Today San Franciscans know Jackson Square's quaintest alley, Hotaling Place, as the center of the design-centric neighborhood, home to fashion boutiques such as Allbirds and Isabel Marant and surrounded by stylish eateries including Kusakabe and Quince.

But perhaps few of us really know the history of this cobblestone lane which, back in the 1800s before San Francisco was even called San Francisco, literally sat at the water's edge in what was then the Mexican-controlled fishing town of Yerba Buena. After Yerba Buena was annexed to the United States and renamed SF, a building boom fanned by the Gold Rush expanded the city's footprint, and entrepreneurs such as whiskey magnate Anson Parsons Hotaling came in to set up shop. In the 1860s, Hotaling built his headquarters in the lane that would take his name and, about a century later, the Hotaling Stables building became SF's 11th designated landmark.

Today, that same address houses one seriously refined modern penthouse condominium, and it just hit the market.

Sausalito-based Rossington Architecture and Mill Valley's Van Acker Construction have recently completed a $12 million renovation of the two-level penthouse at 42 Hotaling Place. While the history of the building peeks through in moments such as exposed brick, beams and casement windows, the 6,4000-square-foot home is more reflective of the alley's modern chichi reputation, designed with luxurious spaces for lounging and entertaining.

A spacious great room lets living and dining spaces blend together while custom millwork, to conceal built-in storage, keeps this open area from feeling busy.

The kitchen has built-in appliances, a large walk-in pantry, Neolith Calacatta slab marble countertops, and a full wet bar. When the chef wants privacy from the party in the adjacent dining room, she or he must simply raise an on-demand dividing wall.

The nearby powder room is a glamorous experience of its own with a floating vanity and a backsplash wall tiled in antiqued mirror.

The primary suite holds down a whole wing with clever modern shelving units acting as semi-open dividers between the bedroom and its private media lounge. The suite has a chic fireplace, a boutique-style closet with a center island for jewelry and accessory storage, and a spa-like bathroom with a contemporary soaking tub, floating vanity, and roomy walk-in glass shower.

An address in Jackson Square should mean views of such landmarks as the Transamerica Pyramid and Coit Tower; the penthouse delivers. Ascend a glass-encased stairway to the "sky garden," an urban oasis with a small pond, a bocce lawn, designated space for yoga, a hot tub, a full outdoor kitchen, and a lounge with a television.

Additional amenities in the home include HEPA filtration, air conditioning, and smart home controls. Strategically placed skylights and a soothing organic palette keep the space bright and clean.

Interested in the history of Hotaling Place? Read more at SFGate.

Bedrooms: 3

Bathrooms: 2.5

Size: 3,530 sq. ft.

Asking price: $7,900,000

// 42 Hotaling Pl. (Jackson Square); for more information, visit sothebysrealty.com.