53

Shady Side, MD Homes for Sale

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  • 1225 Juniper St, Shady Side, MD 20764
    1225 Juniper St, Shady Side, MD 20764
    1225 Juniper St, Shady Side, MD 20764
    /32

    $589,990

    New Construction $10K PRICE INCREASE
    • 4 Beds
    • 2.5 Baths
    • 2,091 Sq Ft

    1225 Juniper St, Shady Side, MD 20764

    AUGUST DELIVERY! 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. Inside, the open-concept layout seamlessly connects the dining area and family room, making it

    Agent Photo

    Jamie Richardson

    RE/MAX United Real Estate

    1225 Juniper St, Shady Side, MD 20764
  • 1237 Spruce Ave, Shady Side, MD 20764
    1237 Spruce Ave, Shady Side, MD 20764
    1237 Spruce Ave, Shady Side, MD 20764
    /55

    $619,990

    New Construction
    • 4 Beds
    • 2.5 Baths

    1237 Spruce Ave, Shady Side, MD 20764

    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. Inside, the open-concept layout seamlessly connects the dining area and family room, making it perfect for everyday

    Agent Photo

    Jamie Richardson

    RE/MAX United Real Estate

    1237 Spruce Ave, Shady Side, MD 20764
  • 1003 Henry Ave, West River, MD 20778
    1003 Henry Ave, West River, MD 20778
    1003 Henry Ave, West River, MD 20778
    /22

    $599,990

    New Construction
    • 4 Beds
    • 2.5 Baths
    • 1,946 Sq Ft

    1003 Henry Ave, West River, MD 20778

    Located in the charming Back Bay Beach area of West River, 1003 Henry Avenue offers the relaxed feel of Southern Anne Arundel County living with easy access to the water, marinas, local dining, and nearby historic Galesville. Enjoy the laid-back coastal lifestyle of the West River, with Galesville Wharf, waterfront restaurants, boating access, and scenic outdoor destinations just minutes away.

    Agent Photo

    Jamie Richardson

    RE/MAX United Real Estate

    1003 Henry Ave, West River, MD 20778
  • 1235 Spruce Ave, Shady Side, MD 20764
    1235 Spruce Ave, Shady Side, MD 20764
    1235 Spruce Ave, Shady Side, MD 20764
    /55

    $650,990

    New Construction $1K PRICE INCREASE
    • 4 Beds
    • 2.5 Baths
    • 2,710 Sq Ft

    1235 Spruce Ave, Shady Side, MD 20764

    AUGUST Delivier!!!!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. Inside, the open-concept layout seamlessly connects the dining area and family room, making

    Agent Photo

    Jamie Richardson

    RE/MAX United Real Estate

    1235 Spruce Ave, Shady Side, MD 20764
  • 4921 Olive St, Shady Side, MD 20764
    4921 Olive St, Shady Side, MD 20764
    4921 Olive St, Shady Side, MD 20764
    /32

    $405,000

    $15K PRICE DROP
    • 3 Beds
    • 1 Bath
    • 1,008 Sq Ft

    4921 Olive St, Shady Side, MD 20764

    *** HUGE PRICE IMPROVEMENT! SUNDAY, JULY 19, OPEN HOUSE, 12-2PM! ***Coastal charm meets modern comfort in Avalon Shores! This sun-drenched, corner-lot 1940s cottage boasts beautiful water views from both floors. The inviting interior features a spacious kitchen with stainless steel appliances, while wrap-around windows flood the entire main living area with bright, natural light. Relax or

    Eric Hovanky Redfin Corp

    4921 Olive St, Shady Side, MD 20764
  • 1411 Haile Pkwy, Shady Side, MD 20764
    1411 Haile Pkwy, Shady Side, MD 20764
    1411 Haile Pkwy, Shady Side, MD 20764
    /37

    $538,000

    $37K PRICE DROP
    • 4 Beds
    • 3 Baths
    • 1,905 Sq Ft

    1411 Haile Pkwy, Shady Side, MD 20764

    Price reduction! 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,

    Mary Gatton Redfin Corp

    1411 Haile Pkwy, Shady Side, MD 20764
  • 5341 Al Jones Dr, Shady Side, MD 20764
    5341 Al Jones Dr, Shady Side, MD 20764
    5341 Al Jones Dr, Shady Side, MD 20764
    /48

