Before You Bid on a Chilmark Property, Ask Who Owns the Road

Who owns the road to this house? Most buyers on Martha's Vineyard never think to ask. It is exactly the question that stalls Chilmark closings weeks after the inspection is done, the financing is arranged, and the buyer believes the hard part is behind them.

In most Massachusetts towns the answer barely matters. A town plows the road, patches the frost heaves, and eventually approves repairs at a town meeting. In Chilmark, the answer decides whether a mortgage funds on schedule, whether a special assessment shows up in year two of ownership, and whether the neighbor down the lane becomes a legal counterparty for the next several decades.

The Math Behind Chilmark's Quiet Roads

State transportation records sort every mile of Massachusetts roadway into two categories: accepted, meaning a town or the state has formally taken responsibility for it, or unaccepted, meaning it has not. In Chilmark, the Massachusetts Department of Transportation's road inventory shows roughly 14 of the town's 22 total road miles fall into the unaccepted column, well over half. Only about 7.8 miles are town-accepted. Road acceptance votes happen rarely on the Vineyard, and this ratio has held steady for years, because accepting a road obligates the town to build it to a construction standard and maintain it in perpetuity, a cost most up-island towns are in no hurry to assume for a handful of houses at the end of a stone-wall lane.

That ratio is not a footnote. It means the odds that a given Chilmark driveway or lane sits on an unaccepted way are better than even. The rolling hills, working farms, and private beach lanes that define the town often exist in their current form precisely because the roads serving them were never built, or accepted, to the standard a public way requires.

Why Your Lender Cares Even If You Don't

Massachusetts has no default law forcing neighbors to split the cost of repairing a private road. The Massachusetts Municipal Association's own guidance is direct on this point: private ways sit entirely outside municipal responsibility, and while a town can vote to plow snow on some of them, it is barred from spending public money on major repairs to private land. Absent a recorded agreement, there is no statute that obligates the owner up the hill to pay a share when the culvert washes out.

That gap is exactly what a Private Road Maintenance Agreement, or PRMA, is built to close, and it is exactly what a mortgage lender wants to see recorded before funding a loan. Different lenders draw the line differently, as GoldCoast Mortgage explains:

The gap between those requirements is where deals lose weeks, not days. A buyer whose loan is headed to Fannie Mae can discover at underwriting that the property's road has never had a formal agreement. Someone then has to draft one, circulate it to every owner on the lane, and get every signature before the lender will fund. If even one neighbor is unreachable or unwilling, the financing can stall for reasons that have nothing to do with the buyer's credit or the house itself.

For a seller, the fix is straightforward once you know to look for it: confirm whether a PRMA already exists and is recorded at the Dukes County Registry of Deeds before the property goes on the market, not after an offer arrives.

The Same Pattern, Different Wire

Chilmark's roads are not the only piece of "public" infrastructure that turns out to be private. Overhead electric lines follow the same logic. Eversource does not always own the poles and wire running to a house at the end of a private lane, and when that infrastructure fails, homeowners have learned the company will not pay to fix what it does not own, even though a maintenance fee appears on every monthly bill regardless of who owns the line.

The Martha's Vineyard Times documented the scale of this in 2018, reporting that on Tiasquam Road and Looks Pond Way, residents were told nine utility poles needed replacing at a cost of $109,000. On Chappaquiddick, fifteen neighbors split a $200,000 bill to replace a roughly 45-year-old private line, and none of them had known the line was private until it began failing. Basic repairs to underground private lines alone can run $3,000 to $4,000, according to the same reporting. Residents on some of these private systems have since formed powerline associations, nonprofit entities built for one purpose: spreading the legal and financial liability of keeping the lights on among people who did not choose their neighbors as business partners.

A quiet lane with buried utilities photographs beautifully. Whether that lane's power line is a private financial obligation shared with strangers is a question worth asking before it arrives as an invoice.

When the Association Outlasts the Law

Private roads and private lines are agreements between neighbors. A homeowners association is something else: a standing entity with bylaws that can restrict what an owner is allowed to build, sometimes for decades, sometimes past changes in state law itself.

Quansoo, a 71-acre Chilmark subdivision the Martha's Vineyard Commission approved for sixteen building lots back in 1986, is a live example. That approval came with a condition: the homeowners association would prohibit construction of additional dwellings on any lot. In 2024, the state's Affordable Homes Act gave homeowners across Massachusetts the right to build accessory dwelling units regardless of local zoning. Quansoo's HOA rule was never local zoning, it was a private covenant. As the Vineyard Gazette reported in December 2025, the Martha's Vineyard Commission was still reviewing an ADU application from a Quansoo property owner testing exactly that distinction, because a private association's bylaws are not bound by a law written for municipal zoning codes.

The lesson is not particular to Quansoo. It is that an HOA's governing documents deserve the same scrutiny as the title itself, because those documents can outlast a change in state law that would otherwise apply to nearly every other property in Massachusetts.

What This Means Before You Write an Offer

None of this should discourage anyone from Chilmark's stone walls, working farms, or private beach keys. It should change what gets asked, and when.

• Ask whether the access road is town-accepted or unaccepted, and if unaccepted, whether a PRMA is already recorded at the Dukes County Registry of Deeds.
• Ask your lender directly whether their investor, Fannie Mae, Freddie Mac, or a VA program, requires a signed PRMA or will accept a recorded easement instead.
• Ask whether the property's electric service runs on a private line, and if so, whether a powerline association or cost-sharing agreement already exists.
• If the property sits within a homeowners association, read the governing documents before the offer goes in, particularly any restriction on additional structures or dwellings.

These are the questions that separate a straightforward closing from a financing scramble that surfaces in week five, after everyone thought the hard part was over.

Frequently Asked Questions

Does every Chilmark property have a private road or line? No. Plenty of Chilmark properties sit on town-accepted roads with standard utility service. The point is that the odds are meaningfully higher here than in a typical Massachusetts town, given how much of the town's total road mileage remains unaccepted, so it is worth confirming rather than assuming.

Can I still get a mortgage without a PRMA? It depends on your lender and which investor buys the loan. Freddie Mac and VA loans generally accept a recorded easement without a separate maintenance agreement, while a loan headed to Fannie Mae typically requires a signed PRMA unless state law already assigns responsibility. Ask early which investor your lender sells to.

How do I find out if a road is private before making an offer? A real estate attorney or title company can confirm a road's status and search the Dukes County Registry of Deeds for a recorded PRMA as part of due diligence, ideally before an offer goes in rather than during the financing contingency period.

Chilmark's privacy is the reason people fall in love with it, and it is also the reason the fine print matters more here than almost anywhere else on the island. The Agency Martha's Vineyard has spent years walking clients through exactly these questions, road status, recorded agreements, association bylaws, before an offer goes in, not after. Request a Local Consultation to talk through what a specific Chilmark property actually involves.