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It was just months into the pandemic when Scott Webster went door to door with flyers and endless enthusiasm, keen to share that he would be finally redeveloping the modest single-family house and squat brick storefront his family owns at 1 Elmwood St. He purchased the property behind Roxbury Community College 29 years ago as an investment and made it his home in 2010. Now, Webster pitched what the property could become: a 65-foot, seven-story building with 47 furnished mini-apartments , with a basement devoted to co-working and showcasing local art.

Special timber flooring would keep energy costs down, he said, and rents would be roughly $2,400 a month. Webster pledged his own money and the help of his two sons, who would manage and live in the building themselves. There would be expanded sidewalks, new trees, and free BlueBikes membership for residents.



Imagine something more grass-roots, Webster said, than the luxury towers snaking down Tremont Street from Northeastern University. Anyways, he mused, why not let a local Black family get in on the deal to build something the city needs, while creating generational wealth for themselves? Advertisement It was a vision born of good intentions. Four years later, it is near collapse.

“Turns out, different isn’t working,” Webster said one rainy afternoon this summer. “I wouldn’t wish this process on anyone else.” Webster expected pushback, of course.

What he did not expect was an eternal saga of scathing meetings and stubborn refusals, or a front-row seat to a development system that sometimes stymies projects the city desperately needs. The Elmwood plan won the approval of the two key city boards, the Boston Planning & Development Agency and the Zoning Board of Appeals, more than a year ago, and most immediate neighbors are on board with leveling the existing buildings there. But the property is within the newly formed Highland Park Architecture Conservation District.

And an influential group of residents argues it is too large, too expensive, and too destructive to the historic character of the neighborhood. The saga is playing out as housing availability in Boston hits dangerous lows. Both state and city officials are pushing to build up transit-accessible parts of the region, to some success.

And Mayor Michelle Wu has prioritized revamping Boston’s onerous development-approval process, creating a city Planning Department that will incorporate a wider range of community voices — even though some of those voices speak up against new housing in their neighborhoods. Advertisement “No matter what you do, there will always be some community group — even if it’s two or three people who may not be abutters — that will declare, ‘This development will ruin the neighborhood,’” said Ted Landsmark, a Northeastern University professor, longtime civic planner, and member of the Boston Planning and Development Agency board. “The challenge that Boston faces is one of answering the question of when enough is enough.

” In Webster’s case, there’s an extra hurdle. Highland Park is one of 10 historic districts in Boston , in which architecture boards are granted an extra layer of authority over development in places deemed worthy of aesthetic and cultural protection. The only one in a majority-Black neighborhood, it was created in 2022 after residents lobbied for decades to protect the stately Victorian and Gothic Revival buildings built before the early 20th century.

When the new district was launched, its commissioners temporarily froze all ongoing projects, including 1 Elmwood. That gave opponents time to marshal their arguments ahead of a make-or-break vote by the commission expected in the coming months. In public meetings, residents skewered the Websters’ team for building apartments for college students under the guise of affordability, including too little parking, and gentrifying the enclave they call home.

Others simply think a 65-foot-tall building does not belong in a neighborhood of multifamily homes, even though several nearby buildings are at least as tall. Advertisement Rod Singleton, a member of the Highland Park Neighborhood Coalition, said he and 200-some people have signed a petition demanding the Websters pump the brakes and instead work “a little TLC” into the existing structure. “I don’t begrudge a Black family building wealth,” Singleton said.

“We’re all out here doing that. Just because you’re building wealth does not mean you need to crap all over the neighborhood where you’re doing it. “The greed that is evident is shocking and misplaced.

” He and others are urging Webster to reduce the height of the building to three stories or fewer. Another suggestion from a resident involved leaving the existing structures intact and instead erecting a small garage in the unused gravel lot behind it. Nearly all are pushing to reduce the rents further.

But the economics of that simply will not work, say Webster and his team. They already cut the number of units from 47 to 39, seven of which would be set aside for people who earn below the area median income. Katie Faulkner, the project architect at West Work, revamped the design to include the kinds of corners, cornices, and double-proportion windows that jive with the surrounding buildings.

Shrinking it any further “would make the whole project unprofitable,” said Minkoo Kang, one of the Websters’ development partners. The Websters estimate they have spent $500,000 drafting plans and paying staff so far. Two members of the development team have been working pro bono for months.

In the meantime, rent and construction prices have soared, making the math behind building it, the cost of materials, time, and labor, tougher. Additional changes could push the Websters to convert the building from rental units to for-sale condos. Advertisement The debate is even more fraught in Roxbury, where the legacy of redlining and urban renewal and modern-day fears about displacement lead some residents to view nearly all new developments with skepticism — from imposing university residence halls to the renovation of White Stadium.

But others contend Roxbury needs to move forward. Development is happening with or without the community, said Christopher Martin Grant, a 26-year member of the nearby John Eliot Square Neighborhood Association. The Websters are a “beautiful, responsible, and honest family” who have lived in the neighborhood for a long time, Grant said, and are equipped to build something that would be a benefit to Highland Park rather than undermine it.

“We are very cautious on what we build in this neighborhood, because of urban renewal and so many governmental acts that have caused people to be wary,” Grant said. When it comes to development, “turning the switch off has always been the thing here,” Grant said. “The question now is: How do you turn that switch on?” The answer could come whenever the conservation district is ready to vote, once a fifth member of the new five-member panel is approved by the city Planning & Development Agency.

A rejection would push the Websters back to the beginning, redrafting the design altogether and presenting it to the community again in a year— that is, if they choose not to kill it outright. Neither Gabriela Amore, the city-appointed preservation planner for Highland Park, nor the commissioners returned multiple calls and emails from the Globe. All Sean Webster wants is to eventually see the fruit of his family’s labor.

Advertisement “This is a lifelong dream that my father has been trying to pursue,” he said, “and it’s about time he achieved it.” Diti Kohli can be reached at diti.kohli@globe.

com . Follow her @ditikohli_ ..

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