    $745,000

    • 3 Beds
    • 2 Baths
    • 1,962 Sq Ft

    5341 Al Jones Dr, Shady Side, MD 20764

    Fantastic opportunity to own your own land lighthouse-inspired round house with water views! Perfect serene retreat for the commuter and/or investment opportunity. Quiet neighborhood, blue heron sightings, and all the advantages of coastal living without the summer beach traffic. Freshly painted! This unique home features 3 bedrooms, 2 full bathrooms, an open-concept layout, and a spacious family

    Melissa Wilson Redfin Corp

    5341 Al Jones Dr, Shady Side, MD 20764
  • 1527 Lincoln Rd, Shady Side, MD 20764
    1527 Lincoln Rd, Shady Side, MD 20764
    1527 Lincoln Rd, Shady Side, MD 20764
    /30

    $410,000

    $15K PRICE DROP
    • 3 Beds
    • 2.5 Baths
    • 1,200 Sq Ft

    1527 Lincoln Rd, Shady Side, MD 20764

    Experience the best of the Chesapeake Bay in this 3-bedroom, 2.5-bathroom Colonial, in the sought-after Columbia Beach neighborhood! Nestled in a quiet, gated, water-privileged community, this home offers more than just a place to live—it offers a lifestyle complete with a private pier, boat ramp, tennis/basketball courts, and a playground. The heart of the home is the beautifully curated

    Mike Benton Home Towne Real Estate

    1527 Lincoln Rd, Shady Side, MD 20764
  • 1183 Cedar Ave, Shady Side, MD 20764
    1183 Cedar Ave, Shady Side, MD 20764
    1183 Cedar Ave, Shady Side, MD 20764
    /33

    $535,000

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

    1183 Cedar Ave, Shady Side, MD 20764

    Professional pictures coming!! Rarely available and proudly offered for the first time, this spacious split-foyer home is nestled on nearly a quarter-acre lot in the highly desirable water-privileged community of Cedarhurst. Lovingly maintained by its original owner, this well cared for residence offers 4 bedrooms, 3 full bathrooms, and multiple living spaces designed for both comfort and

    John Tarpley Schwartz Realty, Inc.

    1183 Cedar Ave, Shady Side, MD 20764
  • 4846 Woods Wharf Rd, Shady Side, MD 20764
    4846 Woods Wharf Rd, Shady Side, MD 20764
    4846 Woods Wharf Rd, Shady Side, MD 20764
    /6

    $249,999

    • Land
    • 33,541 Sq Ft
    • $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
  • 4909 Olive St, Shady Side, MD 20764
    4909 Olive St, Shady Side, MD 20764
    4909 Olive St, Shady Side, MD 20764
    /40

    $490,000

    $10K PRICE DROP
    • 3 Beds
    • 2.5 Baths
    • 1,848 Sq Ft

    4909 Olive St, Shady Side, MD 20764

    Welcome to 4909 Olive Street, a newer construction three bedroom, two and a half bath home in the waterfront community of Avalon Shores. Offering a functional layout, contemporary finishes, open living spaces, a fully fenced in backyard, and a private driveway. Avalon Shores residents enjoy access to a community beach, fishing pier, boat ramp, kayak launch, waterfront park, playground, basketball

    Erica Baker TTR Sotheby's International Realty

    4909 Olive St, Shady Side, MD 20764
  • 1316 Juniper St, Shady Side, MD 20764
    1316 Juniper St, Shady Side, MD 20764
    1316 Juniper St, Shady Side, MD 20764
    /41

    $549,900

    New Construction $20K PRICE DROP
    • 4 Beds
    • 2.5 Baths
    • 1,949 Sq Ft

    1316 Juniper St, Shady Side, MD 20764

    This Stylish New home is move in ready and just in time to enjoy the summer breezes at the community Beach areas and play grounds! It is ready for your personal touch to make it your own! Main level features include Luxury Vinyl Plank flooring, 9' ceilings, Luxury kitchen with granite countertops, stainless steel appliances accented with sleek white cabinets with soft close drawers and a center

    Paul Lee Long & Foster Real Estate, Inc.

