Jordan Lombardo, left, and Brad Senffner with their French bulldogs Hudson and Haarlem in Upper Manhattan. The couple had rented in New York since moving from Chicago in 2018. For their first purchase, they wanted a two-bedroom with good light and space for entertaining. Katherine Marks for The New York Times

Jordan Lombardo and Brad Senffner met on a dating app in 2017, but they didn’t link up in person until six months later — by accident.

Mr. Lombardo’s mother had come to visit him in Chicago, and the two went out for brunch. As they finished their meal, Mr. Lombardo noticed Mr. Senffner waving to him from across the street, which he found odd — odd enough that his mother cried out, “Who is this old hairy daddy waving to you?”

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“That was when I realized that we spoke before but never met,” said Mr. Lombardo, now 28, who’s from the Pittsburgh area. “I gave him a hug and called him the wrong name: Adam.”

Mr. Senffner asked what Mr. Lombardo’s plan was for the day, and they realized they were both going to check out the same local beach. They’ve been together ever since. A few months after they met, Mr. Lombardo moved into Mr. Senffner’s three-bedroom apartment, which he shared with two roommates for $3,200 a month.

It was time to find their first place together, but Mr. Lombardo, who had only been living in Chicago for a couple of years, had a pretty big ask: He wanted to move to New York, where he’d attended Hunter College for three years and thrived amid the city’s walkability and wonder.

More was at stake for Mr. Senffner, 42, who grew up in a small town south of Chicago. But when Mr. Lombardo asked him to move halfway across the country, the reply was surprising. “We were just driving one day during the holidays, and he was like, ‘Let’s move. Let’s do it,’” Mr. Lombardo said.

The couple arrived in Manhattan in 2018 and tried short-term rentals to feel out different neighborhoods. Their first spot was a one-bedroom in Washington Heights, where they lived for a month. “The sun was the most important thing in the apartment,” said Mr. Senffner, the events director at an upscale restaurant and event space in Manhattan. “It would permeate every space. And we have a grand piano that moved with us, that’s been with me since I graduated college.”

They moved on to apartments in the East Village, then the West Village, and finally Harlem, where they rented a duplex that had only one window per level. They had a private patio, a respite from the darkness inside, where they could entertain friends and let their two Frenchies out without needing to walk them when the winter chill arrived.

The couple got married in that Harlem rental on New Year’s Eve 2023 and started thinking about buying a place. They enjoyed living in Harlem, and also loved the neighborhood vibe up in Washington Heights. They did some research and found that they qualified for a first-time buyer mortgage rate with a budget of up to $800,000.

“There’s a certain convenience that comes with Harlem — transit-wise, connectivity, walkability, all of that,” said Mr. Lombardo, a flight attendant. “I think we've just become accustomed to this and we knew that we would get more for our money in Upper Manhattan.”

They contacted Ashley Jeudy, an agent in the Harlem office at Brown Harris Stevens, who began showing them two-bedrooms that fit their needs, including a great kitchen, lots of light, and pet friendly. The couple wanted enough space to entertain and host overnight guests, and they leaned toward prewar charm instead of newer developments.

The couple tried to stay well under their $800,000 budget so they’d have funds left over to make any space into something of their own. “We assumed that we would do some type of renovation or adjustment,” Mr. Senffner said. “For example, we’ll do a lot of trimming stuff in this space to make it feel more collected, designed.”

Among their options:

No. 1

Two-Balcony Condo in Harlem

Katherine Marks for The New York Times

This updated two-bedroom, two-bath condo with about 925 square feet was in a 1910 brownstone a short walk from the couple’s duplex, so they could remain close to their favorite Harlem spots and subways. The railroad-style unit featured two balconies, though each was only accessible through a bedroom. Both bathrooms had been renovated, and the unit had washer-dryer hookups (though no laundry room), a big open kitchen, and large windows. The building offered a roof deck. The price was $749,000, with about $9,500 in annual taxes and $348 a month in condo fees.

Compass

No. 2

South-Facing Condo in Washington Heights

Katherine Marks for The New York Times

This renovated two-bedroom, one-bath apartment with 925 square feet was in a 59-unit condo from 1920 that was close to Riverside Park, but a little farther from the subway. It had new appliances in the galley kitchen and new fixtures in the bathroom. The full oven, which Mr. Senffner could use for baking, would be a first in any of the couple’s New York apartments. The second bedroom was connected to the living room through French doors. The building offered a laundry room and a live-in super. The price was $670,000, with annual taxes of about $5,200 and $712 a month in common charges.

Brown Harris Stevens

No. 3

River-View Condo in Hamilton Heights

Katherine Marks for The New York Times

This freshly renovated two-bedroom, one-bath condo with 918 square feet was on the top floor of a 35-unit condo from 1920, a short walk to the subway at 145th Street and to Riverbank State Park. The long, narrow floorplan had a new semi-open kitchen with a peninsula and a built-in cooktop, a windowed bathroom, in-unit laundry, and a walk-in closet in the primary bedroom, which had a window facing west over the Hudson River. The price was $725,000, with annual taxes of about $5,300 plus $980 a month in common charges and a monthly assessment of $295 until December 2025.

REAL New York

Find out what happened next by answering these two questions:

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Two-Balcony Condo in Harlem

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River-View Condo in Hamilton Heights