The 10 Priciest Neighborhoods in America (And How They Got to Be That Way)

While the ultra-luxury segment of the American housing market is a tiny slice of the overall picture, it does offer some interesting insight into the financial health of some of the country’s real estate market.

“From past experience, ultra-luxury neighborhoods don’t necessarily follow general market trends,” says Skylar Olsen, director of economic research and outreach at Zillow. “These are rare, nuanced sets of homes in the end of the market that recovered much quicker than other parts [following the 2008 recession].”

As another year of reporting far and wide on American real estate comes to a close, we wanted to take a broad and comprehensive look at this growth through examining the 10 most expensive neighborhoods across the country, and exploring why each of these areas are sustaining such high median prices.

To do this, we compiled median price data from four real estate companies that represent different areas of the industry: The Agency, Redfin, Douglas Elliman, and Zillow. Then, we compared price points in the top 15 highest-ranking markets across each list.

This final lineup represents a truer cross section of the most expensive neighborhoods spread out across more markets than the raw data alone. Neighborhoods in the same city/area were averaged out based on median.

10. Di Lido Island (Miami Beach, Fla.) – $4,600,000

We’ve reported at length on South Florida’s housing explosion in up-and-coming neighborhoods, and this is the first of two traditional Miami strongholds that makes our list.

Di Lido Island is the largest of the Venetian Islands—a small chain that sits in Biscayne Bay between Miami Beach and the south side of the Edgewater neighborhood. The longtime celebrity haven is also home to captains of industry and international businesspeople living in both primary and secondary residences.

As you’d expect, they’re also coming for the water.

“Waterfront homes are really now selling for the land value,” says Sladja Stantic, estate agent at ONE Sotheby’s International Realty. Many of Di Lido’s estates were built in the 1920s, which renders them outdated. Developers and individuals are buying up these homes, tearing them down, and putting up mansions like 825 E Dilido Dr., which offers 8,000 square feet of beachside living on the northeast corner of the island. The six-bed, six-and-a-half-bath home is a prime example of the modern architecture trend across the national luxury market and maximizes the available land on the 14,000-plus-square-foot lot.

Developers have to make the most of the available dirt because strict City of Miami regulations mandate that new construction homes can only cover up to 50 percent of the available lot size and be limited to two levels (60 percent for existing structures, though there are certain historic exceptions; our listed example above was built before these new rules came into effect).

It’s an additional hurdle in a small community with top clientele and only 170 residences total on the island.

9. Lacy Estates (San Marino, Calif.) – $4,700,000

For the better part of the last decade, Asian (predominantly Chinese) investment has driven the growth of the San Gabriel Valley in the eastern third of Los Angeles County. In San Marino, median home prices have risen more than $700,000 in the last decade, and that’s even more evident in this particular neighborhood sandwiched between South Pasadena and the busier commercial centers of Alhambra and Rosemead.

“In San Marino, every other house is owned by a Chinese buyer,” says Gus Ruelas, managing partner of the Agency’s Pasadena office. “While they’ve driven values to record highs, I think the majority of houses are being used to park money.”

As is the case in many internationally driven American cities, real estate is seen as a relatively safe investment for foreign wealth. In Lacy Estates, the result has been a swath of homes that were sparsely used or remained empty after the purchase, losing the sense of community that this residential area used to have.

Ruelas has also noticed that prices are starting to plateau. The community issue coupled with growing difficulty for the Chinese buyers to get their money out of China is adding to the amount of time properties are spending on the market.

“In the $5 million to $8 million range, homes that would sell in days [as recently as] two years ago are now on the market for a couple of months,” he says. “Anything above $10 million is taking longer to sell too.”

However, this slowed momentum is presenting new opportunity for domestic buyers, especially those on the other side of Los Angeles. Ruelas has already started to notice the shift with a number of entertainment industry professionals (and celebrities like Meryl Streep) moving east.

8. Palm Island (Miami Beach, Fla.) – $4,800,000

Earlier this year, there was a decent amount of fanfare over the listing of Al Capone’s mansion (now renamed 93 Palm) on the 82-acre Palm Island. While the restored mansion hasn’t yet sold (and has since had a price adjustment), Palm Island is nearing completion of a large face-lift that’s attracting new curiosity and capital to the area beyond the famous property.

