Boston.com34%
So you want to live on Martha’s Vineyard? 2%
By Cameron Sperance0%
7/31/2026, 5:46:44 AM
BS Summary: This article contains 11 faulty reasoning types, including Self-Serving Bias, Status Quo Bias, and Confirmation Bias, with Hindsight Bias as the most egregious example at 2.6% saturation with 43 hits. Analysis detected 285 faulty-reasoning hits from 1,627 analyzed words, generating a BS Score of 8.3% and a BS Rank of 2% (22,508 of 22,831 articles). This article is better (less manipulative) than 98.60% of the article peer group.
On an October morning in 2021, Keija Minor was doing what she did most mornings from her home in Oakland, Calif.
She was scrolling Martha’s Vineyard real estate listings while having her coffee.
A 1980s Cape-style house on nearly 1.5 acres in Oak Bluffs stopped the scroll.
“For years, I’ve always looked at real estate listings on the Vineyard, just to look,” Minor said.
“However, when I saw prices skyrocket during COVID, I started to panic that if I didn’t buy soon, I could be priced out.”
She sent the listing to her mother and a family friend, Boston-based developer Duane Jackson, who were both on island and toured the property on her behalf.
Minor made an offer from 3,000 miles away and closed two days before Christmas.
From California, she renovated the house with help from Paul Lazes of Rock Pond Studio.
“When I bought my house, it had a small galley kitchen and no dishwasher.
On the other side of the kitchen wall was a large dining room.
I knew immediately that I wanted to knock down the wall between them and flip the space,” she explained.
“What I didn’t know was that to remove the load bearing wall between the kitchen and dining room would take months first to level the floor and then to install a massive steel beam to hold up the second floor.
You know how you never want to see sausage being made?
That’s how I felt about the beam installation.”
Minor’s route to that home had many stops.
A graduate of Howard University School of Law, she practiced corporate law in New York City before jumping to media, where she ran Gotham and Uptown magazines and made history at Condé Nast as the company’s first African American editor-in-chief when she took the helm of Brides.
She later served as chief operating officer of Ebony Media Group.
Today, she is a real estate agent with the Point B team at Compass on Martha’s Vineyard — and, as of 2024, she’s a year-round Oak Bluffs resident.
But the island’s not new to her; she grew up spending summers there.
“When I was a kid, the Vineyard wasn’t fancy — or at least my Vineyard wasn’t fancy.
We didn’t have air conditioning, and on most days you could get on the ferry without a reservation.
As kids, we could roam free,” she said, recalling the hours she spent grabbing rings at at Flying Horses Carousel.
“I always thought I’d live here when I retired, but remote work and my move into real estate created a path to making the move much sooner,” Minor said.
“With the rise of remote work, more seasonal residents found themselves spending more time in their homes here, which in turn, led to more restaurants and stores staying open longer.
More folks discovered how nice it is to be here in the offseason, or spend Thanksgiving here, or come for Christmas in Edgartown.”
The transformation, she said, runs both ways.
“I now wear Hunter Wellies probably five times as often as I wear heels,” Minor said.
“I’m gardening for the first time in my life — albeit with mixed results — but as a lady who largely ate out or ordered takeout for the past 20 years, I’m quite proud of my first batch of cherry tomatoes.”
The learning curve to island life got steeper when the temperature dropped.
This past winter ushered in levels of snow the island hadn’t seen in years, and Minor found herself hunting down a plow service, riding out a power outage, and pressing a fireplace she once considered decorative into active duty.
“I was Brooklyn condo ready,” she said.
“I was not [Vineyard homeowner] ready, but I will not make that mistake again.”
One lesson in particular stuck.
“This winter, I deeply cared that I do not have a garage,” she said with a laugh.
Allison Cameron Parry, a Douglas Elliman real estate agent, has lived on the island for 25 years (she arrived as a teenage lifeguard at Chilmark’s famed Lucy Vincent Beach).
She offers a longer view of what year-round life delivers.
“The frog noise is just about the loudest noise I hear,” she said of the blissful quiet and natural beauty of the island.
Winter, she tells curious buyers, has its own rhythm.
According to the Chamber of Commerce, the island’s nearly 200,000 summer residents whittle down to about 24,000 in the offseason.
“It’s the introspection season,” Cameron Parry said, describing the months when islanders take up photography, mah-jong, or breath work, and when privately endowed programs such as Pathways Arts turn the shuttered Chilmark Tavern into a hub of music jams and exhibits.
