Bayside

A sought-after place to call home.

Community Profile

Life in Bayside

Welcome to Bayside

Bayside is a picturesque waterfront community located on Kent Island in Chester, MD, along the northern Chesapeake Bay. Adjacent to Castle Harbor Marina and near the Chester River’s mouth, Bayside is home to 288 single- and multi-level residences, offering a serene and coastal lifestyle. The community’s diverse housing options cater to various family sizes and lifestyle needs, making it an attractive choice for families, professionals, and retirees alike.

Residents of Bayside enjoy an array of resort-style amenities, including a spacious clubhouse for gatherings and events, a fully equipped exercise center, and outdoor amenities such as a swimming pool, hot tub, and tennis courts. The community’s waterfront location offers stunning bay views and access to numerous water-related activities, with the marina providing easy opportunities for boating and fishing.

Bayside’s prime location on Kent Island provides a peaceful retreat while remaining just a short drive from Annapolis and its dining, shopping, and cultural attractions. Its proximity to major highways also allows for convenient commuting to Baltimore, Washington, D.C., and beyond. With its blend of coastal charm, modern conveniences, and vibrant community spirit, Bayside in Chester is a sought-after place to call home.

By the Numbers

Data based on information from Jan 1, 2020 to Jan 1, 2025
  • Average Sales Price: $210,000 - $835,000
  • Average Number of Annual Sales: 17
  • Average List-to-Sale Price Ratio: 97.7%
  • Average Days on Market: 34
  • Average Price Per Square Foot: $218.67
  • Average Bedrooms: 3
  • Average Bathrooms: 3

Highlights

  • Lifestyle: Suburban, Water Access
  • Community Association: Mandatory
  • Community Amenities: Clubhouse, Fitness Center, Tennis and Pickleball Courts, Volleyball Courts, Community Pool(s), Common Grounds

Visit the Community Website

About the Area

Regional Background

The Eastern Shore is characterized by waterfront towns, agricultural landscapes, and a slower, more intentional pace of life. Buyers are often motivated by lifestyle considerations, privacy, and long-term ownership, including second-home purchasers and those seeking an alternative to more densely populated markets. Real estate activity in the region reflects a strong connection to place and a preference for quality over speed.

Lifestyle Pillars

Waterfront, Second-Home, Historic towns, Agriculture, Quiet luxury

Current Opportunities

Property Listings

Filter neighborhood properties

CONTACT the HOUSECATS company

Let's Work Together

Whether you are preparing to sell, searching for a home or simply trying to understand what comes next, tell us what you are working through. We will help identify the clearest path forward.