Agents at Home: John Oliveira Doubles as Designer for Renovation of His Historic Westchester Home
by ELLIMAN INSIDER TEAM
March 2025
By David Hay
John Oliveira bought his first property when he was a 19-year-old freshman at Pace University in Pleasantville, New York. It was a multi-family home in Westchester County, and he has managed it ever since. Although Oliveira comes from a family with deep roots in real estate, that first purchase was an early signal he had grander ambitions for himself.
Since joining Douglas Elliman as an agent in 2016 and launching his five-agent team in 2017, he has built a business providing end-to-end real estate services in points north of New York City, specifically targeting buyers relocating from there. Little did he know that five years later, he and his fiancé, Dean Holtermann, would be on the same trajectory.
The couple was living in Greenpoint, Brooklyn, with Oliveira commuting up to Westchester and Greenwich, Connecticut, when they decided to make the move from their 1,000-square-foot apartment overlooking the East River. It wasn’t long before Oliveira found a large, historic house in the charming Rochelle Heights section of New Rochelle, and they bought it.
Built in 1920, next to the former home of actors Ruby Dee and Ossie Davis, the house was very much a product of its time: dark and cramped, full of character perhaps but hardly contemporary. The kitchen was small, pushed to one side. To say that it needed work, the couple soon learned, was an understatement.
Oliveira, soft spoken and determined, and Holtermann, an interior designer and founder of Dean H Designs, were undeterred. They embarked on an ambitious remodel, politely referred to as a “gut renovation.” But, as evidenced by his early gamble on buying a house when in college, Oliveira is undaunted by a challenge. (Since his initial purchase, he has taken ownership of another five properties.)
As he now tells it, a lot of his motivation for this new project, and many an idea for what it could look like, came straight from his professional experience with sizing up what clients had purchased and sold in the neighborhoods where he works and knows so well.
“I saw all the new kitchens and bathrooms, what they were doing with landscaping and thought, ‘Why couldn’t we do this?’ ” he said.
Having worked with the same builder to upgrade his other properties, Oliveira brought him on board. However, he and Holtermann were determined to do all the design work and subsequent construction supervision on their own. While they hired an architect to submit official plans and documentation when necessary, the scope of the “remodel” was entirely their own vision. It called for expanding the house from its original 3,000 square feet to a much larger, more open residence totaling 5,000 square feet.
On the first floor, they pushed the north-facing walls of the house outwards, creating an expanded living area next to a spacious kitchen with a large, central console. Out from this, they added a wide terrace that runs along this side of the house, itself enclosed by signature arches. They installed the latter as an homage to the period when the house was built (all plans had to be submitted to the City of New Rochelle’s Historical and Landmarks Review Board). Directly below, they put in a 16’ x 35’ swimming pool that extends out into the sloping garden.
“All this could be seen from the homes below, so the HLRB wanted to ensure it would look like it fit in comfortably with the existing neighborhood,” Oliveira explained.
The windows along the front and side facades were widened and lengthened so as to bring more light and a sense of openness inside.
They also didn’t shy away from such luxury touches such as the 18’ x 18’ Rosso Lavanto marble walls that line the master bath or a large, glass cube that occupies one end of the master bedroom and serves as a spacious walk-in closet. Stepping inside, I couldn’t help but observe how neat and organized it looked.
“Yes,” Oliveira admitted with a smile, “we’re a little OCD!”
The renovations took nearly three years while the couple lived in a rental apartment in downtown New Rochelle. Once they moved in, they quickly learned that Rochelle Heights is a very active neighborhood with many a community event.
“When we were living in Brooklyn, there would maybe only one or two neighbors we’d greet regularly,” Oliveira recalled. “But here, everyone says, ‘hello!’”
For him, living in their new house means having closer proximity to his two offices. Three members of his team work from Westchester while the others are in the Hudson Valley. It’s particularly important for Oliveira to be close to Greenwich. Not only is this about as far north as his targeted buyers—New Yorkers who work in the city—see themselves going, it’s a town with one of the highest per resident income levels in the country. Here he sees his future.
Still, one of the hidden advantages of where they now live is the ease of getting into the city they still love. A free neighborhood shuttle takes them to the New Rochelle station, where they can catch a 35-minute Metro North train to Grand Central Terminal.
Not that spending too much time away from their new home is high on their agenda right now. Spring means planting season, the irrepressible Oliveira noted: “Our work is cut out for us.”
Both grand and modern, the house is not only a reflection of the couple’s ambitions and desires, but also it symbolizes the multi-dimensional approach to real estate that Oliveira embraces: property owner, adviser, dealmaker, and now successful designer and renovator.
All the more experience and expertise he can now share with his clients.
David Hay is a well-known architectural writer and playwright. His stories have been featured in The New York Times, Dwell and New York.
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John Oliveira
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