Matt Dillon House has become a topic of interest for fans who want to know where the legendary actor calls home. The acclaimed Hollywood star, known for his roles in classics like “The Outsiders” and “There’s Something About Mary,” splits his time between two stunning locations that reflect his artistic lifestyle and international romance. And his living arrangements tell a fascinating story about a man who’s successfully balanced American roots with European sophistication.
Who is Matt Dillon?
Matt Dillon has built an impressive legacy in Hollywood over more than four decades. The actor started his career at just 14 years old when he was discovered cutting class at Hommocks Middle School in Larchmont, New York. Since then, he’s become one of the most respected actors of his generation, with a net worth estimated between $40-50 million as of 2025. His wealth comes from his extensive acting career, directing projects, and various endorsements including brands like Skechers and Dickies.
Born Matthew Raymond Dillon on February 18, 1964, in New Rochelle, New York, he grew up in a close-knit Irish Catholic family. His father Paul was a portrait painter and sales manager, while his mother Mary Ellen was a homemaker. Matt is one of six children, and his brother Kevin Dillon is also an actor, best known for the HBO series “Entourage.”
Throughout his career, Matt has accumulated wealth through blockbuster films like “There’s Something About Mary” (which grossed $369 million), “Crash” (for which he received an Academy Award nomination), and “Drugstore Cowboy.” He’s also ventured behind the camera, writing and directing the 2002 film “City of Ghosts” and the 2020 documentary “The Great Fellove.”
While specific information about Matt Dillon’s car collection isn’t widely publicized, the actor maintains a relatively private lifestyle. There’s no public information about him owning yachts, private islands, or private jets. Instead, he’s known for his artistic pursuits, including painting and collecting Latin music on vinyl records. He reportedly has one of the largest Latin vinyl record collections in the world, particularly Cuban music on 78rpm discs.
| Full Name | Matthew Raymond Dillon |
|---|---|
| Date of Birth | February 18, 1964 |
| Age | 61 years old |
| Birthplace | New Rochelle, New York, USA |
| Net Worth | $40-50 million |
| Profession | Actor, Director, Producer, Writer |
| Relationship Status | Dating Roberta Mastromichele (since 2014) |
| Primary Residences | Manhattan, New York and Rome, Italy |
Where Does Matt Dillon Live Now?
Currently, Matt Dillon lives between two vibrant cities that fuel his creative spirit. He maintains an apartment in Manhattan, New York, where he was photographed speaking from during a 2023 interview with Parade magazine. But that’s only half the story. The actor splits his time equally between the United States and Rome, Italy, where his girlfriend Roberta Mastromichele is from.
Matt met Roberta, an Italian actress, dancer, and choreographer, at the Rome Film Festival in 2014, and they’ve been together ever since. Their relationship has now lasted over 10 years, making it one of the longest relationships of his life. Before Roberta, Matt dated several Hollywood actresses including Cameron Diaz from 1995 to 1998, Brooke Shields, and Heather Graham.
The actor has spoken about how living in Europe brings out his creative side. During an interview, he explained that he does a lot of painting in Rome and that most of his friends there are artists and painters. It’s a place where he can stay creative and feel inspired. The couple is frequently spotted attending film festivals and premieres in Rome, where they seem to have established a comfortable life together.
Matt Dillon House
Matt Dillon House represents two distinct but equally sophisticated lifestyles. His Manhattan residence serves as his American base, keeping him connected to the entertainment industry and his New York roots. Meanwhile, his Rome dwelling with girlfriend Roberta Mastromichele offers him the artistic environment he craves.
The Manhattan apartment is located in one of New York City’s most desirable neighborhoods, though specific details about the exact address and property value remain private. Manhattan real estate is notoriously expensive, with average home values in the New York area reaching over $700,000 as of 2025. Given Matt’s substantial net worth and his status as a Hollywood star, his Manhattan property is likely worth considerably more than the average.
In Rome, Matt has established a second home where he spends approximately half of his time. The Italian capital provides him with the perfect backdrop for his artistic pursuits. Rome’s rich cultural history, stunning architecture, and vibrant art scene align perfectly with Matt’s interests in painting and music. The city also allows him to be closer to Roberta’s family and immerse himself in Italian culture.
