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Homes for Sale in 20764

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  • /38

    $699,500 New Construction

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

    1195 Cedar Ave, Shady Side, MD 20764

    This beautifully crafted home blends timeless coastal charm with modern luxury. Featuring classic board and batten siding and a welcoming front porch, the exterior makes a striking first impression. Step inside to an open-concept layout that seamlessly connects the dining and family room, ideal for both everyday living and entertaining.At the heart of the home is a spacious kitchen

    Agent Photo

    Jamie Richardson

    Coldwell Banker Realty

    (410) 724-1563

    1195 Cedar Ave, Shady Side, MD 20764
  • /27

    $593,100

    • 3 Beds
    • 1.5 Baths
    • 1,152 Sq Ft

    1605 Depriest Dr, Shady Side, MD 20764

    Price Adjustment. It's better at the Beach! Incredible peninsula location with 180 degree views of the Chesapeake Bay in the gated community of Columbia Beach in Shady Side , Maryland. This 2 level 3B/1.5 BA home with an inverted floor plan is the perfect weekend retreat or full time main residence. Vacation every day! You can see the Chesapeake Bay Bridge on clear days right from your upper

    Lydia Newman Fairfax Realty Premier

    1605 Depriest Dr, Shady Side, MD 20764
  • /25

    $650,000

    • 2 Beds
    • 1.5 Baths
    • 1,540 Sq Ft

    4801 Avery Rd, Shady Side, MD 20764

    Water! Water everywhere! This adorable mid-century cottage faces Hopkins Cove , borders Parish Creek and looks out to the Chesapeake Bay Bridge. It is a dream come true for those who love living on the water, and could be your weekend getaway cottage. Not a fan of cottages? Then, go all in and remodel to make it your own! The possibilities are endless..... The property is being sold "as is".

    Theresa Kurtz EXP Realty, LLC

    4801 Avery Rd, Shady Side, MD 20764
  • /29

    $554,500 Open Sun 12PM - 2PM

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

    5211 Al Jones Dr, Shady Side, MD 20764

    Great New Price ... here is your chance to own and enjoy a coastal contemporary “cottage” with panoramic views and the soothing sounds of the Chesapeake Bay year round. This Bay fronting property has an open airy interior, warm and inviting, with two story vaulted ceilings, walls of windows which showcase the Bay view. The ease of main level living, enhanced with wood floors, includes the

    Celeste Blessin Coldwell Banker Realty

    5211 Al Jones Dr, Shady Side, MD 20764
  • /10

    $600,000

    • 2 Beds
    • 1 Bath
    • 862 Sq Ft

    1337 W River Rd, Shady Side, MD 20764

    Price Reduction!!Your Own Private Retreat, get away from the Rat Race and make this a great place for you and your family.1337 West River Road , located in Shady Side, MDis a secluded waterfront property that sits on 1.5 acres with 592 feet of waterfront on the South Creek.This property has a home with 2 beds and 1 bath that will need remodeling and/or teardown.it's located 1/4 mile off the main

    Bruce Thompson Long & Foster Real Estate, Inc.

    1337 W River Rd, Shady Side, MD 20764
  • /41

    $735,000

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

    1462 Snug Harbor Rd, Shady Side, MD 20764

    4 beds/ 1 full bath and 1/2 bath with shower.2144 SQ FT. Home and income opportunity goes with this four bedroom home on .57 acres of (C1B) commercial zoned property. Additional .375 acres and .1243 acres of (MA2) marine zoned property, totaling 1.0693 acres, with 135 feet of bulk headed waterfront, 200 foot pier, and 12 boat slips. Water depth from 4 to 8feet, that can accommodate boats in

    George Heine Schwartz Realty, Inc.

