Virginia, you must start with the basics - your organization's bylaws. Do you have a copy?  The bylaws should reveal what is included in the term "maintenance", how the maintenance budget is established, how cost assessments are apportioned to each lot and how it is approved by the members. They may also (actually should also) reveal the method of enforcement of the collection of the maintenance assessments, establish some form of leadership for the group and when meetings are held.  

Having said that, your situation is not unusual, especially for such a small number of lots on the private road and you may find that there are no bylaws or any form of formal road association.   Once you have the bylaws, or determined that they do not exist, get back to us.   In the meantime, you should know that there is a state law that requires owners on private roads to contribute equally to road maintenance (and snow removal is part of maintenance) but it only applies when there is no agreement in place - see it on the Resources page TITLE 23, §3121.pdf 

Thank you so much for your response. We do have the copy of the Deed/Maintenance Declaration for the road. There was none one whose name was documented as being “appointed” to a position of authority, but, with that being said, all we received from a neighbor was a letter stating what we owed for the snow plowing, and, who was contracted to do the work. The letter came stuck between outer screen and front door. Not knowing how this was done, but knowing there was an HOA for plowing only, we thought this was how it was done. The neighbor who had been doing this previously, never introduced himself and basically kept doing what was previously established with the former neighbor. We have sent letters explaining why the formula for establishing a contract with a contractor was not working. We scrambled the third year to get a plow contractor, after the first storm, and most didn’t have the capacity/time to add another job. The contractor we hired has been very sensitive to the situation and actually dropped his price, which isnt fair to him and the neighbor gets clear use of the road. In our last letter we recommended that if they didn’t agree with the “majority vote”, they were welcome to file for arbitration with the State of Maine. Not sure what else to do except to place a lien on the property, but that would be a last resort. As far as I know from the other neighbors who agree with the current contract, there have been no meetings that have taken place. 
Again, thank you for responding

Best Virginia

Good news Virginia, the solution to your problems is at your fingertips. You mentioned that there is a recorded maintenance agreement.   That was easy for me to find.  Luckily, your deed mentions the agreement and it applies to all 4 lots on your road. The deed, too, was easy to find.  I have sent a copy to you via the private email mentioned in your member profile just to be sure you have the recorded documents.

Your property was formed by subdivision approved by the town and all lots are "....subject to the terms and conditions of the Road Maintenance Declaration....."  The Road Maintenance Declaration is an agreement "...binding on the owners of lots 1through 4....." the owners ..."jointly and severally agree to be obligated to maintain, repair, plow, sand and replace the road so that it is reasonably safe and maintained in a good and passible condition...."  

The Declaration states that "....all decisions......shall be determined by a majority vote of the Voting Owners", it permits the owners to appoint one owner as a manager who can act on behalf of the other owners. It defines the cost apportionment for each owner as 1/4 of the cost of maintenance and provides for binding arbitration in the event of a disagreement with the cost of arbitration split 50% to those owners filing for arbitration and 50% to the owner (or owners) against whom the arbitration is being filed. 

The Declaration is quite specific, easily to understand, carry out and enforce.  I suggest you call a meeting of the owners, have a clear agenda that spells out the process of awarding contracts, establishes a maintenance budget for the year, appoint a manager, then vote on the matters in the agenda.  

The Declaration does not say how votes are take, when meetings, if any, are held or how to legally notify the lot owners. I suggest you follow the provisions of Maine's Private Way Act that requires an owner list be obtained from the municipal tax assessor and that meeting notices, at least for the first meeting, be sent by first class mail to the address on the assessor's list.  Take Roberta's advice and read through the material available on the Resources tab.

I suspect that if handled properly the dissenting owner will fall in line and pay what is due, especially when the dissenting owner realizes that the owner will pay 50% of the cost to arbitrate the maintenance costs that the owner is clearly legally obligated to pay and will be responsible for 100% of the cost to collect, including legal fees, if the owner continues to fail to pay.

By the way, you and your neighbors will have to initiate the arbitration, not the nonpaying owner.  But if you do it as a group the three of you will pay 50% of the cost and the nonpaying owner will pay the other 50% according to the Declaration.

So many lot owners along private roads in Maine do not have all that is available to you by deed restrictions. Take advantage of your good fortune.

I believe if you formed a Statutory Road Association the owner of the fourth lot would be obligated o pay their fair share. In our Statutory Association By-laws, we stipulate a 1/2 share for an owner of a parcel with three undeveloped lots as follows:

"Parcels without a dwelling unit will be responsible for one-half (1/2) share of maintenance fees until the next Annual Meeting after the completion of a dwelling unit." 

Yes, you are correct Virginia.  The Road Maintenance Declaration says that maintenance responsibility applies only to lots that have been improved.  So, it appears that you cannot bill the owner of the unimproved lot, no matter who it is, until a residence is built upon it.  However, the Declaration pretty well spells out what is necessary to move forward, and it has the authority of a deed restriction.  Compared to others living on private roads in Maine, you are fortunate.  

While I cannot give you legal advice, I strongly recommend you start to establish methods and procedures to take advantage of the protections the Declaration provides you.  Road maintenance expenses are inevitable and not necessarily limited to snow clearing. Gravel roads often need maintenance because of snow clearing.

No matter how busy or disinterested in the topic, someone among the three improved lots has to act and the sooner you establish procedures to carry out the obligations under the Road Maintenance Declaration the better it will be for all.  

Regardless of the personal circumstances of a dissenting owner, the Declaration makes it a clear obligation of each owner to pay a share and it actually says that unpaid expenses are a lien on the non-payor’s property.  So that gives you the authority (after proper notice) to place a lien. A lien is proof of a debt, but you are not protected until that lien is actually filed and recorded in the county.  Once a lien is placed, if the property is sold it is very likely that the debt will be repaid.  Look over the Resources page for examples of late notes and notices of a lien.  None will fit your situation exactly but most are in Word format so you can easily make changes to fit.

Carrots are often better than sticks. You can learn about mediation here https://mainemediators.org but do not neglect to set up procedures operate your private road!