1. Where Is Matt Dillon House?
Matt Dillon House in Manhattan sits in the heart of New York City, though the exact location has been kept private to maintain his security and privacy. What we do know is that he’s been spotted in various Manhattan neighborhoods, including the West Village, and has been seen shopping in Soho and attending events at Madison Square Garden. The apartment serves as his primary American residence and his connection to the film industry.
His Rome residence is where Matt spends the other half of his year with Roberta Mastromichele. Rome has become his creative sanctuary, a place where he can paint, collect Cuban music, and plot his next directorial projects. The couple has been photographed attending numerous events in the Italian capital, including movie premieres at the Timvision Floating Theatre and the Venice Film Festival.
The actor’s choice to split his time between New York and Rome makes perfect sense for his lifestyle. New York keeps him plugged into Hollywood and American cinema, while Rome offers the artistic inspiration and romantic atmosphere that feeds his creative soul. Both cities are cultural powerhouses with world-class art museums, theaters, and music scenes that match Matt’s sophisticated tastes.
2. Features of Matt Dillon House
While specific architectural details of Matt Dillon House in Manhattan aren’t publicly available, we can make some educated assumptions based on his status and preferences. Manhattan apartments at his level typically feature spacious layouts, high ceilings, large windows with city views, and modern amenities. Given Matt’s artistic nature and his love for painting, his Manhattan home likely includes a dedicated studio space or at least excellent natural lighting for his creative work.
The Rome residence he shares with Roberta probably reflects Italian design sensibilities with historic charm, possibly featuring traditional Roman architecture mixed with modern updates. Italian homes often include beautiful terraces or balconies, marble details, and spaces designed for entertaining guests. Given Matt’s passion for music, both residences likely have sophisticated sound systems to enjoy his extensive vinyl collection.
Matt’s homes are probably decorated with his own artwork and his collection of Cuban music records. The spaces would need to accommodate his artistic lifestyle while providing comfortable living areas for both him and Roberta. Privacy is clearly important to the couple, as they’ve managed to keep most details about their homes out of the public eye despite Matt’s fame.
Matt Dillon Real Estate Portfolio
Information about Matt Dillon’s complete real estate portfolio is limited, as the actor has maintained significant privacy about his property holdings. Unlike some celebrities who openly discuss their real estate investments, Matt has kept details about his properties largely confidential.
What we do know is that he grew up in Mamaroneck, New York, in a modest household with five siblings. His childhood home was in a typical suburban neighborhood, a far cry from the Manhattan apartment he owns today. This progression from middle-class roots to owning property in one of the world’s most expensive cities demonstrates his successful career trajectory.
Before settling into his current arrangement between Manhattan and Rome, Matt likely owned or rented various properties throughout his career. During his relationship with Cameron Diaz in the late 1990s, the couple probably shared residences, though specific details aren’t publicly documented. As someone who’s worked in Hollywood for over 40 years, Matt has undoubtedly moved through different living situations as his career and personal life evolved.
There’s no public information about Matt owning multiple investment properties, vacation homes, or real estate outside of his primary residences. Unlike some actors who build extensive property portfolios, Matt seems to prefer a simpler approach, focusing on two homes that serve both practical and emotional purposes. His Manhattan apartment keeps him connected to his American career and family, while his Rome residence nurtures his artistic soul and his relationship with Roberta.
Some reports suggest he may own property in Los Angeles, given that it’s the center of the film industry, but this hasn’t been confirmed. What’s clear is that Matt Dillon’s real estate choices reflect his values: privacy, creativity, and meaningful relationships rather than flashy displays of wealth.
Conclusion
Matt Dillon House represents more than just where the actor sleeps at night. His dual residences in Manhattan and Rome tell the story of a man who’s successfully balanced his American roots with his European romance, his Hollywood career with his artistic passions. From his modest beginnings in Mamaroneck, New York, to his current life split between two of the world’s great cities, Matt has created a lifestyle that supports both his professional ambitions and his personal happiness.
The $40-50 million actor has chosen privacy over publicity when it comes to his homes, keeping the specific details of his properties away from public scrutiny. But what shines through is that his living arrangements reflect his true priorities: staying creative, maintaining meaningful relationships, and living authentically. Whether he’s in his Manhattan apartment working on his next project or in Rome painting with his girlfriend Roberta, Matt Dillon has found his perfect balance between two worlds.