3,275

Shady Side, MD Homes

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    • /39

      Est $640,355 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
  • /97

    $415,000

    • 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
  • /71

    $1,190,000 Sold Aug 18, 2025

    • 2,060 Sq Ft
    • $578/SF
    • 142 Days On Market
    • 3 Beds
    • 2.5 Baths
    • Built 2014

    1538 Robinson Rd, Shady Side, MD 20764

    OPEN Bay-front at this STUNNING Custom Coastal with private pier, Located in coveted Columbia Beach, this airy WATERFRONT is a head-turner, boasting an open floor-plan, with the finest of finishes! Direct Chesapeake Bay location, 100' private pier & 3 jet-ski lifts makes this the perfect retreat - or year round treat- With 3 spacious bedrooms, 2.5 beautiful baths, 9' ceilings & hickory flooring-

    Jennifer Chaney Chaney Homes, LLC

    1538 Robinson Rd, Shady Side, MD 20764
    • /23

      Est $458,544 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
  • /10

    $625,000

    • Land
    • 10.75 Acres
    • $58,140 per Acre

    5860 Shady Side Rd, Churchton, MD 20733

    WATERFRONT: Own your own park! 10+ Acres and 650+ Feet of water frontage along the South Creek in Churchton! *Do not walk the property without an appointment*

    Julie Knott Lofgren-Sargent Real Estate

    5860 Shady Side Rd, Churchton, MD 20733
  • /18

    $321,000 Sold Aug 15, 2025

    • 960 Sq Ft
    • $334/SF
    • 1 Day On Market
    • 3 Beds
    • 1 Bath
    • Built 1980

    1179 Maple Ave, Shady Side, MD 20764

    Adorable home at a great price! This home has a great wrap around deck, nice yard and 2 sheds. Just a walk away from the community area/bay. Newer frig & stove, HVAC & water softener. Hardwood floors. Great starter OR downsizer home! Don't miss out...Priced to sell !

    Tonia Parent RE/MAX Realty Group

    1179 Maple Ave, Shady Side, MD 20764
    • /47

      Est $1,109,556 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
  • /52

    $336,900

    • 2 Beds
    • 1 Bath
    • 900 Sq Ft

    1731 Columbia Beach Rd, Shady Side, MD 20764

    Just Reduced, seller says sell! Welcome to this delightful coastal cottage nestled in the heart of the Columbia Beach community! Spacious wide beach, tot lot, tennis courts and basketball too. This beautifully updated home perfectly balances modern comfort with timeless charm. Offering two spacious bedrooms and a full bath, the layout is thoughtfully designed for easy living and effortless style.

    Amy Juras Long & Foster Real Estate, Inc.

    1731 Columbia Beach Rd, Shady Side, MD 20764
  • /43

    $449,900 Sold Aug 15, 2025

    • 1,904 Sq Ft
    • $236/SF
    • 8 Days On Market
    • 4 Beds
    • 2.5 Baths
    • Built 1990

    1207 Avalon Blvd, Shady Side, MD 20764

    Welcome to this classic colonial, nestled in the desirable water-privileged community of Avalon Shores! A wide covered front porch spans the entire front of the home, creating the perfect spot to sit and unwind in the evenings and chat with neighbors, or enjoy a quiet cup of coffee. This estate sale is being sold as-is, yet the home is in solid condition, simply awaiting a few personal touches

    Mary Gatton Redfin Corp

    1207 Avalon Blvd, Shady Side, MD 20764
    • /11

      Est $315,787 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
  • /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
  • /51

    $389,000 Sold Aug 15, 2025

    • 1,407 Sq Ft
    • $276/SF
    • 21 Days On Market
    • 3 Beds
    • 1 Bath
    • Built 1940

    4977 Lerch Dr, Shady Side, MD 20764

    Discover your own slice of water-view paradise at 4977 Lerch Drive—a lovingly maintained 3-bedroom, 1-bath retreat just steps from the West River. Every corner of this home reflects the care and attention poured in by its current owner, from the bright, open-concept living spaces to the thoughtful updates throughout the interior Step inside to 1,407 sq ft of refreshed living space, where an

