$568,151Average Value$325Average Price per Sq Ft25Homes 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
Reid Buckley,
an experienced agent in this area.
GreatSchools:
The GreatSchools Rating helps parents compare schools within a state based on a variety of school quality indicators and provides a helpful picture of how effectively each school serves all of its students. Ratings are on a scale of 1 (below average) to 10 (above average) and can include test scores, college readiness, academic progress, advanced courses, equity, discipline and attendance data. We also advise parents to visit schools, consider other information on school performance and programs, and consider family needs as part of the school selection process.
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On average, homes in Shady Side, MD sell after 41 days on the market compared to the national average of 58 days. The median sale price for homes in Shady Side, MD over the last 12 months is $439,000, up 11% from the median home sale price over the previous 12 months.
Rare 1-acre private lot located in sought after Idlewilde Acres backing up to Jack Creek Park! Upgrades include: 2023 enlarged rear decking, ADT Alarm system, generator hook up. 2023 full kitchen renovation - upgraded cabinetry, leathered granite counter-top, farmhouse sink, back splash upgraded stove top / microwave, and all new wood flooring on main level. Renovated half bath-2023. 2024 new
Coastal Comfort, Steps to the Beach - Tucked in the water privileged community of Cedarhurst on the Bay and just a short stroll to the beach and neighborhood amenities, this charming cottage offers relaxed coastal living with a layout full of character. The home features three bedrooms, two with beautiful coffered ceilings that add height and architectural interest. The full bath includes a tub
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.
THIS IS A TO BE BUILT HOME. Act soon while you are able to still personalize this home with interior selections!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.
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
Photos coming soon! Rarely available and proudly offered for the first time, this spacious split-foyer home sits on nearly a quarter-acre lot in the desirable water-privileged community of Cedarhurst. Built and lovingly maintained by the original owner, this home features 4 bedrooms, 3 full bathrooms, two separate living areas, and an updated open-concept kitchen designed for comfortable everyday
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,
Welcome to this inviting single-family home in the heart of Shady Side! This lovely residence features 3 bedrooms, 2.5 bathrooms, and approximately 2,235 sq ft of versatile living space — thoughtfully laid out to balance comfort and function.Step inside to a warm, open floor plan where natural light enhances every room, and an efficient layout makes everyday living easy. A well-appointed
Welcome to 4721 Oak Road, your waterfront paradise on the Chesapeake Bay! Nestled in the sought-after Felicity Cove community of Shady Side, this custom-built 2014 coastal home seamlessly blends modern luxury with effortless waterfront living. Boasting 4 spacious bedrooms, 3 full bathrooms, and 1,868 square feet of pristine living space, this residence shows like new. Step inside to an
LAND LAND in a gated private community! The lot is 3 small lots in total all adjacent to each other. The county has approved building on the lots as ONE dwelling. The home will need to adhere to the building envelope but can be as high as needed (county approved height change)...building a car garage on bottom and build up in SF from there!! A well is needed and there is public septic. I can
Stunning waterfront studio tucked away in a tranquil community on South Creek! Blending comfort, charm and lifestyle seamlessly, you may never leave! This studio offers a full updated kitchen with an eat in area with beautiful views of the water, a full sized washer and dryer and a private entrance to the patio. Upstairs offers a wonderful open concept studio designed for relaxation-a cozy living
AVAILABLE MAY 30- UPDSTED # BR - 2,5 Bath - VERY CLEAN HOME. This community offers wonderful amenities including boat ramp, fishing pier, beach, playgrounds and picnic areas! The home offers newer vinyl plank flooring, owner's suite with full bath & double sinks, open floor plan, wrap-around porch, fully-fenced yard and back deck! MIN CREDIT SCORE OF 640 AND GROSS HOUSEHOLD INCOME OF $100,000.
Enjoy stress-free living with electric, water, sewer, and lawn care all included in the rent (tenant responsible for internet/cable). This charming home offers beautiful views of the West River and is nestled in a quiet, water-privileged community. Features include brand-new LVP flooring, fresh paint throughout, in-unit washer and dryer, and sliding doors leading to a spacious deck overlooking
Beautiful home with full inlaw suite located on 1.41 acres and across from Shady Side Elementary school. Home offers hardwood floors thru out (except inlaw suite), kitchen with granite counter tops, ss appliances, family room with gas fireplace, sliders to rear deck, living room, inlaw suite with separate entrance, kitchen, full bath, separate hvac (subleasing not permitted). Three bedroom and 2
This is a luxury home in Shady Side- turn key in every way for long term low maintenance living. This is not a cosmetic renovation. This home has been comprehensively rebuilt from the inside out, offering the rare combination of modern luxury finishes and complete system-level replacement in an established gated, water-privileged community in Shady Side. Every major component has been replaced,
Check out this beautifully updated home just steps from the Chesapeake Bay and close to the community pier, beach, marina, playground, and more. The interior features fresh paint throughout, brand-new carpet, and laminate flooring on the main level. The spacious primary bedroom includes a private ensuite bathroom for added comfort. Enjoy relaxing on the welcoming front porch with views of the
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