The Homestead was opened in 1940, using a lodge referred to by that name on the grounds of the private Leelenau Schools. It is in the Sleeping Bear Dunes area, one of the most beautiful, scenic places in the US.
In 1963, The Leelanau School was reorganized from a privately owned school to a non-profit corporation and a portion of the original school property, including the Homestead Lodge, was transferred to the resort which was modernized and expanded at this time.
I do not know when skiing began on the property or when lifts were first installed. Winter activities were encouraged at the school, so likely the students and faculty were touring the dunes on skis and snowshoes long before 1940. The school was an early supporter of competitive alpine skiing and appears to have been, along with the public school in Traverse City, instrumental in the development of nearby Sugarloaf as a ski area.
The Homestead now offers skiing an snowboarding on their dune with 2 triple and one double chairlifts and one rope tow as well as x-c skiing, snowshoeing and ice skating.
If you have any information about the development of skiing at The Homestead, please post your comments here or send them to us via the directions on the About MILSAP page.
MILSAP 
Skilifts.org says 1984 the 3 Borvig lifts were installed. I skied here 2/24/13 and all 3 lifts were Leitner. Great little intimate area for families with fantastic Lk Mich and Glen Lk views! Right on top of par 3 nine hole golf course.
Those runs were serviced by a rope tows well before and during my two years at Leelanau School in 1970 and 1971. They had a jump run you could take and fly over 50 feet distance a safe foot or two off the slope. Pepe Teichner was a early Michigan skiing pioneer that instructed students back when the school was founded. We mostly skied at Sugarloaf ski area with a quick 10 minute bus ride to the slopes, sometimes 5 days a week. It is located just off the waterfront on the shore of Lake Michigan. If you could dress and stay warm there with the winter on the water humidity, you were set for skiing anywhere in the US. The Homestead is a beautiful family oriented ski resort now.