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America's 50 Most Expensive Small Towns 2011

  1. Small Towns, Big Money
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    Small Towns, Big Money

    Rich people may like to travel, but like everyone else they want to keep their daily commute as short as possible. So when it comes to buying a home, they want to be close to work, and because they're rich they can pretty much be where they like. But they also like safe neighborhoods, good schools, pretty views, and, if possible, access to beaches and country clubs. Small wonder then that those towns which offer all the above and are nearest to the crossroads of money and power are among the priciest in the nation. Of course, sometimes the reverse is true. The very rich also tend to have at least one second home, so the places where they gravitate—the Hamptons, Martha's Vineyard, Palm Beach—may be chosen for their distance from the office.

    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.

    Click here to see the country's 50 most expensive small towns, where median home values all exceed $1 million.
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  2. No. 50 Most Expensive Small Town: Lake Success, N.Y.
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    No. 50 Most Expensive Small Town: Lake Success, N.Y.

    Median home value: $1,030,048*
    YOY price change: +0.6%*
    Population: 2,810*
    2010 Rank: NA

    The village of Lake Success, 16 miles east of Manhattan, was the temporary headquarters for the U.N. from 1946 to 1951. One of nine villages that make up the Great Neck area in Nassau County, Lake Success covers about two square miles and has two golf courses and a Great Neck Public School Complex, according to the village website.

    See the Zillow Home Value Index for Lake Success, N.Y.

    *November 2010 median home value, year-over-year price change, and population source: Zillow.com. Some expensive towns in the 2010 ranking were not included this year because of incomplete data.

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  3. No. 49 Most Expensive Small Town: Gulf Stream, Fla.
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    No. 49 Most Expensive Small Town: Gulf Stream, Fla.

    Median home value: $1,059,601
    YOY price change: +1.8%
    Population: 757
    2010 Rank: NA

    The town of Gulf Stream, between Palm Beach and Boca Raton, is an affluent community in Palm Beach County. The town became a popular winter resort destination for the wealthy after the Gulf Stream Polo Club opened in the 1920s, according to pbchistoryonline.org. Many recreational amenities are available in the area, including Gulfstream Park (a horse racing and casino resort), golf courses, tennis courts, and deep-sea fishing.

    See the Zillow Home Value Index for Gulf Stream, Fla.

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  4. No. 48 Most Expensive Small Town: Belle Meade, Tenn.
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    No. 48 Most Expensive Small Town: Belle Meade, Tenn.

    Median home value: $1,064,338
    YOY price change: +8%
    Population: 2,917
    2010 Rank: NA

    Belle Meade is a wealthy suburb of Nashville where the median household income is $232,500, according to U.S. Census Bureau 2005-2009 estimates. Former Vice-President Al Gore owns a home in Belle Meade. The area has large, private estates and horse trails, and is close to the Warner Parks complex, which has a nature center, hiking trails, equestrian facilities, golf courses, and athletic fields. The city is also home to the Belle Meade Plantation, a 30-acre historic site that was a horse farm with a mansion built in 1853.

    See the Zillow Home Value Index for Belle Meade, Tenn.
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  5. No. 47 Most Expensive Small Town: Avalon, N.J.
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    No. 47 Most Expensive Small Town: Avalon, N.J.

    Median home value: $1,065,538
    YOY price change: -2.8%
    Population: 2,284
    2010 Rank: NA

    This coastal community in southern New Jersey's Cape May County is a popular vacation destination and has a large seasonal population. In fact, only 18.4 percent of 5,434 housing units in the borough are occupied, according to 2005-2009 estimates from the U.S. Census Bureau. The Avalon School District has an elementary school that teaches grades one to eight and had a total enrollment of 75 students in the 2009-10 school year. Kindergarten and high school students attend schools in nearby districts.

    See the Zillow Home Value Index for Avalon, N.J.

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  6. No. 46 Most Expensive Small Town: Cherry Hills Village, Colo.
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    No. 46 Most Expensive Small Town: Cherry Hills Village, Colo.

