3,275

Shady Side, MD Homes

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  • /42

    $450,000 Sold Sep 19, 2025

    • 2,464 Sq Ft
    • $183/SF
    • 16 Days On Market
    • 4 Beds
    • 2.5 Baths
    • Built 1968

    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
    • /14

      Est $420,467 Not Listed For Sale

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

      1437 Cedarhurst Rd, Shady Side, MD 20764

      1437 Cedarhurst Rd, Shady Side, MD 20764
  • /35

    $749,000

    • 5 Beds
    • 3 Baths
    • 3,052 Sq Ft

    5235 Chalk Point Rd, West River, MD 20778

    Spacious and updated 5-bedroom, 3-bath home located in the desirable South County area near the Chesapeake Bay. This property features numerous recent improvements including a fully updated kitchen, refreshed vanities, new paint, new appliances, upgraded flooring, and central AC.The home offers multiple living areas, a generous primary suite, and ample space for family, guests, or a home

    Bonnie O'Donnell RE/MAX One

    5235 Chalk Point Rd, West River, MD 20778
  • /10

    $450,000 Sold Sep 19, 2025

    • 862 Sq Ft
    • $522/SF
    • 351 Days On Market
    • 2 Beds
    • 1 Bath
    • Built 1930

    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

    Bruce Thompson Long & Foster Real Estate, Inc.

    1337 W River Rd, Shady Side, MD 20764
    • /53

      Est $348,463 Not Listed For Sale

      • 3 Beds
      • 1 Bath
      • 1,182 Sq Ft

      1728 Maryland Ave, Shady Side, MD 20764

      1728 Maryland Ave, 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
  • /20

    $600,000 Sold Sep 12, 2025

    • 2,392 Sq Ft
    • $251/SF
    • 46 Days On Market
    • 4 Beds
    • 2.5 Baths
    • Built 1999

    1601 Snug Harbor Rd, Shady Side, MD 20764

    Charming and spacious colonial, situated on nearly 2 picturesque acres in Shady Side. Boasting 4 bedrooms and 2.5 bathrooms, this lovely home features a formal dining room, a spacious family room with a fireplace, and large sitting rooms off to the side, a finely appointed kitchen with granite counters and SS appliances, a large addition off the back of the home with vaulted ceilings and wood

    Alex Estill Long & Foster Real Estate, Inc.

    1601 Snug Harbor Rd, Shady Side, MD 20764
    • /34

      Est $816,311 Not Listed For Sale

      • 4 Beds
      • 2.5 Baths
      • 3,143 Sq Ft

      5268 Chalk Point Rd, West River, MD 20778

      5268 Chalk Point Rd, West River, MD 20778
  • /31

    $360,000

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

    4738 Washington Ave, Shady Side, MD 20764

    Easy 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

    Nicole Hatch Samson Properties

    4738 Washington Ave, Shady Side, MD 20764
  • /34

    $400,000 Sold Sep 05, 2025

    • 1,120 Sq Ft
    • $357/SF
    • 1 Day On Market
    • 3 Beds
    • 2 Baths
    • Built 1989

    1228 Avalon Blvd, Shady Side, MD 20764

    Welcome to 1228 Avalon Boulevard, where top-tier renovations meet thoughtful design in every detail. From the moment you arrive, you'll appreciate the newly expanded driveway offering ample parking, complemented by a new paver walkway, meticulous landscaping, and a beautifully stained front deck.Step inside to an open-concept floor plan featuring brand new luxury vinyl plank flooring that

    Terry McAllister RE/MAX One

    1228 Avalon Blvd, Shady Side, MD 20764
    • /52

      Est $540,849 Not Listed For Sale

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

      4907 Magnolia St, Shady Side, MD 20764

      4907 Magnolia St, Shady Side, MD 20764
  • /5

    $145,000

    • Land
    • 0.17 Acre
    • $852,941 per Acre

    5314 Al Jones Dr, Shady Side, MD 20764

    Beautiful Chesapeake Bay property for sale! Don’t miss this rare opportunity to build your dream home in the quaint, gated community of Columbia Beach, a serene neighborhood offering breathtaking bay views. Enjoy coastal living with a private pier, boat ramp, playground, tennis and basketball courts, and pickleball. Perfect for boating, fishing, sailing, kayaking, or simply relaxing by the

