There is an Ontario model for this, albeit a small one. Circa 1995 aboriginals blocked a road that ran through a First Nations community, into a small Georgian Bay village of Skerryvore north of Parry Sound. After much lobbying, the province ended up paying half of the costs of building a new road on crown land that bypassed the First Nations reserve. The costs to the residents for the road was then turned into a 20 year debenture and the local municipality levied an annual additional "road tax" onto each of the property owners in Skerryvore until the debenture is paid off.
In late spring of 1997, the new road opened and was named The Skerryvore Community Road. It has the distinction of being the one and only public road in Ontario if not in Canada partly paid for by the private property owners of the area. 2007 saw the first 10 years of the 10 & 10 road debenture paid off with some residents opting to buy down their share of the balance and others opting for another 10 years of road tax.