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Beds
Baths
Sq.Ft.
1432 Heile/Haile Parkway
Shady Side, MD
5209 Al Jones Drive
6201 Shady Side Road
1311 Avalon Boulevard
1500 Garst Road
4921 Olive Street
4912 Beech Street
1172 Cedar Avenue
1617 Winters Avenue
1186 & 1188 Poplar Avenue
4738 Washington Ave
1495 Shady Rest Road
4912 Mariners Drive
Haile Parkway
1445 & 1447 Haile Parkway
-1436 Haile Parkway
Pine Avenue
1205 Poplar Avenue
1199 Oak Avenue
1451 Shady Rest Road
South of Annapolis is the picturesque small town of Shady Side, where working boats still return with the day’s bounty from the sea. Nearly every home site enjoys waterfront views and many provide water access. Ranch-style homes blend with Cape Cods, bungalows, and colonials in charming neighborhoods. Many residential areas have amenities like a fishing pier, a waterfront playground, and their own swimming beach. Throughout the area, former fishing villages are transforming into bedroom communities in close proximity to one of the Chesapeake Bay’s largest marinas, Herrington Harbour North. Local festivities draw South County residents together, from parades to tree-lighting ceremonies.
Weichert Realtors is one of the nation's leading providers of Shady Side, Maryland real estate for sale and home ownership services. Contact Weichert today to buy or sell real estate in Shady Side, MD.
(Data as of 7/22/2026)
Information deemed reliable but not guaranteed.
Information Deemed Reliable But Not Guaranteed. The data relating to real estate for sale on this website appears in part through the BrightMLS Broker ReciprocitySM program, a voluntary cooperative exchange of property listing data between licensed real estate brokerage firms in which Weichert, Realtors® participates, and is provided by BrightMLS through a licensing agreement.
Real estate listings held by brokerage firms other than Weichert, Realtors® are marked with the Broker Reciprocity icon (a little black house) and detailed information about each listing includes the name of the listing broker.
The information provided by this website is for the personal, non-commercial use of consumers and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing.
Some properties which appear for sale on this website may no longer be available because they are under contract, have sold or are no longer being offered for sale.
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