Shady Side Real Estate

Shady Side Real Estate

Welcome to Shady Side, a hidden gem nestled in the heart of Anne Arundel County, Maryland. This charming waterfront community is situated along the serene shores of the Chesapeake Bay, offering residents a unique blend of natural beauty and small-town charm. With its picturesque landscapes and vibrant local culture, Shady Side is the perfect place to call home.

One of the standout features of Shady Side is its stunning views and access to the water. Whether you enjoy sailing, fishing, or simply relaxing by the shore, the community’s proximity to the bay provides endless opportunities for outdoor recreation. The area is also home to several parks and nature reserves, making it an ideal spot for hiking, bird watching, and enjoying the great outdoors.

Shady Side boasts a tight-knit community atmosphere, where neighbors know each other by name and local events bring everyone together. The annual Shady Side Arts and Crafts Festival is a beloved tradition that showcases the talents of local artisans, while the nearby restaurants and shops offer a taste of the local flavor.

For families, Shady Side is served by quality schools and offers a safe, friendly environment for children to grow up in. With easy access to nearby cities like Annapolis and Washington D.C., residents can enjoy a peaceful retreat while still being close to urban amenities.

If you’re looking for a place that combines natural beauty, community spirit, and a relaxed lifestyle, Shady Side is the perfect destination. Come discover the charm of this delightful Maryland town, where every day feels like a vacation!

Newest Listings in Shady Side

$499,900
4 Beds ⋅ 3 Baths
Nestled in the charming Cedarhurst on the Bay community, this delightful split foyer home offers a perfect blend of comfort and convenience. This well-maintained residence features four spacious bedrooms and three full bathrooms, ideal for both relaxation and entertaining. Step outside to discover a serene outdoor oasis, complete with a hot tub for unwinding after a long day. The property also includes a garage and a shed, providing ample storage for all your needs. Enjoy the beauty of nature with easy access to the stunning Chesapeake Bay, where community docks invite you to explore the water and create lasting memories. The neighborhood is known for its friendly atmosphere and strong sense of community. Residents benefit from nearby parks, perfect for leisurely strolls or picnics, and excellent public services that enhance the quality of life. With a walkout basement and a cozy fireplace, this home is designed for comfort and warmth. Experience the joys of living in Cedarhurst on the Bay, where community spirit meets the tranquility of waterfront living. This home is not just a place to live; it's a place to thrive. professional pictures to come.

1183 Cedar Ave, Shady Side

Listing courtesy of United Real Estate Premier. Contact: 5403694460
$619,990
4 Beds ⋅ 3 Baths
Home is ready for immediate occupancy. Coastal Living Just Steps from the Chesapeake Bay! Schaefer Homes invites you to make this beautifully designed coastal-style residence your own located across the street from the bay offering nice water views. Offering over 3 stories of wide open living with LVP flooring through out (Carpet in 2 bedrooms). From the classic board-and-batten siding to the welcoming front porch, the exterior sets a striking first impression. Upper level offers water views and an open-concept layout that seamlessly connects the dining and family rooms, offering the perfect setting for everyday living or entertaining. At the heart of the home is an upgraded kitchen with oversized island, upgraded countertops, stainless steel appliances, and abundant cabinetry—ideal for casual meals or gatherings with friends. A private home office (or flexible choice room) on the main level adds convenience, while upstairs the serene owner’s suite boasts a large picture window with Bay views, a spacious walk-in closet, and a spa-inspired bath with a luxury shower. Walk to community pier, boat ramp, playground, tennis courts and more. Renderings and photos are for illustrative purposes only and may show optional features, upgrades, or configurations not included as standard. Actual features, finishes, and layouts may vary. Flood insurance is approximately $650.00 year. $5,000 in closing assistance with preferred lender and title company.

5314 Al Jones Rd, Shady Side

Listing courtesy of Schwartz Realty, Inc.. Contact:

$499,900
3 Beds ⋅ 3 Baths
Nestled in the charming Avalon Shores community, this delightful Colonial home offers a perfect blend of comfort and modern living. This 3 bedroom and 2.5 bath has a thoughtfully designed space, ideal for both relaxation and entertaining. Step inside to discover an inviting open floor plan adorned with beautiful LVT floors. The huge eat-in kitchen with under cabinet lighting and stainless appliances is great for a family & entertaining with a huge dining area off kitchen. The spacious primary suite offers a serene retreat with new LVT floors and a newly remodeled bath with new vanity, new LVT floors, lighting and toilet. The separate laundry room upstairs is and added bonus!! Outside the extensive hardscape with new concrete walkways complements the lovely 17 x17 back patio and 28x10 back deck and front porch all perfect for enjoying morning coffee or evening gatherings with family and friends. The level lot with maintenance free fenced in yard provides a lovely outdoor space, while the attached garage and asphalt driveway ensure ample parking. The home is wired with a full subpanel for in house generator. There is an encapsulated crawlspace with Aquaguard w/ EZ Breath climate control and dehumidifier. Residents of Avalon Shores enjoy exclusive access to common grounds and picnic areas, a pier/dock, and playground, fostering a sense of community and outdoor enjoyment. With water and lake privileges, you can embrace a lifestyle filled with leisure and recreation. This home is not just a property; it's a sanctuary where family memories are made. Experience the perfect blend of comfort, convenience, and community in this exceptional family oriented home.

