• Tue. Jun 21st, 2022

Learn about Dave Chappelle’s real estate investments in Yellow Springs, Ohio

  • Comedian Dave Chappelle owns at least $3.7 million in real estate in Yellow Springs, Ohio.
  • He grew up in the town, now lives nearby and aims to build a comedy club there.
  • He is under fire after opposing a development that included affordable housing.

In a town in Ohio, a famous big landlord has been buying properties for over a decade.

From single family homes and apartment buildings to small retail stores, one of the world’s most famous comedians, Dave Chappelle, has developed a significant real estate footprint in and around Yellow Springs, Ohio, where he has spent a good part of his childhood and lives today.

Through his Iron Table Holdings and Pilot Boy Productions, Chappelle owns 10 residential and commercial properties that have been purchased for more than $3.7 million, according to Greene County property records. Chappelle has been investing in properties here since at least 2010, records show.

Chappelle’s influence as a landlord in the city became very clear last week, when he spoke out against a large residential development and threatened to withdraw his investments if the plan went through.

The disputed 143-home project contained many homes priced above the median home value for the village and an additional affordable housing component. The last part of the plan, which was criticized by Chappelle and other residents, was shot down by village council members last week.

Through his spokeswoman Carla Sims, Chappelle said the plan was “half-baked” and “never actually offered affordable housing.” The comedian is also considering turning an old fire station he bought into a comedy club. Sims did not respond to a request for comment on Chappelle’s real estate.

Here’s a look at everything Chappelle has in his hometown.

blue building with green awning next to beige building along sidewalk in Yellow Springs

239 Xenia Ave. in Yellow Springs, Ohio, which Chappelle purchased in 2018.

Greene County, Ohio, Property Records


120 Railroad Ave.

Selling price: $308,900

Purchase date: January 16, 2015

Chappelle purchased this three-bedroom, 1-1/2-bathroom home in January 2015 through his company Pilot Boy Productions for nearly $309,000, property records show. He is now worth more than $433,500, according to an estimate by Realtor.com.

The brick single-family home built in 1900 sits on more than half an acre of land and includes an addition built in 1950, records show.

Photos of the home before Chappelle bought it show hardwood floors throughout, a chef’s kitchen, and 9-foot ceilings. The property is in a commercial area, according to the Redfin listing when it was last sold.

239 Xenia Ave.

Selling price: $599,000

Purchase date: November 5, 2018

Chappelle purchased this commercial property – which is made up of three adjoining buildings, 239 Xenia Ave., 241 Xenia Ave. and 243 Xenia Ave. — for $599,000 through his Iron Table Holdings, according to property records. The Greene County website shows that 239 Xenia Ave. is home to Glen Garden Gifts and Flowers, while the Blue Hairon Salon occupies 241 Xenia Ave.

The comedian plans to renovate the facade of the building and add an apartment with a roof terrace above the ground floor retail, a representative explained at a village planning meeting in August 2020, according to the minutes of the meeting. The renovations would be designed by Crome Architecture, led by local native and now Bay Area-based architect Max Crome, according to the firm’s website.

1540 Xenia Ave.

Selling price: $90,000

Purchase date: December 28, 2017

Chappelle paid less than $100,000 for this commercial-zone property on just over a quarter of an acre, according to property records. The property includes a small building and parking lot, both of which were there in September, according to a Google Maps photo.

a brick house with a gray porch and white columns

An apartment building with offices at 403 Xenia Ave. belonging to Chappelle.

Greene County, Ohio, Property Records


309 Xenia Ave.

Selling price: $485,000

Purchase date: March 4, 2020

In the first of a series of purchases Chappelle made along Xenia Avenue in 2020, this commercial property was purchased in March of that year, according to property records. The brick structure houses a tobacco and hookah shop and includes a brick patio. Inside the shop, there is a spiral staircase and a large fireplace.

403 Xenia Ave.

Selling price: $390,000

Purchase date: June 24, 2020

Chappelle bought this small apartment and office building down the road from several other properties he owns for $390,000 during the first summer of the pandemic. Its value has since risen to over $549,000 according to Realtor.com’s estimate.

The brick building, built in 1900, contains three apartments and four offices, according to the Realtor.com listing. Inside, the building has wood floors, carpeting, and intricate details like a spiral staircase in one unit. A white picket fence surrounds the property which registers at just under a quarter of an acre, according to property records.

314 Dayton Street

Selling price: $480,000

Purchase date: December 1, 2020

Chappelle bought 314 Dayton St., a commercial building on about 1.4 acres, on Dec. 1, 2020, for $480,000, property records show. He planned to use the office space for his business and for local national public radio station WYSO, which serves southwestern Ohio, according to minutes of a village planning meeting the last year.

The building, known as the Union Schoolhouse, had been used as village offices and later as private offices. Chappelle’s company was to construct a two-story addition on the west side of the building, part of which will be the office for the radio station, according to site plans presented by a city official last summer.

150 Railroad Street.

Selling price: $600,000

Purchase date: December 8, 2020

Chappelle paid $600,000 for this four-bedroom family home two minutes from the radio station’s future site, property records show. It was built in 1900 and sits on half an acre of land, according to Realtor.com. It is a colonial style house with a whitewashed brick facade.

a gray office building and parking lot in Yellow Springs, Ohio

1425 Brookside Drive in Yellow Springs, Ohio.

Greene County, Ohio, Property Records


221 Xenia Ave.

Selling price: $400,000

Purchase date: July 21

This commercial property with retail space and a price tag of $400,000 was one of two properties Chappelle purchased last summer, according to property records. It once housed a women’s clothing store called Earth Rose International Imports and was vacant in September, according to Google Maps photos.

1425 Brookside Drive

Selling price: $389,500

Purchase date: July 21

This two-building property located three minutes down the road from 221 Xenia is the second purchase Chappelle made in July last year, according to property records. An office building, storage barn and 25-space parking lot sits on the land, which is just under three-quarters of an acre, according to the property’s listing before it was purchased.

225 Corry St.

Selling price: Not Rated

Purchase date: December 2020

Chappelle bought this former fire station in 2020 for an undisclosed amount, according to property records. The comedian planned to turn it into a comedy club called Live from YS, according to the Dayton Daily News. The redevelopment will also include a restaurant.

Renderings of the proposed comedy club appear to play on the building’s past life, with the words “Firehouse” in lights above the theater’s name. Chappelle said “the greats will come” to the entertainment venue, the Dayton Daily News reported, citing his comments during a planning meeting in September.