(FORTUNE Magazine) – It's late afternoon in the hills above the Anderson Valley, and this quiet backwater a few hours north of San Francisco is showing why it has attracted urban deserters of various stripes for at least 40 years. From the deck of the serene, redwood-paneled Japanese pole house that Giovanna Nigro-Chacon shares with her husband, Ernie, the view calms jangled nerves. Live oaks stand tall at the crest of their hilltop perch. Thick redwood groves blanket the ridges rising across the narrow valley. The air is warm and still. Refugees from the Los Angeles TV-news trenches, the Chacons grabbed their 20 undeveloped acres in 1981 for $69,000, built their home from a kit, and moved up permanently eight years later. They've just uncorked a bottle of their "millennium cabernet," a smooth-edged sip they've made from grapes that grow amid the straw-colored hills near their property. Giovanna smiles and repeats a phrase she has uttered before: "They'll have to take me out of here feet first."

It's scenes like this that people picture when they entertain the thought of buying a plot of land: a haven, a hideaway where, like Ted Turner gazing out over herds of bison at one of his Rocky Mountain spreads, they can fill their lungs with clean air and ruminate on the finer things. It's an understandable and powerful urge. But the rural-property market can be a minefield of sorts, fraught with such potential calamities as wells running dry and timber clearcuts ravaging million-dollar views. Hoary legends about investors who exchanged their life savings for Florida marshes and Nevada moonscapes still cast long shadows. So if you're tempted to splurge on your own little swatch of paradise with an eye toward building a vacation getaway or even a primary residence down the line, what do you need to know?

First, be forewarned: Buying undeveloped acreage and letting it sit idle for decades is not something to undertake for investment purposes. "The only reason to buy land in a rural or resort area," says Robert Abalos, a Richmond, Va., attorney and author who markets real estate advice through his website, investinginland.com, "is if you want to build a vacation home or retreat very soon after you buy the land, and know in advance that you will likely lose a ton of money doing so. Vacation homes are notoriously bad investments. Having one is something you do for yourself and your family, not necessarily to make money on. I own a fishing lodge, a beach house, and a cabin in the Blue Ridge Mountains. All have cost me money that I could have better spent on stocks or other real estate. But I wouldn't trade the times I have spent at those places for 50 times their cost."

One reason not to buy land for the future is the difficulty of forecasting that future, says John T. Reed, author of 17 books on real estate investing and editor of the newsletter Real Estate Investor's Monthly (available through johntreed.com). Suppose you buy a plot in the Sierra Nevada foothills in California when you're 40, Reed says. A few years later, your daughter graduates from college, moves to North Carolina's Research Triangle, and begins producing adorable grandchildren. Will you really want to be cloistered 3,000 miles away?

If investing is your goal, Reed recommends buying "something sensible, like another house in your neighborhood that you rent out--something that is essentially a universal donor, highly financeable, highly liquid. The only reason to buy land now [to develop sometime later] is to get on the train for the appreciation that'll occur in between. But you don't need to get on that particular train. Put your money somewhere where there's flexibility, where you know what you're doing." If years later you still covet land in the mountains or wherever, Reed says, buy it with the returns you made investing your money more prudently.

But the lure of virgin property and the prospect of raising a house from scratch, with all the overtones of frontier self-sufficiency, can be powerful. And as more baby-boomers reach the age where they have the means and the inclination to buy a second home or land--typically 47, according to the National Association of Realtors--many will do it. After all, it wasn't a financial adviser who wrote the lyrics to "Don't Fence Me In."

One piece of good news, especially for those worried about real estate bubbles: When it comes to land, there are always plentiful bargains to be had. "The real estate market is not an efficient market like the stock market," says Abalos. "Information is not transmitted immediately, linking buyers and sellers is very tough, and real estate is not a liquid asset like a share of stock is. And of all types of real estate, land is the most illiquid of them all, which means that you can get incredible bargains while the market as a whole, whatever that means, continues to rise." There are many ways to search out bargains, says Abalos, who has written a guide on that very topic. They include buying lots from bankrupt or cash-starved developers, contacting out-of-state owners in resort areas who once intended to build but now just want to unload, and looking into foreclosure auctions. "Everyone wants to buy houses and buildings at foreclosure auctions," Abalos says. "Fewer people want raw land."

