New York City Elites Look North to ‘Old World’ Luxury of Hudson Valley’s Sprawling Estates

New York City's wealthy set is looking to a lesser-known section of the Hudson Valley for more acreage, more house, and more bang for the buck.

The Realtor.com® economic research team's latest luxury markets report highlights a corridor of estate-driven communities across Dutchess County and Orange County in the metro of Kiryas Joel-Poughkeepsie-Newburgh, NY, where the top 10% of listings start at $1,295,000.

The share of listings priced $1 million or higher in this area west of the Hudson River is 14.3%. The area's total count of such listings is up 6.7% from a year ago, the eighth-biggest increase in the nation.

While the rolling farmlands of Amenia and Pine Plains and the historic estates of Tuxedo Park carry the old-world feel of an English manor or a Tuscan village, they are only a 70-minute commute to the glittering skyscrapers of New York City.

"People don't know Tuxedo Park," Tinka Shaw of Tuxedo Park Fine Homes Team at Compass tells Realtor.com of the private gated community. "Prices have gone up a little since 2020, but nothing like Westchester or Connecticut."

With a median listing price of $1.2 million, Tuxedo Park and nearby Millbrook offer softer entry points than nearby Pine Plains, with its hefty median of $2,372,500.

"It's instant community," says Shaw, a local who bought a home built in 1886. "We're not surrounded by restaurants. So instead, people have dinner parties. In the city, you go to a restaurant and leave. Here, 70-year-olds will have 30-year-olds over for dinner."

Originally founded in the 1880s by tobacco heir Pierre J. Lorillard IV and fabulously wealthy hotelier William Waldorf Astor, with many of the homes designed by Gilded Age architect Bruce Price (whose daughter is famed etiquette writer Emily Post), Tuxedo Park retains its historic grandeur.

The village's current most expensive listing, dubbed Renamor, is a $27.5 million estate with 19 bedrooms and 151 rolling green acres. Blending history, luxury, and sustainability, this 1928 French Provincial estate comes with guest and carriage houses, as well as a boathouse on Tuxedo Lake. It is also powered off-grid by solar and geothermal energy.

Over the years, notable Tuxedo Park residents have included actress and "The View" host Whoopi Goldberg, "Spin City" actor Barry Bostwick, singer Cyndi Lauper, and Broadway star Sutton Foster, whose historic dwelling was designed by Price himself.

While you have to hop in your car to reach most anything—"it's not a walkable community," Shaw admits—amenities include round-the-clock security at its two entrances, plenty of hiking trails abutting Harriman State Park, two lakes, and two private clubs: The Tuxedo Club, with upscale facilities for golf, racquetball, padel, tennis, and lake sports and fishing, and the accessible municipal club Wee Wah Park & Beach Club, with swimming and a brand-new kids' playground.

Across the metro, new construction accounts for only 12.9% of luxury listings, consistent with a market where the appeal is more rooted in existing structures and established land than in new development, says the report.

A newly constructed masterplanned community from Lennar, Tuxedo Reserve, offers single-family homes starting at around $700,000. The community sits on the Metro-North commuter railroad Port Jervis line with direct access to New Jersey and transfers to Penn Station, and is only 2.5 miles away from historic Tuxedo Park.

Who is moving to Tuxedo Park

Unsurprisingly, most new residents are city dwellers seeking more land, more house, and more community.

"We have a huge influx of people coming from Brooklyn," Elizabeth Broderick of Tuxedo Hudson Realty tells Realtor.com. She notes many hail from the family-friendly, brownstone-lined neighborhood of Park Slope, with its median price tag of $1.6 million.

She says the "biggest surprise," however, is the migration from Bergen County, NJ, only 20 minutes away. Many home shoppers are retirees, but instead of downsizing to smaller homes, they want sprawling homes big enough for all the adult children and many grandchildren.

For younger families, a significant draw to the town is its well-regarded private school, Tuxedo Park School.

"They come here specifically for the school," says Broderick.

She notes many of her clients, while hunting for a weekend abode, swiftly fall in love with the town's historic character, generous parcels of land, and welcoming neighbors. Soon, they switch their search from vacation home to a forever home.

"You drive through those gates, and it's so stunning," she says. "It's the Hudson Valley feeling, but it's Old World, too."