Shady Side MD Real Estate & Homes for Sale

WATERFRONT LUXURY LIVING with panoramic West River views & unbelievable sunsets! This "3-year-young" custom home is perfectly positioned in the highly coveted community of Shady Side!! Designed for seamless indoor-outdoor coastal living. From the moment you step through the front door, the open-concept design draws your eye straight through to the water & pier - where your dock, boat lift, and semi-circle stone seating area /fire pit await for endless hours of fun & relaxation. The main level offers versatility with an elegant ensuite bedroom or office, recessed lighting and wide-plank hardwood flooring flows throughout the home for a clean, modern aesthetic (ZERO carpet anywhere). At the heart of the home, the chefs kitchen impresses with a massive quartz-topped island, stylish pendant lighting, and top-of-the-line appliances - including WOLF double ovens, a VIKING 6-burner commercial-grade gas cooktop, SUB-ZERO wine refrigerator, and DACOR dishwasher. A full suite of stainless steel appliances, a spacious pantry, and abundant custom cabinetry complete this showstopping space. High ceilings and a dramatic wall of windows span the rear of the home, filling the interior with natural light and framing breathtaking waterfront vistas. Beautiful transom windows line the staircase to the upper level, where youll find a spacious laundry room with cabinetry and a utility sink, along with three generous ensuite bedrooms. Each bath features granite-topped vanities, walk-in glass showers, and tile flooring - offering both luxury and privacy for family and guests. The primary suite is truly a retreat - expansive and light-filled, with a large walk-in closets featuring custom built-ins. The spa-inspired bath showcases dual vanities, a free-standing soaking tub with water views, a large walk-in shower with glass tile flooring and seamless sliding glass doors, tiled walls, a private water closet, and the second custom walk-in closet. Step outside and enjoy outdoor living at its finest on the waterside deck - perfect for morning coffee or evening cocktails. The covered front porch with handsome wood columns enhances the homes curb appeal, while Hardiplank siding ensures both durability and timeless charm. Additional highlights include storage beneath the porch, a storage shed, and a full-footprint concrete crawl space with interior access, offering exceptional storage options. From your backyard, take in views of the Chesapeake Yacht Club - accessible by jet ski, paddle board, kayak, or boat - and enjoy easy cruising to local favorites like Stan & Joes Riverside and Pirates Cove. Fish and crab right from your own dock, complete with a boat lift. Residents of Avalon Shores enjoy a wealth of community amenities, including two playgrounds, a ball field, beach and swimming area, boat ramp, and picnic areas - the perfect blend of luxury, leisure, and community. Just 25 minutes to Annapolis, 40 minutes to Washington, D.C., and 30 minutes from the Beltway, Shady Side offers a relaxed waterfront lifestyle with convenient access to city amenities. Enjoy beloved local spots like the Shady Side Market, The Driftwood Diner, Shady Side Soft Serve (the best!), and Renos, with even more shopping and dining nearby in Deale, Churchton, Edgewater, and Davidsonville.

Beautiful updated coastal cottage in the heart of Columbia Beach! *New roof 2023* This move-in ready 2-bedroom home features hardwood floors, a brand-new kitchen with stainless steel appliances, quartz countertops, and updated cabinets. Amazing loft area inside. Enjoy skylights and beautiful views. Beautifully landscaped level lot with a spacious back deck ideal for relaxing or entertaining. Enjoy exclusive community access to the Chesapeake Bay with a private boat ramp, pier, and beach. Close to Franklin Point State Park for even more outdoor fun. Fresh, bright, and full of charm this is coastal living at its best! Lot 28/29/30. All included for the sale.

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 modern luxury. Spanning over 2,200 square feet, the home features a main-level owners suite and high-end appointments throughout. Step inside to an inviting open-concept main level that includes a spacious family room with gas fireplace, a formal office with cathedral ceiling, a morning room nook, dining area, and a convenient half bath. The gourmet kitchen is a true showpiece, featuring a large center island with breakfast bar, soft-close shaker cabinetry, open apron farmhouse sink, quartz countertops, subway tile backsplash, and a five-piece stainless steel appliance package including a wall oven, cooktop, and range hood. The main-level owners suite offers a walk-in closet and a luxury ensuite bath with dual vanities and an expansive 7x6 spa shower with dual shower heads. Upstairs, youll find two additional bedrooms and a second full bath. Additional highlights include LVP flooring throughout the main level, ceramic tile in all baths and the laundry room, public sewer, 30-year architectural shingles, a 92% efficient Carrier HVAC system, 2x6 framing, R49 ceiling insulation, R21 wall insulation, and an air seal package. Outdoor spaces include a 246 square foot paver patio and a spacious wrap-around front porch. With no HOA or restrictive covenants, this home offers rare flexibility and freedom in a highly desirable Anne Arundel County location, convenient to both Annapolis and Washington, D.C.

