Shady Side Houses for Sale

Just minutes from Franklin State Park, the West River, and the Chesapeake Bay, this 4-bedroom, 2-bath Churchton home captures the essence of relaxed coastal living. Whether you're drawn to peaceful waters, community piers, bayside dining, or quaint local shops, this location offers it all. Step inside to a spacious main level with warm wood flooring and architectural columns that subtly define

Bob Lucido Keller Williams Lucido Agency

RARE FIND! WATERFRONT LIVING with a dock UNDER $1M! Welcome to 4922 Lerch Drive, a stunning 3-bedroom, 3-bathRENO VATED home built in 2005 that perfectly blends modern updates, natural light, and serene water views. This home is the ideal size—not too big, not too small—offering the perfect balance of comfort, function, and privacy!Step inside an inviting open-concept main level to find

Joan Stansfield Samson Properties

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 1037 Biltmore Ave — A Waterfront Dream in West River!Nestled in the peaceful and picturesque community of West River, this beautifully maintained home offers the perfect blend of comfort, style, and coastal living. Just steps from the water and minutes to the Chesapeake Bay, this property is ideal for those who crave serenity without sacrificing convenience.This

Matt Kalogeras Houwzer, LLC

This spacious 5 bedroom, 2 full bath split foyer is located in the highly desirable Community; Cedarhurst on the Bay. This remarkable property showcases the epitome of every day, vacation living with stunning views of The Chesapeake Bay. You will quickly be captivated by the grandeur that awaits you. The open layout seamlessly connects the living, dining and kitchen area, creating an ideal

Jessica Gosman-Bowen Curtis Real Estate Company

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.

Great New Price ... here is your chance to own and enjoy a coastal contemporary “cottage” with panoramic views and the soothing sounds of the Chesapeake Bay year round. This Bay fronting property has an open airy interior, warm and inviting, with two story vaulted ceilings, walls of windows which showcase the Bay view. The ease of main level living, enhanced with wood floors, includes the

Celeste Blessin Coldwell Banker Realty

Great Cape Cod on 4 lots with nice upgrades in beautiful gated beach community. Photos coming soon.

Lydia Newman Fairfax Realty Premier

Just two doors from the water and steps from a children’s park and boat ramp, this 3-bedroom, 2-bath rancher offers 1,408 sq. ft. of potential. Renovations are underway with many improvements already complete—kitchen updates started, dishwasher included but not yet installed, and bedrooms ready for new flooring. Enjoy a cozy fireplace, low-maintenance vinyl siding, attached garage, and a spacious

Shannon Thayer Douglas Realty, LLC

Charming 1BR, 1BA cottage in Avalon Shores—just a short stroll to the water! This cozy home was offers a perfect blend of comfort and convenience. Step inside to find a layout ideal for weekend getaways or year-round living. The Kitchen features stainless steel appliances and lots of counter space. The spacious fully fenced backyard is a standout, featuring two outbuildings—one perfect for a

Zachary Wyvill RE/MAX United Real Estate

Don't miss this charming and well-maintained home! The main level features stylish LVP flooring and a bright, sunny eat-in kitchen with granite countertops. A convenient powder room includes a new pedestal sink. Sliding door from the kitchen open to a deck that overlooks a fully fenced backyard—perfect for relaxing or entertaining. Upstairs, you’ll find two spacious bedrooms and a full bath. This

Ray Mudd Schwartz Realty, Inc.

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

Emily Motto Investors Management, Inc.

Welcome to Cedarhurst On The Bay — Your Bayside Retreat Awaits!Nestled in the serene, historic enclave of Cedarhurst On The Bay in Shady Side, Maryland, this beautiful single‐level home is the perfect blend of comfort, convenience, and coastal charm. Set on a generous double lot and built on a durable slab foundation, this residence offers 4 bedrooms, 1.5 bathrooms, and a thoughtfully

Vilas Wright Wright Real Estate, LLC

Charming Rancher Just Steps from the Bay Front!Nestled on a peaceful corner lot and surrounded by the serenity of a protected nature reserve, this inviting 3-bedroom, 1-bath single-level rancher offers the perfect blend of privacy, charm, and location. Just a short walk to the scenic bay front, you’ll enjoy the coastal lifestyle with morning strolls, sunsets, and water views just minutes

Nicole Hatch Samson Properties

Just Reduced, seller says sell! Welcome to this delightful coastal cottage nestled in the heart of the Columbia Beach community! Spacious wide beach, tot lot, tennis courts and basketball too. This beautifully updated home perfectly balances modern comfort with timeless charm. Offering two spacious bedrooms and a full bath, the layout is thoughtfully designed for easy living and effortless style.

