Shady Side, MD Houses for Sale

*** HUGE PRICE IMPROVEMENT! SUNDAY, JULY 19, OPEN HOUSE, 12-2PM! ***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

Eric Hovanky Redfin Corp

Price reduction! 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,

Mary Gatton Redfin Corp

Fantastic opportunity to own your own land lighthouse-inspired round house with water views! Perfect serene retreat for the commuter and/or investment opportunity. Quiet neighborhood, blue heron sightings, and all the advantages of coastal living without the summer beach traffic. Freshly painted! This unique home features 3 bedrooms, 2 full bathrooms, an open-concept layout, and a spacious family

Melissa Wilson 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

Professional pictures coming!! Rarely available and proudly offered for the first time, this spacious split-foyer home is nestled on nearly a quarter-acre lot in the highly desirable water-privileged community of Cedarhurst. Lovingly maintained by its original owner, this well cared for residence offers 4 bedrooms, 3 full bathrooms, and multiple living spaces designed for both comfort and

John Tarpley Schwartz Realty, Inc.

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

This Stylish New home is move in ready and just in time to enjoy the summer breezes at the community Beach areas and play grounds! It is ready for your personal touch to make it your own! Main level features include Luxury Vinyl Plank flooring, 9' ceilings, Luxury kitchen with granite countertops, stainless steel appliances accented with sleek white cabinets with soft close drawers and a center

Paul Lee Long & Foster Real Estate, Inc.

Waterfront living with a private dock—all for under $800,000! Nestled in the charming Avalon Shores community, this beautifully updated coastal home perfectly blends classic elegance with modern comfort. The open-concept layout features two distinct living areas, ideal for both entertaining and daily relaxation. At the heart of the home is a premium kitchen equipped with granite countertops,

Jamie Angichiodo RE/MAX Leading Edge

Welcome to 4721 Oak Road, your waterfront paradise on the Chesapeake Bay! Nestled in the sought-after Felicity Cove community of Shady Side, this custom-built 2014 coastal home seamlessly blends modern luxury with effortless waterfront living. Boasting 4 spacious bedrooms, 3 full bathrooms, and 1,868 square feet of pristine living space, this residence shows like new. Step inside to an

Angie Carr Riverscape Realty

Opportunity awaits at this charming farmhouse nestled in the waterfront community of Shady Side. Situated on a spacious lot, this home offers a peaceful setting with convenient access to local marinas, parks, dining, and commuter routes. The interior presents a functional layout with generous living spaces, abundant natural light, and endless potential for customization. Enjoy the privacy of the

Brenda Sarver Maryland Realty Connection

Enjoy breathtaking views of the Chesapeake Bay from this charming home in the quaint waterfront community of Felicity Cove. The ground level features two bedrooms (one without a closet), a full bathroom, and a second kitchen, making it an ideal space for guests, extended family, or multi-generational living. The main living area is located on the second floor to take full advantage of the

Ray Mudd Schwartz Realty, Inc.

Coastal Affordable Living with a Boat Slip Included Discover the charm of Snug Harbor, where coastal living meets everyday affordability. This beautifully updated home offers gorgeous Chesapeake Bay views and the rare bonus of an included boat slip — making waterfront living more accessible than ever. Inside offers a light-filled floorplan, wide open living room, an open kitchen shines with

Sam Barbieri RE/MAX United Real Estate

Silver Water is a rare west-facing waterfront home designed in direct response to the Chesapeake—offering broad water views, remarkable sunsets, and a level of architectural clarity seldom found in the area. Set behind a private gate on a beautifully landscaped one-acre lot along the West River, the property combines seclusion with convenient access to Annapolis and Washington, DC. Spanning over

David Orso Berkshire Hathaway HomeServices PenFed Realty

Stately brick-front Colonial located in the highly sought-after water-privileged community of West River Estates. This absolutely gorgeous home offers exceptional space, charm, and amenities throughout. The beautifully appointed kitchen features granite countertops, double wall ovens, a large center island with built-in cooktop, and ample cabinetry. French doors open to a bright all-season

Ray Mudd Schwartz Realty, Inc.

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.

