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The Most Expensive Small Towns in America
By Manuel Baigorri and Amanda Zusman
From exclusive summer resorts to elite enclaves, here are communities where the values may be small-town but the valuations remain big
Editor's note: The results of this list were determined by locating the towns in the U.S. with the highest median home sale prices and the smallest year-round population per Metropolitan Statistical Area. All data provided by Zillow.com

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Chilmark, Mass.
Boston-Cambridge-Quincy MA-NH MSA
Median home sale price: $2,237,000
Population: 953
Median household income: $41,197
Located on the island of Marthas Vineyard, Chilmark is the second-least densely populated town in Massachusetts and much more low-key than Edgartown or Oak Bluffs. The town includes the picturesque, 300-year-old fishing village of Menemsha, as well as two private beaches, Squibnocket and Lucy Vincent. Great fishing, kayaking, swimming, and sunsets.
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Stinson Beach, Calif.
San Francisco-Oakland-Fremont, CA MSA
Median home sale price: $1,651,041
Population: 780
Median household income: $87,679
Stinson Beach is known for being a prime surfing location with its long shore. It is located about 30 minutes from the Golden Gate Bridge and is a popular day trip for San Franciscans.
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Water Mill, N.Y.
New York-Northern New Jersey-Long Island, NY-NJ-PA MSA
Median home sales price: $2,488,987
Population: 1,872
Median household income: $84,400
Settled in 1644 on the east end of New Yorks Long Island, Water Mill may be part of the town of Southampton but it lacks its neighbors snooty airs and prides itself on being more laid back, if not more expensive. While it may not be the quaint little village it had once been, it still boasts one of the best farm stands in the areathe Green Thumb, and is only a short bike ride from Flying Point Beach.
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Block Island, R.I.
Providence-New Bedford-Fall River, RI-MA MSA
Median home sale price: $1,486,705
Population: 1,010
Median household income: $48,451
During the winter Block Island, located 13 miles south of the coast of Rhode Island, hunkers down against the biting winds of the Atlantic but in the summer the island blooms. People come here for its pristine beaches, absence of glitz, great biking, and Block Island Race Week, a week-long regatta that attracts sailors from all over.
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Hidden Hills, Calif.
Los Angeles-Long Beach-Santa Ana, CA MSA
Median home sale price: $2,490,163
Population: 2,037
Median household income: $200,000
Hidden Hills is located in Los Angeles County, Calif. Most of the city is taken up by a gated residential community.
Far Hills, N.J.
New York-Northern New Jersey-Long Island, NY-NJ-PA MSA
Median home sales price: $1,071,438
Population: 928
Median household income: $112,817
One of the wealthiest suburbs of Manhattan, Far Hills is notable for its horse farms, rolling hills, elegant mansions, and Old Money. It is also home to several fun attractions, including the Leonard J. Buck Garden, a 33-acre public botanical garden; the Natirar, a 491-acre estate once owned by Mohammed VI, King of Morocco; and the headquarters of the United States Golf Assn.
Sands Point, N.Y.
New York-Northern New Jersey-Long Island, NY-NJ-PA MSA
Median home sales price: $2,226,426
Population: 2,833
Median household income: $200,000
With spectacular views looking over Long Island Sound, Sands Point is Gatsby country. Only a half-hour train ride from Penn Station, this beautiful bedroom community is located at the northernmost point of the Cow Neck Peninsula. Castle Gould, once owned by the Guggenheim family, is one of the local attractions.
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Sullivan's Island, S.C.
Charleston-North Charleston, SC MSA
Median home sales price: $1,302,806
Population: 1,911
Median household income: $92,426
Sullivan's Island is located in Charleston County and has seen its population change by only 0.1 percent in the past eight years.
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Stone Harbor, N.J.
Ocean City, NJ MSA
Median home sales price: $968,209
Population: 1,039
Median household income: $51,471
Stone Harbor thrives as a resort community that can see its population rise to 20,000 during the summer. It shares a barrier island, Seven Mile Island, with its neighbor, Avalon.
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Kenilworth, Ill.
Chicago-Naperville-Joliet, IL-IN-WI MSA
Median home sales price: $1,368,912
Population: 2,422
Median household income: $200,000
Kenilworth has a reputation for being one of the wealthiest communities in the Midwest. It is located approximately 17 miles north of downtown Chicago.
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Rancho Santa Fe, Calif.
San Diego-Carlsbad-San Marcos, CA MSA
Median home sales price: $1,822,094
Population: 3,271
Median household income: $200,000
Rancho Santa Fe is referred to as a bedroom community of San Diego. The town is residential except for one shopping avenue and private schools.
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Clyde Hill, Wash.
Seattle-Tacoma-Bellevue, WA MSA
Median home sales price: $1,466,093
Population: 2,984
Median household income: $132,468
Clyde Hill is located in the Seattle metropolitan area. The city has views of Lake Washington, Mount Rainer, the Olympic Mountains, and the Cascade Mountain range.
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Mount Sereno, Calif.
San Jose-Sunnyvale-Santa Clara, CA MSA
Median home sales price: $1,947,866
Population: 3,533
Median household income: $154,268
Mount Sereno is located in Santa Clara County, Calif. The city is ten miles southwest of San Jose, and it is entirely residential.
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Carmel-by-the-Sea, Calif.
Salinas, CA MSA
Median home sales price: $1,399,939
Population: 3,057
Median household income: $58,163
Carmel-by-the-Sea, commonly referred to as Carmel, is located in Monterey County. It serves as a getaway destination for many Hollywood actors including Clint Eastwood, who served as the towns mayor from 1986 to 1988.
North Chatham, Mass.
Barnstable Town, MA MSA
Median home sales price: $849,705
Population: 1,046
Median household income: $45,519
North Chatham is located near Cape Cod and is home to the Monomoy National Wildlife Refuge.
