Shady Side MD 4 Bedroom Real Estate, Homes, Condos for Sale

Come Live the Bay Lifestyle! Welcome to 1244 Pine Avenue, a charming Chesapeake Bay retreat in Shady Side, Maryland, offering beautiful water and marina views, exceptional outdoor living, and the relaxed charm of coastal Maryland. Wake up to breathtaking sunrises, watch sailboats pass by, and enjoy peaceful evenings overlooking the bay. Located in the desirable Cedarhurst community, this inviting home offers the perfect opportunity to embrace waterfront living with a residents only marina across the street. Inside, the light filled living and dining areas feature a fireplace and expansive picture windows framing beautiful water views. The updated kitchen is appointed with green cabinetry, granite countertops, stainless steel appliances, and a gas range. Just beyond, a charming screened-in porch creates the perfect setting for morning coffee or al fresco dining. The spacious rear family room offers additional living space with sweeping bay views and sliding glass doors opening to the deck and fully fenced backyard, creating a seamless connection between indoor and outdoor entertaining. The main level includes a versatile bedroom ideal for guests or a home office, while upstairs, three generously sized bedrooms offer comfortable accommodations, including a spacious primary bedroom with beautiful Chesapeake Bay views. Additional highlights include a newer roof, new washer and dryer, generous outdoor entertaining areas, and a large storage shed is wired and has electricity. For boating enthusiasts, the nearby residents only marina offers boat slips reportedly available for $350 annually, providing convenient access to the Chesapeake Bay. Cedarhurst's waterfront community center, playground, beach, and picnic areas further enhance the neighborhood's coastal lifestyle. Whether as a primary residence or weekend retreat, 1244 Pine Avenue offers an exceptional combination of water views, generous outdoor living, boating access, and the tranquility of Shady Side's beloved Chesapeake Bay community.

1244 Pine Ave, Shady Side

Listing courtesy of Compass. Contact:

$499,900

4 Beds ⋅ 3 Baths

Nestled in the charming Cedarhurst on the Bay community, this delightful split foyer home offers a perfect blend of comfort and convenience. This well-maintained residence features four spacious bedrooms and three full bathrooms, ideal for both relaxation and entertaining. Step outside to discover a serene outdoor oasis, complete with a hot tub for unwinding after a long day. The property also includes a garage and a shed, providing ample storage for all your needs. Enjoy the beauty of nature with easy access to the stunning Chesapeake Bay, where community docks invite you to explore the water and create lasting memories. The neighborhood is known for its friendly atmosphere and strong sense of community. Residents benefit from nearby parks, perfect for leisurely strolls or picnics, and excellent public services that enhance the quality of life. With a walkout basement and a cozy fireplace, this home is designed for comfort and warmth. Experience the joys of living in Cedarhurst on the Bay, where community spirit meets the tranquility of waterfront living. This home is not just a place to live; it's a place to thrive. professional pictures to come.

1183 Cedar Ave, Shady Side

Listing courtesy of United Real Estate Premier. Contact:

$574,990

4 Beds ⋅ 3 Baths

Home is ready for immediate occupancy. 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 LVP flooring through out (Carpet in 2 bedrooms). From the classic board-and-batten siding to the welcoming front porch, the exterior sets a striking first impression. Upper level offers water views and an open-concept layout that seamlessly connects the dining and family rooms, offering the perfect setting for everyday living or entertaining. At the heart of the home is an upgraded kitchen with oversized island, upgraded countertops, stainless steel appliances, and abundant cabinetry—ideal for casual meals or gatherings with friends. A private home office (or flexible choice room) on the main level adds convenience, while upstairs the serene owner’s suite boasts a large picture window with Bay views, a spacious walk-in closet, and a spa-inspired bath with a luxury shower. Walk to community pier, boat ramp, playground, tennis courts and more. 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. Flood insurance is approximately $650.00 year. $5,000 in closing assistance with preferred lender and title company.

5314 Al Jones Rd, Shady Side

Listing courtesy of Schwartz Realty, Inc.. Contact:

$599,990

4 Beds ⋅ 3 Baths

Huge Price Adjustment + $5,000 Closing Help! December Delivery at Cedarhurst on the Bay* Welcome to Cedarhurst on the Bay, where every day feels like a coastal escape. This beautifully crafted home blends timeless charm with modern living, with stunning Chesapeake Bay views and classic board-and-batten siding. The open-concept main level is filled with natural light, connecting the dining area and family room. The kitchen features an oversized quartz island, stainless steel appliances, and generous cabinetry, and a main-level home office or flex room adds versatility. Upstairs, the owner’s suite offers large windows, an expansive walk-in closet, and a spa-inspired bath with a luxury shower. Outside, Cedarhurst’s four acres of community-owned waterfront include a community center, playground, picnic areas, ball fields, and open lawns overlooking the wetlands and water. With direct access to the Bay, boating, fishing, and sunset views are always within reach. December will be here before you know it. Don’t wait. Schedule your appointment today! *Closing cost assistance terms and conditions apply.

