Armed with numbered paddles, bidders battled it out under peaked white tents at the Winnetu Oceanside Resort in Katama on Sunday, pledging $136,250 during the live auction at the 38th annual Art Buchwald Possible Dreams Auction.

Sally Taylor performs. — Ray Ewing

Auction chair Liza May said Monday that between the silent and live auction, raffles, sponsorships and donations the event would raise about $400,000 for Martha's Vineyard Community Services.

Community Services provides year-round services to Islanders through its core programs: Connect to End Violence, Disability Services, Early Childhood programs, Island Counseling Center, Island Wide Youth Collaborative and the Thrift Shop.

Comedian host Jimmy Tingle auctioned off 24 Dreams, including vacations to France, Ireland and Scotland, tickets to the MTV Music Awards, and a sail to Nantucket to spend the day with author Elin Hilderbrand. The Nantucket sail was hottest ticket of the night, bringing in $15,000.

Ms. Hilderbrand was in attendance and said the community support was amazing.

Michael Blanchard, with Community Services director Juliette Fay, donates $10,000 to New Paths Recovery Program. — Ray Ewing

“We [in Nantucket] do care about each other, but this is unparalleled,” she said. The winner will be written into her newest novel, and receive signed copies of her most recent book.

The first three dreams of the night were doubled, awarded to two bidders and bringing in a total of $24,500.

Sally Taylor donated a Reaching Consenses Dream, made extra special this year because this is the final summer on the Vineyard for Consenses, her collaborative artistic venture.

“We’re doing this as a final hurrah,” Ms. Taylor said, before performing a song for the crowd. The dream went for $5,500. Two en plein air paintings created during the event by Traeger di Pietro and Brandon Newton brought in a total of $5,000.

Traeger di Pietro paints the scene. — Ray Ewing

Dan VanLandingham filled in for Allen Whiting to offer an afternoon of painting.

“Allen Whiting is a tremendous supporter of Community Services,” Possible Dreams chair Liza May said. “He was unable to participate this year and is passing the torch to Dan. I promise he is an artist to watch.”

Dreaming with Dan went for $3,000.

Along with the live dreams, bidders browsed tables full of silent auction items and super silent auction items and tried their luck in the raffle.

Ray LaPorte, whose wife Bernadette is director of administration and finance for Community Services, was playing the silent auction circuit. He eyed items that included golf and flying. It was his 30th Possible Dreams and he knew the drill.

“We were the successful bidder last year for the Ritz Cafe dream,” he said. This year, the Dream —which includes a party at the Ritz for 50 people with an open bar, food and music from Johnny Hoy and the Bluefish—went for $7,000. The winner was Jeffrey Sudikoff, owner of Edgartown Books and Behind the Bookstore.

Dan VanLandingham painting is auctioned off. — Ray ewing

Before bidding began for the evening, Christine White shared how she and her daughter have benefitted from the early childhood program and the counseling center.

“They say it takes a village to raise a child,” she said. “Community Services is our village. It helped raise Ariel and it helped raise me. So get your wallets out, get your checkbooks out and bid, bid, bid hard.”

Michael Blanchard also kicked off the spirit of giving by presenting a $10,000 check for New Paths, Community Services’ addict recovery program.

“I want to draw attention to the addict treatment services on Island,” he said. “They selflessly help people. I also want to reduce the stigma and a shame. I need to stay healthy too, and when you are a recovering alcoholic, giving back is your medicine.”

There was also a live donation before the auction to fund new playground equipment for the early childhood program. People raised their paddles to donate $1,000, $750, $500, $250 or $100.

“No red tape...we’re going to do it today,” Mr. Tingle announced. More than 40 people donated outright, including Mr. Tingle.