“They’ve been pouring a ton of money into raising the streets and returning the island to its original luster,” says Compass Miami/South Florida real estate advisor Tristan Alexander. “There’s much less wondering about what’s going to happen.”

Whereas Di Lido is a flashier, more celebrity-driven community, Palm’s gated access, pristine park, and quieter lifestyle attracts a mix of families, jet-setters, and seasonal owners.

Looking toward 2019, Alexander sees a return of that traditional domestic money that’s driven sales on both Palm and Di Lido Islands.

He notes that political and currency issues have and will continue to slow Latin American and Turkish buyers that have typically fueled Miami’s market. That money may be replaced by a huge push of U.S. buyers from the Northeast and West Coast, along with those seeking opportunity.

“There’s a lot of inventory (on Palm Island) and right now, you can take your pick of the litter,” he says.

7. Aspen, Colo. – $4,869,200

“Aspen is really a ski resort last and a lifestyle first,” says Michelle Sullivan, broker associate at Christie’s International Real Estate Aspen.

This lifestyle of posh dining and entertainment, arts and culture, and, of course, the outdoors has been drawing people to this enclave in the Rocky Mountains for decades.

As expected, secondary and vacation residences, driven by buyers who may have spent years visiting the area before ever considering it a home base, dominate the Aspen market.

Much like other mountainous vacation destinations, there are strict land-use regulations that protect much of the natural beauty surrounding Aspen. Though they safeguard what the hundreds of thousands of annual visitors come to see, they also put a strain on inventory, keeping prices high.

Krista Klees, founding principal at Palladium Properties, an affiliate of Luxury Portfolio International in Aspen, notes that this, among other factors, contributes to a very active market in the $3 million to $5 million range, especially in more central areas of town.

“Downtown and the center have more ‘lock and leave’ options with less annual expenses. These are homes people are spending less than 30 days a year in,” she says.

Both Klees and Sullivan note that activity has slowed above that range, as there’s a considerable jump for someone looking to upgrade their Aspen residence. With little inventory in the $5 million to $7 million range, buyers are forced to spend as much as $4 million more to get into something newer and nicer.

This has also contributed to slowed activity at the ultra-luxury end of the spectrum. Homes above $12 million are sitting longer than they used to as competition heats up for the limited vacation buyer in that range.

“People are potentially just making a shift in general,” Klees says. “At that price point, they’re very significant homes [and that’s tough] in a secondary market.”

However, back at the more active end of the luxury market, Aspen’s growth as a polo destination is driving new interest from South American buyers, while the general summer season (with events like the Aspen Ideas Festival) is drawing culture seekers from places like New York, Florida, Texas, and Canada.

6. Malibu Beach and Point Dume, Calif. – $4,984,404

Malibu has long been home to some of the most expensive—and desirable—homes in the Los Angeles area. As the devastation from the Woolsey Fire unfolds, the consensus from agents is that there will be a pause in the general Malibu market as the community comes together to help each other rebuild and recover.

“The rental market is going to be very strong as we work to get people back into homes,” says Sandro Dazzan, managing partner of the Agency’s Malibu office and one of two agents that were able to return our request for insight. He says that he’s already fielding several calls a day from clients looking for rentals. This should benefit homes that had spent any extended time on the market prior to the fire as sellers may transition them to leasing options, at least in the short term.

With Point Dume suffering among the heaviest losses from the fire, Dazzan estimates that it will take about six months for the market to return to somewhat normal activity.

Rochelle Maize, the executive director of luxury estates at Nourmand & Associates, represented the seller in a Ramirez Canyon sale (near Point Dume) days before the fire began. While the home escaped unscathed, she predicts that this event is going to change how people build and shape their properties. “People are going to be more mindful, especially with landscaping,” she says.

It’s a sentiment that Dazzan echoes, adding that people are going to be much more aware of brush clearance, metal roofs, and other preventative measures.

Both agents agree that this isn’t going to change Malibu’s desirability. Point Dume and Malibu Beach in particular will continue to attract the traditional A-list celebrities and wealthy businesspeople that the area is known for.

