Bill Simmons House Luxurious for Rent at $25K Monthly

Bill Simmons’ house is on the market for rent, not for sale, but the offer is as grand as the property itself. Known predominantly for his influential career as a sportswriter and pioneering podcast host, Simmons has decided to rent out his luxurious Los Angeles residence. Priced at a steep $25,000 a month, this home isn’t just a dwelling but a slice of history and modern luxury combined.

Built in 1925, Simmons’ property has been meticulously maintained and recently restored to ensure it meets the standards of today’s high-end rentals while preserving its historical charm. Nestled in the prestigious Windsor Square area of central Los Angeles, the house boasts over 4,200 square feet of living space. This includes grand formal rooms that reflect the light and airy aesthetics typical of Californian homes but with the sophisticated touch of smart built-ins and high-end finishes.

As one steps into the large center hall, the journey through the house begins with a spacious living room on one side and a dining room on the other, capable of hosting large gatherings. The kitchen is a modern chef’s dream, featuring a practical island, stainless steel appliances, and a butler’s pantry, perfect for those who entertain often. Adjacent to it, a sunny family room and a cozy study provide more intimate spaces for relaxation and work.

Upstairs, the personal quarters include four well-appointed bedrooms and three newly updated bathrooms, ensuring comfort and privacy. Ample storage space, a finished attic, and elegant hardwood floors throughout the house underscore the thoughtful design and attention to detail that characterize this remarkable home.

Outside, the property continues to impress with a swimming pool, a bar, a basketball court, and even a home-office setup with a half-bath. This home is not just a place to live; it’s a lifestyle statement, reflective of Bill Simmons’ own dynamic and successful career in sports and media. Whether one is a fan of his work or simply in search of a rental that exudes style and history, Simmons’ home represents a unique opportunity in the heart of Los Angeles.

LocationWindsor Square, central Los Angeles
Size4,200 square feet
Price$25,000 a month
Year Built1925
RoomsLiving room, dining room, kitchen, family room, study, 4 bedrooms, 3 bathrooms
AmenitiesSwimming pool, bar, basketball court, home-office setup with a half-bath
Special FeaturesHistorical charm, modern luxury, smart built-ins, high-end finishes, stainless steel appliances, butler’s pantry
AdditionalFinished attic, ample storage space, elegant hardwood floors


Overview of the Property

Constructed in 1925, the stately home now owned by Bill Simmons is not only a residential property but a piece of Los Angeles history. This home has seen the evolution of one of the city’s most prestigious neighborhoods, Windsor Square, and has been preserved and restored to maintain its historical integrity. The recent restoration efforts were meticulously undertaken to update the living spaces and utilities while retaining the property’s original charm and architectural details. These efforts ensure that the home continues to stand as a testament to early 20th-century craftsmanship and style, making it a significant piece of the architectural heritage of central Los Angeles.


Situated in the heart of Windsor Square, this property finds itself in a quintessentially central part of Los Angeles known for its grand homes and historically significant architecture. The area is well-regarded for its broad, tree-lined streets and well-maintained public spaces, contributing to its reputation as a highly desirable place to live. The property itself sprawls over 4,200 square feet and features a layout conducive to both privacy and entertainment. Architectural features such as high ceilings, large windows, and an elegant exterior facade highlight its grandeur and historical value.

Year Constructed1925
LocationWindsor Square, central Los Angeles
Size4,200 square feet
Architectural FeaturesHigh ceilings, large windows, elegant exterior facade
Historical ValueTestament to early 20th-century craftsmanship and architectural heritage
Restoration EffortsPreserved original charm and architectural details while updating living spaces and utilities
Neighborhood CharacteristicsGrand homes, historically significant architecture, broad, tree-lined streets, well-maintained public spaces

Detailed Description of the Home

Upon entering the home, visitors are greeted by a large center hall, which sets the tone for the expansive layout. This central passage leads directly into the main living areas, including a spacious living room and a dining room capable of accommodating large gatherings. These rooms are designed to blend classic architectural elements with modern aesthetics, providing a bright, airy feel that is both inviting and functional.

The kitchen stands out as a modern chef’s dream, fully equipped with a stainless steel appliance set, a large central island for meal preparation and casual dining, and a butler’s pantry, ideal for more elaborate entertaining needs. Adjacent to the kitchen, the property features a sunny family room and a cozy study, providing comfortable spaces for relaxation and personal or professional activities.

