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Waterfront Homes for Sale in Shady Side, MD

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  • /33

    $400,000

    • 4 Beds
    • 1.5 Baths
    • 1,399 Sq Ft

    1199 Oak Ave, Shady Side, MD 20764

    Coastal Comfort, Steps to the Beach - Tucked in the water privileged community of Cedarhurst on the Bay and just a short stroll to the beach and neighborhood amenities, this charming cottage offers relaxed coastal living with a layout full of character. The home features three bedrooms, two with beautiful coffered ceilings that add height and architectural interest. The full bath includes a tub

    Agent Photo

    Bill Franklin

    Long & Foster Real Estate, Inc.

    (410) 835-7611

    1199 Oak Ave, Shady Side, MD 20764
  • /44

    $1,470,000 New Construction

    • 4 Beds
    • 3.5 Baths
    • 3,727 Sq Ft

    5235 Al Jones Dr, Shady Side, MD 20764

    To be built by Whitehall Building & Co., Annapolis’ leading luxury waterfront builder. Set within the sought-after Columbia Beach community, this coastal-style home captures the best of Chesapeake Bay living with panoramic views and the rare protection of a cove-front setting. With Whitehall, the path to building is refreshingly simple. Their step-by-step process begins with a complimentary

    Lynn Peaper Hubble Bisbee Christie's International Real Estate

    5235 Al Jones Dr, Shady Side, MD 20764
  • /31

    $345,000

    • 3 Beds
    • 1 Bath
    • 1,000 Sq Ft

    4738 Washington Ave, Shady Side, MD 20764

    Peaceful Living by the Bay – Perfect for Downsizing! Looking to simplify without sacrificing charm or location? This move-in ready 3-bedroom, 1-bath rancher is the ideal opportunity for anyone craving a slower pace, less maintenance, and more time to enjoy the good life. Tucked on a quiet corner lot next to a protected nature reserve, this single-level home offers peace, privacy, and natural

    Nicole Hatch Samson Properties

    4738 Washington Ave, Shady Side, MD 20764
  • /11

    $149,999

    • Land
    • 0.14 Acre
    • $1,071,421 per Acre

    5250 Al Jones Dr, Shady Side, MD 20764

    LAND LAND in a gated private community! The lot is 3 small lots in total all adjacent to each other. The county has approved building on the lots as ONE dwelling. The home will need to adhere to the building envelope but can be as high as needed (county approved height change)...building a car garage on bottom and build up in SF from there!! A well is needed and there is public septic. I can

    Jennifer Koenig Long & Foster Real Estate, Inc.

    5250 Al Jones Dr, Shady Side, MD 20764
  • /8

    $750,000 Open House 4/12

    • 4 Beds
    • 2.5 Baths
    • 3,679 Sq Ft

    617 Plantation Blvd, West River, MD 20778

    ***Professional Photos coming soon!! *** Shown by Appt only. Welcome to your own private retreat in sought-after West River Estates—where resort-style living meets everyday comfort. With access to a community pier, nearby marina, and surrounded by spectacular wooded views, this exceptional residence offers a seamless blend of indoor and outdoor living designed for both relaxation and

    Nicki Palermo RE/MAX One

    617 Plantation Blvd, West River, MD 20778
  • /31

    $465,000

    • 3 Beds
    • 2.5 Baths
    • 1,664 Sq Ft

    1237A Juniper St, Shady Side, MD 20764

    Welcome home to this beautifully maintained 3-bedroom, 2.5-bath property featuring a bright and open floor plan designed for both comfort and modern living. The spacious living area is filled with natural light and seamlessly flows into the eat-in kitchen and dining space—perfect for entertaining or everyday life. The kitchen is a standout with warm wood flooring, sleek granite countertops,

    Susanne Modica Anne Arundel Properties, Inc.

