Shady Side Real Estate

Shady Side Real Estate

Welcome to Shady Side, Maryland – a hidden gem nestled in the heart of Anne Arundel County. This charming waterfront community, located along the serene shores of the Chesapeake Bay, offers a unique blend of natural beauty, rich history, and a tight-knit community atmosphere. With its picturesque landscapes and tranquil environment, Shady Side is the perfect retreat for those seeking a peaceful lifestyle while still being within reach of urban conveniences.

Shady Side is renowned for its stunning waterfront vistas and abundant outdoor recreational opportunities. Residents and visitors alike can enjoy activities such as boating, fishing, and kayaking, all while soaking in the breathtaking views that the Chesapeake Bay has to offer. The area's lush parks and nature trails provide the perfect backdrop for hiking, picnicking, and enjoying the vibrant local wildlife.

The community is steeped in history, with roots tracing back to the 19th century. Today, Shady Side maintains its quaint charm with a mix of historic homes and modern residences, creating a delightful tapestry of architectural styles. The friendly atmosphere and strong sense of community make it easy to connect with neighbors and participate in local events.

Shady Side is also conveniently located just a short drive from the bustling cities of Annapolis and Washington, D.C., allowing residents to enjoy the best of both worlds – a peaceful retreat with easy access to urban amenities. Whether you’re looking to settle down in a cozy waterfront home or simply explore the beauty of this unique area, Shady Side is a wonderful place to call home. Come discover the allure of this enchanting community today!

Newest Listings in Shady Side

2 Beds ⋅ 1 Baths

This delightful 1930s ranch-style cottage offers a perfect blend of vintage charm and modern comfort. Set on a generous 1.25-acre lot, the property boasts ample outdoor space, ideal for gardening, entertaining, or simply enjoying the tranquility of nature. An inviting outbuilding adds versatility, whether you envision a workshop, studio, or extra storage space. The expansive driveway ensures convenient parking for you and your guests, making gatherings a breeze. Imagine sipping your morning coffee on a sun-drenched patio, surrounded by the beauty of your own private oasis. With two cozy bedrooms and a well-appointed full bathroom, this home is designed for comfort and ease. The layout encourages a warm, inviting atmosphere, perfect for creating lasting memories. This property is not just a house; it's a place where you can truly feel at home. Embrace the opportunity to make this charming cottage your own and enjoy the serene lifestyle it offers. Don't miss your chance to experience the perfect blend of comfort and outdoor living!

4924 Kellam Rd, Shady Side

Listing courtesy of District Pro Realty. Contact: (301) 452-5691

4 Beds ⋅ 3 Baths

Now is the time to take a fresh look at this beautifully designed 2022-built home, where modern style, thoughtful details, and a peaceful wooded setting come together. Move-in ready and filled with natural light, this home offers the space and flexibility buyers are looking for—without the wait or expense of new construction. Step inside to an open two-story foyer and into the inviting main living area with vaulted ceilings. Nine-foot ceilings throughout the home, charming cottage-style windows, and an open layout create an airy, comfortable feel. LVP flooring flows throughout the living room, kitchen, and wide hallway, making everyday living and entertaining effortless. The kitchen is a standout, featuring granite countertops, soft-close cabinetry, oil-rubbed bronze fixtures, and a center island with seating. There’s plenty of room for a dining table, creating an easy gathering space for family and friends. The main level offers three bedrooms including a spacious owner’s suite with two closets providing excellent storage, while the distinctive en-suite bath features dual sinks, granite countertops, a walk-in shower, custom wall trim. The two additional bedrooms feature custom molding, decorative wall treatments, and stylish finishes. The hall bath includes a granite vanity and shower/tub combination. And there’s even more living space downstairs! The lower level features a large recreation room with sliding glass doors to the backyard, a flexible fourth bedroom perfect for guests, a home office, gym, or hobby room, plus another full bath. This versatile lower level gives you room to spread out, work from home, entertain, or accommodate overnight guests. Outside, raised garden beds are ready for your favorite flowers, herbs, and vegetables. The mature, wooded backdrop provides a peaceful sense of privacy and a beautiful setting to enjoy year-round.

1411 Haile Pkwy, Shady Side

Listing courtesy of TTR Sotheby's International Realty. Contact: 4106733344

Beautiful corner lot located just one block from the Chesapeake Bay and the community amenities, including a marina, clubhouse, pier, beach, playground, and more. The lot is level and cleared, making it ready for your plans. Public sewer is available at the road. Boat, RV, and car currently on the property will be removed prior to settlement.

1198 Oak Ave, Shady Side

Listing courtesy of Schwartz Realty, Inc.. Contact:

3 Beds ⋅ 5 Baths

Waterfront living at its finest in Avalon Shores on South Creek! This 3-bedroom, 4.5-bath home features a versatile study/bonus room, beautiful wood floors, updated kitchen and baths, and modern fixtures throughout. Enjoy water views from the expansive screened-in back porch or multiple decks spanning the second and third levels. The waterfront setup is ideal for boating enthusiasts with a remote-controlled boat lift and three jet ski lifts. A 2-car garage provides convenient parking and storage. New roof installed in 2023, while bulkhead was redone in 2016. Enjoy relaxing, entertaining, and life on the water!