    1316 Juniper St, Shady Side, MD 20764
  • 4950 Bonniewood Dr, Shady Side, MD 20764
    4950 Bonniewood Dr, Shady Side, MD 20764
    4950 Bonniewood Dr, Shady Side, MD 20764
    /73

    $795,000

    • 3 Beds
    • 2 Baths
    • 2,304 Sq Ft

    4950 Bonniewood Dr, Shady Side, MD 20764

    Waterfront living with a private dock—all for under $800,000! Nestled in the charming Avalon Shores community, this beautifully updated coastal home perfectly blends classic elegance with modern comfort. The open-concept layout features two distinct living areas, ideal for both entertaining and daily relaxation. At the heart of the home is a premium kitchen equipped with granite countertops,

    Jamie Angichiodo RE/MAX Leading Edge

    4950 Bonniewood Dr, Shady Side, MD 20764
  • 5209 Al Jones Dr, Shady Side, MD 20764
    5209 Al Jones Dr, Shady Side, MD 20764
    5209 Al Jones Dr, Shady Side, MD 20764
    /25

    $149,900

    • Land
    • 4,356 Sq Ft
    • $1,499,000 per Acre

    5209 Al Jones Dr, Shady Side, MD 20764

    WATERFRONT OPPORTUNITY!! Discover the perfect setting to build your dream home or weekend retreat on this waterfront lot offering breathtaking views of the Chesapeake Bay. Nestled in the quiet, secluded community of Columbia Beach, this approximately 4,450-square-foot homesite is already serviced by public sewer, making it an exceptional opportunity to bring your vision to life. Wake up to

    Mark Frisco CENTURY 21 New Millennium

    5209 Al Jones Dr, Shady Side, MD 20764
  • 4721 Oak Rd, Shady Side, MD 20764
    4721 Oak Rd, Shady Side, MD 20764
    4721 Oak Rd, Shady Side, MD 20764
    /57

    $1,110,000

    $50K PRICE DROP
    • 4 Beds
    • 3 Baths
    • 1,868 Sq Ft

    4721 Oak Rd, Shady Side, MD 20764

    Welcome to 4721 Oak Road, your waterfront paradise on the Chesapeake Bay! Nestled in the sought-after Felicity Cove community of Shady Side, this custom-built 2014 coastal home seamlessly blends modern luxury with effortless waterfront living. Boasting 4 spacious bedrooms, 3 full bathrooms, and 1,868 square feet of pristine living space, this residence shows like new. Step inside to an

    Angie Carr Riverscape Realty

    4721 Oak Rd, Shady Side, MD 20764
  • 6372 Shady Side Rd, Shady Side, MD 20764
    6372 Shady Side Rd, Shady Side, MD 20764
    6372 Shady Side Rd, Shady Side, MD 20764
    /34

    $380,000

    • 3 Beds
    • 3 Baths
    • 2,450 Sq Ft

    6372 Shady Side Rd, Shady Side, MD 20764

    Opportunity awaits at this charming farmhouse nestled in the waterfront community of Shady Side. Situated on a spacious lot, this home offers a peaceful setting with convenient access to local marinas, parks, dining, and commuter routes. The interior presents a functional layout with generous living spaces, abundant natural light, and endless potential for customization. Enjoy the privacy of the

    Brenda Sarver Maryland Realty Connection

    6372 Shady Side Rd, Shady Side, MD 20764
  • 5250 Al Jones Dr, Shady Side, MD 20764
    5250 Al Jones Dr, Shady Side, MD 20764
    5250 Al Jones Dr, Shady Side, MD 20764
    /11

    $95,000

    • Land
    • 6,098 Sq Ft
    • $678,571 per Acre

    5250 Al Jones Dr, Shady Side, MD 20764

    **REDUCED** 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. County allowed neighbor to put well on this parcel by mistake many years ago. The county will allow for setback forgiveness for their mistake. Back corner @ 10ft is where the well for neighbor is. So it percs! Sold As Is.

    Jennifer Koenig Long & Foster Real Estate, Inc.

    5250 Al Jones Dr, Shady Side, MD 20764
  • 4734 Oak Rd, Shady Side, MD 20764
    4734 Oak Rd, Shady Side, MD 20764
    4734 Oak Rd, Shady Side, MD 20764
    /49

    $625,000

    • 4 Beds
    • 2.5 Baths
    • 2,511 Sq Ft

    4734 Oak Rd, Shady Side, MD 20764

    Enjoy breathtaking views of the Chesapeake Bay from this charming home in the quaint waterfront community of Felicity Cove. The ground level features two bedrooms (one without a closet), a full bathroom, and a second kitchen, making it an ideal space for guests, extended family, or multi-generational living. The main living area is located on the second floor to take full advantage of the

    Ray Mudd Schwartz Realty, Inc.

