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

$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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