Shady Side MD Real Estate & Homes for Sale

Rare Shady Side opportunity on 1.58 acres near the Chesapeake Bay. 1451 Shady Rest Rd offers a partially constructed home where building began pre-Covid. The property is ready for a new owner to bring their vision. It includes a permitted 3-bedroom septic system and an operational well, giving you a strong foundation for your new build. In this highly desirable South County area, buyers are transforming older and unfinished homes into custom retreats. This lot is ideal for anyone searching for a buildable property, a new construction opportunity, or acreage close to the Chesapeake Bay lifestyle. Youre just minutes from boating, fishing, and marina access, plus an easy commute: 15 minutes to Annapolis and about 40 minutes to Washington D.C. or Baltimore. Bring your builder, your plans, and your vision. This is your chance to create the home youve been dreaming of in a location that continues to grow in demand. This short sale is being handled by a professional short sale team. Property is sold strictly as-is. All visitors must schedule an appointment and be accompanied by a licensed agent. No unauthorized entry or walking the property at any time.

Experience refined living in this beautifully maintained 3-bedroom, 2.5-bath Colonial, perfectly nestled on a quiet, tree-lined street. This distinguished residence offers timeless curb appeal with a welcoming front porch, a thoughtfully designed interior, and a nicely appointed kitchen ideal for both daily living and entertaining. The home features a spacious primary suite, generously sized secondary bedrooms, and a nice-sized fenced-in yard that provides privacy and room to relax or play. A private driveway ensures effortless parking. Situated just moments from the water-without the upkeep of waterfront ownership- access to a Felicity Cove boat launch, kayak launch, fishing/swimming pier, and located in a well-regarded school district, this property delivers an exceptional blend of comfort, style, and convenience. A rare opportunity to enjoy serene suburban living in a truly desirable setting.

Westelee Welcome's You Home! This 2.5 year old "Pottery Barn" Colonial home is set perfectly on a corner lot with views of the West River. This home has 4 bedrooms and 2.5 baths. Patio was just put in and a 6 foot privacy fence around the backyard in 2024. GREAT FOR HAVING A CRAB FEAST IN THE SUMMER OR BONFIRES IN THE FALL. THIS YARD IS GREAT FOR ENTERTAINING BRING YOUR FAMILY AND FRIENDS. There is NO HOA . The Westelee Community was named in 2018 as the up and coming places to live in South County. The home is located on a dead end street. THE COMMUNITIES PRIVATE BEACH, BOAT RAMP, PLAYGROUND (NEW 2020),PIER W/ ELECTRIC,10+BOAT SLIPS,GAZEBO (2020) ,SWIMMING AND WATER SPORTS JUST 2 HOMES FROM YOUR FRONT DOOR!Bring your crabbing net for day/night time crabbing at the pier, swimming at the beach , fishing off the pier or kayak over to the local waterfront restaurants across the Creek. All is voluntary for $60.00 a year you can enjoy all of these wonderful amenities Westelee has to offer you and your family.LET THE KIDS ENJOY ALL OF THE COMMUNITY ACTIVITIES THAT ARE PLANNED SUCH AS CARDBOARD BOAT RACES FOR FATHERS DAY OR EVEN A HALLOWEEN PARADE. THESE ARE JUST 2 OF MANY EVENTS THE COMMUNITY HAS THROUGHOUT THE YEAR. Chesapeake Yacht club is about 5 homes away and you can join the yacht club and their amenities as well. Westelee is a very small private community located right off the West River. You can sit out in your backyard and entertain all summer long enjoying the bands music from across the river. Sellers will be interested in renting the home out as well.Don't wait this home will not be on the market long!

Home Sweet Home! Come tour this 2 level, 3 bedroom, 2 full bath just a couple blocks to the water. Situated in Columbia Beach, feel like you're vacationing year round! Whether your taking a walk in the gated community, or entertaining in the spacious home, you'll enjoy living here! No HOA. Please read agent remarks.

