3,275

Shady Side, MD Homes

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  • /2

    $50,000 Sold Jun 10, 2025

    • Land
    • 1 Acre
    • $50,000 per Acre
    • 135 Days On Market

    1428 Snug Harbor Rd, Shady Side, MD 20764

    Escape the hustle and bustle of city life and immerse yourself in the serene beauty of Shady Side, MD. Nestled within a picturesque landscape, this one-acre parcel of land offers a rare opportunity to create your own sanctuary surrounded by nature's bounty. Situated in the charming community of Shady Side, this property enjoys the best of both worlds – tranquility and convenience. With easy

    Joan Stansfield Samson Properties

    1428 Snug Harbor Rd, Shady Side, MD 20764
    • /103

      Est $2,138,064 Not Listed For Sale

      • 5 Beds
      • 4.5 Baths
      • 6,100 Sq Ft

      1258 W River Rd, Shady Side, MD 20764

      1258 W River Rd, Shady Side, MD 20764
  • /2

    $450,000 Coming Soon

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

    1490 Snug Harbor Rd, Shady Side, MD 20764

    Coming Soon!

    Kristi Neidhardt Northrop Realty

    1490 Snug Harbor Rd, Shady Side, MD 20764
  • /17

    $335,000 Sold May 30, 2025

    • 840 Sq Ft
    • $399/SF
    • 5 Days On Market
    • 3 Beds
    • 1 Bath
    • Built 1944

    1248 Hawthorne St, Shady Side, MD 20764

    This home shows pride of ownership, many recent upgrades, Enjoy the local beaches. marinas and dining. recently replaced roof, HVAC unit and duct work, newly installed carpet, Gravel driveway large enough for two cars and a boat. Shed with electric and multiple outlets New LG stainless steel 33 in. 26 cu. refrigerator,Beautiful level fenced yard with patio and shed.

    Terry Catalano RE/MAX Leading Edge

    1248 Hawthorne St, Shady Side, MD 20764
    • /30

      Est $467,406 Not Listed For Sale

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

      1217 Pine Ave, Shady Side, MD 20764

      1217 Pine Ave, Shady Side, MD 20764
  • /81

    $350,000 Under Contract

    • 3 Beds
    • 2 Baths
    • 968 Sq Ft

    1166 Cedar Ave, Shady Side, MD 20764

    This charming 3-bedroom, 2-bath home offers the perfect blend of comfort, style, and location! Soaring ceilings in the primary suite with a private attached full bath. Featuring an open floor plan with hardwood floors, a spacious eat-in kitchen with updated cabinets and countertops, and plenty of room to entertain, this home is move-in ready. Nestled on a sought-after double lot, you’ll have the

    Nicki Palermo RE/MAX One

    1166 Cedar Ave, Shady Side, MD 20764
  • /20

    $310,000 Sold May 30, 2025

    • 836 Sq Ft
    • $371/SF
    • 4 Days On Market
    • 2 Beds
    • 1 Bath
    • Built 1940

    4871 Avery Rd, Shady Side, MD 20764

    What an opportunity to own almost 2 acres on public sewer in Shady Side Maryland. This super cute 1940's cottage offering 2 bedrooms and 1 bath with a detached garage has so many options for a buyer. Keep it the way it is and live the tiny house lifestyle or tear it down and build a new home for your family! Zoned R1 this will allow residential This District is generally intended for

    Melanie Montague EXP Realty, LLC

    4871 Avery Rd, Shady Side, MD 20764
    • /56

      Est $612,358 Not Listed For Sale

      • 4 Beds
      • 2.5 Baths
      • 2,160 Sq Ft

      1631 Snug Harbor Rd, Shady Side, MD 20764

      1631 Snug Harbor Rd, Shady Side, MD 20764
  • /29

    $315,000 Under Contract

    • 1 Bed
    • 1 Bath
    • 620 Sq Ft

    4962 Elm St, Shady Side, MD 20764

    Charming 1BR, 1BA cottage in Avalon Shores—just a short stroll to the water! This cozy home was offers a perfect blend of comfort and convenience. Step inside to find a layout ideal for weekend getaways or year-round living. The Kitchen features stainless steel appliances and lots of counter space. The spacious fully fenced backyard is a standout, featuring two outbuildings—one perfect for a

    Zachary Wyvill RE/MAX United Real Estate

    4962 Elm St, Shady Side, MD 20764
  • /54

    $460,000 Sold May 29, 2025

    • 1,931 Sq Ft
    • $238/SF
    • 7 Days On Market
    • 3 Beds
    • 2.5 Baths
    • Built 1990

