I went inside million-dollar homes on Aspen's 'Billionaire Mountain,' a residential enclave for the ultra rich

Monica HumphriesDec 30, 2021, 02:08 IST

The author drove along Red Mountain Road, which is home to some of Aspen's wealthiest residents.Monica Humphries/Insider

Red Mountain in Aspen, Colorado, is home to some of the ski town's most sought-after real estate.
The neighborhood attracts so many ultra-rich residents that it's been dubbed "Billionaire Mountain."

When it comes to ski town real estate, Aspen, Colorado, is as expensive as it gets. It has the highest asking price per square foot in the US at $2,378 a square foot, according to a 2020 Savills report.

Skiers walking up to Aspen Mountain in Aspen, Colorado.Monica Humphries/Insider

When it comes to ski town real estate, Aspen, Colorado, is as expensive as it gets. It has the highest asking price per square foot in the US at $2,378 a square foot, according to a 2020 Savills report.

And the region is only getting richer. The average home sold for $11.4 million in 2020 — up from $6.4 million in 2019, according to Aspen Daily News.

Two homes overlooking Aspen, Colorado.Monica Humphries/Insider

One of the hottest places to buy property in Aspen is on Red Mountain, a neighborhood overlooking downtown Aspen.

Red Mountain in Aspen, Colorado.Monica Humphries/Insider

The neighborhood attracts so many ultra-wealthy residents that it's earned the nickname, "Billionaire Mountain."

A street sign on Red Mountain Road.Monica Humphries/Insider

Some of the world's richest families own property on Red Mountain, from Walmart heiress Ann Walton to the Bezos family.

Walmart heiress Ann Walton Kroenke, left; Jeff Bezos, right.IAN WALTON/Reuters/Katherine Taylor/Reuters

I drove up the mountain to see what prime real estate looks like in the country's richest ski town. I also got a sneak peek into some of Aspen's most exclusive properties currently on the market.

The author in front of a Red Mountain Road street sign.Monica Humphries/Insider

I drove up the mountain to see what prime real estate looks like in the country's richest ski town. I also got a sneak peek into some of Aspen's most exclusive properties currently on the market.

The base of Red Mountain is less than a five-minute drive from Aspen's main street.

Holiday lights in Aspen, Colorado.Monica Humphries/Insider

At the bottom of Red Mountain is Willoughby Way, which Compass real estate agents Heidi Houston and Doug Leibinger told Insider is considered the most sought-after street in all of Aspen.

A street sign on Willoughby Way.Monica Humphries/Insider

At the bottom of Red Mountain is Willoughby Way, which Compass real estate agents Heidi Houston and Doug Leibinger told Insider is considered the most sought-after street in all of Aspen.

"Most people would tell you they think it's the Rodeo Drive, it's the Park Avenue, it's THE address in Aspen," Leibinger told me. "It's a pretty coveted address and location."

The entrance to Willoughby Way.Monica Humphries/Insider

"Most people would tell you they think it's the Rodeo Drive, it's the Park Avenue, it's THE address in Aspen," Leibinger told me. "It's a pretty coveted address and location."

"I would suspect that almost every homeowner on this street has two to five properties around the world," Leibinger said. "Most of the people that are here, they've also got a house in the Hamptons. They've also got something in Miami, in St. Barts, in Montecito."

A home on Willoughby Way.Monica Humphries/Insider

"I would suspect that almost every homeowner on this street has two to five properties around the world," Leibinger said. "Most of the people that are here, they've also got a house in the Hamptons. They've also got something in Miami, in St. Barts, in Montecito."

Leibinger explained that although the homes higher on Red Mountain are sometimes bigger and more expensive, Willoughby Way has a unique set of factors that appeal to potential buyers.

The last home on Willoughby Way.Monica Humphries/Insider

Leibinger explained that although the homes higher on Red Mountain are sometimes bigger and more expensive, Willoughby Way has a unique set of factors that appeal to potential buyers.

Namely, the street is within walking distance to the center of Aspen and still has breathtaking views of the mountains.

The view of Aspen Mountain from Willoughby Way.Monica Humphries/Insider

Currently, there's only one home on the road for sale — 287 Willoughby Way. And Leibinger predicts it won't be on the market for long.

The only home currently for sale on Willoughby Way in Aspen, Colorado.Monica Humphries/Insider

I toured the five-bedroom, 6,130-square-foot home, which is currently listed at $27 million.

The view from 287 Willoughby Way in Aspen, Colorado.Monica Humphries/Insider

Inside, it's filled with warm woods, floor-to-ceiling windows with mountain views, and a stunning fireplace — all elements I expected in a ski-town mansion.