1235 Spruce Ave, Shady Side

Listing courtesy of Blackwell Real Estate, LLC. Contact:

$549,990

4 Beds ⋅ 3 Baths

Move-In Ready — and the Chesapeake Bay lifestyle is calling your name! Nestled in the waterfront community of Avalon Shores, this beautifully crafted home offers the rare combination of coastal charm, and modern elegance — all ready for you to enjoy from day one. As an added bonus, the builder is currently offering $5,000 in closing cost assistance with the use of a preferred Lender and Title Company — speak with sales for details! From the moment you arrive, the classic board-and-batten siding and welcoming front porch set the tone for the warmth and character found throughout. Step inside to a bright, open-concept layout where the dining area and family room flow effortlessly together — a natural setting for both lively entertaining and relaxed everyday living. The heart of the home is a stunning kitchen showcasing an oversized quartz island, stainless steel appliances, and abundant cabinetry that perfectly balances beauty and function. A main-level home office or flex room rounds out the main level, offering the ideal space for working from home, a quiet reading nook, or whatever your lifestyle calls for. Upstairs, retreat to a truly spectacular owner's suite featuring a large picture window, an expansive walk-in closet, and a spa-inspired bath with a luxury shower designed to help you unwind in style. Step outside and discover the incredible lifestyle that makes Avalon Shores so special. Enjoy a community harbor, complete with 60 boat slips and direct access to the Chesapeake Bay — a dream come true for boating enthusiasts and coastal living lovers alike. Just a short stroll from your front door, four acres of community-owned waterfront await, offering panoramic Bay views, open lawns, wetlands, picnic areas, playgrounds, ball fields, and the simple joy of watching sailboats, waterfowl, and local watermen drift by. This is more than a home — it's a lifestyle. Come experience everything Avalon Shores has to offer and make it yours today!

1225 Juniper St, Shady Side

Listing courtesy of Blackwell Real Estate, LLC. Contact:

$514,000

4 Beds ⋅ 3 Baths

Now is the time to take a fresh look at this beautifully designed 2022-built home, where modern style, thoughtful details, and a peaceful wooded setting come together. Move-in ready and filled with natural light, this home offers the space and flexibility buyers are looking for—without the wait or expense of new construction. Step inside to an open two-story foyer and into the inviting main living area with vaulted ceilings. Nine-foot ceilings throughout the home, charming cottage-style windows, and an open layout create an airy, comfortable feel. LVP flooring flows throughout the living room, kitchen, and wide hallway, making everyday living and entertaining effortless. The kitchen is a standout, featuring granite countertops, soft-close cabinetry, oil-rubbed bronze fixtures, and a center island with seating. There’s plenty of room for a dining table, creating an easy gathering space for family and friends. The main level offers three bedrooms including a spacious owner’s suite with two closets providing excellent storage, while the distinctive en-suite bath features dual sinks, granite countertops, a walk-in shower, custom wall trim. The two additional bedrooms feature custom molding, decorative wall treatments, and stylish finishes. The hall bath includes a granite vanity and shower/tub combination. And there’s even more living space downstairs! The lower level features a large recreation room with sliding glass doors to the backyard, a flexible fourth bedroom perfect for guests, a home office, gym, or hobby room, plus another full bath. This versatile lower level gives you room to spread out, work from home, entertain, or accommodate overnight guests. Outside, raised garden beds are ready for your favorite flowers, herbs, and vegetables. The mature, wooded backdrop provides a peaceful sense of privacy and a beautiful setting to enjoy year-round.

1411 Haile Pkwy, Shady Side

Listing courtesy of TTR Sotheby's International Realty. Contact:

$625,000

4 Beds ⋅ 2 Baths

There is something special about life near the Chesapeake Bay—and 1221 Bast Lane captures it beautifully. Completely remodeled from top to bottom, this charming one-level Coastal Craftsman combines fresh, sophisticated interiors with incredible outdoor space and one of the most impressive detached garages you will find. Set on a beautiful lot just shy of an acre in Shady Side, the home offers four bedrooms and an easy, comfortable floor plan filled with natural light, beautiful windows, gorgeous flooring, and thoughtful finishes throughout. At the heart of the home is a stunning gourmet kitchen featuring beautiful cabinetry, warm butcher-block countertops, stainless steel appliances, a stylish backsplash, generous workspace, and a fresh coastal aesthetic that makes the entire space feel inviting. The primary suite is a wonderful retreat with an enormous walk-in closet and a sleek, spa-inspired bath featuring a beautiful walk-in shower with glass doors. Additional bathrooms carry the same clean, sophisticated design, while the incredible laundry room proves that even the most practical spaces can be beautiful. Step outside onto the spacious deck and imagine summer dinners, weekend cookouts, morning coffee, or a glass of wine as the sky changes color at sunset. The huge yard offers nearly an acre to spread out, garden, play, entertain, or simply enjoy having space around you. And then there is the garage. More than 1,500 square feet of detached garage and workspace with THREE bays and electric creates an absolute dream setup for car enthusiasts, collectors, hobbyists, contractors, or anyone who wants room for vehicles, tools, storage, and projects without sacrificing the house or yard. The home and garage roofs date to 2023, along with the home's siding. Beyond the property, Shady Side delivers the Chesapeake lifestyle people fall in love with: water views, beautiful sunsets, neighbors walking their dogs, kids playing, and the relaxed sense of community that makes evenings feel a little slower and weekends feel a little longer. Here, you can enjoy the character of a coastal community while coming home to a beautifully renovated property where the transformation has already been completed. Beautiful inside, extraordinary outside, and filled with unexpected features, 1221 Bast Lane isn't simply move-in ready—it's the kind of place that makes you excited to come home.

