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Shady Side Homes for Sale

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  • /73

    $750,000 Open Sun 3PM - 5PM

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

    617 Plantation Blvd, West River, MD 20778

    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 entertaining. Step inside to a grand two-story foyer,

    Nicki Palermo RE/MAX One

    617 Plantation Blvd, West River, MD 20778
  • /2

    $499,990 Coming Soon

    • 3 Beds
    • 2.5 Baths
    • 1,598 Sq Ft

    1222 Juniper St, Shady Side, MD 20764

    Would you love to live in a water oriented community? Have you ever? Come take a look at this year 2020 constructed 3 bedroom 2.5 bathroom home located in the AVALON SHORES community surrounded by the beautiful Chesapeake Bay and tributaries. Avalon Shores has wonderful neighborhood amenities including play areas, beach and boat launch . Come see this traditional home with an open floor plan.

    Jesse Hoffman HomeSmart

    1222 Juniper St, Shady Side, MD 20764
  • /61

    $659,990 New Construction

    • 4 Beds
    • 2.5 Baths
    • 2,710 Sq Ft

    5314 Al Jones Dr, Shady Side, MD 20764

    4/6/26. Just broke ground. Late summer delivery. Coastal Living Just Steps from the Chesapeake Bay! Schaefer Homes invites you to make this beautifully designed coastal-style residence your own located across the street from the bay offering nice water views. Offering over 3 stories of wide open living with time to personalize your selections so you can create a home that perfectly reflects your

    Ray Mudd Schwartz Realty, Inc.

    5314 Al Jones Dr, Shady Side, MD 20764
  • /19

    $389,000

    • 3 Beds
    • 2 Baths
    • 1,040 Sq Ft

    1469 Cedarhurst Rd, Shady Side, MD 20764

    Enjoy privacy and space in this charming ranch-style home set on a beautiful 3.75-acre wooded lot. A welcoming stone walkway leads you to the front door. Inside, the home features a spacious living room that flows seamlessly into the kitchen, offering plenty of room for a dining table. The primary bedroom includes an en-suite bathroom with a shower, while two additional bedrooms share a full

    Amelia Whitman Long & Foster Real Estate, Inc.

    1469 Cedarhurst Rd, Shady Side, MD 20764
  • /82

    $799,500 Open Sat 11:30AM - 2PM

    • 3 Beds
    • 3 Baths
    • 2,200 Sq Ft

    5229 Al Jones Dr, Shady Side, MD 20764

    Truly special and exceptionally improved bayfront offering in the gated Columbia Beach community of Shady Side. This Classic Cape Cod is all about the experience and attention to detail—breathtaking Chesapeake Bay vistas, unforgettable sunrises and sunsets, and the kind of big-sky waterfront setting that makes this home feel like a retreat every single day. Seller has maintained detailed

    Greg Fisk Douglas Realty, LLC

    5229 Al Jones Dr, Shady Side, MD 20764
  • /20

    $439,900

    • 3 Beds
    • 1.5 Baths
    • 1,320 Sq Ft

    1160 Oak Ave, Shady Side, MD 20764

    Experience the epitome of luxury living in this stunning Colonial home, beautifully renovated in 2026. Nestled in the exclusive Cedar Hurst on the Bay community, this residence offers a harmonious blend of elegance and comfort. With three spacious bedrooms and 1.5 baths, the layout is perfect for both relaxation and entertaining. Step outside to discover enchanting water features that create a

    Agent Photo

    Andy Schweigman

    Douglas Realty, LLC

    (410) 862-0515

    1160 Oak 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 in this exceptional 3 bedroom 2 full bath waterfront property located at 1268 Hayes Road in the charming community of Shady Side, MD. combining the peacefulness of a secluded setting with essential modern amenities. As you step inside you'll notice the sun drenched open floor plan complete with a large cooks kitchen featuring a huge center island, cozy breakfast nook

    Casey A Sutherland Maryland Waterfront Properties LLC

    1268 Hayes Rd, Shady Side, MD 20764
  • /36

    $649,990 New Construction

    • 4 Beds
    • 2.5 Baths
    • 2,710 Sq Ft

    1235 Spruce Ave, Shady Side, MD 20764

    THIS IS A TO BE BUILT HOME. Act soon while you are able to still personalize this home with interior selections!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 crafted home features classic board-and-batten siding and a welcoming front porch that creates timeless curb appeal.

