Shady Side Homes under $900,000

Shady Side Homes under $900,000

Welcome to Shady Side, Maryland, a hidden gem nestled in the heart of Anne Arundel County. This charming waterfront community, located along the picturesque shores of the Chesapeake Bay, offers a unique blend of serene living and vibrant coastal culture. With its stunning views, friendly atmosphere, and close-knit community, Shady Side is the perfect place to call home.

Shady Side boasts an array of outdoor activities, making it ideal for nature enthusiasts and families alike. Enjoy leisurely strolls along the scenic trails of the nearby parks or indulge in water sports such as kayaking and fishing. The area's natural beauty is complemented by local eateries and shops that add to its quaint charm.

For those seeking a home in this idyllic setting, Shady Side offers a variety of properties priced under $900,000. Whether you're looking for a cozy cottage with waterfront access, a spacious family home nestled among mature trees, or a modern retreat with stunning bay views, you’ll find an array of options that cater to diverse tastes and lifestyles.

Living in Shady Side means embracing a lifestyle that balances tranquility and community spirit. With excellent schools, local events, and friendly neighbors, you’ll find that this charming town has everything you need to create lasting memories. Explore the possibilities of calling Shady Side home, where the beauty of nature meets the warmth of community living. Discover your dream home today in this enchanting Maryland enclave!

Newest Shady Side Homes under $900,000

1244 Pine Ave, Shady Side
$749,900
4 Beds ⋅ 2 Baths
Welcome to 1244 Pine Avenue, a charming Chesapeake Bay waterfront retreat in Shady Side, Maryland, offering beautiful water and marina views, generous indoor-outdoor living, and a peaceful setting rooted in the boating lifestyle of southern Maryland The offering encompasses approximately 0.34 acres across Lots 16, 17, and 28, providing additional land and versatility rarely found in a waterfront community. Lots 16 and 17 are currently taxed together, while Lot 28 is separately deeded. Set within an established waterfront community, this inviting home offers the rare opportunity to enjoy everyday life just moments from the water, with a marina approximately one block (slips available for rent) away and a waterfront community center, playground, and picnic area nearby. Inside, the welcoming living and dining spaces are anchored by a fireplace and framed by picture windows that draw the surrounding water views into the home. The classic kitchen is thoughtfully appointed with green cabinetry, granite countertops, stainless steel appliances, and a gas range, creating a bright and functional space for everyday cooking and entertaining. Just beyond the kitchen, a screened-in porch extends the living space outdoors and provides an ideal setting for al fresco dining, morning coffee, or crisp fall evenings overlooking the peaceful surroundings. An expansive family room at the rear of the home offers additional space to gather and relax, with large windows capturing views toward the bay and sliding glass doors opening directly to the deck and backyard. A main-level bedroom adds valuable flexibility as a guest suite, home office, or additional living space. Upstairs, three generously proportioned bedrooms provide comfortable accommodations, including a spacious primary bedroom spanning one side of the home and offering lovely Chesapeake Bay views. Well appointed bathrooms throughout complete this turn-key home. Outside, the deck and yard create an effortless extension of the home, while a large storage shed provides additional functionality. Perfectly positioned in Shady Side, Maryland, 1244 Pine Avenue offers the relaxed character and natural beauty of Chesapeake Bay living with convenient access to the water, the nearby marina, Cedarhurst community amenities, and the surrounding towns of southern Anne Arundel County. Whether you're seeking a primary residence, weekend retreat, or a home that embraces the region's celebrated waterfront lifestyle, this distinctive property combines water views, flexible living space, multiple outdoor areas, and exceptional proximity head out on the Chesapeake Bay.

1244 Pine Ave, Shady Side

Listing courtesy of Compass. Contact:

