Crestline's housing stock is defined by its mountain setting: rustic cabins, A-frame homes, and cedar-sided retreats on small forested lots, plus lakefront and lake-view properties near Lake Gregory. Many homes began as vacation cabins and have been expanded or modernized for full-time living, and the community includes a mix of weekend retreats, vacation rentals, and year-round residences with forest and ridgeline views. Valley of Enchantment, a well-known neighborhood pocket, features cozy, compact homes on relatively modest lots. Because Crestline sits closer to the base of the mountains than Lake Arrowhead or Big Bear, it has historically offered a more accessible entry point to San Bernardino Mountain ownership, a key part of its market character.

Crestline's neighborhoods cluster around Lake Gregory and the Lake Gregory Boulevard corridor. Historic Old Town Crestline, reached via State Route 138, is the community's original commercial core, with antique and hometown shops and the village atmosphere of the Lake Gregory Boulevard hub. The Valley of Enchantment neighborhood lies in a tree-filled pocket east of the lake, known for its compact cabins and cozy lots. Lakeside areas wrap around Lake Gregory's shoreline, while hillside and ridgeline parcels offer broader views of the forest. Because Crestline is unincorporated, neighborhoods blend into the surrounding San Bernardino National Forest, giving the community a dispersed, woodsy layout rather than a single downtown center.

Crestline offers a four-season mountain lifestyle unusual in Southern California: pine and cedar forests, cool summers at the lake, and occasional winter snow that transforms the ridges. Lake Gregory anchors warm-weather life with swimming, boating, and fishing, while Old Town Crestline supplies the small-town social fabric—antique shops, hometown stores, a farmers market, and live music during the summer months. The economy is tourism-driven, so the pace quickens on weekends and holidays and settles into quiet in the off-season. Residents tend to value the clean air, forested views, and a slower, family-oriented rhythm, with the Inland Empire's job centers reachable down the mountain for commuters.

Crestline is served by the Rim of the World Unified School District, which also covers the neighboring mountain communities of Lake Arrowhead and Running Springs and nearly all of the Crestline area. The district operates elementary schools, including Valley of Enchantment Elementary, along with a middle and high school serving the broader mountain region. Because the district spans a dispersed, mountainous territory, busing and mountain road travel are part of the school routine, and families should consider weather-related closures in winter. The district's name reflects the surrounding Rim of the World scenic highway corridor that ties these San Bernardino Mountain communities together.

Crestline is reached primarily via State Route 18, the Rim of the World Highway, which climbs from San Bernardino through the mountains as a scenic, sometimes winding route; State Route 138 then branches into Crestline and Old Town. Its position near the base of the range makes it one of the most accessible mountain towns in the San Bernardino Mountains, closer than Lake Arrowhead and Big Bear. Driving is essential, and mountain conditions—snow, ice, and chain controls in winter—can affect travel times down to the Inland Empire. The community is well positioned for weekend and seasonal use as well as full-time living, but commuters should account for elevation and weather on the descent.

Lake Gregory is the heart of recreation in Crestline. The 84-acre lake offers swimming, fishing, kayaking, and paddle boarding, along with San Bernardino County's inflatable waterpark and waterslides in summer, all framed by pine forest and lakeside picnic grounds. The surrounding San Bernardino National Forest adds hiking, mountain biking, and scenic drives along the Rim of the World Highway. Historic Old Town Crestline provides a walkable cluster of shops and gathering spots, and seasonal events—from summer farmers markets and live music to winter snow play—round out the calendar. The lake's public, family-oriented character has been central to the community since its creation in the late 1930s.