At the Wintergreen Resort, you can ski and play golf, sometimes on the same day.  Located in Nellysford, VA, about 35 minutes from Charlottesville, Wintergreen is one of those hybrid resort/residential communities where the transient and permanent exist in peaceful harmony. 
    At 11,000 acres, Wintergreen is huge, with mountain real estate accounting for about 2,000 acres and the Stoney Creek community in the valley below sitting on 3,000 acres.  The rest will remain natural forever thanks to an arrangement in 1994 between Wintergreen’s owners and the Wintergreen Development Company.  The result, the Wintergreen Nature Foundation, maintains a full-time staff of six, supplemented by many volunteers from Wintergreen.  The Foundation promotes a wide range of activities, including wildflower reseeding efforts, workshops and nature walks on the community’s 30 miles of marked trails, some of which link directly to The Appalachian Trail.  Mountain bikers have use of 24 separate trails, mostly near the ski slopes.100_1990
    At Wintergreen, the core recreation activities are skiing and golf.  Wintergreen’s mountain top area is warm and inviting, with a Euro-village style lodge just steps from the resort’s 24 slopes, more than half of them lighted, and from the clubhouse and pro shop for Devil’s Knob, an Ellis Maples 18 hole layout that inspires awe, some fear and a little loathing.  Opened in 1977, the course provides the views you’d expect from a mountaintop, but some crazy rolls and cliff hanging lies as well.  Many local golfers prefer the two original nines of the 27 holes at the Stoney Creek course at the bottom of the mountain, which is open year round.  It is not uncommon in January and February for Wintergreen’s hardiest sportsmen and women to ski in the morning and play golf in the afternoon.
    The Shamokin and Tuckahoe nines at Stoney Creek are the combination most favored by members.  Rees Jones laid out the Shamokin and Monaccan nines in 1988 and added the Tuckhoe 10 years later.  The routing is clear and without surprise, with only one or two blind shots from the tees and no gussied-up landscaping.  The greens, which are well trapped, roll fast and true with many undulations, yet we didn’t scratch our heads once over a misread break. The first hole on the Tuckahoe nine starts from a dramatically elevated tee to a generous fairway framed by traps on the right and a huge lake at greenside right.  It forms a beautiful and intimidating tableau from the tee box.  A decade ago, Golf Digest named Stoney Creek one of the top 50 resort courses in the U.S.
    With a grand smorgasbord of activities at Wintergreen, the community offers a dizzying array of membership plans.  A fee of $17,000, 80% of it refundable when a membership is resigned and reissued, opens up the resort’s amenities on a “cafeteria-style” basis that includes not only golf, but also tennis, skiing, fitness centers, pools and access to the community lake.  For example, you can buy unlimited golf for $4,000 annually, or unlimited golf, tennis and snow sports for $4,350, a bargain.
    Housing options are high and low in Wintergreen in terms of both altitude and price, with nice golf course lots in the ½ to ¾ acre range for under $200,000.  Count on an average of about $175 per square foot in construction costs.  A few of the most expensive homes, some with impressive views, top $1 million but the median price is close to $600,000.  Town homes rarely exceed $500,000, but a new top-of-mountain luxury building, called The Summit, will provide large condos and spectacular views for around $1 million.
    Life at some remove from a sizeable town (Wintergreen is 40 minutes from Charlottesville) demands a few modest accommodations.  At 15 miles, it can seem a long way to a supermarket, and some Wintergreen residents take coolers on their weekly grocery expeditions.  And although Wintergreen’s residents and resort guests co-exist quite peacefully, the full-timers tend to arrange their recreation schedules accordingly, opting to play golf and ski on weekdays rather than the more heavily trafficked weekends.  Given the incredible amount and variation of the natural land in Wintergreen, its residents are more than happy on weekends to take a hike.

Bottom Line:  Wintergreen’s residents share the community’s ample number of amenities and 6,000 acres of unsullied natural space with more than 100,000 resort guests a year, yet there is plenty of room for all.  If you don’t require the cosseted life of a private country club community, Wintergreen’s range of year-round activities, fine variety of golf courses, reasonable real estate prices and beautiful views could put you on permanent vacation.

    Today the golf course view.  Tomorrow the woods.  That could be the fate for some in the U.S. northeast, midwest and elsewhere who want to move south in the next few years but are determined to ride out the current real estate slalom and hang onto their primary homes.   
    PMI, the Private Mortgage Insurance Company, knows something about risk, and every year the company publishes a “risk index” which sizes up the potential for decline in major housing markets.  The latest index was released in late January.  Not surprisingly, the riskiest markets are on the west coast, with Sacramento leading the way with a 60.4% risk of declining home values.  The riskiest non-California market is the Nassau-Suffolk Counties area of Long Island, with a 60% risk factor.  Contrast that with the Charlotte, NC, area with a 9% decline potential, or San Antonio with a 7.5% risk.  That’s quite a spread for those considering moving south in a few years, and maybe it argues for taking your lumps now rather than later.
    Financial advisors are always preaching about conservative portfolios of investments as you approach or enter retirement.  The mantra is to reduce your risk, and being of a certain age ourselves, we can’t argue with that.  But it seems the same advice might apply to housing, no?
    Consider this.  Your home on Long Island (or wherever) is not appreciating and isn’t likely to for the next few years, according to many sources.  That gated golf community you’ve had your eye on in the Charleston area is appreciating at close to 10% annually and seems likely to continue to do so as more and more baby boomers head south.  How much risk do you want to take that next year your primary home may appreciate enough to keep up with the appreciation of the house you want to buy in a few years down south?  And if you are still waiting five years from now, will you have to settle for, say, a wooded view rather than a lake view?
    For the adventuresome, housing futures, which trade pretty much like stock market futures, may be an intermediate strategy, especially if you live in one of the 10 markets you can bet on (or against).  For more information, a simple Google search by the term "housing futures" will provide some information.
    In the spirit of full disclosure, we own shelter in Connecticut and, with one child three years from college, we have a convenient excuse not to take our own advice.  Out of impetuous dumb luck, we bought a condo near the coast in South Carolina seven years ago.  So we have some yang to go with the yin of a soft market in the Hartford area.  But three years from now, as empty nesters, the view from here will be very different.