44

Shady Side, MD Homes for Sale

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  • 1199 Oak Ave, Shady Side, MD 20764
    1199 Oak Ave, Shady Side, MD 20764
    1199 Oak Ave, Shady Side, MD 20764
    /32

    $399,900

    • 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
  • 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

    (410) 883-0935

    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
    /53

    $674,990

    New Construction $25K PRICE INCREASE
    • 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
  • 1225 Juniper St, Shady Side, MD 20764
    1225 Juniper St, Shady Side, MD 20764
    1225 Juniper St, Shady Side, MD 20764
    /33

    $595,990

    New Construction $16K PRICE INCREASE
    • 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
  • 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
  • 4921 Olive St, Shady Side, MD 20764
    4921 Olive St, Shady Side, MD 20764
    4921 Olive St, Shady Side, MD 20764
    /31

    $419,900

    Open Sat 10AM - 12PM
    • 3 Beds
    • 1 Bath
    • 1,008 Sq Ft

    4921 Olive St, Shady Side, MD 20764

    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 entertain on the cozy screened-in front porch, or step out into the level,

    Eric Hovanky Redfin Corp

    4921 Olive St, Shady Side, MD 20764
  • 4725 Frederick Ave, Shady Side, MD 20764
    4725 Frederick Ave, Shady Side, MD 20764
    4725 Frederick Ave, Shady Side, MD 20764
    /31

    $465,000

    $14K PRICE DROP
    • 3 Beds
    • 2 Baths
    • 912 Sq Ft

    4725 Frederick Ave, Shady Side, MD 20764

    Adorable and fully renovated rancher situated on a rare double lot in the water-oriented Idlewild community of Shady Side! This cozy yet spacious home has been thoughtfully updated from top to bottom and offers easy one-level living with modern finishes throughout. Open concept living and kitchen area overlooks the expansive rear yard, creating the perfect space for entertaining or everyday

    Colleen Kerrigan Redfin Corp

    4725 Frederick Ave, 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

    $550,000

    $25K 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
  • 1527 Lincoln Rd, Shady Side, MD 20764
    1527 Lincoln Rd, Shady Side, MD 20764
    1527 Lincoln Rd, Shady Side, MD 20764
    /30

    $424,700

    • 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
    /2

    $535,000

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

    1183 Cedar Ave, Shady Side, MD 20764

    Photos coming soon! Rarely available and proudly offered for the first time, this spacious split-foyer home sits on nearly a quarter-acre lot in the desirable water-privileged community of Cedarhurst. Built and lovingly maintained by the original owner, this home features 4 bedrooms, 3 full bathrooms, two separate living areas, and an updated open-concept kitchen designed for comfortable everyday

    John Tarpley Schwartz Realty, Inc.

    1183 Cedar Ave, 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

    $569,900

    New Construction
    • 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

    Open Sat 11AM - 1PM
    • 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
  • 1161 Steamboat Rd, Shady Side, MD 20764
    1161 Steamboat Rd, Shady Side, MD 20764
    1161 Steamboat Rd, Shady Side, MD 20764
    /30

    $444,000

    $35K PRICE DROP
    • 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
  • 4721 Oak Rd, Shady Side, MD 20764
    4721 Oak Rd, Shady Side, MD 20764
    4721 Oak Rd, Shady Side, MD 20764
    /59

    $1,160,000

    • 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
  • 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

    $149,999

    • Land
    • 6,098 Sq Ft
    • $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
  • 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
  • 5771 Shady Side Rd, Churchton, MD 20733
    5771 Shady Side Rd, Churchton, MD 20733
    /2

    $40,000

    • Land
    • 14,810 Sq Ft
    • $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
  • 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
  • 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 6/2/2026 @ 10:00 AM. Bidding ends 6/4/2026 @ 12:50 PM. 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 easy

