Shady Side MD Real Estate & Homes for Sale

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 two 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 charming 2-bedroom, 2-bath home in the water-oriented community of Avalon Shores. Perfect for those looking to start out, scale down, or a second home! Freshly updated with new flooring, a new roof, and fresh paint- this home is truly move-in ready! Enjoy a fully renovated bathroom, a spacious deck, and a fully fenced backyard - perfect for pets, gatherings, or quiet relaxation.Step outside and experience the lifestyle this neighborhood is known for: walkable access to the water, dog-friendly streets, and water oriented community and nearby playgrounds, that make everyday living feel easy and enjoyable. Just minutes from local restaurants and shops, and only about 20 minutes to Annapolis, this location offers the best of both worlds!

Discover your waterfront retreat with Chesapeake Bay views, community water access, and an ideal location for both everyday living and weekend escapes. The stunning upper-level living area features vaulted ceiling, a classic wood-burning fireplace, and beautiful hardwood flooring that creates a warm and inviting atmosphere. Large, upgraded windows fill the home with natural light while showcasing picturesque Bay views from multiple vantage points. Designed for entertaining and outdoor enjoyment, the property offers multiple spacious decks and a fully fenced backyard, perfect for gatherings, pets, or simply relaxing outdoors. Enjoy the best of coastal living with community amenities just down the street, including a pier, beaches, playgrounds, and direct water access for kayaking, fishing, and enjoying the Chesapeake Bay lifestyle. Recent improvements, including a newer roof and siding, provide added peace of mind, making this home truly move-in ready. Conveniently located approximately one hour from Washington, D.C., and just 50 minutes from Annapolis, this exceptional property offers the perfect balance of waterfront tranquility and commuter convenience.

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.

Adorable and fully renovated rancher situated on a rare double lot in the water-oriented Idlewild community of Shady Side! This cozy yet spacious home has been thoughtfully updated from top to bottom and offers easy one-level living with modern finishes throughout. Open concept living and kitchen area overlooks the expansive rear yard, creating the perfect space for entertaining or everyday living. The updated kitchen flows seamlessly into the main living space and features stylish finishes and abundant natural light. Spacious primary suite includes a beautifully renovated private full bath, while two additional generously sized guest bedrooms share an updated hall bath. Extensive improvements provide peace of mind, including energy efficient windows (2020), all new plumbing (2020), LVP flooring and subflooring replaced throughout (2020), HVAC and water heater (2021), large rear deck (2023), and roof (2024). Two large storage sheds offer plenty of room for tools, hobbies, or outdoor equipment. Enjoy water views from the front yard and all the perks of this charming water-oriented neighborhood, including a community pier and playground. Conveniently located in the Idlewild community with easy access to marinas, dining, and the Chesapeake lifestyle. Additional updates available in disclosures! You won't want to miss this!

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. 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. 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.

4/6/26. Just broke ground. Late summer 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. $10,000 closing assistance with preferred lender & Title company. Actual features, finishes, and layouts may vary.

THIS IS A TO BE BUILT HOME. Act soon while you are able to still personalize this home with interior selections! 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.

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, open feel. Charming cottage-style windows fill the space with natural light, and LVP flooring flows seamlessly through the living room, kitchen, and wide hallway to the bedrooms. The kitchen features oil rubbed bronze fixtures, soft-close cabinets, granite countertops, and a center island with overhang for stools, plus space for a dining table. There is also potential for a deck off the back of the home, perfect for outdoor living. The main level includes two secondary bedrooms and a spacious owner's suite. The secondary bedrooms feature custom molding, decorative wall trims, and stylish paint finishes - one accented with decorative peelable wallpaper - and share a hall bath with granite vanity and shower/tub combo. Enjoy views of the wooded landscape from the owner's suite, complete with two closets and a distinctive en-suite bath featuring dual sinks, granite countertops, a walk-in shower, custom wall trim accents, and removable wall covering. The lower level provides a versatile living space, including a spacious recreation room with sliding glass doors to the backyard, a flexible 4th bedroom ideal for guests or an in-home office, and an additional full bath with granite vanity and shower/tub combo. Raised garden beds just outside in the backyard and alongside the home are ideal for growing vegetables and flowers.

THIS IS A TO BE BUILT HOME

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

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.

Welcome to this inviting single-family home in the heart of Shady Side! This lovely residence features 3 bedrooms, 2.5 bathrooms, and approximately 2,235 sq ft of versatile living space - thoughtfully laid out to balance comfort and function. Step inside to a warm, open floor plan where natural light enhances every room, and an efficient layout makes everyday living easy. A well-appointed kitchen with stainless appliances and abundant cabinetry flows seamlessly into living areas perfect for both relaxing evenings and entertaining guests. The home also boasts central a cozy fireplace, and an attached garage for convenience. Retreat to the spacious first floor primary suite featuring its own full bath with jetted tub and separate shower. The second floor encompasses two additional bedrooms and and full bath providing flexibility for family, guests, or a home office. Outdoor spaces include a recently built screened in porch with composite decking and a private fenced backyard - ideal for summer barbecues, gardening, or simply enjoying Maryland's beautiful seasons. Situated on a well-sized 7,500+ sq ft lot in a welcoming neighborhood, you're minutes from local schools, Chesapeake Bay waterfront attractions, marinas, dining, and community amenities. Embrace serene suburban living with easy access to Annapolis and the greater Baltimore/Washington region.

Welcome to Cedarhurst on the Bay! Water Provilege Community Within Walking Distance to Community Marina with Slips, Beach, Playground, Boat Ramp along Chesapeake Bay. Gorgeous Colonial with Open Floorplan. Home has Front Porch for your Relaxation, which you have a Wooded Lot Across from it. Large Fenced in Backyard with Deck. Updated Kitchen with Quartz Countertops, Backsplash, Deep Sink with Laminate Floors. Main Level Boasts Wood Plank Floors Throughout. Family Room with Gas Fireplace. Upper Level with Primary Suite, Primary Bath with Soaking Tub, Double Sinks, and Separate Shower. Laundry on Bedroom Level. Home is Hardwired for Generator. Spacious Two Car Garage. Must See to Appreciate!

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.

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 4,600 square feet, the home blends classic Chesapeake architecture with modern scale, light, and livability. High ceilings, oversized doors, and expansive windows draw the water into nearly every room, creating a constant connection to the horizon. The layout balances open, light-filled gathering spaces with a thoughtful separation of private areas, making it equally suited for everyday living and hosting guests. The main-level primary suite is positioned to capture water views, with a fireplace, spa-like bath, and custom walk-in closet. At the center of the home, the kitchen is designed for both daily use and entertaining, anchored by professional-grade appliances and clean, functional design. Outdoor living is fully realized. A waterside saltwater pool, bluestone terraces, teak decking, and a fully equipped pool house create a seamless extension of the home - designed for both relaxed days and larger gatherings. The lawn stretches to a protected shoreline, reinforcing the home's connection to the water. A private 70-foot pier with lift provides immediate access to the Chesapeake, ideal for day boating and spontaneous time on the water, with nearby marinas accommodating larger vessels. Additional features include mature landscaping, a smart irrigation system, multiple outdoor living areas, a detached three-car garage, and a separate storage structure. Silver Water offers a rare combination of design, setting, and livability - an intentional waterfront home where architecture and landscape come fully into alignment.