Shady Side MD Real Estate & Homes for Sale

Enjoy water views of the community harbor with 60 boat slips and direct access to the Chesapeake Bay - a dream setting for boating and coastal living. This beautifully crafted home features classic board-and-batten siding and a welcoming front porch that creates timeless curb appeal. Inside, the open-concept layout seamlessly connects the dining area and family room, making it perfect for everyday living and entertaining. The spacious kitchen is the heart of the home, showcasing an oversized quartz island, stainless steel appliances, and abundant cabinetry for both casual meals and gatherings. A main-level home office or flexible choice room offers the ideal space for working from home or relaxing. Upstairs, the owner's suite features a large picture window, expansive walk-in closet, and a spa-inspired bath with a luxury shower. Just a short walk to the community center and playground, residents also enjoy Cedarhurst's rare four acres of community-owned waterfront property with panoramic bay views, open lawns, wetlands, picnic areas, playgrounds, ball fields, and opportunities to watch sunrises, sailboats, waterfowl, and local watermen working the bay.

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.

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 ALL OFFERS DUE BY MONDAY JULY 20, 2026 4PM

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.

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 cabinet space, and a bright dining area. The kitchen opens seamlessly to the spacious living room, highlighted by a cozy gas fireplace and engineered hardwood flooring throughout the main level. Step outside through the kitchen slider to a wonderful screened porch, the perfect spot to relax and enjoy the outdoors. An adjoining rear deck overlooks the fully fenced backyard, providing plenty of space for entertaining, pets, or play. Upstairs, you'll find two additional bedrooms connected by a convenient Jack-and-Jill bathroom. Ideally located for an easy commute to both Washington, D.C., and the Annapolis area, this home also qualifies for 100% financing through the USDA Rural Development loan program, making homeownership even more attainable. 24hr. showing notice is required.

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 a long-term tenant who would love to remain, it includes a living room, bedroom, kitchenette, and full bath. The upper level of the home is accessible from both the interior of the main house and a separate exterior entrance. This space offers a living room, kitchenette, and two additional bedrooms, providing even more flexibility for extended family or potential rental use. Situated on a generous -acre lot, this property offers endless possibilities for the right buyer. The home requires updating and is being sold "As Is". Conventional financing or cash buyers only.

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 enjoy water-oriented amenities and a relaxed lifestyle, all while being conveniently located with easy access to Annapolis, Washington, D.C., and major commuter routes. The perfect blend of waterfront living and everyday convenience.

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 court, and picnic areas. Conveniently located near local marinas, waterfront dining, parks, and Chesapeake Bay attractions, with easy access to Annapolis, Edgewater, Washington, D.C., and Baltimore. A great opportunity to enjoy a water oriented lifestyle in one of Southern Anne Arundel County's popular waterfront communities.

*** 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 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!

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.

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 functionality. The updated open-concept kitchen serves as the heart of the home, seamlessly connecting to the dining and living areas - perfect for everyday living and entertaining. Step outside onto the expansive deck, where you'll find a hot tub ready for relaxation after a long day. The spacious backyard provides plenty of room for outdoor dining, family gatherings, and summer fun. Additional features include a detached garage, storage shed, and ample yard space to enjoy. Just one block from the community waterfront, pier, and playground, you'll appreciate the convenience of nearby recreation and stunning Chesapeake Bay views. Residents of Cedarhurst enjoy access to exceptional community amenities, including a marina, fishing pier, clubhouse, and playground. With summer here and the Chesapeake Bay just steps away, this is a rare opportunity to embrace the waterfront lifestyle you've been dreaming of. Don't miss your chance to make this exceptional home your own!

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 d cor. A new roof provides peace of mind for years to come. Outside, enjoy a semi-private, 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.

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 relaxing outdoors. Inside, the updated kitchen features granite countertops and stainless steel appliances, while gorgeous hardwood floors with custom inlay accents add warmth and character throughout the home. The spacious primary suite boasts vaulted ceilings and a private en-suite bath, creating a comfortable retreat. All bedrooms are generously sized and offer ample closet space. Enjoy peaceful mornings with a cup of coffee or unwind in the evenings on the charming enclosed front porch, perfect for reading or taking in the neighborhood atmosphere. Residents of Avalon Shores enjoy exceptional community amenities, including two playgrounds, baseball fields, a community boat launch, and water access. Opportunities like this are rare in such a desirable waterfront community. Don't miss your chance to make this wonderful home your own!