    Median home value: $1,065,780
    YOY price change: -0.5%
    Population: 5,979
    2010 Rank: NA

    An affluent suburb of Denver incorporated in 1945, Cherry Hills Village is well-known for the Cherry Hills Country Club, which has hosted several U.S. Golf Assn. championships. The area is served by two highly regarded school districts: Littleton Public Schools and Cherry Creek School District. The Census Bureau estimates median household income to be $226,552.

    See the Zillow Home Value Index for Cherry Hills Village, Colo.

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  7. No. 45 Most Expensive Small Town: North Haven, N.Y.
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    No. 45 Most Expensive Small Town: North Haven, N.Y.

    Median home value: $1,065,916
    YOY price change: -9.7%
    Population: 886
    2010 Rank: 48

    A coastal village of Southampton in eastern Long Island, North Haven offers residents and visitors bay waters and beaches. It is known for having a terminal for the Shelter Island ferry. Some famous North Haven residents have included musician Jimmy Buffett, composer Irving Berlin, and actors John Drew, Ethel Barrymore, Douglas Fairbanks Jr., and Mary Pickford, according to longislandexchange.com.

    See the Zillow Home Value Index for North Haven, N.Y.


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  8. No. 44 Most Expensive Small Town: Travilah, Md.
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    No. 44 Most Expensive Small Town: Travilah, Md.

    Median home value: $1,066,977
    YOY price change: -6.5%
    Population: 7,442
    2010 Rank: NA

    Travilah is a wealthy suburb near the Maryland-Virginia border, about 23 miles from Washington, D.C. It is near several parks and golf clubs, including Lakewood Country Club in Rockville and Bretton Woods Golf Course in Germantown. Median household income in Travilah is $199,414, according to Census Bureau estimates.

    See the Zillow Home Value Index for Travilah, Md.

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  9. No. 43 Most Expensive Small Town: Hewlett Harbor, N.Y.
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    No. 43 Most Expensive Small Town: Hewlett Harbor, N.Y.

    Median home value: $1,067,766
    YOY price change: +3.3%
    Population: 1,284
    2010 Rank: NA

    Hewlett Harbor, a village on Long Island's South Shore incorporated in 1925, has many luxury homes near the Seawane Golf and Country Club and on the waterfront by Macy Channel and Willow Pond. The community, about 25 miles from Manhattan in Nassau County, was home for many years to Stan Lee, co-creator of Spider-Man (among other popular superheroes) and former president and chairman of Marvel Comics.

    See the Zillow Home Value Index for Hewlett Harbor, N.Y.

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  10. No. 42 Most Expensive Small Town: Emerald Lake Hills, Calif.
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    No. 42 Most Expensive Small Town: Emerald Lake Hills, Calif.

    Median home value: $1,085,907
    YOY price change: -2.3%
    Population: 3,983
    2010 Rank: NA

    Emerald Lake Hills, a neighborhood about 30 miles southeast of San Francisco, was originally developed as a weekend or vacation community for San Franciscans in the 1920s, according to the website of the Emerald Hills Homeowners Assn. Many recreational attractions are available to residents, including the Edgewood County Park, Emerald Lake Country Club, Upper Emerald Lake, Lower Emerald Lake, and Handley Rock Park in the center of Emerald Hills.

    See the Zillow Home Value Index for Emerald Lake Hills, Calif.

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  11. No. 41 Most Expensive Small Town: Lattingtown, N.Y.
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    No. 41 Most Expensive Small Town: Lattingtown, N.Y.

    Median home value: $1,113,998
    YOY price change: -5.5%
    Population: 1,860
    2010 Rank: NA

    Lattingtown, a village in the town of Oyster Bay on Long Island's "Gold Coast," is about 35 miles from Manhattan. It is known as an exclusively residential area with large mansions. It has a beach, an 18-hole golf course at the Creek Club, and three nature conservation areas. It is also home to the Bailey Arboretum, which has 40 acres of woods, ponds, and gardens.

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

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  12. No. 40 Most Expensive Small Town: Del Mar, Calif.
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    No. 40 Most Expensive Small Town: Del Mar, Calif.