Once you find one or more plots that seem promising, that's when the real work should begin. Becoming smitten with a view or a property is the easy part. A smart buyer looks well beyond the obvious. Everyday concerns that urban and suburban dwellers generally ignore, such as water supply and sewage disposal, become make-or-break issues in remote areas. "If you buy a piece of property that has no visible sources of water, you're just gambling with your money," says Les Scher, an attorney in Garberville, Calif., and co-author of Finding & Buying Your Place in the Country. "It's a myth that if you dig deep enough you'll hit water." Buying land without ascertaining the availability of water, he says, "is like buying a car when you don't know if it has an engine in it." Make sure a percolation test, which measures the rate at which water drains through the soil, shows that a septic tank will work on the property. Insist on seeing boundary lines documented by a licensed surveyor. "If you buy property without a survey," Scher says, "you could build your house on somebody else's land. It happens all the time."

It's also important, Scher adds, to find out about any legal entanglements attached to the tract. If the water comes from someone else's land, make sure you have deeded (meaning written and legally guaranteed) water rights. Likewise, if your access road or the path of your planned driveway crosses others' property, you need deeded access from each owner. Get a title report--called an abstract of title in some states--that spells out all documented rights associated with the property as well as any rights others may have to use it (such as water, logging, mining, or grazing access). For instance, don't assume that just because no road crosses your prospective property now, no one has the right to build one someday. Once you obtain any documents mentioned in the title reports, hire a lawyer to review any of them you're not sure about.

The wise land shopper also takes the time to chat up other landowners in the area. "It's far more important to know who your neighbors are in the country than in the city," Scher says. Do they target-shoot all weekend? Ride ear-splitting dirt bikes? Have plans to open a feedlot? "I've got a situation now where a person has 200 stray dogs on their property. It's destroying the peace and enjoyment of all the other people in the area."

Herewith, snapshots of five locations where sizable tracts of acreage are still available and worth the price:

Anderson Valley, California

Even by the standards of coastal California property values--which have crossed over from appalling to perversely amusing--asking prices along Mendocino County's fetchingly rugged shoreline manage to raise the eyebrows of all but the most jaded. Just 45 minutes or so inland along Route 128, though, in the bucolic Anderson Valley, the market is, if not a steal, a notch or two more palatable. One selling point is the valley's soothing environment: steep ridges adorned with live oaks, redwoods, apple orchards, split-rail fences, swimming holes along the Navarro River, and undulating rows of grapevines punctuating a handful of blink-and-miss-it towns. The valley's other claim to fame is a lingering hippie ethos, which surfaces in a distrust of anything corporate and reverence for anything organic, hand-crafted, or otherwise earthy-crunchy.

Makes sense if: You're hoping for a five-acre meadow fringed with trees with a panoramic view, but wouldn't mind settling for a larger tract, carving a home site out of dense redwoods, or otherwise teasing the potential out of a not-quite-perfect plot. And you crave--or at least don't mind--serious isolation.

Why now: Two and a half hours from the Golden Gate; zoning and limited water conspiring to curtail densely commercialized Napa-fication; the Pacific within an hour; and land prices that shock only non-Californians. What's not to like?

Word to the wise: All that vertical relief means a 20-acre tract might have only one or two acres flat enough to do anything on, such as build a house.

Recent listing: Twenty-two acres on a steep ridge west of Philo, thick with towering redwoods and firs, ideal for border-line recluses, $179,000. Mendo Realty, giorealtor.com.

