Chelsea Clinton’s Wedding Lit up Rhinebeck, New York—a Decade Later the Small Town’s Housing Market Is White Hot – Mansion Global

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About 100 miles due north of New York City and tucked into the northwest corner of Dutchess County, the historic Hudson River Valley community of Rhinebeck has thrived in recent years as a go-to tourist destination and a haven for city residents looking for a bucolic second, or first, home.

Most locals trace its recent popularity and real estate boom to the 2010 Rhinebeck wedding of Chelsea Clinton at Astor Courts, an estate once owned by millionaire businessman John Jacob Astor IV. It seemed that just about every Bill or Hillary Clinton sighting in the days leading up to the wedding made it into one of the local papers.

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“I remember my mom telling me, ‘Access Hollywood’ is on the corner,’” said Kyle Irwin, a Rhinebeck native and current resident who works full time as a real estate agent with Corcoran Country Living. “From that day forward, people knew where Rhinebeck was. Even if I was in California, people would know Rhinebeck and where it was.”

Norah Burden, an agent with Brown Harris Stevens and a Rhinebeck resident for nearly 30 years, agreed. “I watched it, I was there—it was eight reporters deep in places,” she said. “The international press descended on that tiny town.”

A decade after that wedding, the Covid pandemic hit, and “it was like throwing gas on a fire,” Burden said, as people from New York City flooded Rhinebeck and the rest of the Hudson Valley.

“It felt like a very safe place to be,” she said.


Like many communities in the Hudson Valley and the rest of New York, Rhinebeck is both a town (the larger geographic and political unit) and a village. The 1.6-square-mile village is at the center of the 40-square-mile town. The riverfront hamlet of Rhinecliff is also in the town.

“The village is the hub of all the culture, where the restaurants and boutique shops are,” Irwin said.

The town’s northern border is the boundary with the town of Red Hook, and the towns of Milan and Clinton are on the eastern edge. The Hudson River forms the western boundary, with the town of Hyde Park to the immediate south.

The village’s commercial downtown is fairly small and mostly centered around the intersection of Montgomery and Mill streets, with lots of boutiques, clothing shops, galleries and bars and restaurants. 

Price Range

For the last 12 months, the town of Rhinebeck had a median price of $620,000, Irwin said. 

“There are 18 homes on the market now, with a median price of $916,500. The top price now is $6.875 million,” he said.

Chelsea Clinton’s wedding at Astor Courts helped put Rhinebeck on the map.


At the beginning of the pandemic and pre-pandemic, “for $500,000 to $700,000, you could find something that was pretty solid, that would not need lots of work,” she said. Since then, there’s been “a significant increase.” 

On average, properties are still going above the asking price, which became routine during the pandemic, she said. For the last year, the median list price was $597,500 compared to a median sale price of $618,375.

Inventory is “really tight,” Burden said. “Rhinebeck is highly coveted. People want that Rhinebeck address—it’s a tony address, it’s an address people know about.”

Housing Stock

The style of homes in Rhinebeck are a mix, Irwin said. “We have a lot of historic houses but also split levels and raised ranches and ones built in the 1980s and ’90s. The median year built for the town is 1970.”

“There is a big demand for new construction,” she added.

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There are still a few farmhouse properties, “but lots of them have been broken up over time,” Burden said.

Historic houses in the village get the highest prices and are the most valuable, she said. “The village has exploded in value. That was a Covid thing.”

What Makes It Unique

“Rhinebeck was always home” said Irwin, who was born and raised in the village and came back full time as an adult nearly five years ago. “I always come back. It’s a very special place and no wonder so many people have come to love it.”

“When I was growing up it was a lower-key community,” she said. “You knew absolutely everyone. It was not a destination town and village, like it is today.”

Rhinebeck is home to America’s oldest continuously operated hotel.


“Because of all the changes in Rhinebeck, I’m able to have a vibrant career as well as an interesting social life,” Irwin said.

Burden highlighted the many restaurants, shops and galleries. 

“We’re surrounded by such a historic area of our country, all sited along the Hudson River,” she said. “It’s a close-knit community with New York City amenities.”

It’s also a good home base from which one can explore the Hudson Valley and the Catskills.

Rhinebeck is “beautifully laid out, very compact, very complete,” Burden said. “You can happily remain in town and get your provisions. There is enough retail and at least 15 restaurants, most of them good.”

“People appreciate the historic architecture here,” she said. Among Hudson Valley communities, Rhinebeck is known for its great schools.