    1237A Juniper St, Shady Side, MD 20764
  • /52

    $460,000 Open Sat 11AM - 2PM

    • 3 Beds
    • 2 Baths
    • 1,500 Sq Ft

    1168 Maple Ave, Shady Side, MD 20764

    Built in 2019 and set in Cedarhurst on the Bay, this newer Cape Cod offers a South County setting with the layout, finishes, and condition that are hard to find in an established water-oriented community. Inside, the main level features hardwood floors throughout, a first-floor owner’s suite, and a well-finished owner’s bath with a standing shower and double vanity. The kitchen is built for

    Ryan Webster RE/MAX United Real Estate

    1168 Maple Ave, Shady Side, MD 20764
  • /51

    $599,900

    • 3 Beds
    • 2 Baths
    • 1,308 Sq Ft

    4728 Frederick Ave, Shady Side, MD 20764

    Unobstructed, non-riparian waterfront with sweeping panoramic views of the scenic West River. If you’re searching for stunning water views and a home perfectly positioned to capture breathtaking sunsets over the river, this is the one. Inside, you’ll fall in love with the home’s open, contemporary design that maximizes the surrounding views. The upgraded kitchen features granite countertops,

    Ray Mudd Schwartz Realty, Inc.

    4728 Frederick Ave, Shady Side, MD 20764
  • /35

    $1,149,000 Coming Soon

    • 3 Beds
    • 2 Baths
    • 1,964 Sq Ft

    1268 Hayes Rd, Shady Side, MD 20764

    Discover your dream lifestyle at this exceptional waterfront property located at 1268 Hayes Roadd in the charming community of Shady Side, MD. This is a rare chance to own a piece of serene waterfront living, offering unparalleled access to the bay and all the tranquility the area affords. The property features 3 ample sized bedrooms and 2 updated bathrooms combining the peacefulness of a

    Casey A Sutherland Maryland Waterfront Properties LLC

    1268 Hayes Rd, Shady Side, MD 20764
  • /35

    $729,900

    • 3 Beds
    • 2 Baths
    • 1,866 Sq Ft

    1650 Cedar Ln, Shady Side, MD 20764

    Experience Unmatched Privacy and Tranquility from this unique non-riparian waterfront home set on over 3+ scenic acres. Fall in love with sweeping water views and the serene presence of native wildlife—waterfowl, deer, eagles, and more—all just outside your door. Enjoy panoramic vistas of a natural pond, with the stunning Chesapeake Bay visible in the distance. On clear days, the Bay Bridge is

    Ray Mudd Schwartz Realty, Inc.

    1650 Cedar Ln, Shady Side, MD 20764
  • /2

    $429,000 Coming Soon

    • 3 Beds
    • 2.5 Baths
    • 1,500 Sq Ft

    1205 Avalon Blvd, Shady Side, MD 20764

    Professional photos coming soon!

    Nicki Palermo RE/MAX One

    1205 Avalon Blvd, Shady Side, MD 20764
  • /32

    $499,900

    • 4 Beds
    • 2.5 Baths
    • 1,890 Sq Ft

    1006 Henry Ave, West River, MD 20778

    The original owner has carefully maintained this home over the years. The main level features a welcoming living room with a gas fireplace, LVP floors, a bright and sunny study/office, and a spacious kitchen with granite countertops, backsplash, and a dining area highlighted by a beautiful picture window overlooking the fenced rear yard. Newer windows are installed throughout the home by Anderson

    Ray Mudd Schwartz Realty, Inc.

    1006 Henry Ave, West River, MD 20778
  • /40

    $889,900 Open Sun 12PM - 2PM

    • 4 Beds
    • 3 Baths
    • 2,496 Sq Ft

    819 Elm Dr, West River, MD 20778

    Waterfront opportunity along the West River, located in the Shady Oaks Manor community. Dock your boat at the private pier just off the large, flat lot and enjoy direct access to the water. From here, it is an easy ride out to the Chesapeake Bay and nearby waterfront towns. Inside, the home offers four bedrooms and three full bathrooms, including a primary bedroom with its own attached bath. The

    Erica Baker TTR Sotheby's International Realty

    819 Elm Dr, West River, MD 20778

Home Trends in Shady Side, MD

Housing Trends

Median Sale Price
$409,950
Median Single Family Sale Price
$424,500
Average Price Per Sq Ft
$314
Number of Homes for Sale
21
Last 12 months Home Sales
88
Months of Supply
2.90
Median List Price
$439,000
Median Change From 1st List Price
0%
Median Home Sale Price YoY Change
3%
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