Welcome to 4950 W End Ave - a charming coastal bungalow just steps from the Chesapeake Bay! This beautifully renovated home perfectly blends modern updates with relaxed bay-side living. Set on a total of .242 acs (additional lot included total), this property offers serenity, space, and privacy. Step inside to an open and airy floor plan filled with natural light. Warm hardwood floors, a soft coastal palette, and stylish finishes create a space that feels both fresh and welcoming. The updated kitchen features sleek gray cabinetry, butcher block counters, a full pantry, and an easy flow into the dining and living areas - perfect for entertaining or everyday comfort. The main level bedroom and renovated bath offer convenience, while the upper-level suite provides a personal retreat with a private bath. A new mini-split system adds year-round comfort and energy efficiency. Outside, enjoy ample parking, a spacious yard, your own putting green, a large storage shed, newer deck, and your own personal boat slip - ready for your next day on the water! Whether hosting summer cookouts or relaxing after a day on the bay, youll love the laid-back seaside vibe this property delivers. Located in a water-privileged community offering a bayside pier, boat ramp, and entertaining areas, youll experience the best of Chesapeake living right at your doorstep. Ideal as a full-time residence, weekend getaway, or vacation investment.

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 even within sight. The home features a relaxing screened porch, a spacious kitchen that flows into a cozy living area with a wood stove-perfect for chilly evenings. The main level includes a bedroom and full bath, plus an additional room ideal for an office or second living space, also with a wood stove. Upstairs, the primary bedroom offers breathtaking water views, accompanied by another bedroom and a full bath. A barn/stable on the property makes it ideal for horses or a home-based business with office space. This is truly a one-of-a-kind property-peaceful, picturesque, and full of potential. Come see it for yourself.

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 beauty-with low maintenance. Just a short walk to the bay front, youll love starting your mornings with coastal breezes and winding down with sunset walks to the community pier. Inside, enjoy a warm and inviting open layout, complete with a cozy wood stove and a splash of personality from the bright red front door. Major updates-roof, HVAC, water softener, and well pump-all done within the last 3 years-mean you can move in and relax from day one. The manageable yard has 2 sheds for extra storage and a roomy driveway (with space for a boat or guests), and surrounding greenery make outdoor living simple and serene. Plus, the neighboring nature reserve means no new development next door-ever. If youre ready to downsize to comfort, convenience, and coastal charm, this is the home for you.

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 offers both privacy and functionality. Step onto the welcoming front porch and into a thoughtfully designed main level featuring a private office, formal dining room, and a spacious family room highlighted by large picture windows and a modern gas fireplace. At the heart of the home, the gourmet kitchen impresses with premium quartz countertops, herringbone tile backsplash, tasteful dove and pistachio cabinetry with dovetail joints and soft-close drawers, a walk-in pantry, farmhouse apron sink, and a large island with breakfast bar. Upstairs, the primary suite overlooks the private backyard and features luxury vinyl plank flooring, a walk-in closet, and a spa-inspired bath with a 7x6 walk-in shower boasting floor-to-ceiling tile. Additional highlights include 7-inch LVP flooring throughout the main level, shake siding with stone column bases, 2x6 construction, a 92% efficient HVAC system, and 30-year architectural shingles. With no HOA or restrictive covenants, this home offers rare flexibility and freedom in a highly desirable Anne Arundel County location, convenient to both Annapolis and Washington, D. C.

Amazing opportunity to own a beautifully remodeled home in the waterfront community of Idlewilde by the Bay in Shady Side. Just steps from the Chesapeake Bay, this 4-bedroom, 2-bath home offers approximately 1,300 square feet of modern living with a brand-new signature designer kitchen featuring an eat-in island, new appliances, and high-end finishes throughout. The spacious primary suite provides a comfortable retreat, while three additional bedrooms offer flexibility for guests, a home office, or hobbies. Every detail of this home has been thoughtfully updated, making it completely move-in ready. The property includes a large backyard with a shed for extra storage. The Idlewilde community features a community pier and access to activities such as walking, boating, kayaking, and fishing. Enjoy the peaceful, active lifestyle of Shady Side with local marinas, golf courses, and restaurants nearby - all just 20 miles south of Annapolis and the U.S. Naval Academy. Welcome home to Shady Side! ** Please contact the co-listing agent for details **

10/10/25 Update: Home is under roof. Estimated completion is projected for January/February 2026. 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� cabinets offering both elegance and practicality. The kitchen seamlessly connects to the dining area and expansive great room, creating an ideal space for hosting gatherings or relaxing with family. Upstairs, youll find a spacious primary suite with a private en suite bath, along with three additional bedrooms, a full guest bathroom, and a conveniently located laundry room. Community offer beach, playground, pier, boat ramp and more. Disclaimer: Renderings and photos are for illustrative purposes only and may show optional features, upgrades, or configurations not included as standard. Actual features, finishes, and layouts may vary.

