Background: early marriages and teenage pregnancies affect the quality of life of girls preventing them obtaining higher educational qualifications and having better occupational opportunities. Objectives: To study the characteristics of teenage pregnancies and their related outcomes of estate population in Rathnapura district, Sri Lanka. Materials & Methods: Community based descriptive study was conducted among 346 estate women in Rathnapura district in the Sabaragamuwa province in Sri Lanka who conceived within the year 2015 selected by cluster sampling technique. Data were collected by trained health volunteers using an interviewer administered questionnaire. Rate of teenage pregnancies was expressed in percentage with its 95% confidence interval. Characteristics of teenage mothers were assessed in percentages. Pregnancy outcomes between teen and non teen mothers were assessed using chi-square test with calculation of p values for statistical significance. Results: Rate of teenage pregnancies was 10.1% (95% CI=7.7, 12.52). Of them 22.9% were below 18 years. Total of 12 women (38.7%) were not legally married while only 11 non teen women were not legally married. Among these 31 teenage pregnant mothers, 3 were pregnant for the second time while only one had a living child. Previous pregnancies of other two mothers had gotten aborted spontaneously. Out of all teenage pregnancies, 20 (64.5%) were unplanned while only 3 out of 31 (9.6%) have used family planning in their lives. The main stated reason for not using a family planning method was that they did not know about family planning methods (65%) while 20% reasoned as non availability of modern family planning methods closer to them. Among pregnancy outcomes, statistical association could be observed for encountering problems in breastfeeding within first 48 hours of delivery (χ2=6.652; p=0.009), for satisfactory weight gain within first month (χ2=6.71; p=0.009) and mother starting modern family planning method at six weeks after delivery (χ2=7.2603; p=0.007). Statistical association could not be observed between outcome of pregnancy (χ2=2.61; p=0.10), birth weight (χ2=3.672; p=0.055), starting breastfeeding within one hour of delivery (χ2=0.0024; p=0.961) and newborn getting complications within 48 hours of delivery (χ2=1.369; p=0.237). Conclusions: High rate of teenage pregnancies with poor outcomes in the estate population requires identification of risk factors to improve their health status as well as socioeconomic status.