35

Homes for Sale in 20764

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  • /17

    $159,000

    1451 Shady Rest Rd, Shady Side, MD 20764

    Rare Shady Side opportunity on 1.58 acres near the Chesapeake Bay. 1451 Shady Rest Rd offers a partially constructed home where building began pre-Covid. The property is ready for a new owner to bring their vision. It includes a permitted and enlarged 3-bedroom septic system and an operational well, giving you a strong foundation for your new build. In this highly desirable South County area,

    Teal Clise EXP Realty, LLC

    1451 Shady Rest Rd, Shady Side, MD 20764
  • /41

    $420,000 Open Thu 4PM - 6PM

    • 3 Beds
    • 2.5 Baths
    • 1,630 Sq Ft

    4742 Chestnut Rd, Shady Side, MD 20764

    Experience refined living in this beautifully maintained 3-bedroom, 2.5-bath Colonial, perfectly nestled on a quiet, tree-lined street. This distinguished residence offers timeless curb appeal with a welcoming front porch, a thoughtfully designed interior, and a nicely appointed kitchen ideal for both daily living and entertaining. The home features a spacious primary suite, generously sized

    Diego Reyes Long & Foster Real Estate, Inc.

    4742 Chestnut Rd, Shady Side, MD 20764
  • /29

    $697,015

    • 4 Beds
    • 2.5 Baths
    • 2,200 Sq Ft

    4938 Rullman Rd, Shady Side, MD 20764

    Westelee Welcome's You Home! This 2.5 year old "Pottery Barn" Colonial home is set perfectly on a corner lot with views of the West River. This home has 4 bedrooms and 2.5 baths. Patio was just put in and a 6 foot privacy fence around the backyard in 2024. GREAT FOR HAVING A CRAB FEAST IN THE SUMMER OR BONFIRES IN THE FALL. THIS YARD IS GREAT FOR ENTERTAINING BRING YOUR FAMILY AND FRIENDS. There

    Carey Laycock RE/MAX Leading Edge

    4938 Rullman Rd, Shady Side, MD 20764
  • /27

    $375,000

    • 3 Beds
    • 2.5 Baths
    • 1,512 Sq Ft

    1512 Lincoln Rd, Shady Side, MD 20764

    Home Sweet Home! Come tour this 2 level, 3 bedroom, 2 full bath just a couple blocks to the water. Situated in Columbia Beach, feel like you're vacationing year round! Whether your taking a walk in the gated community, or entertaining in the spacious home, you'll enjoy living here! No HOA. Please read agent remarks.

    Cheryl Bare CENTURY 21 New Millennium

    1512 Lincoln Rd, Shady Side, MD 20764
  • /32

    $289,000

    • 2 Beds
    • 1 Bath
    • 714 Sq Ft

    4717 Frederick Ave, Shady Side, MD 20764

    Welcome to 4717 Frederick Avenue — a charming and updated cottage just two blocks from the West River in the Idlewilde on the Bay community. This 2-bedroom, 1-bath ranch-style home offers comfortable one-level living with thoughtful improvements throughout. Step inside to a bright, open living area featuring neutral finishes and a cozy fireplace, ideal for everyday relaxation. The renovated

    James Weiskerger Next Step Realty

    4717 Frederick Ave, Shady Side, MD 20764
  • /41

    $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 and pain- 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 outside and

    Juliet Patterson Samson Properties

    4912 Beech St, Shady Side, MD 20764
  • /27

    $295,000

    • 2 Beds
    • 1 Bath
    • 704 Sq Ft

    1213 Oak Ave, Shady Side, MD 20764

    A Charming Cedarhurst Cottage Near the Water - This charming 1944 cottage in Cedarhurst on the Bay offers easy coastal living and only a few houses from the Bay and the community amenities. Recent improvements within the last year include a new roof, new windows, a new hot water tank and a new water pressure tank. The kitchen has white cabinetry and there is a small laundry room with a washer and

    Agent Photo

    Bill Franklin

    Long & Foster Real Estate, Inc.

