Background The purpose of this study is to evaluate the outcome of orbital floor reconstruction with free flaps after maxillectomy. Methods This was a retrospective analysis of 34 consecutive patients who underwent maxillectomy with orbital floor removal for malignancies, reconstructed with free flaps. A cross-sectional survey to assess the functional and esthetic outcome was done in 28 patients who were alive and disease-free, with a minimum of 6 months of follow-up. Results Twenty-six patients had bony reconstruction, and eight had soft tissue reconstruction. Free fibula flap was the commonest flap used (n = 14). Visual acuity was normal in 86%. Eye movements were normal in 92%. Abnormal globe position resulted in nine patients. Esthetic satisfaction was good in 19 patients (68%). Though there was no statistically significant difference in outcome of visual acuity, eye movement, and patient esthetic satisfaction between patients with bony and soft tissue reconstruction, more patients without bony reconstruction had abnormal globe position (p = 0.040). Conclusion Free tissue transfer has improved the results of orbital floor reconstruction after total maxillectomy, preserving the eye. Good functional and esthetic outcome was achieved. Though our study favors a bony orbital reconstruction, a larger study with adequate power and equal distribution of patients among the groups would be needed to determine this. Free fibula flap remains the commonest choice when a bony reconstruction is contemplated.