3,273

Shady Side, MD Homes

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    • /38

      Est $473,296 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
  • /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
  • /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
    • /22

      Est $385,363 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
  • /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
  • /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
    • /39

      Est $626,482 Not Listed For Sale

      • 4 Beds
      • 3.5 Baths
      • 2,566 Sq Ft

      1004 Hawk Channel Ct, West River, MD 20778

      1004 Hawk Channel Ct, West River, MD 20778
  • /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
  • /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
    • /23

      Est $461,227 Not Listed For Sale

      • 3 Beds
      • 2.5 Baths
      • 1,568 Sq Ft

      4961 Filbert St, Shady Side, MD 20764

      4961 Filbert St, Shady Side, MD 20764
  • /35

    $725,000

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

    5235 Chalk Point Rd, West River, MD 20778

    This spacious 5-bedroom, 3-bathroom home offers the perfect blend of comfort, convenience, and Chesapeake Bay lifestyle. Located in highly sought-after Southern Anne Arundel County, this property sits just moments from the Bay, marinas, and local seafood favorites—ideal for those who love the water and small-town living. Step inside to find a bright open layout with generous living spaces,

    Bonnie O'Donnell RE/MAX One

    5235 Chalk Point Rd, West River, MD 20778
  • /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
    • /47

      Est $1,127,919 Not Listed For Sale

      • 4 Beds
      • 3.5 Baths
      • 3,040 Sq Ft

      4816 Atwell Rd, Shady Side, MD 20764

      4816 Atwell 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
  • /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
    • /11

      Est $312,557 Not Listed For Sale

      • 3 Beds
      • 1 Bath
      • 1,166 Sq Ft

      1519 Lincoln Rd, Shady Side, MD 20764

      1519 Lincoln 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
  • /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
    • /23

      Est $516,537 Not Listed For Sale

      • 3 Beds
      • 2.5 Baths
      • 1,748 Sq Ft

      6039 Shady Side Rd, Shady Side, MD 20764

      6039 Shady Side Rd, Shady Side, MD 20764
  • /2

    $40,000

    • Land
    • 0.34 Acre
    • $117,647 per Acre

    5771 Shady Side Rd, Churchton, MD 20733

    Residential building lot awaits new owner. Sold as is .

    Joseph Butcher Long & Foster Real Estate, Inc.

    5771 Shady Side Rd, Churchton, MD 20733
  • /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
    • /20

      Est $352,335 Not Listed For Sale

      • 2 Beds
      • 1 Bath
      • 1,083 Sq Ft

      1206 Holly Ave, Shady Side, MD 20764

      1206 Holly Ave, 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
  • /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
    • /75

      Est $1,285,647 Not Listed For Sale

      • 4 Beds
      • 3 Baths
      • 2,617 Sq Ft

      1326 W River Rd, Shady Side, MD 20764

      1326 W River Rd, 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
  • /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
    • /33

      Est $460,711 Not Listed For Sale

      • 3 Beds
      • 2.5 Baths
      • 1,714 Sq Ft

      1016 Cosimano Place, West River, MD 20778

      1016 Cosimano Place, West River, MD 20778
  • /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
  • /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
    • /54

      Est $536,652 Not Listed For Sale

      • 4 Beds
      • 2.5 Baths
      • 1,870 Sq Ft

      1184 Holly Ave, Shady Side, MD 20764

      1184 Holly Ave, 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
  • /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
    • /43

      Est $462,407 Not Listed For Sale

      • 4 Beds
      • 2.5 Baths
      • 1,947 Sq Ft

      4718 Washington Ave, Shady Side, MD 20764

      4718 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
  • /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
    • /33

      Est $383,661 Not Listed For Sale

      • 2 Beds
      • 2 Baths
      • 1,285 Sq Ft

      1422 Columbia Beach Rd, Shady Side, MD 20764

      1422 Columbia Beach Rd, 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
  • /46

    $1,185,000 Sold Aug 22, 2025

    • 3,216 Sq Ft
    • $368/SF
    • 49 Days On Market
    • 4 Beds
    • 3.5 Baths
    • Built 1996

    1012 S Creek View Ct, Churchton, MD 20733

    Ideally situated on 1+ acre of land with 126 feet of South Creek waterfrontage, this stunning custom-built home is private and peaceful. The well-maintained community of South Creek View, with 32 homes, welcomes you with mature trees and landscaped yards. The private pier has 4-5 ft water depth and two boat slips, a boat lift, and a lounging platform. Located on the pristine South Creek, you are

    Reid Buckley Long & Foster Real Estate, Inc.

    1012 S Creek View Ct, Churchton, MD 20733
    • /55

      Est $406,277 Not Listed For Sale

      • 3 Beds
      • 2 Baths
      • 1,056 Sq Ft

      1509 Wright Rd, Shady Side, MD 20764

      1509 Wright Rd, Shady Side, MD 20764

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