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, stainless steel appliances, a center island with seating, and a sleek range hood. Large bay windows flood the main level with natural light. Enjoy beautifully finished bathrooms, a bedroom on the main living level, and two spacious bedrooms upstairs. Want more room? There's extra space for an office, playroom, or a bedroom in the loft. Step outside to discover 63 feet of premier waterfront along South Creek. The spacious backyard and private dock with electric & water offer the perfect launchpad for kayaking, paddleboarding, or simply soaking in the tranquil scenery. The primary bedroom has a private balcony to enjoy the creek views. Enjoy peace of mind with new kitchen appliances (dishwasher, fridge - 2025; range hood - 2026), new roof (2025), new HVAC (2026), and sealing work and crawl space encapsulation (2020). Complete with an attached two-car garage offering secure inside access, and the convenience of a personal air-conditioned gym (or open the doors and enjoy the view and sounds of nature!). This turnkey property is a rare opportunity to live the ultimate waterfront lifestyle. Schedule your tour today!

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.

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 open-concept main level featuring gleaming hardwood floors and sun-drenched windows that allow sweeping, panoramic water views. The gourmet kitchen is an entertainer's dream, equipped with premium granite countertops, crisp cabinetry, and stainless steel appliances. Upstairs, the private primary suite serves as a peaceful sanctuary, complete with its own private terrace - the perfect vantage point for watching the sunrise over the Bay with your morning coffee. Outside, your private oasis awaits. The property features a private pier, perfect for crabbing and fishing for Rockfish. Equipped with high-efficiency gas heat, this property offers the ultimate lock-and-leave or year-round coastal lifestyle. Don't miss this rare opportunity to own a modern waterfront gem just minutes from local parks and trails, and an easy commute to Annapolis, DC, and Baltimore.

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 rare find, and the price makes it even more compelling. Whitehall backs every home with a fixed-price contract, weekly progress reports, and a 5-year structural warranty, the kind of transparency that makes the building process smooth and confidence-inspiring. Construction-to-permanent or cash financing required; 100% VA financing options available for those who qualify. Whitehall Building & Company's Chessie plan is a thoughtfully designed three-level home offering over 3,000 square feet that lives larger than it looks. The main level centers around a generous family room with fireplace, a well-proportioned kitchen with pantry, dining area, and a dedicated office, the kind of layout that feels spacious and connected. A covered porch off the main level brings the peaceful, wooded setting into the daily experience. Upstairs, the primary suite is a true retreat, complete with a private bath and walk-in closet. Two additional bedrooms, a shared full bath, and upper level laundry round out the second floor. The lower level includes a bedroom and full bath, ideal for guests or added flexibility, along with a two-car garage and entry foyer.

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 room off the kitchen with no closed-off spaces - ideal for entertaining. Deltec home, designed with durability and efficiency in mind. Deltec homes are known for their strength, energy efficiency, and resistance to high winds and severe weather. Large windows surround the home, filling the interior with natural light and enhancing the panoramic water views. Wood floors flow throughout, adding warmth and character. Step outside to the wraparound deck, perfect for relaxing and taking in the dreamy scenery. Additional quality exterior upgrades include durable Hardi-plank siding and architectural roof shingles, both known for their superior longevity, performance, and curb appeal. Situated on a peninsula tucked between the Chesapeake Bay and 500 acres of state park, this property is currently enjoyed as a charming second-home retreat and part-time Airbnb. Come experience this one-of-a-kind home and incredible setting! Gated community offers a boat ramp, 2 private piers for fishing, crabbing, and boating, and a walking trail along the Bay.

