Apartments that got away, surprise bed bugs, and more: New Yorkers share their greatest real estate regrets

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Real estate regrets? We've all had a few. Even the best-prepared buyer, renter, or seller in this market is bound to have a story about ill-advised roommates, landlord red flags, or apartments in up-and-coming neighborhoods that they should have snapped up when the getting was still good. Because misery loves company—and because we can all learn something from each others' missteps—we talked to New Yorkers about their biggest real estate-related regrets:


"In 1994, I passed on an adorable one-bedroom apartment in a brownstone/townhouse on West 74th between Central Park West and Columbus for $100,000. It was small but pristine, and adorable with French doors separating the living room and bedroom and a fireplace. I can only imagine what it would be worth today." —Jen, East Village

"Nixing the purchase of a building in Tribeca with my ex-husband." —Marylou, Manhattan

"My regret is actually a regret of my parents that I and my future grandchildren will live to regret! In the 1970s, my parents passed up on an opportunity to buy a building with nine rental units on Riverside Drive around 90th street for $100K! They said at the time $100K was a lot of money for them. But if they could go back, they would beg, borrow, and steal to get the money to buy that building." —Julie, Battery Park City

"In 1997, I decided not to buy a studio in Tudor City—at what was then considered the peak of the market—for $75,000. And because of everyone's warnings about 'how high' the prices were, not going for the one-bedroom in the West Village...for $120,000." —Constantine, Lower East Side

"Buying too small instead of stretching our budget—our family outgrew our apartment within two years, and the market had completely outpaced us in that stretch of time." —Anonymous, Morningside Heights

"Over my first six years in real estate I was keen to find a 'perfect' home and searched far and wide. Thanks to one of Brooklyn's premiere agents—Jim Cornell—I was turned onto 1 Knickerbocker Avenue in Bushwick and fell in love. I imagined a venue downstairs (I am an event programmer and a creative so having space for pop up parties or gallery was important), and the upstairs was my perfect home (despite being zoned commercial!). I bid, I crafted, I cajoled and, most of all, I knew the appreciation which was imminent in the neighborhood. Sadly, we couldn't make a deal (we stalled out about $50,000 apart) and recently the building was flipped for $3 million! I've always wished I was able to buy what I felt was my perfect home." —Sydney Blumstein, Corcoran Broker

"Not buying a Chelsea building in 1985 for $63,000...for obvious reasons." —Doreen, Manhattan


"While I don’t regret buying an apartment when I did—it was a buyer’s market and the interest rates were very low—I do regret buying where I did. The neighborhood is more isolating than I thought it would be. I should have really spent more time walking around the neighborhood to understand the quality of services and amenities and not be so charmed by an initial positive impression. I lived in Astoria before moving back into Manhattan, and part of me thrilled at having a Manhattan address again. But in reality, I loved living in Queens, and I regret not looking harder there, or being willing to take a risk farther out to find a larger and affordable place in a neighborhood I’d actually enjoy." —Lana, Washington Heights


"My first apartment in Brooklyn. I was so desperate to live in Park Slope, I settled for a tiny space in a rundown three-bedroom apartment. My room, which didn't even have enough space for a closet, looked out onto the building's trash-filled courtyard. You couldn't even sit on the living room couch because springs were bursting out of it. When my mom saw it for the first time, she cried." —Emily, Bed-Stuy


"I regret not having lived at home (in the city) for a few years after college. I lived there for about four months, but to think of the money, I could have saved! Of course, at the time, I wanted to be on my own and wanted a chance to live in the East Village, which was cooler than the Upper West Side, but still. I kick myself when I think I could have saved thousands of dollars." —Lucy, Upper East Side


"After Hurricane Sandy, I rented a room from a friend-of-a-friend in a 'luxury' conversion on the UWS. The building's shady management company knew there was a bedbug problem, but was selectively treating it because the bedbugs were being used as a way to evict the rent-stabilized tenants they had inherited when they had purchased the building." —Constantine, Lower East Side

"If you can believe it, I actually don’t have any in New York (#blessed). But once when I lived in Hilton Head, our landlady went radio silent after we moved out and we had to take her to court to get our security deposit back. We eventually found out, many months later, she had gone bankrupt and not told us. So we therefore lost both our security deposit and court fees." —Tim, Brooklyn


"Not getting off the lease when I left an apartment early. My roommate (and former friend) ceased paying rent as soon as I left, leaving us both on the hook for thousands." —Anonymous, Bushwick

"Not trying to find a tenant when I broke my lease. I thought the landlord would find someone quickly, but it sat vacant for eight months and the landlord came after me for every penny. I later learned that in New York landlords have no obligation to even try to re-rent an empty apartment." —Anonymous, Upper West Side