The 20 Most Expensive Places to Buy a Home

A move to an idyllic small town in America — you know, picket fences, oak-lined streets — doesn't always mean a move to a smaller mortgage.

February 10, 2022

By: Erin Gifford

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A Small Town Does Not Always Mean a Small Mortgage

LendingTree wanted to know whether a move to an idyllic small town in America — you know, picket fences, oak-lined streets — also meant a move to a smaller mortgage. They quickly found that would not be the case. In fact, some small towns are far more expensive than you would think. To come up with their findings, Lending Tree pored over data collected by the US Census Bureau to identify the small US towns — with populations ranging from 10,000 to 50,000 — with the most expensive median home values. Generally, the priciest towns were vacation spots frequented by the affluent, like Breckenridge, Colorado and Jackson, Wyoming.

However, some expensive towns had homes with high sticker prices due to simple lack of housing supply, like in Williston, ND. Take a look at how pricey housing can get in our small towns. In order, here are the 20 most expensive small towns to buy a house in the United States.

Learn More: The 20 Richest Towns in America

1. Vineyard Haven, Massachusetts

What do Meg Ryan, Jennifer Lawrence and the Obamas have in common? They all either own homes on or frequent Martha's Vineyard, the island south of Cape Cod. It's where the rich and famous flock for vacation, causing the island to swell more than ten-fold in summer to a population of nearly 200,000. Vineyard Haven, one of six towns on Martha's Vineyard, is the entry point for visitors arriving by ferry. Imagine all the celeb spotting at the ferry dock alone. It's no wonder home prices are through the roof, with a median home value of nearly $700,000. Of course, there are the unspoiled beaches, vibrant sunsets, cedar shake siding and fresh seafood, too.

2. Breckenridge, Colorado

There's nothing cheap about putting down stakes in Breckenridge, and these days you'll need to dig deeper into your wallet to land a ski-in ski-out property in this popular, yet low-key mountain town. A luxe 7,200-square-foot chalet sold for $17 million recently, breaking the previous record for the most expensive home in this alpine village. It's pricey just to be in Breckenridge, too. For skiers, single-day lift tickets run $198 each, but you're guaranteed fresh powder, thanks to 300+ inches of snow that fall each winter. Mild 70 degree summer days are also a huge draw.

3. Jackson, Wyoming

Want to rub elbows with a billionaire or two, even three? Set your sights on Jackson. Home to three billionaires, the combined net worth of these wildly wealthy Jackson residents is more than $50 billion. With its mountainous terrain, picturesque landscape and notoriety as a tax haven (there is no state income tax in Wyoming), it's no wonder the rich and richer call Jackson home. Or, one of their homes. A mecca for outdoor enthusiasts, you can ski, paddle, climb, hike, bike, even watch wildlife at the National Elk Refuge. Grand Teton National Park is also a short drive from Jackson.

4. Steamboat Springs, Colorado

Not only is Steamboat Springs an expensive place to live — the median home value tops $535,000 — but it's among the most costly places to ski in the United States. Known as Ski Town, USA, single-day lift tickets hit $225 in the 2020-21 season, so it's not cheap to hit the slopes once you settle into a home. One huge draw is the town's Olympic heritage, having trained 98 Olympic athletes (and counting). Steamboat is home to the largest natural ski jumping complex in North America, and it's not unusual to see an Olympian around town. The Tread of Pioneers Museum has been known to host a "Meet an Olympian" talk on select Saturdays during ski season.

5. Hailey, Idaho

Over the last few years, urban dwellers have opted to leave the big city behind in favor of more space, fewer people and all the fresh air they can breathe in. That trend has been especially apparent in Idaho, according to Rocket Homes. The housing market is booming, and that's driving home prices up, up, up, especially in towns like Hailey. Located on the edge of national forest land and just south of Sun Valley, Hailey is the place to go to get outdoors for stargazing, fly fishing, cycling, and of course, skiing. Notably, Hailey also made the list of the top-10 safest cities in Idaho, as compiled by SafeWise.