    1485 Cedarhurst Rd, Shady Side, MD 20764

    Welcome to this beautifully maintained Colonial nestled on a spacious corner lot in a peaceful cul-de-sac. Freshly painted in neutral tones, this home offers a light and airy feel throughout. The heart of the home is the stunning kitchen—featuring granite countertops, light cabinetry, and a large center island topped with butcher block, perfect for both meal prep and casual dining.Enjoy your

    Nicki Palermo RE/MAX One

    1485 Cedarhurst Rd, Shady Side, MD 20764
    • /29

      Est $348,826 Not Listed For Sale

      • 3 Beds
      • 1 Bath
      • 864 Sq Ft

      6322 Shady Side Rd, Shady Side, MD 20764

      6322 Shady Side Rd, Shady Side, MD 20764
  • /33

    $450,000 Under Contract

    • 3 Beds
    • 2.5 Baths
    • 1,392 Sq Ft

    1719 Lake Ave, Shady Side, MD 20764

    Welcome to this beautifully maintained 2-story home in the desirable waterfront community of Snug Harbor. With its inviting picket fence, covered front porch, and timeless curb appeal, this property offers the perfect blend of classic charm and modern updates. New Windows, gutters, trim, AC and water heater!!Step inside to find a bright and open floor plan designed for comfortable living and

    David Orso Berkshire Hathaway HomeServices PenFed Realty

    1719 Lake Ave, Shady Side, MD 20764
  • /4

    $11,500 Sold May 29, 2025

    • Land
    • 0.33 Acre
    • $34,848 per Acre
    • 126 Days On Market

    1209 Poplar Ave, Shady Side, MD 20764

    Located in the Cedarhurst Subdivision in Anne Arundel County just blocks away from the Chesapeake Bay. Three lots being sold together. Fantastic opportunity for a new owner. Road has yet to be built for this parcel. Buyer is responsible for conducting all due diligence on property including location, use, restrictions, and taxes. This property is now active in an online auction. All offers must

    Samuel Kim Jason Mitchell Group

    1209 Poplar Ave, Shady Side, MD 20764
    • /7

      Est $308,283 Not Listed For Sale

      • 3 Beds
      • 1 Bath
      • 864 Sq Ft

      1603 Depriest Dr, Shady Side, MD 20764

      1603 Depriest Dr, Shady Side, MD 20764
  • /19

    $329,900 Under Contract

    • 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
  • /30

    $306,000 Sold May 23, 2025

    • 704 Sq Ft
    • $435/SF
    • 2 Days On Market
    • 2 Beds
    • 1 Bath
    • Built 1930

    4854 Avery Rd, Shady Side, MD 20764

    Very rare to find an adorable little cottage located on approximately 2 acres. Newer roof, windows & doors. This one has 2 beds, 1 bath, a bright open sunroom thats perfect for a family / living room, a cute little kitchen & dining room. Full size stackable washer/dryer. Newer two zone ductless mini-split. This beauty sits on almost two acres of flat & open land backing to woods. There is a

    Vincent Damico RE/MAX Advantage Realty

    4854 Avery Rd, Shady Side, MD 20764
    • /35

      Est $385,104 Not Listed For Sale

      • 3 Beds
      • 1.5 Baths
      • 1,240 Sq Ft

      1304 Juniper St, Shady Side, MD 20764

      1304 Juniper St, Shady Side, MD 20764
  • /17

    $349,870 Under Contract

    • Land
    • 0.15 Acre
    • $2,332,467 per Acre

    5235 Al Jones Dr, Shady Side, MD 20764

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

    Rodrigo Cruz Long & Foster Real Estate, Inc.

    5235 Al Jones Dr, Shady Side, MD 20764
  • /37

    $420,000 Sold May 20, 2025

    • 1,272 Sq Ft
    • $330/SF
    • 60 Days On Market
    • 3 Beds
    • 2 Baths
    • Built 1950

    5228 Chesapeake Ave, Shady Side, MD 20764

    Charming Chesapeake Bay cottage with breathtaking water views from nearly every room! Start your mornings with a stunning sunrise from the all-season front porch. This well-maintained home features beautiful hardwood floors, new windows (2013), fresh paint (2015), and a fully encapsulated crawl space (2022). A detached garage provides extra storage. Just steps from the community beach, marina,

    Ray Mudd Schwartz Realty, Inc.

