Anacortes' housing stock reflects its century-plus history and waterfront setting. Older craftsman and Victorian-era homes cluster near downtown and the marina, while mid-century and newer single-family homes spread across hillside neighborhoods, many positioned to capture views of the water and the San Juan Islands. Condominiums and townhomes appear near the waterfront and in select developments, adding options for smaller households. The market is characterized by a premium on water and mountain views, with homes ranging from modest in-town bungalows to larger custom properties. As a gateway community, Anacortes attracts both year-round residents and buyers seeking vacation or retirement homes in a scenic coastal setting.

Anacortes' neighborhoods follow the island's topography and waterfront. The historic Old Town district near Cap Sante Marina holds the city's oldest homes and its walkable commercial core, while areas around Washington Park and Skyline rise to overlook the water and the San Juans. The Oakes Avenue corridor and surrounding residential streets offer a mix of established homes within walking distance of downtown. Fidalgo Island's western and northern edges include forested and waterfront parcels, and the nearby Anacortes Community Forest Lands preserve extensive public acreage within the city limits. Each area shares the city's defining feature: proximity to the water and easy access to marinas, parks, and trail networks.

Anacortes combines a working maritime culture with an outdoors-oriented lifestyle. The downtown waterfront centers on Cap Sante Marina, where boaters, anglers, and visitors mix with shops and restaurants, while the city's arts scene, galleries, and community events add a cultural dimension. Ferry travel to the San Juan Islands is a routine part of life, and kayaking, sailing, crabbing, and fishing are common pursuits. The surrounding forest lands and Deception Pass State Park support hiking, mountain biking, and wildlife viewing. Major employers include the Marathon-Anacortes Refinery and the Port of Anacortes, grounding the community in marine and industrial trades alongside its tourism economy.

Anacortes is served by the Anacortes School District, one of the city's larger employers, operating a set of elementary, middle, and high schools for the Fidalgo Island community. The district serves the city and surrounding island areas, offering standard academic, athletic, and arts programs within a small-district setting. Skagit Valley College, with a main campus in nearby Mount Vernon, provides higher education and workforce training opportunities for area residents. For families, Anacortes' schools combine the intimacy of a smaller system with access to the broader Skagit County educational and community resources.

Anacortes is a regional transportation anchor because of its Washington State Ferries terminal, which connects the mainland to Lopez, Orcas, Shaw, and San Juan islands and to Sidney, British Columbia. State Route 20, the North Cascades Highway, links Fidalgo Island to Interstate 5 and Mount Vernon, and continues east across the Cascades. The city's marinas serve recreational and commercial boat traffic, and a deep-water port supports marine industries. Seattle-Tacoma International Airport is reachable by shuttle or car, and nearby Skagit Regional Airport serves general aviation. Most local travel is by car, reflecting the island's spread-out, scenic road network.

Anacortes' recreation is shaped by its coastal and forest setting. Cap Sante Park, a 37-acre forested promontory at the eastern edge of the city, offers sweeping views over the marina, Fidalgo Bay, and the Cascades, while Washington Park provides a scenic loop road and shoreline access. The Anacortes Community Forest Lands preserve thousands of acres of trails for hiking, mountain biking, and wildlife viewing within the city. Deception Pass State Park, at the island's southern tip, offers beaches, camping, and iconic bridge viewpoints, and the San Juan Islands and North Cascades National Park lie within day-trip range for boating, paddling, and alpine recreation.