Shot-putter Valerie Adams, BMX cyclist Sarah Walker, single sculls rower Mahe Drysdale and boardsailor Jon Paul Tobin were among Mr Jackson's top picks for the podium.
Bayleys agent Leeon Johnston said it was the first time he had heard of a Olympic medal haul donation being offered as a sales incentive.
Mr Jackson and his wife Lesley started the Motueka business six years ago. It produces sauvignon blanc, riesling and pinot gris using only grapes grown onsite.
Since then the label has won 34 medals nationally and internationally and the riesling last year won gold at the Air New Zealand Wine Awards.
Mr Jackson said he was looking for new challenges.
Located 7km from Motueka, the property includes the Jackson family home overlooking the 6.7 ha vineyard planted of approximately 10,000 vines, as well as olive and hazelnut plantations.
The eco-designed home includes commercial space for cellar door tastings and wine sales.