    Median home value: $1,134,564
    YOY price change: -8.0%
    Population: 4,370
    2010 Rank: NA

    Del Mar, a San Diego County beach town, attracts many surfers and outdoor enthusiasts with two miles of coastline, beaches, parks, and the nearby Torrey Pines State Natural Reserve. It is also well-known for its thoroughbred racetrack and county fair. The area's most exclusive homes have views of the Pacific Ocean. The town was home to actor Desi Arnaz.

    See the Zillow Home Value Index for Del Mar, Calif.

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  13. No. 39 Most Expensive Small Town: Clyde Hill, Wash.
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    No. 39 Most Expensive Small Town: Clyde Hill, Wash.

    Median home value: $1,156,705
    YOY price change: -3.9%
    Population: 2,845
    2010 Rank: 47

    Clyde Hill is a residential community two miles east of Seattle, next to downtown Bellevue and the town of Medina, which is home to Microsoft founder Bill Gates. With a top elevation close to 375 feet, the town offers scenic views. Residents can enjoy vistas of Lake Washington, Mt. Rainer, the Olympic Mountains, the Cascade Mountain range, as well as the Seattle and Bellevue skylines. Clyde Hill is served by the highly regarded Bellevue School District.

    See the Zillow Home Value Index for Clyde Hill, Wash.

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  14. No. 38 Most Expensive Small Town: Great Neck Estates, N.Y.
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    No. 38 Most Expensive Small Town: Great Neck Estates, N.Y.

    Median home value: $1,226,818
    YOY price change: +1.8%
    Population: 2,749
    2010 Rank: NA

    Once home to writer F. Scott Fitzgerald, Great Neck Estates was incorporated in 1911 as one of nine villages on the Great Neck peninsula. Many residents of this wealthy community work in Manhattan, which is nearly 20 miles away and accessible by mass transit. Community events are held at the Great Neck Estates Park, which has a swimming pool, tennis courts, a marina and dock area, sports fields, and basketball and handball courts.

    See the Zillow Home Value Index for Great Neck Estates, N.Y.

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  15. No. 37 Most Expensive Small Town: Munsey Park, N.Y.
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    No. 37 Most Expensive Small Town: Munsey Park, N.Y.

    Median home value: $1,233,283
    YOY price change: +2.5%
    Population: 2,612
    2010 Rank: NA

    Munsey Park, home to Long Island's "Miracle Mile" shopping area, almost exclusively has colonial, Tudor, and Norman-style homes, and strict building codes aim to preserve its ambience. The village, 20 miles from Manhattan, is also close to beaches, museums, town and county parks, and recreation facilities. Median household income is $237,321, estimates the U.S. Census Bureau.

    See the Zillow Home Value Index for Munsey Park, N.Y.

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  16. No. 36 Most Expensive Small Town: Chevy Chase Village, Md.
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    No. 36 Most Expensive Small Town: Chevy Chase Village, Md.

    Median home value: $1,234,594
    YOY price change: -5.9%
    Population: 2,060
    2010 Rank: 41

    Chevy Chase Village, known for its Victorian-style homes, is one of the country's wealthiest communities: According to U.S. Census Bureau estimates, median household income exceeds $250,000 and per capita income is $157,883. The village is about eight miles from Washington, D.C., and is home to many of the capital's movers and shakers.

    See the Zillow Home Value Index for Chevy Chase Village, Md.

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  17. No. 35 Most Expensive Small Town: Bridgehampton, N.Y.
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    No. 35 Most Expensive Small Town: Bridgehampton, N.Y.

    Median home value: $1,240,591
    YOY price change: -7.5%
    Population: 1,482
    2010 Rank: 8

    About 100 miles from Manhattan, the exclusive town of Bridgehampton has some of the country's most expensive homes for sale. It is a popular vacation town in the heart of the Hamptons, and the population increases during the summer (65.7 percent of housing units are vacant, according to the U.S. Census Bureau). Bridgehampton is also home to the Hampton Classic equestrian riding event, the Atlantic Golf Club, the Bridgehampton Antique Car Road Rally, and the Bridgehampton Chamber Music Festival.

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

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  18. No. 34 Most Expensive Small Town: Medina, Wash.
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    No. 34 Most Expensive Small Town: Medina, Wash.

