Shady Side Real Estate

Shady Side Real Estate

Welcome to Shady Side, Maryland – a hidden gem nestled in the scenic landscapes of Anne Arundel County. This charming waterfront community offers a unique blend of tranquility and vibrant local culture, making it an ideal place to call home.

Shady Side is bordered by the serene waters of the Chesapeake Bay, providing residents with stunning views and endless opportunities for outdoor activities. Whether you enjoy sailing, fishing, or simply taking a leisurely stroll along the picturesque shoreline, this community embraces the beauty of nature. The local parks and nature reserves are perfect for family outings, picnics, and exploring the diverse wildlife that thrives in this coastal paradise.

The heart of Shady Side is its friendly community spirit. With a rich history rooted in maritime traditions, the area is home to charming local shops, delightful eateries, and a welcoming atmosphere. From fresh seafood markets to cozy cafes, the culinary scene here celebrates the flavors of the Bay. Plus, the annual community events and festivals foster a sense of belonging, where neighbors become friends and memories are made.

Education is a priority in Shady Side, with access to quality schools that cater to the needs of families. The nearby amenities of Annapolis and Washington D.C. are easily accessible, providing residents with a perfect balance between serene living and urban convenience.

Discover the allure of Shady Side, where the beauty of nature meets the warmth of community. Whether you’re looking for a peaceful retreat or an active lifestyle, this charming town has something for everyone. Come and experience the magic of Shady Side – your dream home awaits!

Newest Listings in Shady Side

6285 Shady, Shady Side
$695,000
4 Beds ⋅ 3 Baths
Endless potential in this versatile property — live in one side and run your business from the other, or use the entire building for commercial use. Originally the Shady Side Post Office, this character-filled building sits on just over half an acre with approximately 400 feet of road frontage, offering excellent visibility and easy access Highlights: C1 commercial zoning — flexible uses Live/work configuration or full commercial conversion Multiple offices / bedrooms 3 Bath rooms 2 kitchens and 2 laundry areas Just over 0.5 acre lot with 400' road frontage Suitable for: accountant, attorney, construction office, daycare, antiques, boat sales/service, retail, studio, café, professional offices, and more Why this property: Great exposure and versatility make this an ideal opportunity for owner-operators or investors looking to attract customers and create a distinctive business presence. High frontage and flexible zoning mean almost any business concept could work here.

6285 Shady, Shady Side

Listing courtesy of Long & Foster Real Estate, Inc.. Contact:

6508 Shady, Shady Side
$834,990
4 Beds ⋅ 3 Baths
This to-be-built custom modern farmhouse 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. Note: As the construction of this home has not been completed, pictures are from similar models and/or renderings.

6508 Shady, Shady Side

Listing courtesy of HomeSource Pro Real Estate. Contact:

4922 Lerch Dr, Shady Side
$699,000
3 Beds ⋅ 3 Baths
You can't beat the price for the WATERFRONT lifestyle in the Chesapeake Bay area! This stunning, open concept, 3-bedroom, 3-bath home was built in 2005 and has a PRIVATE dock -- blending modern updates, natural light, and serene water views. This home is the ideal size—not too big, not too small—offering the perfect balance of comfort, function, and privacy! Step inside an inviting open-concept main level to find luxury plank flooring throughout, and a cozy fireplace that anchors the living space. The chef’s kitchen is a showstopper, featuring a spacious island, sleek countertops, white cabinetry, and stainless appliances—ideal for entertaining and everyday living. The main level also offers a bedroom and full bath! The upper level boasts a dreamy primary suite overlooking the water, bathed in sunlight and featuring new, expansive windows . Enjoy the expansive STUNNING walk-in closet and spa-like en-suite bath with dual vanity, soaking tub, wainscoting, and a beautifully tiled frameless glass shower. Two additional bedrooms (one on main level) and bathrooms provide comfort , style and functionality with plenty of room for everyone! Outdoor living is just as special—this quiet retreat features a private dock, a fenced backyard, a paver patio and plenty of storage. Picture mornings with coffee and sunrise views, evenings on the patio watching the sunset reflect across the water, or weekends spent crabbing, kayaking, fishing, boating right from your own backyard! Not to forget a new roof (2024)! Situated in Shady Side, you’ll love the easy access to the Bay & only 25 minutes to Annapolis, 40 minutes to Washington, D.C., and 45 minutes to Northern Virginia. This home offers the perfect balance of waterfront tranquility and city convenience. So many local marinas, restaurants & the Chesapeake Yacht Club is nearby with memberships and slips available! Don’t miss this rare opportunity to occupy a turn-key waterfront property at this price point!

