(1) Background: Prolonged lockdowns with stay-at-home orders have been introduced in many countries since the outbreak of the COVID-19 pandemic. They have caused a drastic change in the everyday lives of people living in urbanized areas, and are considered to contribute to a modified perception of the public space. As research related to the impact of COVID-19 restrictions on mental health and well-being emerges, the associated longitudinal changes of brain hemodynamics in healthy adults remain largely unknown. (2) Methods: this study examined the hemodynamic activation patterns of the prefrontal and occipital cortices of 12 participants (5 male, Mage = 47.80, SDage = 17.79, range 25 to 74, and 7 female, Mage = 39.00, SDage = 18.18, range 21 to 65) passively viewing videos from three urban sites in Singapore (Urban Park, Neighborhood Landscape and City Center) at two different time points—T1, before the COVID-19 pandemic and T2, soon after the lockdown was over. (3) Results: We observed a significant and marginally significant decrease in average oxyhemoglobin (Oxy-Hb) over time for each of the visual conditions. For both green spaces (Urban Park and Neighborhood Landscape), the decrease was in the visual cortex, while for the City Center with no green elements, the marginal decrease was observed in the visual cortex and the frontal eye fields. (4) Conclusions: The results suggest that the COVID-19-related lockdown experienced by urban inhabitants may have contributed to decreased brain hemodynamics, which are further related to a heightened risk of mental health disorders, such as depression or a decline in cognitive functions. Moreover, the busy City Center scenes induced a hemodynamic pattern associated with stress and anxiety, while urban green spaces did not cause such an effect. Urban green scenes can be an important factor to offset the negative neuropsychological impact of busy urban environments post-pandemic.