    1462 Snug Harbor Rd, Shady Side, MD 20764
  • /42

    $499,900 Open Sun 11AM - 1PM

    • 4 Beds
    • 2.5 Baths
    • 2,464 Sq Ft

    1347 W River Rd, Shady Side, MD 20764

    Welcome to 1347 W River Rd. – A Private Retreat on 2.02 Acres in Shady Side, MD. This two-story colonial offers privacy, space, and the perfect blend of classic charm and a few modern updates. With approx. 2,464 sq ft of living space, this 4-bedroom, 2.5-bath home provides ample room for everyday living and entertaining. Step into the spacious foyer and take in the warmth of the shaker-style

    Elizabeth DuLaney EXP Realty, LLC

    1347 W River Rd, Shady Side, MD 20764
  • /18

    $375,000

    • 2 Beds
    • 1.5 Baths
    • 852 Sq Ft

    1700 Bayview Rd, Shady Side, MD 20764

    Don't miss this charming and well-maintained home! The main level features stylish LVP flooring and a bright, sunny eat-in kitchen with granite countertops. A convenient powder room includes a new pedestal sink. Sliding door from the kitchen open to a deck that overlooks a fully fenced backyard—perfect for relaxing or entertaining. Upstairs, you’ll find two spacious bedrooms and a full bath. This

    Ray Mudd Schwartz Realty, Inc.

    1700 Bayview Rd, Shady Side, MD 20764
  • /39

    $469,900

    • 3 Beds
    • 2.5 Baths
    • 1,440 Sq Ft

    1330 Jordan Dr, Shady Side, MD 20764

    Welcome to 1330 Jordan Drive, a charming 3-bedroom, 2.5-bathroom home nestled in the highly desirable Avalon Shores community in Shady Side, Maryland.This well-maintained home strikes the perfect balance between comfort and character. The covered front porch invites you to unwind and enjoy seasonal water views, setting the tone for peaceful, waterfront living. Inside, you’ll find a

    Emily Motto Investors Management, Inc.

    1330 Jordan Dr, Shady Side, MD 20764
  • /97

    $399,500

    • 4 Beds
    • 1.5 Baths
    • 1,399 Sq Ft

    1199 Oak Ave, Shady Side, MD 20764

    Welcome to Cedarhurst On The Bay — Your Bayside Retreat Awaits!Nestled in the serene, historic enclave of Cedarhurst On The Bay in Shady Side, Maryland, this beautiful single‐level home is the perfect blend of comfort, convenience, and coastal charm. Set on a generous double lot and built on a durable slab foundation, this residence offers 4 bedrooms, 1.5 bathrooms, and a thoughtfully

    Vilas Wright Wright Real Estate, LLC

    1199 Oak Ave, Shady Side, MD 20764
  • /42

    $475,120

    • 5 Beds
    • 2.5 Baths
    • 2,051 Sq Ft

    1216 Grove Ave, Shady Side, MD 20764

    Chesapeake Bay views and close to the community dock and harbor! Feels like you are on vacation all year round! This home has 4 bedrooms 2.5 baths and a 3rd floor bonus room with balcony and Chesapeake Bay views! It can be used as a family room or a 5th bedroom! Owners suite also has a balcony with Bay views! Home has many new windows and the roof was replaced with Architectural shingles in

    Paul Lee Long & Foster Real Estate, Inc.

    1216 Grove Ave, Shady Side, MD 20764
  • /25

    $375,000

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

    4738 Washington Ave, Shady Side, MD 20764

    Charming Rancher Just Steps from the Bay Front!Nestled on a peaceful corner lot and surrounded by the serenity of a protected nature reserve, this inviting 3-bedroom, 1-bath single-level rancher offers the perfect blend of privacy, charm, and location. Just a short walk to the scenic bay front, you’ll enjoy the coastal lifestyle with morning strolls, sunsets, and water views just minutes

    Nicole Hatch Samson Properties

    4738 Washington Ave, Shady Side, MD 20764
  • /65

    $1,950,000 Open Sat 11AM - 12:30PM

    • 9 Beds
    • 6.5 Baths
    • 9,045 Sq Ft

    4701 Girton Ave, Shady Side, MD 20764

    HUGE PRICE REDUCTION !Welcome to 4701 Girton, waterfront estate boasting over 9,000 square feet sitting on an incredible point offering panoramic views to the Chesapeake Bay and West River. Views to take your breath away with over 250 ft of water frontage including rip rap, and bulkhead. There is plenty of room for your water toys with a deep-water pier, two boat lifts,12,000 lb, two jet ski

