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

1316 Juniper St, Shady Side $549,900

This Stylish New home is move in ready and just in time to enjoy the summer breezes at the community Beach areas and play grounds! It is ready for your personal touch to ...

4 Beds
3 Baths

Courtesy of Long & Foster Real Estate, Inc.

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

1211 Linton Ln, Shady Side $799,000

None

3 Beds
1 Baths

Courtesy of Keller Williams Capital Properties

Listing courtesy of Keller Williams Capital Properties. Contact:

4958 Lerch Dr, Shady Side $995,000

Exceptional value for this exquisite, recently renovated coastal waterfront retreat, offering the perfect blend of luxury, comfort, and breathtaking water views throughou...

3 Beds
2 Baths

Courtesy of Beam Realty Group, Inc.

Listing courtesy of Beam Realty Group, Inc.. Contact: 4438656969

1237 Spruce Ave, Shady Side $619,990

Enjoy water views of the community harbor with 60 boat slips and direct access to the Chesapeake Bay—a dream setting for boating and coastal living. This beautifully craf...

4 Beds
3 Baths

Courtesy of RE/MAX United Real Estate

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

6372 Shady Side Rd W, Shady Side $380,000

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: admin@mdreoconnection.com

1241 Johnson Dr, Shady Side $750,000

**OPEN HOUSE SAT 7/25 11am-1pm**New roof & gutters installed last week! Welcome to your own private waterfront retreat nestled at the peaceful head of South Creek, where ...

3 Beds
3 Baths

Courtesy of RE/MAX One

Listing courtesy of RE/MAX One. Contact: 4105356291

1432 Heile/Haile Pkwy, Shady Side $124,950 ▼

REDUCED $45,000.00 ALL CASH OFFERS-FIRE DAMANGED INTERIOR- TOTAL REHAB-2 BR 1 Bath quiet secluded street. New Homes being built on same street. Owner reserves right to ac...

2 Beds
1 Baths

Courtesy of Flag Real Estate Inc.

Listing courtesy of Flag Real Estate Inc.. Contact:

5209 Al Jones Dr, Shady Side $149,900

WATERFRONT OPPORTUNITY!! Discover the perfect setting to build your dream home or weekend retreat on this waterfront lot offering breathtaking views of the Chesapeake Bay...

Courtesy of CENTURY 21 New Millennium

Listing courtesy of CENTURY 21 New Millennium. Contact: 4439689595

4734 Oak Rd, Shady Side $625,000

Enjoy breathtaking views of the Chesapeake Bay from this charming home in the quaint waterfront community of Felicity Cove. The ground level features two bedrooms (one wi...

4 Beds
3 Baths

Courtesy of Schwartz Realty, Inc.

Listing courtesy of Schwartz Realty, Inc.. Contact:

6201 Shady Side Rd, Shady Side $399,900 ▼

Spacious 2,807 sq. ft. home offering exceptional potential for investors, multi-generational living, or rental income opportunities. The main residence features two bedro...

4 Beds
3 Baths

Courtesy of Schwartz Realty, Inc.

Listing courtesy of Schwartz Realty, Inc.. Contact:

4909 Olive St, Shady Side $490,000 ▼

Welcome to 4909 Olive Street, a newer construction three bedroom, two and a half bath home in the waterfront community of Avalon Shores. Offering a functional layout, con...

3 Beds
3 Baths

Courtesy of TTR Sotheby's International Realty

Listing courtesy of TTR Sotheby's International Realty. Contact: (410) 280-5600

4921 Olive St, Shady Side $349,900 ▼

*** CAN'T BEAT NEW PRICE. BRING ALL CLEAN, NON-CONTINGENT OFFERS! *** Coastal charm meets modern comfort in Avalon Shores! This sun-drenched, corner-lot 1940s cottage boa...

3 Beds
1 Baths

Courtesy of Redfin Corp

Listing courtesy of Redfin Corp. Contact: 3016586186