If in 1996 you’d told Randy Rapaport, then a child psychologist for the Portland, Oregon, school system, that he’d become a successful real estate developer, he would have said you were, well, crazy. But that is just what happened when he got to talking with architect Jeff Stuhr at a local greasy spoon. Before long the two were drawing on napkins and scheming up ways to add flavor to the city’s built environment.

Rapaport had dabbled in real estate investing but had never built anything bigger than a birdhouse. Holst Architecture, the firm whose principal he’d met over bacon and eggs, had never designed a condo before. “It was a case of don’t ask, don’t tell,” Rapaport says with a laugh. “But it was easy for me to jump in with Holst—I could see they had talent. It was synchronicity.”

The result of that serendipitous meeting is the Belmont Street Lofts in southeast Portland. Completed in 2004, the 27-unit project is credited with ushering in a new wave of boutique multifamily housing projects nestled into Portland’s historic neighborhoods. At four stories, it’s slightly taller than most of the adjacent commercial buildings. On this stretch of Belmont Street, the structure joins a burgeoning array of eclectic shops, eateries, and cultural offerings, like the old firehouse museum, displaying an 1879 Amoskeag steam pump, and the neon-ensconced Avalon Theatre arcade, where video games and Skee-Ball cost a nickel. A few doors down one can visit Stumptown Coffee for cappuccino, the Blue Monk for live jazz, Theater Theater for local stage productions, or Zupan’s market for groceries inside a renovated old dairy.

In the Belmont District—which spans 50 to 75 square blocks—60 percent of residents are renters, paying from $800 a month for a studio to $4,000 for a two-bedroom stand-alone house with a backyard. Despite the youthful overtones and the muffled cries of gentrification that can plague any city, the neighborhood vibe is a seamless blend of blue collar, hippy, and Parent Teachers Association, many of whom prefer to walk or bike rather than drive their car through their daily routines.

The contemporary, clean-lined rectangular exterior of the Belmont Street Lofts might at first seem to be at odds with its context, but the façade, an interwoven matrix of permeable wire-mesh balconies, wood cladding, and floor-to-ceiling windows, gives the building the warmth and texture of an established Northwest landmark, blending with existing Craftsman bungalows while recalling the designs of local midcentury architects like Pietro Belluschi.

Architect John Holmes, of Holst Architecture, chose Brazilian ipe for the exterior, despite the Northwest’s unwritten rule that a wood façade will quickly succumb to the rainy climate. “Everyone kind of looked around the room and said, ‘No one’s done that. There must be some reason.’ But little by little we just eliminated the questions. Now you’re seeing it all over town.” The resulting pattern of clustered beams suggests de Stijl executed in wood.

Rapaport hung on to one of the top-floor units and now occupies the building’s southwest corner. Because the building looks out onto a school athletic field, there’s an unobstructed view of the sunset, which the open plan and large windows take full advantage of. Rapaport’s loft isn’t large—just under 1,000 square feet with one bedroom—but 12-foot ceilings, clad in a light auburn-hued fir, create the illusion of spaciousness.

When it comes to decorating, Rapaport’s influences are clear. He’s unwaveringly devoted to the Flaming Lips, the indie-rock band from Oklahoma City. In the hallway, a promotional poster for At War With the Mystics, the band’s latest album, immediately grabs a visitor’s attention. Mounted on the kitchen wall is a poster commemorating the Lips’ recent show in Bend, Oregon, which Rapaport co-produced. On it is a laser-etched cutout of these lyrics: “Who knows, maybe there isn’t a vein of stars calling out my name.”

Rapaport has seen the Flaming Lips perform countless times and the band’s lead singer, Wayne Coyne, has become a friend. “I’ve told Wayne that the spirit of the Flaming Lips is in this building,” Rapaport says. The loft also reflects Rapaport’s budding interest in art collecting; he’s particularly focused on the wave of young creative talents who have been moving to Portland in droves over the last few years. Thanks to a friendship with Ruth Ann Brown, owner and curator of the nearby New American Art Union gallery, he has adorned his loft with vibrant oil paintings from represented artists there, like Timothy Scott Dalbow and Rose McCormick. Two photos by Jim Lommasson, chronicling the interior of a hurricane-ravaged New Orleans church, hang in the master bedroom. “I’m really interested in the spiritual resonance of objects,” explains Rapaport.

Aside from the Flaming Lips, art collecting, and architecture, the youthful 46-year-old developer simply loves to talk, with conversation buzzing from philosophy to restaurants and back again to music and architecture. “They’re all connected,” he says. Some of the first people to sign on as Belmont Lofts tenants were Rapaport’s friends—those people who are only too happy to banter late into the evening—giving the building a slightly fraternal feel.

For Brooks Jordan, one such resident and friend, their initial encounter wasn’t so loquacious. The two met at a Buddhist silent meditation retreat outside San Francisco several years ago. When Jordan decided to relocate his tech company to Portland and was looking for a home, he and Rapaport were more than ready to break their shared silence.

“We have the most incredible people here,” says Jordan, who lives in a two-bedroom unit with his wife and two young children. “Sometimes my wife feels drawn to having the house and backyard experience, but with the quality of this building and the people living here, it’d be hard to leave.”

Another tenant, attorney Sanjiv Kripalani, treats his move to the Belmont as a renewal, discarding his old furniture to stock his new loft from scratch. “I was going for a cross between 2001: A Space Odyssey and A Clockwork Orange,” Kripalani explains. Hence the futuristic Ball chair by Eero Aarnio and mid-century-modern Mies daybed.

Kripalani is also president of the Belmont Street Lofts homeowners’ association, and he proudly opens a kitchen drawer to reveal a family-size pack of 9-volt batteries he keeps just in case someone’s smoke alarm loses power and starts beeping. The sense of community at the Belmont Lofts, he says, reminds him of Bombay where he grew up. “Randy actually cared about who moved in here.”

Despite reports of America’s condo boom subsiding, Rapaport and Holst Architecture have a handful of other projects in the works. “Derivative architecture doesn’t hold its spirit very well, but I think true quality and design stand out in the market,” Rapaport says. “It can be scary to take on risks as a developer, but the way to get great architecture is to support creativity.”

Rapaport sometimes gets exhausted by the countless meetings, hearings, and phone calls that come with being a developer, and threatens to drop everything and follow the Flaming Lips’ next tour. But then he comes home. With the afternoon sunshine pouring into his living room, it all seems worthwhile again. Unsurprisingly, Rapaport quotes the Lips to best describe his enthusiasm: “I stood up, and I said yeah.”