Life beyond Brooklyn: A guide to buying a house in the Hudson Valley


So you’re dreaming of a house in the country. Your apartment walls are closing in, and you need somewhere to go on the weekends. The pandemic has already sent a huge exodus of city folks to the Hudson Valley and Catskills, but are there still housing deals to be had? How much money do you need to make your country home dreams come true?

My husband and I took the super budget-conscious route 5 years ago, when we bought a trailer as a country bunker and plopped it on the land my grandfather bought when I was a baby. You can read about it on my blog, Brooklyn DoubleWide, but when you see the putty-colored vinyl walls in our bathrooms, you may not want any home-buying advice from me! So, I talked to real estate brokers and a Catskills-based “realtor matchmaker” and they had a whole lot of great tips and advice to share.

The range in home prices upstate depends on so many things: Amenities, views, proximity to NYC, a desirable town. This luxury farmhouse in Rhinebeck listed with Gary DiMauro Real Estate recently sold for over $600,000 the asking price of $2.5 million. Photo: Gary DiMauro Real Estate

Name your non-negotiables

Do you need a pool? No visible neighbors? Do you want to ski nearby? Ask yourself what really matters to you before you start your search. “The town may not matter at all if a family just wants to relax in nature and hang out at home,” says upstate consultant and realtor matchmaker Maggie O’Neill of City2Upstate, who splits her time between Brooklyn and Woodstock. “Some families may want to be very remote and have very little interest in exploring restaurants, bars, or music scenes. In this case, the most important factor on location may be cost or proximity to grocery store.” O’Neill doesn’t show houses, but she’s happy to give advice and set you up with a realtor specifically geared toward your home-buying needs. (Consulting with her is free, and if you end up buying a house, she’ll get a cut of the realtor’s fee.)

According to David King, a broker for Gary DiMauro Real Estate who moved to the Hudson Valley in 2003 after spending 25 years in the East Village, there is only one thing to consider when choosing a town: “Vibe. V. I. B. E. I take people across the Rip Van Winkle Bridge to Catskill, and either they find it authentic and they respond to it, or they can’t wait to get out of there.” King emphasizes the importance of getting a map and driving from town to town to see which places resonate with you.

Anecdotally, inventory is low upstate because many upstate homeowners have held on to their homes either for their children to use during the pandemic, or because they’ve turned it into their primary residence. This 2-bedroom close to Woodstock sold for $30,000 over its asking price of $589,000. Photo: Coldwell Banker Village Green-Woodstock/Upstate Abodes

Reality check: Be prepared for a challenging search

Keep in mind that the market is tough right now. “As of September in Ulster County, closed sales are up 40% over last year, housing prices are up 18.9% and inventory is down 28%. The market is very competitive,” said Leslie Foti, the Catskills realtor behind @upstate_abodes. Prices are so high, many upstate towns and cities are considering regulations on Airbnb properties, which are also contributing to the lower inventory and spike in housing costs—something to consider if you were fantasizing about becoming a “superhost.”

King also noted that many baby boomers who had been planning to sell their homes instead decided to pass their houses to kids or grandkids who needed more space once COVID hit. “Things that would’ve normally come on the market didn’t come on the market,” King said. “We’re absolutely in a seller’s market. Going into the pandemic before the ides of March, inventory was already low. The pandemic was the perfect storm.”

Libby McKee, who sells homes in Columbia County and Northern Dutchess through Berkshire Hathaway HomeServices Blake, Realtors, sees proximity as a culprit in the buying frenzy. Many existing second homeowners who bought close to the city so they could easily commute have made their country homes their primary residence in the pandemic. And now more New Yorkers are looking to do the same. “A majority of my clients are from Brooklyn, and what they’re looking for is a second home that’s not more than 2 hours from New York City,” she says—along with a good wifi connection so they can work remotely. Because of the proximity of this area, we have been swamped. Already this year I have doubled the volume of real estate sales over last year.”

Add to this mix record-low interest rates, and you have a recipe for bidding wars. 

If your budget is $500,000 or less you’ll want to look west of the Hudson River, says David King of Gary DiMauro Real Estate. But that’s not always the case. This 2-bedroom, updated 1890 colonial in Ancram is listed for $249,000. Photo: Berkshire Hathaway HomeServices Blake, Realtors.

