Tim Dillon has built a multi-million dollar real estate portfolio that mirrors the chaotic energy of his comedy. The former subprime mortgage broker turned podcaster owns properties stretching from Los Angeles to the Hamptons.
Fans of The Tim Dillon Show know he talks about housing markets, Zillow listings, and real estate scams almost as much as politics. His rants about overpriced California homes and scuffed realtors have become legendary. But behind the comedy, the numbers tell a serious story.
Dillon’s real estate holdings include a $4.6 million Hollywood Hills mansion, a $3.98 million Hamptons getaway, and a short-lived experiment in Austin, Texas. His net worth is estimated at $12 million, according to Celebrity Net Worth.
TL;DR: Tim Dillon owns a $4.6 million Spanish-style home in the Hollywood Hills (bought from actor Thomas Middleditch in 2022), a $3.98 million Hamptons property in Southampton, and briefly lived in Austin before returning to Los Angeles. His real estate moves are a core part of his podcast persona.
Quick Facts about Tim Dillon House
| Property | Details |
| Hollywood Hills Home | $4.6 million, 2,933 sq ft, 3 beds, Spanish-style |
| Previous Owner | Thomas Middleditch (Silicon Valley actor) |
| Purchase Date | September 26, 2022 |
| Listing Price (2024) | Just under $5 million |
| Hamptons Property | $3.98 million, Southampton, NY (May 2022) |
| Austin Home | Brief stay during 2020-2021 pandemic relocation |
| Net Worth (est.) | $12 million (per Celebrity Net Worth) |
The $4.6 Million Hollywood Hills Mansion
In September 2022, Tim Dillon closed on a 2,933 square foot home perched above Mulholland Drive in the Hollywood Hills. The purchase price was $4.6 million, or roughly $1,568 per square foot.
The seller was Thomas Middleditch, best known for starring in HBO’s Silicon Valley. The transaction closed on September 26, 2022, and was widely reported by real estate outlets including Robb Report and Yahoo.
Why This Purchase Became Comedy Gold
Dillon has turned his experience buying this house into some of his most popular podcast moments. In Episode #382 of The Tim Dillon Show, he launched into an extended rant about California real estate, openly questioning whether he overpaid.
He joked about begging his listeners to buy the house from him. The episode became a fan favorite and cemented the Hollywood Hills home as a recurring character on the show.
Key Features and Property Specs
- Price paid: $4,600,000 (September 2022)
- Square footage: 2,933 sq ft on a 0.33-acre lot
- Price per square foot: $1,568
- Style: Spanish-style architecture
- Location: Hollywood Hills, above Mulholland Drive, Los Angeles
- Bedrooms: 3
- Previous owner: Thomas Middleditch
- Listing price (2024): Just under $5 million
Design and Architecture
The Hollywood Hills home features classic Spanish-style architecture. This style is common in the hillside neighborhoods of Los Angeles, known for stucco exteriors, terracotta roof tiles, and arched doorways.
The property sits on a 0.33-acre lot with views of the surrounding hills. Its elevated position above Mulholland Drive provides privacy, a feature that appeals to entertainment industry buyers. The interior includes three bedrooms and an open-concept living area.
Robb Report described the home as having a “celeb-pedigreed” background, noting its appeal to celebrity buyers. The Spanish Colonial aesthetic blends traditional Mediterranean design elements with modern Los Angeles living.
The $3.98 Million Hamptons Property
In May 2022, Dillon purchased a property in Southampton, New York for $3.98 million. The original asking price was $4.5 million, meaning he negotiated roughly $520,000 off the list. The New York Post first reported the deal.
The Hamptons purchase carries special meaning. Dillon grew up on Long Island, and buying a home in Southampton represents the ultimate “I made it” milestone for a New York native. He frequently references East Coast wealth and Hamptons culture on his podcast.
Dillon initially denied the New York Post story on The Tim Dillon Show, calling the report “lies and fabrications.” However, property records confirmed the transaction, and he later acknowledged the purchase during later episodes.
The Short-Lived Austin Experiment
During the 2020-2021 pandemic, Tim Dillon joined a wave of comedians who relocated to Austin, Texas. Joe Rogan had already moved, and the city was drawing entertainers seeking lower taxes and fewer COVID restrictions.
Dillon bought a house in Austin but quickly grew frustrated with the experience. He complained about the extreme Texas heat, unreliable local contractors, and what he called “scuffed realtors.” In summer 2021, he announced he was moving back to Los Angeles.
Wikipedia notes that as of March 2021, Dillon had returned to Los Angeles after briefly living in Austin. In 2025, articles from Yahoo News and Chron.com highlighted that several of Rogan’s comedian friends, including Dillon, openly regretted their Texas relocation.
The “Fake Business” of Real Estate
Dillon’s obsession with real estate comes from personal experience. Before comedy, he worked as a subprime mortgage broker during the housing boom that led to the 2008 financial crisis. He has described selling mortgages to people who could not afford them.
That background gives him a unique perspective on housing markets. His “Fake Business” segments on the podcast frequently target real estate scams, predatory lending, and the absurdity of American housing prices. He understands the industry from the inside.
This is why his rants about his own properties resonate with fans. He is not just complaining about housing costs. He is a former insider exposing the system he once participated in.
Recent Updates and Market Context
In early 2024, Dillon listed his Hollywood Hills home for just under $5 million. The listing was covered by Robb Report, Yahoo, and Mansion Global. As of recent reports, the property remains on the market.
The asking price represents a roughly $400,000 premium over his $4.6 million purchase price. However, after agent fees and carrying costs, the actual profit margin would be smaller. Los Angeles luxury real estate has softened since 2022, which may explain the extended time on market.
In January 2024, Dillon shared on Instagram that he bought his parents a house. The post received over 94,000 likes and demonstrated his continued investment in real estate beyond his personal residences.
Dillon’s net worth has grown alongside his podcast success. With an estimated annual income between $1.5 million and $2 million from podcasting, live shows, and his Netflix special “I’m Your Mother” (released April 2025), his real estate portfolio remains a significant part of his wealth.
Frequently Asked Questions
Where does Tim Dillon live?
Dillon currently resides in Los Angeles. He purchased a Hollywood Hills home in 2022 and also owns property in the Hamptons.
How much did Tim Dillon pay for his Hollywood Hills house?
He paid $4.6 million for the 2,933 sq ft Spanish-style home in September 2022.
Did Tim Dillon buy a house from Thomas Middleditch?
Yes. Dillon purchased his Hollywood Hills home from the Silicon Valley actor in September 2022.
Did Tim Dillon live in Austin?
He relocated to Austin briefly during 2020-2021 but returned to Los Angeles by summer 2021.
What is Tim Dillon’s net worth?
His net worth is estimated at $12 million, per Celebrity Net Worth.
Is Tim Dillon selling his Hollywood Hills home?
He listed the property for just under $5 million in early 2024. As of recent reports, the home remains on the market.
