Shady Side Homes for Sale

Shady Side Homes for Sale

Welcome to Shady Side, Maryland – a hidden gem nestled in the heart of Anne Arundel County. This picturesque waterfront community offers a unique blend of natural beauty, tranquility, and a warm sense of community. Known for its charming homes and stunning views of the Chesapeake Bay, Shady Side is the perfect place for those seeking a serene lifestyle while still being close to the vibrant city of Annapolis.

In Shady Side, you’ll find a diverse selection of homes for sale that cater to a variety of tastes and budgets. From cozy cottages to spacious waterfront properties, each home is designed to embrace the area's natural charm. Many residences boast beautiful outdoor spaces, perfect for entertaining or simply soaking in the serene surroundings. Imagine sipping your morning coffee while taking in the breathtaking sunrises over the bay or enjoying evening strolls along the scenic waterfront.

Living in Shady Side means embracing an active lifestyle with easy access to outdoor activities. The community is surrounded by parks, marinas, and beaches, making it ideal for boating, fishing, and hiking enthusiasts. The local atmosphere is friendly and inviting, with community events and gatherings that foster a strong sense of belonging.

With homes for sale in this idyllic area, now is the perfect time to discover the joys of Shady Side. Whether you're looking for a permanent residence or a charming vacation retreat, this community has something for everyone. Experience the peaceful lifestyle and natural beauty that Shady Side has to offer – you may just find your dream home here!

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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