Shady Side Real Estate

Shady Side Real Estate

Welcome to Shady Side, Maryland—a hidden gem nestled in the heart of Anne Arundel County, where the charm of coastal living meets the tranquility of suburban life. This picturesque subdivision offers a unique blend of natural beauty, community spirit, and easy access to the vibrant attractions of the Chesapeake Bay.

Shady Side is renowned for its lush landscapes and serene waterfront views, making it a perfect retreat for nature lovers and outdoor enthusiasts. The area boasts an array of recreational opportunities, from kayaking in the bay to hiking along the scenic trails of nearby parks. Imagine weekends spent exploring the local marinas, enjoying fresh seafood at charming waterfront eateries, or simply unwinding on the sandy shores of the bay.

The community here is tight-knit and welcoming, making it an ideal place for families and individuals seeking a friendly atmosphere. With a variety of local events, farmers' markets, and seasonal festivals, residents have ample opportunities to connect and forge lasting friendships. The commitment to preserving the area's natural beauty is evident in the well-maintained parks and community spaces that invite residents to enjoy the outdoors.

Shady Side also offers convenient access to major highways, making it easy to commute to nearby cities like Annapolis and Washington, D.C., while still enjoying the peacefulness of a suburban lifestyle. Whether you are looking for a cozy cottage or a spacious family home, Shady Side has a diverse range of real estate options to suit your needs.

Discover the charm of Shady Side, where every day feels like a vacation, and the beauty of nature is just outside your door. Come explore this enchanting community and find your perfect home in this delightful corner of Maryland!

Newest Listings in Shady Side

$699,000
5 Beds 3 Baths
MAJOR PRICE IMPROVEMENT AND $5,000 SELLER CONTTRIBUTION TOWARDS BUYER'S CLOSING WITH ACCEPTABLE CONTRACT. Rare Opportunity with 2 detached homes on 4 Flat, Usable Acres in Shady Side! ​Welcome to 6066 Shady Side Rd, an incredible property offering endless versatility, income potential, and space to grow. Situated on 4 expansive, flat acres, this unique listing features two standalone ranch style homes, perfect for multigenerational living, live-and-rent setups, or investment portfolios. ​🏡 Main Residence (3 Beds | 2 Baths) ​Turnkey Interior: Beautiful updated finishes, including durable luxury vinyl plank flooring and modern recessed lighting throughout. ​Gourmet Kitchen: Bright and updated with crisp white soft close cabinetry, granite countertops, tile backsplash, and sleek stainless-steel appliances. ​Thoughtful Layout: Offers a dedicated laundry room, spacious living areas, and stylishly tiled bathrooms with modern vanities. ​Outdoor Living: Relax or entertain on the front deck, back deck, or under the convenient 2-car attached carport. ​🏡 Detached ADU / Guest House (2 Beds | 1 Bath) ​Private Setting: Tucked neatly at the rear of the lot with its own charming drive and mature tree-lined backdrop. ​Fully Equipped: Move-in ready home featuring an open-concept living area, dedicated kitchen space, and updated flooring. ​Income Potential: Ideal as a high-yield rental, guest house, home office, or private residence for family members. ​🌳 The Land & Potential ​4 Flat Acres: Massive, level lawn space ideal for gardening, outdoor recreation, or adding outbuildings/workshops. ​Future Investment: Flat topography provides great potential for future subdivision (buyer to verify local zoning/subdivision requirements). ​Whether you’re looking to offset your mortgage with rental income or searching for the ultimate multi-family retreat near the Chesapeake Bay, this property delivers unbeatable value and flexibility in Shady Side!

6066 Shady Side Rd, Shady Side

Listing courtesy of Century 21 Downtown. Contact:

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