When Timothy Harper and his wife finally chose a house, a big selling point was that it sits on a quiet lake that doesn’t allow gas motor boats or jet skis. Photo: Timothy Harper 

Looking at scores of weekend houses over 18 months, this couple learned a lot about second-home real estate – and each other

When my wife and I sold our longtime family home in the suburbs and moved back to Manhattan in 2009, we were looking forward to the empty nest and a return to our pre-kids lifestyle – a rental apartment in the city and a weekend house upstate. 

It seemed like a good time for house hunting in the Hudson Valley. The economy was still mired in the Great Recession, and housing prices had not rebounded. And Nancy and I loved the idea that the Hudson Valley was attracting droves of Brooklyn hipsters, many of them starting families and creative or crafty businesses, from just north of Westchester to just south of Albany, on both sides of the Hudson. 

We had a wish list for a second home – within 90 minutes or so of the city, and a short drive to a Metro North train station. We also wanted to be on or near a lake where I could swim on warm summer days. And we wanted space to put up our two kids and other relatives and friends for a weekend or longer. 

“I bet we find a great place right away,” I said. 


We looked at 117 houses – that is no misprint – over the next year and a half. Once or twice a month, we got up early on Saturday mornings and drove up the racetrack known as the Taconic State Parkway to places with evocative names such as Cold Spring, Pine Plains, Stormville, Wappingers Falls. And, of course, both Fishkill and East Fishkill.

We actually remember a lot of the houses over the months, beginning the Saturday we met the Pawling real estate agent, Claudia Jiskra, we found on the web. From that first day, Claudia was impressed with how quickly we could look at a place and say no. We agreed to return in a couple of weeks for a much longer list of visits. 

I think we might have seen seven houses next time, and up to 15 in ensuing visits.  Claudia, who could look up exactly each of our 117 house visits, where and when, said that 15 was a one-day record for her. She wasn’t sure that day if we would have time to see all 15 houses; she had never shown anybody more than 10 houses in a single day. 

We were done by early afternoon.

Claudia was impressed, and kept us on tight schedules. She liked our flexibility, and at one point called us “motivated buyers.” But nothing motivated us enough to actually make an offer, even though we looked at several houses more than once – which means we probably had 125-130 total house visits.

Almost every place had things that we liked. Or, rather, that I liked. Today we joke that 30 or 40 of those houses would have been fine with me. Fortunately, Nancy has better taste. Looking back, I’m grateful she wasn’t as picky about men as she was about country houses. 

By house No. 50 or 60, we’d walk in, and murmur and nod along with Claudia’s recital about what was good, and what could be done to make the place better. Then, back in the car, I’d turn to Nancy and say, “Uh, what didn’t we like?” 

I tended to be over-optimistic, to see how things might be. She was realistic, recognizing how much time and money would be involved.

She usually had a short, but decisive, list related to things we couldn’t change, or would cost too much to change. She grew up in a family of developers and builders, and had a good eye. She could “see” us in the house better than I could.

Proximity to a good swimming lake was of top importance to the couple. Photo: Timothy Harper 

Some places were too small. A couple were too big. Quite a few were too far from lakes. Or the lakes were not good for swimming – too many power boats and jet skis. She rejected houses with lots of steps, or with steep stairs down to the lake. “Harder when we get older,” she warned. I didn’t see the problem with stairs and hills back then, but now, 13 years later, I do. 

We visited one house three times, the final time with an architect friend who loved the 18th-century character of the place and the expansive gardens, but suggested that even modest renovations would cost almost as much as the property. We liked one new-ish lake house, but the only way to reach it was through a trailer park to an isolated dead end where no one could hear you scream. 

We liked a place on a road called Pumpkin Lane, but it was too far from a lake or a park or a place to buy milk, gas and beer. We liked a little lake house, but the houses were jammed in so close I could reach over the deck railing and flip our neighbors’ burgers. Another little house was on a wonderful lake but, at just over two hours away, we decided after a second visit that it was too far.

We got on Claudia’s bad side when we went off on our own and looked at a house for sale by owner. We visited that house a second time, and liked it enough to bring in an inspector who gave us a generally positive but not glowing report. We offered to rent the house for a year with an option to buy, but the owner didn’t want to get that creative. So we walked.

Claudia had been reluctant to show us any more houses while we were looking at the one that was for sale by owner, but we eventually persuaded her that we were still motivated and still wanted her to get a commission from helping us. I began perusing online listings up and down the Hudson Valley, and sometimes suggesting places I found. Claudia cheerfully booked visits for every place I recommended, except one.

“Hang on,” she said when I phoned her with the address. I could hear her rustling through papers on her desk. 

 “I took you to that house two months ago,” she finally said. “We pulled up in front and you wouldn’t get out of the car.”

The couple’s first glance of their future home. Photo: Timothy Harper

Going into our second year of looking, Nancy and I were running out of enthusiasm. Maybe we couldn’t be as close to the city as we had hoped. Maybe we couldn’t get a lake house. We thought about giving up for a while. Then I saw a new listing for a little cottage on the same lake where several months earlier we had seen a stone house that was really nice – except for being too small, with no chance for expansion because of thick interior stone walls.

Claudia arranged a viewing at the new listing a couple of days later. At the cottage, we walked in and I started my usual mumbling about this was good and that was good. Nancy didn’t say anything. I could tell she was not impressed with the layout; the house was not far from the lake, but there were no direct views of the water from the kitchen, dining room or living room. The kitchen was a galley the size of a closet, like something you might find in a junior one-bedroom in Manhattan.

I could tell there was a lot she didn’t like. Outside, standing on the gentle slope down to the lake — a mile long, a few hundred yards wide, no motorboats, with a picturesque sand beach directly across from us – Nancy turned to me when Claudia was out of earshot.

“Let’s make an offer,” she said. “This place isn’t perfect, but everything we can’t change is good – it’s an hour from the city, the lake is good for swimming, we can change the floor plan. We can change all that.”

Forty seconds later, I gave Claudia a number well below the asking price. She seemed shocked.

“Really?” she said. “Just like that, an offer? Your first offer?”

She paused, looked skyward and laughed. 

“If it ever happened, I was expecting angels and trumpets or something,” she said.

The house in winter, as viewed from the lake. Photo: Timothy Harper 

It turned out the sellers were motivated, too. They countered with a number halfway between our offer and their asking price. We said yes, and closed six weeks later, in May 2010. We drove from the closing to buy cleaning supplies, then went to the house. I put down the Lysol and new broom,  pulled on my swimsuit and swam 350 yards over to the little beach and back.

Over the next couple years, we acquired a canoe, kayak, sailboat and rowboat. We made notes and plans about changes we could make, then renovated to give us good views of the lake from the new, open dining and kitchen areas. 

That 117th  house has been better than even an optimist like me could imagine. We have had many epic weekends with our friends and relatives, and with our kids and their friends. We have swum, paddled and sailed thousands of hours and miles on the lake. The house became our refuge in the first months of the pandemic, as we made proper dinners together and then read or watched movies in front of the fireplace.

More than once – maybe more than 117 times – I have told Nancy how grateful I am for her patience and persistence. I have also congratulated myself, silently, on listening to her and trusting her judgment.

Out of curiosity, I sent a note to Claudia Jiskra the other day at her office in Pawling. 

“Hey Claudia,” I texted. “It’s Tim Harper (2009-10), 117 houses.” Did she remember us?

Oh yeah, she remembered us.

“We searched high and low.” she recalled. “You are still my record. My second highest number – 87 – was mad he couldn’t break your record.”

Does your escape home have a back story? Let us know. We’d love to hear it. Email us at hello@theescapehome.com

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