The 1925 house seemed to need just the right amount of work. “It was not hazardous, but plaster walls were falling apart and needed to be patched,” Mr. Rhodes said. The stains and smells of once-resident pets had soaked through the carpeting and were visible on the floors.
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Jesse Neider for The New York Times
The house did not seem to need exterior work, like roofing or siding. The asking price was $400,000.
Mr. Rhodes returned with Sue Okie, a friend’s mother, who is a sales associate at the Darien office of Halstead Connecticut. Because of the house’s condition, he offered $330,000.
The counteroffer was $395,000. No deal.
Mr. Rhodes checked out an 1840 house on Silvermine Avenue, marked with a plaque. The price of the three-bedroom had dropped to $330,000 from $400,000.
Mr. Rhodes was concerned about the house’s age. “It felt like you could open up a wall and find compounding issues,” he said. “So where it was maybe a little less on the budget at first, I was concerned it would be much more on the budget in the long run.” The house sold for $300,000.
Another option was a 1959 bank-owned four-bedroom house on Old Belden Hill Road.
The exterior was rundown, and he was reluctant “to be diving into that type of a project,” he said. The yard, though large, was overgrown with vines and brush. Its slope made it unsuitable for a picnic table, he said.
The house sold for $347,000 to Dan Raposo, a Realtor at the Higgins Group, a realty, and an investor in RPM Homes, which buys and flips single-family homes.
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Jesse Neider for The New York Times
“To me, this was a moderate rehab,” Mr. Raposo said. “An extensive renovation is stripping everything down to the studs and doing everything all over again.”
The roof was replaced and the siding repaired. “We took out two Dumpsters of just yard debris,” he said.
The house, now in move-in condition, Mr. Raposo said, is on the market for $499,000.
Meanwhile, the house near the harbor kept drawing Mr. Rhodes back. “There was a lot of upside potential,” he said. “The amount of work was in the realm of my capabilities.”
He liked the area. “You can walk the dog and say hello to the neighbors,” he said. “It was the best choice out of what I’d seen.”
A few weeks later, Mr. Rhodes offered $365,000. Another offer had just been received. So he raised his offer to $390,000, which was accepted.
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Jesse Neider for The New York Times
The inspection found pipes that needed replacing, and “some areas of concern that weren’t issues yet, like keep-your-eye-on-them scenarios,” Mr. Rhodes said. He also had a septic inspection. “Thankfully I did, because it was barely in working order, so the sellers replaced the whole septic system,” he said.
Mr. Rhodes closed last winter and since then has been fixing, patching, painting and cleaning, with the help of Ms. Walsh and others. “He always loved a project and is constantly tinkering with things,” Ms. Walsh said.
Contractors did plumbing and electrical work, refinished the floors and installed a new kitchen. Critiques? The garage is better suited to storage than a car. Ms. Walsh would have preferred a second full bathroom to the half-bath they now have.
“I don’t know if I was fully prepared for the effort I put forth,” Mr. Rhodes said. “I had to figure out how to hang a shower curtain on an angled ceiling. But I am extremely pleased with the results.”
He sacrificed a big yard in favor of proximity to the water. “It is certainly a fair trade-off in my book,” he said. The house has second-floor water views in the winter.
Lars, a miniature schnauzer, is adapting to his new space. “He is trying to figure out where he can sleep and where his little pet beds are,” Mr. Rhodes said. “It’s a new lifestyle for him in that regard.”
