Highland Park's housing market is defined by historic, architecturally significant single-family homes on generously sized lots. The stock ranges from Spanish Colonial and Tudor Revival homes of the 1920s and 1930s to mid-century moderns, Georgian Revivals, and newer French eclectic and Italianate designs. Streets such as Lakeside Drive in Old Highland Park are among the most prestigious in Dallas, with views over Turtle Creek. The market is mature, low-turnover, and highly sought-after, with homes prized for their character, location, and connection to the town's schools and amenities.

Highland Park's most storied neighborhood is Old Highland Park, the original section of town where Spanish Colonial and Tudor Revival homes line lush, landscaped streets. Lakeside Drive, overlooking Turtle Creek, is widely regarded as one of Dallas's most prestigious residential addresses, with views toward the Dallas Country Club golf course. The town's remaining sections extend north and east toward University Park and Southern Methodist University, blending historic homes with later Georgian Revival and contemporary construction. Together these areas form a cohesive, architecturally rich community rather than a collection of distinct subdivisions.

Highland Park offers an urbane, walkable lifestyle within one of Dallas's most established enclaves. Residents enjoy tree-lined streets, manicured parks, and a close connection to Southern Methodist University and the Katy Trail, while downtown Dallas's dining, arts, and employment centers are minutes away. The town's civic life centers on its schools, parks, and country-club traditions, and its central location gives residents access to the full range of Dallas amenities. Highland Park's lifestyle is defined by architectural character, convenience, and a deep-rooted sense of community identity.

Highland Park is served by the Highland Park Independent School District, which covers the town and neighboring University Park. The district operates multiple elementary and middle school campuses, with all students attending Highland Park High School in University Park. The district is widely regarded for its strong academic performance, extensive extracurricular programs, and community support, and it is a defining factor in the town's desirability. Private schools and Southern Methodist University add to the area's educational landscape.

Highland Park is bordered by two of Dallas's primary north–south corridors, the Dallas North Tollway and U.S. Highway 75 (Central Expressway), providing direct access to downtown Dallas and the northern suburbs. The town's central location keeps commutes short for those working in the Dallas core, Uptown, and the nearby medical and commercial districts. The Katy Trail and local street grid support walking and cycling, while Dallas Love Field and the wider regional highway network are a short drive away.

Recreation in Highland Park centers on Turtle Creek and the town's park system, with landscaped greenways, walking paths, and the Dallas Country Club anchoring the local landscape. The Katy Trail, a popular urban rail-trail, runs nearby through the Dallas core, and Southern Methodist University brings cultural and athletic events to the area. Downtown Dallas's museums, arts district, and professional sports venues are minutes away. The town's own parks and tree-lined streets provide everyday outdoor space, while regional parks and lakes extend recreation options across the metroplex.