On the upper level, the home boasts four bedrooms, each offering ample space and privacy. The three bathrooms on this floor have been recently refreshed, featuring modern fixtures and finishes. The home also includes significant storage options with extensive closet space and a fully finished attic, which adds a unique element to the home’s layout. Throughout the house, hardwood floors and a sophisticated water filtration system add to the comfort and quality of the living experience.

The external amenities of the home are as impressive as its interior. The backyard is an entertainer’s paradise featuring a swimming pool, a well-equipped bar, and a basketball court, which together create a perfect setting for hosting events or personal enjoyment. Additionally, the property includes a fully functional home-office setup complete with a half-bath, providing an ideal solution for those who work from home but require separation from the main living areas. These outdoor features not only enhance the livability of the property but also reflect the luxurious lifestyle that is attainable in this prestigious Los Angeles neighborhood.

Overall, Bill Simmons’ Los Angeles home is more than just a high-end rental opportunity; it is a showcase of historical significance, architectural beauty, and modern luxury, perfectly suited for those looking to enjoy a distinguished lifestyle in one of the city’s most desirable areas.

EntranceLarge center hall leading to main living areas
Living AreasSpacious living room, dining room for large gatherings, blend of classic and modern aesthetics, bright and airy feel
KitchenStainless steel appliances, large central island, butler’s pantry
Additional RoomsSunny family room, cozy study
BedroomsFour spacious bedrooms
BathroomsThree modern bathrooms with updated fixtures and finishes
StorageExtensive closet space, fully finished attic
Flooring and SystemsHardwood floors, sophisticated water filtration system
Outdoor AmenitiesSwimming pool, bar, basketball court, home-office setup with a half-bath

Bill Simmons’ Career and Contributions

Bill Simmons’ journey from a local sports enthusiast to a national media figure is a tale of passion, innovation, and persistence. Initially gaining a following as “The Boston Sports Guy,” Simmons carved out a niche with his unique blend of sports commentary, pop culture references, and personal anecdotes. His engaging style and sharp insights on basketball, football, and other sports, resonated deeply with a growing audience, ultimately leading him to national prominence.

In 2001, Simmons’ career took a significant leap forward when he joined ESPN. Here, he expanded his repertoire to include not just writing, but also podcasting, which would eventually revolutionize sports media. His podcast “The B.S. Report” became immensely popular, setting the stage for what would become a burgeoning industry. Simmons did not stop at podcasting; he also created the sports and pop culture website “Grantland,” which further solidified his status as a media innovator.


The pinnacle of Simmons’ entrepreneurial achievements came with the founding of The Ringer in 2016. This platform was designed from the outset to merge sports and pop culture journalism with podcasting. Under his leadership, The Ringer flourished, attracting a vast audience and hosting a wide array of podcasts that became cultural phenomena. The success of The Ringer culminated in its sale to Spotify in 2020 for $200 million, marking a significant milestone in digital media and podcasting.

Today, Bill Simmons serves as the managing director of The Ringer, overseeing its strategic direction and expansion in the rapidly evolving digital landscape. In addition to his responsibilities at The Ringer, Simmons also holds a significant role at Spotify as the head of global sports content. In this capacity, he is instrumental in shaping the company’s sports programming and leveraging The Ringer’s assets to enhance Spotify’s global content offerings. His vision for integrating sports media with music and other forms of entertainment continues to influence the industry at large.

Early CareerPre-2001Gained popularity as “The Boston Sports Guy,” known for blending sports commentary, pop culture references, and personal anecdotes.
Joining ESPN2001Expanded into podcasting with “The B.S. Report,” growing his national prominence.
GrantlandN/AFounded the sports and pop culture website “Grantland,” enhancing his reputation as a media innovator.
The Ringer2016Founded The Ringer, a platform merging sports and pop culture journalism with podcasting. The Ringer was later sold to Spotify for $200 million in 2020.
Current Roles2020-PresentServes as the managing director of The Ringer and head of global sports content at Spotify, shaping sports programming and integrating media.

Reflecting on Bill Simmons’ impressive career, it is evident that his influence stretches far beyond the articles and podcasts he creates. His foresight in media and content creation has not only shaped his own career but has also had a profound impact on the landscape of sports and entertainment media. The decision to rent out his luxurious Los Angeles home is perhaps a reflection of his life’s work—constantly moving forward, evolving, and embracing new challenges.

Renting such a prestigious home is not merely a transaction; it’s an invitation into the lifestyle of one of sports media’s most influential figures. For potential renters, this offers a unique opportunity to experience a property that reflects the qualities of its owner: style, sophistication, and a deep appreciation for history and modernity. Bill Simmons’ home is more than just a place to live; it is a testament to the success and creativity of one of the sports world’s leading voices.

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