Shady Side MD Real Estate & Homes for Sale

Welcome to Shady Side on the Western bank of The Chesapeake Bay. Much more affordable than Annapolis to the north and way more relaxed and chill. All the benefits of The Chesapeake Bay and still convenient to The District, Baltimore and The Eastern Shore. Weve just completed a thorough rehab of this wonderful rancher that sets far back off of the street and offers a 2 car detached garage, rear deck, 2 car attached garage and an inground swimming pool that is all ready for the summer fun and backyard parties. Mature trees dot the land and provide plenty of shade and theres a fully fenced rear yard with a storage shed and tons of privacy. Theres a multicar driveway for all of your friends and family and plenty of room inside for sleepovers. A bright and sunny kitchen with center Island, plenty of kitchen cabinetry and a sliding door to the private rear deck. Three large bedrooms, a master bath, spacious living room and an eat in kitchen. If youre looking to party, this is the place. Schedule an appointment today and notice that wonderful curb appeal as you approach. Catch this one just in time for your Fourth of July party!

Charming 3-Bedroom Home in Quaint Shady Side, MD Welcome to this lovely 3-bedroom, 2 full-bath home nestled in the heart of Shady Side! Perfectly blending comfort, convenience, and outdoor charm, this well-maintained property is a rare find. Step outside to your huge fenced-in backyard, ideal for gatherings, play, or peaceful relaxation. Enjoy evenings around the cozy fire pit, or take advantage of the raised garden beds, ready for your seasonal planting. The home backs to serene woods, offering privacy and a natural backdrop year-round. Inside, youll find a thoughtfully designed layout with three spacious bedrooms and two full bathrooms, providing ample space for families, professionals, or anyone seeking a peaceful retreat with easy access to urban centers. Located just a short drive to Washington, D.C., Annapolis, and major commuting routes, this home offers the perfect balance of small-town charm and big-city access. Shady Side is known for its welcoming community, waterfront restaurants, nearby library, grocery stores, and more - all just minutes away. Families will also appreciate the area's highly rated school system, making this an ideal place to put down roots. Dont miss the opportunity to live in one of Anne Arundel Countys best-kept secrets - schedule your showing today!

Welcome to 1440 Cedarhurst Road! This beautifully maintained home offers over 2,400 square feet of comfortable living space, featuring 4 bedrooms and 2 bathrooms on a spacious, flat lot. Step inside to discover gleaming hardwood and tile flooring throughout. The heart of the home is a spacious kitchen with a center island, seamlessly connected to an open dining area. Just off the kitchen, enjoy a stunning sunroom with a vaulted hardwood ceiling and its own dedicated HVAC system. Down the hall, you'll find a massive family room complete with a built-in fireplace, ideal for relaxing or hosting guests. The private master suite is thoughtfully separated from the other bedrooms, featuring a generously sized walk-in closet and ample room to unwind. Brand new carpet in the family room and master suite. Outside, follow the walkway to a detached garage and a separate workshop-perfect for hobbies, storage, or extra workspace. Dont miss your chance to make this spacious and charming property your new home!

Recent Price reduction! Chesapeake Bay views and close to the community dock and harbor! Feels like you are on vacation all year round! This home has 4 bedrooms 2.5 baths and a 3rd floor bonus room with balcony and Chesapeake Bay views! It can be used as a family room or a 5th bedroom! Owners suite also has a balcony with Bay views! Home has many new windows and the roof was replaced with Architectural shingles in 2018. It has an oversized 1 car garage with workshop for storage for those handyman/handywomen projects. Sale contingent on owner finding a home of their choice and they may need a rent back to make that work. New photos will be coming!

Calling all investors, second-home seekers, and visionaries-this is the project youve been waiting for! 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**

HONEY STOP THE CAR!!! It's better at the Beach! Incredible peninsula location with 180 degree views of the Chesapeake Bay in the gated community of Columbia Beach in Shady Side , Maryland. This 2 level 3B/1.5 BA home with an inverted floor plan is the perfect weekend retreat or full time main residence. Vacation every day! You can see the Chesapeake Bay Bridge on clear days right from your upper level deck .This beautiful property has 2 front decks and 2 rear decks and a fenced in backyard. It also has 2 vacant lots behind the home which are attached to the sale. Short walks to fishing/crabbing piers, Boat ramp and playground areas. The house is fondly known as 'The Pizza Hut House" because of the roof shape and style. It has an open upper level floor plan and it's just perfect for entertaining , or for quiet time with the family and of course pizza! There's a basketball/tennis court , a beach within a short walking distance and a community walking path. No HOA and Only 35 miles to DC, 40 miles to Baltimore and 20 miles to Annapolis making for an easy commute. So pack up the car and head to the bay! Bring your kayak, bike, beach bags, jet skis, fishing poles, binoculars and your Honey because life is better at the beach! By appointment only please.