1240 Hawthorne St, Shady Side

Listing courtesy of RE/MAX Leading Edge. Contact:

$619,990
4 Beds ⋅ 3 Baths
Welcome to Cedarhurst on the Bay, where every day feels like a coastal escape. This beautifully crafted home is the perfect blend of timeless charm and modern living, set against a backdrop of stunning Chesapeake Bay views that simply never get old. From the moment you arrive, the classic board-and-batten siding and striking exterior create an immediate sense of quality and character that carries beautifully throughout the entire home. Inside, soaring natural light fills the open-concept main level, where the dining area and family room connect seamlessly to create a warm, effortless flow perfect for both quiet evenings and lively get-togethers. The kitchen is nothing short of spectacular, featuring an oversized quartz island, stainless steel appliances, and generous cabinetry that makes cooking and entertaining an absolute pleasure. Need a dedicated workspace or a room to call your own? The main-level home office or flexible choice room delivers exactly that. Upstairs, the owner's suite is a true haven — bathed in natural light through large windows, complete with an expansive walk-in closet and a spa-inspired bath featuring a luxury shower that turns every evening into a retreat. Outside your front door, Cedarhurst's extraordinary four acres of community-owned waterfront property sets this neighborhood apart from anything else in the area. Sip your morning coffee as sunrises illuminate the Bay, stroll to the community center and playground, or spend the afternoon at the picnic areas, ball fields, and open lawns that overlook the wetlands and water. Watch sailboats drift by, spot local waterfowl, and take in the sight of watermen working the Bay — a living piece of Maryland's rich maritime heritage right in your own backyard. With direct access to the Chesapeake Bay, the water is always within reach for those who love to boat, fish, or simply soak in the coastal lifestyle. Schedule your appointment today and make Cedarhurst home!

1237 Spruce Ave, Shady Side

Listing courtesy of Blackwell Real Estate, LLC. Contact: 4432214120
$650,990
4 Beds ⋅ 3 Baths
December Delivery — the life you've been dreaming of is almost here! Welcome to Cedarhurst on the Bay, where every day feels like a coastal escape. This beautifully crafted home is the perfect blend of timeless charm and modern living, set against a backdrop of stunning Chesapeake Bay views that simply never get old. From the moment you arrive, the classic board-and-batten siding and striking exterior create an immediate sense of quality and character that carries beautifully throughout the entire home. Inside, soaring natural light fills the open-concept main level, where the dining area and family room connect seamlessly to create a warm, effortless flow perfect for both quiet evenings and lively get-togethers. The kitchen is nothing short of spectacular, featuring an oversized quartz island, stainless steel appliances, and generous cabinetry that makes cooking and entertaining an absolute pleasure. Need a dedicated workspace or a room to call your own? The main-level home office or flexible choice room delivers exactly that. Upstairs, the owner's suite is a true haven — bathed in natural light through large windows, complete with an expansive walk-in closet and a spa-inspired bath featuring a luxury shower that turns every evening into a retreat. Outside your front door, Cedarhurst's extraordinary four acres of community-owned waterfront property sets this neighborhood apart from anything else in the area. Sip your morning coffee as sunrises illuminate the Bay, stroll to the community center and playground, or spend the afternoon at the picnic areas, ball fields, and open lawns that overlook the wetlands and water. Watch sailboats drift by, spot local waterfowl, and take in the sight of watermen working the Bay — a living piece of Maryland's rich maritime heritage right in your own backyard. With direct access to the Chesapeake Bay, the water is always within reach for those who love to boat, fish, or simply soak in the coastal lifestyle. December will be here before you know it — schedule your appointment today and make Cedarhurst home!

1235 Spruce Ave, Shady Side

Listing courtesy of Blackwell Real Estate, LLC. Contact: 4432214120
$429,950
3 Beds ⋅ 3 Baths
Sleek Completely rebuilt and reimagined, this 3-bedroom, 2.5-bath cottage with a palette that feels equal parts cabin and studio. Every system, surface, and finish is new: Set on the West River/Chesapeake Bay peninsula in Avalon Shores of Shady Side — 25 miles south of Annapolis known for boating, crabbing, beaches and . This address puts you minutes from marinas, Franklin Point State Park, and bay sunsets, it's a rare combination of turnkey renovation and authentic bay-town character. Brand new Pella windows, roof and siding. Hardwood floors throughout. Stylish tile bathrooms. Brand new asphalt driveway. Bluestone steps with iron railings. Bright open floor plan. Double lot. Brand new electrical including heavy up panel, all new plumbing system and ductwork and HVAC equipment. Taken down to the studs with new insulation and drywall.

4922 Dogwood St, Shady Side

Listing courtesy of RE/MAX United Real Estate. Contact:

$399,000
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
$525,000
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
$149,500
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:

$1,100,000
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
$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:

$515,000
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
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