    Agent Photo

    Jamie Richardson

    RE/MAX United Real Estate

    (443) 363-1364

    1235 Spruce Ave, Shady Side, MD 20764
  • /2

    $25,000

    • Land
    • 0.11 Acre
    • $227,273 per Acre

    1205 Poplar Ave, Shady Side, MD 20764

    ONLINE AUCTION: This auction takes place on the Ashland Auction Group Website Bidding Platform. Bidding begins 4/10/2026 @ 10:00 AM. Bidding ends 4/14/2026 @ 11:40 AM. List Price is Suggested Opening Bid. Deposit: $5,000. This +/- 4,750 ft2 parcel of land is located in Shady Side, MD within Anne Arundel County. It is just minutes away to Herring Bay and offers easy access to major traffic

    Adam Shpritz Ashland Auction Group LLC

    1205 Poplar Ave, Shady Side, MD 20764
  • /14

    $235,000

    • 2 Beds
    • 1 Bath
    • 736 Sq Ft

    1502 Garst Rd, Shady Side, MD 20764

    Investor special in the charming Columbia Beach community of Shadyside. This quaint 2-bedroom, 1-bath home offers great potential for investors, renovators, or buyers looking to create their own coastal retreat. Inside, you'll find classic panel walls, a cozy fireplace, and a bright sunroom that adds extra living space and character. Nestled in a peaceful setting near the water, this property is

    Victoria Carmon-Brown Fusion Elite Realty

    1502 Garst Rd, Shady Side, MD 20764
  • /31

    $449,804

    • 3 Beds
    • 2 Baths
    • 1,456 Sq Ft

    5635 W Shady Side Rd, Shady Side, MD 20733

    Welcome home to this beautifully updated rambler in the heart of Churchton! This 3-bedroom, 2 full bath house has been thoughtfully modernized, featuring a traditional floor plan with stunning hardwood floors and fresh updates throughout. Brand new kitchen with upgraded cabinetry, elegant backsplash, and modern quartz countertops. Enjoy cozy evenings by the brick fireplace with a wood stove

    Iftikhar Khan RE/MAX Galaxy

    5635 W Shady Side Rd, Shady Side, MD 20733
  • /37

    $575,000

    • 4 Beds
    • 3 Baths
    • 1,905 Sq Ft

    1411 Haile Pkwy, Shady Side, MD 20764

    This thoughtfully designed and 2022-built home blends modern finishes with a tranquil setting set against a backdrop of mature woods, creating a bright, open, and inviting space for both everyday living and entertaining. An open two-story foyer welcomes you inside to the main living area with vaulted ceilings, while 9' ceilings throughout the rest of the home enhance the airy, open feel. Charming

    Mary Gatton Redfin Corp

    1411 Haile Pkwy, Shady Side, MD 20764
  • /2

    $79,999

    • Land
    • 1.04 Acres
    • $76,922 per Acre

    5280 Cedar St, West River, MD 20778

    Beautiful 1.04-acre wooded lot offering privacy and a peaceful natural setting. The property provides a wonderful opportunity to build your dream home surrounded by trees while still being conveniently located near local amenities, restaurants, shopping, and commuter routes.

    Melissa Chick Engel & Völkers Annapolis

    5280 Cedar St, West River, MD 20778
  • /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
  • /32

    $579,990 New Construction

    • 4 Beds
    • 2.5 Baths
    • 2,091 Sq Ft

    1225 Juniper St, Shady Side, MD 20764

    THIS IS A TO BE BUILT HOME

    Agent Photo

    Jamie Richardson

    RE/MAX United Real Estate

    (410) 724-1190

    1225 Juniper St, Shady Side, MD 20764
  • /37

    $599,990 New Construction

    • 4 Beds
    • 2.5 Baths
    • 2,068 Sq Ft

    1209 Johnson Dr, Shady Side, MD 20764

    HOME TO BE BUILT. EXPECTED LATE SUMMER 2026 DELIVERY. Schaefer Homes brings to you their latest Monroe model located in water privilege community offering community beach, pier, boat ramp, playground, slips, and more. Select from 3 exterior elevations! This home will come standard with plenty of upgraded features, and there is still the opportunity to make your personal selections to suit your

    Ray Mudd Schwartz Realty, Inc.