Welcome to 1617 Winters Ave - Coastal Charm with Modern Updates in Idlewild on the Bay Beautifully updated and move-in ready, this 3-bedroom, 2-bath gem is nestled in the water-access community of Idlewild on the Bay. Situated just one block from the Chesapeake Bay, this home boasts fresh interior updates, a fully fenced yard, and two spacious decks ideal for entertaining or relaxing by the water. Step inside to find a light-filled living space with vaulted ceilings, gleaming hardwood floors, and a cozy wood-burning fireplace. The open-concept kitchen has been refreshed with white cabinetry, updated hardware, a stylish butcher block island, and walkout access to the upper deck. Highlights Include: Upgraded kitchen with modern butcher block island and white cabinetry Vaulted ceilings and large windows for abundant natural light Two full bathrooms with updated vanities, including a soaking jacuzzi tub Upper and lower decks perfect for grilling, entertaining, or unwinding under the trees Spacious primary bedroom with walkout access to the yard Energy-efficient washer/dryer (2023) in a convenient laundry closet Fully fenced yard with a charming patio and garden area Idlewild amenities: beach access, pier, playground, clubhouse, and boat ramp access Enjoy the peaceful, coastal lifestyle with the convenience of being just a short drive from Annapolis and less than an hour to D.C. or Baltimore. This home combines the best of comfort, style, and Chesapeake Bay living. ð?? 1617 Winters Ave - Your updated escape by the Bay is waiting. Schedule your private showing today!

Move-In Ready Coastal Gem in Shady Side - No HOA, Big Yard, and Modern Upgrades! Tucked away in a peaceful, water-oriented community just minutes from the Chesapeake Bay, this 3-bedroom, 2.5-bathroom home offers the perfect blend of charm and convenience. Enjoy recent updates including a new HVAC system, water heater, well pump & softener, electrical upgrades, and fresh paint - plus stylish new flooring on the main level. The home features a bright, open layout, a fenced-in backyard perfect for cookouts, and an oversized driveway that fits 3-4 vehicles easily - boat included (2 minute drive to the public docking point)! With no HOA, low-maintenance living, and quick access to marinas, dining, and outdoor recreation, this is your chance to own a move-in ready home by the water without breaking the bank. â?¡ Bonus: Speed-tour video available! Dont wait - schedule your private tour today. https://youtu.be/67y5ti6b0rk?si=su69fqlz29IQazKl ð?? Shady Side, MD - Close to Deale, Annapolis, and more.