Where to look

If you’re specifically looking for a town where you’ll be surrounded by NYC ex-pats and second-home folk, Foti pointed to Woodstock and Saugerties in Ulster County, Livingston Manor in Sullivan County, and Rhinebeck, Millbrook, and Red Hook in Dutchess Country.

McKee’s list of popular places on the east side of the Hudson River includes Millerton, Hudson, Copake, and Hillsdale. But she notes that the under-the-radar town of Pine Plains offers the same kinds of amenities like shopping and restaurants, often for less than these more desirable towns. 

And if you’re looking for a real deal? “The more affordable counties are Delaware (directly north of Ulster) and Greene Counties (located northeast of Ulster),” O’Neill said. “The taxes will be a fraction of what they would be in Ulster, and the housing/property costs will be vastly less. You will end up getting a lot more bang for your buck in either of these two counties. The only downside is that they’re geographically a bit further from NYC and perhaps not as populated.”

Foti did have a couple of recommendations for those looking at Ulster County: “Kingston is still affordable, though home prices have had a significant increase over last year.” (In fact, a report this summer singled it out as having the fastest-growing home prices in America.) “It is a wonderful city with history, diversity, restaurants, vintage stores, and an art scene. Buyers are gravitating to Kingston because it has both a small town and a city feeling. Ellenville and [the] vicinity is also a good value.”

David King’s agency, Gary DiMauro Real Estate, is known for design—not deals. They’re a boutique agency specializing in the most fabulous homes of the Catskills and Hudson Valley. “Basically, if you’re under $500,000 you should be looking on the west side of the river,” said King. “And the farther south you go, the more money you need.” But if you’re looking for a house with good bones on a modest budget, he suggested checking out the village of Catskill and the river town of New Baltimore, both in Greene County.

This home on nearly 2 acres near Woodstock is $695,000, the upper range for a 2-bedroom in a prime location, according to Leslie Foti of Upstate Abodes. Photo: Berkshire Hathaway HomeServices Hudson Valley Properties

Move-in condition versus fixer-uppers

What’s the going rate for a 2-bedroom house in move-in condition in a prime upstate town versus an up-and-coming town? This is a tough call, but Leslie Foti weighed in on the numbers: “Pricing is different upstate, since our inventory is more unique. We have cabins, mid-century moderns, farmhouse styles, different lot sizes, garages, pools/hot tubs, and privacy/views that all need to be considered. A 2-bedroom in a prime area could go for $400,000-700,000 and in an up-and-coming town, it could be $200,000-400,000, but there are so many factors to consider.”

In Columbia County and Northern Dutchess, McKee sees an even wider range. You might find an excellent bungalow for $225,000, but a 2-bedroom on a mountain with panoramic views could fetch millions of dollars. A quick Trulia search shows that pretty much the same spectrum applies to 3- or more bedroom homes.

Let’s say your budget is low and you’re looking at a fixer-upper. Whatever you save on the front end, be prepared to pay for in terms of time given the high demand for contractors at the moment. Foti said, “Everything is in short supply right now, from service professionals to contractors–even wood and materials. I have clients waiting 3-4 months for a contractor to begin working.” McKee extended the average wait for a contractor to begin renovations to six months.

The general consensus is that if you’re looking for a house you can use immediately, you need to find something livable. We spoke to an upstate architect off the record, and he said that contractors are taking jobs from the highest bidders, making it really tough to quote prices on construction right now. Plus, if you find an upstate contractor with much lower rates than a city contractor, you’re probably dealing with someone who doesn’t have experience with the finishes you want.

If you’re able to look at homes early in the week, you’ll have an advantage over those who arrive on the weekend. (You could even make a getaway out of it.) Photo: @theherwoodinn

To buy or not to buy sight unseen

Stories of bidding wars and people buying homes off of Instagram abound. One realtor suggested to my home-seeking friends from Queens that in the current market, they need to prepared to make an offer prior to visiting a home, but the realtors I spoke to thought that was a bad idea. Foti said, “I always recommend viewing the houses in person, if possible. That being said, I have several clients that live afar. I utilize virtual tours, FaceTime and other unique resources to help guide them in selecting a home.”