    Median home value: $1,257,153
    YOY price change: -7.2%
    Population: 3,041
    2010 Rank: 36

    Medina, the exclusive suburb where Bill Gates' waterfront home (pictured) is located, borders Lake Washington and the expensive suburb of Clyde Hill. It has 26.7 acres of parkland, including Medina Beach Park, and popular outdoor activities include golf, bicycling, hiking, backpacking, boating, sailing, and kayaking, according to northwestjournalonline.com. The area belongs to the Bellevue School District.

    See the Zillow Home Value Index for Medina, Wash.

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  19. No. 33 Most Expensive Small Town: Spring Lake, N.J.
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    No. 33 Most Expensive Small Town: Spring Lake, N.J.

    Median home value: $1,259,716
    YOY price change: -5.6%
    Population: 3,862
    2010 Rank: 45

    Spring Lake, a seaside town in central New Jersey's Monmouth County, has the state's longest noncommercial boardwalk and two miles of beach. Highlights include old, Victorian-style mansions, shopping and dining amenities, and several nearby golf courses. Spring Lake is a year-round community, but it also attracts many summer visitors and Census data show that 31.4 percent of housing units are vacant.

    See the Zillow Home Value Index for Spring Lake, N.J.
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  20. No. 32 Most Expensive Small Town: Kentfield, Calif.
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    No. 32 Most Expensive Small Town: Kentfield, Calif.

    Median home value: $1,285,855
    YOY price change: +2.2%
    Population: 6,348
    2010 Rank: 44

    Kentfield, 15 miles north of San Francisco, is one of the rainiest parts of the Bay Area, receiving about 48 inches of precipitation each year, according to data from the Western Regional Climate Center. Still, the high-end homes, highly regarded Kentfield School District, and nearby parks make the place attractive to residents. Kentfield is home to one of College of Marin's campuses.

    See the Zillow Home Value Index for Kentfield, Calif.

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  21. No. 31 Most Expensive Small Town: Sea Girt, N.J.
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    No. 31 Most Expensive Small Town: Sea Girt, N.J.

    Median home value: $1,311,368
    YOY price change: -6.1%
    Population: 2,116
    2010 Rank: 40

    The boardwalk and beaches in Sea Girt, a coastal community near expensive New Jersey town Spring Lake, attract many vacationers. It is also home to a historic lighthouse that opened in 1896. The town is served by the Sea Girt Elementary School, the Brookside School, and Manasquan High School, according to the borough website.

    See the Zillow Home Value Index for Sea Girt, N.J.
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  22. No. 30 Most Expensive Small Town: Saddle River, N.J.
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    No. 30 Most Expensive Small Town: Saddle River, N.J.

    Median home value: $1,317,400
    YOY price change: -9.3%
    Population: 3,197
    2010 Rank: 26

    Saddle River, in northern New Jersey near the New York border, has been home to President Richard Nixon (1981 to 1990) and hip-hop mogul Russell Simmons. One of the town's major recreation facilities is Rindlaub Park, which has baseball diamonds, tennis courts, a nature trail, playground, and summer concerts.

    See the Zillow Home Value Index for Saddle River, N.J.
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  23. No. 29 Most Expensive Small Town: Yarrow Point, Wash.
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    No. 29 Most Expensive Small Town: Yarrow Point, Wash.

    Median home value: $1,337,207
    YOY price change: -2.2%
    Population: 997
    2010 Rank: 38

    Yarrow Point, a half-crescent peninsula that covers about 231 acres, is bordered on three sides by the eastern shoreline of Lake Washington. It is near expensive towns Clyde Hill and Medina. One attraction is the Wetherill Nature Preserve, between Yarrow Point and Hunts Point, which has walking trails and is popular for bird watching, according to the town's website.

    See the Zillow Home Value Index for Yarrow Point, Wash.

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  24. No. 28 Most Expensive Small Town: Chilmark, Mass.
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    No. 28 Most Expensive Small Town: Chilmark, Mass.

    Median home value: $1,357,917
    YOY price change: -6.1%
    Population: 953
    2010 Rank: NA

    Chilmark, a rural beach town on the western end of the island of Martha's Vineyard, has many vacation properties and seasonal visitors. A fishing village in Chilmark called Menemsha has a small yacht marina and a commercial pier where fishing vessels tie up. In August 2010, President Barack Obama and his family vacationed there, renting Blue Heron Farm.