The interior of 287 Willoughby Way.Monica Humphries/Insider

After touring the $27-million home, I explored the rest of the street. While 287 Willoughby Way was what I expected from a rich ski town, other homes on the road embraced a myriad of styles and designs.

A home on Willoughby Way.Monica Humphries/Insider

After touring the $27-million home, I explored the rest of the street. While 287 Willoughby Way was what I expected from a rich ski town, other homes on the road embraced a myriad of styles and designs.

Some homes were visible from the road, but most had private gates and towering trees for added privacy.

Many homes on Red Mountain have privacy gates.Monica Humphries/Insider

I also passed a $72.5-million home — Aspen's largest sale in history. In June, Patrick Dovigi, a former professional hockey player and the founder and CEO of the waste management company Green for Life Environmental, purchased the nine-bedroom, 21,477-square-foot home.

The exterior of 419 Willoughby Way.Google Maps

I also passed a $72.5-million home — Aspen's largest sale in history. In June, Patrick Dovigi, a former professional hockey player and the founder and CEO of the waste management company Green for Life Environmental, purchased the nine-bedroom, 21,477-square-foot home.

Willoughby Way ends in a cul-de-sac, and as I drove back toward Red Mountain Road, I soaked in views of Aspen and the curving trails from the ski slopes.

The view from Willoughby Way.Monica Humphries/Insider

Then, I hung a left and started crawling up the mountain.

The road zigzags up the side of the mountain.Monica Humphries/Insider

From here, the homes were tucked into the mountain and farther apart. Private drives jutted into forests, preventing any glimpse of the million-dollar homes.

A private driveway on Red Mountain Road.Monica Humphries/Insider

Down many of those roads were homes reported to belong to billionaires like candy mogul William Wrigley Jr. and casino magnate Neil Bluhm.

The view of Red Mountain from Aspen's Police Department building.Monica Humphries/Insider

One of the most popular names associated with "Billionaire Mountain" is Bezos. Bezos' parents Miguel and Jackie have a home on Red Mountain valued at $20 million in 2012, according to Forbes.

Jeff Bezos, left; Miguel and Jackie Bezos, right.Evan Agostini/Invision/AP/Gonzalo Marroquin/Patrick McMullan/Getty Images

One of the most popular names associated with "Billionaire Mountain" is Bezos. Bezos' parents Miguel and Jackie have a home on Red Mountain valued at $20 million in 2012, according to Forbes.

Michael Dell of Dell Computers also has parents with a $10.5-million home in the neighborhood, according to Forbes.

Michael Dell at the Economic Club of New York.David Dee Delgado/Getty Images

While I didn't spot Bezos or any other billionaire, I did receive access to a private drive leading to one of Red Mountain's most lavish mansions.

A private road leading up to The Peak House Estate.Monica Humphries/Insider

Houston took me to The Peak House Estate, the highest residence on Red Mountain. It also happens to be one of the most expensive homes currently for sale in Aspen with a listing price of $44.5 million.

An exterior shot of The Peak House Estate.Hart Houston/Compass

Houston took me to The Peak House Estate, the highest residence on Red Mountain. It also happens to be one of the most expensive homes currently for sale in Aspen with a listing price of $44.5 million.

Filled with history and European design, it's a seven-bedroom, 22,000-square-foot mansion.

The interior of The Peak House Estate.Hart Houston/Compass

From its indoor pool to the 12-car garage, the home oozed opulent luxury.

The Peak House Estate's indoor pool.Hart Houston/Compass

As we left, Houston casually rattled off the names of other billionaires living on Red Mountain.

A view of three homes in the upper section of Red Mountain.Monica Humphries/Insider

She pointed to a plot of land, and told me that tucked behind the growth was a mansion belonging to Leslie Wexner, the founder of L Brands, the company that owns brands like Victoria's Secret, Abercrombie & Fitch, and Express, Inc.

Not viewable from the road, Houston said Leslie Lexner has property on Red Mountain.Monica Humphries

She pointed to a plot of land, and told me that tucked behind the growth was a mansion belonging to Leslie Wexner, the founder of L Brands, the company that owns brands like Victoria's Secret, Abercrombie & Fitch, and Express, Inc.

There's also media mogul Byron Allen, who purchased a 9,000-square-foot contemporary mansion for $27 million in 2020.

Byron Allen's $27 million home on Willoughby Way.Monica Humphries/Insider

The list goes on and on. And after receiving just a glimpse of the properties on Red Mountain, it's clear how the neighborhood earned its well-deserved nickname of "Billionaire Mountain."

Red Mountain in Aspen, Colorado.Monica Humphries/Insider

The list goes on and on. And after receiving just a glimpse of the properties on Red Mountain, it's clear how the neighborhood earned its well-deserved nickname of "Billionaire Mountain."

