Looking east from Jarvis Street through a metal fence and beyond a construction pit, a rooftop neon sign beckons. The first three letters are extinguished, and the M flickers faintly and struggles to stay alive, but Filmores hotel and gentlemen's club is open for business.

The marquee below is known for its boisterous invitations to the strip club in the basement. Still, the three-storey brick building was designated a heritage property by the City of Toronto last July. Owner Howard Adams finds that "puzzling."

"I don't think this building is exceptional," he said.

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But Filmores is the most recognizable, if not notorious, landmark in the Garden District, an east Toronto neighbourhood coveted by the city as a future heritage zone but also by developers as relatively untapped downtown real estate – a hot spot for high-rise construction. (On the southeast corner of Jarvis and Dundas streets, a construction crane towers above a colossal hole, eventually to be filled with a 50-storey condominium building.)

As such, Filmores is emblematic of the constant struggle between those who would preserve the city's character and those who would transform it.

Mr. Adams, a former lawyer who bought out his father's partner in the building in 2000, says he regularly fields offers to buy the property. Those advances come as the former Jilly's strip club, also a heritage building, at Broadview Avenue and Queen Street gets set to reopen its doors as the more upscale Broadview Hotel. But Mr. Adams is content for now to keep dancers on stage in one of the city's few remaining strip joints.

"It's a better business the way it exists now than it would be as a boutique hotel," Mr. Adams said. "I wouldn't be able to justify the conversion."

At 5 p.m. on a Tuesday, there are only a handful of customers and as many dancers – unlike the 60 or so who perform on weekends. On stage, Whitney, in black lingerie, glides beneath red and orange hemisphere lighting to the Weeknd's Party Monster.

In the hotel lobby, with its green carpeting and sponged beige walls, guests can rent one of 56 rooms on three floors – $73.45 for a room with a sink and $84.75 for one with a full private bathroom. The hotel tends to attract tourists who are unperturbed by the strip club below, according to the front desk clerk.

The hotel began as the Wilton Court Apartments . Adult entertainment wasn't introduced until 1980, when Mr. Adams's father and a partner bought the property. Their plan to redevelop it was scuttled by high interest rates.

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Now, there are more than 100 development applications in Ward 27, which envelops the Garden District (although some date back 10 years and may no longer be actively pursued). Of those, 26 are within the Garden District's borders – Carlton Street to the north, Sherbourne Street to the east, Queen Street to the south and Yonge Street to the west. The ones that cluster around the intersection of Dundas and Jarvis, the heart of this neighbourhood, have all been filed within the past five years.

Many are still under review. It's common for developers to appeal to the Ontario Municipal Board in search of the density and height that the city is reluctant to provide in this neighbourhood.

The city's mandate to serve the Garden District often conflicts with developers' plans for transformation. That's why the local city councillor, Toronto Centre-Rosedale's Kristyn Wong-Tam, for one, would never back shutting down Filmores in favour of high-density infill.

"We would not agree or support the demolition of that property, nor would we support the significant modification of that building to allow high-rise development," Ms. Wong-Tam said. "That may be wishful thinking on behalf of any particular private interest, but it's not part of the city's overall vision for the area."

About 80 per cent of Toronto Centre-Rosedale's almost 90,000 residents already live in apartment complexes of five storeys or more. But Ms. Wong-Tam says more tall buildings are not welcome.

"It's definitely the developers that are pushing the city for height and density," she said. "We see it as a stable, low-rise neighbourhood. We see it as a heritage neighbourhood."

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Several developers who have filed applications or have projects under way in the Garden District declined to comment or did not respond to interview requests. For his part, Mr. Adams would like to see density added to the perimeter to "dilute" the abundance of social housing.

Almost three years ago, the city launched a downtown-east plan that outlines a vision to transform Ms. Wong-Tam's ward while preserving its history. That vision includes creating green space to connect the ward's two parks, Allen Gardens and Moss Park, and accommodating one of Toronto's most marginalized communities with better services and affordable housing.

The ward has 1,060 beds in nine shelters, slightly more than a fifth of Toronto's entire shelter capacity. More than half the beds belong to one of the largest men's shelters in the country, Seaton House, whose location dates back to 1959.

Seaton House is the centrepiece of a proposed $562-million overhaul of George Street. The shelter is slated to be demolished and transformed into a more comprehensive, mixed-gender, long-term care facility. The lost beds will be moved to other, yet-to-be named sites.

Gentrification is a dirty word for many in this neighbourhood. But Bill Colvin, president of the Garden District Residents Association, sees positive changes on the horizon.

"There's a move to bring more balance into the neighbourhood, not to get rid of people," Mr. Colvin said, adding that an influx of residents will help rejuvenate the area.

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Many shelter users are regular customers at George's Pizza and Panzerotto, as are Filmores patrons. Owner Speros Barliakos fears that one day development will price him out of the neighbourhood. "We're in the middle of it here. We're getting squeezed on either side."

Local resident Richard Sabourin, a 53-year-old retired first responder who spends time volunteering, knows development is coming. He wants to see street-level vitality preserved, even if his view of the community's fabric doesn't necessarily include Filmores.

"I don't have any love lost for strip clubs. It doesn't really mean that much to me. I just ignore that it's even there," Mr. Sabourin said. "I would love to see it not there and for us to develop beyond it."

Mr. Colvin, a Garden District resident for 15 years, sees Filmores in a different light. "In my perspective it's always been a good neighbour."

For his part, Mr. Adams admits he's still open to offers, even if he won't discuss them publicly.

"Until somebody convinces me that there's a better use for the site, I'm going to continue what I'm doing," he said. When pressed for his asking price, he said simply: "I'll know it when I see it."