Welcome to 4717 Frederick Avenue - a charming and updated cottage just two blocks from the West River in the Idlewilde on the Bay community. This 2-bedroom, 1-bath ranch-style home offers comfortable one-level living with thoughtful improvements throughout. Step inside to a bright, open living area featuring neutral finishes and a cozy fireplace, ideal for everyday relaxation. The renovated kitchen includes stylish cabinetry, modern countertops, stainless steel appliances, and space for casual dining. An additional office/flex room provides versatility for work or hobbies. Both bedrooms offer natural light and easy access to the updated full bath. Main-floor laundry adds everyday convenience. Outside, enjoy updated landscaping, a private driveway, and multiple outdoor spaces perfect for entertaining, gardening, or simply enjoying the coastal surroundings. With vinyl siding, central air, and public sewer, this home offers low-maintenance living in a peaceful setting. Conveniently located near waterfront parks, community marinas, and local dining, this move-in-ready home is an excellent opportunity to enjoy the best of Shady Side living.

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 and pain- 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 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!

A Charming Cedarhurst Cottage Near the Water - This charming 1944 cottage in Cedarhurst on the Bay offers easy coastal living and only a few houses from the Bay and the community amenities. Recent improvements within the last year include a new roof, new windows, a new hot water tank and a new water pressure tank. The kitchen has white cabinetry and there is a small laundry room with a washer and dryer combination machine. Both bedrooms are comfortable in size and the bathroom includes a walk in white shower stall with built in shelves for storage. The fenced backyard features a shed and a pleasant deck. Enjoy community amenities such as a pier and gazebo overlooking the Chesapeake, a small beach area, open green space and a marina with boat slips. A relaxed bayside setting makes this a great full time home or weekend getaway.

For buyers seeking a quicker move-in, the same model is currently under construction less than a mile away and will be completed in approximately 30 days, offering the perfect opportunity to preview the craftsmanship and finishes in person or purchase if a faster timeline is preferred. This to-be-built Modern Farmhouse by local builder Laine Street Homes blends timeless architecture with modern luxury. Spanning over 2,200 square feet, the home features a main-level owners suite and high-end appointments throughout. Step inside to an inviting open-concept main level that includes a spacious family room with gas fireplace, a formal office with cathedral ceiling, a morning room nook, dining area, and a convenient half bath. The gourmet kitchen is a true showpiece, featuring a large center island with breakfast bar, soft-close shaker cabinetry, open apron farmhouse sink, quartz countertops, subway tile backsplash, and a five-piece stainless steel appliance package including a wall oven, cooktop, and range hood. The main-level owners suite offers a walk-in closet and a luxury ensuite bath with dual vanities and an expansive 7x6 spa shower with dual shower heads. Upstairs, youll find two additional bedrooms and a second full bath. Additional highlights include LVP flooring throughout the main level, ceramic tile in all baths and the laundry room, public sewer, 30-year architectural shingles, a 92% efficient Carrier HVAC system, 2x6 framing, R49 ceiling insulation, R21 wall insulation, and an air seal package. Outdoor spaces include a 246 square foot paver patio and a spacious wrap-around front porch. With no HOA or restrictive covenants, this home offers rare flexibility and freedom in a highly desirable Anne Arundel County location, convenient to both Annapolis and Washington, D.C.

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.

Peaceful Living by the Bay - Perfect for Downsizing! Looking to simplify without sacrificing charm or location? This move-in ready 3-bedroom, 1-bath rancher is the ideal retreat for anyone craving a slower pace, less maintenance, and more time to enjoy the good life. Tucked on a quiet corner lot next to a protected nature reserve, this single-level home offers peace, privacy, and natural beauty-with low maintenance. Just a short walk to the bay front, youll love starting your mornings with coastal breezes and winding down with sunset walks to the community pier. Inside, enjoy a warm and inviting open layout, complete with a cozy wood stove and a splash of personality from the bright red front door. Major updates-roof, HVAC, water softener, and well pump-all done within the last 3 years-mean you can move in and relax from day one. The manageable yard has 2 sheds for extra storage and a roomy driveway (with space for a boat or guests), and surrounding greenery make outdoor living simple and serene. Plus, the neighboring nature reserve means no new development next door-ever. If youre ready to downsize to comfort, convenience, and coastal charm, this is the home for you.

