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 charming waterfront community offers a unique blend of serene living and vibrant outdoor activities, making it an ideal place for families, retirees, and anyone seeking a peaceful retreat just a stone's throw away from the hustle and bustle of city life.

Shady Side is characterized by its picturesque landscapes, where lush greenery meets the sparkling waters of the Chesapeake Bay. Residents enjoy a tight-knit community atmosphere, complemented by friendly neighbors and a variety of local events that foster connections and camaraderie. The area is perfect for nature enthusiasts, with ample opportunities for boating, fishing, and hiking along the nearby trails. The local parks provide great spaces for picnics and outdoor gatherings, making it easy to enjoy the beautiful Maryland weather.

When it comes to homes for sale, Shady Side boasts an array of options to suit diverse tastes and budgets. From charming bungalows with waterfront views to spacious family homes nestled within peaceful neighborhoods, there’s something for everyone. Many properties feature modern amenities while retaining the quaint, coastal charm that defines the area. Whether you're looking for a cozy retreat or a place to raise a family, Shady Side's real estate market has much to offer.

Explore the possibilities in Shady Side today, and discover your perfect home in this idyllic community. With its stunning natural surroundings and welcoming spirit, Shady Side is more than just a place to live; it’s a lifestyle waiting to be embraced.

Newest Shady Side Homes for Sale

$699,900
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:

Start Your Search