    4734 Oak Rd, Shady Side, MD 20764
  • 4907 Quince St, Shady Side, MD 20764
    4907 Quince St, Shady Side, MD 20764
    4907 Quince St, Shady Side, MD 20764
    /4

    $50,000

    • Land
    • 7,405 Sq Ft
    • $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
  • 1436 Haile Pkwy, Shady Side, MD 20764
    1436 Haile Pkwy, Shady Side, MD 20764
    /2

    $100,000

    • Land
    • 1 Acre
    • $100,000 per Acre

    1436 Haile Pkwy, Shady Side, MD 20764

    Sub-division potential for this undeveloped, 1 acre lot! May be able to reconfigure to 2 separate lots. Discover the perfect retreat from city life in the serene setting of Shady Side, MD. This parcel of land offers a rare opportunity to build your dream home amidst nature’s beauty. Tucked away in a peaceful community, the property provides the ideal balance of tranquility and accessibility. With

    Joan Stansfield Samson Properties

    1436 Haile Pkwy, Shady Side, MD 20764
  • 4912 Mariners Dr, Shady Side, MD 20764
    4912 Mariners Dr, Shady Side, MD 20764
    4912 Mariners Dr, Shady Side, MD 20764
    /42

    $389,900

    $40K PRICE DROP
    • 3 Beds
    • 1.5 Baths
    • 1,386 Sq Ft

    4912 Mariners Dr, Shady Side, MD 20764

    Coastal Affordable Living with a Boat Slip Included Discover the charm of Snug Harbor, where coastal living meets everyday affordability. This beautifully updated home offers gorgeous Chesapeake Bay views and the rare bonus of an included boat slip — making waterfront living more accessible than ever. Inside offers a light-filled floorplan, wide open living room, an open kitchen shines with

    Sam Barbieri RE/MAX United Real Estate

    4912 Mariners Dr, Shady Side, MD 20764
  • 0 Pine Ave Unit MDAA2139458, Shady Side, MD 20764
    0 Pine Ave Unit MDAA2139458, Shady Side, MD 20764
    /2

    $25,000

    • Land
    • 4,791 Sq Ft
    • $227,273 per Acre

    0 Pine Ave Unit MDAA2139458, Shady Side, MD 20764

    ONLINE AUCTION: This auction takes place on the Ashland Auction Group website bidding platform. Bidding begins 7/24/2026, 10:00 AM. Bidding ends 7/28/2026, 12:40 PM. The list price is suggested opening bid. Deposit: $5,000. This +/- 4,750 ft2 parcel of land is located in located in Shady Side, MD within Anne Arundel County. Its location is just a few minutes away to Herring Bay. It also offers

    Adam Shpritz Ashland Auction Group LLC

    0 Pine Ave Unit MDAA2139458, Shady Side, MD 20764
  • 4750 Frederick Ave, Shady Side, MD 20764
    4750 Frederick Ave, Shady Side, MD 20764
    4750 Frederick Ave, Shady Side, MD 20764
    /76

    $3,500,000

    • 5 Beds
    • 5.5 Baths
    • 4,620 Sq Ft

    4750 Frederick Ave, Shady Side, MD 20764

    Silver Water is a rare west-facing waterfront home designed in direct response to the Chesapeake—offering broad water views, remarkable sunsets, and a level of architectural clarity seldom found in the area. Set behind a private gate on a beautifully landscaped one-acre lot along the West River, the property combines seclusion with convenient access to Annapolis and Washington, DC. Spanning over

    David Orso Berkshire Hathaway HomeServices PenFed Realty

    4750 Frederick Ave, Shady Side, MD 20764
  • 0 Haile Pkwy Unit MDAA2141624, Shady Side, MD 20764
    0 Haile Pkwy Unit MDAA2141624, Shady Side, MD 20764
    /2

    $25,000

    • Land
    • 24,829 Sq Ft
    • $43,860 per Acre

    0 Haile Pkwy Unit MDAA2141624, Shady Side, MD 20764

    No address assigned for Lots 6 & 7. Discover the perfect retreat from city life in the serene setting of Shady Side, MD. This parcel of land offers a rare opportunity to build your dream home amidst nature’s beauty. Tucked away in a peaceful community, the property provides the ideal balance of tranquility and accessibility. With convenient access to Route 2, commuting to Annapolis, Baltimore, or