For buyers desiring a quicker move-in, this same model is under construction less than a mile away and will be completed in approximately 30 days - a perfect opportunity to preview the craftsmanship and finishes in person. This to-be-built custom Arts & Crafts residence by local builder Laine Street Homes blends timeless design with modern luxury. Set on a premium 1.5-acre homesite, the property offers both privacy and functionality. Step onto the welcoming front porch and into a thoughtfully designed main level featuring a private office, formal dining room, and a spacious family room highlighted by large picture windows and a modern gas fireplace. At the heart of the home, the gourmet kitchen impresses with premium quartz countertops, herringbone tile backsplash, tasteful dove and pistachio cabinetry with dovetail joints and soft-close drawers, a walk-in pantry, farmhouse apron sink, and a large island with breakfast bar. Upstairs, the primary suite overlooks the private backyard and features luxury vinyl plank flooring, a walk-in closet, and a spa-inspired bath with a 7x6 walk-in shower boasting floor-to-ceiling tile. Additional highlights include 7-inch LVP flooring throughout the main level, shake siding with stone column bases, 2x6 construction, a 92% efficient HVAC system, and 30-year architectural shingles. With no HOA or restrictive covenants, this home offers rare flexibility and freedom in a highly desirable Anne Arundel County location, convenient to both Annapolis and Washington, D. C.

NEW PRICE!! Amazing opportunity to own an affordable beautifully remodeled home in the waterfront community. Just a short walk from the Chesapeake Bay, this 4-BR, 2-BA home offers approx. 1,300 sq ft of modern living, including a Brand-New signature designer kitchen with an eat-in island, New trash compactor, New security system, New lighting, New Appliances and High End finishes throughout....it's worth the drive to see! Additional features include New roof, New siding, New floors, New bathrooms, New central air, New water heater, New HVAC, New primary suite, and New windows. The property includes a large backyard with a shed for extra storage or convert it for extra space like a workshop, craft room, or hangout area. The spacious primary suite provides a relaxing retreat, while three additional bedrooms offer flexibility for guests, a home office, home gym or hobbies. Every detail has been thoughtfully updated, making this single level home completely move-in ready. Located just steps from the water, Idlewilde on the Bay offers a true sense of community and just a few miles from Annapolis, Washington DC or Baltimore including military locations like the Naval Academy, Fort Meade, NSA and Fort Andrews. Whether youre searching for a year-round residence or a weekend escape, this property is ready to welcome you home today. Welcome home to Shady Side! ** Please contact the co-listing agent for details **

10/10/25 Update: Home is under roof. Estimated completion is projected for January/February 2026. Introducing the Adams model - a beautifully designed home featuring an open-concept floor plan that blends comfort, style, and functionality. At the center of the home, the gourmet kitchen boasts a large island, stainless steel appliances, a walk-in pantry, and premium finishes-perfect for everyday living and entertaining alike. Additional kitchen upgrades include 42� cabinets offering both elegance and practicality. The kitchen seamlessly connects to the dining area and expansive great room, creating an ideal space for hosting gatherings or relaxing with family. Upstairs, youll find a spacious primary suite with a private en suite bath, along with three additional bedrooms, a full guest bathroom, and a conveniently located laundry room. Community offer beach, playground, pier, boat ramp and more. Disclaimer: Renderings and photos are for illustrative purposes only and may show optional features, upgrades, or configurations not included as standard. Actual features, finishes, and layouts may vary.

Coastal Living in a Gated Waterfront Community a Short Distance from Annapolis and Washington, D.C. Awaits You! Discover the perfect blend of charm and comfort in this 2-bedroom, 1.5-bath Cottage by the Bay, located in the desirable gated waterfront community of Columbia Beach. With stunning bay views, this home offers a peaceful escape just steps from the water. Inside, enjoy an open-concept living space featuring vaulted ceilings, hardwood floors, and a gas stand-alone fireplace that adds warmth and character. The loft area provides flexible space for guests, a home office, or a quiet reading retreat-and includes its own powder room for added convenience. Step outside to a spacious deck where you can relax and listen to the water lap against the bulkhead, or take a short stroll to enjoy the communitys private waterfront access. Whether you're seeking a weekend getaway or a full-time coastal lifestyle, this Cottage by the Bay is a rare opportunity to own in one of the area's most desirable waterfront neighborhoods. Schedule your private tour today and experience the magic of Columbia Beach!