4922 Lerch Dr, Shady Side

Listing courtesy of Samson Properties. Contact:

1504 Cedarhurst Rd, Shady Side
$480,000
4 Beds ⋅ 2 Baths
Nestled in the charming Cedarhurst on the Bay community, this delightful Cape Cod home offers a serene lifestyle with easy access to the beautiful river nearby. With four spacious bedrooms and two full bathrooms, this residence is perfect for creating lasting memories. The inviting living area features a cozy gas fireplace, ideal for gathering on cool evenings. Enjoy the outdoors on your generous 0.27-acre lot, complete with a shed for extra storage. The attached garage and ample driveway space provide convenience for you and your guests. With navigable water access, you can embrace a lifestyle filled with boating and fishing adventures. Cedarhurst on the Bay is a welcoming community that values connection and outdoor enjoyment, making it a wonderful place to call home. Experience the perfect blend of comfort and community in this lovely property! Cedarhurst on the Bay amenities include, picnic area, playground, fishing and crabbing pier and community house. Brand new carpets throughout the home, Exterior windows replaced 2026, new roof and gutters in 2025, new crawl space encapsulation 2024, HVAC replaced 2021.

1504 Cedarhurst Rd, Shady Side

Listing courtesy of Compass. Contact:

4734 Idlewilde Rd, Shady Side
$409,990
3 Beds ⋅ 2 Baths
One level living in the serene community of Idlewilde, this charming ranch-style home offers a perfect blend of comfort and functionality. With 1,339 square feet of thoughtfully designed space, this home features three bedrooms and two full bathrooms, ideal for both relaxation and entertaining. The family room, conveniently located off the kitchen is perfect for entertaining, while the formal dining room sets the stage for memorable meals.The property boasts granite counter tops, stainless steel appliances, including a built-in microwave, dishwasher, and electric range, making meal prep a breeze. The breakfast nook in the kitchen provides the perfect spot for the kitchen table for causul daily meals with your household. A dedicated laundry area with a washer and dryer adds to the home's practicality. Outside, the 0.17-acre lot features private access to the West River with the community pier! Take in the sunsets just a short stroll away, perfect for those who appreciate nature and water activities. A concrete driveway accommodates up to four vehicles, ensuring ample parking for guests. With its excellent condition and thoughtful layout, this home is a true gem, ready for you to call this your very own "Home Sweet Home" 100% financing approved with the no downpayment program available!

4734 Idlewilde Rd, Shady Side

Listing courtesy of RE/MAX One. Contact:

4901 Idlewilde Rd, Shady Side
$145,000
Discover an extraordinary opportunity to own a stunning 1.09-acre parcel of land. Nestled in a serene setting, this exceptional lot backs to lush trees, offering a private sanctuary that seamlessly blends nature with sophistication. Imagine crafting your dream estate amidst the tranquil backdrop of towering trees. Envision grand residence designed to your specifications, complete with expansive outdoor spaces that invite entertaining and relaxation. The natural beauty surrounding the property provides an idyllic setting for a luxurious garden, an outdoor living area that captures the essence of leisure. The absence of an association fee means you have the freedom to create without restrictions, allowing your vision to flourish. With no association amenities to limit your creativity, you can design a lifestyle that reflects your unique tastes and desires. This is a rare chance to embrace exclusivity and privacy in a location that feels both secluded and connected. The lot's generous size offers ample space for a sprawling estate, complete with all the high-end features you desire. Picture expansive windows that frame the picturesque views, gourmet kitchens equipped with top-of-the-line appliances, and lavish master suites that serve as personal retreats. The possibilities are endless, limited only by your imagination. This property is more than just land; it's an invitation to a lifestyle defined by tranquility. Whether you seek a peaceful retreat from the hustle and bustle or a vibrant space for entertaining, this lot provides the perfect foundation for your vision. Seize this rare opportunity to create a luxurious haven that reflects your personal style and aspirations. With its unparalleled natural surroundings and the promise of a sophisticated lifestyle, this property is poised to become the backdrop for your most cherished memories. Don't miss your chance to invest in a future filled with elegance and serenity. Your dream home awaits.