    Joan Stansfield Samson Properties

    0 Haile Pkwy Unit MDAA2141624, Shady Side, MD 20764
  • 4915 E Chalk Point Rd, West River, MD 20778
    4915 E Chalk Point Rd, West River, MD 20778
    /2

    $1,400,000

    Coming Soon
    • 3 Beds
    • 2 Baths
    • 1,582 Sq Ft

    4915 E Chalk Point Rd, West River, MD 20778

    Opportunity to make your own on highly desirable E. Chalk Point Road overlooking South Creek and West River. Charming bungalow with Kitchen, living room with fireplace, wrap around 4 season porch, and 2 bedrooms, 2 baths on main level. Upstairs is additional bonus room and space to expand. Detached 2 car garage with apartment w/ full bath above. Bungalow, and pier with lifts complete the property.

    Doc Keane Washington Fine Properties, LLC

    4915 E Chalk Point Rd, West River, MD 20778
  • 5331 Sweetwater Dr, West River, MD 20778
    5331 Sweetwater Dr, West River, MD 20778
    5331 Sweetwater Dr, West River, MD 20778
    /61

    $800,000

    Open Sat 11AM - 1PM $50K PRICE DROP
    • 5 Beds
    • 3.5 Baths
    • 4,204 Sq Ft

    5331 Sweetwater Dr, West River, MD 20778

    Stately brick-front Colonial located in the highly sought-after water-privileged community of West River Estates. This absolutely gorgeous home offers exceptional space, charm, and amenities throughout. The beautifully appointed kitchen features granite countertops, double wall ovens, a large center island with built-in cooktop, and ample cabinetry. French doors open to a bright all-season

    Ray Mudd Schwartz Realty, Inc.

    5331 Sweetwater Dr, West River, MD 20778
  • 1500 Garst Rd, Shady Side, MD 20764
    1500 Garst Rd, Shady Side, MD 20764
    1500 Garst Rd, Shady Side, MD 20764
    /24

    $364,000

    $12K PRICE INCREASE
    • 2 Beds
    • 1.5 Baths
    • 1,144 Sq Ft

    1500 Garst Rd, Shady Side, MD 20764

    Enjoy water views and the best of coastal living in this charming home, ideally located in a private waterfront community with exclusive access to a boat ramp and sandy beach. The open-concept living and kitchen area creates an inviting space for everyday living and entertaining, while the large fenced backyard offers plenty of room for pets, play, and outdoor gatherings. A rare opportunity to

    Maggie Richards Berkshire Hathaway HomeServices PenFed Realty

    1500 Garst Rd, Shady Side, MD 20764
  • 4738 Washington Ave, Shady Side, MD 20764
    4738 Washington Ave, Shady Side, MD 20764
    4738 Washington Ave, Shady Side, MD 20764
    /27

    $349,900

    $50K PRICE DROP
    • 3 Beds
    • 2 Baths
    • 1,223 Sq Ft

    4738 Washington Ave, Shady Side, MD 20764

    Perfect little rancher in a water access community. 3 bedrooms, 2 full baths, and a full fenced yard. Heated family/sun room out back and setup for a stackable washer/dryer inside.

    Kyle Squires Lazar Real Estate

    4738 Washington Ave, Shady Side, MD 20764
  • 1172 Cedar Ave, Shady Side, MD 20764
    1172 Cedar Ave, Shady Side, MD 20764
    1172 Cedar Ave, Shady Side, MD 20764
    /45

    $325,000

    • 3 Beds
    • 1 Bath
    • 864 Sq Ft

    1172 Cedar Ave, Shady Side, MD 20764

    Welcome to Cedarhurst on the Bay, a charming waterfront community on the Shady Side Peninsula, conveniently located between Annapolis and Deale Maryland. This cute, updated rancher style home offers a rare affordable opportunity to enjoy Chesapeake Bay living, just one hour from the City. So much potential! Make it your weekend retreat, an Air B&B, or perhaps a tranquil place to retire, without

    James Basuel Weichert, REALTORS

    1172 Cedar Ave, Shady Side, MD 20764
  • 5235 Al Jones Dr, Shady Side, MD 20764
    5235 Al Jones Dr, Shady Side, MD 20764
    5235 Al Jones Dr, Shady Side, MD 20764
    /17

    $349,870

    • Land
    • 6,534 Sq Ft
    • $2,332,467 per Acre

    5235 Al Jones Dr, Shady Side, MD 20764

    Unique Waterfront Lot Opportunity at Columbia Beach – Build Your Dream Home on the Chesapeake Bay. Don't miss this rare chance to own a buildable waterfront lot in the serene, gated community of Columbia Beach, offering breathtaking views of the Chesapeake Bay. This exclusive neighborhood is just 30 minutes from the I-495 Beltway and Annapolis, and only 45 minutes to Washington, D.C., and the

    Rodrigo Cruz Long & Foster Real Estate, Inc.