    Niesha Thomas NextHome Mims Realty Group

    5314 Al Jones Dr, Shady Side, MD 20764
  • /34

    $335,000 Sold Sep 04, 2025

    • 1,060 Sq Ft
    • $316/SF
    • 3 Days On Market
    • 2 Beds
    • 1 Bath
    • Built 1989

    4925 Aspen St, Shady Side, MD 20764

    Enjoy coastal living without the high price in Avalon Shores. This water-oriented community offers boat ramp, a pier, private beaches, swimming area, & playgrounds. Quiet community with wonderful neighbors often riding bikes, golf carts or walking dogs. 2 bedrooms, 1 bath with addition off the master bedroom that would make the perfect office, exercise room or nursey. Kitchen updated, new

    Jaime Rollins CENTURY 21 New Millennium

    4925 Aspen St, Shady Side, MD 20764
    • /35

      Est $352,598 Not Listed For Sale

      • 2 Beds
      • 1 Bath
      • 840 Sq Ft

      1311 Holly St, Shady Side, MD 20764

      1311 Holly St, Shady Side, MD 20764
  • /26

    $449,950

    • 3 Beds
    • 2.5 Baths
    • 1,332 Sq Ft

    1250 Juniper St, Shady Side, MD 20764

    Amazing opportunity to own a home in the Avalon Shores community of Shady Side. The waterfront community offers a beach, boat ramp, 2 playgrounds and a baseball field.The house is well kept and move-in ready. The interior has been freshly painted, Recent improvements include the new appliances, roof, HVAC system and window blinds. The house also features indoor and outdoor speakers with

    Ronald Watson Flag Real Estate Inc.

    1250 Juniper St, Shady Side, MD 20764
  • /27

    $565,000 Sold Sep 04, 2025

    • 1,152 Sq Ft
    • $490/SF
    • 69 Days On Market
    • 3 Beds
    • 1.5 Baths
    • Built 1985

    1605 Depriest Dr, Shady Side, MD 20764

    PURCHASE THIS BEAUTIFUL MOVE - IN READY HOME WITH 2 ATTACHED LOTS!! Incredible peninsula location with 180 degree WATER VIEWS of the Chesapeake Bay in the historical gated community of Columbia Beach in Shady Side , Maryland. This 2 level 3B/1.5 BA home is the perfect WEEKEND RETREAT and/or full time YEAR ROUND MAIN RESIDENCE. Great home to work remotely from and also a great location

    Lydia Newman Fairfax Realty Premier

    1605 Depriest Dr, Shady Side, MD 20764
    • /67

      Est $846,223 Not Listed For Sale

      • 6 Beds
      • 3.5 Baths
      • 2,918 Sq Ft

      629 Plantation Blvd, West River, MD 20778

      629 Plantation Blvd, West River, MD 20778
  • /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
  • /63

    $1,650,000 Sold Sep 03, 2025

    • 4,109 Sq Ft
    • $402/SF
    • 9 Days On Market
    • 5 Beds
    • 3 Baths
    • Built 1994

    1471 Nieman Rd, Shady Side, MD 20764

    Waterfront Paradise with Breathtaking Chesapeake Bay Views Welcome to your private waterfront retreat, nestled on a serene point along the West River with sweeping, panoramic views of the Chesapeake Bay. Just one hour from Washington, DC and without the hassle of crossing the Bay Bridge, this immaculate 5-bedroom, 3-bathroom home offers over 4,100 square feet of updated living space and