    See the Zillow Home Value Index for Chilmark, Mass.

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  25. No. 27 Most Expensive Small Town: Stinson Beach, Calif.
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    No. 27 Most Expensive Small Town: Stinson Beach, Calif.

    Median home value: $1,364,180
    YOY price change: +6.0%
    Population: 751
    2010 Rank: NA

    A beach town 20 miles north of San Francisco, Stinson Beach is located along a scenic shoreline route on Highway One. Residents have many options for outdoor recreation nearby, including Stinson Beach Bolinas Lagoon Preserve, Mt. Tamalpais State Park, Muir Woods, Red Rock Beach, and Marin Headlands, according to the town's website.

    See the Zillow Home Value Index for Stinson Beach, Calif.
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  26. No. 26 Most Expensive Small Town: Lloyd Harbor, N.Y.
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    No. 26 Most Expensive Small Town: Lloyd Harbor, N.Y.

    Median home value: $1,400,535
    YOY price change: -12.9%
    Population: 3,760
    2010 Rank: 20

    Many homes in the North Shore's Lloyd Harbor have water vistas and private docks, according to pipingrockrealestate.com. Residents can access fields, rocky coastal areas, woods, and miles of hiking, biking, and equestrian trails in Caumsett State Historic Park. Lloyd Harbor has been home to aviator Charles Lindbergh, talk show host Sean Hannity, and musician Billy Joel. Median household income is $221,667, according to U.S. Census data.

    See the Zillow Home Value Index for Lloyd Harbor, N.Y.

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  27. No. 25 Most Expensive Small Town: Tiburon, Calif.
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    No. 25 Most Expensive Small Town: Tiburon, Calif.

    Median home value: $1,400,603
    YOY price change: -7.3%
    Population: 8,707
    2010 Rank: 27

    Tiburon, north of San Francisco near the expensive town of Belvedere, is a commuter town and popular destination for visitors. It has marinas, yacht clubs, tennis courts, and swimming facilities, according to goodlifemarin.com. Opportunities for outdoor activity and observing wildlife are available through Tiburon Uplands Nature Preserve and Richardson Bay Audubon Center and Sanctuary.

    See the Zillow Home Value Index for Tiburon, Calif.

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  28. No. 24 Most Expensive Small Town: Laurel Hollow, N.Y.
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    No. 24 Most Expensive Small Town: Laurel Hollow, N.Y.

    Median home value: $1,401,126
    YOY price change: -0.2%
    Population: 1,923
    2010 Rank: 37

    Louis Comfort Tiffany, the stained-glass artisan who later became design director for Tiffany & Co., was among the first wealthy New Yorkers to move to Laurel Hollow in the early 1900s. The village, about 30 miles from Manhattan, is hilly and offers views of the harbor. The posh community is home to Cold Spring Harbor Laboratory, a nonprofit with research programs focusing on cancer, neurobiology, plant genetics, genomics, and bioinformatics.

    See the Zillow Home Value Index for Laurel Hollow, N.Y.
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  29. No. 23 Most Expensive Small Town: Amagansett, N.Y.
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    No. 23 Most Expensive Small Town: Amagansett, N.Y.

    Median home value: $1,419,438
    YOY price change: -14.5%
    Population: 1,164
    2010 Rank: NA

    An East Hampton beach town about 100 miles from Manhattan, Amagansett offers access to nearby sporting facilities, a golf club, fishing, sailing, and biking. The resort location also has a village square with restaurants and shops. It has been home to musician Paul McCartney, comedian Jerry Seinfeld, and actress Gwyneth Paltrow.

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

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  30. No. 22 Most Expensive Small Town: Muttontown, N.Y.
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    No. 22 Most Expensive Small Town: Muttontown, N.Y.

    Median home value: $1,425,461
    YOY price change: -1.2%
    Population: 3,413
    2010 Rank: 34

    A village in Oyster Bay about 30 miles from Manhattan, Muttontown was originally settled in the 1600s and primarily served as an area for sheep grazing. Today it is well-known for large estates, nature preserves, and miles of horse trails. Celebrities such as musician Alicia Keys and former Jets quarterback Chad Pennington have lived in Muttontown. With a median household income above $250,000, it is one of the wealthiest towns in the U.S.