    5235 Al Jones Dr, Shady Side, MD 20764
  • 1205 Poplar Ave, Shady Side, MD 20764
    1205 Poplar Ave, Shady Side, MD 20764
    /2

    $25,000

    • Land
    • 4,791 Sq Ft
    • $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 7/24/2026, 10:00 AM. Bidding ends 7/28/2026, 1:00 PM. The list price is the 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
  • 1161 Steamboat Rd, Shady Side, MD 20764
    1161 Steamboat Rd, Shady Side, MD 20764
    1161 Steamboat Rd, Shady Side, MD 20764
    /37

    $439,900

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

    1161 Steamboat Rd, Shady Side, MD 20764

    Welcome to this charming home located in a sought-after water-privileged community, just a short walk to the beach, boat slips, playground, boat ramp, and other neighborhood amenities. The main level features a spacious primary suite with a private full bath, offering convenient one-level living. The beautifully appointed kitchen boasts a center island with a gas cooktop, wall oven, abundant

    Ray Mudd Schwartz Realty, Inc.

    1161 Steamboat Rd, Shady Side, MD 20764
  • 1445 & 1447 Haile Pkwy, Shady Side, MD 20764
    1445 & 1447 Haile Pkwy, Shady Side, MD 20764
    /2

    $100,000

    • Land
    • 29,620 Sq Ft
    • $147,059 per Acre

    1445 & 1447 Haile Pkwy, Shady Side, MD 20764

    Discover the perfect retreat from city life in the serene setting of Shady Side, MD. This parcel of land offers a rare opportunity to build your dream home amidst nature’s beauty. Tucked away in a peaceful community, the property provides the ideal balance of tranquility and accessibility. With convenient access to Route 2, commuting to Annapolis, Baltimore, or Washington, D.C., is effortless—yet

    Joan Stansfield Samson Properties

    1445 & 1447 Haile Pkwy, Shady Side, MD 20764
  • 1495 Shady Rest Rd, Shady Side, MD 20764
    1495 Shady Rest Rd, Shady Side, MD 20764
    /2

    $125,000

    • Land
    • 4 Acres
    • $31,250 per Acre

    1495 Shady Rest Rd, Shady Side, MD 20764

    Discover a unique investment opportunity with this expansive 4-acre parcel of land, perfect for those looking to capitalize on future development potential. Nestled in a serene setting, this property offers ample space for creative vision-whether you envision a private retreat, agricultural venture, or a residential community. The generous lot size provides flexibility for various projects,

    Shawn Kerr Union Preferred Realty

    1495 Shady Rest Rd, Shady Side, MD 20764
  • 1005 Hawk Channel Ct, West River, MD 20778
    1005 Hawk Channel Ct, West River, MD 20778
    1005 Hawk Channel Ct, West River, MD 20778
    /72

    $520,000

    $30K PRICE DROP
    • 4 Beds
    • 2.5 Baths
    • 1,812 Sq Ft

    1005 Hawk Channel Ct, West River, MD 20778

    Agents - please see agent notes! Welcome to the rarely available water- privileged Cedarlea community in West River—Tucked away at the end of a quiet, family-friendly cul-de-sac, this beautifully maintained 4-bedroom, 2.5-bath home offers the perfect blend of comfort, space, and privacy and is ready for its new owners. From the moment you arrive, the inviting front porch sets the tone for relaxed

    Stephanie Smith Douglas Realty, LLC

    1005 Hawk Channel Ct, West River, MD 20778
  • 1186 & 1188 Poplar Ave, Shady Side, MD 20764
    1186 & 1188 Poplar Ave, Shady Side, MD 20764
    /2

    $120,000

    • Land
    • 19,166 Sq Ft
    • $272,727 per Acre

    1186 & 1188 Poplar Ave, Shady Side, MD 20764

    Sale includes both 1186 & 1188 Poplar Ave. Lots: 10,11,12,13 Rare opportunity to purchase two adjoining parcels totaling approximately 19,000 square feet or nearly 1/2 acre in the water-privileged community of Cedarhurst on the Bay. Build your dream home and enjoy the relaxed Chesapeake Bay lifestyle that makes Shady Side one of Anne Arundel County's hidden gems. Community amenities include Bay