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 open-concept living space featuring vaulted ceilings, hardwood floors, and a gas stand-alone fireplace that adds warmth and character. The loft area provides flexible space for guests, a home office, or a quiet reading retreat-and includes its own powder room for added convenience. Step outside to a spacious deck where you can relax and listen to the water lap against the bulkhead, or take a short stroll to enjoy the communitys private waterfront access. Whether you're seeking a weekend getaway or a full-time coastal lifestyle, this Cottage by the Bay is a rare opportunity to own in one of the area's most desirable waterfront neighborhoods. Schedule your private tour today and experience the magic of Columbia Beach!

Just two doors from the water and steps from a childrens 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 a fresh and updated space to make their own. Enjoy a cozy fireplace, low-maintenance vinyl siding, attached garage, and a spacious 0.29-acre lot. A perfect opportunity to finish your dream home in a sought-after water-access community!

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 bath. Two additional bedrooms and a second full bath provide plenty of space for family or guests. Additional highlights include a two-car garage, a two-car carport, a large storage shed, and a handicap-accessible ramp. Situated on a level, usable one-acre lot, this home combines comfort, functionality, and outdoor space in a peaceful setting.

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 singleâ??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 laidâ??out floor plan thats moveâ??in ready-with energyâ??saving solar panels already in place. Enjoy all that the sought-after Cedarhurst On The Bay community has to offer, including a waterfront pier, boat slips, community center, playground, and open green spaces with stunning bay views. A rare find offering coastal living and neighborhood charm. With modern updates, waterfront access, stellar neighborhood amenities, and solar energy features, this is more than a property-its a lifestyle. Ready to embrace a serene yet spirited coastal community? Lets bring you home.

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 3,700 sqft of 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 soaring 10' ceilings on the main level and walls of glass to showcase the water views. With 4 bedrooms, 3.5 baths, and high-end finishes throughout, this home is both elegant and functional. Enjoy community amenities like a boat launch, pier, tennis and basketball courts, playgrounds, and more. Ideally situated with convenient access to Annapolis, DC, and Baltimore. Still time to customize! Buyers can choose their selections and finishes.

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 environment for entertaining family and friends. The kitchen is a chef's delight including ample storage space. The primary and additional bedrooms offer comfort and privacy for the entire family. Experience outdoor living at its finest in the expansive backyard. Whether you're hosting summer cookouts or simply enjoying an evening under the stars on your deck with spectacular views; the possibilities are endless. The community beach, marina, pier, boat ramp, playground and more are just steps away!! Welomce Home to 1220 Grove Ave.

Calling all investors, second-home seekers, and visionaries-this is the project youve 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 property needs renovation-including electric installation, structural repairs, and cosmetic updates-the bones are there and the potential is undeniable. Whether you are looking to build instant equity, create a weekend getaway, or flip for profit, this home offers the canvas to make it happen. Enjoy the laid-back waterfront lifestyle with access to a community fishing pier, open lawn area, beach, and playground just down the street. A newer well is already in place, adding to the property's value and convenience. This is not just a project-its a chance to create something special in a peaceful coastal setting. Bring your vision, your toolbox, and your ambition. Properties with this kind of potential in Shady Side do not last. Schedule your showing today and turn this opportunity into your next success story. **Please note square footage is estimated, buyer to perform own due diligence**

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 stainless steel appliances. Both bathrooms have beautiful ceramic tile and luxury vinyl flooring. The yard is fully fenced and includes a detached garage with off street parking. The community pier, which is a 2-minute walk, is on the Chesapeake Bay and has amazing views of the Bay Bridge. The Idlewilde community is a peaceful retreat location that is close to many shops and restaurants.

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. Upstairs features four bedrooms, including a primary suite with views of both the Bay and Flag Pond, plus an en-suite bath, three additional bedrooms, and a full hall bath. A two-car garage includes an extra storage room. Brand new a/c. While the home could use some updating and TLC, it presents a fantastic opportunity to make it your own. Located in a vibrant waterfront community with amenities such as a boat ramp, pier, tennis courts, and more. Come experience the Chesapeake Bay lifestyle.

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 lots of natural light has a great view of the backyard and leads to the rear deck, which is a perfect spot for outdoor fun. The rear exterior includes a 3-car detached garage with large workshop and an unfinished upper level. Home is located in a water-oriented community and is conveniently close to the beach, marina and Shady Side attractions. NOTE - Buyers winning the Highest & Best must understand that they participated in a Highest & Best, Multiple Offers Situation and that any requests to the Seller for Special Concessions, Repairs or Switch in Financing could result in the Seller terminating and retaining Buyer's EMD.