Shady Side Homes for Sale

Shady Side Homes for Sale

Welcome to Shady Side, Maryland – a hidden gem nestled along the picturesque shores of the Chesapeake Bay in Anne Arundel County. This charming waterfront community offers a unique blend of tranquility and adventure, making it the perfect place for families, retirees, and nature lovers alike. With its lush greenery, serene landscapes, and stunning water views, Shady Side is a peaceful retreat from the hustle and bustle of city life.

As you explore this quaint subdivision, you'll discover a variety of homes for sale that cater to diverse lifestyles. From cozy bungalows to spacious family homes, each property reflects the warmth and character of the community. Many homes boast modern amenities and designs while still maintaining the charm of the area. Imagine waking up to the gentle sounds of nature and sipping your morning coffee on a deck overlooking the bay – this is the lifestyle that Shady Side offers.

Outdoor enthusiasts will appreciate the nearby parks, nature trails, and access to water activities such as boating, fishing, and kayaking. The community is also known for its friendly neighbors and a strong sense of camaraderie, making it easy to feel at home. With local shops, restaurants, and schools just a stone's throw away, Shady Side provides the perfect balance of seclusion and convenience.

If you’re searching for a home that combines the beauty of nature with a close-knit community spirit, look no further than Shady Side. Explore our listings today and discover your dream home in this enchanting corner of Maryland!

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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