    Suebina Wong Douglas Realty, LLC

    4977 Lerch Dr, Shady Side, MD 20764
    • /40

      Est $631,550 Not Listed For Sale

      • 4 Beds
      • 2.5 Baths
      • 2,448 Sq Ft

      4951 Dogwood St, Shady Side, MD 20764

      4951 Dogwood St, Shady Side, MD 20764
  • /18

    $368,000

    • 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 2-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
  • /61

    $402,500 Sold Aug 11, 2025

    • 1,364 Sq Ft
    • $295/SF
    • 6 Days On Market
    • 4 Beds
    • 3 Baths
    • Built 1983

    4723 Washington Ave, Shady Side, MD 20764

    This home has it all! Updated eat in kitchen with granite counters & stainless appliances. Roof replaced within the last 10 years. HVAC replace with Trane System in 2020. 6ft tall privacy fence for your double lot rear yard with deck. Walk to the community pier & water access one block away. While home has been freshly painted. Primary suite with additional sitting area & private full bath with

    Nicki Palermo RE/MAX One

    4723 Washington Ave, Shady Side, MD 20764
    • /34

      Est $366,068 Not Listed For Sale

      • 2 Beds
      • 2 Baths
      • 864 Sq Ft

      4912 Beech St, Shady Side, MD 20764

      4912 Beech St, Shady Side, MD 20764
  • /49

    $435,000

    • 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,

    Sheri Stevens Samson Properties

    4721 Girton Ave, Shady Side, MD 20764
  • /33

    $925,000 Sold Aug 08, 2025

    • 3,445 Sq Ft
    • $269/SF
    • 127 Days On Market
    • 4 Beds
    • 2.5 Baths
    • Built 1993

    4927 Hine Dr, Shady Side, MD 20764

    Post & beam architect design home with passive solar elements and lots of glass facing the water. A beautiful waterfront lot with southern exposure and wonderful view! Very well protected water on West River, stone rip rap. Pier only a few years old. 5 feet depth at average low tide. Hop in your boat and be at one of 2 waterfront restaurants or West River Sailing Club in a couple of minutes.

    William Whitman Long & Foster Real Estate, Inc.

    4927 Hine Dr, Shady Side, MD 20764
    • /23

      Est $532,886 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
  • /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
  • /36

    $398,000 Sold Aug 07, 2025

    • 1,354 Sq Ft
    • $294/SF
    • 5 Days On Market
    • 3 Beds
    • 2 Baths
    • Built 1997

    6040 Shady Side Rd, Shady Side, MD 20764

    Charming 3-Bedroom Home in Quaint Shady Side, MDWelcome to this lovely 3-bedroom, 2 full-bath home nestled in the heart of Shady Side! Perfectly blending comfort, convenience, and outdoor charm, this well-maintained property is a rare find.Step outside to your huge fenced-in backyard, ideal for gatherings, play, or peaceful relaxation. Enjoy evenings around the cozy fire pit, or

    Theresa Mills Home Towne Real Estate

    6040 Shady Side Rd, Shady Side, MD 20764
    • /20

      Est $360,315 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
  • /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
  • /3

    $255,500 Sold Aug 05, 2025

    • 1,794 Sq Ft
    • $142/SF
    • 18 Days On Market
    • 3 Beds
    • 1 Bath
    • Built 1940

    5027 Chalk Point Rd, West River, MD 20778

    This porchfront home, located in the water-oriented community of Back Bay Beach, offers 1,794 square feet of living space and has 3 bedrooms, 1 full bathroom, spacious living room, a nice sized kitchen with appliances and a detached garage. Home is not only close to both West River and South Creek but also has easy access to piers, marina and West River Center.