6. Gardnerville Ranchos, New Mexico

The small town of Gardnerville Ranchos in the Sierra Nevadas isn't abundantly well-known, but given its proximity to South Lake Tahoe (40 minutes away) and Heavenly Mountain Resort (30 minutes), it's no surprise to see this village listed among the most expensive places to live. Retirees flock to this town in Nevada's Carson Valley for picturesque mountain vistas, peaceful gardens and access to plenty of outdoor activities in all seasons. Ski at Heavenly Mountain Resort in winter, then take the gondola to the top of the mountain for wildly scenic views across Lake Tahoe in summer.

7. Hood River, Oregon

It's not cheap to live in Hood River, but the scenic panoramas may make up for the raging home prices. Even home rentals are quite expensive, as well as very limited. However, there's no sales tax in Oregon, so that's a plus. It's expensive to shop in town, but you'll be overwhelmed by the beauty, as well as Adams Mountain and Hood Mountain. Simply spectacular. Tucked into the Columbia River Gorge, visitors come for windsurfing, kayaking, hiking and waterfall watching. Hood River is an escape to the great outdoors and an easy town to fall for quickly.

8. Juneau, Alaska

Nestled into the Alaskan Panhandle, the state capital of Juneau is a small, rural community of only 32,227 residents. The town may not be big, but you'll find plenty of big prices. The homes are expensive, as are gas, groceries and utilities. This is because consumer goods can only come in by sea or by plane. There are no roads or highways that connect Juneau to the rest of the state. However, high earnings help offset the costs. The median household income in Juneau is $88,390, the second highest among the 20 towns with the most expensive home prices, per LendingTree.

9. Easton, Maryland

Maryland's Eastern Shore, which lies on a peninsula between the Atlantic Ocean and the Chesapeake Bay, has become an attractive destination among well-to-do second-home owners. Posh boutiques, art galleries and cultural attractions have sprung up in Easton to cater to homeowners, not just weekend shore-seekers. According to the Maryland Association of Realtors, average home prices have jumped 46% year over year with the boom in demand among those eager for their own slice of waterfront paradise on the Delmarva Peninsula.

10. Los Alamos, New Mexico

There are more than a few millionaires in Los Alamos. Once home to the scientists who helped create the nuclear bomb, present-day Los Alamos is a small community (population: 18,625) 35 miles northwest of Santa Fe with the largest concentration of millionaires in the United States. In fact, one in seven households is a millionaire household, so it comes as no surprise to see such high home prices in the desert landscape. According to LendingTree, the median household income is higher in Los Alamos than in any other city in their study at $121,324. Come for historical attractions, outdoor recreation, scenic panoramas and diverse wildlife.

11. Ketchikan, Alaska

Ketchikan is more than a port stop for mega cruise ships navigating the Inside Passage, though cruise ships do make more than 500 stops here each year. One million passengers disembark annually in Ketchikan to celebrate Alaskan Native culture, totem poles, a lush temperate rainforest and salmon at Ketchikan Creek. Housing is in demand, fueling a rise in home prices, and rentals are in short supply. Much like Juneau, everything is expensive in Ketchikan, not just homes. Because Alaska is large and sparsely populated, it costs more to ship products, making everything from lumber to gas to retail goods — including souvenirs — more costly.

12. Kill Devil Hills, North Carolina

Over the summer, the most expensive home ever listed on North Carolina's Outer Banks hit the market. The whopping 11,000-square-foot oceanfront estate on this sun-splashed stretch of barrier islands has an $11 million price tag. This property is in Corolla, a stone's throw from Kill Devil Hills, but you'll find more than a few million dollar listings in Kill Devil Hills, too. Given the area's immense popularity as a coastal escape from urban centers, like Washington DC and Richmond, it's no surprise to see home prices soaring and wealthy buyers eager to watch the sunrise from their decks.

13. Fredericksburg, Texas

Not only does this well-known destination in the Texas Hill Country have expensive homes, but Fredericksburg is also considered the most "unaffordable" city in Texas. That's according to a study by WalletWyse. Yup, everything is bigger in Texas, even the home prices. At least in Fredericksburg. For a state with a cost of living that's below the national average, the home prices in Fredericksburg can lead to sticker shock. Yet, there's much to love, including wineries, outdoor recreation, fruit orchards, shopping on "The Magic Mile" and German culture, leading many to overlook the home prices and settle into the good life in Texas Hill Country.

