Holly Madison’s L.A. Mansion Now Available for $13.4 Million

I still remember the first time I saw Holly Madison’s Windsor Square estate—it felt like stepping into a Gatsby novel right in the middle of Los Angeles. Now, almost four years after she and Pasquale Rotella sold the home to Justin Tranter, the property is back on the market for $13.4 million. That’s a big jump from its previous $10.3 million sale, and honestly, it’s no surprise why: this isn’t just any house—it’s a century-old mansion with eight bedrooms, nine baths, and details that make you pause at every turn.

If you’ve ever wondered what living like a Hollywood star might feel like, this estate gives you a glimpse. From the double-height foyer to the gold-hued living room and a backyard that could host your own private resort, it’s the kind of property that sparks both envy and imagination.

Before we dive into the details, think about this: would you ever consider living in a home with a private speakeasy, a movie theater, and a guesthouse above your garage? Because that’s just the beginning of what this place offers.

Quick Facts: The Property at a Glance

Holly Madison’s former Windsor Square home is a 12,000-square-foot estate with eight bedrooms and nine bathrooms. The asking price is now $13.4 million, slightly below the $13.9 million it was first listed for a couple of months ago.

Built in 1914 for banking executive Milton Getz and designed by the famed Hunt & Burns architectural team, this four-story mansion blends classic charm with modern luxury. The estate sits on over half an acre, hidden behind gates and hedge-covered walls, giving you privacy that most L.A. homes can only dream of.

According to Robb Report, the home’s double-height foyer, gold-hued living room, and chandeliered dining room set the tone for an interior that’s both glamorous and welcoming.

Every corner tells a story—hand-painted wallpaper, art-deco-inspired fixtures, and even custom mirrors doubling as TVs. It’s not just a house; it’s an experience.

Interior Highlights: Glamorous Features

Step inside, and it feels like you’ve walked onto a movie set. The foyer flows into a gold-hued living room warmed by a fireplace, while the dining room with pocketing doors offers privacy for elegant gatherings.

The game room is a nostalgic delight, decked out with old-school arcade machines and a billiards table, while the kitchen is straight out of a dream: shaker-style cabinetry, marble countertops, a split-level eat-in island, and top-of-the-line Miele and Thermador appliances.

Upstairs, the primary suite is an oasis with dual baths—one with a barber chair and steam shower, the other featuring a hand-blown glass chandelier and stainless soaking tub.

If you enjoy exploring celebrity estates, you might also find it interesting how Alec Baldwin recently put his Hamptons farmhouse back on the market for $21M.

Lower-Level Entertainment & Outdoor Oasis

On the lower entertaining level, there’s a speakeasy-style bar, a cigar lounge, a mirrored gym, and a tiered movie theater. Step outside, and the estate continues to impress.

You have a pool, spa, and fireside cabana, a built-in outdoor kitchen, a pickleball court, and mature trees and herb gardens that make the space feel private and lush. There’s also a guesthouse above the three-car garage, perfect for visitors—or even a personal office.

For readers who like to track luxury homes in real time, there’s a WhatsApp channel where enthusiasts share rare celebrity listings, updates, and discussions about properties like this. You might come across insider updates that aren’t widely reported elsewhere.

Celebrity Ownership Timeline

The story of this house is as colorful as its interiors. Holly Madison and Pasquale Rotella bought the property in summer 2018 for $8.7 million, shortly before their divorce in February 2019.

They reimagined the home with a Roaring Twenties meets Great Gatsby vibe before selling it to songwriter Justin Tranter in late 2021 for around $10.3 million.

Tranter is no small name—he’s co-written hits for Justin Bieber, Imagine Dragons, and DNCE. He previously owned a Hollywood home he sold in 2022, which adds another layer to the home’s celebrity story.

For more insight into unique celebrity residences, check out Jay Schottenstein’s Florida penthouse that recently listed at $34 million.

Architectural & Historical Significance

This isn’t just a luxury home; it’s a piece of history. Built in 1914, the mansion was designed by the Hunt & Burns team, renowned for their elegant and enduring Los Angeles architecture.

Ornate details like hand-painted wallpaper, elaborate crown molding, and art-deco-inspired fixtures make this house stand out in a market crowded with modern builds.

Even small touches, like mirrors doubling as TVs and custom gold finishes, blend historic charm with modern technology. You get a sense that every detail was considered for both aesthetics and function.

If century-old luxury homes fascinate you, you might also enjoy Liberace’s legendary L.A. mansion with its piano-shaped pool.

Windsor Square: Luxury Neighborhood & Location

If you haven’t explored Windsor Square, think of it as one of L.A.’s hidden gems.

Historic, tree-lined streets, and elegant estates make it a neighborhood that oozes prestige without feeling overly flashy.

The location is unbeatable—minutes from Beverly Hills, Hancock Park, and central Los Angeles hotspots—yet the estate’s gates and hedge-covered walls give the privacy most A-listers crave.

Market & Investment Perspective

Celebrity homes often carry a built-in prestige that can make them appealing investments—and Holly’s mansion is no exception.

Similar L.A. estates, like Jessica Simpson’s and Lori Loughlin’s properties, have seen appreciation after celebrity ownership.

From an investor’s point of view, a historic, architecturally significant estate with entertainment-ready spaces in a prime location is more than a home—it’s a trophy asset.

Even if you’re not buying, it’s fascinating to consider what goes into the valuation of such a high-profile property.

Practical Tips for High-End Buyers

If you’re dreaming about owning something like this, privacy is critical—gated estates, security systems, and hedge-covered walls aren’t optional.

Historic properties often come with restrictions or maintenance quirks, so inspections and long-term upkeep should factor into your decision.

Also, consider lifestyle.

Homes like this aren’t just residences—they’re entertainment hubs. That speakeasy, movie theater, and pool area are amazing, but they also require time, staffing, and investment to maintain properly.

Bottom Line: Is $13.4M Worth It?

Honestly, this house is the kind of property that makes you dream. It’s architecturally stunning, historically significant, and full of lifestyle amenities that few other L.A. estates can match. The celebrity factor and location in Windsor Square give it added prestige, which may justify the $13.4 million asking price.

What would you do first if you had a private speakeasy and a backyard resort in your L.A. home? I’d love to hear your thoughts—drop a comment below and share your ideas.

Also, if you want to explore more celebrity homes and similar listings, visit our celebrity real estate category here for all the latest updates and stunning estates.

Disclaimer: The information in this article is based on publicly available sources and media reports. Prices, ownership details, and features are subject to change. This content is for informational and entertainment purposes only, not financial or investment advice.