Shady Side

A quaint waterfront community.

Community Profile

Life in Shady Side

Welcome to 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 from Jan 1, 2020 to Jan 1, 2025

 

  • Average Sales Price: $200,000 - $3,850,000
  • Average Number of Annual Sales: 110
  • Average List-to-Sale Price Ratio: 99.5%
  • Average Days on Market: 30
  • Average Price Per Square Foot: $275.50
  • Average Bedrooms: 3
  • Average Bathrooms: 2

Highlights

  • Lifestyle: Rural, Water Access
  • Community Association: N/A
  • Community Amenities: Boat Launch, Marina(s)

 

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

Current Opportunities

Property Listings

Filter neighborhood properties
4911 MAGNOLIA STREET
Active Under Contract MLS® MDAA2155316

4911 MAGNOLIA STREET

SHADY SIDE, MD 20764

$370,000

2 BD 2 BA 960 Sq.Ft.
1704 MARYLAND AVENUE
For Sale MLS® MDAA2153474

1704 MARYLAND AVENUE

SHADY SIDE, MD 20764

$349,900

4 BD 2 BA 1,930 Sq.Ft.
1411 HAILE PARKWAY
For Sale MLS® MDAA2156658

1411 HAILE PARKWAY

SHADY SIDE, MD 20764

$525,000

4 BD 3 BA 1,905 Sq.Ft.
1437 CEDARHURST ROAD
For Sale MLS® MDAA2155576

1437 CEDARHURST ROAD

SHADY SIDE, MD 20764

$419,000

3 BD 2 BA 1,248 Sq.Ft.
4921 OLIVE STREET
For Sale MLS® MDAA2148420

4921 OLIVE STREET

SHADY SIDE, MD 20764

$349,900

3 BD 1 BA 1,008 Sq.Ft.
690 PLANTATION BOULEVARD
Coming Soon MLS® MDAA2154606

690 PLANTATION BOULEVARD

WEST RIVER, MD 20778

$649,900

3 BD 2.5 BA 2,316 Sq.Ft.
SEARCH HOMES

Around the Community

Around Shady Side, MD

There's plenty to do around Shady Side, including shopping, dining, nightlife, parks, and more. Data provided by Walk Score and Yelp.

11
Car-Dependent
Walking Score
43
Somewhat Bikeable
Bike Score

Points of Interest

Explore popular things to do in the area, including Corner Grill, Renno's Quality Food Market, and Shadyside Soft Serve Ice Cream.

Name Category Distance Reviews
Ratings by Yelp
Corner Grill Logo
Dining · $$ 0.46 miles 18 reviews 4.3/5 stars
Renno's Quality Food Market Logo
Dining · $ 0.5 miles 6 reviews 4.3/5 stars
Shadyside Soft Serve Ice Cream Logo
Dining · $$$ 0.53 miles 29 reviews 4.2/5 stars
Chesapeake Yacht Club Dining Room Logo
Dining · $$ 0.74 miles 5 reviews 5/5 stars
Dining 1 miles 4 reviews 4/5 stars
Driftwood Diner Logo
Dining · $$ 1.01 miles 55 reviews 4.5/5 stars

Education & Local Resources

Schools in Shady Side, MD

The following schools are within or nearby Shady Side. The rating and statistics can serve as a starting point to make baseline comparisons on the right schools for your family. Data provided by the U.S. Census Bureau.
Type
Name
Category
Grades
School Rating

Shady Side, MD

By the Numbers

Population Households Employment

Shady Side has 1,910 households, with an average household size of 2.34. Data provided by the U.S. Census Bureau. Here’s what the people living in Shady Side do for work — and how long it takes them to get there. Data provided by the U.S. Census Bureau. 4,460 people call Shady Side home. The population density is 671 and the largest age group is Data provided by the U.S. Census Bureau.

4,460

Total Population

High

Population Density Population Density This is the number of people per square mile in a neighborhood.

50 years

Median Age

51 / 49%

Men vs Women

Population by Age Group

0-9:

6.2%

0-9 Years

10-17:

14.3%

10-17 Years

18-24:

4%

18-24 Years

25-64:

53.5%

25-64 Years

65-74:

13.6%

65-74 Years

75+:

8.4%

75+ Years

Education Level

  • Less Than 9th Grade
  • High School Degree
  • Associate Degree
  • Bachelor Degree
  • Graduate Degree
1,910

Total Households

2.34

Average Household Size

$65,833

Average individual Income

Households with Children

With Children:

Without Children:

Marital Status

Married
Single
Divorced
Separated

Blue vs White Collar Workers

Blue Collar:

White Collar:

Commute Time

0 to 14 Minutes
15 to 29 Minutes
30 to 59 Minutes
60+ Minutes

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Contact Details

The HOUSECATS COMPANY
Phone: (410) 991-1382
Email: [email protected]
COMPASS REAL ESTATE
Phone: (410) 429-7425
Address 2077 SOMERVILLE RD, SUITE 200, Annapolis, MD 21401

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