    Gina Gargeu Century 21 Downtown

    5027 Chalk Point Rd, West River, MD 20778
    • /75

      Est $1,324,957 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
  • /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
  • /35

    $530,000 Sold Jul 31, 2025

    • 2,058 Sq Ft
    • $258/SF
    • 5 Days On Market
    • 4 Beds
    • 2.5 Baths
    • Built 1964

    1041 Harding Blvd, West River, MD 20778

    Single-Level Living at Its Finest! This beautifully renovated home (2021/2022) offers modern comfort and style with no detail overlooked. The upgraded kitchen features a large center island, granite countertops, white cabinetry, a double wall oven, cooktop, and recessed lighting throughout. Enjoy new flooring, custom trim work, a new furnace, new windows, and a new roof—everything has been done

    Ray Mudd Schwartz Realty, Inc.

    1041 Harding Blvd, West River, MD 20778
    • /33

      Est $456,375 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
  • /11

    $175,000

    • Land
    • 0.14 Acre
    • $1,250,000 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
  • /51

    $465,000 Sold Jul 30, 2025

    • 1,838 Sq Ft
    • $253/SF
    • 5 Days On Market
    • 3 Beds
    • 2 Baths
    • Built 1990

    4722 Oak Rd, Shady Side, MD 20764

    This charming 3 bedroom, 2 bath rancher offers 1,838 square feet of beautifully updated living space on a peaceful bay‐block lot. The layout is simple and smart—one level, no stairs, with a bright open living space, updated kitchen, and cozy bedrooms tucked away for privacy.The kitchen was fully renovated in 2018 and features a center island, plenty of counter space, and all the modern

    Jan Crowley Compass

    4722 Oak Rd, Shady Side, MD 20764
    • /28

      Est $447,280 Not Listed For Sale

      • 3 Beds
      • 1.5 Baths
      • 1,428 Sq Ft

      4912 Mariners Dr, Shady Side, MD 20764

      4912 Mariners 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
  • /26

    $530,000 Sold Jul 29, 2025

    • 1,980 Sq Ft
    • $268/SF
    • 11 Days On Market
    • 3 Beds
    • 2 Baths
    • Built 1960

    1216 Steamboat Rd, Shady Side, MD 20764

    Welcome to Shady Side on the Western bank of The Chesapeake Bay. Much more affordable than Annapolis to the north and way more relaxed and chill. All the benefits of The Chesapeake Bay and still convenient to The District, Baltimore and The Eastern Shore. We’ve just completed a thorough rehab of this wonderful rancher that sets far back off of the street and offers a 2 car detached garage, rear

    Jon Leary Cummings & Co. Realtors

    1216 Steamboat Rd, Shady Side, MD 20764
    • /54

      Est $526,342 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
  • /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
  • /44

    $420,000 Sold Jul 25, 2025

    • 1,648 Sq Ft
    • $255/SF
    • 5 Days On Market
    • 4 Beds
    • 2 Baths
    • Built 1940

    1181 Cedar Ave, Shady Side, MD 20764

    Welcome to 1181 Cedar Ave, situated in the tranquil water privileged community of Cedarhurst on the Bay! This charming home features 4 spacious bedrooms and 2 well-appointed bathrooms, offering both comfort and style. The floor plan is highlighted by an open living space right off of the kitchen area, complimented by a custom-built kitchen galley kitchen and dining area. A full bathroom is

    Ben Miller Synergy Realty

    1181 Cedar Ave, Shady Side, MD 20764
    • /33

      Est $383,701 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
  • /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
  • /41

    $2,100,000 Sold Jul 25, 2025

    • 8,412 Sq Ft
    • $250/SF
    • 96 Days On Market
    • 8 Beds
    • 8.5 Baths
    • Built 2014

    1346 E West Shady Side Rd, Shady Side, MD 20764

    MAJOR PRICE ADJUSTMENT on this incredible property! You could not build this home in this location for this amount! Located on a private 2.5-acre lot with over 300 ft of West River waterfront, 1346 E West Shady Side Road offers immediate access to the Chesapeake Bay via a private pier with lifts for jet skis and a boat. This grand home combines luxury, craftsmanship, and stunning water

    Reid Buckley Long & Foster Real Estate, Inc.

    1346 E West Shady Side Rd, Shady Side, MD 20764
    • /55

      Est $415,078 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

Showing Results 81 - 120, Page 3 of 18

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