    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
  • 4738 Washington Ave, Shady Side, MD 20764
    4738 Washington Ave, Shady Side, MD 20764
    4738 Washington Ave, Shady Side, MD 20764
    /27

    $399,900

    • 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
    /42

    $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
  • 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 6/9/2026 @ 10:00 AM. Bidding ends 6/11/2026 @ 12:05 PM. 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 arteries

    Adam Shpritz Ashland Auction Group LLC

    1205 Poplar Ave, Shady Side, MD 20764
  • 1617 Winters Ave, Shady Side, MD 20764
    1617 Winters Ave, Shady Side, MD 20764
    1617 Winters Ave, Shady Side, MD 20764
    /37

    $354,500

    • 2 Beds
    • 2 Baths
    • 1,000 Sq Ft

    1617 Winters Ave, Shady Side, MD 20764

    Discover your waterfront retreat with Chesapeake Bay views, community water access, and an ideal location for both everyday living and weekend escapes. The stunning upper-level living area features vaulted ceiling, a classic wood-burning fireplace, and beautiful hardwood flooring that creates a warm and inviting atmosphere. Large, upgraded windows fill the home with natural light while showcasing

    Jeffrey Lewis Berkshire Hathaway HomeServices PenFed Realty

    1617 Winters Ave, 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

    $540,000

    $10K PRICE DROP
    • 4 Beds
    • 2.5 Baths
    • 1,812 Sq Ft

    1005 Hawk Channel Ct, West River, MD 20778

    BUYERS GOT COLD FEET! No inspections were completed. 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

    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
  • 5331 Sweetwater Dr, West River, MD 20778
    5331 Sweetwater Dr, West River, MD 20778
    5331 Sweetwater Dr, West River, MD 20778
    /61

    $850,000

    $50K PRICE DROP
    • 4 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
  • 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
  • 4912 Beech St, Shady Side, MD 20764
    4912 Beech St, Shady Side, MD 20764
    4912 Beech St, Shady Side, MD 20764
    /40

    $365,000

    • 2 Beds
    • 2 Baths
    • 864 Sq Ft

    4912 Beech St, Shady Side, MD 20764

    Welcome to this charming 2-bedroom, 2-bath home in the water-oriented community of Avalon Shores. Perfect for those looking to start out, scale down, or a second home! Freshly updated with new flooring, a new roof, and fresh paint- this home is truly move-in ready! Enjoy a fully renovated bathroom, a spacious deck, and a fully fenced backyard—perfect for pets, gatherings, or quiet relaxation.Step

    Juliet Patterson Samson Properties

    4912 Beech St, 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
    /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
  • 5211 Al Jones Dr, Shady Side, MD 20764
    5211 Al Jones Dr, Shady Side, MD 20764
    5211 Al Jones Dr, Shady Side, MD 20764
    /39

    $550,000

    • 2 Beds
    • 1.5 Baths
    • 1,244 Sq Ft

    5211 Al Jones Dr, Shady Side, MD 20764

    Non-riparian waterfront home offering sweeping, unobstructed views of the Chesapeake Bay. Wake each morning to breathtaking sunrises over the water, best enjoyed from your expansive deck with a cup of coffee in hand—an experience that never gets old. Inside, the home is filled with natural light and features an open-concept layout designed to maximize those stunning bay views. The main level

    Ray Mudd Schwartz Realty, Inc.

    5211 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
  • 1582 Snug Harbor Rd, Shady Side, MD 20764
    1582 Snug Harbor Rd, Shady Side, MD 20764
    1582 Snug Harbor Rd, Shady Side, MD 20764
    /6

    $619,900

    Open House 6/28 Coming Soon
    • 4 Beds
    • 2.5 Baths
    • 1,915 Sq Ft

    1582 Snug Harbor Rd, Shady Side, MD 20764

    Rare 1-acre private lot located in sought after Idlewilde Acres backing up to Jack Creek Park! Upgrades include: 2023 enlarged rear decking, ADT Alarm system, generator hook up. 2023 full kitchen renovation - upgraded cabinetry, leathered granite counter-top, farmhouse sink, back splash upgraded stove top / microwave, and all new wood flooring on main level. Renovated half bath-2023. 2024 new

