Rolex prices have been soaring for the last 20+ years.  Rolex investments have had the opportunity to pay off nicely for the Rolex owner with some skill and negotiation.  

Not every Rolex investment will generate a positive gain.  

Although every Rolex has value, not every Rolex has the same value to collectors and investors.  The Rolex Daytona is highly sought after, but shines like a bright star over less sought after Rolex watches.  For example, the Milgauss or even the standard Oyster Date-Just will not fetch much attention by investors.  And therefore their prices have sagged to much lower levels.  

Rolexes Hold Their Value But Can Drop From the Original Price.

One of the greatest things about Rolex is the ability for them to hold their value.  Especially well cared for timepieces, can still appear new, and retain their value.  Unlike a car that depreciates quickly, a Rolex will not depreciate as fast.  And over time, a vintage Rolex can start rising in price.

• Seek the Help of Professionals - Watch Collectors know what is hot in the market.  They know what to look for in order for an investment to rise in price.  They know for instance, whether it is better to own a Submariner with or without the date, or whether a steel case is better than a gold one.  They know how rare a timepiece is by the amount of components that are produced each year of that model.  They also know what things collectors and the market in general are looking for.  Just as you would look to a quality broker to recommend a stock, looking at a professional for watch investment advice is critical.
• Take Care of Your Rolex - Make sure you clean and maintain your Rolex.  It is important to know that you are not only looking to make the timepiece last for you, but also for its future owner - whether that be to someone you sell it to, or gift it to.  
• Let Rolex Service The Timepiece - Vintage timepieces may not need to be serviced as frequently.  However, new timepieces can increase in value if you prove that it has been serviced recently and often by Rolex Certified Professionals.  

Avoid these Rolex Traps When Investing in Rolex

• It isn't all about the bling - Some Rolex timepieces are encrusted with an endless supply of diamonds and other gems.  However, collectors don't value the timepiece based on the number of dimonds.  In fact, all-steel Rolexes may rise in value faster than a timepiece worthy of a Rap Artist.
• Pay Attention to the Price - One of the best ways to make a positive investment is to get a quality price.  You can win just by buying when there is a discount.  Basically if you bought a Rolex Daytona when nobody was buying them in the 1960's and 1970's, you would have made a huge profit if you sold it today.  There are many discount vendors who buy wholesale from authorized Rolex Distributors when the price is right.  This means that the 40-50% markup might drop to 10-20%.  So, if you bought at the lower markup, you will have a much better chance at turning a profit.  
• Cheaper Isn't Always Better - Just because a Rolex is cheap, doesn't mean that this is the right one to buy.  It could be cheap because the demand is non-existent.