Imagine: welcoming friends and guests as they approach your home by powerboat, sailboat, or stand-up paddleboard; greeting osprey as they return to their annual nesting spot to raise their young each spring; watching Wednesday night sailboat racers make their way out of the river; relishing spectacular year-round sunsetsâ?¦And now imagine enjoying this incredible backdrop from the comfort of your living room, bedroom, or dinner table; from your deck, lawn, or private pier. For those looking to embrace the Chesapeake Bay lifestyle, this property is a dream come true. Welcome to 1100 Steamboat Road, offering the best of waterfront living on the beautiful West River in Shady Side, MD. Sited at the end of Steamboat Road on a serene lot, this stunning property features approximately 133 feet of water frontage including expansive, 180-degree views of the West River, plus a 300-foot private dock with two slips (mean low water estimated at 7 feet for the first slip and 3.5 feet for the second). One slip has a motorized 20,000-lb boat lift; the second was previously configured with a lift with components available should a future owner choose to convert it back. Sailors and powerboaters alike will appreciate easy access from the dock to the channel in the river and the Bay beyond. The dock is outfitted with electricity, water, and two floating docks to accommodate dinghies, run-abouts, kayaks, or SUPs. The elegant, custom-built home, completed in 2006 under purview of the current owners, was expertly designed to enhance the setting. Most living spaces in the move-in ready 4-bedroom, 2.5-bath residence enjoy sweeping, unobstructed views. Among the many highlights are a main level with an airy, easy-flow layout great for entertaining, a gourmet eat-in kitchen, a main-level bedroom (currently configured as an office), an attractive elevator for convenient access between floors, a masonry chimney and gas fireplace, and a deck with a gas fire pit - a favorite spot for enjoying â??top tenâ? sunsets. The second level includes a primary suite with two walk-in closets and a spa-like bath with separate WC, a family room with prime views and a private balcony, plus two additional generously-sized bedrooms sharing a hall bath. Two staircases allow for privacy between the primary suite and guest spaces when needed. A stand-alone garage provides covered parking for 3 vehicles plus a substantial upper-level loft space with great potential: consider converting it to a bunk room, teen hangout, separate work studio, or other creative use. The well-tended yard includes an automatic irrigation system for lawn and landscaping, and the home is equipped with a whole-house backup generator. This special property also holds a place in local history: from the late 1800s to early 1900s, the steamboat â??Emma Gilesâ? docked here on a regular route from Baltimore to various points on the Bay (hence the name Steamboat Road). Today, its ready for your enjoyment as a weekend getaway or full-time residence, conveniently located less than 40 miles from downtown DC, approximately 20 miles from Annapolis, and less than 40 miles from BWI Airport. Truly a must-see! Agent related to owners. Square footage estimated per recent floor plan drawing; all measurements approximate.

Unique Waterfront Dream Home Opportunity at Columbia Beach - Build Your Dream Home on the Chesapeake Bay. Don't miss this rare chance to build or own waterfront Dream Home in the serene, gated community of Columbia Beach, offering breathtaking views of the Chesapeake Bay. This exclusive neighborhood is just 30 minutes from the I-495 Beltway and Annapolis, and only 45 minutes to Washington, D.C., and the Woodrow Wilson Bridge in Virginia. Community Highlights: Gated access for privacy and peace of mind. Stunning bayfront scenery. Boat ramp, short pier, and long pier for water access. Family-friendly playgrounds. Sports facilities including tennis, basketball, and pickleball. Pet-friendly with a commitment to preserving the peaceful environment. Columbia Beach is served by Public Sewer and is known for its quiet streets, low traffic, and tight-knit community, making it an ideal setting for a primary residence or vacation getaway. AirBNB is allowed. The community walking path, which follows the rocky shoreline of the cove, is marked by oval signs featuring a swan. "House-to-be-Built" with flexible design options. Ideal for a custom home measuring up to 46' wide x 32' deep each level. Potential for 2 finished levels plus attic, and designed for: 5BED/4BH. Main level bedroom with full bath - wheelchair accessible. 2-car garage. Deck and/or balcony for stunning water views. "Qualified buyers can finance the entire project - including lot and building - with as little as 5% down, thanks to Construction-to-Permanent loans that may allow for 10%, 15%, or even 20% equity from the start." Lot Details: Approx 60'x100' waterfront lot with completed boundary survey (available via listing documents), listed separately should your prefer just the lot which can be financed over 20year with 25% down through a local and competitive lender. An experienced builder is ready to work with you to create a custom dream home, offering competitive pricing and may even absorb a portion of the lot cost. For additional Info on Columbia Beach: Visit the Columbia Beach page to learn more about the community. Lot owner reserves the right to accept or reject any offer. To maximize land use and support the purchasers project goals, a budget of approximately $1.25 million is recommended. Most Construction-to-Permanent loan programs offer limits up to $1.5 million, though exceptions may be available depending on the lender. The final quote will be prepared as a customized package tailored to the purchasers specific preferences. Seller's concession $20,000.

