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Compass Real Estate

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Housecats Company

CHESTER

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 SINCE JAN 1 2020 to jan 1 2025

AVERAGE SALES PRICE

AVERAGE NUMBER OF ANNUAL SALES

AVERAGE LIST TO SALES PRICE RATIO

AVERAGE DAYS ON MARKET

AVERAGE PRICE PER SQUARE FOOT

AVERAGE BEDROOMS

AVERAGE BATHROOMS

$210,000 - $835,000

17

97.7 %

34

$218.67

3

3

Highlights

lifestyle

community association

community amenities

SUBURBAN, WATER ACCESS

MANDATORY

CLUBHOUSE, FITNESS CENTER, TENNIS AND PICKLEBALL COURTS, VOLLEYBALL COURTS, COMMUNITY POOL(S), COMMON GROUNDS

CHESTER

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

Related Market Reports

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2077 Somerville Rd

suite 200

Annapolis, MD 21401

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