When Ed and Leslie Fine set about updating their home, set high on a hill in San Francisco’s Cole Valley, it wasn’t simply a matter of knocking down walls and raising roof beams. Built by Ed’s parents in 1939, and purchased from his mother a few years back, the two-story house was freighted with memories.

“To me, it was just a box—beautiful, but a box,” says Leslie, a product manager at Salesforce. “Whereas for Ed, it was, ‘But we can’t mess with the lip of the staircase, because that’s where I used to launch my Matchbox cars!’”

Before: Exterior

After: Exterior

“My childhood memories added some challenges, for sure,” agrees Ed, a data scientist who teaches at UC Berkeley. “There were times I needed to step away, so I could distinguish between what was sentimental and what was best for the design and architecture of the house.”

Before: Staircase

After: Staircase

Before: Living Room

After: Living Room

Helping to balance nostalgia and aesthetics, architect Jennifer Weiss—who went to high school with Ed and was reconnected with him through a colleague—retained the house’s original footprint while raising ceilings, expanding windows, carving out bedrooms, and catapulting the facade into the current century. “Because of the constraints, we ended up with a more interesting—and less generic—house than if we’d started from scratch,” she says.

Before: Kitchen

After: Kitchen

On the main floor, surgical cuts created an open flow around the kitchen, formerly marooned behind a series of rooms that also blocked the garden. The Art Deco–inspired stair rail, designed by Ed’s mother, was preserved, as was one of the Moorish-style arches. Upstairs, Ed’s childhood bedroom, now the master suite, was transformed from a dormer warren with tiny windows and a ceiling that peaked at six-and-a-half feet into an expansive space with a wrapping wall of glass and views of the city, bay, and three bridges. An outdoor porch, often swathed in fog, was enclosed and reborn as a guestroom.

Before: Upstairs Hall

After: Upstairs Hall

After: Master Bedroom

Because his father died when Ed was a teenager, it’s especially meaningful that he now works at the same desk used by his dad (the laminate top having been replaced with a walnut one). And sitting on the kitchen sill is another relic of his past: “My son Gabriel came running in one day all excited, and said, ‘Hey, Dad, look at this car I found in the back yard.’ It turned out it was one of my Matchbox cars, from when I was a kid.”

Related Reading: This Renovated Esherick Perfectly Frames the San Francisco Bay

Project Credits:

Architect: Jennifer Weiss Architecture / @jennifer_weiss_architecture

Builder: Farallon Construction

Structural Engineer: Holmes Structures

Lighting Design: Jennifer Weiss Architecture

Interior Design: Jennifer Weiss Architecture

Casework Design: Jennifer Weiss Architecture