Shady Side, MD 2-Story Homes for Sale

This thoughtfully designed and 2022-built home blends modern finishes with a tranquil setting set against a backdrop of mature woods, creating a bright, open, and inviting space for both everyday living and entertaining. An open two-story foyer welcomes you inside to the main living area with vaulted ceilings, while 9' ceilings throughout the rest of the home enhance the airy, open feel. Charming

Mary Gatton Redfin Corp

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 Ma2 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.

George Heine Schwartz Realty, Inc.

Welcome to this inviting single-family home in the heart of Shady Side! This lovely residence features 3 bedrooms, 2.5 bathrooms, and approximately 2,235 sq ft of versatile living space — thoughtfully laid out to balance comfort and function.Step inside to a warm, open floor plan where natural light enhances every room, and an efficient layout makes everyday living easy. A well-appointed

Christine Saunders Compass

Experience Unmatched Privacy and Tranquility from this unique non-riparian waterfront home set on over 3+ scenic acres. Fall in love with sweeping water views and the serene presence of native wildlife—waterfowl, deer, eagles, and more—all just outside your door. Enjoy panoramic vistas of a natural pond, with the stunning Chesapeake Bay visible in the distance. On clear days, the Bay Bridge is

Ray Mudd Schwartz Realty, Inc.

HOME TO BE BUILT. EXPECTED LATE SUMMER 2026 DELIVERY. Schaefer Homes brings to you their latest Monroe model located in water privilege community offering community beach, pier, boat ramp, playground, slips, and more. Select from 3 exterior elevations! This home will come standard with plenty of upgraded features, and there is still the opportunity to make your personal selections to suit your

Ray Mudd Schwartz Realty, Inc.

4/3/26 Foundation started. EXPECTED SUMMER 2026 DELIVERY. Must use builder contract - buyer responsible for 100% transfer taxes**. Schaefer Homes brings to you their latest Monroe model located in water privilege community of Westelee offering community beach, pier, playground, boat slips, boat ramp and more. Select from 3 exterior elevations! This home will come standard with plenty of upgraded

Ray Mudd Schwartz Realty, Inc.

Truly special and exceptionally improved bayfront offering in the gated Columbia Beach community of Shady Side. This Classic Cape Cod is all about the experience and attention to detail—breathtaking Chesapeake Bay vistas, unforgettable sunrises and sunsets, and the kind of big-sky waterfront setting that makes this home feel like a retreat every single day. Seller has maintained detailed

Greg Fisk Douglas Realty, LLC

Shown by Appt only. Welcome to your own private retreat in sought-after West River Estates—where resort-style living meets everyday comfort. With access to a community pier, nearby marina, and surrounded by spectacular wooded views, this exceptional residence offers a seamless blend of indoor and outdoor living designed for both relaxation and entertaining. Step inside to a grand two-story foyer,

Nicki Palermo RE/MAX One

Welcome to Avalon Shores, a sought-after water-privileged community along the Chesapeake Bay offering the perfect blend of lifestyle and value. This freshly painted colonial is move-in ready and features 3 bedrooms, 2.5 bathrooms, and a two-car garage, all thoughtfully designed for comfortable everyday living. Situated on one of the larger lots in the community, the property offers a fully fenced

Nicki Palermo RE/MAX One

Investor special in the charming Columbia Beach community of Shadyside. This quaint 2-bedroom, 1-bath home offers great potential for investors, renovators, or buyers looking to create their own coastal retreat. Inside, you'll find classic panel walls, a cozy fireplace, and a bright sunroom that adds extra living space and character. Nestled in a peaceful setting near the water, this property is

Victoria Carmon-Brown Fusion Elite Realty

Waterfront opportunity along the West River, located in the Shady Oaks Manor community. Dock your boat at the private pier just off the large, flat lot and enjoy direct access to the water. From here, it is an easy ride out to the Chesapeake Bay and nearby waterfront towns. Inside, the home offers four bedrooms and three full bathrooms, including a primary bedroom with its own attached bath. The

Erica Baker TTR Sotheby's International Realty