Shady Side, MD Homes 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

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

Westelee Welcome's You Home! This 2.5 year old "Pottery Barn" Colonial home is set perfectly on a corner lot with views of the West River. This home has 4 bedrooms and 2.5 baths. Patio was just put in and a 6 foot privacy fence around the backyard in 2024. GREAT FOR HAVING A CRAB FEAST IN THE SUMMER OR BONFIRES IN THE FALL. THIS YARD IS GREAT FOR ENTERTAINING BRING YOUR FAMILY AND FRIENDS. There

Carey Laycock RE/MAX Leading Edge

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 retreat 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

Welcome to 4717 Frederick Avenue — a charming and updated cottage just two blocks from the West River in the Idlewilde on the Bay community. This 2-bedroom, 1-bath ranch-style home offers comfortable one-level living with thoughtful improvements throughout. Step inside to a bright, open living area featuring neutral finishes and a cozy fireplace, ideal for everyday relaxation. The renovated

James Weiskerger Next Step Realty

Rare Shady Side opportunity on 1.58 acres near the Chesapeake Bay. 1451 Shady Rest Rd offers a partially constructed home where building began pre-Covid. The property is ready for a new owner to bring their vision. It includes a permitted 3-bedroom septic system and an operational well, giving you a strong foundation for your new build. In this highly desirable South County area, buyers are

Teal Clise EXP Realty, LLC

Home Sweet Home! Come tour this 2 level, 3 bedroom, 2 full bath just a couple blocks to the water. Situated in Columbia Beach, feel like you're vacationing year round! Whether your taking a walk in the gated community, or entertaining in the spacious home, you'll enjoy living here! No HOA. Please read agent remarks.

Cheryl Bare CENTURY 21 New Millennium

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

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

Welcome to a home that doesn’t just offer a place to live—it offers a lifestyle on the Chesapeake Bay. As you approach the property, the experience begins immediately. The driveway and gated entry set the tone, leading you toward a waterfront sanctuary where every detail elevates coastal living. This home sits directly on the water, complete with a slip and a finger pier, so you can tie up your

Lily Vallario EXP Realty, LLC

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

Experience refined living in this beautifully maintained 3-bedroom, 2.5-bath Colonial, perfectly nestled on a quiet, tree-lined street. This distinguished residence offers timeless curb appeal with a welcoming front porch, a thoughtfully designed interior, and a nicely appointed kitchen ideal for both daily living and entertaining. The home features a spacious primary suite, generously sized

Diego Reyes Long & Foster Real Estate, Inc.

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.

For buyers desiring a quicker move-in, this same model is under construction less than a mile away and will be completed in approximately 30 days — a perfect opportunity to preview the craftsmanship and finishes in person. This to-be-built custom Arts & Crafts residence by local builder Laine Street Homes blends timeless design with modern luxury. Set on a premium 1.5-acre homesite, the property

Joshua Mast HomeSource Pro Real Estate

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.

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. New flooring will be installed throughout the home prior to closing, offering buyers

Shannon Thayer Douglas Realty, LLC

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

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

JANUARY 2026 DELIVERY. Introducing the Adams model — a beautifully designed home featuring an open-concept floor plan that blends comfort, style, and functionality. At the center of the home, the gourmet kitchen boasts a large island, stainless steel appliances, a walk-in pantry, and premium finishes—perfect for everyday living and entertaining alike. Additional kitchen upgrades include 42”

Ray Mudd Schwartz Realty, Inc.

Coastal Living in a Gated Waterfront Community a Short Distance from Annapolis and Washington, D.C. Awaits You!Discover the perfect blend of charm and comfort in this 2-bedroom, 1.5-bath Cottage by the Bay, located in the desirable gated waterfront community of Columbia Beach. With stunning bay views, this home offers a peaceful escape just steps from the water.Inside, enjoy an

Stephanie Burns Coldwell Banker Realty

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.

For buyers seeking a quicker move-in, the same model is currently under construction less than a mile away and will be completed in approximately 30 days, offering the perfect opportunity to preview the craftsmanship and finishes in person or purchase if a faster timeline is preferred.This to-be-built Modern Farmhouse by local builder Laine Street Homes blends timeless architecture with

Joshua Mast HomeSource Pro Real Estate

Welcome to this charming 2-bedroom, 2-bath home in the water-oriented community of Avalon Shores. Perfect for those looking to start out, scale down, or a second home! Freshly updated with new flooring and pain- this home is truly move-in ready! Enjoy a fully renovated bathroom, a spacious deck, and a fully fenced backyard—perfect for pets, gatherings, or quiet relaxation.Step outside and

Juliet Patterson Samson Properties