14. Ellensburg, Washington

Near the center of Washington State sits Ellensburg, a town of 45,897 that's best known as host to the largest rodeo in the state. Situated in the Kittitas Valley, Ellensburg is halfway between Seattle and Spokane. For a town few people know, it's one of the most expensive places to live in the US. Ellensburg sees 300 days of sunshine each year and is much loved as a destination for water skiing, cross-country skiing, fly fishing and white water rafting. With so much to do outdoors each season, it's no wonder visitors and home buyers flock from far and near for a piece of Ellensburg.

15. Astoria, Oregon

Astoria may be the oldest city in Oregon and the first American settlement west of the Rockies, but for Gen Xers, this coastal village is best known for The Goonies, a 1985 film set in Astoria that follows a group of kids in search of pirate's treasure. The movie features lots of glamour shots, including Ecola State Park, Cannon Beach and Haystack Rock, one of Oregon's most well-known landmarks. Given Astoria also frequently tops all kinds of "best towns" of Oregon lists, it's no wonder home prices are high and buyers want to be a part of this coastal community.

16. Sheridan, Wyoming

Sheridan is widely considered one of the best places to live in Wyoming. However, it's not one of the cheapest places to live in Wyoming despite the state's lower than average cost of living. The schools are very good, even nightlife is good, and it's hard to beat being less than four hours from Yellowstone National Park and Mount Rushmore. Sheridan is well known for its Old West history, cowboy and rodeo culture and Native American influences. Many home buyers are eager for vacation homes to take advantage of Wyoming's wide open spaces.

17. Brookings, Oregon

Situated along Oregon's Wild Rivers Coast, Brookings is known for rugged coastline, colorful tidal pools, large rock formations and Instagram-worthy sea stacks. It's the first beach town you reach as you cross into Oregon from California on Highway 101. Who knows how many travelers continue north or settle in for a longer than planned stay in Brookings? Certainly, the home prices are more expensive, but it's a small trade-off for quiet and safety, not to mention great schools and loads of outdoor recreation opportunities at state parks and sandy beaches, including 12 miles of coastline at the Samuel H. Boardman State Scenic Corridor.

18. Sandpoint, Idaho

Set on Lake Pend Oreille, Sandpoint is known for ski slopes, bike terrain parks and yes, sandy beaches. As in, those you'll find on the lake shores. This small resort town is noted for having the fifth largest natural lake in the lower 48 states. Its unspoiled nature attracts those eager for an urban escape. Go kayaking in summer, and in winter schuss on the slopes at Schweitzer Mountain Resort, the largest resort in Idaho. Despite its remote feel, the ski resort is a short 25-minute drive from town. Sandpoint isn't for the budget-conscious — it's the most expensive place to live in Idaho, according to HomeSnacks — but it’s a wildly beautiful destination worthy of exploration.

19. Newport, Oregon

There's so much to love about Oregon, but it's also one of the more expensive places to live and buy a home, particularly along the wind-swept Oregon Coast. All three of the Oregon towns on LendingTree's list of towns with the most expensive homes sit on the Pacific Ocean, including Newport. Home to Oregon's tallest lighthouse, Newport wows with pristine coastline for watching wildlife, like whales and bald eagles. While a nature lover's paradise, Newport can be pricey. Oregon has one of the highest income taxes in the country, but thankfully, no state or local sales taxes.

20. Williston, North Dakota

Just 60 miles south of Canada, Williston is often referred to as the "Western Star" and takes great pride in its Western culture and heritage. Home to more than 200 oil service companies, as well as the Bakken Oil Fields, Williston employs many residents working in the country's second largest oil-producing state. In recent years, population growth skyrocketed due to ramped-up activity in the oil and gas industries, but housing couldn't keep pace. It's no surprise then that homes are expensive and rentals are scarce in this boomtown near the confluence of the Yellowstone and Missouri Rivers.