Chesapeake City is a charming waterfront town located along the Chesapeake & Delaware Canal in Cecil County. Known for its scenic beauty, 19th-century architecture, and close-knit community, the town blends historic character with small-town appeal. The restored canal-front district features boutiques, restaurants, and inns, creating a lively yet relaxed atmosphere that attracts both residents and visitors.

Info

What to know

Community

Why Homebuyers Choose Wilmington

  • Homebuyers seeking a picturesque waterfront town with historic charm, walkability, and an active yet peaceful lifestyle.

Lifestyle

Take life to the next level

  • Residents enjoy a walkable downtown filled with local shops, waterfront dining, and marinas. Outdoor enthusiasts appreciate the nearby Ben Cardin Recreational Trail, canal cruises, and opportunities for kayaking, fishing, and boating. Chesapeake City also hosts seasonal festivals and events that highlight its strong sense of community and maritime heritage.

Neighborhoods

South Chesapeake City Historic District

Description:
This charming neighborhood makes up the heart of Chesapeake City’s canal-side community. Known for its beautifully preserved 19th-century homes, cobblestone sidewalks, and waterfront views, the district captures the town’s rich maritime heritage while offering modern convenience.

Housing style & price:
Predominantly Victorian, Federal, and Colonial-style homes, many dating back to the mid-1800s and carefully restored. Home prices range from $350K–$750K, with some premium canal-view properties exceeding that.

Advantages:
Walkable to shops, waterfront restaurants, and the Chesapeake & Delaware Canal Trail. A highly desirable location for those who love history and community life.

Considerations:
Historic homes may require additional maintenance or preservation compliance.

Best for:
Buyers seeking a walkable, historic waterfront neighborhood with timeless appeal.

Canal View Estates

Description:
Located just outside the historic downtown, Canal View Estates offers a more suburban, residential setting with spacious lots and newer homes. Residents enjoy quiet streets and beautiful views of the nearby waterway while remaining close to Chesapeake City’s attractions.

Housing style & price:
Mostly modern single-family homes built in the 1990s through early 2000s, featuring open floor plans and large yards. Prices generally range from $400K–$600K.

Advantages:
Peaceful environment, easy access to Route 213, and proximity to marinas, parks, and schools.

Considerations:
Limited dining or retail within immediate walking distance; car travel is typically needed for errands.

Best for:
Families or professionals wanting modern living near Chesapeake City’s waterfront charm.

    Holloway Beach

    Description:
    A quiet residential community located north of town, Holloway Beach provides a relaxed waterfront setting with private docks and access to the canal. It’s ideal for boaters and outdoor enthusiasts who appreciate privacy and scenic views.

    Housing style & price:
    Primarily ranch-style and custom-built waterfront homes, with prices ranging from $450K–$900K+ depending on water access and lot size.

    Advantages:
    Peaceful, low-traffic neighborhood with direct canal access for boating and fishing.

    Considerations:
    Limited commercial amenities nearby; most shopping and dining options are in town.

    Best for:
    Buyers seeking a private waterfront lifestyle with easy access to the Chesapeake & Delaware Canal.

      School District

      Cecil County Public Schools

      Primary District for Chesapeake City and the surrounding southern Cecil County area. Cecil County Public Schools (CCPS) is recognized for its strong academic programs, community engagement, and dedication to preparing students for both college and career success. The district combines small-town attention with access to modern resources and technology.

      Highlights:

      • Schools: Chesapeake City Elementary, Bohemia Manor Middle School, and Bohemia Manor High School.
      • Programs: Offers Advanced Placement (AP) and dual-enrollment programs through partnerships with Cecil College, as well as career and technical education opportunities. Students can also participate in specialized academies focused on STEM, agriculture, and the arts.
      • Community Focus: The district fosters close relationships between teachers, families, and the community, hosting events and service initiatives that encourage collaboration and civic pride.
      • Strengths: Bohemia Manor High School is known for its academic excellence, small class sizes, and strong extracurricular programs, including athletics and performing arts.
      • Ideal For: Families seeking a well-rounded education in a supportive, community-oriented environment that emphasizes both academics and personal growth.