Freeway “deconstruction” marks an abrupt shift in urban policy. Priorities are shifting away from designing cities to enhance mobility toward promoting economic and environmental sustainability, livability, and social equity. This paper investigates the neighborhood, traffic, and housing price impacts of replacing elevated freeways with surface boulevards in two notable yet different corridors of San Francisco: Embarcadero along the city’s eastern waterfront and Central Freeway/Octavia Boulevard serving a predominantly residential neighborhood west of downtown. A combination of informant interviews, literature reviews, and statistical analyses are used in examining neighborhood, traffic, and housing impacts of these two roadway conversions. The research shows freeway conversions generally lead to gentrification of once-declining neighborhoods, although public policies like affordable housing mandates can temper displacement effects. In general, operational and improvements to surface streets along with enhanced transit services and walking environments have accommodated considerable shares of former freeway traffic so as to avoid the traffic nightmares that were predicted when grade-separated freeways were removed. Empirical evidence on residential sales transactions reveals that the dis-amenity effects of proximity to a freeway have for the most part given way to amenity benefits once roadways are converted to nicely landscaped multi-way boulevards. We conclude that freeway-toboulevard conversions, a form of urban re-prioritization that gives more emphasis to neighborhood quality and less to automobility, have yielded net positive benefits without seriously sacrificing transportation performance.