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Compass Real Estate

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Housecats Company

SHADY SIDE

Shady Side

Shady Side, Maryland, is a quaint waterfront community located on the western shore of the Chesapeake Bay in southern Anne Arundel County. Known for its relaxed, coastal charm, Shady Side offers residents a peaceful lifestyle surrounded by natural beauty. The area is home to numerous marinas, making it ideal for boating, fishing, and water sports enthusiasts. With its scenic waterfront views and access to the Chesapeake Bay, Shady Side has long been a popular destination for those seeking a tranquil retreat.

The community has a rich maritime history, and much of its appeal comes from its small-town charm, friendly residents, and local traditions. Outdoor activities are abundant, with parks, nature reserves, and waterfront areas offering space for hiking, bird watching, and enjoying the outdoors. The Shady Side Rural Heritage Society also helps preserve the town's history and holds various cultural and community events throughout the year.

Despite its serene setting, Shady Side is within convenient driving distance of Annapolis, Washington, D.C., and Baltimore, offering easy access to shopping, dining, and entertainment. The area’s schools and amenities also contribute to its appeal for families seeking a quiet, waterfront community with the conveniences of nearby cities. Whether you’re drawn by the allure of the Chesapeake Bay or the community’s charming, laid-back atmosphere, Shady Side is a hidden gem along Maryland’s coast.

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

$200,000 - $3,850,000

110

99.5%

30

$275.50

3

2

Highlights

lifestyle

community association

community amenities

RURAL, WATER ACCESS

N/A

BOAT LAUNCH, MARINA(S)

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SHADY SIDE

About the Area

Regional Background

Greater Annapolis is defined by its relationship to the water, its historic core, and a lifestyle that blends tradition with modern convenience. The region attracts a broad mix of buyers, from professionals and families seeking established neighborhoods to second-home and luxury buyers drawn to waterfront living and proximity to Washington, D.C. Demand here is often shaped as much by lifestyle and long-term value as by short-term market conditions.

Lifestyle Pillars

Waterfront, Historic, Golf, Walkable, Commuter

Related Market Reports

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2077 Somerville Rd

suite 200

Annapolis, MD 21401

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