Vineyard Haven, she said, has become the island’s true year-round downtown, its restaurant scene energized since the formerly dry town began allowing full liquor sales.
Winter in Oak Bluffs is another story.
“The only place to get a coffee in Oak Bluffs is the Keurig machine found in the bank,” she joked
The Martha’s Vineyard market
The Vineyard housing market Minor now works in bears little resemblance to the one she grew up visiting — or even the one she bought into.
In Oak Bluffs, the median single-family sale price ran just under $635,000 in 2018, according to data from The Warren Group.
By 2025, it had more than doubled to about $1.29 million, and through the first half of 2026 it stood at roughly $1.32 million.
Edgartown followed the same arc, climbing from $800,000 in 2018 to $1.7 million last year, and Tisbury nearly matched Oak Bluffs dollar for dollar.
What has collapsed is volume.
The island’s towns combined had 313 single-family sales in 2018 and nearly 400 during the frenzied 2020 market.
Since 2022, annual sales have not cracked 200.
Up-island towns are so thinly traded (Chilmark and Aquinnah each recorded just four sales through June) that a single trophy listing can whipsaw a town’s median by millions.
When Minor bought in the Hamptons a decade ago, she noted, the Vineyard was the more affordable of the two markets.
On a price-per-square-foot basis, she said, they are now roughly at parity.
Getting in the game
Nevette Previd, executive director of the Vineyard Preservation Trust, bought her Vineyard Haven home about 18 years ago with every intention of renovating, flipping, and eventually moving deeper into the woods.
Life intervened, and she and her husband are now raising a teenager (there are six public schools on the island) in that prime downtown location.
But when they recently revisited the idea of trading up-island, the math had turned against them.
Selling would net a handsome profit, she said, but replacing the house would require significant capital on top of the proceeds, even for a fixer upper.
“There’s no way,” Previd said.
“There’s absolutely no way we could get out of the market and in the market again.”
That lock-in effect is one increasingly common in markets across the Cape and Islands and helps explain the island’s vanishing inventory: Even content longtime owners who might otherwise trade up or sideways are staying put.
What Previd sees changing instead is the calendar.
“There was the on and off season, but now there seems to be the midseason,” she said, describing residents who arrive before Memorial Day, linger into October, and return for Thanksgiving and for Christmas in Edgartown, a December weekend she calls “massive, massive, massive.”
Cameron Parry is candid about the trade-offs of living on island.
Construction and renovation costs run at least 30 percent above mainland averages, she said, thanks to labor scarcity and the price of getting materials across Vineyard Sound, and specialists of every kind — from HVAC contractors to pediatric dentists — require patience.
Buyers eyeing historic homes in enclaves such as East Chop in Oak Bluffs face renovation restrictions that can sharply limit expansion.
Her formula for making it work is simple.
“If you have a vision and a little extra liquidity, you can overcome anything, really,” she said.
Previd’s counsel for the smitten buyer is blunter.
“Don’t dive in year-round until you’ve spent three months” in the offseason, she said, because the island’s charms in July say little about its realities in March, and because belonging takes work in a place where roots run generations deep.
Volunteering is the fastest way in, she added, with more than 150 nonprofits on an island where showing up at Town Meeting still counts for something.
For Boston-area buyers who fall in love after a week on the island, Minor’s advice is to get pre-approved, as that will make your offer more attractive, and get ruthless about must-haves versus nice-to-haves, because desirable listings rarely wait around, and closings routinely take 60 days.
Her larger philosophy fits on a bumper sticker: “Life is short, buy the Vineyard house!”
“When I bought my house at the end of 2021, I said to friends who bought in 2019, ‘You’re so lucky you bought before the pandemic.’
Now people say to me, ‘You’re so lucky you bought in 2021 when interest rates were so low,’” Minor said.
“There will always be someone who bought before you or got a better deal; the important thing is to get in the game.”
“It’s the only place where I want things to stay exactly the same,” Minor added about the Vineyard.
“It’s part of the reason I joined the board of Vineyard Preservation Trust.
All these century-old buildings take a lot of resources to maintain.
In addition to the buildings, we have a responsibility to keep the spirit of kindness and community very much alive here as well.
There’s something about the island that makes you cherish it and also want to protect it.”
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