Shady Side, MD Homes for Sale

This spacious and well-maintained home offers the ease of one-level living at it's best. The modern kitchen opens to a cozy family room featuring a gas fireplace and a sliding door that leads to a stunning sunroom and adjacent deck—perfect for relaxing or entertaining. Enjoy formal spaces with both a living room and dining room, along with a generous primary suite complete with a private full

Ray Mudd 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

Stunning 4BR / 2.5BA home at 4951 Dogwood Street, Shady Side — freshly painted, bright, open living with a private pool, oversized deck ideal for entertaining, 6‐ft privacy fence, and a 2‐car garage. Spacious primary suite, 3 other large bedrooms, abundant storage and finished living spaces create a turnkey Chesapeake retreat.Enjoy direct access to swimming, crabbing, fishing, water skiing

Carey Laycock RE/MAX Leading Edge

Nestled between serene waters, this home offers stunning, unobstructed views of Flag Pond from the rear and views of the Chesapeake Bay from the front. Enjoy watching local waterfowl and soaking in the natural beauty from every angle. Inside, the spacious kitchen opens to the family room, perfect for gathering, along with a formal living room and a main-level office or potential 5th bedroom.

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.

To be built by Whitehall Building & Co., Annapolis’ leading luxury waterfront builder. Set within the sought-after Columbia Beach community, this coastal-style home captures the best of Chesapeake Bay living with panoramic views and the rare protection of a cove-front setting. With Whitehall, the path to building is refreshingly simple. Their step-by-step process begins with a complimentary

Lynn Peaper Hubble Bisbee Christie's International Real Estate

Peaceful Living by the Bay – Perfect for Downsizing! Looking to simplify without sacrificing charm or location? This move-in ready 3-bedroom, 1-bath rancher is the ideal opportunity for anyone craving a slower pace, less maintenance, and more time to enjoy the good life. Tucked on a quiet corner lot next to a protected nature reserve, this single-level home offers peace, privacy, and natural

Nicole Hatch Samson Properties

Estate sale handled by an attorney. This well-loved home has been in the same family since 1953 and is now ready for its next chapter. Offering generous living space and abundant potential, this property is ideal for buyers looking to build sweat equity and restore its original charm. Situated on a large lot, the sale also includes an additional 25' x 100' parcel located to the right of the home.

Ray Mudd Schwartz Realty, Inc.

Welcome to a home that feels as good as it looks. This fully renovated 3-bedroom, 2-bath residence offers the charm and comfort of coastal living with no HOA. From the moment you walk in, the open floor plan space feels inviting, thoughtfully laid out, easy to live in, and designed to make everyday life feel a little more relaxed. The primary suite had an extension done, creating a spacious and

Jonathan Vanegas Samson Properties

Welcome to 1330 Jordan Drive, a charming 3-bedroom, 2.5-bathroom home nestled in the highly desirable Avalon Shores community in Shady Side, Maryland. This well-maintained home strikes the perfect balance between comfort and character. The covered front porch invites you to unwind and enjoy seasonal water views, setting the tone for peaceful, waterfront living. Inside, you’ll find a bright, open

Emily Motto Investors Management, Inc.

SHORT SALE APPROVED AT LIST PRICE! This charming three-bedroom, one-bathroom house presents an exceptional investor opportunity in peaceful Shady Side. The property offers excellent renovation potential, allowing you to customize and add value while creating possible rental income streams. Enjoy convenient parking and generous outdoor space perfect for relaxation or entertainment. The spacious

Cindy Martin Samson Properties

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.

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.

Perfect time to buy this updated home with a detached garage in the beautiful Chesapeake Bay front communnity of Idlewilde! Main level bedroom and full bathroom, waterview from front second level bedroom, and off street parking. This home has been completely updated with the main level having luxury vinyl flooring and fresh paint. The spacious kitchen has granite countertops, wood cabinets, and

Sheri Stevens Samson Properties