1462 Columbia Beach Rd, Shady Side
$349,900
3 Beds ⋅ 3 Baths
MECHANICS/WORKSHOP DREAM. Nestled in the serene Shady Side community, this charming ranch-style home offers a perfect blend of comfort and functionality. With 1,489 square feet of thoughtfully designed living space, this residence features three inviting bedrooms and two full bathrooms, ideal for both relaxation and entertaining. Step inside to discover a warm and welcoming interior, highlighted by a cozy breakfast area and a combination kitchen/dining space that encourages gatherings. The kitchen is equipped with stainless steel appliances, including a gas oven/range and a convenient dishwasher, making meal prep a delight. Enjoy the ease of main-floor laundry and the comfort of ceiling fans throughout. The exterior of the home is equally appealing, featuring low-maintenance vinyl siding and a spacious lot of over half an acre that backs to lush trees, providing a tranquil backdrop. Outdoor living is enhanced by a charming patio and porch, perfect for morning coffee or evening relaxation. The property also includes an oversized detached garage with car lift and a shed, offering ample storage and workspace. Perfect for the mechanic with side jobs or projects to work on. Parking is a breeze with a circular gravel driveway and additional spaces for guests or projects. This home is not just a place to live; it's a sanctuary where you can unwind and create lasting memories. Experience the perfect blend of indoor comfort and outdoor beauty in this delightful property.

1462 Columbia Beach Rd, Shady Side

Listing courtesy of RE/MAX Realty Group. Contact:

1183 Cedar Ave, Shady Side
$499,900
4 Beds ⋅ 3 Baths
Nestled in the charming Cedarhurst on the Bay community, this delightful split foyer home offers a perfect blend of comfort and convenience. This well-maintained residence features four spacious bedrooms and three full bathrooms, ideal for both relaxation and entertaining. Step outside to discover a serene outdoor oasis, complete with a hot tub for unwinding after a long day. The property also includes a garage and a shed, providing ample storage for all your needs. Enjoy the beauty of nature with easy access to the stunning Chesapeake Bay, where community docks invite you to explore the water and create lasting memories. The neighborhood is known for its friendly atmosphere and strong sense of community. Residents benefit from nearby parks, perfect for leisurely strolls or picnics, and excellent public services that enhance the quality of life. With a walkout basement and a cozy fireplace, this home is designed for comfort and warmth. Experience the joys of living in Cedarhurst on the Bay, where community spirit meets the tranquility of waterfront living. This home is not just a place to live; it's a place to thrive. professional pictures to come.

1183 Cedar Ave, Shady Side

Listing courtesy of United Real Estate Premier. Contact:

5314 Al Jones Rd, Shady Side
$599,990
4 Beds ⋅ 3 Baths
Home is ready for immediate occupancy. 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 LVP flooring through out (Carpet in 2 bedrooms). 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 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. Actual features, finishes, and layouts may vary. Flood insurance is approximately $650.00 year. $5,000 in closing assistance with preferred lender and title company.

5314 Al Jones Rd, Shady Side

Listing courtesy of Schwartz Realty, Inc.. Contact:

1240 Hawthorne St, Shady Side
$489,900
3 Beds ⋅ 3 Baths
Nestled in the charming Avalon Shores community, this delightful Colonial home offers a perfect blend of comfort and modern living. This 3 bedroom and 2.5 bath has a thoughtfully designed space, ideal for both relaxation and entertaining. Step inside to discover an inviting open floor plan adorned with beautiful LVT floors. The huge eat-in kitchen with under cabinet lighting and stainless appliances is great for a family & entertaining with a huge dining area off kitchen. The spacious primary suite offers a serene retreat with new LVT floors and a newly remodeled bath with new vanity, new LVT floors, lighting and toilet. The separate laundry room upstairs is and added bonus!! Outside the extensive hardscape with new concrete walkways complements the lovely 17 x17 back patio and 28x10 back deck and front porch all perfect for enjoying morning coffee or evening gatherings with family and friends. The level lot with maintenance free fenced in yard provides a lovely outdoor space, while the attached garage and asphalt driveway ensure ample parking. The home is wired with a full subpanel for in house generator. There is an encapsulated crawlspace with Aquaguard w/ EZ Breath climate control and dehumidifier. Residents of Avalon Shores enjoy exclusive access to common grounds and picnic areas, a pier/dock, and playground, fostering a sense of community and outdoor enjoyment. With water and lake privileges, you can embrace a lifestyle filled with leisure and recreation. This home is not just a property; it's a sanctuary where family memories are made. Experience the perfect blend of comfort, convenience, and community in this exceptional family oriented home.