    Chris Craddock EXP Realty, LLC

    1471 Nieman Rd, Shady Side, MD 20764
    • /77

      Est $494,353 Not Listed For Sale

      • 4 Beds
      • 2.5 Baths
      • 2,064 Sq Ft

      1207 Juniper St, Shady Side, MD 20764

      1207 Juniper St, 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
  • /38

    $390,000 Sold Aug 29, 2025

    • 1,340 Sq Ft
    • $291/SF
    • 15 Days On Market
    • 3 Beds
    • 1.5 Baths
    • Built 1992

    1334 Jordan Dr, Shady Side, MD 20764

    Welcome to 1334 Jordan Drive, an adorably updated home nestled in the coveted waterfront community of Avalon Shores. With the perfect blend of modern elegance and functional design, this property offers a wonderful living experience. Gorgeous flooring flows seamlessly throughout, setting the stage for a home that exudes both warmth and sophistication. Walking in the front door you'll find an

    Susanne Modica Anne Arundel Properties, Inc.

    1334 Jordan Dr, Shady Side, MD 20764
    • /18

      Est $329,133 Not Listed For Sale

      • 2 Beds
      • 1 Bath
      • 960 Sq Ft

      1505 Baker Rd, Shady Side, MD 20764

      1505 Baker Rd, Shady Side, MD 20764
  • /19

    $441,000

    • 4 Beds
    • 2 Baths
    • 1,248 Sq Ft

    1520 Lincoln Rd, Shady Side, MD 20764

    Great Cape Cod on 4 lots with nice upgrades in beautiful gated beach community. Photos coming soon.

    Lydia Newman Fairfax Realty Premier

    1520 Lincoln Rd, Shady Side, MD 20764
  • /100

    $940,000 Sold Aug 29, 2025

    • 5,694 Sq Ft
    • $165/SF
    • 39 Days On Market
    • 5 Beds
    • 3.5 Baths
    • Built 1996

    1015 S Creek View Ct, Churchton, MD 20733

    Some homes impress you with features. This one leaves you with a feeling: luxury, elegance, features, form, utility, and most of all—home.Hidden in its own oasis of a quiet cul-de-sac, this home opens to sweeping, year-round water views—sunrises casting light across its front, golden-hour sunsets melting into the trees behind. It’s the kind of place that gives you permission to slow down

    Phil Gerdes Real Broker, LLC - Annapolis

    1015 S Creek View Ct, Churchton, MD 20733
    • /13

      Est $319,095 Not Listed For Sale

      • 2 Beds
      • 1 Bath
      • 576 Sq Ft

      5326 Al Jones Dr, Shady Side, MD 20764

      5326 Al Jones Dr, Shady Side, MD 20764
  • /6

    $375,000

    • 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
  • /21

    $370,000 Sold Aug 29, 2025

    • 1,100 Sq Ft
    • $336/SF
    • 47 Days On Market
    • 3 Beds
    • 2.5 Baths
    • Built 1992

    1216 Hawthorne St, Shady Side, MD 20764

    Move-In Ready Coastal Gem in Shady Side – No HOA, Big Yard, and Modern Upgrades!Tucked away in a peaceful, water-oriented community just minutes from the Chesapeake Bay, this 3-bedroom, 2.5-bathroom home offers the perfect blend of charm and convenience. Enjoy recent updates including a new HVAC system, water heater, well pump & softener, electrical upgrades, and fresh paint — plus stylish

    TJ Alves Cummings & Co. Realtors

    1216 Hawthorne St, Shady Side, MD 20764
    • /58

      Est $644,423 Not Listed For Sale

      • 3 Beds
      • 2 Baths
      • 1,534 Sq Ft

      4931 Idlewilde Rd, Shady Side, MD 20764

      4931 Idlewilde Rd, Shady Side, MD 20764
  • /9

    $90,000

    • Land
    • 1.02 Acres
    • $88,235 per Acre

    5277 Cedar St, West River, MD 20778

    Beautiful 1 acre property in the heart of Shady Side! This is an amazing opportunity for anyone looking to build their dream home in a nice secluded area with views of trees! The land is located down a gravel driveway way off the main road for maximum privacy. This is a one of a kind opportunity to build the home you've always wanted!

