Objective: We analyzed the obstetric and cardiac characteristics and results of pregnant women with heart disease (HD) and compared their results with those of healthy controls. Methods: In this retrospective single-center case–control study, women with HD attended between 2010 and 2018 were matched at a 1:2 ratio (according to date of delivery, parity, and singleton or twin pregnancy) with controls without heart disease treated in the same referral center. Results: We identified 141 pregnant women with HD, of whom 132 reached 22 weeks of gestation and were paired with 264 healthy controls, for a total of 396 participants and 408 newborns. Most common HDs were congenital HD (53 women), arrhythmia (46), valvular HD (35), and cardiomyopathy (16), having women with more than one coexisting HD. During pregnancy or the puerperium, 19.9% of mothers experienced a major adverse cardiac event (MACE), with 5% requiring intensive care unit (ICU) admission. The rates of cesarean section were 37.1% in the case group and 18.2% in the control group, with an odds ratio (OR) of 2.66 (95% CI = 1.66–4.26, p < 0.001). We also found a higher use of general anesthesia, with an OR of 10.73 (95% CI = 2.32–49.75, p = 0.002); more prolonged hospitalizations, with an OR of 2.91 (95% CI 1.02–8.35, p = 0.023); and a higher incidence of low neonatal weight, with an OR of 1.96 (95% CI 1.09–3.52, p = 0.012). There were no differences between groups in terms of gestational age at delivery; however, we observed greater prematurity in women with HD, without reaching statistical significance. The rate of congenital heart disease among the newborns of mothers with HD was 13.2%. Conclusions: HD increases maternal morbidity during pregnancy and it is associated with higher rates of cesarean section and low birth weight.