Shady Side Homes for Sale

Welcome to Shady Side, Maryland – a hidden gem nestled within the picturesque Anne Arundel County. This charming waterfront community offers a unique blend of tranquility and vibrant coastal living, making it an ideal destination for those seeking a serene lifestyle just a stone's throw from the hustle and bustle of city life.

Shady Side is renowned for its stunning views of the Chesapeake Bay, where residents can enjoy breathtaking sunsets and a variety of outdoor activities, from boating and fishing to hiking and birdwatching. The area is rich in natural beauty, with lush parks and scenic trails that beckon nature enthusiasts and families alike. With a close-knit community vibe, Shady Side is perfect for those looking to connect with neighbors and participate in local events throughout the year.

For homebuyers, Shady Side presents an array of charming properties that cater to diverse tastes and budgets. From cozy cottages and waterfront bungalows to spacious family homes, there’s something for everyone in this idyllic locale. Many homes boast modern amenities while retaining the character and charm that define the area. Imagine waking up to the sound of waves lapping at the shore and enjoying leisurely afternoons on your porch, taking in the stunning views.

Whether you’re searching for a permanent residence or a weekend getaway, Shady Side offers an inviting atmosphere and a strong sense of community. Explore the homes for sale today and discover the perfect place to call your own in this enchanting corner of Maryland!

Newest Shady Side Homes for Sale

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:

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

1582 Snug Harbor Rd, Shady Side $619,900

**Open House this Sunday July 26th 12-2pm!** Rare 1-acre private lot located in sought after Idlewilde Acres backing up to Jack Creek Park! Upgrades include: 2023 enlarg...

4 Beds
3 Baths

Courtesy of Maryland Waterfront Properties LLC

Listing courtesy of Maryland Waterfront Properties LLC. Contact: 7036281386