For admirers of Los Angeles’s architectural heritage and Hollywood’s shimmering mythology, the re-emergence of the Holly Madison Former Home LA listing marks a notable moment in the luxury market. The storied Windsor Square mansion—built in 1914, reimagined through multiple eras of wealth, and inhabited by some of L.A.’s most recognizable creative figures—has returned to the market for $13.4 million, offering its next owner over 12,000 square feet of grandeur shaped by more than a century of cultural evolution.
The residence, long admired for its commanding façade and stately grounds, has been owned by a fascinating roster of personalities. Banking executive Milton Getz commissioned the architectural duo Hunt & Burns to design the four-story home during the early rise of Los Angeles’s elite residential enclaves. More than a century later, Playboy model and Girls Next Door star Holly Madison and entrepreneur Pasquale Rotella purchased it in 2018 for $8.7 million. They infused the historic interiors with a whimsical, Gatsby-era drama, then transferred the property in 2021 to Grammy-nominated songwriter Justin Tranter for nearly $10.3 million. Tranter, known for co-writing global hits like “Sorry,” “Believer,” and “Cake by the Ocean,” carried the home’s glamor into a new creative chapter.
Now represented by Louis Maskin, Kennon Earl and Thomas Davila of Compass, the property seeks its next steward—one who appreciates both heritage architecture and theatrical luxury.
A Revival of Century-Old Elegance
Unlike many Los Angeles estates that have undergone modernistic erasures, the Holly Madison Former Home LA estate remains a celebration of classical details. The approach is anchored by a hedge-lined pathway, which buffers the residence from the street and offers a sense of quiet arrival rare within the city’s dynamic urban fabric. The portico is adorned with black-and-white tile floors, a motif reminiscent of early 20th-century West Coast formalism.
Stepping inside reveals a double-height foyer, its sweeping staircase wrapped in soft carpeting that sets the tone for the home’s blend of opulence and comfort. The adjacent living room gleams beneath a copper-colored ceiling, where tiered crystal chandeliers spill warm light across hand-painted wall coverings and intricate wood moldings. Throughout the home, period craftsmanship coexists with contemporary upgrades—custom gold mirrors conceal televisions, an elegant marriage of nostalgia and discreet technology.
The dining room continues this mood of refined intimacy, enclosed by pocketing doors for private gatherings. During Madison’s tenure, the home’s interiors embraced a “Roaring Twenties meets Great Gatsby” theme, an aesthetic approach that shaped everything from the decorative motifs to the selection of light fixtures. Tranter’s stewardship preserved this cinematic ambiance while tailoring the house to the needs of a working artist and entertainer.
Spaces Designed for Celebration and Daily Living
The main floor includes several rooms imagined for leisure and social gatherings. A game room lined with vintage arcade machines opens to the backyard through tall French doors, welcoming the California sun into its playful, lounge-like environment. The kitchen is a chef-caliber space defined by marble countertops, shaker-style cabinetry, and a split-level eat-in island that subtly encourages everyday togetherness. Top-tier Miele and Thermador appliances complete this culinary showcase.
Moving to the upper levels reveals a series of richly imaginative spaces, including an eclectically wallpapered den that reflects the house’s creative lineage. The full-floor primary suite offers two distinct baths, each with an unmistakable personality. One incorporates a steam shower and a barber’s chair—an indulgent nod to vintage grooming rituals—while the other is anchored by a hand-blown glass chandelier and a stainless soaking tub, creating a contemporary spa environment with an artistic edge.
A Private Speakeasy, Theater, and Guesthouse
The lower level of the home is dedicated entirely to entertainment. A speakeasy-style lounge, wrapped in dark paneling and atmospheric lighting, includes a cigar room and a full wet bar—one of the most alluring remnants of Madison and Rotella’s imaginative renovation. A mirrored gym sits beside the home theater, which is designed with tiered seating to create a cinematic experience.
Outside, the grounds extend the narrative of leisurely luxury. A rectangular swimming pool with a Baja shelf sits beside a fireside cabana, while herb gardens, mature trees, and manicured lawns introduce an organic softness to the architectural symmetry of the property. A built-in outdoor kitchen and generous dining terrace encourage long afternoons under the open sky. The pickleball court adds a modern lifestyle amenity, and a separate guesthouse—complete with its own kitchen—sits above the three-car garage, offering an ideal retreat for extended family or long-term guests.
A Neighborhood Rooted in Prestige and Accessibility
Windsor Square remains one of Los Angeles’s most desirable neighborhoods, beloved for its historic mansions, lush streetscapes, and strong architectural continuity. Its layout, developed during the early 1900s, prioritizes walkability and tranquility, making it a rare hybrid of old-world residential serenity and urban accessibility. The surrounding community offers easy access to Larchmont Village, Koreatown’s acclaimed dining scene, and the cultural amenities of Hancock Park. Residents enjoy proximity to boutique coffee shops, Michelin-recognized restaurants, specialty grocers, and some of the city’s most respected private schools.
For many prospective buyers, this combination of privacy and location is a major factor. Windsor Square sits just minutes from Hollywood studios, Downtown L.A., and Beverly Hills, making it an ideal home base for entertainment executives, creative professionals, and global entrepreneurs who seek convenience without compromising on architectural heritage.
A Rare Opportunity to Own a Piece of Los Angeles History
Across more than a century, the Holly Madison Former Home LA estate has been shaped by the personal tastes and ambitions of its owners. From its origins as the residence of Milton Getz to its transformation under Madison and Rotella, and finally its artistic refinement under Justin Tranter, the property has evolved while retaining a singular sense of identity. Homes of this scale, craftsmanship, and historical continuity seldom return to the market—particularly in neighborhoods where preservation and prestige intersect so effortlessly.
For buyers who value narrative as much as square footage, this Windsor Square mansion represents a compelling opportunity to join the story.