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Homes for Sale in 20764

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  • /52

    $460,000 Coming Soon

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

    1168 Maple Ave, Shady Side, MD 20764

    Coming Soon! More Remarks to Follow! 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.

    Ryan Webster RE/MAX United Real Estate

    1168 Maple Ave, Shady Side, MD 20764
  • /2

    $439,900 Coming Soon

    • 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
  • /6

    $239,000 Coming Soon

    • 2 Beds
    • 2 Baths
    • 1,028 Sq Ft

    4715 Girton Ave, Shady Side, MD 20764

    Welcome to 4715 Girton Avenue in the Idlewild community. This home features 2 bedrooms, 2 full bathrooms, and 1,028 square feet of living space. With a little vision and TLC, this property offers a wonderful opportunity to create your own private oasis. The home has great bones and plenty of potential for customization, making it perfect for buyers looking to add their personal touch. The kitchen

    Brian Snider Douglas Realty, LLC

    4715 Girton 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
  • /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
  • /17

    $599,900 Coming Soon

    • 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 sunrises 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
  • /2

    $395,000 Coming Soon

    • 3 Beds
    • 2 Baths
    • 1,400 Sq Ft

    1176 Spruce Ave, Shady Side, MD 20764

    Professional photos will be taken on the 24th. Welcome to this well-maintained 1,400 sq. ft. Cape Cod featuring 3 bedrooms and 2 full baths. A paved driveway accommodates 3-4 cars, with a stamped concrete walkway leading to a spacious front porch. Inside, the main level features vaulted ceilings, a 2nd-floor balcony overlook, and luxury vinyl plank flooring. The living area flows seamlessly into

    Steve Brien Home Towne Real Estate

    1176 Spruce Ave, Shady Side, MD 20764
  • /39

    $460,000

    • 4 Beds
    • 3 Baths
    • 1,632 Sq Ft

    5191 Spring Ave, Shady Side, MD 20764

    Welcome to 5191 Spring Avenue in the charming, water-oriented community of Cedarhurst on the Bay. Just steps from the water and community marina, this delightful Cape Cod captures the relaxed essence of coastal cottage living. Situated on a spacious corner lot, the property comes alive in the spring with mature plantings and established landscaping that surround the home, creating a colorful and

    Elizabeth Gould Long & Foster Real Estate, Inc.

    5191 Spring Ave, Shady Side, MD 20764
  • /31

    $599,999

    • 4 Beds
    • 2.5 Baths
    • 2,586 Sq Ft

    4951 Dogwood St, Shady Side, MD 20764

    Stunning 4BR / 2.5BA home at 4951 Dogwood Street, Shady Side — freshly painted,hardwood floors have been polished and carpets professionally cleaned, bright, open living with a NEW 2025 Aloha Pool private pool, pool-style is Chesapeake Atlantic 24x54 w/ Liner pad and Styrofoam Covering, NEW oversized deck 22 x 23 ideal for entertaining, 6‐ft privacy fence, and a 2‐car garage. Spacious primary

    Carey Laycock RE/MAX Leading Edge

    4951 Dogwood St, Shady Side, MD 20764
  • /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

    $595,000 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
  • /21

    $325,000

    • 2 Beds
    • 1.5 Baths
    • 1,728 Sq Ft

    1241 Steamboat Rd, Shady Side, MD 20764

    Estate sale handled by an attorney. This well-loved home has been in the same family since 1953 and is now ready for its next chapter. Offering generous living space and abundant potential, this property is ideal for buyers looking to build sweat equity and restore its original charm. Situated on a large lot, the sale also includes an additional 25' x 100' parcel located to the right of the home.

    Ray Mudd Schwartz Realty, Inc.

    1241 Steamboat 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 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

    $529,750

    • 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
  • /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
  • /31

    $350,000

    • 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
  • /2

    $100,000

    • Land
    • 0.68 Acre
    • $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

    Joan Stansfield Samson Properties

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

    $25,000

    • Land
    • 0.57 Acre
    • $43,860 per Acre

    0 Haile Pkwy Unit MDAA2127474, 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 MDAA2127474, 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

    Joan Stansfield Samson Properties

    1436 Haile Pkwy, 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
  • /49

    $419,900

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

    4721 Girton Ave, Shady Side, MD 20764

    Perfect time to buy this updated home with a detached garage in the beautiful Chesapeake Bay front communnity of Idlewilde! Main level bedroom and full bathroom, waterview from front second level bedroom, and off street parking. This home has been completely updated with the main level having luxury vinyl flooring and fresh paint. The spacious kitchen has granite countertops, wood cabinets, and

    Sheri Stevens Samson Properties

    4721 Girton Ave, Shady Side, MD 20764
  • /27

    $499,900

    • 4 Beds
    • 2.5 Baths
    • 2,176 Sq Ft

    1711 Columbia Beach Rd, Shady Side, MD 20764

    Nestled between serene waters, this home offers stunning, unobstructed views of Flag Pond from the rear and views of the Chesapeake Bay from the front. Enjoy watching local waterfowl and soaking in the natural beauty from every angle. Inside, the spacious kitchen opens to the family room, perfect for gathering, along with a formal living room and a main-level office or potential 5th bedroom.

    Ray Mudd Schwartz Realty, Inc.

    1711 Columbia Beach 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
  • /2

    $54,000

    • Land
    • 1.32 Acres
    • $40,909 per Acre

    1461 Cedarhurst Rd, Shady Side, MD 20764

    Escape the hustle and bustle of city life with this exceptional land opportunity in Shady Side, MD. Nestled in a tranquil community, this parcel offers the perfect setting to build your dream home surrounded by nature’s beauty. Enjoy the best of both worlds—peaceful seclusion with easy access to Route 2 and Route 4, making travel to Annapolis, Baltimore, and Washington, D.C., a breeze. Immerse

    Joan Stansfield Samson Properties

    1461 Cedarhurst Rd, 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
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