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 hardwood floors throughout and a spacious layout designed for both comfortable living and entertaining. The oversized 21' x 23' primary suite offers a true retreat with plenty of room to unwind, while the additional bedrooms are generously sized as well. The main level features a versatile gym/office space that could easily serve as a fourth bedroom, guest room, or playroom depending on your needs. The heart of the home is the large eat-in kitchen with ample space for gathering, complemented by a separate formal dining room and an expansive family room featuring a cozy wood-burning fireplace. Major updates include a new roof installed in 2020, offering peace of mind for years to come. Conveniently located in a USDA-approved area, this home also qualifies for 100% financing eligibility for qualified buyers. If you've been searching for spacious living paired with a sought-after water lifestyle, this Cedarhurst gem checks all the boxes.

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 island with breakfast bar area! The open flow from the kitchen to dining area and then into the living area with corner gas fireplace in view, is a dream! The upper level features large bedrooms and the owners suite features a walk-in closet with built-ins and luxurious bath with double vanity and glass-enclosed tile shower! The additional bedrooms are designed to allow the Sunlight in with the central bath having a dual vanity as well. Come enjoy all the amenities this neighborhood has to offer, like the community Beach, playground areas, dock and boat ramp for accessing South Creek and the Rivers and Bay! You will know you are home when you arrive, come take a look!

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 upgraded appliances, modern cabinetry, and beautiful hardwood floors, creating a bright and inviting space for cooking, gathering, and unwinding. Step out onto the large deck for effortless entertaining, with plenty of parking for guests. Two sheds! Vinyl fenced in flat back yard! Wake up to sunrise views from the upper level decks or take a short stroll to the community dock for a peaceful moment by the water. This water privileged neighborhood is perfect for year round living or a budget friendly bayside retreat. Launch your kayak or boat for days on the Bay, explore nearby marinas and yacht clubs, or enjoy local waterfront restaurants, dock bars, and scenic parks. Conveniences along Shady Side Road and Snug Harbor Road keep daily life simple, and commuting to D.C., Andrews AFB, or Annapolis is a breeze. This home conveys as a Marina Association Slip Holder Member, giving you full access to the revitalized marina and boat ramp.

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!

This is a luxury home in Shady Side- turn key in every way for long term low maintenance living. This is not a cosmetic renovation. This home has been comprehensively rebuilt from the inside out, offering the rare combination of modern luxury finishes and complete system-level replacement in an established gated, water-privileged community in Shady Side. Every major component has been replaced, including all new plumbing, HVAC system, crawl space insulation, crawl space encapsulation, water heater, and windows - delivering the comfort, efficiency, and peace of mind typically found in new construction, without the wait or cost of building and without the builder grade finishes. The thoughtfully redesigned layout features 3 bedrooms and 2.5 fully updated bathrooms, with an emphasis on open, functional living and low-maintenance ownership. At the center of the home is a fully reimagined kitchen featuring quartz countertops, custom shaker cabinetry, and brand-new premium appliances. Clean, modern finishes throughout create a cohesive design that feels elevated and timeless. A bright four-season room extends the living space year-round and offers flexible use for dining, lounging, or entertaining, complete with its own mini-split system for comfort in every season. Upstairs, the primary suite provides a private retreat with direct access to a secluded deck - an uncommon feature that creates a true indoor-outdoor escape for morning coffee or evening relaxation. Located just minutes from marinas, waterfront dining, and commuter routes, this home delivers coastal living in a quiet, established community setting. Unlike typical renovations in this price range, this property has undergone a full system replacement and complete interior rebuild, making it one of the few truly turn-key homes available in a gated, water-access community under $500,000. Move in and enjoy a fully finished home where everything is new, everything is complete, and no additional work or capital expenses are required.

Non-riparian waterfront home offering sweeping, unobstructed views of the Chesapeake Bay. Wake each morning to breathtaking sunrises over the water, best enjoyed from your expansive deck with a cup of coffee in hand - an experience that never gets old. Inside, the home is filled with natural light and features an open-concept layout designed to maximize those stunning bay views. The main level boasts hardwood floors throughout, along with two comfortable bedrooms and a full bath. Upstairs, a versatile loft space with a half bath is ideal for a home office, guest accommodations, or a quiet retreat. Located just steps from the community pier, boat ramp, and additional amenities, this property offers the perfect blend of relaxation and coastal living. Home is not in flood zone.

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 reflects your style. 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 quartz 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. $5,000 closing assistance with preferred lender & Title company. Actual features, finishes, and layouts may vary.