Agents - please see agent notes! Welcome to the rarely available water- privileged Cedarlea community in West River—Tucked away at the end of a quiet, family-friendly cul-de-sac, this beautifully maintained 4-bedroom, 2.5-bath home offers the perfect blend of comfort, space, and privacy and is ready for its new owners. From the moment you arrive, the inviting front porch sets the tone for relaxed

Stephanie Smith Douglas Realty, LLC

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.

COMING SOON - Great price for this exquisite, recently renovated coastal waterfront retreat offering a harmonious blend of luxury and comfort with abundant water views throughout. This home features three spacious bedrooms, one of which is conveniently located on the main level, and two elegantly appointed bathrooms, showcasing upgraded countertops and a walk-in shower. The open floor plan

Bill Beam Beam Realty Group, Inc.

6/26/26. Home is under roof ready for drywall. August delivery. Coastal Living Just Steps from the Chesapeake Bay! Schaefer Homes invites you to make this beautifully designed coastal-style residence your own located across the street from the bay offering nice water views. Offering over 3 stories of wide open living with time to personalize your selections so you can create a home that perfectly

Ray Mudd Schwartz Realty, Inc.

Own this home with no down payment required. This property qualifies for USDA and FHA solar+ financing, making homeownership attainable. This well-maintained home is located in an area eligible for a 100% USDA Zero-Downpayment Loan, providing a chance to buy a move-in ready home without the financial burden of a down payment. The home features a bright, open layout on a single level, designed for

Linda Pelton Taylor Properties

Rare 1-acre private lot located in sought after Idlewilde Acres backing up to Jack Creek Park! Upgrades include: 2023 enlarged rear decking, ADT Alarm system, generator hook up. 2023 full kitchen renovation - upgraded cabinetry, leathered granite counter-top, farmhouse sink, back splash upgraded stove top / microwave, and all new wood flooring on main level. Renovated half bath-2023. 2024 new

Steven Songer Maryland Waterfront Properties LLC

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 MC heavy commercial 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

George Heine Schwartz Realty, Inc.

New roof & gutters installed last week! Welcome to your own private waterfront retreat nestled at the peaceful head of South Creek, where breathtaking views, abundant wildlife, and the ultimate Chesapeake Bay lifestyle come together. Perfectly positioned on a beautifully level lot, this exceptional property offers a private pier ideal for launching a kayak, canoe, paddleboard, or boat, while the

Nicki Palermo RE/MAX One

6/29/26 DRYWALL INSTALLED. EXPECTED JULY/AUGUST 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

Ray Mudd Schwartz Realty, Inc.

Marlena McWilliams Keller Williams Capital Properties

REDUCED $45,000.00 ALL CASH OFFERS-FIRE DAMANGED INTERIOR- TOTAL REHAB-2 BR 1 Bath quiet secluded street. New Homes being built on same street.Owner reserves right to accept or reject any offer. Owner doing 1031 tax free exchange.Settlement 7-30 days.Haile Parkway/tax record Heile

Stephen Watson Flag Real Estate Inc.

There aren't many opportunities left to build brand new in Anne Arundel County at this price point, and 1430 Haile Parkway is one of them. Haile Parkway is quiet, wooded, and tucked into the laid-back charm of Shady Side, close enough to everything you need, far enough away to actually exhale. New construction at this level of quality and finish from one of the area's most respected builders is a

Lynn Peaper Hubble Bisbee Christie's International Real Estate

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.

TO BE BUILT – Exceptional Luxury Home with 1-Acre Waterfront Lot and Private Boat Ramp Experience the rare opportunity to build a custom luxury waterfront home just minutes to the Chesapeake Bay. Nestled on a tranquil wooded lot in West River, this stunning new construction residence offers the perfect blend of refined craftsmanship, modern comfort, and waterfront living. Thoughtfully designed

Michael Reible Realty Advantage of Maryland LLC

Welcome to this beautiful home in the highly sought-after Avalon Shores community, offered for sale by only its original builders of the home. 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

John Tarpley Schwartz Realty, Inc.

Tucked into the established Franklin Manor Beach community in Churchton, this 3-bedroom, 2.5-bath colonial delivers comfortable two-level living with one of the area's most appealing lifestyle perks, water access to the Chesapeake Bay just six blocks away, including a community pier on navigable water. The traditional floor plan makes the most of 1,679 square feet. A welcoming front porch sets

Kara Chaffin Donofrio Long & Foster Real Estate, Inc.