    1209 Johnson Dr, Shady Side, MD 20764
  • /23

    $750,000

    • 4 Beds
    • 1.5 Baths
    • 2,144 Sq Ft

    1462 Snug Harbor Rd, Shady Side, MD 20764

    4 Bedrooms/ 1 full bath and 1 half bath with shower. 2144 SQ Ft home and income opportunity goes with this home on .57 acres of C1B commercial zoned property. Additional .375 acres and .1243 acres of Ma2 zoned property for a totaling 1.0693 Acres, with 135 feet of bulkheaded waterfront, 200-foot pier, with approximately 12 boat slips. Water depth from 4 to 8 feet that can accommodate 40ft+ boats.

    George Heine Schwartz Realty, Inc.

    1462 Snug Harbor Rd, Shady Side, MD 20764
  • /30

    $469,000

    • 3 Beds
    • 2.5 Baths
    • 2,235 Sq Ft

    1161 Steamboat Rd, Shady Side, MD 20764

    Welcome to this inviting single-family home in the heart of Shady Side! This lovely residence features 3 bedrooms, 2.5 bathrooms, and approximately 2,235 sq ft of versatile living space — thoughtfully laid out to balance comfort and function.Step inside to a warm, open floor plan where natural light enhances every room, and an efficient layout makes everyday living easy. A well-appointed

    Christine Saunders Compass

    1161 Steamboat Rd, Shady Side, MD 20764
  • /28

    $529,650

    • 3 Beds
    • 2 Baths
    • 2,024 Sq Ft

    4949 Idlewilde Rd, Shady Side, MD 20764

    This spacious and well-maintained home offers the ease of one-level living at it's best. The modern kitchen opens to a cozy family room with sliding door leading to a stunning sunroom and adjacent deck—perfect for relaxing or entertaining. Enjoy formal spaces with both a living room and dining room, along with a generous primary suite complete with a private full bath. Two additional bedrooms and

    Ray Mudd Schwartz Realty, Inc.

    4949 Idlewilde Rd, Shady Side, MD 20764
  • /43

    $599,990 New Construction

    • 4 Beds
    • 2.5 Baths
    • 2,091 Sq Ft

    4908 Olive St, Shady Side, MD 20764

    4/3/26 Foundation started. EXPECTED SUMMER 2026 DELIVERY. Must use builder contract - buyer responsible for 100% transfer taxes**. Schaefer Homes brings to you their latest Monroe model located in water privilege community of Westelee offering community beach, pier, playground, boat slips, boat ramp and more. Select from 3 exterior elevations! This home will come standard with plenty of upgraded

    Ray Mudd Schwartz Realty, Inc.

    4908 Olive St, Shady Side, MD 20764
  • /2

    $40,000

    • Land
    • 0.34 Acre
    • $117,647 per Acre

    5771 Shady Side Rd, Churchton, MD 20733

    Residential building lot awaits new owner. Sold as is .

    Joseph Butcher Long & Foster Real Estate, Inc.

    5771 Shady Side Rd, Churchton, MD 20733
  • /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
  • /4

    $50,000

    • Land
    • 0.17 Acre
    • $294,118 per Acre

    4907 Quince St, Shady Side, MD 20764

    Per the recorded Conservation Easement. No primary residence shall be constructed

    Ray Mudd Schwartz Realty, Inc.