    See the Zillow Home Value Index for Muttontown, N.Y.
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  31. No. 21 Most Expensive Small Town: Plandome, N.Y.
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    No. 21 Most Expensive Small Town: Plandome, N.Y.

    Median home value: $1,530,309
    YOY price change: +4.8%
    Population: 1,264
    2010 Rank: 33

    The wealthy village of Plandome in North Hempstead is about 20 miles east of Manhattan and accessible by mass transit. One of the area's attractions is the Plandome Country Club, which offers golf, swimming, and dining. The Census Bureau estimates median household income is $241,667.

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

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  32. No. 20 Most Expensive Small Town: Oyster Bay Cove, N.Y.
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    No. 20 Most Expensive Small Town: Oyster Bay Cove, N.Y.

    Median home value: $1,533,168
    YOY price change: -0.3%
    Population: 2,252
    2010 Rank: 28

    Although Oyster Bay Cove is one of the wealthiest towns in the country, with median household income above $250,000, according to the Census Bureau, the area is known to be less glitzy than the nearby Hamptons. The village, which covers 4.3 square miles, has been home to President Theodore Roosevelt, former Jets quarterback Vinny Testaverde, fashion designer Oleg Cassini, and banker Mortimer Schiff (who owned Northwood, once a 900-acre estate).

    See the Zillow Home Value Index for Oyster Bay Cove, N.Y.
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  33. No. 19 Most Expensive Small Town: Upper Brookville, N.Y.
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    No. 19 Most Expensive Small Town: Upper Brookville, N.Y.

    Median home value: $1,560,938
    YOY price change: -2.3%
    Population: 1,826
    2010 Rank: 25

    Long Island's Upper Brookville in Oyster Bay is surrounded by expensive towns Muttontown, Oyster Bay Cove, Old Brookville, and Brookville. It is near the Mill River Club, Muttontown Country Club, and Hoffman Center Nature Preserve and Wildlife Sanctuary.

    See the Zillow Home Value Index for Upper Brookville, N.Y.

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  34. No. 18 Most Expensive Small Town: Monte Sereno, Calif.
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    No. 18 Most Expensive Small Town: Monte Sereno, Calif.

    Median home value: $1,596,355
    YOY price change: -4.4%
    Population: 3,478
    2010 Rank: Unchanged

    Monte Sereno, 10 miles southwest of San Jose and minutes from Silicon Valley, is known for its rural atmosphere, wooded hillsides, and large estates, and is home to many Silicon Valley executives. Author John Steinbeck wrote The Grapes of Wrath and Of Mice and Men at a house in the town.

    See the Zillow Home Value Index for Monte Sereno, Calif.
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  35. No. 17 Most Expensive Small Town: Loyola, Calif.
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    No. 17 Most Expensive Small Town: Loyola, Calif.

    Median home value: $1,647,484
    YOY price change: -0.6%
    Population: 3,525
    2010 Rank: 21

    Loyola, near Los Altos Hills and tech centers Mountain View and Cupertino, is a small town that covers about 1.7 square miles. It is near Los Altos Golf and Country Club, as well as other amenities such as public parks and the 3,800-acre Rancho San Antonio Open Space Preserve.

    See the Zillow Home Value Index for Loyola, Calif.
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  36. No. 16 Most Expensive Small Town: Rancho Santa Fe, Calif.
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    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.

    See the Zillow Home Value Index for Rancho Santa Fe, Calif.
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  37. No. 15 Most Expensive Small Town: Old Westbury, N.Y.
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    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.

    See the Zillow Home Value Index for Old Westbury, N.Y.

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

    See the Zillow Home Value Index for Old Brookville, N.Y.

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

    See the Zillow Home Value Index for Quogue, N.Y.
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  40. No. 12 Most Expensive Small Town: Brookville, N.Y.
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    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.

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

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

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

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

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

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

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

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

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

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

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

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

    (Editor's note: This slide has been updated to correct the dimensions of Fair Field.)
    Bloomberg