Woody Harrelson’s most recent real estate purchase is as thoughtful as it is unconventional.
The True Detective actor and environmental advocate bought the Inn at the Black Olive, a 38-suite eco-friendly boutique hotel located in Baltimore’s historic Fells Point neighborhood, for $4.5 million.
The property, known for its sustainable design and organic operations, had long been a favorite stop for Harrelson — a place he stayed frequently during film shoots in Maryland.
Now, after years of friendship with the inn’s founders, he has taken ownership of the beloved local landmark, deepening his personal and professional connection to the city.
A Purchase Rooted in Friendship and Sustainability
Harrelson’s acquisition of the Inn at the Black Olive wasn’t a typical celebrity investment.
The property was originally developed by his longtime friend Darius Wilkerson and the Spiliadis family, who also operate several farm-to-table restaurants in Baltimore.
Known for their dedication to sustainability, the Spiliadis family built the inn using natural materials such as reclaimed wood, organic plasters, and energy-efficient systems — values that align closely with Harrelson’s well-documented environmental lifestyle.
The actor first stayed at the inn in 2011 while filming Game Change and reportedly fell in love with its eco-conscious ethos. Over the years, he became a regular guest and friend to the family behind it.
When the opportunity arose to buy the property in late 2024, he seized it, ensuring that the hotel’s original mission of green living would continue.
The Inn’s Legacy in Baltimore
Located in the heart of Fells Point — one of Baltimore’s oldest and most culturally rich neighborhoods — the Inn at the Black Olive has long stood out for its commitment to sustainability.
Each of the 38 suites was designed to incorporate natural light, renewable materials, and energy-saving technology. The hotel also emphasized organic dining and wellness-focused amenities, distinguishing it from traditional luxury stays.
Even after the 2014 foreclosure, when Harrelson and business partner John “Jack” Dwyer purchased the inn for $4.5 million, the Spiliadis family remained at the helm, preserving its reputation for quality and authenticity.
Harrelson’s later full acquisition in 2024 reflected both a renewal of his ties to the city and a reaffirmation of the property’s founding principles.
A Vision for Preservation and Renewal
Public filings suggest that Harrelson plans modest updates rather than sweeping changes. The focus will remain on eco-friendly hospitality — solar energy, locally sourced food, and toxin-free interiors — with selective renovations aimed at enhancing comfort and long-term sustainability.
For Harrelson, who has often spoken about the intersection of mindfulness, nature, and creativity, this investment is as much a lifestyle choice as a business move.
The actor, who has supported environmental and regenerative agriculture causes for decades, views the inn as an extension of those principles.
A Baltimore Connection That Runs Deep
Though not a Maryland native, Harrelson has developed a lasting relationship with the Baltimore community.
His frequent stays, public bike rides through the city, and advocacy for local, sustainable living have made him a welcome figure in Fells Point.
His purchase of the Inn at the Black Olive represents more than ownership — it’s a continuation of a relationship built on shared values and mutual respect.
By keeping the inn’s operations true to their origins, Harrelson has preserved a rare example of green hospitality within a historic American city.
The move reflects the actor’s lifelong dedication to living consciously — and his ability to turn even a real estate deal into an expression of purpose.