    5228 Chesapeake Ave, Shady Side, MD 20764
    • /50

      Est $605,960 Not Listed For Sale

      • 4 Beds
      • 2.5 Baths
      • 2,600 Sq Ft

      1556 Dennis Rd, Shady Side, MD 20764

      1556 Dennis Rd, Shady Side, MD 20764
  • /25

    $650,000 Under Contract

    • 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
  • /32

    $450,000 Sold May 16, 2025

    • 1,899 Sq Ft
    • $237/SF
    • 0 Days On Market
    • 4 Beds
    • 2.5 Baths
    • Built 2007

    1233 Juniper St, Shady Side, MD 20764

    Built in 2007, this Colonial equipped with 9ft ceilings is ready for you to call it "HOME!" With Quartz counters, Newer appliances and fenced in backyard. Primary suite with attached full bath, walk in closet & dual sinks. Parking is no issue with the one car garage & paved driveway. Located in a water oriented community loaded with amenities! The sandy beach with netted area for swimming, the

    Nicki Palermo RE/MAX One

    1233 Juniper St, Shady Side, MD 20764
    • /33

      Est $390,184 Not Listed For Sale

      • 3 Beds
      • 2.5 Baths
      • 1,248 Sq Ft

      4929 Chestnut St, Shady Side, MD 20764

      4929 Chestnut St, Shady Side, MD 20764
  • /11

    $185,000 Under Contract

    • Land
    • 1 Acre
    • $185,000 per Acre

    6508 Shady Side Rd, Shady Side, MD 20764

    Build your dream home! few lots like this one. Dry area, very private & wooded lot surrounded by 73 acres in conservation easement. Enjoy peaceful nature. This lot has a right of way agreement along with lot at 6512 W Shady Side Rd See attached documents and maps. Located close to the west river and community Baseball diamond and basketball courts.

    George Heine Schwartz Realty, Inc.

    6508 Shady Side Rd, Shady Side, MD 20764
  • /41

    $440,000 Sold May 12, 2025

    • 1,568 Sq Ft
    • $281/SF
    • 5 Days On Market
    • 3 Beds
    • 1.5 Baths
    • Built 1993

    1414 E West Shady Side Rd, Shady Side, MD 20764

    This charming farmhouse style home boasts an expansive front porch complete and waterviews of the Chesapeake Bay, along with unique sideline of the historic Captain Avery Museum and waterfront park just beyond! Nestled on a spacious lot with well appointed landscaping, the sizeable backyard is ideal for gardening or simply enjoying the peaceful backdrop of nearby mature trees. Stepping inside,

    Mary Gatton Redfin Corp

    1414 E West Shady Side Rd, Shady Side, MD 20764
    • /50

      Est $779,264 Not Listed For Sale

      • 3 Beds
      • 2.5 Baths
      • 1,520 Sq Ft

      4937 Thomas Dr, Shady Side, MD 20764

      4937 Thomas Dr, Shady Side, MD 20764
  • /12

    $198,000 Under Contract

    • Land
    • 1.44 Acres
    • $137,500 per Acre

    6512 Shady Side Rd, Shady Side, MD 20764

    This lot could .be yours, surrounded by nature, in conservation easement, Dry wooded lot! Build your dream home, surrounded by trees and by 73 acres in conservation easement. Next to 6508 lot, they share an easement for driveway. The best lot in the area!! Close to Baltimore, DC, and Annapolis. Located near the West River and community baseball diamond and basketball court.

    George Heine Schwartz Realty, Inc.

    6512 Shady Side Rd, Shady Side, MD 20764
  • /30

    $589,500 Sold May 09, 2025

    • 2,135 Sq Ft
    • $276/SF
    • 133 Days On Market
    • 4 Beds
    • 2.5 Baths
    • Built 2025

    4958 Filbert St, Shady Side, MD 20764

    New Construction (To-Be-Built). Meet the Monroe: this stunning home design comes with three distinct elevations to choose from, ensuring your home reflects your unique style and preferences: Traditional, Modern, or Craftsman. The spacious layout encompasses four bedrooms, Owner's suite with ensuite bathroom, and 2nd Floor laundry. Work from home effortlessly in the dedicated office space,

    Jamie Richardson RE/MAX United Real Estate

    4958 Filbert St, Shady Side, MD 20764
    • /26

      Est $280,249 Not Listed For Sale

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

      1508 Baker Rd, Shady Side, MD 20764

      1508 Baker Rd, Shady Side, MD 20764
  • /20

    $304,000 Pending

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

    4908 Aspen St, Shady Side, MD 20764

    Welcome to this 2-story home nestled in the serene Avalon Shores community. This home features 3 bedrooms, 2 full baths, and 1 half bath. Eat in kitchen with additional room for table space. The exterior boasts multi-level decks ideal for outdoor entertaining, a shady yard offering privacy, and spacious 2 car garage. Located in the peaceful Avalon Shores subdivision, this home is close to Anne