Just two doors from the water and steps from a childrens park and boat ramp, this 3-bedroom, 2-bath rancher offers 1,408 sq. ft. of potential. Renovations are underway with many improvements already complete-kitchen updates started, dishwasher included but not yet installed, and bedrooms ready for new flooring. New flooring will be installed throughout the home prior to closing, offering buyers a fresh and updated space to make their own. Enjoy a cozy fireplace, low-maintenance vinyl siding, attached garage, and a spacious 0.29-acre lot. A perfect opportunity to finish your dream home in a sought-after water-access community!

This spacious and well-maintained home offers the ease of one-level living at it's best. The modern kitchen opens to a cozy family room featuring a gas fireplace and a sliding door that leads to a stunning sunroom and adjacent deck-perfect for relaxing or entertaining. Enjoy formal spaces with both a living room and dining room, along with a generous primary suite complete with a private full bath. Two additional bedrooms and a second full bath provide plenty of space for family or guests. Additional highlights include a two-car garage, a two-car carport, a large storage shed, and a handicap-accessible ramp. Situated on a level, usable one-acre lot, this home combines comfort, functionality, and outdoor space in a peaceful setting.

To be built by Whitehall Building & Co., Annapolis largest luxury waterfront builder. Located in the desirable Columbia Beach neighborhood, this coastal-style home will offer 3,700 sqft of living space and the rare combination of panoramic Chesapeake Bay views with the protection of a cove-front setting. Designed for modern waterfront living, the open-concept layout features soaring 10' ceilings on the main level and walls of glass to showcase the water views. With 4 bedrooms, 3.5 baths, and high-end finishes throughout, this home is both elegant and functional. Enjoy community amenities like a boat launch, pier, tennis and basketball courts, playgrounds, and more. Ideally situated with convenient access to Annapolis, DC, and Baltimore. Still time to customize! Buyers can choose their selections and finishes.

This spacious 5 bedroom, 2 full bath split foyer is located in the highly desirable Community; Cedarhurst on the Bay. This remarkable property showcases the epitome of every day, vacation living with stunning views of The Chesapeake Bay. You will quickly be captivated by the grandeur that awaits you. The open layout seamlessly connects the living, dining and kitchen area, creating an ideal environment for entertaining family and friends. The kitchen is a chef's delight including ample storage space. The primary and additional bedrooms offer comfort and privacy for the entire family. Experience outdoor living at its finest in the expansive backyard. Whether you're hosting summer cookouts or simply enjoying an evening under the stars on your deck with spectacular views; the possibilities are endless. The community beach, marina, pier, boat ramp, playground and more are just steps away!! Welomce Home to 1220 Grove Ave.

SHORT SALE APPROVED AT LIST PRICE! This charming three-bedroom, one-bathroom house presents an exceptional investor opportunity in peaceful Shady Side. The property offers excellent renovation potential, allowing you to customize and add value while creating possible rental income streams. Enjoy convenient parking and generous outdoor space perfect for relaxation or entertainment. The spacious lot provides room for expansion or landscaping creativity. Located in a desirable neighborhood just minutes from scenic Snug Harbor Park, you'll appreciate the tranquil residential setting with easy access to recreational activities.

Calling all investors, second-home seekers, and visionaries-this is the project youve been waiting for! AND it just got better with a price improvement!! 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**

Perfect time to buy this updated home with a detached garage in the beautiful Chesapeake Bay front communnity of Idlewilde! Main level bedroom and full bathroom, waterview from front second level bedroom, and off street parking. This home has been completely updated with the main level having luxury vinyl flooring and fresh paint. The spacious kitchen has granite countertops, wood cabinets, and stainless steel appliances. Both bathrooms have beautiful ceramic tile and luxury vinyl flooring. The yard is fully fenced and includes a detached garage with off street parking. The community pier, which is a 2-minute walk, is on the Chesapeake Bay and has amazing views of the Bay Bridge. The Idlewilde community is a peaceful retreat location that is close to many shops and restaurants.

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. Brand new a/c. 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 combined living and dining rooms to the nice sized kitchen with appliances and main level bedroom and bath. There is a full bath on each level and three more bedrooms on the upper level. The sunroom with wide windows and lots of natural light has 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 an unfinished upper level. Home is located in a water-oriented community and is conveniently close to the beach, marina and Shady Side attractions. NOTE - Buyers winning the Highest & Best must understand that they participated in a Highest & Best, Multiple Offers Situation and that any requests to the Seller for Special Concessions, Repairs or Switch in Financing could result in the Seller terminating and retaining Buyer's EMD.