Housing in Oakland blends historic and small-scale stock with newer construction. The town retains older homes near its original core along Oakland Avenue, alongside more recent single-family development on the surrounding streets. Homesites tend to be more spacious than in denser Orlando suburbs, and the town's lakeside setting and trail access add to its appeal. The market is modest in scale, reflecting Oakland's identity as a compact, historic town rather than a large master-planned community.

Oakland offers a small-town, lakeside pace within the Orlando metro area. Residents enjoy the shade of old oaks, the West Orange Trail for walking and cycling, and access to Lake Apopka's shoreline and wetlands. The historic downtown along Oakland Avenue retains a compact, walkable feel, while Winter Garden's thriving restaurant and shopping scene sits just two miles east. The community's small size and preserved character appeal to those who want a quieter alternative to suburban Orlando while staying close to regional employment, attractions, and services.

Oakland is served by Orange County Public Schools, the district covering the county including the Orlando metro area. The town is also home to Oakland Avenue Charter School, an elementary charter campus that serves local students. Beyond the elementary level, students attend zoned Orange County middle and high schools, and the nearby communities of Winter Garden and Clermont offer additional public and private school options within a short drive.

Oakland sits near State Road 50, the main east–west route through west Orange County, connecting the town to Winter Garden, Ocoee, and the Orlando area. Florida's Turnpike and the Western Beltway (State Road 429) are reachable within a short drive, providing access to the broader Orlando region, the attractions area, and points beyond. The West Orange Trail also provides a non-motorized route to Winter Garden and adjacent communities, making the town unusually walkable and bike-friendly for the region.

The West Orange Trail is Oakland's signature recreational asset, running through town along a former rail corridor and linking it to Winter Garden and the wider trail network of west Orange County. The Oakland Nature Preserve offers boardwalks and trails through Lake Apopka wetlands, with wildlife viewing and environmental programming. Lake Apopka itself provides fishing and scenic shoreline, while Winter Garden's parks, downtown, and lakefront pavilion add to nearby recreation options. The town's compact, walkable streets and shaded canopy make everyday outdoor activity part of local life.