A Newton-based real estate developer has purchased two adjacent quarter-acre Edgartown properties that include the storied Dairy Queen building for $2.8 million, further consolidating land holdings along the town’s Upper Main street neighborhood.

The properties at 238 and 242 Upper Main street were sold in two separate transactions on Dec. 22 to an LLC that has David and Jessica Rosenberg as its principals. The seller is longtime property owner Antone (Tony) Bettencourt.

David and Jessica Rosenberg are both employees of Sawyer Realty Holdings, a real estate management and investment firm based in Newton, with Mr. Rosenberg named as its president and CEO on the company website. Jessica Rosenberg is his daughter.

The iconic Dairy Queen business — one of the only chain franchise eateries on the Island — is separately owned by Edgartown entrepreneur Christopher Celeste and his family, who purchased the business from Mr. Bettencourt in 2017. Mr. Celeste had considered selling the Dairy Queen business earlier this fall, listing an ad in Island newspapers, but confirmed on Monday that he had since changed course.

“We’re no longer pursuing a sale,” Mr. Celeste said. “We’re committing to 2021 and beyond.”

In a separate interview Monday, Jessica Rosenberg confirmed that the Dairy Queen would continue its lease and reopen for the 2021 season, pandemic-permitting.

The Dairy Queen has a long history on the Island, with the current franchise dating to 1992. The ice creamery’s annual spring reopening has turned into a rite of passage for Island schoolchildren, summer residents and others, with roots dating to the 1960s.

All Dairy Queen franchises are locally owned.

The property sale marks the fourth major recent acquisition for the Rosenbergs in the neighborhood. Corporate entities listing one or both as principals own at least four properties on the south side of Upper Main street, as well as the former Clarion Inn on the north side. Mr. Rosenberg was listed as a principal in the group that purchased the Clarion Inn in 2018 for $8 million. The inn has since been remodeled and rebranded as the Edgar Hotel Martha’s Vineyard.

A once largely residential neighborhood with modest single-family homes, the Upper Main street area in Edgartown has undergone transition in recent decades, becoming more commercial as longtime homeowners have sold properties.

The 238 Upper Main street property, which includes a 2,000-square-foot office building that housed a real estate firm and now-vacant tailor shop, sold for $1.05 million, according to publicly available land records. The other parcel at 242 Upper Main, home to the Dairy Queen as well as a small house near the back of the property, sold for $1.8 million.

The office building is now home to Matchpoint Realty. Francois Tailoring has since relocated to 107 Beach Road in Vineyard Haven.

Various LLCs controlled by the Rosenbergs now own four parcels situated on the southern stretch of Upper Main street. Along with 238 and 242 Upper Main, the firm purchased a 3,700-square-foot house at 222 Upper Main street in 2018 for $2 million, according to land records. The firm also purchased a 3,000-square-foot house at 222 Upper Main street in November 2019 for $1.2 million.

Currently, the only building between 222 Upper Main street and 242 Upper Main street not owned by Rosenberg entities is 234 Main street, which includes the China House restaurant as well as a paint shop. The owner is Island builder Norman Rankow.

Meanwhile, land records show that an LLC linked to Christopher Celeste purchased the home at 220 Upper Main street from Steve Ewing, Colin Ewing and a third LLC in November 2020 for $1 million.

Mr. Celeste said the Dairy Queen has a seven-year lease that is set to renew in 2022. He confirmed the family was intent on maintaining the business, despite putting out feelers for a potential buyer this fall.

“The Dairy Queen will be there in 2021, and we’re committed to keeping a thriving business in Edgartown in 2021,” Mr. Celeste said.

Ms. Rosenberg said Sawyer Realty was looking to expand its holdings on the Island, with a focus on workforce and affordable housing, as well as the hospitality industry. She said no immediate changes were planned for the Dairy Queen property, although some minor construction work was being done on the other homes. The homes currently have a mix of hotel staff and others as tenants, Ms. Rosenberg said.

“We love Martha’s Vineyard, and have spent the last couple of years trying to expand our footprint. Our core focus is affordable and workforce housing for the Island,” she said. “We really like the hotel and bed and breakfast space, and feel there’s space for more demand there.”

She said the family has plans to put in an art gallery in the unit that formerly held the tailor shop, and that if the opportunity arose they would be interested in further acquisitions in the area. She also confirmed that the Celeste family would remain as tenants.

“Chris and his family are wonderful tenants, we’re super happy to have them as tenants, and right now there are no changes regarding that,” Ms. Rosenberg said.

Mr. Celeste acknowledged the transition in the neighborhood, considering the recent land purchases

“The neighborhood is changing, that’s for sure,” Mr. Celeste said. “I’m hopeful that’s good for the future of Upper Main street. We slowly have gone through this transition from residential to commercial.”