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

1411 Haile Pkwy, Shady Side $525,000

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. Mo...

4 Beds
3 Baths

Courtesy of TTR Sotheby's International Realty

Listing courtesy of TTR Sotheby's International Realty. Contact: 4106733344

5060 Lerch Dr, Shady Side $1,100,000

Waterfront living at its finest in Avalon Shores on South Creek! This 3-bedroom, 4.5-bath home features a versatile study/bonus room, beautiful wood floors, updated kitch...

3 Beds
5 Baths

Courtesy of Redfin Corp

Listing courtesy of Redfin Corp. Contact: 3016586186

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

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

1193 Oak Ave, Shady Side $415,000 ▼

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

1704 Maryland Ave, Shady Side $349,900

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: 8882193009

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: kelly.thompson@cbmove.com

6066 Shady Side Rd, Shady Side $699,000 ▼

MAJOR PRICE IMPROVEMENT AND $5,000 SELLER CONTTRIBUTION TOWARDS BUYER'S CLOSING WITH ACCEPTABLE CONTRACT. Rare Opportunity with 2 detached homes on 4 Flat, Usable Acres ...

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:

4701 Girton Ave, Shady Side $1,600,000

BY APPOINTMENT ONLY Saturday September 12th 12-3. Rich in history, timeless in character, and unmatched in location, this extraordinary waterfront estate traces its origi...

8 Beds
7 Baths

Courtesy of TTR Sotheby's International Realty

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