Shady Side Homes under $500,000

Welcome to Shady Side, Maryland – a hidden gem nestled in the heart of Anne Arundel County. This charming waterfront community offers a unique blend of serene living and vibrant local culture, making it an ideal destination for families, retirees, and everyone in between. With its picturesque views of the Chesapeake Bay and a strong sense of community, Shady Side is a place where you can truly feel at home.

Shady Side boasts an array of outdoor activities, from boating and fishing to hiking along scenic trails. The nearby parks and waterfront access provide endless opportunities for adventure and relaxation. The local community is known for its friendly atmosphere, where neighbors become friends and gatherings are a common delight.

For those looking to invest in their dream home, Shady Side presents an exciting opportunity with a selection of charming homes available for under $500,000. Whether you’re searching for a cozy cottage, a spacious family home, or a waterfront retreat, you’ll find a variety of options that cater to different tastes and lifestyles. These affordable homes not only offer great value but also provide the chance to immerse yourself in a welcoming community filled with character and charm.

With its ideal location, friendly residents, and affordable housing options, Shady Side is more than just a place to live – it’s a lifestyle. Come explore what makes this delightful community so special and discover your perfect home in Shady Side today!

Newest Shady Side Homes under $500,000

1462 Columbia Beach Rd, Shady Side image

1462 Columbia Beach Rd, Shady Side $349,900

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 squar...

3 Beds
3 Baths

Courtesy of RE/MAX Realty Group

Listing courtesy of RE/MAX Realty Group. Contact:

1183 Cedar Ave, Shady Side $499,900

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 residenc...

4 Beds
3 Baths

Courtesy of United Real Estate Premier

Listing courtesy of United Real Estate Premier. Contact:

1240 Hawthorne St, Shady Side $489,900 ▼

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 thou...

3 Beds
3 Baths

Courtesy of RE/MAX Leading Edge

Listing courtesy of RE/MAX Leading Edge. Contact:

4922 Dogwood St, Shady Side $429,950

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...

3 Beds
3 Baths

Courtesy of RE/MAX United Real Estate

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

4924 Kellam Rd, Shady Side $399,000

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 s...

2 Beds
1 Baths

Courtesy of District Pro Realty

Listing courtesy of District Pro Realty. Contact:

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:

1193 Oak Ave, Shady Side $409,990 ▼

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:

1704 Maryland Ave, Shady Side $299,900 ▼

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 prope...

4 Beds
2 Baths

Courtesy of Sell Your Home Services

Listing courtesy of Sell Your Home Services. Contact:

1220 Grove Ave, Shady Side $465,000 ▼

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:

6372 Shady, Shady Side $300,000 ▼

Opportunity awaits at this charming farmhouse nestled in the waterfront community of Shady Side. Situated on a spacious lot, this home offers a peaceful setting with conv...

3 Beds
3 Baths

Courtesy of Maryland Realty Connection

Listing courtesy of Maryland Realty Connection. Contact:

1172 Cedar Ave, Shady Side $325,000

Welcome to Cedarhurst on the Bay, a charming waterfront community on the Shady Side Peninsula, conveniently located between Annapolis and Deale Maryland. This cute, updat...

3 Beds
1 Baths

Courtesy of Weichert, REALTORS

Listing courtesy of Weichert, REALTORS. Contact:

4951 Bonniewood Dr, Shady Side $470,000 ▼

Welcome to this beautiful home in the highly sought-after Avalon Shores community, offered for sale by only its original builders of the home. Situated on over one-third ...

3 Beds
3 Baths

Courtesy of Schwartz Realty, Inc.

Listing courtesy of Schwartz Realty, Inc.. Contact: