Endometrial stromal sarcomas (ESS) constitute around 10% of uterine sarcomas, but only 0.2% of all uterine malignancies. ESS usually present in the peri- menopausal age group. ESS are often clinically misdiagnosed as benign entities like uterine leiomyomas and are usually diagnosed postoperatively, after a histopathological examination of a hysterectomy specimen. We report a case series of three cases of endometrial stromal sarcoma, in age group ranging from 28-47 years. Two out of three cases presented with complaints of heavy menstrual bleeding for 6 months and one case with lower abdominal pain for 8 months. Clinico-sonographically, these cases were diagnosed as fibroid. Out of three cases, two cases underwent MRI (abdomen and pelvis) for evaluation, with Smooth Muscle Tumor of Uncertain Malignant Potential (STUMP) and leiomyosarcoma considered as possible differential diagnosis. One patient underwent Myomectomy and later hysterectomy for completion. Two other patients underwent Total Abdominal Hysterectomy with Bilateral Salphingo-oopherectomy. Histopathological examination revealed ESS in all three cases of which two cases were reported as low-grade ESS and one as high-grade ESS. Endometrial stromal neoplasms are rare uterine tumours. They can mimic a variety of benign and malignant neoplasms, making accurate diagnosis challenging. When a singlefibroid exhibits increased vascularity on Ultrasound or MRI, along with signs of hypercellularity and necrosis, the possibility of ESS should be considered. This is crucial for planning the appropriate treatment modality to avoid repeat surgeries.