Shady Side Homes for Sale

Shady Side Homes for Sale

Welcome to Shady Side, Maryland—a picturesque waterfront community nestled in the heart of Anne Arundel County. This charming subdivision is not just a place to live; it’s a lifestyle choice for those seeking tranquility and natural beauty. With its stunning views of the Chesapeake Bay, Shady Side offers a unique blend of small-town charm and modern conveniences, making it an ideal location for families, retirees, and everyone in between.

The community is characterized by its friendly atmosphere, where neighbors know each other by name and outdoor activities abound. Residents enjoy easy access to local parks, marinas, and nature trails, perfect for boating, fishing, or simply soaking in the serene surroundings. The area is also known for its rich history, with quaint shops and eateries that reflect the local culture.

Currently, there are a variety of homes for sale in Shady Side, catering to diverse tastes and budgets. From cozy cottages to spacious waterfront properties, you’ll find a range of options that offer both comfort and style. Many homes feature modern amenities while retaining their classic charm, allowing you to enjoy the best of both worlds. With a strong sense of community and an abundance of outdoor activities, Shady Side is not just a place to live—it's a place to thrive.

If you’re looking for a slice of paradise where you can relax and enjoy the beauty of nature, explore the homes for sale in Shady Side today, and discover your dream home in this enchanting Maryland community!

Newest Shady Side Homes for Sale

$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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