Further, it is right by the Kingston-Rhinecliff Bridge over the Hudson, she said. “It takes me 10 to 15 minutes to be in the middle of Kingston.”

Luxury Amenities

“The biggest luxury for me, honestly, is the train, having access to two train lines,” Burden said. “It’s five minutes for me to get to Rhinecliff and the Amtrak station there.” In the other direction, it’s a 20-minute drive to Poughkeepsie and its Metro-North Railroad station.

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Soho House, the members-only international hotel brand, has announced a new location in Rhinebeck. The luxury countryside retreat will reside at Grasmere House, a 250-acre former working farm that’s about a 15-minute drive from the Rhinecliff train station, according to published reports. It will offer several food and beverage options, a wellness facility, a spa and guest bedrooms, with restored 19th-century buildings surrounding a manor house.

For several years, Rhinebeck has had a vibrant restaurant scene.

Irwin’s favorites include Market Street, Le Petit Bistro, Cinnamon Indian Cuisine (“the best Indian food ever”) and Foster’s Coach HouseTavern “because I grew up going to brunch there and you can still get their London Broil,” she said.

Terrapin Restaurant is in a converted church, with a more formal dining room with New American fare on one side and a casual bistro with soaring ceilings on the other.

Samuel’s Sweet Shop offers packaged goodies, candies, chocolate by the pound and novelty items such as chocolate mac ‘n cheese. It is co-owned by Paul Rudd, known for his roles in “Ant-Man” and “Only Murders in the Building,” and “Walking Dead” actor Jeffrey Dean Morgan.

Taconic State Park is close by.

Getty Images

If movies at the mall are not your thing, there’s an old-fashioned nonprofit movie house in Rhinebeck called Upstate Films. Since the 1970s, it’s been showing first-run, indie, foreign and classic movies. Dress warmly in cold weather.

A very popular weekly farmers market is held on Sundays in the village’s municipal parking lot.

For antiques, stop by the Antiques Market behind the Beekman Arms-Delamater Inn.

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“Most residents send their kids to the public schools, which is why many people want to buy in Rhinebeck,” Burden said. Rhinebeck and Red Hook have some of the best schools in the Hudson Valley.

Nearby parks with walking and biking options include Poet’s Walk Park in Red Hook, Drayton Grant Park at Burger Hill on New York 9G in Rhinebeck, Starr Park on Traver Lane in Rhinebeck, Taconic State Park in Copake Falls and Ferncliff Forest on Rutsen Road in Rhinebeck.

Nearby ski resorts include the Catamount Ski Area, which straddles the New York-Massachusetts border, Hunter Mountain Resort in Hunter, New York, and Belleayre Mountain Ski Center in Catskill Park, New York.

Who Lives There

Rhinebeck has a good mix of weekenders and locals, Burden said. “It has a very intact local community. Historically, Rhinebeck has had a super-strong weekender community. That is not new.”

Paul Rudd and Jeffrey Dean Morgan co-own a sweet shop in the town.

Composite: Getty Images

“In the old days you could see someone in the hardware store dressed in wellies and Carhart jeans and not know whether they worked on a big estate or if they were the owner,” she said. Things are fancier now. “We’re already seeing a handful of spas.”

“I’m now seeing an influx of people from the Hamptons and also what I call climate refugees from the West Coast, who are tired of the wildfires,” Burden said. “They are looking for high ground, for a safe space.”

Because of new work-from-home routines, there has been a blurring of weekenders and full-time residents, Irwin said. Now people may just commute into the city two days a week.

Notable Residents

Current and former residents include singer-songwriter Rufus Wainwright, actresses Lorraine Toussaint and Emma Roberts, Paul Rudd, millionaire businessman John Jacob Astor IV, who went down with the Titanic, “Dumb & Dumber” and “There’s Something About Mary” movie producer Charles B. Wessler, and married actors Jeffrey Dean Morgan and Hilarie Burton, according to published reports.


Both Irwin and Burden are optimistic about Rhinebeck’s future. 

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“People are always wondering when they buy whether it’s a good investment,” Irwin said. “I think values will not only hold but increase in coming years.”

The Rhinebeck market is going to remain “super strong,” with the lack of inventory being the biggest challenge, Burden said. 

Like in the city, many homeowners are locked into very low mortgage rates, she said. “There is not a lot of incentive for people to trade up or out.”

Prices will remain high, she said. “That genie is out of the bottle. It’s too finite, too desirable, and not enough to go around and just too beautiful an experience to live in.”

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