5060 Lerch Dr, Shady Side

Listing courtesy of Redfin Corp. Contact: 3016586186

4 Beds ⋅ 2 Baths

There is something special about life near the Chesapeake Bay—and 1221 Bast Lane captures it beautifully. Completely remodeled from top to bottom, this charming one-level Coastal Craftsman combines fresh, sophisticated interiors with incredible outdoor space and one of the most impressive detached garages you will find. Set on a beautiful lot just shy of an acre in Shady Side, the home offers four bedrooms and an easy, comfortable floor plan filled with natural light, beautiful windows, gorgeous flooring, and thoughtful finishes throughout. At the heart of the home is a stunning gourmet kitchen featuring beautiful cabinetry, warm butcher-block countertops, stainless steel appliances, a stylish backsplash, generous workspace, and a fresh coastal aesthetic that makes the entire space feel inviting. The primary suite is a wonderful retreat with an enormous walk-in closet and a sleek, spa-inspired bath featuring a beautiful walk-in shower with glass doors. Additional bathrooms carry the same clean, sophisticated design, while the incredible laundry room proves that even the most practical spaces can be beautiful. Step outside onto the spacious deck and imagine summer dinners, weekend cookouts, morning coffee, or a glass of wine as the sky changes color at sunset. The huge yard offers nearly an acre to spread out, garden, play, entertain, or simply enjoy having space around you. And then there is the garage. More than 1,500 square feet of detached garage and workspace with THREE bays and electric creates an absolute dream setup for car enthusiasts, collectors, hobbyists, contractors, or anyone who wants room for vehicles, tools, storage, and projects without sacrificing the house or yard. The home and garage roofs date to 2023, along with the home's siding. Beyond the property, Shady Side delivers the Chesapeake lifestyle people fall in love with: water views, beautiful sunsets, neighbors walking their dogs, kids playing, and the relaxed sense of community that makes evenings feel a little slower and weekends feel a little longer. Here, you can enjoy the character of a coastal community while coming home to a beautifully renovated property where the transformation has already been completed. Beautiful inside, extraordinary outside, and filled with unexpected features, 1221 Bast Lane isn't simply move-in ready—it's the kind of place that makes you excited to come home.

1221 Bast Ln, Shady Side

Listing courtesy of Coldwell Banker Realty. Contact: 4102638686

5 Beds ⋅ 4 Baths

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

3 Beds ⋅ 2 Baths

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

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:

3 Beds ⋅ 3 Baths

Welcome home to this beautifully maintained split-foyer in Cedarhurst on the Bay, Shadyside's sought-after water-privilege community. Built in 2015, this 3-bedroom, 2.5-bath home offers 1,838 total finished square feet, including a bright main level with cathedral ceilings and a finished lower level with a half bath — ideal for entertaining or extra living space. Stone and vinyl siding give it great curb appeal, and the 2-car attached garage plus 2-car driveway provide 4 total parking spaces. Owned solar panels keep utility costs low year-round. Just one block to the Chesapeake Bay with community water access, and an easy commute to Annapolis, DC, and Baltimore. Don't miss your chance to own in one of the area's most desirable water-privilege neighborhoods.

1175 Maple Ave, Shady Side

Listing courtesy of Cummings & Co. Realtors. Contact: (410) 823-0033

SELLER FINANCING AVAILABLE! 1.53-acre residential tract in Shady Side, Maryland is an unmatched deal! Located at 6152 Shady Side Rd, this spacious property is tax-assessed at $100,300, but we are offering it to you for just $54,900. Finding premium, cheap land for sale priced at nearly 50% below tax assessment value is extremely rare in Anne Arundel County—making this an investor’s or future homeowner’s dream come true. Zoned Residential (R1), this beautifully situated acreage provides plenty of space to design and build your custom coastal retreat. Location is everything, and this property puts you just 1.84 miles from the shores of the iconic Chesapeake Bay, giving you incredibly quick access to local marinas, public boat launches, crabbing, and waterfront dining. Enjoy the ultimate relaxed, maritime lifestyle while remaining an easy commute away from Annapolis, Baltimore, and Washington, D.C. With our flexible owner financing options, securing your piece of Maryland’s beautiful coastline has never been easier or more affordable. Address: 6152 Shady Side Rd, Shady Side, MD 20764 Acreage: 1.53 Acres County: Anne Arundel County, MD Parcel ID (APN): 7000-0240-5600 Legal Description: 1.53 Acres 6152 Shady Side Rd Shady Side Zoning: Residential (R1) Annual Property Taxes: $1,098.29

6152 Shady Side Rd, Shady Side

Listing courtesy of Rise Real Estate, LLC. Contact: 2025569721

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

4 Beds ⋅ 2 Baths

Welcome to this charming 4-bedroom, 2-bath home in the desirable Snug Harbor community of Shady Side. Offering approximately 1,930 square feet of living space, this property features a spacious layout, detached garage, and generous yard with plenty of room to enjoy outdoor living. Conveniently located near marinas, parks, local dining, and Chesapeake Bay recreation, this home presents a wonderful opportunity to enjoy the relaxed waterfront lifestyle with easy access to Annapolis. This property has an exclusive boat slip!

1704 Maryland Ave, Shady Side

Listing courtesy of Sell Your Home Services. Contact: 8882193009

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