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Wrightsville Beach, N.C.
Wilmington, NC MSA
Median home sale price: $983,580
Population: 2,577
Median household income: $55,903
Located in the southeast of North Carolina, Wrightsville Beach is known for its beautiful beach cottages. It has warm weather that brings lots of tourists during the summer, and crime is almost nonexistent.
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Haleiwa, Hawaii
Honolulu, HI MSA
Median home sale price: $898,538
Population: 2,226
Median household income: $39,643
This historic town in the North Shore of Hawaii offer great beaches. During the summer, the Haleiwa Arts Festival features art demonstrations and live entertainment.
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Bodega Bay, Calif.
Santa Rosa-Petaluma, CA MSA
Median home sale price: $834,157
Population: 1,518
Median household income: $56,818
A unique town by the sea and only 65 miles north of San Francisco, Bodega Bay is a very good spot for wine aficionados. This gorgeous town is also a really good place for golf and sailing.
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Cabin John, Md.
Washington-Arlington-Alexandria MSA
Median home sale price: $832,742
Population: 1,688
Median household income: $95,695
Cabin John is a historic town of Maryland that is home of the Union Arch Bridge, also know as the Cabin John Bridge, which is the longest single-span arch in the country. This bridge carries the aqueduct that provided Washington, D.C. its first public water.
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Somis, Calif.
Oxnard-Thousand Oaks-Ventura, CA MSA
Median home sale price: $916,525
Population: 2,987
Median household income: $63,043
About an hour car ride north of Los Angeles, this unincorporated area of Ventura County is primarily an agriculture town with a great climate.
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Cayucos, Calif.
San Luis Obispo-Paso Robles, CA MSA
Median home sale price: $798,150
Population: 2,890
Median household income: $42,841
This tiny town of the Central California coast it is a great place for relaxing out of the metropolitan areas. It has great beaches and an incredibly good weather.
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Vail, Colo.
Vail, CO MSA
Median home sale price: $924,040
Population: 4,628
Median household income: $56,680
Located 100 miles west of Denver, Vail is a nice town by the Rocky Mountains with great landscapes and lots of activities for outdoor sports lovers.
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Old Greenwich, Conn.
Bridgeport-Stamford-Norwalk, CT MSA
Median home sale price: $1,323,281
Population: 7,124
Median household income: $99,086
Old Greenwich has been a byword for wealth for generations. Located only 40 miles northeast of Manhattan, it has always been popular with bankers, CEOs and, more recently, hedge fund managers. The local schools are excellent and so are its amenities, which include golf and sailing clubs, the Greenwich symphony orchestra, and the Greenwich choral society.
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Gladwyne, Penn.
Philadelphia-Camden-Wilmington, PA MSA
Median home sale price: $833,071
Population: 4,062
Median household income: $159,905
Considered one of the wealthiest areas in the country, Gladwyne sits 12 outside of Philadelphia along what is known as the Main Line. There are numerous private schools and colleges nearby, as well as hospitals and country clubs.
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Saint Helena, Calif.
Napa, CA MSA
Median home sale price: $890,381
Population: 5,904
Median household income: $58,902
This city is located at the heart of the world famous wine growing Napa Valley, about 65 miles north of San Francisco. The city has become an important business and banking center for the wine industry.
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Waban, Mass.
Boston-Cambridge-Quincy, MA MSA
Median home sale price: $869,945
Population: 5,891
Median household income: $101,001
Waban is one of the 13 villages of Newton in Massachusetts, and is located 10 miles west of Boston. It is a privileged, upscale community with excellent schools and low crime rates.
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Olympic Valley, Calif.
Sacramento-Arden-Arcade-Roseville, CA MSA
Median home sale price: $545, 888
Population: 912
Median household income: $56,875
Commonly known as Squaw Valley, this unincorporated community of Placer County northwest of Tahoe City, is home to the Squaw Valley Ski Resort, which was the location of the 1960 Winter Olympics.
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Santa Ynez, Calif.
Santa Barbara-Santa Maria-Goleta, CA MSA
Median home sale price: $798,258
Population: 4,642
Median household income: $80,284
The village of Santa Ynez, in Santa Barbara County about 130 miles north of Los Angeles, offers numerous art galleries, antique stores, and wine tasting rooms. The village has good weather all year round.
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Isle of Palms, S.C.
Charleston-North Charleston, SC MSA
Median home sale price: $782,822
Population: 4,643
Median household income: $76,170
This Charleston County city offers great beaches and a great golf course to enjoy your vacation.
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Indian Wells, Calif.
Riverside-San Bernardino-Ontario, CA MSA
Median home sale price: $672,465
Population: 5,015
Median household income: $93,986
The city is home of a big number of celebrities and millionaires and it is internationally known for hosting the Indian Wells Masters, one of the nine tournaments in the Tennis Master Series operated by the Association of Tennis Professionals.
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Davidsonville, Md.
Baltimore-Towson, MD MSA
Median home sale price: $701,406
Population: 7,502
Median household income: $61,768
Davidsonville is an unincorporated community located Maryland's central Anne Arundel County. This small rural community is located 25 miles east of Washington, D.C. and about 35 miles south of Baltimore.
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Incline Village, Nev.
Reno-Sparks, NV MSA
Median home sale price: $657,352
Population: 9,639
Median household income: $69,447
Located in Washoe County on the north shore of Lake Tahoe, Incline Village is also home of Sierra Nevada Colleges main campus.
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Incline Village, Nev.
Reno-Sparks, NV MSA
Median home sale price: $657,352
Population: 9,639
Median household income: $69,447
Located in Washoe County on the north shore of Lake Tahoe, Incline Village is also home of Sierra Nevada Colleges main campus.
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