    4907 Quince St, 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
  • /15

    $270,750

    • 3 Beds
    • 1 Bath
    • 1,022 Sq Ft

    1419 Shady Rest Rd, Shady Side, MD 20764

    SHORT SALE APPROVED AT LIST PRICE! This charming three-bedroom, one-bathroom house presents an exceptional investor opportunity in peaceful Shady Side. The property offers excellent renovation potential, allowing you to customize and add value while creating possible rental income streams. Enjoy convenient parking and generous outdoor space perfect for relaxation or entertainment. The spacious

    Cindy Martin Samson Properties

    1419 Shady Rest Rd, Shady Side, MD 20764
  • /5

    $150,000

    • Land
    • 4.03 Acres
    • $37,221 per Acre

    0 Shady Side Rd Unit MDAA2113156, Shady Side, MD 20764

    This beautiful four acre lot is heavily wooded, flat and level. Approximately 1,000' off the main road makes it very private and secluded. It abuts an additional four acre lot also available for sale. It is believed that because some of the property is in non-tidal wetlands that it cannot be subdivided but buyers should investigate with a civil engineer of choice to confirm. The access

    Sam Tanner Keller Williams Flagship

    0 Shady Side Rd Unit MDAA2113156, Shady Side, MD 20764
  • /2

    $150,000

    • Land
    • 4.03 Acres
    • $37,221 per Acre

    0 Shady Side Rd Unit MDAA2113166, Shady Side, MD 20764

    This beautiful four acre lot is heavily wooded, flat and level. Approximately 1,000' off the main road makes it very private and secluded. It abuts an additional four acre lot also available for sale. It is believed that because some of the property is in non-tidal wetlands that it cannot be subdivided but buyers should investigate with a civil engineer of choice to confirm. The access

    Sam Tanner Keller Williams Flagship

    0 Shady Side Rd Unit MDAA2113166, 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
  • /6

    $249,999

    • Land
    • 0.77 Acre
    • $324,674 per Acre

    4846 Woods Wharf Rd, Shady Side, MD 20764

    Vacant Lot Ideal for Expansion or New Venture. Perfect for Boat Storage or New Building. Leverage its proximity to high-demand recreational areas for profitable boat and trailer storage, or business vehicles, or develop the lot into a commercial building for your business, or to lease the space to a business who is looking to serve the local community.

    Scott Cleary RE/MAX One

    4846 Woods Wharf Rd, Shady Side, MD 20764

Frequently Asked Questions Why Live in Shady Side

Is Shady Side a good place to live?
Shady Side is a good place to live. Shady Side is considered very car-dependent and somewhat bikeable. Shady Side is a neighborhood with a crime score of 1, making it safer than the average neighborhood in the U.S. Shady Side has 1 park for recreational activities. It has a median age of 44. The average household income is $143,434 which is above the national average. College graduates make up 35.2% of residents. A majority of residents in Shady Side are home owners, with 11.9% of residents renting and 88.1% of residents owning their home. A local real estate agent serving Shady Side can help you decide if this neighborhood is the right one for you. Learn more on our Shady Side neighborhood guide.
Is Shady Side, MD a safe neighborhood?
Shady Side, MD is safer than the average neighborhood in the United States. It received a crime score of 1 out of 10.
How much do you need to make to afford a house in Shady Side?
The median home price in Shady Side is $450,000. If you put a 20% down payment of $90,000 and had a 30-year fixed mortgage with an interest rate of 6.46%, your estimated principal and interest payment would be $2,270 a month plus property taxes, HOA fees, home insurance, PMI, and utilities. Using the 28% rule, you would need to make at least $97K a year to afford the median home price in Shady Side. Learn how much home you can afford with our Home Affordability Calculator. The average household income in Shady Side is $143K.
What are the best public schools in Shady Side?
The best public schools that serve Shady Side are:
What are the most popular zip codes in Shady Side, Shady Side, MD?
The most popular zip codes in Shady Side, Shady Side, MD include 20764, 20733, 20778, 20776 and 20751.
What are the most popular neighborhoods near Shady Side, Shady Side, MD?
The most popular neighborhoods near Shady Side, Shady Side, MD are Harwood, Selby-on-the-Bay, Davidsonville, Victor Haven and Tyler Heights-Primrose Acres.

Home Trends in Shady Side, MD

Housing Trends

Median Sale Price
$449,900
Median Single Family Sale Price
$450,000
Average Price Per Sq Ft
$304
Number of Homes for Sale
20
Last 12 months Home Sales
111
Months of Supply
2.20
Median List Price
$450,000
Median Change From 1st List Price
0%
Median Home Sale Price YoY Change
7%
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