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I went inside million-dollar homes on Aspen's 'Billionaire Mountain,' a residential enclave for the ultra rich

When it comes to ski town real estate, Aspen, Colorado, is as expensive as it gets. It has the highest asking price per square foot in the US at $2,378 a square foot, according to a 2020 Savills report.

And the region is only getting richer. The average home sold for $11.4 million in 2020 — up from $6.4 million in 2019, according to Aspen Daily News.

One of the hottest places to buy property in Aspen is on Red Mountain, a neighborhood overlooking downtown Aspen.

The neighborhood attracts so many ultra-wealthy residents that it's earned the nickname, "Billionaire Mountain."

Some of the world's richest families own property on Red Mountain, from Walmart heiress Ann Walton to the Bezos family.

I drove up the mountain to see what prime real estate looks like in the country's richest ski town. I also got a sneak peek into some of Aspen's most exclusive properties currently on the market.

The base of Red Mountain is less than a five-minute drive from Aspen's main street.

At the bottom of Red Mountain is Willoughby Way, which Compass real estate agents Heidi Houston and Doug Leibinger told Insider is considered the most sought-after street in all of Aspen.

"Most people would tell you they think it's the Rodeo Drive, it's the Park Avenue, it's THE address in Aspen," Leibinger told me. "It's a pretty coveted address and location."

"I would suspect that almost every homeowner on this street has two to five properties around the world," Leibinger said. "Most of the people that are here, they've also got a house in the Hamptons. They've also got something in Miami, in St. Barts, in Montecito."

Leibinger explained that although the homes higher on Red Mountain are sometimes bigger and more expensive, Willoughby Way has a unique set of factors that appeal to potential buyers.

Namely, the street is within walking distance to the center of Aspen and still has breathtaking views of the mountains.

Currently, there's only one home on the road for sale — 287 Willoughby Way. And Leibinger predicts it won't be on the market for long.

I toured the five-bedroom, 6,130-square-foot home, which is currently listed at $27 million.

Inside, it's filled with warm woods, floor-to-ceiling windows with mountain views, and a stunning fireplace — all elements I expected in a ski-town mansion.

After touring the $27-million home, I explored the rest of the street. While 287 Willoughby Way was what I expected from a rich ski town, other homes on the road embraced a myriad of styles and designs.

Some homes were visible from the road, but most had private gates and towering trees for added privacy.

I also passed a $72.5-million home — Aspen's largest sale in history. In June, Patrick Dovigi, a former professional hockey player and the founder and CEO of the waste management company Green for Life Environmental, purchased the nine-bedroom, 21,477-square-foot home.

Willoughby Way ends in a cul-de-sac, and as I drove back toward Red Mountain Road, I soaked in views of Aspen and the curving trails from the ski slopes.

Then, I hung a left and started crawling up the mountain.

From here, the homes were tucked into the mountain and farther apart. Private drives jutted into forests, preventing any glimpse of the million-dollar homes.

Down many of those roads were homes reported to belong to billionaires like candy mogul William Wrigley Jr. and casino magnate Neil Bluhm.

One of the most popular names associated with "Billionaire Mountain" is Bezos. Bezos' parents ​​Miguel and Jackie have a home on Red Mountain valued at $20 million in 2012, according to Forbes.

Michael Dell of Dell Computers also has parents with a $10.5-million home in the neighborhood, according to Forbes.

While I didn't spot Bezos or any other billionaire, I did receive access to a private drive leading to one of Red Mountain's most lavish mansions.

Houston took me to The Peak House Estate, the highest residence on Red Mountain. It also happens to be one of the most expensive homes currently for sale in Aspen with a listing price of $44.5 million.

Filled with history and European design, it's a seven-bedroom, 22,000-square-foot mansion.

From its indoor pool to the 12-car garage, the home oozed opulent luxury.

As we left, Houston casually rattled off the names of other billionaires living on Red Mountain.

She pointed to a plot of land, and told me that tucked behind the growth was a mansion belonging to Leslie Wexner, the founder of L Brands, the company that owns brands like Victoria's Secret, Abercrombie & Fitch, and Express, Inc.

There's also media mogul Byron Allen, who purchased a 9,000-square-foot contemporary mansion for $27 million in 2020.

The list goes on and on. And after receiving just a glimpse of the properties on Red Mountain, it's clear how the neighborhood earned its well-deserved nickname of "Billionaire Mountain."

One of the most popular names associated with "Billionaire Mountain" is Bezos. Bezos' parents Miguel and Jackie have a home on Red Mountain valued at $20 million in 2012, according to Forbes.