Location, location, location! Just blocks from the sparkling Chesapeake Bay, this Shady Side gem is cute as can be and full of charm. This 2-bedroom, 2-bath home is flooded with natural light and features cathedral & vaulted ceilings, exposed beams, two brick fireplaces, and luxury vinyl plank flooring throughout. The kitchen opens up to a spacious, versatile room that can serve as a dining room or great room for entertaining, with a brick fireplace, cathedral ceiling, exposed beams, and large windows. You'll love this charming space! The living room also has a brick fireplace, lots of windows, LVP flooring and sliding glass doors that open to the brick enclosed patio overlooking the lovely fenced yard. The renovated primary suite includes stylish sconces, large vanity w/chrome fixtures, quartz countertops, and an on-trend walk-in glass framed shower. The second bath has new lighting, mirror, fixtures, a tub/shower combo, and also hosts the full-size washer and dryer with shelving, The second bedroom boasts a custom Elfa closet system. Step outside to enjoy a fully fenced yard, a patio area framed by brick, a beautifully landscaped garden, and a large shed for extra storage. All this and a newly paved driveway that can hold up to 4 vehicles! Youll love the laid-back lifestyle of Cedarhurst on the Bay --a vibrant community with a clubhouse, dock, playground, & MORE with easy access to waterfront marinas, community parks, and beloved local spots like JesseJays Latin Inspired Kitchen, Petie Greens Bar & Grill, and the Driftwood Diner. Plus, you're just a 20-min drive to Annapolis and under an hour to Washington, D.C., making this the perfect blend of coastal retreat and commuter convenience. Dont miss your chance-this home shows beautifully and wont last long!

Discover unparalleled luxury in this stunning Five bedroom, four and half bath waterfront home, offering two hundred and seventy feet of private shoreline and breathtaking views. Designed for refined living and effortless entertaining, this home delivers an exceptional lifestyle both inside and out. The exterior is a private resort, featuring a heated in-ground pool, outdoor grilling area, fire pit, kayake launch and impeccably landscaped grounds. A private pier with a boat lift provides direct access to the water, making this the perfect setting for boating enthusiasts and those seeking tranquility by the shore. Inside, the home is richly appointed with custom finishes and a spacious open-concept design. The gourmet kitchen offers premium appliances, custom cabinetry, and expansive water views that flow into the main living and dining areas. Every detail has been thoughtfully curated for both function and elegance.The bathrooms have been recently remodeled with luxurious, spa-inspired touches. The primary suite is a sanctuary, complete with a serene spa-like bath, walk-in shower, soaking tub, and private access to an outdoor sauna - your personal retreat just steps from the bedroom. Additional highlights include a new roof, upgraded geothermal HVAC system for efficient, year-round comfort, and a three car garage with ample storage space. Whether youre hosting guests, spending weekends on the water, or simply enjoying peaceful moments at home, this extraordinary property offers the perfect blend of sophistication, comfort, and waterfront charm.

Charming and spacious colonial, situated on nearly 2 picturesque acres in Shady Side. Boasting 4 bedrooms and 2.5 bathrooms, this lovely home features a formal dining room, a spacious family room with a fireplace, and large sitting rooms off to the side, a finely appointed kitchen with granite counters and SS appliances, a large addition off the back of the home with vaulted ceilings and wood ceiling accents. The home also features a large 2 car garage, and a spacious yard which includes ample front back and side yards.

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. 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 combine living and dining rooms to the a nice sized kitchen with appliances and main level bedroom. There is a full bath in each level and three more bedrooms in the upper level. The sunroom with wide windows and lots of natural lights have 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 a shed. Home is located in a water-oriented community and is conveniently close to the beach, marina and Shady Side Market.

Water! Water everywhere! This adorable mid-century cottage faces Hopkins Cove , borders Parish Creek and looks out to the Chesapeake Bay Bridge. It is a dream come true for those who love living on the water, and could be your weekend getaway cottage. Not a fan of cottages? Then, go all in and remodel to make it your own! The possibilities are endless..... The property is being sold "as is". Please contact AACO and the Critical Area Division regarding remodeling permit requirements.

Newly priced and ready for summer, here is your chance to own and enjoy a coastal contemporary â??cottageâ? with panoramic views and the soothing sounds of the Chesapeake Bay. This Bay fronting property has an open airy interior, warm and inviting, with two story vaulted ceilings, walls of windows which showcase the Bay view. The ease of main level living, enhanced with wood floors, includes the living, dining, kitchen, 2 bedrooms, a full bathroom, and laundry . Take advantage of the loft, with its natural light, perfect for a home office or studio. Plus a half bathroom and additional storage. Enjoy seamless indoor - outdoor living, expanded with a new low maintenance deck. Perfect for morning coffee and entertaining on the bay. Replaced: Deck in 2024.. Sump Pump and exterior faucet 2024.., Main level bathroom 2020.. Leaf Filter Gutter Guards , 2019,.. Split 2018.. Bedroom windows, 2016.. Roof, 2014 . Upper half bathroom added in 2009. Situated in the gated water privileged community of Columbia Beach. The community offers residents opportunities for boating, fishing, and other recreation: boat launch, short fishing pier, a long pier, waterfront park, childrens play area, regulation size basketball court, and tennis. The community walking path, along the rocks that line the cove, is marked by oval signs featuring a swan. Vacation Year Round !

