Growing up, Lorena Waters thought the path to adulthood was college, a rental while saving money in her 20s, then a two-story house with an attached garage. Now 34, Ms. Waters spent a decade saving for a down payment, working multiple jobs throughout her 20s rather than spending weekends at birthday parties or bars before becoming a federal employee. She also lived in a string of attic and basement apartments on Long Island where the rent was cheap, she said. By her mid-30s, it was time to level up.

Ms. Waters began looking for a home to buy in the spring of 2025. What she couldn’t control in her timeline was the housing market she entered, where the so-called starter home has all but disappeared among rising costs and competition. It took her seven tries to finally close on a house.

“First-time home buyers are now often up against all-cash buyers who are more likely to be investors, but they’re also more likely to be baby boomers who could be wanting to downsize or looking for that entry-level property,” said Jessica Lautz, the deputy chief economist at the National Association of Realtors .

In May, all-cash buyers made up 25 percent of purchases and roughly a quarter of homes sold above list price, according to NAR data. The typical seller also received more than two offers, which could include different contingencies like days to closing that could help one offer rise to the top.

Ms. Waters’s wish list included a home in the same school district she attended in Long Island, two floors, a fireplace and a basement. With Andrea Parks, an agent with Douglas Elliman, she searched for homes around $500,000, hoping for more than two bedrooms and at least one and a half bathrooms. Here is the trajectory of her search:

Bid 1: Picture-Perfect Money Pit

A three-bedroom house with a porch swing that charmed Ms. Waters had a deal-breaking crack in the foundation that was found during the inspection.

Listed For: $550,000 in October 2025

The Offer: $565,000, accepted but rescinded

Sold For: $545,000

Ms. Waters said: “I have friends who are in the trades, and one of my friends was like, ‘If you see a house and the foundation’s messed up, just walk away,’ so that was always in the back of my mind.”

Bid 2: Sitcom-Worthy Set Up

A two-floor house with freshly updated interiors was exactly where Ms. Waters wanted to be, and it came with reasonable taxes.

Listed For: $599,990 in October 2025

The Offer: $600,000

Sold For: $625,000

Ms. Waters said: “I wanted a two-floor house, growing up in one. I joke that, growing up watching ‘The Simpsons’ and ‘Married With Children,’ people have a two-floor house with an attached garage.”

Bid 3: The Heartbreak House

A three-bedroom, two-bathroom colonial-style home facing a wooded area and a quick walk to the water was a place Ms. Waters could envision raising her future brood.

Listed For: $559,990 in October 2025

The Offer: $575,000

Sold For: $585,000

Ms. Waters said: “That was the one where I had a lot of regrets. I lost it by $10,000, and I thought maybe I should have done it, and I’m glad I didn’t in the long run.”

Bid 4: The Moneymaker

A reasonably updated three-bedroom home offered the added perk of an income-producing apartment on the premises.

Listed For: $549,990 in October 2025

The Offer: $575,000

Sold For: $610,000

Ms. Waters said: ““It had an apartment but the foundation was really messed up. It was from the early 1900s and that was the issue with a lot of houses in Patchogue, unfortunately.”

Bid 5: Postage-Stamp Stumper

A house on a charming, dead-end block in the right location seemed like a good option for Ms. Waters at first, but she realized it was too small to grow into.

Listed For: $549,999 in November 2025

The Offer: $565,000

Sold For: $575,000

Ms. Waters said: “It did have a porch, which I loved, but it was very unrealistic for the future and it seemed like the sellers were moving out because they just had a baby.”

Bid 6: The Reluctant Rancher

Ms. Waters put in an offer on a ranch-style house with an income-producing apartment despite really wanting two floors as her search grinded on.

Listed For: $599,000 in December 2025

The Offer: $600,000

Sold For: $614,000

Ms. Waters said: “I was getting afraid I was going to have to settle and get a ranch.”

As Ms. Waters’s search dragged on, Ms. Parks recommended she look in the next town over where the competition was less steep. She finally relented when Ms. Parks sent her the listing for a three-bedroom, two-bathroom home across 2,500 square feet, considerably larger than all of the other houses she’d made offers on.

Bid 7: Score!

Ms. Waters loved it because it had a concrete foundation, two floors, a basement, a fireplace and a sun room, exceeding her wish list. She offered $675,000, $55,000 over the asking price, and held her breath.

“My realtor called me, and she goes, ‘Lorena, guess what? … You’ve got a house,’ and I just cried,” Ms. Waters said.

Ms. Parks talks about her client like a proud parent. “Half the job is resilience, and Lorena kept showing up after every ‘no’ that we got,” Ms. Parks said, “and we got quite a few.”