Shady Side Real Estate

Welcome to Shady Side, Maryland – a hidden gem nestled in the heart of Anne Arundel County. This picturesque waterfront community offers a unique blend of serene living and vibrant outdoor activities, making it an ideal destination for those seeking a peaceful retreat from the hustle and bustle of city life.

Shady Side is steeped in natural beauty, with its stunning views of the Chesapeake Bay and lush landscapes that invite residents to explore the great outdoors. Boasting a rich maritime history, the area is perfect for boating enthusiasts, fishing aficionados, and nature lovers alike. The nearby parks and trails provide ample opportunities for hiking, biking, and picnicking, ensuring that there's always something to enjoy in this charming locale.

The community is known for its friendly atmosphere and strong sense of camaraderie among neighbors. Local events and gatherings foster a tight-knit community spirit, making it easy to meet new friends and feel right at home. Shady Side's quaint shops and delicious eateries offer a taste of local flavor, while the nearby towns provide additional shopping and entertainment options.

Education is a priority in Shady Side, with access to highly-rated schools that cater to families with children of all ages. The area's strategic location allows for easy commuting to nearby cities such as Annapolis and Washington, D.C., making it an ideal spot for professionals seeking a balance between work and leisure.

If you're looking for a place that embodies the charm of coastal living while offering modern conveniences, Shady Side is the perfect choice. Come experience the warmth and beauty of this delightful community, where every day feels like a vacation!

Newest Listings in Shady Side

1221 Bast Ln, Shady Side $625,000

There is something special about life near the Chesapeake Bay—and 1221 Bast Lane captures it beautifully. Completely remodeled from top to bottom, this charming one-level...

4 Beds
2 Baths

Courtesy of Coldwell Banker Realty

Listing courtesy of Coldwell Banker Realty. Contact: 4102638686

1194 Oak Ave, Shady Side $499,000

Tastefully updated, magnificent and charming Home for Sale in the water-oriented community of Cedarhurst on the Bay. This Beautiful 5 bedroom 4 bathroom house will deliv...

5 Beds
4 Baths

Courtesy of Maryland Realty Company

Listing courtesy of Maryland Realty Company. Contact: 4109296161

1437 Cedarhurst Rd, Shady Side $419,000

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-lev...

3 Beds
2 Baths

Courtesy of Samson Properties

Listing courtesy of Samson Properties. Contact: 7033493900

4911 Magnolia St, Shady Side $370,000

Welcome to this charming 2-bedroom, 2-bath rambler in the desirable water community of Westelee. This well-maintained home offers comfortable one-level living with an inv...

2 Beds
2 Baths

Courtesy of RE/MAX United Real Estate

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

1500 Garst Rd, Shady Side $364,000

Welcome to 1500 Garst Road in the water oriented Columbia Beach community of Shady Side. Enjoy private community access to Herring Bay and the Chesapeake Bay lifestyle, w...

2 Beds
2 Baths

Courtesy of HomeSmart

Listing courtesy of HomeSmart. Contact: 3013524065

1495 Cedarhurst Rd, Shady Side $430,000

Large lot ready for you to build your private compound! 8.5 acres contains wetland areas. Located in a water-privileged community and two blocks to the Chesapeake Bay. C...

Courtesy of Taylor Properties

Listing courtesy of Taylor Properties. Contact:

1175 Maple Ave, Shady Side $540,000

Welcome home to this beautifully maintained split-foyer in Cedarhurst on the Bay, Shadyside's sought-after water-privilege community. Built in 2015, this 3-bedroom, 2.5-b...

3 Beds
3 Baths

Courtesy of Cummings & Co. Realtors

Listing courtesy of Cummings & Co. Realtors. Contact: (410) 823-0033

6152 Shady Side Rd, Shady Side $54,900

SELLER FINANCING AVAILABLE! 1.53-acre residential tract in Shady Side, Maryland is an unmatched deal! Located at 6152 Shady Side Rd, this spacious property is tax-assess...

Courtesy of Rise Real Estate, LLC

Listing courtesy of Rise Real Estate, LLC. Contact: 2025569721

1193 Oak Ave, Shady Side $425,000

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...

3 Beds
3 Baths

Courtesy of RE/MAX One

Listing courtesy of RE/MAX One. Contact: 4105356291

1220 Grove Ave, Shady Side $475,000

Welcome to the Waterfront Community of Cedarhurst by the Bay tucked away on the quiet Shady Side Penninsula. This Spacious 5 Bedroom, 2 Full Bath home sits just steps awa...

5 Beds
2 Baths

Courtesy of Coldwell Banker Realty

Listing courtesy of Coldwell Banker Realty. Contact: kelly.thompson@cbmove.com

6066 Shady Side Rd, Shady Side $775,000 ▼

Rare Opportunity with 2 detached homes on 4 Flat, Usable Acres in Shady Side! Welcome to 6066 Shady Side Rd, an incredible property offering endless versatility, income...

5 Beds
3 Baths

Courtesy of Century 21 Downtown

Listing courtesy of Century 21 Downtown. Contact:

4721 Oak Rd, Shady Side $998,000

Waterfront living at its finest! This custom-built Chesapeake Bay home offers breathtaking panoramic views stretching all the way to the Bay Bridge. Meticulously maintain...

4 Beds
3 Baths

Courtesy of Schwartz Realty, Inc.

Listing courtesy of Schwartz Realty, Inc.. Contact: