Oakland's housing is characterized by larger, wooded lots and a mix of older lake cottages, expanded mid-century homes, and newer construction. Two lake associations — Ramapo Mountain Lakes and the Ramapo River Reserve — organize a significant portion of the borough's roughly 4,400 homes, offering community amenities and a shared lake-oriented lifestyle. The dominant housing type is the single-family home, often on more land than is typical closer to New York. The borough's low-density, semi-rural character and strong schools make it appealing to families seeking space and a natural setting.

Oakland's residential landscape is anchored by its lake communities. Ramapo Mountain Lakes, with about 1,650 homes across more than forty streets, is the borough's largest neighborhood association, while the Ramapo River Reserve is a newer community of roughly 400 homes. Beyond these, established single-family neighborhoods spread through the wooded hills near the Ramapo River. To the west, the borough approaches the Wanaque Reservoir watershed, and neighboring communities include Franklin Lakes and Wyckoff, giving Oakland a leafy, low-density regional context.

Oakland offers a quiet, outdoor-oriented suburban lifestyle. Residents enjoy lake swimming, boating, and community beaches through the lake associations, and the Ramapo River and surrounding woodlands support fishing and hiking. Local shopping and dining cluster along Ramapo Valley Road, with larger retail in nearby Franklin Lakes, Wayne, and Mahwah. The borough's schools, recreation programs, and lake communities foster a strong neighborhood identity, while commuter buses and highways keep New York City and Bergen County employment within reach for working residents.

Oakland Public Schools serve students in kindergarten through eighth grade at Dogwood Hill, Heights, and Manito elementary schools and Valley Middle School. For grades nine through twelve, Oakland sends students to Indian Hills High School in the Ramapo Indian Hills Regional High School District, which Oakland shares with Franklin Lakes and Wyckoff. The district structure provides small neighborhood elementary schools and a well-regarded regional high school, making Oakland's schools a central draw for families moving to the borough.

Oakland sits at a northern New Jersey crossroads, with Interstate 287 (exits 57 and 58), Route 208, and U.S. Route 202 providing access across Bergen County and toward New York State. Coach USA's Short Line runs commuter buses to the Port Authority Bus Terminal in Manhattan, with limited NJ Transit bus service as well. The borough is primarily car-oriented, but its highway network puts the George Washington Bridge, Bergen County employment centers, and the region's airports within a reasonable drive for commuters.

Oakland's recreation is defined by water and open space. The borough's lake communities offer beaches, swimming, and boating, while the Ramapo River supports fishing and riverside walks. Local parks provide ball fields, playgrounds, and trails, and the Ramapo Mountains to the west offer hiking in the Ramapo Valley and near the Wanaque Reservoir. Residents also reach Ringwood State Park and the larger Highlands trail network within a short drive, making the borough a practical base for year-round outdoor activity.