Most Expensive Small Town: Rancho Santa Fe, Calif

 

No. 16 Most Expensive Small Town: Rancho Santa Fe, Calif.

Median home value: $1,683,818
YOY price change: -8.5%
Population: 3,412
2010 Rank: 11

Eucalyptus-covered hills and citrus groves can be found in Rancho Santa Fe, a community four miles inland from the Pacific Ocean and 25 miles north of downtown San Diego. There are strict building codes in the area to preserve the Spanish Revival and adobe ranch-style architecture. Rancho Santa Fe has been home to golfer Phil Mickelson, singer Janet Jackson, and Taco Bell founder Glen Bell, according to sdrealtypros.com.

No. 15 Most Expensive Small Town: Old Westbury, N.Y.

Median home value: $1,711,174
YOY price change: +2.8%
Population: 5,129
2010 Rank: 23

Old Westbury, a village that belongs to Oyster Bay and North Hempstead, has been home to such wealthy American families as the Whitneys, the Winthrops, and the Phipps. It has miles of developed horse trails and is home to the Old Westbury Gardens, a historic site that includes a mansion, 200 acres of formal gardens, landscaped grounds, woodlands, ponds, and lakes, and which was once the home of businessman John S. Phipps. Median household income is $205,278, according to the Census Bureau.

No. 14 Most Expensive Small Town: Old Brookville, N.Y.

Median home value: $1,714,855
YOY price change: +2.6%
Population: 2,184
2010 Rank: 22

Like the rest of the Brookville area, what is now the village of Old Brookville was part of mid-17th century land purchases from the Matinecock Indians by Oyster Bay Town and early settlers, according to the village website One of the early industries of the town was breeding horses for trolleys and wagons in New York City, according to a town profile on courant.com. Today, this residential community has homes in a range of architectural styles, including Tudor, Victorian, ranch, and modern.

No. 13 Most Expensive Small Town: Quogue, N.Y.

Median home value: $1,718,847
YOY price change: -13.4%
Population: 1,043
2010 Rank: 30

This Southampton town 85 miles east of Manhattan—and just west of the village of Southampton—has Victorian mansions and modern estates with views of the Atlantic Ocean. Quogue is home to a 300-acre nature preserve, the Quogue Wildlife Refuge, which has seven miles of trails, forests, and ponds. Famous residents include actor Michael J. Fox.

No. 12 Most Expensive Small Town: Brookville, N.Y.

Median home value: $1,729,870
YOY price change: -2.8%
Population: 2,689
2010 Rank: 15

Home of the C.W. Post Campus of Long Island University, Brookville was transformed from farm and woodland into a prestigious community in the early 20th century when wealthy New Yorkers started building large estates, according to villageofbrookville.com. The town, about 30 miles from Manhattan, remains one of the wealthiest in the U.S., with median household income exceeding $250,000, according to Census Bureau data. Musicians Jennifer Lopez and Marc Anthony have lived in Brookville.

No. 11 Most Expensive Small Town: Fisher Island, Fla.

Median home value: $1,766,928
YOY price change: +0.2%
Population: 467
2010 Rank: 10

Fisher Island in Miami-Dade County is one of the country's wealthiest areas, with median household income exceeding $250,000, according to Census Bureau data. As no road connects to this exclusive island, it is accessible only by private boat or ferry. Once owned by William Kissam Vanderbilt II, it is known for being a private getaway for celebrities, and homeowners include Julia Roberts, Oprah Winfrey, and Andre Agassi, reports luxist.com.

No. 10 Most Expensive Small Town: Woodside, Calif.

Median home value: $1,792,837
YOY price change: -15.7%
Population: 5,316
2010 Rank: 7

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.

No. 9 Most Expensive Small Town: Sands Point, N.Y.

Median home value: $1,823,677
YOY price change: +9.0%
Population: 2,782
2010 Rank: 19

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.

No. 8 Most Expensive Small Town: Hidden Hills, Calif.

Median home value: $1,871,182
YOY price change: +0.7%
Population: 2,003
2010 Rank: NA

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.

No. 7 Most Expensive Small Town: Rolling Hills, Calif.

Median home value: $2,063,917
YOY price change: +7.3%
Population: 1,921
2010 Rank: 9

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

No. 6 Most Expensive Small Town: Belvedere, Calif.

Median home value: $2,100,453
YOY price change: +1.3%
Population: 2,101
2010 Rank: NA

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.

No. 5 Most Expensive Small Town: Water Mill, N.Y.

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.

No. 4 Most Expensive Small Town: Los Altos Hills, Calif.

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

No. 3 Most Expensive Small Town: Kings Point, N.Y.

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.

 

No. 2 Most Expensive Small Town: Jupiter Island, Fla.

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

 

No. 1 Most Expensive Small Town: Sagaponack, N.Y.

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 HenSilverman 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.

See the Zillow Home Value Index for Sagaponack, N.Y.