Shady Side
For sale
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Shady Side, MD Homes for Sale
Welcome to an extraordinary waterfront estate offering the perfect balance of luxury, function, and efficiency on Maryland’s treasured Western Shore. This 9-bedroom, 6.5-bath residence spans 8,400+ square feet and is built to withstand the elements while embracing the serene lifestyle of the Chesapeake Bay. Set on over 2/3 of an acre with 260 feet of water frontage, this solid brick & block home was constructed with reinforced steel walls, high R-value insulation, a poured concrete foundation, and a roof system designed to withstand high winds – all topped with 40-year architectural shingles (inspected Nov. 2024). This is a true fortress disguised as a coastal retreat. Ins
Professional Photos Coming Soon! Welcome to this beautifully maintained Colonial nestled on a spacious corner lot in a peaceful cul-de-sac. Freshly painted in neutral tones, this home offers a light and airy feel throughout. The heart of the home is the stunning kitchen—featuring granite countertops, light cabinetry, and a large center island topped with butcher block, perfect for both meal prep and casual dining. Enjoy your morning coffee or unwind in the evening on the rear deck overlooking nearly half an acre of serene property. Inside, you’ll find gleaming hardwood floors, a dramatic two-story foyer, a grand living room with a cozy fireplace, and a formal dining room ideal f
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Updated Colonial Retreat in Prime West River Location! Welcome to 5235 Chalk Point Road – a beautifully updated 5-bedroom, 3.5-bath Colonial offering 3,052 sq ft of refined living space on a serene 1.37-acre lot. Built in 1990 and thoughtfully enhanced throughout, this spacious home features two primary suites, including one conveniently located on the main floor—perfect for flexible living. Recent upgrades include: Renovated kitchen with modern appliances New flooring throughout Fresh interior paint Updated bathroom vanities Upgraded HVAC system & energy-efficient mini split And much more—too many updates to list! This home effortlessly blends timeless Colonial char
Two story Colonial style home on Steamboat Road. The exterior has a front porch, fenced rear yard and large deck. There is an open floorplan on the first level, 3 bedrooms are located upstairs. This property is located close to the Chesapeake Bay with easy commute to AAFB, DC & Annapolis. Sold in AS IS condition, seller will make no repairs.
Very rare to find an adorable little cottage located on approximately 2 acres. Newer roof, windows & doors. This one has 2 beds, 1 bath, a bright open sunroom thats perfect for a family / living room, a cute little kitchen & dining room. Full size stackable washer/dryer. Newer two zone ductless mini-split. This beauty sits on almost two acres of flat & open land backing to woods. There is a nice new shed as well as part of the rear yard being fenced in. It's one of the largest / flattest lots in Shady Side, so don't miss seeing this amazing location. The home has been well cared for, but being sold AS-IS. No covenants or restrictions, plenty of parking for your boat or RV.