Browse All Shady Side MD Between $400K - $500K Properties for Sale

Tastefully updated, magnificent and charming Home for Sale in the water-oriented community of Cedarhurst on the Bay. This Beautiful 5 bedroom 4 bathroom house will deliver on all your needs. Main floor greets you with a bright and spacious open floor plan. Large living room, updated kitchen with quartz countertops, oversized island for 3-4 people and stainless steel appliances, walk-in pantry and a designated dining room of the kitchen. Main floor bedroom and 1 full bath. Separate laundry room and service area completes this floor. 2nd floor offers the Main owners suite with a large walk-in closet and a double vanity en-suite. Another large bedroom with its own custom bath with a walk in shower. 3 more bedrooms and another 3rd bath completes this level. Plenty of closet space throughout the house for all your organization needs. Pull down attic for additional storage. Great private back yard. 4-5 bedroom driveway. 1 minute walk to the bay and the beautiful views of the water. This property will deliver.

1194 Oak Ave, Shady Side

Listing courtesy of Maryland Realty Company. Contact: 4109296161

$419,000

3 Beds ⋅ 2 Baths

*PROFESSIONAL PHOTOGRAPHY COMING SOON* Welcome to 1437 Cedarhurst Road in Shady Side, MD! This beautifully updated 3-bedroom, 2-full-bath rancher was completely remodeled in 2023 and offers comfortable one-level living with fresh, modern finishes throughout. Major updates include a newer HVAC system, newer roof and gutters, and a new water filtration system. Additional highlights include a one-car garage, abundant parking, and a spacious backyard with a storage shed, providing plenty of room for outdoor equipment, tools, and additional storage. Located just minutes from the waterfront, this property offers convenient access to the Chesapeake Bay and opportunities for boating, kayaking, fishing, crabbing, and other waterfront activities. With extensive updates, generous outdoor space, and a location close to the water, 1437 Cedarhurst Road has so much to offer!

1437 Cedarhurst Rd, Shady Side

Listing courtesy of Samson Properties. Contact: 7033493900

$430,000

Large lot ready for you to build your private compound! 8.5 acres contains wetland areas. Located in a water-privileged community and two blocks to the Chesapeake Bay. Cedarhurst on the Bay has a private marina, pier, beachfront and community house for owners use only. Located on a peninsula, Cedarhurst on the Bay has easy access to the water and amazing views of the Bay! Nearby Annapolis, Baltimore, Washington, DC, BWI and DCA airports. You're buying more than land to build on, you're buying that water-privileged lifestyle you've always dreamed of! Nearby restaurants, shopping, parks, the Capt. Salem Avery House and The Lula G. Scott Community Center (both on the historic registry) and more. Across the street from the historic "The Brick House" (formerly "The Bay View Inn"), which is undergoing renovations. More photos to come.

1495 Cedarhurst Rd, Shady Side

Listing courtesy of Taylor Properties. Contact:

$415,000

3 Beds ⋅ 3 Baths

Welcome to the Chesapeake Bay lifestyle in the waterfront community of Cedarhurst! Just one block from the Bay, this picture-perfect Colonial combines classic curb appeal, comfortable living spaces, and the kind of community amenities that make everyday life feel a little more like vacation. Start your mornings on the welcoming front porch and spend summer evenings entertaining on the rear deck overlooking the lush landscaping. Inside, the inviting living room features a cozy wood-burning fireplace, while the spacious kitchen offers painted cabinetry, stainless steel appliances, and plenty of room for an eat-in dining area. Upstairs, you’ll find three generously sized bedrooms, including a spacious primary suite with vaulted ceilings and a private en-suite bath. Two additional bedrooms share a dedicated hall bath. Major updates include a NEW ROOF in 2022 and HVAC replaced in 2021. But the Cedarhurst lifestyle may just be the best part! Stroll down to the community waterfront where you’ll find a picnic area and playground overlooking the Chesapeake Bay—the perfect spot to catch the sunset to your right or watch the sunrise to your left. Launch your kayak or jet ski from the community boat ramp, or take advantage of available boat slips for just $400 per year, per slip. Residents also have exclusive access to rent the Cedarhurst Community Center for parties and gatherings. From boating and waterfront picnics to catching both sunrise and sunset along the Bay, this is more than a home—it’s the Chesapeake lifestyle you've been looking for. This property is 100% financing approved, no downpayment local program available! Welcome home!