4901 Idlewilde Rd, Shady Side

Listing courtesy of Long & Foster Real Estate, Inc.. Contact:

1244 Pine Ave, Shady Side
$699,000
4 Beds ⋅ 2 Baths
Come Live the Bay Lifestyle! Welcome to 1244 Pine Avenue, a charming Chesapeake Bay retreat in Shady Side, Maryland, offering beautiful water and marina views, exceptional outdoor living, and the relaxed charm of coastal Maryland. Wake up to breathtaking sunrises, watch sailboats pass by, and enjoy peaceful evenings overlooking the bay. Located in the desirable Cedarhurst community, this inviting home offers the perfect opportunity to embrace waterfront living with a residents only marina across the street. Inside, the light filled living and dining areas feature a fireplace and expansive picture windows framing beautiful water views. The updated kitchen is appointed with green cabinetry, granite countertops, stainless steel appliances, and a gas range. Just beyond, a charming screened-in porch creates the perfect setting for morning coffee or al fresco dining. The spacious rear family room offers additional living space with sweeping bay views and sliding glass doors opening to the deck and fully fenced backyard, creating a seamless connection between indoor and outdoor entertaining. The main level includes a versatile bedroom ideal for guests or a home office, while upstairs, three generously sized bedrooms offer comfortable accommodations, including a spacious primary bedroom with beautiful Chesapeake Bay views. Additional highlights include a newer roof, new washer and dryer, generous outdoor entertaining areas, and a large storage shed is wired and has electricity. For boating enthusiasts, the nearby residents only marina offers boat slips reportedly available for $350 annually, providing convenient access to the Chesapeake Bay. Cedarhurst's waterfront community center, playground, beach, and picnic areas further enhance the neighborhood's coastal lifestyle. Whether as a primary residence or weekend retreat, 1244 Pine Avenue offers an exceptional combination of water views, generous outdoor living, boating access, and the tranquility of Shady Side's beloved Chesapeake Bay community.

1244 Pine Ave, Shady Side

Listing courtesy of Compass. 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
$574,990
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
$464,999
3 Beds ⋅ 3 Baths
REDUCED ALMOST 25K >>> HURRY THIS PROPERTY WILL NOT LAST LONG AT THIS PRICE>>>>.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 + $5,000 Closing Help! December Delivery at Cedarhurst on the Bay* Welcome to Cedarhurst on the Bay, where every day feels like a coastal escape. This beautifully crafted home blends timeless charm with modern living, with stunning Chesapeake Bay views and classic board-and-batten siding. The open-concept main level is filled with natural light, connecting the dining area and family room. The kitchen features an oversized quartz island, stainless steel appliances, and generous cabinetry, and a main-level home office or flex room adds versatility. Upstairs, the owner’s suite offers large windows, an expansive walk-in closet, and a spa-inspired bath with a luxury shower. Outside, Cedarhurst’s four acres of community-owned waterfront include a community center, playground, picnic areas, ball fields, and open lawns overlooking the wetlands and water. With direct access to the Bay, boating, fishing, and sunset views are always within reach. December will be here before you know it. Don’t wait. Schedule your appointment today! *Closing cost assistance terms and conditions apply.

1235 Spruce Ave, Shady Side

Listing courtesy of Blackwell Real Estate, LLC. Contact:

1411 Haile Pkwy, Shady Side
$500,000
4 Beds ⋅ 3 Baths
Motivated Seller. Owners have relocated. Will consider any reasonable offer. 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:

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