    Michael Frank EXP Realty, LLC

    5277 Cedar St, West River, MD 20778
  • /65

    $710,000 Sold Aug 28, 2025

    • 3,352 Sq Ft
    • $212/SF
    • 64 Days On Market
    • 4 Beds
    • 4.5 Baths
    • Built 2011

    1109 Cherry Point Rd, West River, MD 20778

    First time on the market! This custom-built water view home, set on a picturesque one-acre lot, was thoughtfully designed by its original owners. Featuring a first-floor primary suite, wide hallways and doors for wheelchair accessibility, and a roll-in shower in the primary bath, every detail was carefully planned. The exquisite gourmet kitchen boasts a commercial gas stove, wall oven, spacious

    Ray Mudd Schwartz Realty, Inc.

    1109 Cherry Point Rd, West River, MD 20778
    • /42

      Est $375,927 Not Listed For Sale

      • 2 Beds
      • 1 Bath
      • 800 Sq Ft

      4737 Chesapeake Ave, Shady Side, MD 20764

      4737 Chesapeake Ave, 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
  • /33

    $450,000 Sold Aug 27, 2025

    • 2,296 Sq Ft
    • $196/SF
    • 2 Days On Market
    • 5 Beds
    • 2 Baths
    • Built 1999

    1027 Biltmore Ave, West River, MD 20778

    Beautiful 5-Bedroom Home on One of the Largest Lots in the Community! This spacious and well-maintained home sits on an expansive lot and features a fully fenced backyard—perfect for entertaining or relaxing with family. Enjoy the large 2-year-old patio complete with a built-in fire pit and take comfort in the recently installed underground French drain system throughout the rear yard, designed

    Ray Mudd Schwartz Realty, Inc.

    1027 Biltmore Ave, West River, MD 20778
    • /38

      Est $479,637 Not Listed For Sale

      • 3 Beds
      • 2 Baths
      • 1,824 Sq Ft

      1195 Bayview Ave, Shady Side, MD 20764

      1195 Bayview Ave, 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
  • /53

    $617,900 Sold Aug 27, 2025

    • 3,178 Sq Ft
    • $194/SF
    • 26 Days On Market
    • 4 Beds
    • 2.5 Baths
    • Built 2005

    4911 Lerch Dr, Shady Side, MD 20764

    Get ready to discover your Dream Home on the peaceful Shady Side Peninsula! A Welcoming and Spacious Colonial has hit the market, perfectly situated on a desirable Corner Lot within the serene, Water-oriented Community of Avalon Shores.This impressive 4-bedroom, 2.5 bath residence offers an idyllic Chesapeake Bay Lifestyle, just a few blocks from the community's private beach, playgrounds,

    Kara Leddy Coldwell Banker Realty

    4911 Lerch Dr, Shady Side, MD 20764
    • /22

      Est $391,879 Not Listed For Sale

      • 3 Beds
      • 2 Baths
      • 1,120 Sq Ft

      1170 Maple Ave, Shady Side, MD 20764

      1170 Maple Ave, Shady Side, MD 20764
  • /39

    $429,000

    • 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
  • /77

    $800,000 Sold Aug 25, 2025

    • 2,918 Sq Ft
    • $274/SF
    • 0 Days On Market
    • 6 Beds
    • 3.5 Baths
    • Built 1992

    5312 Beauvoir Ct, West River, MD 20778

    Welcome to West River Estates—one of South County's most coveted waterfront communities!Step into your own private backyard paradise, featuring a saltwater pool with a jumping rock waterfall, dual patios, and a Trex deck—perfect for soaking up the sun or entertaining under the stars. The flat, fully fenced yard backs to peaceful woods, offering a serene setting with plenty of space for

    Dawn Marie Miller Coldwell Banker Realty

    5312 Beauvoir Ct, West River, MD 20778

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