Neighbors Decry Housing Proposal Behind Dairy Queen

The prospect of three new two-story apartment buildings behind the Dairy Queen in Edgartown, with a total of 15 rental units, 18 bedrooms and 18 parking spaces, drew strong opposition from neighbors when the Martha’s Vineyard Commission opened a public hearing on the proposal March 5.

Multiple residents of Pinehurst Road, directly to the rear of the eight-acre site at 238, 240 and 242 Upper Main street, testified that the development would loom over their homes and bring additional traffic to an already congested neighborhood.

The 242 Upper Main street property changed hands in December, 2020 for $1.5 million as part of a wave of acquisitions by David and Jessica Rosenberg, a father and daughter affiliated with the Newton-based developer Sawyer Realty Holdings, who now lease the Dairy Queen to its operator and have residential tenants in a house to the rear of the site.

In a separate transaction on the same date, the Rosenbergs’ limited liability corporation (LLC) also bought the adjoining 238 Upper Main street, including a 2,000-square-foot office building, for $1.05 million. 

In 2021, another one of their LLCs bought the house and land at 240 Upper Main. 

Speaking with the Gazette after the 2020 purchases, Ms. Rosenberg said Sawyer Realty wanted to expand its footprint in hospitality and housing on Martha’s Vineyard.

“Our core focus is affordable and workforce housing for the Island,” she said. 

Corporations affiliated with one or both of the Rosenbergs have bought and redeveloped other Upper Main street properties in recent years, including what are now the Edgar Hotel at number 227 and the Franklin Hotel at number 222.

The newly-proposed apartments at 238-242 Upper Main are not designated for workforce or affordable housing, although Ms. Rosenberg and her attorney Geoghan Coogan said they would be open to considering an income limit of 150 per cent of the area median income (AMI).

They will, however, be restricted to year-round tenants, defined by the Martha’s Vineyard Commission and state law as residing in the home for 10 out of every 12 months. Short-term rentals would be prohibited.

For this reason, Mr. Coogan said, the project should be exempted from the MVC’s housing mitigation policy, which requires developers to provide dwellings or funds to offset the increased need for Island labor caused by additional construction.

“We’re providing year round housing, deed-restricted year round housing,” he said.

The Dairy Queen will continue to lease the front building at 242 Upper Main and retain seven parking spots said to the rear of the ice cream shop, Ms. Rosenberg said.

Tenants of the new apartment houses would have assigned parking spaces along a one-way drive and access to overflow parking at the Franklin Hotel a few doors away, she said.

Pinehurst Road homeowners whose properties back up to the site decried the proposed development.

The five-foot setback shown on the plans means the 30-foot-tall buildings will be 15 feet from the windows of her house, said Jennifer Zaniboni, who also objected to the traffic flow.

“Headlights would be going directly through the driveway into our backyard,” she said, going on to list other concerns including noise, trash and neighborhood congestion.

Neighbor Grace VanDecruze echoed Ms. Zaniboni’s concerns, arguing that the area is already suffering from clogged vehicle traffic and light pollution.

“I think it’s just too many units for a much too small space, especially when we consider the impact on the overall neighborhood, the setbacks, the traffic and safety issues,” Ms. VanDecruze said.

Commissioners are scheduled to continue the public hearing next month.

This article appears in March 13, 2026.