Amy Juras Long & Foster Real Estate, Inc.

Calling all investors, second-home seekers, and visionaries—this is the project you’ve been waiting for! AND it just got better with a price improvement!! Located just steps from the water in the charming community of Idlewilde, this 2-bedroom cottage-style home sits on a rare double lot with Chesapeake Bay views from the backyard and access to fantastic community amenities.While the

Clinton Auman EXP Realty, LLC

Welcome to 1617 Winters Ave – Coastal Charm with Modern Updates in Idlewild on the BayBeautifully updated and move-in ready, this 3-bedroom, 2-bath gem is nestled in the water-access community of Idlewild on the Bay. Situated just one block from the Chesapeake Bay, this home boasts fresh interior updates, a fully fenced yard, and two spacious decks ideal for entertaining or relaxing by

John Kreamer Taylor Properties

Discover unparalleled luxury in this stunning Five bedroom, four and half bath waterfront home, offering two hundred and seventy feet of private shoreline and breathtaking views. Designed for refined living and effortless entertaining, this home delivers an exceptional lifestyle both inside and out. The exterior is a private resort, featuring a heated in-ground pool, outdoor grilling area, fire

Adam Light Monument Sotheby's International Realty

Coastal Living Meets Timeless Elegance on the Chesapeake BayEscape the hustle and embrace the peaceful rhythm of coastal life in this beautifully updated 5-bedroom, 3-bath Colonial, perfectly situated on a private 1.37-acre lot in the sought-after West River community. With over 3,000 sq ft of thoughtfully designed living space, this home offers the ideal blend of comfort, flexibility,

Bonnie O'Donnell RE/MAX One

Merchant Unmatched water views. Over 8,000 sq ft of curated living. A property that doesn’t just stand out—it stands alone.Tucked away in the quiet, rural charm of Shady Side, this architecturally bold residence offers year-round views of the West River and a lifestyle that feels worlds away—yet keeps you close to everything that matters. Step inside and you’re immediately immersed in

Phil Gerdes Real Broker, LLC - Annapolis

4 beds/ 1 full bath and 1/2 bath with shower.2144 SQ FT. Home and income opportunity goes with this four bedroom home on .57 acres of (C1B) commercial zoned property. Additional .375 acres and .1243 acres of (MA2) marine zoned property, totaling 1.0693 acres, with 135 feet of bulk headed waterfront, 200 foot pier, and 12 boat slips. Water depth from 4 to 8feet, that can accommodate boats in

George Heine Schwartz Realty, Inc.

To be built by Whitehall Building & Co., Annapolis’ largest luxury waterfront builder. Located in the desirable Columbia Beach neighborhood, this coastal-style home will offer over 3,700 square feet of finished living space and the rare combination of panoramic Chesapeake Bay views with the protection of a cove-front setting. Designed for modern waterfront living, the open-concept layout features

Lynn Peaper Hubble Bisbee Christie's International Real Estate

This charming 3-bedroom, 2-bath home offers the perfect blend of comfort, style, and location! Soaring ceilings in the primary suite with a private attached full bath. Featuring an open floor plan with hardwood floors, a spacious eat-in kitchen with updated cabinets and countertops, and plenty of room to entertain, this home is move-in ready. Nestled on a sought-after double lot, you’ll have the

Nicki Palermo RE/MAX One

Don't miss this wonderful opportunity to own this porch front home seated in an expansive private lot approximately 3.38 acres. Home features hardwood floors that flows from the combined living and dining rooms to the nice sized kitchen with appliances and main level bedroom and bath. There is a full bath on each level and three more bedrooms on the upper level. The sunroom with wide windows and

Gina Gargeu Century 21 Downtown