1240 Hawthorne St, Shady Side

Listing courtesy of RE/MAX Leading Edge. Contact:

1235 Spruce Ave, Shady Side
$599,990
4 Beds ⋅ 3 Baths
HUGE Price adjustment is complete and Schaefer Homes is now offering $5,000 in closing cost assistance - don't wait! December Delivery — the life you've been dreaming of is almost here! Welcome to Cedarhurst on the Bay, where every day feels like a coastal escape. This beautifully crafted home is the perfect blend of timeless charm and modern living, set against a backdrop of stunning Chesapeake Bay views that simply never get old. From the moment you arrive, the classic board-and-batten siding and striking exterior create an immediate sense of quality and character that carries beautifully throughout the entire home. Inside, soaring natural light fills the open-concept main level, where the dining area and family room connect seamlessly to create a warm, effortless flow perfect for both quiet evenings and lively get-togethers. The kitchen is nothing short of spectacular, featuring an oversized quartz island, stainless steel appliances, and generous cabinetry that makes cooking and entertaining an absolute pleasure. Need a dedicated workspace or a room to call your own? The main-level home office or flexible choice room delivers exactly that. Upstairs, the owner's suite is a true haven — bathed in natural light through large windows, complete with an expansive walk-in closet and a spa-inspired bath featuring a luxury shower that turns every evening into a retreat. Outside your front door, Cedarhurst's extraordinary four acres of community-owned waterfront property sets this neighborhood apart from anything else in the area. Sip your morning coffee as sunrises illuminate the Bay, stroll to the community center and playground, or spend the afternoon at the picnic areas, ball fields, and open lawns that overlook the wetlands and water. Watch sailboats drift by, spot local waterfowl, and take in the sight of watermen working the Bay — a living piece of Maryland's rich maritime heritage right in your own backyard. With direct access to the Chesapeake Bay, the water is always within reach for those who love to boat, fish, or simply soak in the coastal lifestyle. December will be here before you know it — schedule your appointment today and make Cedarhurst home!

1235 Spruce Ave, Shady Side

Listing courtesy of Blackwell Real Estate, LLC. Contact:

4922 Dogwood St, Shady Side
$425,000
3 Beds ⋅ 3 Baths
Seller is offering rate buy down credit ! Sleek Completely rebuilt and reimagined, this 3-bedroom, 2.5-bath cottage with a palette that feels equal parts cabin and studio. Every system, surface, and finish is new: Set on the West River/Chesapeake Bay peninsula in Avalon Shores of Shady Side — 25 miles south of Annapolis known for boating, crabbing, beaches and . This address puts you minutes from marinas, Franklin Point State Park, and bay sunsets, it's a rare combination of turnkey renovation and authentic bay-town character. Brand new Pella windows, roof and siding. Hardwood floors throughout. Stylish tile bathrooms. Brand new asphalt driveway. Bluestone steps with iron railings. Bright open floor plan. Double lot. Brand new electrical including heavy up panel, all new plumbing system and ductwork and HVAC equipment. Taken down to the studs with new insulation and drywall.

4922 Dogwood St, Shady Side

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

4924 Kellam Rd, Shady Side
$399,000
2 Beds ⋅ 1 Baths
This delightful 1930s ranch-style cottage offers a perfect blend of vintage charm and modern comfort. Set on a generous 1.25-acre lot, the property boasts ample outdoor space, ideal for gardening, entertaining, or simply enjoying the tranquility of nature. An inviting outbuilding adds versatility, whether you envision a workshop, studio, or extra storage space. The expansive driveway ensures convenient parking for you and your guests, making gatherings a breeze. Imagine sipping your morning coffee on a sun-drenched patio, surrounded by the beauty of your own private oasis. With two cozy bedrooms and a well-appointed full bathroom, this home is designed for comfort and ease. The layout encourages a warm, inviting atmosphere, perfect for creating lasting memories. This property is not just a house; it's a place where you can truly feel at home. Embrace the opportunity to make this charming cottage your own and enjoy the serene lifestyle it offers. Don't miss your chance to experience the perfect blend of comfort and outdoor living!

4924 Kellam Rd, Shady Side

Listing courtesy of District Pro Realty. Contact:

