Browse All Shady Side MD Between $300K - $400K Properties for Sale

Welcome to 4733 Washington Avenue, a beautifully updated 3-bedroom, 2-bath single-level home tucked away on a private, fenced corner lot in the water-oriented community of Idlewilde! Freshly painted throughout and filled with thoughtful updates, this home is truly move-in ready. The newly renovated primary bath features heated tile floors, a beautifully tiled shower surround, new vanity and updated lighting. Both bathrooms have been refreshed with new vanities and custom lighting. New recessed lighting throughout the main living areas gives the home a bright, updated feel, while beautiful hardwood floors and plantation shutters add warmth and character. The spacious kitchen features granite countertops and plenty of room for gathering. Outside, enjoy the freshly stained deck overlooking the approximately .22-acre fenced yard—perfect for entertaining, pets, gardening or simply relaxing among the mature trees. Additional improvements include a newer roof and newer front porch/deck, plus two storage sheds for all your outdoor essentials. And don’t forget the lifestyle! Idlewilde offers a community pier, playground and kayak launch on the Chesapeake Bay, with walking paths nearby and multiple county parks to enjoy. Launch your kayak, spend the day on the water, or simply enjoy everything this charming Chesapeake Bay community has to offer. This is a move in Ready and full of charm home with convenient one-level living and a wonderful water-oriented setting—4733 Washington Avenue is ready to welcome you home!

4733 Washington Ave, Shady Side

Listing courtesy of RE/MAX Leading Edge. Contact:

$370,000

2 Beds ⋅ 2 Baths

Welcome to this charming 2-bedroom, 2-bath rambler in the desirable water community of Westelee. This well-maintained home offers comfortable one-level living with an inviting kitchen, spacious living areas, and a large yard ideal for outdoor entertaining, gardening, or relaxing. Cellar area has lots of room for storage or a work area with insulated walls. Recent updates include a new roof, electrical breaker panel, HVAC system, and hot water heater, well pump and appliances all completed in 2023. Both bathrooms have been updated for modern comfort and style. The voluntary community association provides access to a private beach, boat ramp, playground, pavilion, and pier. A wonderful opportunity for those seeking a move-in-ready home with plenty of outdoor space in a water-oriented community.

4911 Magnolia St, Shady Side

Listing courtesy of RE/MAX United Real Estate. Contact:

$364,000

2 Beds ⋅ 2 Baths

Welcome to 1500 Garst Road in the water oriented Columbia Beach community of Shady Side. Enjoy private community access to Herring Bay and the Chesapeake Bay lifestyle, with a sandy beach, fishing pier, boat ramp, and playground just moments away. This 2-bedroom, 1.5-bath home offers a unique layout with both bedrooms and a full bath on the main level, and an upstairs living area and kitchen plus a convenient half bath. Cozy up by the wood-burning fireplace or step outside to a spacious yard with a nice vinyl privacy fence, plus a deck for relaxing or entertaining. The waterproof crawl space is a valuable improvement for peace of mind. Come experience the Bay lifestyle without the waterfront maintenance.

1500 Garst Rd, Shady Side

Listing courtesy of HomeSmart. Contact: 3013524065

$349,900

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: 8882193009

$380,000

3 Beds ⋅ 3 Baths

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 surrounding landscape while taking advantage of the area's relaxed coastal lifestyle. Whether you're looking for a primary residence, a weekend retreat, or an investment opportunity, this property provides a wonderful chance to create your vision in a desirable Anne Arundel County location. Don't miss the opportunity to explore the possibilities this home has to offer.

6372 Shady Side Rd W, Shady Side

Listing courtesy of Maryland Realty Connection. Contact: admin@mdreoconnection.com

$349,900

3 Beds ⋅ 1 Baths

*** OPEN HOUSE - 2-4:00PM, SUNDAY, SEPT 13, 2026! *** 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, fully fenced backyard—a private, serene oasis overlooking lush greenery. Upstairs, a versatile bonus loft with bright skylights functions flawlessly as a third bedroom, home office, or reading nook. A convenient detached storage shed stands ready for your tools and water toys. Just a short walk away, you can take a refreshing dip, paddle a boat, enjoy the popular community playgrounds, or simply take in the panoramic water views at the serene community marina. Enjoy ultimate peace of mind with major updates already completed, including a newer roof (2020), a newer HVAC system (2021), and a recently cleared sewer line. Best of all, this home has been a successful, active Airbnb, and the seller is conveying all furnishings. Schedule your private tour today!

4921 Olive St, Shady Side

Listing courtesy of Redfin Corp. Contact: 3016586186

$325,000

3 Beds ⋅ 1 Baths

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 the extra expense of association fees! Inside, you'll find an updated kitchen featuring stainless steel appliances, granite countertops, ceramic tile flooring, and a stylish backsplash. The bathroom has been renovated with an updated vanity, toilet, and jetted tub. Modern wood flooring in the living room adds warmth that complements any décor. A new roof provides peace of mind for years to come. Outside, enjoy a semi-private, ¾ fenced in yard, a spacious storage shed, and off-street parking for up to four vehicles. Community amenities include a boat ramp, marina with boat slips, fishing pier, playground, gazebo, and a beautiful waterfront community center available for private events. Conveniently located within commuting distance of Washington, DC, Annapolis, Chesapeake Beach, and NAS Patuxent River.

1172 Cedar Ave, Shady Side

Listing courtesy of Weichert, REALTORS. Contact: afitzgerald@weichertrealtors.net

$349,900

3 Beds ⋅ 2 Baths

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.

4738 Washington Ave, Shady Side

Listing courtesy of Lazar Real Estate. Contact: (443) 562-8498

$394,700

3 Beds ⋅ 3 Baths

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 kitchen, boasting sleek white cabinetry, premium quartz countertops, and matte black fixtures, all set against striking herringbone plank flooring. The spacious living area features hardwood flooring and French doors that open to your back deck—perfect for indoor-outdoor entertaining. Bathed in natural light, the home leads you upstairs to a serene primary suite and two additional bedrooms. This turn-key gem is the retreat you’ve been waiting for. Schedule your tour today and start living the Bay life!

1527 Lincoln Rd, Shady Side

Listing courtesy of Home Towne Real Estate. Contact: 8882252736

$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:

$304,000

3 Beds ⋅ 3 Baths

Welcome to this 2-story home nestled in the serene Avalon Shores community. This home features 3 bedrooms, 2 full baths, and 1 half bath. Eat in kitchen with additional room for table space. The exterior boasts multi-level decks ideal for outdoor entertaining, a shady yard offering privacy, and spacious 2 car garage. Located in the peaceful Avalon Shores subdivision, this home is close to Anne Arundel County Public Schools and offers easy access to local amenities and recreational activities. Additionally, you’ll find shopping centers, restaurants, and parks just a short drive away. Check out the virtual tour !

4908 Aspen St, Shady Side

Listing courtesy of Maryland Realty Connection. Contact: admin@mdreoconnection.com

Start Your Search

Between $300K - $400K Shady Side Real Estate

Our website features the best real estate search for between $300k - $400k properties available in Shady Side and surrounding areas. It is the only site you will ever need! It is easy-to-use and updated by the official Realtor®’s database every 15 minutes.

You can save searches, and get daily email alerts of new listings, price changes, sold data, and market reports. Our Interactive Map Search allows you to view properties on a map or refine your search by drawing the boundaries around the area you desire.

Curious about what’s happening in your neighborhood? You can create a custom market report to see what’s active, under contract, and sold in your neighborhood!

Considering selling or refinancing your home? Get an INSTANT property valuation now!