Oleander grows vigorously and requires annual late-winter pruning to maintain a small size and attractive shape. Maintaining a 2-3-foot-tall oleander plant, though, is unrealistic, unless your oleander (Nerium oleander) is a dwarf cultivar, such as 'Petite Salmon' or 'Petite Pink', which top out at 3-4 feet tall. If you trim the plant back to 2-3 feet tall, it will send out new branches just below the cut, leaving the base of the plant bare.

 

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That said, leggy stems indicate that your plant needs corrective pruning. Begin by completely removing one-third of the large, woody stems. Cut the remaining stems back by one-quarter of their height. Late next winter, remove several more of the large, woody stems if necessary, and trim back branches.