Frank Sinatra’s Former Los Angeles Home Finds a Buyer for $5 Million

Frank Sinatra’s former Los Angeles mid-century home, now a prime Hollywood filming spot, sold for $5 million on Tuesday.

The boxy, glass home on a promontory in Chatswood was rented by Sinatra in the 1960s and was an industry party spot and “playground” for the elite during Hollywood’s Golden Age, according to the listing. It’s since become a popular filming location, more recently setting the backdrop for multiple music videos from Miley Cyrus’s album “Endless Summer Vacation.”

Sinatra’s former address, which includes the main home on a 4-acre parcel and a 9-acre plot with a guest house, was built by mid-century master William Pereira for Chase Bank heiress Dora Hutchinson.

Besides music videos, it was featured in the long-running TV show “Mad Men” and the 2006 movie “Dreamgirls,” and hosted a Hermés launch party in 2022.

According to its listing, “every studio, every production designer and every location manager knows about this fabled property,” that generates between $750,000 and $1,200,000 annually in rentals.

The main 4-acre property listed for $12.75 million in 2022, Mansion Global previously reported .

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Last year, Rock Asset Management Trust took over the estate in a foreclosure sale for $2.1 million. “Between reliance on a single revenue stream, Covid and the [2023 Hollywood] writers’ strike, the owners were unable to service the mortgage obligations,” said the sellers’ agent, Craig Knizek at the Agency.

Rick Wolfen, president of Rock Asset Management, did not immediately respond to requests for a comment.

Previously, the main property and its neighboring parcel with the guest house—which once housed Marilyn Monroe and was reportedly a rendezvous location during her affair with John F. Kennedy—were listed together for $21.5 million.

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“While this listing has been over-priced for the past 13 years, under new ownership, it finally is ready to sell, for the right fair market value,” the most recent listing read.

Tuesday’s buyer also paid $3 million for the larger guest-house parcel that is now primed for new development, separated into 11 single-family lots.

The L-shaped Midcentury Modern house faces a classic California valley panorama. The main living space on one end connects to a stretch of outdoor lounges under a trellis lined with succulents. The trellis extends past the 50-foot pool into an indoor gym and massage room.

Knizek said that he thinks the modernist masterpiece had still been “underutilized” and that the space has even more potential. Think corporate retreats, restaurant collaborations and weddings, he said.

The buyer, who could not be identified, is “someone who appreciates the history and the architecture and appreciates the investment income opportunities,” Knizek said.

The home, with modernist accents like white tile floors, a dais in the bedroom, and wood panel walls, has four bedrooms and six bathrooms.

“I anticipate that the house gets spit and polished, to take it to a whole elevated level,” Knizek added.

For Jack Freeman, a compelling interior should not look as though it was completed in a single shopping trip.

The founder and designer behind FREEMAN & CO prefers rooms that develop through art, travel, commissioned furniture and objects collected over time. It is an approach that treats the home less as a decorative project and more as an evolving portrait of its owner.

“I am a true believer in collecting versus decorating,” Freeman says.

That distinction underpins the international practice he has built across private residences, hotels, property developments, yachts and private aviation. Its projects stretch from Point Piper, Vaucluse, Circular Quay and Toorak to Mayfair, Bel Air and the Caribbean.

Although the locations and architecture vary considerably, the work is connected by a restrained design language. Natural stone, warm timbers and sculptural furniture establish the foundation, while art, bespoke lighting and individual objects give each interior its identity.

The objective is not to overwhelm a room with obvious symbols of expense. It is to create an environment that feels calm, layered and particular to the people living within it.

“The greatest luxury isn’t about excess,” Freeman says. “It’s about creating an oasis where you come home and feel immediately grounded — effortlessly chic and deeply personal.”

Collecting instead of decorating

Decorating can imply the completion of a room: selecting the required furniture, filling the available walls and producing a coherent finished image.

Collecting is less conclusive.

A collected interior has room to change as its owners travel, discover artists, inherit pieces or reassess how they use their home. Its character comes from the relationship between objects rather than adherence to a single brand or season.

That does not mean placing unrelated pieces together without discipline. The designer must understand scale, proportion, material and provenance well enough to create a dialogue between them.