    Tammy Studebaker EXP Realty, LLC

    4701 Girton Ave, Shady Side, MD 20764
  • /67

    $1,100,000

    • 4 Beds
    • 2.5 Baths
    • 3,244 Sq Ft

    4715 Oak Rd, Shady Side, MD 20764

    Welcome to the Chesapeake Bay! Relax while sipping your morning coffee or unwinding with a glass of wine. This waterfront cottage offers over 3000 sf of living space with panoramic views from every room! Unique features include wood beams on the first and second levels; two staircases access the second level; authentic cedar doors, closets, and drawers take you back to the 1930s; while the

    Angie Carr Riverscape Realty

    4715 Oak Rd, Shady Side, MD 20764
  • /32

    $485,500

    • 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
  • /34

    $459,900 Open Sun 12PM - 2PM

    • 4 Beds
    • 2 Baths
    • 2,440 Sq Ft

    1440 Cedarhurst Rd, Shady Side, MD 20764

    Welcome to 1440 Cedarhurst Road! This beautifully maintained home offers over 2,400 square feet of comfortable living space, featuring 4 bedrooms and 2 bathrooms on a spacious, flat lot.Step inside to discover gleaming hardwood and tile flooring throughout. The heart of the home is a spacious kitchen with a center island, seamlessly connected to an open dining area. Just off the kitchen,

    Terry McAllister RE/MAX One

    1440 Cedarhurst Rd, Shady Side, MD 20764
  • /42

    $499,620

    • 5 Beds
    • 2.5 Baths
    • 2,051 Sq Ft

    1216 Grove Ave, Shady Side, MD 20764

    Recent Price reduction! Chesapeake Bay views and close to the community dock and harbor! Feels like you are on vacation all year round! This home has 4 bedrooms 2.5 baths and a 3rd floor bonus room with balcony and Chesapeake Bay views! It can be used as a family room or a 5th bedroom! Owners suite also has a balcony with Bay views! Home has many new windows and the roof was replaced with

    Paul Lee Long & Foster Real Estate, Inc.

    1216 Grove Ave, 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
  • /18

    $378,000

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

    1617 Winters Ave, Shady Side, MD 20764

    Welcome to 1617 Winters Ave – Coastal Charm with Modern Updates in Idlewild on the BayBeautifully updated and move-in ready, this 3-bedroom, 2-bath gem is nestled in the water-access community of Idlewild on the Bay. Situated just one block from the Chesapeake Bay, this home boasts fresh interior updates, a fully fenced yard, and two spacious decks ideal for entertaining or relaxing by

    John Kreamer Taylor Properties

    1617 Winters Ave, Shady Side, MD 20764
  • /83

    $2,250,000

    • 4 Beds
    • 2.5 Baths
    • 3,745 Sq Ft

    1100 Steamboat Rd, Shady Side, MD 20764

    Spectacular West River waterfront! A serene lot with stunning, panoramic water views, an elegant, custom-built home that exudes coastal style, a private dock with two boat slips, a detached 3-car garage with a storage loft, a spacious yard for playing and entertaining, an exquisite vantage point for enjoying the area’s natural beauty, from waterfowl to sunsets: welcome to 1100 Steamboat Road,

    Kirsten Rowan Compass

    1100 Steamboat Rd, Shady Side, MD 20764
  • /69

    $2,295,000

    • 5 Beds
    • 4.5 Baths
    • 5,151 Sq Ft

    4819 Avery Rd, Shady Side, MD 20764

    Discover unparalleled luxury in this stunning Five bedroom, four and half bath waterfront home, offering two hundred and seventy feet of private shoreline and breathtaking views. Designed for refined living and effortless entertaining, this home delivers an exceptional lifestyle both inside and out. The exterior is a private resort, featuring a heated in-ground pool, outdoor grilling area, fire