“Malibu is still Malibu,” Maize says. “People will come back.”

5. Beacon Hill (Boston, Mass.) – $5,136,700

An older demographic is fueling the fire in Boston’s most desirable neighborhood.

“Many are local—they’re recent empty nesters or [people] leaving big homes in the suburbs to come into the city,” says Beth Dickerson, agent at Gibson Sotheby’s International Realty.

This established wealth is key in driving the exceptional growth of a neighborhood where average prices can run as high as $2,800 per square foot. Dickerson says that all of the new construction that flowed into this historic, picturesque area just north of Boston Common set new standards for what buyers could and would afford.

“In the last several years, we’ve seen numbers north of $1,000 per square foot and it seemed to jump to $1,500 in a year,” she says. “[Suddenly] $1,500 was a good deal as prices moved up well over $2,000.”

As a testament to the high interest in Beacon Hill, Dickerson oversaw the sale of a 4,025-square-foot, three-bedroom penthouse at Maison Vernon for $15.2 million earlier this year. There were three offers in the first week, all above the original asking price of $10.5 million.

Additionally, new construction like the Archer Residences Beacon Hill is establishing a new normal in high-end, amenity-driven living for that same older demographic. The Archer will provide 20,000 square feet of amenity space in a 75-unit building. Pricing starts at $1 million for select one-bedroom units and goes to $18 million for a duplex penthouse.

“There’s a demand for this white-glove, boutique level of service that Boston hasn’t seen before,” says Manuel Davis, senior vice president of Advisors Living, the exclusive listing agents for the Archer.

That evident demand, which also includes buildings like the St. Regis Residences in the Seaport neighborhood (that broke ground last month) and modern remodels currently on the market, makes it clear that Boston’s luxury market isn’t slowing down anytime soon.

4. Sea Cliff, Presidio Heights, and Pacific Heights (San Francisco, Calif.) – $5,167,500

San Francisco’s blistering real estate market earned three spots on our list, all in very close proximity to each other, so we combined the median average into one spot. They’re a trio of historically affluent neighborhoods on the north side of San Francisco proper.

“There’s this notion that once people move to Sea Cliff, they spend the rest of their lives there,” says Compass San Francisco agent Missy Wyant Smit.

She says that this drives extremely limited inventory and has helped spur the continued demand in Pacific Heights and Presidio Heights. A combination of tech executives, entrepreneurs (which she stresses are not just limited to tech), and industrious couples are the leading buyers in our median area.

However, continued volatility and price increases across the city as a whole are pulling a bit of unease into the general market, especially in these high-demand neighborhoods. Compass’s November 2018 SF Real Estate Report notes that while luxury home sales hit an all-time high in San Francisco, “listing inventory has climbed … and the number of price reductions and expired listings have increased.”

Smit agrees that the market temperature is cooling and notes that the numbers in Compass’s latest report don’t reflect fall sales, which are gradually following that cooling trend. However, prices may rebound after the new year.

“When the market starts to shift like this, it’s a challenge to get buyers to make a move,” she says. “Only time will tell, but what I’ve said to my buyers is that we may look back at the fall 2018 market and say that it was a season of good deals for buyers compared to next spring’s market.”

Regardless of any broader slowdown, Sea Cliff, Presidio Heights, and Pacific Heights will continue to be hot. According to the Compass report, houses selling for $3 million and above (like the on-market 3112 Washington St. in Pacific Heights) hit a new all-time high in October with the Heights-Marina area as one of two neighborhoods (determined by their qualifiers) leading the way.

These areas will continue to lure buyers looking for quieter, more residential experiences with a bit of respite from the grind and hustle of San Francisco’s core.

3. Shady Canyon (Orange County, Calif.) – $5,700,000

This gated community in Orange County is nestled into the rolling hills between Irvine and Laguna Beach with 400 home sites built on lots that average a half to three-quarter acres. Although it’s less than 20 years old, it quickly attracted a large contingent of predominantly Chinese buyers that drove up prices.

Those prices peaked in 2016/2017, and now the investment has started to slow, according to Andrew McDonald, director of luxury properties and managing partner of the Agency’s Orange County office.