1221 Bast Ln, Shady Side

Listing courtesy of Coldwell Banker Realty. Contact:

$299,900

4 Beds ⋅ 2 Baths

Welcome to this charming 4-bedroom, 2-bath home in the desirable Snug Harbor community of Shady Side. Offering approximately 1,930 square feet of living space, this property features a spacious layout, detached garage, and generous yard with plenty of room to enjoy outdoor living. Conveniently located near marinas, parks, local dining, and Chesapeake Bay recreation, this home presents a wonderful opportunity to enjoy the relaxed waterfront lifestyle with easy access to Annapolis. This property has an exclusive boat slip!

1704 Maryland Ave, Shady Side

Listing courtesy of Sell Your Home Services. Contact:

$998,000

4 Beds ⋅ 3 Baths

Waterfront living at its finest! This custom-built Chesapeake Bay home offers breathtaking panoramic views stretching all the way to the Bay Bridge. Meticulously maintained and truly move-in ready, this exceptional property combines luxury, comfort, and the best of coastal living. The main level features beautiful hardwood floors, a spacious gourmet kitchen with granite countertops, stainless steel appliances, and an open layout overlooking the inviting family room with a gas fireplace and spectacular Bay views. A main-level bedroom and full bath provide the perfect accommodations for guests. Upstairs, you'll find three additional bedrooms and two full baths, including a stunning waterfront primary suite. Wake up each morning to endless water views through walls of glass, then step onto your private covered terrace to enjoy your morning coffee while watching the sunrise over the Chesapeake Bay. Outside, your private pier offers the perfect place to fish, crab, or take the boat for a day on the water. Cruise to the many nearby waterfront restaurants and marinas, or simply relax and enjoy the peaceful waterfront setting. Conveniently located with an easy commute to Annapolis, Washington, D.C., and Baltimore, this remarkable home is nestled in the charming waterfront community of Felicity Cove. If you've been dreaming of exceptional Chesapeake Bay waterfront living, this is a home you won't want to miss.

4721 Oak Rd, Shady Side

Listing courtesy of Schwartz Realty, Inc.. Contact:

$625,000

4 Beds ⋅ 3 Baths

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 spectacular bay views. This level also includes the primary kitchen, a bright sunroom, and deck—perfect for relaxing or entertaining while enjoying the waterfront scenery. The upper level offers a serene primary suite with stunning Chesapeake Bay views, a private bath featuring a Jacuzzi tub, and an additional guest bedroom. Experience the feeling of year-round vacation living with community amenities that include a pier and boat ramp, providing easy access to the bay.

4734 Oak Rd, Shady Side

Listing courtesy of Schwartz Realty, Inc.. Contact:

$599,900

4 Beds ⋅ 3 Baths

**Open House this Saturday September 12th 10am-12pm!** 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 water softener / well pump (relocated to garage), and 66-gallon water heater. 2025 - replaced roof, replaced HVAC, Primary bathroom renovation (cabinet, vanity, shower, upgraded flooring, replaced toilet, fogless mirror), and replaced dryer vent. Don't miss the opportunity to purchase this stunning home sitting on a 1-acre natured filled lot. Please schedule all showings via Showing Time.

1582 Snug Harbor Rd, Shady Side

Listing courtesy of Maryland Waterfront Properties LLC. Contact:

$399,900

4 Beds ⋅ 2 Baths

Coastal Comfort, Steps to the Beach - Tucked in the water privileged community of Cedarhurst on the Bay and just a short stroll to the beach and neighborhood amenities, this charming cottage offers relaxed coastal living with a layout full of character. The home features three bedrooms, two with beautiful coffered ceilings that add height and architectural interest. The full bath includes a tub and shower combination. The bright kitchen shines with white cabinetry and brand new, never used stainless steel appliances, giving it a clean, fresh feel. The living room opens to the fenced backyard and patio through a sliding glass door, inviting easy indoor and outdoor living. Just one step down from the living room is a private office with double doors, its own half bath, and access to the laundry and utility room, offering flexible space for working from home, hobbies, or guests. Outside, the circular driveway provides generous parking, and the backyard shed adds convenient storage for beach chairs, bikes, and lawn equipment. BOAT SLIPS AVAILABLE

1199 Oak Ave, Shady Side

Listing courtesy of Long & Foster Real Estate, Inc.. Contact:

$669,500

4 Beds ⋅ 2 Baths

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 accommodate 40ft+ boats. Total income for 2025 was $6900. with only a few slips rented. Will require a commercial lender or cash to purchase.

1462 Snug Harbor Rd, Shady Side

Listing courtesy of Schwartz Realty, Inc.. Contact:

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