    Adam Light Monument Sotheby's International Realty

    4819 Avery Rd, 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
  • /89

    $998,850

    • 5 Beds
    • 5.5 Baths
    • 9,040 Sq Ft

    6561 Shady Side Rd, Shady Side, MD 20764

    Merchant Unmatched water views. Over 8,000 sq ft of curated living. A property that doesn’t just stand out—it stands alone.Tucked away in the quiet, rural charm of Shady Side, this architecturally bold residence offers year-round views of the West River and a lifestyle that feels worlds away—yet keeps you close to everything that matters. Step inside and you’re immediately immersed in

    Phil Gerdes Real Broker, LLC - Annapolis

    6561 Shady Side 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 effortless—yet

    Joan Stansfield Samson Properties

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

    $65,000

    • Land
    • 0.30 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., is

    Joan Stansfield Samson Properties

    1408 & 1410 Haile Pkwy, Shady Side, MD 20764
  • /11

    $177,900

    • Land
    • 0.14 Acre
    • $1,270,714 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

    Jennifer Koenig Long & Foster Real Estate, Inc.

    5250 Al Jones Dr, 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
  • /2

    $48,900

    • Land
    • 0.08 Acre
    • $611,250 per Acre

    1639 Columbia Beach Rd, Shady Side, MD 20764

    Nice, level lot ready for your dream home! Located right by Flag Pond, this property has a sewer hookup available, and the suggested building footprint is 30 ft x 40 ft. Bring your own builder and make it your own.

    Rob Schou EXP Realty, LLC

    1639 Columbia Beach Rd, Shady Side, MD 20764
  • /2

    $42,000

    • Land
    • 1.53 Acres
    • $27,451 per Acre

    6152 Shady Side Rd, Shady Side, MD 20764

    DISCOVER THIS 1.53 ACRE LOT AVAILABLE IN SHADY SIDE , MD WITHIN ANNE ARUNDEL COUNTY. ZONING R1. DRIVE BY TODAY TO DETERMINE FOR YOURSELF HOW IT CAN WORK FOR YOUR NEEDS!

    Jennifer Drennan Taylor Properties

    6152 Shady Side Rd, Shady Side, MD 20764
  • /15

    $997,000

    • Land
    • 1.60 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
  • /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
  • /2

    $100,000

    • Land
    • 1.00 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
  • /2

    $25,000

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

    0 Haile Pkwy Unit MDAA2109444, 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 MDAA2109444, 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

    Sam Tanner Keller Williams Flagship

    0 Shady Side Rd Unit MDAA2113166, Shady Side, MD 20764
  • /2

    $150,000

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

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

    Sam Tanner Keller Williams Flagship

    0 Shady Side Rd Unit MDAA2113156, Shady Side, MD 20764
  • /24

    $1,595,000 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 over 3,700 square feet of finished 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

    Lynn Peaper Hubble Bisbee Christie's International Real Estate

    5235 Al Jones Dr, Shady Side, MD 20764
  • /35

    $999,870 New Construction

    • 5 Beds
    • 4 Baths
    • 3,126 Sq Ft

    5235 Al Jones Dr, Shady Side, MD 20764

    Unique Waterfront Dream Home Opportunity at Columbia Beach – Build Your Dream Home on the Chesapeake Bay. Don't miss this rare chance to build or own waterfront Dream Home 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.,

    Rodrigo Cruz Long & Foster Real Estate, Inc.

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

    $335,000 Coming Soon

    • 2 Beds
    • 1 Bath
    • 1,060 Sq Ft

    4925 Aspen St, Shady Side, MD 20764

    Welcome Home! This adorable home hits the market next week. Professional photographs coming soon. Avalon Shores community offers a boat ramp, a pier, private beach, swimming area, & playgrounds! Quiet community with wonderful neighbors often riding bikes, golf carts or walking dogs. Enjoy the gorgeous Chesapeake Yacht Club nearby. Short distance to many restaurants and a ice cream shop!

    Jaime Rollins CENTURY 21 New Millennium

    4925 Aspen St, Shady Side, MD 20764
  • /39

    $310,000

    • 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
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