Most Expensive American Small Towns

Businessweek.com worked with real estate website Zillow.com to rank the most expensive small towns around the country based on their median home value. A total of 4,624 places with populations less than 10,000 were evaluated. Two states dominate the list: New York with 22 towns and California with 13 towns. Other states in this ranking include Colorado, Florida, Massachusetts, Maryland, New Jersey, and Washington. A newcomer to the list is Tennessee, where Belle Meade came in as the 48th most expensive small town.

10. Woodside, CA
Median home value: $1,792,837
YOY price change: -15.7%
Population: 5,316

Many Silicon Valley moguls have owned homes in Woodside, including Apple co-founder Steve Jobs, Oracle Chief Executive Officer Larry Ellison, and Intel co-founder Gordon E. Moore. The town is also home to Buck’s of Woodside, a local restaurant that is famous as a meeting place for the area’s entrepreneurs and venture capitalists. The area is also known for its equestrian lifestyle, and the town maintains a system of horse trails. The U.S. Census Bureau estimates median household income at $214,310.

9. Sands Point, NY
Median home value: $1,823,677
YOY price change: +9.0%
Population: 2,782

Sands Point, a Long Island village about 25 miles from Manhattan, is reputed to be the inspiration for East Egg in F. Scott Fitzgerald’s The Great Gatsby (West Egg is said to be based on Kings Point). The town was incorporated in 1910 and originally owned by three families, the Sands, Cornwells, and Vanderbilts, according to longislandexchange.com. Other wealthy residents later moved in, including the Guggenheims. Sands Point is home to a nature preserve owned and maintained by Nassau County, and a private golf club. Median household income is $204,286, estimates the U.S. Census Bureau.

8. Hidden Hills, CA
Median home value: $1,871,182
YOY price change: +0.7%
Population: 2,003

A small, gated community about 35 miles west of downtown Los Angeles, Hidden Hills is one of the wealthiest communities in the U.S. Median household income exceeds $250,000, according to the U.S. Census Bureau. It has been home to Marvin Gaye, Lisa Marie Presley, the Jenner-Kardashian family, Ozzy and Sharon Osbourne, and Denise Richards, and was the setting of an eponymous NBC sitcom that aired from 2002 to 2003, according to hiddenhillsnewz.com.

7. Rolling Hills, CA
Median home value: $2,063,917
YOY price change: +7.3%
Population: 1,921

A rural, ranch atmosphere characterizes this gated community in Southern California, which has equestrian paths along the streets and no curbs, gutters, or streetlights, according to rollinghillshomes.com. Rolling Hills has fewer than 700 homes, with no apartments, condominiums, or commercial buildings. Median household income is $205,417, according to the U.S. Census Bureau.

6. Belvedere, CA
Median home value: $2,100,453
YOY price change: +1.3%
Population: 2,101

A small city across the bay from San Francisco and near Tiburon, Belvedere comprises three neighborhoods: Belvedere Island, Belvedere Lagoon, and Corinthian Island. Many homes have views of San Francisco, Angel Island, the Golden Gate Bridge, Sausalito, and Mt. Tamalpais. Originally a fishing community, Belvedere today is a sailing community, home to the San Francisco Yacht Club and close to the Corinthian Yacht Club.

5. Water Mill, NY
Median home value: $2,111,688
YOY price change: -10.0%
Population: 2,137
2010 Rank: 6

Water Mill, about 90 miles from Manhattan, offers riding stables, golf courses, and some of the finest sailing and fishing waters in the Northeast. The town has been home to actor Richard Gere, fashion designer Adrienne Vittadini, artist Setsuo Ito, publishing heiress Anne Hearst, and real estate investor Andrew Borrok.

4. Los Altos Hills, CA
Median home value: $2,161,255
YOY price change: -13.6%
Population: 7,981
2010 Rank: Unchanged

The elite town of Los Altos Hills, a wealthy Silicon Valley community 35 miles south of San Francisco and 17 miles north of downtown San Jose, encompasses 8.4 square miles. It has 65 miles of trails and off-road paths for walking, running, bicycling, or even horseback riding. Residents have included Google co-founder Sergey Brin, Yahoo! co-founder Jerry Yang, Hewlett-Packard co-founder David Packard, and venture capitalist Kelly Porter. Median household income is $218,922, estimates the U.S. Census Bureau.

3. Kings Point, NY
Median home value: $2,379,905
YOY price change: +13.5%
Population: 5,132
2010 Rank: NA

This Long Island village, home of the U.S. Merchant Marine Academy, is reputed to be the inspiration for West Egg in F. Scott Fitzgerald’s The Great Gatsby (Kings Point even has a road named Gatsby Lane). The area has two main parks: Steppingstone Park, which offers mooring for more than 300 boats, and the 175-acre Kings Point Park. Kings Point was home to Chrysler founder Walter Chrysler, retailer Henri Bendel, and comedian Alan King, according to longislandexchange.com.

2. Jupiter Island, FL
Median home value: $2,810,434
YOY price change: -11.3%
Population: 875
2010 Rank: Unchanged

The town of Jupiter Island, which developers in the 1920s originally envisioned building into a Hollywood-like center for production companies and movie stars, is well-known as one of the wealthiest places in the country. The U.S. Census Bureau estimates per capita income to be $235,758. It has a permanent population of 584, with a seasonal population of approximately 1,775, according to the town website. Jupiter Island has been a second home for many old wealthy American families such as the Doubledays, Fords, Heinzes, and Mellons, and residents have included golfers Greg Norman, Nick Price, and Tiger Woods, President George H.W. Bush, actor Burt Reynolds, and baseball star Mike Schmidt, according to Corcoran.

1. Sagaponack, NY
Median home value: $3,406,640
YOY price change: -14.5%
Population: 582
2010 Rank: Unchanged

Southampton’s ritzy village of Sagaponack maintains its rank as the country’s most expensive small town in 2011. The village, which covers eight square miles, has been home to musician Billy Joel, Apollo Management Chief Operating Officer Henry Silverman, and former Kinray Chief Executive Officer Stewart Rahr. It is also the site of Fair Field, the 63-acre oceanfront estate of Renco Group Chief Executive Officer Ira Rennert, who owned military Humvee maker AM General. At 66,000 square feet and with a 164-seat theater, three swimming pools, and a two-lane bowling alley, Fair Field is one of the largest private houses in the country.