O’Neill emphasized the importance of seeing a home in person—and making yourself available to see homes the moment they come on the market: “Your ability to be able to come upstate and see a home in person quickly after a home is listed is very important to you actually being able to purchase a home. Especially with homes that are move-in ready, they are selling very quickly. Sometimes the buyer that can get upstate on a Thursday, two days after a home is listed, is going to have an advantage over potential buyers who cannot come upstate until the weekend.”

The satellite dish on this $2.6 million luxury estate in Hillsdale could be a sign of subpar wifi. Maggie O’Neill suggests calling Spectrum to find out if your home is wired for their cable services. Photo: @pkbelfor

Check the Wifi

One thing that many NYC-based home-buyers take for granted is high-speed internet access. Our road in East Durham, NY was bypassed by the only fiber optic cable that runs through town. Our friends in Palenville are just a couple of telephone poles away from their internet line, and the internet provider isn’t in a rush to hook them up. When you don’t have broadband access, you’ve got to use a satellite dish, but the dish needs to be reflecting the signal off another dish, and all of this is very difficult when you live in a mountainous, heavily wooded area. In short, we use wireless hotspots to work/stream/live upstate, and generally use up all our “unlimited” data in a long weekend. It’s far from ideal.

Maggie O’Neill has some tips for confirming high-speed internet at a potential new home: “Asking the owners/seller’s broker to confirm is the best first step, but be specific, and ask what actual company are the current owners using. If the sellers are using Direct TV or Webjogger or Hughes Net, those are all satellite-based internet/cable providers. The quality of the connect, your ability to stream (when we had Hughes Net we couldn’t stream at all), the fact that you’ll have to pay for a data plan, etc. are all really important—especially during Covid-times when so many of us are working from home. Spectrum (formerly known as Time Warner) is becoming more and more available in the Hudson Valley. To be certain, I would call Spectrum before placing an offer on a home to make sure that the address is either wired—or can be wired—for their cable services.”

Other things to consider

Going beyond internet access, Foti weighed in on the importance of an inspection once an accepted offer is in place: “The inspection will provide general knowledge of the house and reveal the positive and negatives. Most homes have a well and septic, both systems should have full testing done… I recommend doing a radon test too. Ultimately, don’t skimp on the inspection; it is a critical step in the home buying process.”

McKee advises homeowners to factor in the cost of a generator too, which can range from $8,000 to $15,000 depending on how much of the home you want it to power. The electricity doesn’t go out often, but in a snowstorm, you’ll want to be able to heat your house.

Even if you don’t plan to become actively involved in your new community, it’s important to spend time in a town to make sure it’s a fit for you. Photo: @sunshinecolony

Seek out locals

Should you be also thinking about political demographics? Is it problematic for a Brooklyn liberal to live in a Trump-leaning town? “Getting a good vibe from not only the town, but also your immediate neighbors and neighborhood, is really important. But, you can—and should—always look up a town’s district state rep and council/assembly people to determine the general political make-up of an area.” O’Neill said. “If it is important to you to get to know and become part of your community, the best thing you can do is spend an afternoon in a few towns to get a sense for how they feel. For those of us with kids, hanging at the local school playground can help you become acquainted with a town as well.”

Speaking of kids, realtors can’t advise on the quality of local schools, but they can direct potential buyers to to do their own research. If you’ve already settled on a town, your best bet is to talk with local parents or schedule a tour of the nearest local schools. When I was recently chatting with one of my blog readers about her decision to send her kids to a Montessori school, she mentioned that she has had some scary racist moments since moving upstate with her mixed-race children and felt safer sending them to a private school with like-minded families. For families who want to find a private school first and build their home search from there, some schools to put on your radar are the Hudson Valley Sudbury School, the Woodstock Day School, and the many Montessori schools in Kingston, New Paltz, Catskill, and beyond.

There is so much to consider beyond the basics of budget and location, but the best you can do is name what matters most to you, and start your search there. O’Neill says, “Generally speaking, while it seems like an overwhelming endeavor, it can and should be fun, too. If having a home upstate is truly a goal, the best way to make it happen is to be slightly flexible until you see a few homes, because that always helps to narrow things down, and to be patient, as it may not happen quickly, especially in a tough market. But the more places you see, the more easily and quickly you’ll know when you’ve found the ‘right one.'”

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