3,269

Anne Arundel, MD Homes

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  • /53

    $617,900 Under Contract

    • 4 Beds
    • 2.5 Baths
    • 3,178 Sq Ft

    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,

    Agent Photo

    Kara Leddy

    Coldwell Banker Realty

    (410) 421-7593

    4911 Lerch Dr, Shady Side, MD 20764
  • /50

    $5,000 per month

    • 5 Beds
    • 3.5 Baths
    • 3,324 Sq Ft
    • House for Rent

    5313 Dennis Point Ln, Shady Side, MD 20764

    Discover the rare opportunity to lease a fully furnished five-bedroom, three-and-a-half-bath waterfront home on exclusive Dennis Point in Shady Side—where Chesapeake Bay beauty meets refined coastal living. Surrounded by nearly 20 acres of private woodland preserve owned by the Dennis Point HOA, this exceptional property offers ultimate privacy, dramatic Bay views, and a true connection to

    GWIN HUNT TTR Sotheby's International Realty

    5313 Dennis Point Ln, 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
    • /63

      Est $462,266 Not Listed For Sale

      • 4 Beds
      • 2.5 Baths
      • 1,914 Sq Ft

      1306 Butternut St, Shady Side, MD 20764

      1306 Butternut St, Shady Side, MD 20764
  • /70

    $515,000 Pending

    • 4 Beds
    • 2.5 Baths
    • 1,756 Sq Ft

    4906 Lee Blvd, Shady Side, MD 20764

    **Move-in ready home in the private, water-privileged Westelee community of Avalon Shores**Access to beach, boat ramp, boat slips with electric, kayak rack, new waterfront playground and gazebo **Owner Suite on main level with walk in closet and private bath **Open cathedral ceilings in family room with cozy gas Fireplace and 8' double windows for abundant natural light **Hardwood floors

    Agent Photo

    Sandy Wing

    RE/MAX Leading Edge

    (443) 234-8208

    4906 Lee Blvd, Shady Side, MD 20764
  • /2

    $2,000 per month

    • 1 Bed
    • 1 Bath
    • 620 Sq Ft
    • House for Rent

    4962 Elm St, Shady Side, MD 20764

    Charming 1BR, 1BA cottage in Avalon Shores. The property has a fully fenced in backyard with lots of space and two outbuildings. One of the structures is insulated and could be used for an office.

    Zachary Wyvill RE/MAX United Real Estate

    4962 Elm St, 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
    • /30

      Est $461,453 Not Listed For Sale

      • 3 Beds
      • 2 Baths
      • 1,786 Sq Ft

      1421 Snug Harbor Rd, Shady Side, MD 20764

      1421 Snug Harbor Rd, Shady Side, MD 20764
  • /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
  • /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
    • /17

      Est $367,014 Not Listed For Sale

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

      1196 Bay View Ave, Shady Side, MD 20764

      1196 Bay View Ave, Shady Side, MD 20764
  • /49

    $465,000

    • 4 Beds
    • 2 Baths
    • 2,500 Sq Ft

    5840 Shady Side Rd, Churchton, MD 20733

    Just minutes from Franklin State Park, the West River, and the Chesapeake Bay, this 4-bedroom, 2-bath Churchton home captures the essence of relaxed coastal living. Whether you're drawn to peaceful waters, community piers, bayside dining, or quaint local shops, this location offers it all. Step inside to a spacious main level with warm wood flooring and architectural columns that subtly define

    Bob Lucido Keller Williams Lucido Agency

    5840 Shady Side Rd, Churchton, MD 20733
  • /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
    • /3

      Est $161,667 Not Listed For Sale

      1452 Shady Rest Rd, Shady Side, MD 20764

      1452 Shady Rest Rd, Shady Side, MD 20764
  • /43

    $449,900 Under Contract

    • 4 Beds
    • 2.5 Baths
    • 1,904 Sq Ft

    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
  • /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
    • /12

      Est $136,361 Not Listed For Sale

      1190 Steamboat Rd, Shady Side, MD 20764

      1190 Steamboat Rd, Shady Side, MD 20764
  • /26

    $599,900

    • 3 Beds
    • 2 Baths
    • 1,806 Sq Ft

    4727 Oak Rd, Shady Side, MD 20764

    Rare Chesapeake Bay waterfront property with panoramic views and endless potential! This 3-bedroom, 2-bath home sits on a prime waterfront lot with a private pier, spacious yard, and mature landscaping. Enjoy sweeping Bay views from the sunroom, living room, and multiple bedrooms, along with the soothing sounds of the water just steps away.The home features charming wood ceilings, exposed

    Frank Gamez REMAX Platinum Realty

    4727 Oak Rd, Shady Side, MD 20764
  • /2

    $85,000 Sold Jul 31, 2025

    • Land
    • 0.06 Acre
    • $1,416,667 per Acre
    • 68 Days On Market

    1302 Spruce St, Shady Side, MD 20764

    1302 & 1304 Spruce St lots will only be sold in conjunction together and lots need to be combined in order to build; can be done at settlement. Additional 0.11 acre lot available at 1306 Spruce Street. Storage sheds and contents on date of settlement will convey. I have confirmed with County planning and zoning that these lots together will constitute a buildable lot 50’x100’.