    Brenda Sarver Maryland Realty Connection

    4908 Aspen St, Shady Side, MD 20764
  • /32

    $300,000 Sold May 02, 2025

    • 950 Sq Ft
    • $316/SF
    • 15 Days On Market
    • 3 Beds
    • 1 Bath
    • Built 1940

    5215 Park Ave, Shady Side, MD 20764

    Welcome Home to 5215 Park Avenue!! This Beautifully updated Rancher has the space you need to create a life you desire! Boasting an array of sleek finishes throughout this 3 Bedroom, 1 Bathroom home has so much to offer! Featuring an open concept layout with spacious living room, kitchen, 3 entry level bedrooms, full bathroom and laundry. Kitchen boasts S/S appliances, white shaker cabinets,

    Lois Alberti Alberti Realty, LLC

    5215 Park Ave, Shady Side, MD 20764
    • /59

      Est $457,934 Not Listed For Sale

      • 3 Beds
      • 2 Baths
      • 1,600 Sq Ft

      1304 Holly St, Shady Side, MD 20764

      1304 Holly St, Shady Side, MD 20764
  • /27

    $275,000 Pending

    • 2 Beds
    • 1 Bath
    • 714 Sq Ft

    4717 Frederick Ave, Shady Side, MD 20764

    Charming coastal cottage just two blocks from the water! Welcome to 4717 Frederick Avenue, a beautifully maintained 2-bedroom, 1-bath home nestled in the serene Idlewilde on the Bay community of Shady Side. Offering water access to the West River, this updated single-level home is perfect for year-round living, a weekend getaway, or a cozy investment opportunity.Step inside to find an

    James Weiskerger Next Step Realty

    4717 Frederick Ave, Shady Side, MD 20764
  • /47

    $875,000 Sold May 02, 2025

    • 2,598 Sq Ft
    • $337/SF
    • 78 Days On Market
    • 5 Beds
    • 3 Baths
    • Built 1956

    5070 Lerch Dr, Shady Side, MD 20764

    Gorgeous waterfront home on the West River located in the Avalon Shores community of Shady Side. Offering 5 bedrooms, 3 full baths, and 2500+ sq.ft of sun-bathed living space on two levels. This beautiful home features an open floor plan with large wall of windows overlooking the rear yard and river, private pier w/ lift, mature landscaping, workshop/storage shed, and ample parking. The main

    Doc Keane Washington Fine Properties, LLC

    5070 Lerch Dr, Shady Side, MD 20764
    • /39

      Est $521,033 Not Listed For Sale

      • 3 Beds
      • 2.5 Baths
      • 1,838 Sq Ft

      1175 Maple Ave, Shady Side, MD 20764

      1175 Maple Ave, 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
  • /21

    $325,000 Sold Apr 25, 2025

    • 960 Sq Ft
    • $339/SF
    • 4 Days On Market
    • 2 Beds
    • 1 Bath
    • Built 1989

    1230 Avalon Blvd, Shady Side, MD 20764

    Welcome to this absolutely charming ranch-style home located in the highly desirable, water-privileged community of Avalon Shores. This contemporary cottage offers a cozy and inviting atmosphere, highlighted by a warm wood-burning fireplace and an open floorplan that enhances the space with cathedral ceilings, creating a bright and airy living environment.The well-sized owner’s bedroom boasts

    Patricia Frostbutter CENTURY 21 New Millennium

    1230 Avalon Blvd, Shady Side, MD 20764
    • /70

      Est $436,889 Not Listed For Sale

      • 2 Beds
      • 2 Baths
      • 1,301 Sq Ft

      4913 Lerch Dr, Shady Side, MD 20764

      4913 Lerch Dr, Shady Side, MD 20764
  • /2

    $265,000 Pending

    • 1 Bed
    • 1 Bath
    • 948 Sq Ft

    1419 Shady Rest Rd, Shady Side, MD 20764

    Cindy Martin Samson Properties

    1419 Shady Rest Rd, Shady Side, MD 20764
  • /33

    $645,000 Sold Apr 18, 2025

    • 2,868 Sq Ft
    • $225/SF
    • 28 Days On Market
    • 4 Beds
    • 2.5 Baths
    • Built 1989

    4920 Thomas Dr, Shady Side, MD 20764

    Beautifully maintained 4-bedroom, 2.5-bath home in the coveted Westelee neighborhood. This residence has everything you desire and more, including a spacious eat-in kitchen with a separate dining room, a main-level office, spa-inspired bathrooms, fresh paint, and new carpet. The upper level features a huge bonus room over the garage that can serve as a playroom or a potential 5th bedroom. Primary

    Rene Livesay Curtis Real Estate Company

    4920 Thomas Dr, Shady Side, MD 20764

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