Post & beam architect design home with passive solar elements and lots of glass facing the water. A beautiful waterfront lot with southern exposure and wonderful view! Very well protected water on West River, stone rip rap. Pier only a few years old. Hop in your boat and be at one of 2 waterfront restaurants or West River Sailing Club in a couple of minutes. You can join Chesapeake Yacht Club at the end of Hine Drive and walk there! The Yacht Club offers slips, a pool, restaurant and other amenities. This is a unique property with 2 separate 2 story living areas, 2 exterior entrances. The two sides are easily united by just opening the living room to the other side.

**Move-in ready home in the private, water-privileged Westelee community of Avalon Shores **Access to beach, boat ramp, boat slips with electric, kayak rack, new waterfront playground and gazebo **Owner Suite on main level with walk in closet and private bath **Open cathedral ceilings in family room with cozy gas Fireplace and 8' double windows for abundant natural light **Hardwood floors throughout main level **Newly rebuilt deck (2025) **Updated kitchen with granite countertops, glass cabinetry, SS appliances, and propane gas stove/cooktop ** Reverse Osmosis under kitchen sink **4th bedroom/Den upstairs does not have window makes great gaming room **Carrier 3-ton HVAC (2016) ** Hot water heater (2023) **Water softener with chlorine injection (2025) **Mud room with Samsung washer/dryer (2024) **3 TV's convey **Large driveway for boat/RV parking and **12x8 shed for gear storage **Oversized 2 car garage! **Large spacious yard backs to open lot. NEW Architectural ROOF to be INSTALLED PRIOR to CLOSING!!

OPEN Bay-front at this STUNNING Custom Coastal with private pier, Located in coveted Columbia Beach, this airy WATERFRONT is a head-turner, boasting an open floor-plan, with the finest of finishes! Direct Chesapeake Bay location, 100' private pier & 3 jet-ski lifts makes this the perfect retreat - or year round treat- With 3 spacious bedrooms, 2.5 beautiful baths, 9' ceilings & hickory flooring- throughout!- Inviting gourmet kitchen with gleaming granite countertops, large island with seating to host grandly, shiny stainless appliances & open to bright dining & living spaces w/ cozy gas fireplace & direct Bay views! Living spaces are extended by BOTH main-level AND upper-level full-length spaces- covered porch for late day cocktails and crabs after a fun day of boating, to coffee on upper deck waking up to the lap of the waves. Anderson windows, dual-zone HVAC, 'Generac' generator conveys! Ample storage, large closets, stand-up full-house length w/ side windows, dry & tall crawlspace, Close to work & play with unbeatable open views, unmatched community amenities include boat ramp, tennis courts, playground, clubhouse, gated entry & fun events! Just minutes outside of Annapolis- and less than an hour to DC, this gorgeous retreat is sure to please! Hurry to claim today!

Price Reduction!! Your Own Private Retreat, get away from the Rat Race and make this a great place for you and your family. 1337 West River Road , located in Shady Side, MD is a secluded waterfront property that sits on 1.5 acres with 592 feet of waterfront on the South Creek. This property has a home with 2 beds and 1 bath that will need remodeling and/or teardown. it's located 1/4 mile off the main road (West River Road ) follow signs to property. use GPS (once on West River Road make a left turn pass the first house on the left and follow gravel road to the end.)

4 beds/ 1 full bath and 1/2 bath with shower.2144 SQ FT. Home and income opportunity goes with this four bedroom home on .57 acres of (C1B) commercial zoned property. Additional .375 acres and .1243 acres of (MA2) marine zoned property, totaling 1.0693 acres, with 135 feet of bulk headed waterfront, 200 foot pier, and 12 boat slips. Water depth from 4 to 8feet, that can accommodate boats in excess of 40 feet. Total income from 7 of the 12 slips in 2021 was $11,300. POTENTIAL $20,000 PLUS RENTAL INCOME IN ADDITION TO DRY STORAGE AVAILABLE. Many upgrades and extras. Information sheet in the document section of the listing or may be emailed to interested parties. Cold box has been removed.