Scroll through Oak Bluffs listings long enough and the pattern becomes obvious. Somewhere in the mix, tucked among East Chop shingle-style homes and harbor-view properties pushing well past a million dollars, sit a cluster of small, brightly painted cottages that consistently list for less. They are the most photographed buildings in town. They are also, by most measures, the cheapest.
The instinct is to chalk this up to square footage. These cottages are small, some barely a few hundred square feet on the ground floor, stacked with narrow staircases and low ceilings. Size explains part of the gap. It does not explain all of it.
The real answer sits in the deed, or rather, in what the deed does not include. Buy one of these cottages and you own the structure. You do not own the land beneath it.
The building is yours. The ground isn't.
The cottages in question sit inside what everyone on the island calls the Camp Ground, a National Historic Landmark district managed by the Martha's Vineyard Camp Meeting Association. The association traces back to 1835, when Jeremiah Pease and six other members of the Edgartown Methodist Church secured a half acre of land in Oak Bluffs for summer religious gatherings. Tents gave way to tent platforms, then to wooden cottages built to mimic the shape of the tents they replaced. By the late 1800s there were hundreds of them clustered around a central meeting space. In 2005 the Camp Ground itself was placed on the National Register of Historic Places, a designation that recognizes the district's architectural and historical significance.
The association still exists today, and it still functions the way it did a century and a half ago: as the landowner. According to its own website, the Martha's Vineyard Camp Meeting Association is a religious, nonprofit organization that continues to hold title to the ground beneath every cottage in the district. What a buyer purchases is the structure and a lease on the lot it sits on, not fee simple ownership of real property in the conventional sense.
This is not a technicality that shows up in fine print after closing. It is the entire reason these cottages carry a different price ceiling than everything else in Oak Bluffs, and it changes how the purchase actually works.
Why your bank may say no
A buyer accustomed to a standard 30-year mortgage will run into friction quickly. Most conventional lenders underwrite against the land as collateral. If there is no land to pledge, many will not write the loan at all. A 2012 profile of the Camp Ground in Martha's Vineyard Magazine described this exact problem, noting that most banks will not issue mortgages for a house without land ownership, and that buyers instead turn to Vineyard-based banks that understand the association's lease structure and are willing to work within it.
That structural reality has not changed. The association's own site still refers to purchasers as leaseholders rather than property owners, which is the clearest signal that the underlying arrangement, and the financing complications that come with it, remain in force. A buyer comparing a Camp Ground cottage to a conventional Oak Bluffs single-family home is not just comparing square footage and finishes. They are comparing two different financing paths, one of which likely starts with a phone call to a local bank rather than a national lender's online portal.
Buying in means joining, not just closing
There is a second layer to this that a listing sheet will never surface: becoming a Camp Ground owner has historically meant becoming part of the association itself, not simply completing a transaction.
The 2012 magazine profile described a vetting process for prospective leaseholders that included letters of recommendation, with the association's religious character built into the requirements. Whether every detail of that process still applies today is worth confirming directly with the association before writing an offer, since these things can shift over time. What has not shifted is the underlying fact: the Camp Meeting Association is not a passive landlord collecting ground rent. It is an active religious nonprofit that treats cottage ownership as a form of membership, and its own materials on buying a cottage frame the process in exactly those terms.
That membership comes with day-to-day rules too. The association's cottage rental guidance caps how the property can be used for short-term rental income and does not allow pets for renters, restrictions that would strike a typical Oak Bluffs vacation rental owner as unusually specific. For a buyer weighing a Camp Ground cottage against a similarly priced condo near the harbor, this matters as much as the purchase price.
What the discount actually reflects
None of this makes the cottages a bad investment. It makes them a different kind of investment, one where the numbers only make sense once you understand what's underneath them.
Oak Bluffs as a whole has held up well. Trailing twelve month sale data from spring 2026 puts the town's median sale price at roughly $1.23 million, up about 5 percent year over year, with active listings ranging from around $725,000 to $5 million depending on location and water access. Camp Ground cottages sit toward the bottom of that range, and brokers who work the segment have long described them, in the words of one longtime Vineyard broker quoted in that same 2012 profile, as simply "the low end of the market."
That characterization holds because the price is capped by structure, not just by size. A buyer cannot finance the land because there is no land to finance. A buyer cannot rent freely because the association restricts it. A buyer cannot resell to just anyone without going through the association's process. Every one of those constraints removes a layer of buyer pool and financing flexibility that a conventional Oak Bluffs property has, and every removed layer shows up as downward pressure on price.
What doesn't change
What the leasehold structure does not touch is location, and location is most of what makes these cottages desirable in the first place. A Camp Ground address puts an owner a short walk from Circuit Avenue, where Nancy's has long drawn a crowd for lobster rolls and harbor views and Offshore Ale Company serves its own beer alongside pub food. It puts an owner steps from the Tabernacle, the open-air ironwork structure at the center of the district that still hosts concerts and community gatherings through the season, and within earshot of Grand Illumination Night each August, when the cottages are strung with paper lanterns in a tradition that predates most of the town around them.
None of that changes because the ground beneath the cottage belongs to someone else. If anything, it's the reason these homes hold buyer interest despite the financing hurdles. People aren't purchasing a conventional real estate asset here. They're purchasing a specific, historically protected slice of Oak Bluffs that happens to come with an unusual ownership structure attached.
A few questions worth asking before you make an offer
Can I get a conventional mortgage for a Camp Ground cottage? Often not through a national lender, since there's no land to collateralize. Buyers typically work with island banks that understand and will lend against the leasehold structure.
Can I rent the cottage the way I would a typical Oak Bluffs property? Rental terms are set by the association, and its own rental guidance restricts things like pet policies for tenants. Confirm current rules with the association before assuming a cottage will function like a standard vacation rental.
Does buying a cottage make me a member of the Camp Meeting Association? The association refers to purchasers as leaseholders, and its site describes the buying process in those terms. Historical reporting describes a formal application to join, though the exact requirements today are worth confirming directly with the association rather than assuming they've stayed static.
If you're weighing an Oak Bluffs purchase and trying to figure out which submarket actually fits your goals, whether that's a Camp Ground cottage, a harbor-area condo, or a more conventional single-family home, the details behind the price tag matter as much as the price tag itself. The team at Donnelly + Co. works Oak Bluffs and the rest of Martha's Vineyard year-round and can walk you through what a given property actually comes with before you write an offer. Contact us to talk through your options.