    Richie Taylor Taylor Properties

    1302 Spruce St, Shady Side, MD 20764
    • /39

      Est $517,218 Not Listed For Sale

      • 4 Beds
      • 2.5 Baths
      • 1,936 Sq Ft

      1220 Juniper St, Shady Side, MD 20764

      1220 Juniper St, Shady Side, MD 20764
  • /35

    $525,000

    • 3 Beds
    • 2.5 Baths
    • 1,784 Sq Ft

    1037 Biltmore Ave, West River, MD 20778

    Welcome to 1037 Biltmore Ave — A Waterfront Dream in West River!Nestled in the peaceful and picturesque community of West River, this beautifully maintained home offers the perfect blend of comfort, style, and coastal living. Just steps from the water and minutes to the Chesapeake Bay, this property is ideal for those who crave serenity without sacrificing convenience.This

    Matt Kalogeras Houwzer, LLC

    1037 Biltmore Ave, West River, MD 20778
  • /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
    • /37

      Est $458,516 Not Listed For Sale

      • 3 Beds
      • 2.5 Baths
      • 1,632 Sq Ft

      6318 Linden St, Shady Side, MD 20764

      6318 Linden St, Shady Side, MD 20764
  • /52

    $550,000

    • 3 Beds
    • 2.5 Baths
    • 2,550 Sq Ft

    5122 Marx Dr, West River, MD 20778

    Welcome to 5122 Marx Drive, nestled in the highly sought-after, water-privileged community of Cedarlea. Situated on nearly half an acre, this home features bright, open spaces with large windows and vaulted ceilings in the living room, primary bedroom, and sunroom. Arrive home to the spacious two-car garage with plenty of room for vehicles, tools, or a jet ski trailer! The main level offers a

    Tom Atwood Keller Williams Legacy

    5122 Marx Dr, West River, MD 20778
  • /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
    • /55

      Est $406,484 Not Listed For Sale

      • 3 Beds
      • 2 Baths
      • 1,200 Sq Ft

      5707 Shady Side Rd, Churchton, MD 20733

      5707 Shady Side Rd, Churchton, MD 20733
  • /29

    $554,500

    • 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
  • /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
    • /65

      Est $761,486 Not Listed For Sale

      • 3 Beds
      • 2.5 Baths
      • 3,946 Sq Ft

      5317 Birch Ct, West River, MD 20778

      5317 Birch Ct, West River, MD 20778
  • /35

    $789,000

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

    5235 Chalk Point Rd, West River, MD 20778

    Coastal Living Meets Timeless Elegance on the Chesapeake BayEscape the hustle and embrace the peaceful rhythm of coastal life in this beautifully updated 5-bedroom, 3-bath Colonial, perfectly situated on a private 1.37-acre lot in the sought-after West River community. With over 3,000 sq ft of thoughtfully designed living space, this home offers the ideal blend of comfort, flexibility,

    Bonnie O'Donnell RE/MAX One

    5235 Chalk Point Rd, West River, MD 20778
  • /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
    • /53

      Est $399,535 Not Listed For Sale

      • 3 Beds
      • 1.5 Baths
      • 1,388 Sq Ft

      1727 Columbia Beach Rd, Shady Side, MD 20764

      1727 Columbia Beach Rd, 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

    $399,000 Sold Jul 17, 2025

    • 1,027 Sq Ft
    • $389/SF
    • 40 Days On Market
    • 2 Beds
    • 2 Baths
    • Built 1940

    1215 Pine Ave, Shady Side, MD 20764

    Location, location, location! Just blocks from the sparkling Chesapeake Bay, this Shady Side gem is cute as can be and full of charm. This 2-bedroom, 2-bath home is flooded with natural light and features cathedral & vaulted ceilings, exposed beams, two brick fireplaces, and luxury vinyl plank flooring throughout. The kitchen opens up to a spacious, versatile room that can serve as a dining room

    Joan Stansfield Samson Properties

    1215 Pine Ave, Shady Side, MD 20764
    • /11

      Est $339,781 Not Listed For Sale

      • 3 Beds
      • 1 Bath
      • 864 Sq Ft

      5806 Shady Side Rd, Churchton, MD 20733

      5806 Shady Side Rd, Churchton, MD 20733
  • /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
  • /28

    $475,000 Sold Jul 11, 2025

    • 1,792 Sq Ft
    • $265/SF
    • 36 Days On Market
    • 3 Beds
    • 2 Baths
    • Built 1996

    1114 Cherry Point Rd, West River, MD 20778

    Attention all savvy buyers/investors! An exciting and improved price for these two properties. A combination of two parcels totaling 2.18 acres with private access to the wonderful South Creek. 1114 Cherry Point Road is 1.01 acres with a single family home , 3 bedrooms and 2 full bathrooms and a 2 car attached garage. Home will need a complete remodel or tear it down and build your dream

    E. Gabriela Vasco Realty Advantage of Maryland LLC

    1114 Cherry Point Rd, West River, MD 20778
    • /14

      Est $396,844 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
  • /27

    $593,100 Pending

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

    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
  • /12

    $185,000 Sold Jul 11, 2025

    • Land
    • 2.86 Acres
    • $64,685 per Acre
    • 91 Days On Market

    1344 E West Shady Side Rd, Shady Side, MD 20764

    Great price for this beautiful 2.86 acre wooded lot with deeded access to the West River! Public sewer access nearby. Short walk to Shady Side Park with ball fields / tennis court / pickleball court / basketball courts / tot lot & more! Easements and plat layout uploaded in documents / disclosures. Call listing agent for details to walk the lot and if you have any questions!

    Bill Beam Beam Realty Group, Inc.

    1344 E West Shady Side Rd, Shady Side, MD 20764

Showing Results 1 - 40, Page 1 of 18

Home Trends in Shady Side, MD

Housing Trends

Median Sale Price
$407,500
Median Single Family Sale Price
$719,935
Average Price Per Sq Ft
$301
Number of Homes for Sale
1
Last 12 months Home Sales
16
Months of Supply
0.80
Median List Price
$440,000
Median Change From 1st List Price
0%
Median Home Sale Price YoY Change
-6%
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