HIPPIE CHIC

ANDERSON VALLEY, CALIF.: 22 acres on a ridge west of Philo, thick with towering redwoods and firs. Soothing environment, hippie ethos, and plenty of solitude; 22 hours from San Francisco. $179,000 giorealtor.com

Eureka Springs, Arkansas

Less than an hour west of this tranquil haven in northwest Arkansas's Ozarks, a boom is well under way. The Fayetteville-Springdale-Rogers corridor is home to the University of Arkansas and corporate titans Wal-Mart and Tyson Foods; the population of northwest Arkansas grew 47% in the 1990s, the sixth-fastest rate in the U.S., and this year the Milken Institute ranked the area No. 1 in the nation for economic performance and job creation. Meanwhile, the old Victorian spa town of Eureka Springs (population 2,200) has yet to see its first traffic light or four-lane highway. Retirees and ex-urbanites are steadily trickling into Carroll County, though, mostly from the Midwest and the South. It's not just the shambling pace that draws them. There are 1,000 miles of shoreline and riverbank for boating, fishing, and swimming on large dam-formed lakes such as Beaver and Table Rock, as well as gorgeous, paddleable stretches of the Kings and Buffalo rivers and lush forests. The four mostly pleasant seasons also feature a spectrum of cultural options: jazz, folk, and blues festivals, fine-arts and writers' colonies, visiting opera companies, and Bible-belt family fare such as a summer-long outdoor Passion play.

Makes sense if: Your SUV has been crowded out of your garage by canoes, mountain bikes, fly rods, and golf clubs.

Why now: Despite an early-1990s price surge, property remains a bargain by resort-area standards--even dipping below $1,000 an acre for those who don't require waterfront or fairway.

Word to the wise: Outside of town, zoning is loose. Find out if any property owners upwind either operate, or dream of starting, a chicken farm.

Recent listing: Forty-two wooded acres on Beaver Lake, complete with private waterfall, $269,500. Little Switzerland Realty, unitedcountry.com.

WOODS, WATER, AND WAL-MART

EUREKA SPRINGS, ARK.: 42 wooded acres on Beaver Lake, complete with private waterfall. Boating, fishing, and swimming. Family fare, culture--and WalMart--nearby. $269,500 unitedcountry.com

Sonoita/Patagonia, Arizona

"I've always thought you sort of had to be a renegade to get to Sonoita and Patagonia," says Marsha Burden, who has sold real estate in this high-elevation outpost near the Mexican border for 25 years. "It can be a real culture shock for some people. 'What do you mean, there are no paved roads?'" A slight exaggeration, but it hints at the reasons people come here: a breathtaking mix of high-desert grasslands, cottonwood-lined creeks, sycamore-shaded canyons, and 70-mile views of the surrounding mountains under sapphire skies. Santa Cruz County's location along a prime migration route draws legions of binocular-toting bird watchers, who make a pilgrimage here to catch glimpses of gray hawks, violet-crowned hummingbirds, and some 300 other species. The elevation, ranging from 4,000 feet to 5,000 feet, moderates summer swelter, with temperatures typically topping out around 90. What cinches the deal for some: Tucson and its airport are only an hour away.

Makes sense if: You're willing to give up suburban conveniences in exchange for space, quiet, and plenty of wildlife--javelinas, bobcats, and pronghorn antelope, to name a few.

Why now: The local real estate market has loped along steadily for decades, avoiding drastic booms and busts. But as increasing numbers of newcomers decide they can live here and commute to Tucson, demand, and prices, are likely to grow.

Word to the wise: Here as much as anywhere, the difference between a dream home-site and an expensive boondoggle is, quite simply, water. Learn everything you can about surrounding owners' wells--how abundant their flow is, how deep the drillers had to probe, and how much they cost.

Recent listing: Almost 13 acres of grassland and oak-studded hills, with underground electric and phone lines and a capped well, just 35 miles from Tucson, $214,000. Marsha Burden and Associates, sonoita-realestate.com.