A contemporary artwork might sit beside a historic piece of furniture. A precisely detailed new interior may be interrupted by an irregular object made by hand. Smooth stone can be balanced by timber, textiles or a patinated metal surface that becomes richer with age.

The tension between those elements is part of the appeal.

For Freeman, art is not an accessory to be added once the furniture plan is complete. It forms part of the architecture and atmosphere of the room from the beginning.

Lighting is considered in the same way. Beyond its practical purpose, a bespoke fitting can operate as a suspended sculpture, changing both the room’s composition and the way its materials are experienced after dark.

A design perspective shaped by travel

International travel plays a significant role in Freeman’s creative process.

Design fairs such as PAD Paris and Salone del Mobile in Milan provide opportunities to encounter emerging designers, established galleries, new materials and collectible furniture away from the filter of social media.

More spontaneous discoveries can prove equally important.

“Sometimes it’s the simple things,” Freeman says. “That piece found on a shopping trip with a client in Paris, stumbling across an artisan’s workshop, or a special memory that forms the narrative of the story.”

Objects selected during travel bring more than visual interest into a home. They carry an association with a place, maker or experience, giving the client a connection that cannot be reproduced by ordering an entire interior from a catalogue.

Freeman’s influences are international, but his projects are not conceived as replicas of Parisian, Milanese or Californian style. Each commission responds to its architecture, setting, natural light and the daily lives of its occupants.

A waterfront Sydney residence demands a different treatment from a Mayfair townhouse. A Caribbean estate shaped by brutalist architecture and reflecting pools calls for another response again.

The designer’s role is to absorb those references without allowing them to overwhelm the individual qualities of the property.

Designing the complete experience

FREEMAN & CO extends beyond conventional interior decoration.

The practice’s stated services include interior design and architecture, project management, property acquisition, development advice, concept design, documentation, furniture and lighting design, procurement and art curation.

That breadth allows the team to become involved before a room’s dimensions and finishes are fixed.

Early participation can be important at the top end of the residential market, where architecture, landscape, interiors, technology and art must operate as one environment. Decisions about ceiling heights, wall dimensions, sightlines and lighting can directly affect where art is installed or how custom furniture is proportioned.

The practice can then carry those decisions through to procurement and final installation, maintaining the design narrative as a project moves between architects, builders, specialist craftspeople, dealers and suppliers.

Its residential portfolio includes a South Coast retreat conceived as an escape from urban life, a Caribbean estate with reflecting pools, an East Coast-inspired Palm Beach residence and a Mayfair townhouse organised around an expressive drawing room.

The studio also says it has worked on highly tailored Sydney residences with values exceeding $100 million, although the private nature of such commissions means individual addresses and clients are not always disclosed.

A home that can keep changing

The risk in creating a perfectly resolved interior is that it can become too static — a composition that looks exceptional in photographs but leaves little room for life.

Freeman sees the home as something that should evolve with its owners.

“I love the evolution of design,” he says. “We are talking about people’s lives, and as they evolve, so too should their private sanctuaries.”

That evolution might involve adding art, reupholstering a significant piece, adapting rooms as a family changes or making space for objects gathered through future travels.

The original design needs to be strong enough to accommodate those layers.

This may be the clearest expression of Freeman’s approach to luxury. It is not simply access to rare stone, collectible furniture or commissioned craftsmanship. It is the creation of a personal environment whose meaning deepens rather than diminishes with time.

Fact box

Designer: Jack Freeman

Role: Founder and managing director

Practice: FREEMAN & CO

Base: Australia, with international projects

Project locations named by the practice: Point Piper, Vaucluse, Circular Quay, Toorak, Palm Beach, the NSW South Coast, Mayfair, Bel Air and the Caribbean

Sectors: Private residences, hotels, residential developments, private aviation and superyachts

Services: Interior design and architecture, property development, project management, property acquisition, documentation, furniture and lighting design, FF&E procurement, interior dressing and art curation

Design philosophy: Collected, personal interiors shaped by art, craftsmanship, travel and enduring materials

Website: free-man.co

Frank Sinatra’s Former Los Angeles Home Finds a Buyer for $5 Million

Jack Freeman believes the most compelling interiors are not decorated, but collected. The FREEMAN & CO founder creates layered, personal spaces shaped by art, travel and craftsmanship.