    Steven Songer Maryland Waterfront Properties LLC

    1582 Snug Harbor Rd, Shady Side, MD 20764
  • 1462 Snug Harbor Rd, Shady Side, MD 20764
    1462 Snug Harbor Rd, Shady Side, MD 20764
    1462 Snug Harbor Rd, 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 MC heavy commercial 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

    George Heine Schwartz Realty, Inc.

    1462 Snug Harbor Rd, Shady Side, MD 20764
  • 1209 Johnson Dr, Shady Side, MD 20764
    1209 Johnson Dr, Shady Side, MD 20764
    1209 Johnson Dr, Shady Side, MD 20764
    /37

    $609,990

    New Construction $30K PRICE INCREASE
    • 4 Beds
    • 2.5 Baths
    • 2,068 Sq Ft

    1209 Johnson Dr, Shady Side, MD 20764

    6/15/26 HOME UNDER ROOF. EXPECTED JULY/AUGUST 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

    Ray Mudd Schwartz Realty, Inc.

    1209 Johnson Dr, Shady Side, MD 20764
  • 1430 Haile Pkwy, Shady Side, MD 20764
    1430 Haile Pkwy, Shady Side, MD 20764
    1430 Haile Pkwy, Shady Side, MD 20764
    /33

    $650,000

    New Construction
    • 4 Beds
    • 3.5 Baths
    • 3,100 Sq Ft

    1430 Haile Pkwy, Shady Side, MD 20764

    There aren't many opportunities left to build brand new in Anne Arundel County at this price point, and 1430 Haile Parkway is one of them. Haile Parkway is quiet, wooded, and tucked into the laid-back charm of Shady Side, close enough to everything you need, far enough away to actually exhale. New construction at this level of quality and finish from one of the area's most respected builders is a

    Lynn Peaper Hubble Bisbee Christie's International Real Estate

    1430 Haile Pkwy, Shady Side, MD 20764
  • 1217 Pine Ave, Shady Side, MD 20764
    1217 Pine Ave, Shady Side, MD 20764
    1217 Pine Ave, Shady Side, MD 20764
    /79

    $450,000

    • 3 Beds
    • 2 Baths
    • 2,006 Sq Ft

    1217 Pine Ave, Shady Side, MD 20764

    Welcome to this beautifully maintained Colonial perfectly positioned on a desirable corner lot in the water-oriented community of Cedarhurst—where Chesapeake Bay living is part of everyday life. Just in time for summer, enjoy the opportunity to lease a boat slip for only $400 per year with direct access to the Chesapeake Bay, making weekends on the water easier than ever. Inside, you’ll find

    Nicki Palermo RE/MAX One

    1217 Pine Ave, Shady Side, MD 20764

Showing Results 1 - 40, Page 1 of 2

Maryland Anne Arundel County Shady Side

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 $578,427.
How many homes have sold over the last 12 months in Shady Side, MD?
91 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 20778, 20764, 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 $449,975. If you put a 20% down payment of $90,000 and had a 30-year fixed mortgage with an interest rate of 6.52%, your estimated principal and interest payment would be $2,280 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 $439,000, up 11% year-over-year. Homes in Shady Side sell in 41 days on average, compared to the national average of 58 days.

Home Price Trends

Median Sale Price
$439,000
Median Single Family Sale Price
$447,000
Median 2 Bedroom Sale Price
$330,000
Median 1 Bedroom Sale Price
$315,000
Average Price Per Sq Ft
$325
Number of Homes for Sale
27
Last 12 months Home Sales
91
Months of Supply
3.60
Median List Price
$449,975
Median Change From 1st List Price
0%
Median Home Sale Price YoY Change
11%
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