DESERT GEM

SONOITA/PATAGONIA, ARIZ.: 13 acres of high-desert grassland and oak-studded hills. Bird watcher's delight. Space, quiet, and plenty of bobcats and javelinas. Just 35 miles from Tucson. $214,000 sonoita-realestate.com

Flathead Valley, Montana

A telling fact: A recent report categorized retirement income as one of Flathead County's largest "industries." That helps explain why the county's population grew by more than 25% between 1990 and 2000. Lest anyone panic about overcrowding, though, that means full-time residents now total 75,000--scattered over 5,140 square miles. Tourism is another economic pillar, and it's easy to see why. Kalispell, the regional hub, lies within an hour's drive of Glacier National Park; Flathead Lake, the largest freshwater body west of the Mississippi, with nearly 200 square miles of water surface; two ski mountains; eight golf courses; and more than a million acres of Northern Rockies wilderness. Local preoccupations center around hiking, sailing, skiing, fly-fishing, whitewater rafting, kayaking, wildlife-ogling, and all things equestrian. The weather is what passes for mild at this latitude, with the Continental Divide fending off most arctic blasts from Alberta and the lakes moderating harsh extremes. Whitefish and Big Fork are the most expensive locales; perimeter counties such as Sanders and Lincoln remain less crowded and more affordable.

Makes sense if: You're comfortable knowing that you and your pets are not at the top of the local food chain. Bears, mountain lions, and timber wolves have been known to meander into subdivisions.

Why now: "Ten years ago people said, 'Ooh, are we too late?' " says Dave Heine, who grew up in Kalispell and now sells property with Western Brokers. "And it's just gone up since. I think property values are going to be strong here for a long time."

Word to the wise: Keep in mind that remote locations have their drawbacks. Will you be able to get to your site year-round? Could an ambulance get in after a snowstorm? How long would it take a fire engine to arrive?

Recent listing: Thirty-six acres overlooking Bitterroot Lake and the surrounding hills, with large pines, rock outcrop-pings, and phone and electric lines, $202,416. Prudential Glacier Real Estate, jodybrooks.com.

LIVE LIKE GRIZZLY ADAMS

FLATHEAD VALLEY, MONT.: 36 acres overlooking Bitterroot Lake, with large pines and rock outcroppings. Hiking, sailing, whitewater rafting, kayaking, and fly-fishing nearby. All the bears, mountain lions, and timber wolves you can ogle. $202,416 jodybrooks.com

Novia Scotia, Canada

"If you ask people who live here for directions," says Menno Van Driel, a resident of Halifax, the capital of this maritime province, "you run the chance that they'll take you there." That time-warp amiability, along with a relaxed pace and an unspoiled coastal New England ambiance, help explain why not only Americans but also Europeans, Africans, and Middle Easterners are emigrating at least part-time to this 25,000-square-mile peninsula (a dram smaller than Ireland). In recent decades, rural parts of the province have declined in population. That means, Van Driel says, "you can snap up jewels for a really small price." It can also mean, depending on your preference, lovely stretches of shore lined with granite, sand, or gravel beaches near fishing villages that seem to have been lifted from a vintage postcard. Or lush rolling hills and inland valleys, dotted with farms and vineyards. Or a pied-a-terre in Halifax, where the average price of a house has yet to surpass $100,000 (U.S.).

Makes sense if: You live in the Northeast, just a three-hour ferry ride (from Bar Harbor, Maine) or a 90-minute flight (from Boston) away.

Why now: Though the U.S. dollar has slipped against its northern equivalent in the past year or so, 72 Yankee cents still gets you a buck's worth of Canadian ground.

Word to the wise: U.S. citizens and other non-Canadians can buy property in Nova Scotia with no restrictions, and stay in Canada six months out of the year without seeking any special resident status. But because of transnational differences in issues such as estate planning and taxes, it's crucial to involve an attorney--they're called "solicitors" north of the border--in any real estate transaction.

Recent listing: 25 acres on Rae Island, just 100 yards offshore, cloaked with spruce and hardwoods, with both pebbly beach and near-vertical cliff, and enough draft to anchor a large sailboat (which you'll probably need just to reach the island) three hours east of Halifax, $139,853 (U.S.). Royal LePage Realty, menno.ca.

ISLAND PARADISE

NOVA SCOTIA, CANADA: 25 acres on Rae Island, cloaked with spruce and hardwoods, three hours east of Halifax. Pebbly beach and near-vertical cliff. Coastal New England ambiance and extra pop for U.S. dollar. $139,853 menno.ca