$574,447Average Value$324Average Price per Sq Ft34Homes 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
Bonnie Fleishman,
an experienced agent in this area.
GreatSchools:
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On average, homes in Shady Side, MD sell after 41 days on the market compared to the national average of 56 days. The median sale price for homes in Shady Side, MD over the last 12 months is $439,950, up 10% from the median home sale price over the previous 12 months.
Welcome to 4909 Olive Street, a newer construction three bedroom, two and a half bath home in the waterfront community of Avalon Shores. Offering a functional layout, contemporary finishes, open living spaces, a fully fenced in backyard, and a private driveway. Avalon Shores residents enjoy access to a community beach, fishing pier, boat ramp, kayak launch, waterfront park, playground, basketball
This Stylish New home is move in ready and just in time to enjoy the summer breezes at the community Beach areas and play grounds! It is ready for your personal touch to make it your own! Main level features include Luxury Vinyl Plank flooring, 9' ceilings, Luxury kitchen with granite countertops, stainless steel appliances accented with sleek white cabinets with soft close drawers and a center
Rare Waterfront Opportunity on South Creek! Bring your vision and make this special waterfront property your own! Situated on a rare 0.74-acre lot, this home has been lovingly maintained by the same family for many years and is ready for its next chapter. Enjoy the waterfront lifestyle with your private pier, offering easy access for boating, fishing, kayaking, or simply relaxing by the water.
Located in the charming Back Bay Beach area of West River, 1003 Henry Avenue offers the relaxed feel of Southern Anne Arundel County living with easy access to the water, marinas, local dining, and nearby historic Galesville. Enjoy the laid-back coastal lifestyle of the West River, with Galesville Wharf, waterfront restaurants, boating access, and scenic outdoor destinations just minutes away.
AUGUST Delivier!!!!Enjoy water views of the community harbor with 60 boat slips and direct access to the Chesapeake Bay—a dream setting for boating and coastal living. This beautifully crafted home features classic board-and-batten siding and a welcoming front porch that creates timeless curb appeal. Inside, the open-concept layout seamlessly connects the dining area and family room, making
AUGUST DELIVERY! Enjoy water views of the community harbor with 60 boat slips and direct access to the Chesapeake Bay—a dream setting for boating and coastal living. This beautifully crafted home features classic board-and-batten siding and a welcoming front porch that creates timeless curb appeal. Inside, the open-concept layout seamlessly connects the dining area and family room, making it
Enjoy water views of the community harbor with 60 boat slips and direct access to the Chesapeake Bay—a dream setting for boating and coastal living. This beautifully crafted home features classic board-and-batten siding and a welcoming front porch that creates timeless curb appeal. Inside, the open-concept layout seamlessly connects the dining area and family room, making it perfect for everyday
Welcome to 1211 Linton Lane, where space, comfort, and water-access living come together in the heart of Shady Side. Located near the Chesapeake Bay, local marinas, boat ramps, parks, and fishing spots, this home offers the ideal opportunity to enjoy Southern Anne Arundel County’s relaxed coastal lifestyle. Set on a generous lot, the property provides plenty of outdoor space for entertaining,
Marlena McWilliamsKeller Williams Capital Properties
Experience the best of the Chesapeake Bay in this 3-bedroom, 2.5-bathroom Colonial, in the sought-after Columbia Beach neighborhood! Nestled in a quiet, gated, water-privileged community, this home offers more than just a place to live—it offers a lifestyle complete with a private pier, boat ramp, tennis/basketball courts, and a playground. The heart of the home is the beautifully curated
Professional pictures coming!! Rarely available and proudly offered for the first time, this spacious split-foyer home is nestled on nearly a quarter-acre lot in the highly desirable water-privileged community of Cedarhurst. Lovingly maintained by its original owner, this well cared for residence offers 4 bedrooms, 3 full bathrooms, and multiple living spaces designed for both comfort and
Escape the hustle and bustle of city life with this exceptional land opportunity in Shady Side, MD. Nestled in a tranquil community, this parcel offers the perfect setting to build your dream home surrounded by nature’s beauty. Enjoy the best of both worlds—peaceful seclusion with easy access to Route 2 and Route 4, making travel to Annapolis, Baltimore, and Washington, D.C., a breeze. Immerse
Vacant Lot Ideal for Expansion or New Venture. Perfect for Boat Storage or New Building. Leverage its proximity to high-demand recreational areas for profitable boat and trailer storage, or business vehicles, or develop the lot into a commercial building for your business, or to lease the space to a business who is looking to serve the local community.
Welcome to 4909 Olive Street, a newer construction three bedroom, two and a half bath home in the waterfront community of Avalon Shores. Offering a functional layout, contemporary finishes, open living spaces, a fully fenced in backyard, and a private driveway. Avalon Shores residents enjoy access to a community beach, fishing pier, boat ramp, kayak launch, waterfront park, playground, basketball
This Stylish New home is move in ready and just in time to enjoy the summer breezes at the community Beach areas and play grounds! It is ready for your personal touch to make it your own! Main level features include Luxury Vinyl Plank flooring, 9' ceilings, Luxury kitchen with granite countertops, stainless steel appliances accented with sleek white cabinets with soft close drawers and a center
Waterfront living with a private dock—all for under $800,000! Nestled in the charming Avalon Shores community, this beautifully updated coastal home perfectly blends classic elegance with modern comfort. The open-concept layout features two distinct living areas, ideal for both entertaining and daily relaxation. At the heart of the home is a premium kitchen equipped with granite countertops,
This Stylish New home is move in ready and just in time to enjoy the summer breezes at the community Beach areas and play grounds! It is ready for your personal touch to make it your own! Main level features include Luxury Vinyl Plank flooring, 9' ceilings, Luxury kitchen with granite countertops, stainless steel appliances accented with sleek white cabinets with soft close drawers and a center
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