Where to buy a second home? Shouldn’t we all be lucky enough to have this dilemma? At Concierge Auctions we have often catered to second home buyers. We have worked in well known second home enclaves like Hawaii and Martha’s Vineyard.
Some say that luxury home prices are faring better than median home prices, and I tend to agree with that sentiment. With that said, prices on luxury vacation homes are still lower now than they were five years ago. While the market for luxury second homes may continue to drop slightly in some areas in the coming years, many second home seekers feel like now is the time to buy.
With that in mind here are my Top 5 best places to buy a second home:
1. KAUAI, HAWAII: We just completed a successful auction of 34+ oceanfront acres in Kauai, which was one of the highest priced sales of land on the island in 5 years. So, Kauai is on my mind. Kauai has all the beauty and great weather of Oahu without all the hustle and bustle. It is the perfect place to buy a second home and get away from city life. Kauai boasts world-class golf, beaches, and adventure sports. See 10 Reasons to ‘buy in Kauai’ for more great reasons to get a second home on this most tranquil of the Hawaiian Islands.
2. VAIL, COLORADO: Vail is of course known as a world-class ski destination, and it has one of the largest ski areas in North America. If you are looking for some action in your second home purchase then Vail is the place. The ski slopes will be packed half the year, and after hitting the slopes, you can hit up one of many upscale restaurants or bars. Tons of professional skiers and snowboarders make their home in Vail. Vail also has a lively music scene throughout the year.
3. JACKSON HOLE, WYOMING: Another great ski destination, Jackson Hole is the place to go for more advanced skiing. Half the mountain is designated as “experts only.” The Snake and Platte rivers are nearby for fishing too, and Jackson Hole has some of the most adventurous local dinning options with choices like buffalo and antelope appearing at many local eateries. You can get a lot of acreage around Jackson Hole for good prices. Harrison Ford has an 800-acre ranch in the area. Tiger Woods is also a second home owner and likes to golf in Jackson Hole.
4. MARTHA’S VINEYARD, MASSACHUSETTS: The Vineyard is like an island stuck in time. While cars are allowed, they seem to be outnumbered by mopeds and bicycles much of the year. Like to sit on a deck and enjoy ocean views while eating fresh lobster and local foods? Then Martha’s Vineyard is the place to buy a second home. President Obama and family vacation here yearly, and President Clinton, along with Hillary and Chelsea, have vacationed here for years.
5. SUN VALLEY, IDAHO: This is an old haunt of Ernest Hemingway, and he completed his novel For Whom the Bell Tolls in Sun Valley. All the while he was surely hunting and fly-fishing, which are both world class in the Sun Valley. There is also plenty of snow skiing in the winter. Perhaps a legacy of Hemingway, Sun Valley has a lively arts community with numerous theaters, galleries, and film festivals. Second home owners in Sun Valley include Arnold Schwarzenegger and Mark Zuckerburg. We have the perfect Sun Valley luxury second home coming to auction: Sun Valley Real Estate Auction.
Thinking about buying a second home in one of these markets or any other market? Sign up for our Luxury Real Estate Auction Alerts and we will email you with upcoming auctions.