1411 Haile Pkwy, Shady Side
$525,000
4 Beds ⋅ 3 Baths
Now is the time to take a fresh look at this beautifully designed 2022-built home, where modern style, thoughtful details, and a peaceful wooded setting come together. Move-in ready and filled with natural light, this home offers the space and flexibility buyers are looking for—without the wait or expense of new construction. Step inside to an open two-story foyer and into the inviting main living area with vaulted ceilings. Nine-foot ceilings throughout the home, charming cottage-style windows, and an open layout create an airy, comfortable feel. LVP flooring flows throughout the living room, kitchen, and wide hallway, making everyday living and entertaining effortless. The kitchen is a standout, featuring granite countertops, soft-close cabinetry, oil-rubbed bronze fixtures, and a center island with seating. There’s plenty of room for a dining table, creating an easy gathering space for family and friends. The main level offers three bedrooms including a spacious owner’s suite with two closets providing excellent storage, while the distinctive en-suite bath features dual sinks, granite countertops, a walk-in shower, custom wall trim. The two additional bedrooms feature custom molding, decorative wall treatments, and stylish finishes. The hall bath includes a granite vanity and shower/tub combination. And there’s even more living space downstairs! The lower level features a large recreation room with sliding glass doors to the backyard, a flexible fourth bedroom perfect for guests, a home office, gym, or hobby room, plus another full bath. This versatile lower level gives you room to spread out, work from home, entertain, or accommodate overnight guests. Outside, raised garden beds are ready for your favorite flowers, herbs, and vegetables. The mature, wooded backdrop provides a peaceful sense of privacy and a beautiful setting to enjoy year-round.

1411 Haile Pkwy, Shady Side

Listing courtesy of TTR Sotheby's International Realty. Contact:

1437 Cedarhurst Rd, Shady Side
$419,000
3 Beds ⋅ 2 Baths
Welcome to 1437 Cedarhurst Road in Shady Side, MD! This beautifully updated 3-bedroom, 2-full-bath rancher was completely remodeled in 2023 and offers comfortable one-level living with fresh, modern finishes throughout. Major updates include a newer HVAC system, newer roof and gutters, and a new water filtration system. Additional highlights include a one-car garage, abundant parking, and a spacious backyard with a storage shed, providing plenty of room for outdoor equipment, tools, and additional storage. Located just minutes from the waterfront, this property offers convenient access to the Chesapeake Bay and opportunities for boating, kayaking, fishing, crabbing, and other waterfront activities. With extensive updates, generous outdoor space, and a location close to the water, 1437 Cedarhurst Road has so much to offer!

1437 Cedarhurst Rd, Shady Side

Listing courtesy of Samson Properties. Contact:

1193 Oak Ave, Shady Side
$409,990
3 Beds ⋅ 3 Baths
Welcome to the Chesapeake Bay lifestyle in the waterfront community of Cedarhurst! Just one block from the Bay, this picture-perfect Colonial combines classic curb appeal, comfortable living spaces, and the kind of community amenities that make everyday life feel a little more like vacation. Start your mornings on the welcoming front porch and spend summer evenings entertaining on the rear deck overlooking the lush landscaping. Inside, the inviting living room features a cozy wood-burning fireplace, while the spacious kitchen offers painted cabinetry, stainless steel appliances, and plenty of room for an eat-in dining area. Upstairs, you’ll find three generously sized bedrooms, including a spacious primary suite with vaulted ceilings and a private en-suite bath. Two additional bedrooms share a dedicated hall bath. Major updates include a NEW ROOF in 2022 and HVAC replaced in 2021. But the Cedarhurst lifestyle may just be the best part! Stroll down to the community waterfront where you’ll find a picnic area and playground overlooking the Chesapeake Bay—the perfect spot to catch the sunset to your right or watch the sunrise to your left. Launch your kayak or jet ski from the community boat ramp, or take advantage of available boat slips for just $400 per year, per slip. Residents also have exclusive access to rent the Cedarhurst Community Center for parties and gatherings. From boating and waterfront picnics to catching both sunrise and sunset along the Bay, this is more than a home—it’s the Chesapeake lifestyle you've been looking for. This property is 100% financing approved, no downpayment local program available! Welcome home!

1193 Oak Ave, Shady Side

Listing courtesy of RE/MAX One. Contact:

1704 Maryland Ave, Shady Side
$299,900
4 Beds ⋅ 2 Baths
Welcome to this charming 4-bedroom, 2-bath home in the desirable Snug Harbor community of Shady Side. Offering approximately 1,930 square feet of living space, this property features a spacious layout, detached garage, and generous yard with plenty of room to enjoy outdoor living. Conveniently located near marinas, parks, local dining, and Chesapeake Bay recreation, this home presents a wonderful opportunity to enjoy the relaxed waterfront lifestyle with easy access to Annapolis. This property has an exclusive boat slip!

1704 Maryland Ave, Shady Side

Listing courtesy of Sell Your Home Services. Contact:

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