    (443) 381-0652

    1213 Oak Ave, Shady Side, MD 20764
  • /35

    $799,900

    • 3 Beds
    • 2.5 Baths
    • 2,225 Sq Ft

    6508 Shady Side Rd, Shady Side, MD 20764

    For buyers seeking a quicker move-in, the same model is currently under construction less than a mile away and will be completed in approximately 30 days, offering the perfect opportunity to preview the craftsmanship and finishes in person or purchase if a faster timeline is preferred.This to-be-built Modern Farmhouse by local builder Laine Street Homes blends timeless architecture with

    Joshua Mast HomeSource Pro Real Estate

    6508 Shady Side 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

    $355,000

    • 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 retreat 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
  • /29

    $815,000 New Construction

    • 4 Beds
    • 2.5 Baths
    • 2,485 Sq Ft

    6512 Shady Side Rd, Shady Side, MD 20764

    For buyers desiring a quicker move-in, this same model is under construction less than a mile away and will be completed in approximately 30 days — a perfect opportunity to preview the craftsmanship and finishes in person. This to-be-built custom Arts & Crafts residence by local builder Laine Street Homes blends timeless design with modern luxury. Set on a premium 1.5-acre homesite, the property

    Joshua Mast HomeSource Pro Real Estate

    6512 Shady Side Rd, Shady Side, MD 20764
  • /53

    $444,900

    • 4 Beds
    • 2 Baths
    • 1,300 Sq Ft

    4738 Idlewilde Rd, Shady Side, MD 20764

    NEW PRICE!! Amazing opportunity to own an affordable beautifully remodeled home in the waterfront community. Just a short walk from the Chesapeake Bay, this 4-BR, 2-BA home offers approx. 1,300 sq ft of modern living, including a Brand-New signature designer kitchen with an eat-in island, New trash compactor, New security system, New lighting, New Appliances and High End finishes

    Agent Photo

    Jesse Marks

    Realinvestors Real Estate Services, LLC

    (410) 927-5552

    4738 Idlewilde Rd, 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

    $65,000

    • Land
    • 0.3 Acre
    • $216,667 per Acre

    1408 & 1410 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 & Route 4, commuting to Annapolis, Baltimore, or Washington, D.C.,

    Joan Stansfield Samson Properties

    1408 & 1410 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,

    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
  • /44

    $609,990 New Construction

    • 4 Beds
    • 2.5 Baths
    • 2,424 Sq Ft

    1302 Spruce St, Shady Side, MD 20764

    10/10/25 Update: Home is under roof. Estimated completion is projected for January/February 2026. Introducing the Adams model — a beautifully designed home featuring an open-concept floor plan that blends comfort, style, and functionality. At the center of the home, the gourmet kitchen boasts a large island, stainless steel appliances, a walk-in pantry, and premium finishes—perfect for everyday

    Ray Mudd Schwartz Realty, Inc.

    1302 Spruce St, Shady Side, MD 20764
  • /20

    $554,500

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

    5211 Al Jones Dr, Shady Side, MD 20764

    Coastal Living in a Gated Waterfront Community a Short Distance from Annapolis and Washington, D.C. Awaits You!Discover the perfect blend of charm and comfort in this 2-bedroom, 1.5-bath Cottage by the Bay, located in the desirable gated waterfront community of Columbia Beach. With stunning bay views, this home offers a peaceful escape just steps from the water.Inside, enjoy an

    Stephanie Burns Coldwell Banker Realty

    5211 Al Jones Dr, Shady Side, MD 20764
  • /6

    $375,000 Pre-Foreclosure

    • 3 Beds
    • 2 Baths
    • 1,408 Sq Ft

    4900 Thomas Dr, Shady Side, MD 20764

    Just two doors from the water and steps from a children’s park and boat ramp, this 3-bedroom, 2-bath rancher offers 1,408 sq. ft. of potential. Renovations are underway with many improvements already complete—kitchen updates started, dishwasher included but not yet installed, and bedrooms ready for new flooring. New flooring will be installed throughout the home prior to closing, offering buyers

    Shannon Thayer Douglas Realty, LLC

    4900 Thomas Dr, Shady Side, MD 20764
  • /14

    $54,900

    • Land
    • 1.53 Acres
    • $35,882 per Acre

    6152 Shady Side Rd, Shady Side, MD 20764

    1.53 Acre lot zoned R1 located in within Anne Arundel County in quiet Shady Side MD. Take a drive and see how this prime location can fulfill your needs! Owner Financing Available! Buyer to ascertain all necessary information for their intended use. Seller prefers Diana Khan of DK Law Group for Title and Closing.Property lines shown are approximate and need to be verified by purchaser.

