Holly Madison forks out $8.7 million for some Windsor Square history

It’s been awhile since we’ve written about a house in the historic Hancock Park/Windsor Square neighborhood of Los Angeles. That’s poor taste on our part because the mansions there are some of the most beautiful in the city. Think grand old dames chock-full of style, memories, and ghosts of the party days of yore.

Windsor Square, for those who may not know, is located in central Los Angeles, specifically in a highly urban and heavily-trafficked part of town. This very wealthy neighborhood is notably more ethnically diverse than most other rich parts of LA — some 40% of the residents are Asian, mostly of Korean ancestry. There is also a large Hispanic minority population.

Back in the day — the Roaring Twenties, to be specific — Windsor Square was the most exclusive neighborhood in Los Angeles, jam-packed with rambling mansions designed by the top architects of the day. Many of those homes, believe it or not, still stand and have been well-preserved.

Although the area fell somewhat out of fashion decades ago when many rich folks migrated westward — to the 90210 and surrounding environs — home values have come roarin’ back in a big way. In recent years, prices have spiked so high that they are now nearly comparable with the flats of Beverly Hills! Okay, not quite, but you get the point. It’s mighty expensive out there.

Witness today this large Mediterranean Revival style mansion, which was sold back in 2015 for just $4.3 million. The buyer then was a real estate developer who spent a considerable amount of time and money renovating and expanding the premises before attempting to flip the property.

The historic $8.7 million estate

After more than a year on the market and a couple significant price chops, the historic estate has just sold for $8,700,000 to an LLC. The buyer, Yolanda discovered, is a woman named Holly Madison.

For those who may not know, our Ms. Madison is a celebrity who is likely best-known as an ex-girlfriend of the late Hugh Hefner. Though virtually unknown by the public even after her move-in to the Playboy Mansion, she eventually gained great fame by co-starring on the hit TV show The Girls Next Door. While we never saw that particular program, we gather that Ms. Madison made a name for herself that she went on to parlay into a variety of entrepreneurial endeavors.

After her TV show folded, Ms. Madison appeared on Dancing With The Stars, starred in the Las Vegas-based Peepshow, and authored a very successful memoir — Down The Rabbit Hole — which reigned at #1 on the New York Times bestseller list for three straight weeks. She now has more than one million followers on the Instagram contraption.

And since 2013, Ms. Madison has been married to Pasquale Rotella, a former restaurant busboy turned wealthy entrepreneur. Our Mr. Rotella is the founder of Insomniac Events, the largest EDM event producer in the world — they produce the always-popular electronic dance music festival Electric Daisy Carnival (EDC), among other rave productions. While we cannot verify the deets, Mr. Rotella’s net worth has been reported to be in excess of $50 million.

Mr. Rotella & Ms. Madison

The Madison-Rotellas were married at Disneyland and now have two young children — one girl and one boy named Rainbow and Forest, respectively.  And the young family seems to have developed a fondness for the Hancock Park/Windsor Square neighborhood — their new manse is not the first home they have owned in the area. More on that a little later.

Located just a block north of busy-busy Wilshire Boulevard, the Windsor Square manor in question is more than 100 years old, originally built way back in 1914 by noted architects Hunt & Burns — they also built Downtown LA’s celebrated Bradbury Building (which is definitely worth a visit if y’all have never been, FYI). Although the Windsor Square pad’s exterior appears mostly the same as it did back in the Roaring 20s, the interior is almost entirely all-new and all but unrecognizable. Renovation credit goes to the Bowery Design Group.

There are 8 beds and 8.5 baths in a massive 11,826-square-feet of living space. A wideset, gated brick walkway is guaranteed to impress guests and vendors, as it leads past graceful formal gardens and up stairs to the glassy front door.

To the left of the entryway is a formal living room with a large fireplace, to the right is a windowed formal dining room easily capable of seating 10 dinner guests. A long hallway leads back to more informal rooms such as the breakfast nook and family lounge areas.

Throughout the main rooms (and on the stairs) are hardwood floors stained a trendy inky black. The all-new kitchen sports fancy stainless appliances, an island with bar-style seating, and easy access to the backyard patios.

The sumptuous master suite includes a massive bedroom w/sitting area and an equally expansive bathroom. We’re not sure if we love the marble washstand with its trough-like sink and gold cabinetry, but it’s certainly unique. There’s also two private vanities, a soaking tub, and a glassy shower. Also upstairs are four more guest/family suites.

A lower basement level is packed with luxury features including an enormous wine cellar and a home theater with tiered seating (there’s also maid quarters down there). The backyard of the .61-acre property isn’t particularly huge, but it’s certainly plenty spacious and includes a full outdoor kitchen on the back terrace. Next to the pool is a cabana with an outdoor fireplace attached to a wee one-bedroom guesthouse, and the tree-shaded backyard also boasts a large fountain and grassy lawns for kids and pets to play.

Once upon a time Ms. Madison and Mr. Rotella owned a rather lovely Spanish Colonial-style mansion in Hancock Park. To be specific, they bought the fully renovated estate in late 2014 for $7.1 million and lucratively flipped it just two years later for over $8.2 million. Ka-ching! (The buyers were an art-collecting couple named Joshua & Sonya Roth).

Holly Madison & Pasquale Rotella’s former Hancock Park manse

A few months ago, we heard the Madison-Rotellas were in escrow on Breck Eisner‘s Hancock Park compound, but that deal must’ve fallen through because the house recently sold for $12.5 million in an off-market deal to an entirely different buyer — a Boston-based couple named Robert & Marjie Kargman, whose fortune derives from owning apartments and office units.

Listing agents: Ernie Carswell, Douglas Elliman; H. Blair Chang, The Agency
Holly Madison & Pasquale Rotella’s agent: Jon Grauman, The Agency

10 Replies to “Holly Madison forks out $8.7 million for some Windsor Square history”

  1. It’s very nice, a lot of older established neighborhoods are making a big come back, even here in Houston Texas where we live. Olde Oaks, River Oaks, you can get a really good deal on a McManshion, That’s if you can pay the taxes and keep up with the landscaping, huge utility bills. I’m thinking patio home or hirise.

  2. very nice home for a seemingly nice family. happy for them

  3. It looks perfectly fine now but what a pity that the developers trashed most of the original woodwork inside the house. A few years ago this was a glorious Old Hollywood Gem. Now it’s just another slick modern inside.

  4. Beautiful dream home.

  5. Sandy SantaMonica says: Reply

    How ironic that the lowly Playmate ends up with a very stylish $teal, while the Playboy Mansion is decreed a 100M unremovable wart on a dream property, taylor made for modern masterpiece. A ‘landmark’ designation that came down AFTER its purchase. Gee, thanks LA County!

  6. The Playboy mansion is a beautiful house though and I don’t think the new owner ever planned on tearing it down, even before it got landmark status.

  7. The house that could really use the wrecking ball on that street is the old Spelling mansion. Now THAT is a wart.

    1. Even this fancy house couldn’t keep them together? Say it ain’t so!

  8. Already spending Pasquale’s millions! #BagSecured

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