1193 Oak Ave, Shady Side

Listing courtesy of RE/MAX One. Contact: 4105356291

$465,000

5 Beds ⋅ 2 Baths

Welcome to the Waterfront Community of Cedarhurst by the Bay tucked away on the quiet Shady Side Penninsula. This Spacious 5 Bedroom, 2 Full Bath home sits just steps away from the amazing community waterfront offering stunning views of the Chesapeake Bay from the Upper Balcony and a multitude of community ammenities. Wake up to breathtaking sunrises and end your evenings watching colorful sunsets. Enjoy the everyday vacation life on the expansive community waterfront with panoramic views and and refreshing coastal breezes. Enjoy time with family and friends at the picnic areas, ballfields and playground. The community pier stretches out into the bay, has a gazebo and is perfect for fishing and crabbing. The Community Harbor has over 60 slips that can be reserved by community members and direct has access to the bay serving both power boats and sail boats. Whether you are launching a boat or relaxing on the deck, this is coastal living at its finest! Your everyday vacation starts here! Cedarhurst is a Special Community Benefit District.

1220 Grove Ave, Shady Side

Listing courtesy of Coldwell Banker Realty. Contact: kelly.thompson@cbmove.com

$429,900

3 Beds ⋅ 3 Baths

Welcome to this charming home located in a sought-after water-privileged community, just a short walk to the beach, boat slips, playground, boat ramp, and other neighborhood amenities. The main level features a spacious primary suite with a private full bath, offering convenient one-level living. The beautifully appointed kitchen boasts a center island with a gas cooktop, wall oven, abundant cabinet space, and a bright dining area. The kitchen opens seamlessly to the spacious living room, highlighted by a cozy gas fireplace and engineered hardwood flooring throughout the main level. Step outside through the kitchen slider to a wonderful screened porch, the perfect spot to relax and enjoy the outdoors. An adjoining rear deck overlooks the fully fenced backyard, providing plenty of space for entertaining, pets, or play. Upstairs, you'll find two additional bedrooms connected by a convenient Jack-and-Jill bathroom. Ideally located for an easy commute to both Washington, D.C., and the Annapolis area, this home also qualifies for 100% financing through the USDA Rural Development loan program, making homeownership even more attainable. Seller is providing a 1 year home warranty. 24hr. showing notice is required.

1161 Steamboat Rd, Shady Side

Listing courtesy of Schwartz Realty, Inc.. Contact:

$480,000

3 Beds ⋅ 3 Baths

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 court, and picnic areas. Conveniently located near local marinas, waterfront dining, parks, and Chesapeake Bay attractions, with easy access to Annapolis, Edgewater, Washington, D.C., and Baltimore. A great opportunity to enjoy a water oriented lifestyle in one of Southern Anne Arundel County's popular waterfront communities.

4909 Olive St, Shady Side

Listing courtesy of TTR Sotheby's International Realty. Contact: (410) 280-5600

$470,000

3 Beds ⋅ 3 Baths

Welcome to this beautiful home in the highly sought-after Avalon Shores community, offered for sale by only its original builders of the home. Situated on over one-third of an acre, this well-maintained 3-bedroom, 2.5-bath residence offers the perfect blend of comfort, space, and community living. The fully fenced backyard provides an ideal setting for entertaining, family gatherings, or simply relaxing outdoors. Inside, the updated kitchen features granite countertops and stainless steel appliances, while gorgeous hardwood floors with custom inlay accents add warmth and character throughout the home. The spacious primary suite boasts vaulted ceilings and a private en-suite bath, creating a comfortable retreat. All bedrooms are generously sized and offer ample closet space. Enjoy peaceful mornings with a cup of coffee or unwind in the evenings on the charming enclosed front porch, perfect for reading or taking in the neighborhood atmosphere. Residents of Avalon Shores enjoy exceptional community amenities, including two playgrounds, baseball fields, a community boat launch, and water access. Opportunities like this are rare in such a desirable waterfront community. Don't miss your chance to make this wonderful home your own!

4951 Bonniewood Dr, Shady Side

Listing courtesy of Schwartz Realty, Inc.. Contact:

$450,000

3 Beds ⋅ 2 Baths

Welcome to this beautifully maintained Colonial perfectly positioned on a desirable corner lot in the water-oriented community of Cedarhurst—where Chesapeake Bay living is part of everyday life. Just in time for summer, enjoy the opportunity to lease a boat slip for only $400 per year with direct access to the Chesapeake Bay, making weekends on the water easier than ever. Inside, you’ll find hardwood floors throughout and a spacious layout designed for both comfortable living and entertaining. The oversized 21’ x 23’ primary suite offers a true retreat with plenty of room to unwind, while the additional bedrooms are generously sized as well. The main level features a versatile gym/office space that could easily serve as a fourth bedroom, guest room, or playroom depending on your needs. The heart of the home is the large eat-in kitchen with ample space for gathering, complemented by a separate formal dining room and an expansive family room featuring a cozy wood-burning fireplace. Major updates include a new roof installed in 2020, offering peace of mind for years to come. Conveniently located in a USDA-approved area, this home also qualifies for 100% financing eligibility for qualified buyers. If you’ve been searching for spacious living paired with a sought-after water lifestyle, this Cedarhurst gem checks all the boxes.

1217 Pine Ave, Shady Side

Listing courtesy of RE/MAX One. Contact: 4105356291

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