot 13,503 sqft
    MLS 86987
  8. Photo of # 4 Hardscrabble Ridge Road, Highlands, NC 28741 (MLS # 86986)
    3
    0 beds,  0 baths
    lot 1.61 ac
    MLS 86986
  9. Photo of 3 Hardscrabble Ridge Road, Highlands, NC 28741 (MLS # 86985)
    4
    0 beds,  0 baths
    lot 2.07 ac
    MLS 86985
  10. Photo of # 2 Hardscrabble Ridge Road, Highlands, NC 28741 (MLS # 86984)
    3
    0 beds,  0 baths
    lot 2.95 ac
    MLS 86984
  11. Photo of 803 Highlands Mountain Club Drive #803, Highlands, NC 28741 (MLS # 86856)
    19
    2 beds,  2 baths
    MLS 86856
  12. Photo of 289 Apple Mountain Circle, Highlands, NC 28741 (MLS # 86359)
    23
    3 beds,  4 baths
    lot 43,560 sqft
    MLS 86359
  13. Photo of 750 Bee Branch Road, Bryson City, NC 28713 (MLS # 83377)
    11
    lot 16.25 ac
    MLS 83377
  14. Photo of Hwy. 106 Happy Hill Road, Scaly Mountain, NC 28775 (MLS # 81016)
    5
    0 beds,  0 baths
    MLS 81016
  15. 0 beds,  0 baths
    lot 50.45 ac
    MLS 81014
  16. Photo of Lot  2 Fallen Leaf Lane, Highlands, NC 28714 (MLS # 79146)
    3
    0 beds,  0 baths
    MLS 79146
  17. 0 beds,  0 baths
    lot 26,136 sqft
    MLS 61194
  18. 0 beds,  0 baths
    lot 1.29 ac
    MLS 63086
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