It’s a rare opportunity to be able to buy a painting lesson with Allen Whiting, a private barbecuing class in your backyard with chef Steven Raichlen or a wine tasting in the Bordeaux region of France.

But at the 40th annual Possible Dreams auction on Sunday, all three were for sale to the highest bidder, with all the proceeds going to Martha’s Vineyard Community Services.

“This auction truly does make dreams possible,” said event organizer Liza May.

Although the final tally is not complete, Community Services development coordinator Jessica Rogers estimated the event brought in approximately $430,000, with the possibility of more donations still on the way.

At the Winnetu Resort in Katama, the Martha’s Vineyard Regional High School a capella group Soundwave serenaded guests as they picked up their bidding paddles. Most then quickly proceeded to the oyster station, where expert shuckers Chris Murphy and Ted (Cap) Karalekas served up Spearpoint catches, courtesy of Island oyster farmer Jeremy Scheffer. Live jazz from Jeremy Berlin and Eric Johnson rounded out the warm summer evening in Edgartown.

The festivities opened up with a silent auction that included lobster bakes in Menemsha, biplane tours of Chappaquiddick and hayrides at the Farm Institute, along with vacations, staycations and spa-cations from Stowe Mountain Resort to the Charlotte Inn. When bidding ended promptly at five o’clock, Iris Freeman couldn’t contain her excitement.

“I won the family photo shoot!” she gleefully told a friend. “Now I just have to get them to do it.” Her clan arrives August 10.

After the silent portion of the evening, bidders made their way to the big tent and readied their paddles for the live auction with 24 enticing dreams.

“It’s because of you that Martha’s Vineyard Community Services has been able to expand to the growing needs of the Island community,” Liza May told the crowd before the bidding began. “Thank you for coming here tonight and celebrating the people who make this Island unique,” she added.

Nancy Monestime Williams was high bidder for a backstage tour and VIP guest pass to the Late Night with Seth Meyers.

“We’ve had our eye on it in years past,” she said, “so we’re very excited to get to go this year.”

Jack Davies, Chilmark resident and owner of the Washington Capitals, donated one of the most coveted dreams of the evening, inviting four people to enjoy a Caps game from the owner’s box and a post-game visit to the locker room.

“Provided the Caps win!” he promised the bidders, holding up a signed, sweat-stained Alexander Ovechkin jersey also included in the package. A battle quickly ensued, and as the price rose to almost $10,000, Mr. Davies stopped the madness and offered a solution.

“If both people are interested, I’ll just do it twice,” he said. Two nights in the Capitals box brought in $19,000.

A similar bidding war opened up for a full wine tasting and dinner at the Chateau Coutet in France. When the price reached $10,000, one of the bidders, Peter Goodale, said he’d pay the full amount as long as he got two seats at the table. The other interested party, Diane Nordin and her husband Tom Keller, consented. The dream brought in another $20,000 for Community Services.

“I’m crazy,” Mr. Goodale said afterward. “I should probably go find who we’re going to France with!” Ms. Nordin and Mr. Goodale exchanged phone numbers, excited not only for their upcoming vacation, but also for their new friends.

Fred Mollin, a Walt Disney Records bestselling instrumental lullaby artist, donated the final sweet dream of the evening. The high bidder would get the chance for Mr. Mollin to write them, or a loved one, a personal lullaby.

“For some reason, my music puts people to sleep,” Mr. Mollin told the crowd.

Joanne Homlish, who has two new grandchildren, emerged victorious. “I have to somehow figure out how to split it between them,” she said after the bidding ended.

But the most moving moment of the night came when auctioneer Sherry Truhlar asked people to simply donate to the Community Services fund-a-need program, which this year focused on suicide prevention and awareness. David Araujo, director of the Island Intervention Center, a Community Services program, spoke passionately about efforts to work with Islanders at risk, noting that Dukes County has some of the highest suicide rates in the state.

Although the tax-deductible donations officially started at $1,000, a woman raised her paddle to make an announcement.

“We’d like to donate $3,000 in honor of Mr. Araujo,” she said. Community Services had brought in $29,000 before any of the “big” dreams even went up for bid.

“It’s been a great night,” said Ms. May. “Planning for next year starts tomorrow.”

More pictures of the Possible Dreams auction.