Carrie Caldwell, a fifth grade teacher at the Tisbury School, has moved around the Island 10 times in the last six months. Her next move will be her last, after she won a lottery for land on Chappaquiddick.
Carrie Caldwell, a fifth grade teacher at the Tisbury School, has moved around the Island 10 times in the last six months. Her next move will be her last, after she won a lottery Tuesday for a three-acre parcel of land off Quammox Road on Chappaquiddick.
“[I’m] beyond excited, beyond grateful,” Ms. Caldwell told the Gazette after her name was called. “I think more than anything I feel grateful just that the opportunity was out there.”
Held at the Edgartown select board meeting on the first floor of the town hall, the affordable housing lottery was done in conjunction with the Dukes County Regional Housing Authority and the Edgartown affordable housing committee. The lottery included 15 hopeful landowners who had qualified. The meeting was also streamed on Zoom. Board chairman Margaret Serpa pulled the names from an old wooden box. Selections were made in descending order with Ms. Caldwell’s name called first.
The meeting room was filled with over 20 people and at one point more chairs had to be set out to accommodate the group. Mark Hess, the town affordable housing committee chairman, lamented what that indicated about the scarcity of affordable housing on the Island.
“Unfortunately, there’s a lot of people here which is not great, but somebody is going to get a great property today,” Mr. Hess said. “If you’re not picked today, keep trying, it will happen some day, we appreciate your patience and your hard work.”
The Chasin family created the Quammox West subdivision, which included one lot set aside for affordable housing. Households earning up to 150 per cent area median income, which is about $110,000 for a one-person household, were eligible to apply. Ms. Caldwell will be given the deed-restricted land at no cost, and will pay for construction out of her own pocket.
“It’s been quite a process and we appreciate all the effort that the individual participants have put in,” said David Vigneault, executive director of the Dukes County Regional Housing Authority, at the drawing.
Ms. Caldwell said she first moved to the Island after graduating from college in 1995. She returned in 2015, but held a job teaching at a boarding school on the mainland. About a year ago she decided she wanted to be on Island full time, knowing full well how hard it would be to find stable housing.
“It’s been a fight to be here,” Ms. Caldwell said. “The last 10, 11 months have been the hardest of my life.”
Having lived on Chappy briefly in the past, Ms. Caldwell said she is familiar with its rural landscape and is committed to planting native vegetation and building a house which fits in with the island within the Island.
“I really want to build as green as possible,” Ms. Caldwell said.
She said too that she would like to have a roommate — partly because living on Chappy alone could get lonely, but also because she knows from experience how hard it is to find housing on the Island.
“Preferably a teacher,” she said of her potential roommate.
Mr. Hess urged the 14 people who were not selected to hang in there.
“We know what the Island means to you and your children. You don’t want to leave and we’re trying to remedy that situation,” Mr. Hess said. “It’s heartbreaking to see so many people in need of a good, affordable home that work so hard on the Island here.”

Comments
GODBLESS YOU MS. CALDWELL
GODSPAL MVGODBLESS YOU MS. CALDWELL.WHEREVER YOU GO THERE YOU ARE,YOU CAN THANK YOUR BLESSED SURROUNDS THAT CHAPPY IS NOT FAR!!!!GOOD FOR YOU...
Couldn't think of a more
Adam Wilson OAK BLUFFSCouldn't think of a more deserving person!
Congratulations, Ms. Caldwell
Robby K Oak BluffsCongratulations, Ms. Caldwell. An investment in our islands future through an incredible teacher and role model.
Very exciting!!! Wouldn’t it
Matt D EdgartownVery exciting!!! Wouldn’t it be nice if they could made 3 lots and supply land for 3 families, this would be a very thoughtful exception!
Congrats Ms. Caldwell!! We
AnonymousCongrats Ms. Caldwell!! We are rooting for you!
What a poor use of land and
Perpetuating Sprawl... ChappyWhat a poor use of land and prime example of the town's terrible consideration of zoning. This 3-acre lot should have been put into preservation. Using up such land for affordable housing just perpetuates developmental sprawl which is eating away at the character of the island... We need dense affordable housing in existing developed areas, and we need to preserve undeveloped areas for the common good and enjoyment of all islanders... It's great that this teacher now has a home, but time will prove out how poor planning like this will negatively impact the island for centuries to come...
Maybe if you were a stellar
Eddie Mac North NoepeMaybe if you were a stellar Vineyard teacher committed to your job and had to move 10 times you would be singing a different tune. A three acre subdivision parcel cannot be considered "sprawl". The island does a great job of preserving open land but is just beginning to address the affordable housing needs of the people that work here. Ms Caldwell is a perfect example of that and we should be proud that the system is working. Congratulations to her for persevering for so long !
Congrats!!!
Jim EdgartownCongrats!!!
Great start, but I wish they
Laura Wiener Arlington, MAGreat start, but I wish they could build 4 units in a single structure instead of just one. There’s so much need.
Considering this is a 3 acre
Density is good ChappyConsidering this is a 3 acre lot, would there have been an opportunity to actually put several homes / apartments on the property?
Welcome to our special little
Annie ChappaquiddickWelcome to our special little community!
Congratulations to Ms.
Jan B Edgartown/MarylandCongratulations to Ms. Caldwell! This is very exciting! Wouldn’t it be nice if we could make an exception in the future and make 3 one acre lots for more housing for those in need?
Congratulations Ms. Caldwell
John Aldeborgh KatamaCongratulations Ms. Caldwell for sure. I fear however that her struggle is far from over as building costs on the island are frightfully high. My brother, who has owned land on the island for over 25 years finally built a home, that was finished last August, and his builder (a local builder, who was excellent) told him that building costs have risen by roughly 1/3 since he originally quoted my brother. Prices have jumped, not including the land, if he were to re-quote the same project from $300 sqft to $400 a sqft. The supply chain crisis, increased regulations, generational high levels of inflation and now rising interest rates are creating a perfect storm of hardship for our young people. All of this together is only going to exasperate the affordability challenge for almost everyone.
That 3-acre plot is most
Katherine Kunhiraman (Kakie Siebel) Berkeley, CaliforniaThat 3-acre plot is most likely part of our 40-acre domain throughout my childhood. Three barefoot months, my feet can still recall the feel of the grass and sand beneath them. Chappaquiddick in summer was the most generous of givers; berries, grapes, beach plums, clams, scallops and crabs, fish - we dreamed of growing old beside Katama, sailing across to South Beach to lie all day under the sun. I hope it all works out for Ms. Caldwell. She sounds like she shares the Chappaquiddick spirit. Maybe one day I will knock on her door and regale her with stories of the past.
All the feels for your recall
LeslieAll the feels for your recall of fond memories!!! Your description took me there immediately!
This land belonged to my
Barbara Siebel Thomas East Hampton, NYThis land belonged to my family since 1949, the Chasins bought it from my mother (for a pittance, especially compared to today’s values!). We have been sad ever since that it was no longer ours. But so happy it went to a deserving citizen of the island!
What a wonderful story!
Matt H AtlantaWhat a wonderful story!
Congratulations Carrie!!! I
Susie Fauteux Oak BluffsCongratulations Carrie!!! I am so very happy for you!!!
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