    Agent Photo

    Kara Leddy

    Coldwell Banker Realty

    (410) 701-3561

    6152 Shady Side Rd, Shady Side, MD 20764
  • /31

    $534,969

    • 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 featuring a gas fireplace and a sliding door that leads 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

    Ray Mudd Schwartz Realty, Inc.

    4949 Idlewilde Rd, Shady Side, MD 20764
  • /8

    $239,500

    • Land
    • 8.19 Acres
    • $29,243 per Acre

    6118 Shady Side Rd, Shady Side, MD 20764

    Only 31k per acre! This wonderful 8.19 acre wooded level lot conveniently located to the Chesapeake & West River is loaded with potential & ready to build your dream home! Off a hard surface road this terrific property is just minutes to multiple marinas, yacht clubs & harbors, shopping, dining and just 25 minutes to Annapolis & 45 minutes to DC. Public water and sewer available

    Tem Popoola Real Broker, LLC

    6118 Shady Side Rd, 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
  • /24

    $1,524,000 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’ largest luxury waterfront builder. Located in the desirable Columbia Beach neighborhood, this coastal-style home will offer 3,700 sqft of living space and the rare combination of panoramic Chesapeake Bay views with the protection of a cove-front setting. Designed for modern waterfront living, the open-concept layout features soaring 10' ceilings

    Lynn Peaper Hubble Bisbee Christie's International Real Estate

    5235 Al Jones Dr, Shady Side, MD 20764
  • /32

    $480,000

    • 5 Beds
    • 2 Baths
    • 1,812 Sq Ft

    1220 Grove Ave, Shady Side, MD 20764

    This spacious 5 bedroom, 2 full bath split foyer is located in the highly desirable Community; Cedarhurst on the Bay. This remarkable property showcases the epitome of every day, vacation living with stunning views of The Chesapeake Bay. You will quickly be captivated by the grandeur that awaits you. The open layout seamlessly connects the living, dining and kitchen area, creating an ideal

    Jessica Gosman-Bowen Curtis Real Estate Company

    1220 Grove Ave, Shady Side, MD 20764
  • /2

    $285,000

    • 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
  • /28

    $275,000

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

    4725 Idlewilde Rd, Shady Side, MD 20764

    Calling all investors, second-home seekers, and visionaries—this is the project you’ve been waiting for! AND it just got better with a price improvement!! Located just steps from the water in the charming community of Idlewilde, this 2-bedroom cottage-style home sits on a rare double lot with Chesapeake Bay views from the backyard and access to fantastic community amenities.While the

    Clinton Auman EXP Realty, LLC

    4725 Idlewilde 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
  • /39

    $300,000

    • 4 Beds
    • 2 Baths
    • 1,344 Sq Ft

    6070 Shady Side Rd, Shady Side, MD 20764

    Don't miss this wonderful opportunity to own this porch front home seated in an expansive private lot approximately 3.38 acres. Home features hardwood floors that flows from the combined living and dining rooms to the nice sized kitchen with appliances and main level bedroom and bath. There is a full bath on each level and three more bedrooms on the upper level. The sunroom with wide windows and

    Gina Gargeu Century 21 Downtown

    6070 Shady Side 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
  • /6

    $259,999

    • Land
    • 0.77 Acre
    • $337,661 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
  • /15

    $997,000

    • Land
    • 1.6 Acres
    • $623,125 per Acre

    1133 Steamboat Rd, Shady Side, MD 20764

    BRING ON THE RIVER BOATS... Unparalleled access to the Chesapeake Bay, ideal for boating, sailing, fishing and crabbing enthusiasts!!! Discover the perfect canvas for your waterfront dream home on this stunning undeveloped lot in the prestigious Shady Side community offering ample space for building a custom waterfront estate. With 80 feet of prime waterfront frontage on the Chesapeake Bay,

    John Halpin RE/MAX Premiere Selections

    1133 Steamboat Rd, Shady Side, MD 20764
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