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

$375,000

3 Beds ⋅ 1 Baths

Own this home with no down payment required. This property qualifies for USDA and FHA solar+ financing, making homeownership attainable. This well-maintained home is located in an area eligible for a 100% USDA Zero-Downpayment Loan, providing a chance to buy a move-in ready home without the financial burden of a down payment. The home features a bright, open layout on a single level, designed for easy living. Positioned in the center of Churchton, this 3-bedroom coastal rambler includes a combined kitchen and dining area, spacious bedrooms, central air conditioning, public sewer, and a sizable third of an acre backyard well suited for summer gatherings. The property has been well cared for, allowing for immediate occupancy without significant renovations. Enjoy a tranquil, water-oriented lifestyle, just 1 to 2 miles from two popular waterfront locations: Franklin Point State Park, which offers over 470 acres of protected marsh, hiking trails, and wildlife viewing along the West River and Chesapeake Bay, and Jack Creek Park, which features walking trails, a secluded beach, and a launch site for kayaking, canoeing, and paddleboarding. Spend weekends enjoying boating, crabbing, or fishing, with convenient public boat launches, local marinas, and waterfront dining nearby. Experience the tranquility of a close-knit coastal community while still having an easy commute to Joint Base Andrews, the Annapolis waterfront, and the Washington Beltway, all without the hassle of an HOA.

5649 Shady Side Rd, Churchton

Listing courtesy of Taylor Properties. Contact:

$699,000

4 Beds ⋅ 2 Baths

4 Bedrooms/ 1 full bath and 1 half bath with shower. 2144 SQ Ft home and income opportunity goes with this home on .57 acres of C1B commercial zoned property. Additional .375 acres and .1243 acres of MC heavy commercial zoned property for a totaling 1.0693 Acres, with 135 feet of bulkheaded waterfront, 200-foot pier, with approximately 12 boat slips. Water depth from 4 to 8 feet that can accommodate 40ft+ boats. Total income for 2025 was $6900. with only a few slips rented. Will require a commercial lender or cash to purchase.

1462 Snug Harbor Rd, Shady Side

Listing courtesy of Schwartz Realty, Inc.. Contact:

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