Shady Side, MD Homes for Sale under $500,000

Coastal charm meets modern comfort in Avalon Shores! This sun-drenched, corner-lot 1940s cottage boasts beautiful water views from both floors. The inviting interior features a spacious kitchen with stainless steel appliances, while wrap-around windows flood the entire main living area with bright, natural light. Relax or entertain on the cozy screened-in front porch, or step out into the level,

Eric Hovanky Redfin Corp

Experience the best of the Chesapeake Bay in this 3-bedroom, 2.5-bathroom Colonial, in the sought-after Columbia Beach neighborhood! Nestled in a quiet, gated, water-privileged community, this home offers more than just a place to live—it offers a lifestyle complete with a private pier, boat ramp, tennis/basketball courts, and a playground. The heart of the home is the beautifully curated

Mike Benton Home Towne Real Estate

Welcome to 4909 Olive Street, a newer construction three bedroom, two and a half bath home in the waterfront community of Avalon Shores. Offering a functional layout, contemporary finishes, open living spaces, a fully fenced in backyard, and a private driveway. Avalon Shores residents enjoy access to a community beach, fishing pier, boat ramp, kayak launch, waterfront park, playground, basketball

Erica Baker TTR Sotheby's International Realty

Welcome home to this charming 3-bedroom, 1.5-bath detached home nestled in the sought-after water-privileged community of Avalon Shores! This move-in ready home features a bright and inviting kitchen, a spacious living room with easy access to the rear deck, and a fully fenced backyard that's perfect for entertaining, pets, or relaxing evenings outdoors. The maintained yard also includes a large

Jennifer Dickerson Home Sweet Home Real Estate LLC

Peaceful cul-de-sac setting, expansive covered porch, hardwood floors, and a spacious backyard just moments from the water.Set on a quiet street near the shoreline, this 3-bedroom, 2.5-bath home offers generous indoor and outdoor living in a location where wooded surroundings and nearby waterways create a slower pace of life. Inside, the main level has multiple living spaces that can easily

Chris Craddock EXP Realty, LLC

Enjoy water views and the best of coastal living in this charming home, ideally located in a private waterfront community with exclusive access to a boat ramp and sandy beach. The open-concept living and kitchen area creates an inviting space for everyday living and entertaining, while the large fenced backyard offers plenty of room for pets, play, and outdoor gatherings. A rare opportunity to

Maggie Richards Berkshire Hathaway HomeServices PenFed Realty

Perfect little rancher in a water access community. 3 bedrooms, 2 full baths, and a full fenced yard. Heated family/sun room out back and setup for a stackable washer/dryer inside.

Kyle Squires Lazar Real Estate

Welcome to Cedarhurst on the Bay, a charming waterfront community on the Shady Side Peninsula, conveniently located between Annapolis and Deale Maryland. This cute, updated rancher style home offers a rare affordable opportunity to enjoy Chesapeake Bay living, just one hour from the City. So much potential! Make it your weekend retreat, an Air B&B, or perhaps a tranquil place to retire, without

James Basuel Weichert, REALTORS

Welcome to this charming home located in a sought-after water-privileged community, just a short walk to the beach, boat slips, playground, boat ramp, and other neighborhood amenities. The main level features a spacious primary suite with a private full bath, offering convenient one-level living. The beautifully appointed kitchen boasts a center island with a gas cooktop, wall oven, abundant

Ray Mudd Schwartz Realty, Inc.

Welcome home to this beautiful brick-front Colonial nestled in the sought-after waterfront community of Back Bay Beach in West River! Just in time for summer, enjoy the ultimate Chesapeake Bay lifestyle with community access to a boat launch—perfect for launching your boat, jet skis, kayaks, and all your favorite water toys for endless days on the water. Situated on a spacious lot, this

Nicki Palermo RE/MAX One

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, a new roof, and fresh paint- 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

Juliet Patterson Samson Properties

Welcome to this beautifully maintained Colonial perfectly positioned on a desirable corner lot in the water-oriented community of Cedarhurst—where Chesapeake Bay living is part of everyday life. Just in time for summer, enjoy the opportunity to lease a boat slip for only $400 per year with direct access to the Chesapeake Bay, making weekends on the water easier than ever. Inside, you’ll find

Nicki Palermo RE/MAX One

Spacious 2,807 sq. ft. home offering exceptional potential for investors, multi-generational living, or rental income opportunities. The main residence features two bedrooms, one full bath, a kitchen, utility room, and a spacious family room with sliding doors leading to the rear deck. The attached in-law suite has its own private entrance and separate electric meter. Currently tenant-occupied by

Ray Mudd Schwartz Realty, Inc.

Welcome to this beautiful home in the highly sought-after Avalon Shores community, offered for sale by only its second owners. Situated on over one-third of an acre, this well-maintained 3-bedroom, 2.5-bath residence offers the perfect blend of comfort, space, and community living. The fully fenced backyard provides an ideal setting for entertaining, family gatherings, or simply relaxing

John Tarpley Schwartz Realty, Inc.