    Adam Carpenter Keller Williams Flagship

    1186 & 1188 Poplar Ave, Shady Side, MD 20764
  • 1650 Cedar Ln, Shady Side, MD 20764
    1650 Cedar Ln, Shady Side, MD 20764
    1650 Cedar Ln, 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
  • 4958 Lerch Dr, Shady Side, MD 20764
    4958 Lerch Dr, Shady Side, MD 20764
    4958 Lerch Dr, Shady Side, MD 20764
    /18

    $995,000

    Open Sat 11AM - 1PM Coming Soon
    • 3 Beds
    • 2 Baths
    • 1,887 Sq Ft

    4958 Lerch Dr, Shady Side, MD 20764

    COMING SOON - Great price for this exquisite, recently renovated coastal waterfront retreat offering a harmonious blend of luxury and comfort with abundant water views throughout. This home features three spacious bedrooms, one of which is conveniently located on the main level, and two elegantly appointed bathrooms, showcasing upgraded countertops and a walk-in shower. The open floor plan

    Bill Beam Beam Realty Group, Inc.

    4958 Lerch Dr, Shady Side, MD 20764
  • 5314 Al Jones Dr, Shady Side, MD 20764
    5314 Al Jones Dr, Shady Side, MD 20764
    5314 Al Jones Dr, Shady Side, MD 20764
    /62

    $649,990

    New Construction $10K PRICE DROP
    • 4 Beds
    • 2.5 Baths
    • 2,710 Sq Ft

    5314 Al Jones Dr, Shady Side, MD 20764

    6/26/26. Home is under roof ready for drywall. August 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

    Ray Mudd Schwartz Realty, Inc.

    5314 Al Jones Dr, Shady Side, MD 20764
  • 5280 Cedar St, West River, MD 20778
    5280 Cedar St, West River, MD 20778
    5280 Cedar St, West River, MD 20778
    /3

    $69,999

    $10K PRICE DROP
    • Land
    • 1.04 Acres
    • $67,307 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

Showing Results 1 - 40, Page 1 of 2

Maryland Anne Arundel County

Real Estate & Homes for Sale in Shady Side, MD

Why Live in Shady Side

Life in Shady Side revolves around the water. Facing the Chesapeake Bay on a peninsula in Anne Arundel County, this area is commutable to metros like Annapolis and Washington, D.C., but still offers a slow-paced life on the water. “I think it’s a ...

Learn more about living in Shady Side

Frequently Asked Questions

What is the average home price in Shady Side, MD?
Homes for sale in Shady Side, MD have an average home price of $592,140.
How many homes have sold over the last 12 months in Shady Side, MD?
92 homes have sold in Shady Side, MD over the last 12 months.
What is the average household income in Shady Side, MD?
The average household income in Shady Side, MD is $141K.
What are the most popular zip codes in Shady Side, MD?
The most popular zip codes in Shady Side, MD include 20764, 20778, 20733, 20776 and 20751.
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 6.55%, your estimated principal and interest payment would be $2,290 a month plus property taxes, HOA fees, home insurance, PMI, and utilities. Using the 28% rule, you would need to make at least $98K 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 $141K.
How are the schools in Shady Side, MD?
Shady Side, MD has highly rated public and private schools. Some of the best schools in Shady Side based on Niche Grades are Deale Elementary School, Shady Side Elementary School and Southern Middle School. Browse all the schools in Shady Side, MD to learn more.

Home Prices in Shady Side, MD

The median home sale price in Shady Side, MD is $440,000, up 10% year-over-year. Homes in Shady Side sell in 42 days on average, compared to the national average of 56 days.

Home Price Trends

Median Sale Price
$440,000
Median Single Family Sale Price
$450,000
Median 2 Bedroom Sale Price
$325,000
Median 1 Bedroom Sale Price
$315,000
Average Price Per Sq Ft
$319
Number of Homes for Sale
33
Last 12 months Home Sales
92
Months of Supply
4.30
Median List Price
$450,000
Median Change From 1st List Price
0%
Median Home Sale Price YoY Change
10%
How to Buy a Home How to Finance a Home How to Sell a Home

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