$555,550Average Value$309Average Price per Sq Ft21Homes For Sale
Boating and fishing on the Chesapeake Bay in Shady Side
Life in Shady Side revolves around the water. Facing the Chesapeake Bay on a peninsula in Anne Arundel County, this area is commutable to metros like Annapolis and Washington, D.C., but still offers a slow-paced life on the water. “I think it’s a wonderful lifestyle. There’s a lot of activity, but it’s a relaxing, fun place to be. You can really feel like you’re part of a community,” says Amelia Whitman, agent with Long & Foster Real Estate and area native. “I’m a boater, and I can’t imagine living anywhere else.”
Water front homes are a common side in Shady Side.
Shady Side offers quiet streets to its residents.
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Small subdivisions and more private waterfront homes
Shady Side’s residential options include cozy houses in subdivisions and spacious properties on the waterfront. “Particularly for waterfront properties, there are people who use them as second homes, and their primary home is in Northern Virginia or D.C. But there are a lot of people that live here full-time. It works well for both,” Whitman says. Smaller ranch-style houses and cottages typically sell for between $225,000 and $420,000, while spacious New Traditionals sell for between $430,000 and $900,000. A handful of upscale properties with private piers sell for above $1 million. As a waterfront community, many properties in Shady Side do have an elevated flood risk. Shady Side’s Cap Index Crime Score is a 1, far below the national average of 4.
Large acres and family homes are scattered around the areas of Shady Side.
Lakefront homes are very popular in Shady Side.
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Boating and other activities on the Chesapeake Bay
Kayaking, canoeing, sail boating, powerboating and fishing are among the popular activities in this water-oriented community. On the inner side of the peninsula, paddleboarding on the quiet waters of the West River is also available. “Half of Shady Side is in the West River. It’s a great place to have your boat because it’s protected,” Whitman says. For property owners who don’t have private piers, some neighborhoods in Shady Side have community waterfronts, and there are several marinas on the peninsula, including Parish Creek Landing and Chalk Point Marine. Shady Side Park has its own public boat launch, as well as athletic fields and courts, trails and a playground. Franklin Point State Park covers nearly 500 acres in Shady Side, offering hiking trails and kayaking among marshy areas along Deep Creek, Flag Pond and the bay.
Locally owned restaurants in Shady Side and more in Deale
Locals can start their day with a coffee and breakfast platter at Driftwood Diner, or cool off on summer days at Shady Side Soft Serve Ice Cream. The bordering community of Deale has several more restaurants, cafes and shops. Christopher’s Fine Foods has grocery items off Shady Side Road, and nearby towns like Edgewater and Dunkirk have major chains like Giant Food and Safeway.
Shady Side Market is a local staple.
Shopping areas sit along major streets in Shady Side
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Shady Side’s Independence Day parade draws crowds
Each year, Shady Side hosts its July 4th Parade, featuring decorated floats, motorcycles, marching bands, and more to support the community and celebrate the holiday. The neighboring community of Deale also hosts events, such as the Deale Parade of Lights. The parade is held each December along Rockhold Creek, with community members showing off their boats, decked out with holiday lights.
Anne Arundel County Public Schools serve students
Students in the community may begin at Shady Side Elementary School, which has a B rating from Niche, and continue to B-minus-rated Southern Middle School and B-plus-rated Southern High School. Southern High offers many Advanced Placement and elective courses, as well as career pathways in subjects like cosmetology, dental assisting, welding and HVAC. The high school also offers dozens of athletic teams, including lacrosse, tennis, wrestling, golf, bocce and bowling.
Welcome to Shady Side Elementary School in Shady Side, Maryland.
Southern High School in Harwood has 1,066 students.
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Getting to D.C. and Annapolis from Shady Side
Downtown Washington, D.C. is about 35 miles west of Shady Side, and drivers can get there via Maryland Route 4. Alternatively, commuters can drive to New Carrollton Metro Station, about 30 miles west, and ride the rest of the way into D.C. Several park and rides, such as the Lothian Wrighton Road Park & Ride off Route 4, are also available. The D.C. region is also home to Ronald Reagan Washington National Airport and Dulles International Airport. Annapolis, the capital of Maryland, is about 20 miles north and is accessible via Maryland Route 468. Annapolis is home to Luminis Health Anne Arundel Medical Center, one of the closest major hospitals to Shady Side.
Written By
Faith Wakefield
Photography Contributed By
Conar McDaniel
Video By
Charles Kennedy
Interested in learning more about homes in this area?
Reach out to
Ana Yassawy,
an experienced agent in this area.
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On average, homes in Shady Side, MD sell after 36 days on the market compared to the national average of 54 days. The median sale price for homes in Shady Side, MD over the last 12 months is $412,450, up 6% from the median home sale price over the previous 12 months.
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This spacious and well-maintained home offers the ease of one-level living at it's best. The modern kitchen opens to a cozy family room with sliding door that leads to a stunning sunroom and adjacent deck—perfect for relaxing or entertaining. Enjoy formal spaces with both a living room and dining room, along with a generous primary suite complete with a private full bath. Two additional bedrooms
Rare opportunity to lease a fully renovated waterfront home tucked at the quiet end of the road in Churchton, offering privacy, tranquility, and sweeping Chesapeake Bay views from multiple rooms. This refined retreat features two spacious bedrooms and two beautifully updated full baths with porcelain tile and heated floors. The redesigned kitchen showcases granite countertops, gas cooking,
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