“Local money is filtering back in,” he says. “It’s a discerning, classy choice for serious wealth.”

That wealth includes athletes like Mark McGwire and Albert Pujols, leaders of industry, and others that are looking for privacy while being minutes away from main hubs inland and on the coast.

The highly rated Shady Canyon Golf Club is also a significant draw, as it sprawls for 300 acres and intertwines with a variety of hiking, biking, and other outdoor activities across the community’s 1,100 acres. “[Because of the natural surroundings], you kind of lose track where you’re at,” McDonald says.

That slice of serenity and exclusivity is a key feature that buyers don’t get in busy Newport Beach or Laguna Beach. Coupled with the aforementioned golfing and discretion that comes with a quiet, gated community, the sum is an attractive locale that leaves buyers willing to pay a premium.

However, as attractive as all of the amenities are, the local market is beginning to soften. McDonald says properties are now sitting on the market six to 12 months and offering exceptional value for prospective buyers.

While local investment rebuilds the value vacated by the international money, Shady Canyon will continue to shift into this transition phase.

2. Silicon Valley, Calif. – $5,706,250

The only region to present more neighborhoods on our list than San Francisco was its immediate partner to the south. Four neighborhoods made our top ten list with several more in the top 20. The areas of Atherton, Old Palo Alto, Professorville, and Crescent Park make up our median areas for an incredible concentration of high home prices.

“The money in the last 10 years has become more extreme,” says Eric Boyenga, founding partner of Compass Silicon Valley.

These areas in particular are drawing that money because of how close they are to downtown commercial areas and the core of venture capital firms on Sand Hill in Menlo Park.

As one would expect, Silicon Valley is driven by the success of the tech and stock markets, which means the amount it actually costs to build a home in these highly desirable neighborhoods rapidly fluctuates. Boyenga says that California’s Prop 13—which dictates property taxes through varying assessments—is also making property owners think twice before putting a home on the market, adding a further strain on inventory.

“There’s no other place in the U.S. that costs as much to build as it does here,” he says. “We have a lack of good builders—and many of these buyers want their house built like a microchip—so the builders can command a premium. In places like Palo Alto, Atherton [and the adjacent Woodside], you could have 10 to 14 people involved in a project just getting everything approved to build.”

Truthfully, with all of the socioeconomic factors taken into consideration, these four neighborhoods will continue to command a special premium that’s causing sticker shock even to those with unlimited means.

“[Even] billionaires come here and they’re astounded by the prices,” Boyenga says.

1. Port Royal (Naples, Fla.) – $8,200,000

A quick Google search of Port Royal Naples is all you need to see to understand that the most expensive neighborhood in the country is driven by its high-end real estate listings. Almost the entire first two pages of results are either links to listings, vacation rentals, or stories about high-priced properties.

“It’s a very unique piece of property with a majority of homes on the water with wide canals,” says Joe Belz, a real estate advisor at Compass Naples. (Roughly 85 to 90 percent of Port Royal lots have deep-water access to the Gulf of Mexico.)

The coastal neighborhood has long been a destination for celebrities, C-level executives, and just about anyone from any industry with considerable wealth. The median price we determined is really an entry point for a family trying to get into Port Royal. For a four-bedroom, four-bath waterfront home, you’re easily looking at an asking price north of $8.5 million.

With that price comes a membership to the Port Royal Club, which Belz says is a very popular draw for those buying in the neighborhood. Prospective owners tend to come from the Midwest, but buyers from the Northeast states are starting to show more interest, especially those from Boston.

As of November 14, there were 52 homes for sale in Port Royal, showing about a 16.5-month supply, which Belz says isn’t much of an inventory given the price points. He adds that the waterfront draw even attracts those who aren’t necessarily big-time boaters, but want exceptional views and a more opulent lifestyle.

With new, record-breaking transactions like the $48.8-million sale in June of 2500 Gordon Drive, it’s fair to say that interest in the ultra-luxury side of the market (which makes up a vast majority of Port Royal) is self-sustaining. Given the low inventory and developers’ continued interest in tearing down old multimillion-dollar mansions and combining multiple lots to create larger estates, Port Royal could easily remain at the top of this list for some time.