3,281

Shady Side, MD Homes

Section Image Section Image
  • /14

    $54,900

    • Land
    • 1.53 Acres
    • $35,882 per Acre

    6152 Shady Side Rd, Shady Side, MD 20764

    1.53 Acre lot zoned R1 located in within Anne Arundel County in quiet Shady Side MD. Take a drive and see how this prime location can fulfill your needs! Owner Financing Available! Buyer to ascertain all necessary information for their intended use. Seller prefers Diana Khan of DK Law Group for Title and Closing.Property lines shown are approximate and need to be verified by purchaser.

    Agent Photo

    Kara Leddy

    Coldwell Banker Realty

    (410) 701-3561

    6152 Shady Side Rd, Shady Side, MD 20764
  • /17

    $2,595 per month

    • 3 Beds
    • 2 Baths
    • 1,344 Sq Ft
    • House for Rent

    1196 Spruce Ave, Shady Side, MD 20764

    Adorable Home in sought after Cedarhurst on the Bay. Spacious Rooms, Updated Flooring, Recently Painted, as well as recent renovation to the kitchen and baths. The front has a spacious porch to enjoy the days and evenings. Beautiful lot with a deck to boot!! This one is a must see. Community Offers Gorgeous Green Space on the Chesapeake Bay. Enjoy Community Boat Ramp, Slips, Fishing Pier,

    1196 Spruce Ave, Shady Side, MD 20764
  • /100

    $940,000 Sold Aug 29, 2025

    1015 S Creek View Ct, Churchton, MD 20733

    • 5 Beds
    • 3.5 Baths
    • 5,694 Sq Ft
    • Built 1996

    Last Sold Summary

    • $165/SF
    • 39 Days On Market

    Current Estimated Value $967,240

    Last Listing Agent Phil Gerdes Real Broker, LLC - Annapolis

    1015 S Creek View Ct, Churchton, MD 20733
    • /63

      Est $521,020 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
  • /27

    $295,000 Pending

    • 2 Beds
    • 1 Bath
    • 704 Sq Ft

    1213 Oak Ave, Shady Side, MD 20764

    A Charming Cedarhurst Cottage Near the Water - This charming 1944 cottage in Cedarhurst on the Bay offers easy coastal living and only a few houses from the Bay and the community amenities. Recent improvements within the last year include a new roof, new windows, a new hot water tank and a new water pressure tank. The kitchen has white cabinetry and there is a small laundry room with a washer and

    Agent Photo

    Bill Franklin

    Long & Foster Real Estate, Inc.

    (443) 381-0652

    1213 Oak Ave, Shady Side, MD 20764
  • /19

    $1,950 per month

    • 2 Beds
    • 1 Bath
    • 840 Sq Ft
    • House for Rent

    1359 Jordan Dr, Shady Side, MD 20764

    Freshly painted 2-story home in Avalon Shores! This charming property offers 2 bedrooms, 1 full bath, and brand-new carpet in the bedrooms. Enjoy a 10x10 deck, plus washer, dryer, and dishwasher included. Walk to the community playground, beach, pier, and boat ramp. Pets considered on a case-by-case basis. Good credit and references required.

    Lisa Magnus Clark & Co Realty, LLC

    1359 Jordan Dr, Shady Side, MD 20764
  • /65

    $710,000 Sold Aug 28, 2025

    1109 Cherry Point Rd, West River, MD 20778

    • 4 Beds
    • 4.5 Baths
    • 3,352 Sq Ft
    • Built 2011

    Last Sold Summary

    • $212/SF
    • 64 Days On Market

    Current Estimated Value $755,282

    Last Listing Agent Ray Mudd Schwartz Realty, Inc.

    1109 Cherry Point Rd, West River, MD 20778
    • /30

      Est $485,855 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
  • /49

    $425,000 Pending

    • 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
  • /26

    $2,800 per month

    • 4 Beds
    • 3 Baths
    • 2,800 Sq Ft
    • House for Rent

    6561 Shady Side Rd, Shady Side, MD 20764

    Unique rental opportunity, across the road from West River with some water views. This rental listing is for a portion of the house, which includes 4 bedrooms, 3 full baths, kitchen/dining & wood burning fireplace. Other portion of the home will be occupied only occasionally by the owners and is completely separate. There is no shared interior space. Tenants have access to the full fenced yard,

    Amelia Whitman Long & Foster Real Estate, Inc.

    6561 Shady Side Rd, Shady Side, MD 20764
  • /57

    $319,900 Sold Jan 12, 2026

    4950 W End Ave, Shady Side, MD 20764

    • 2 Beds
    • 1.5 Baths
    • 984 Sq Ft
    • Built 1950

    Last Sold Summary

    • $325/SF
    • 6 Days On Market

    Last Listing Agent Pattee McInerney Scott McInerney RE/MAX One

    4950 W End Ave, Shady Side, MD 20764
    • /35

      Est $540,796 Not Listed For Sale

      • 4 Beds
      • 2.5 Baths
      • 1,960 Sq Ft

      5031 Lerch Dr, Shady Side, MD 20764

      5031 Lerch Dr, Shady Side, MD 20764
  • /28

    $529,900

    • 3 Beds
    • 2 Baths
    • 2,024 Sq Ft

    4949 Idlewilde Rd, Shady Side, MD 20764

    This spacious and well-maintained home offers the ease of one-level living at it's best. The modern kitchen opens to a cozy family room featuring a gas fireplace and a sliding door that leads to a stunning sunroom and adjacent deck—perfect for relaxing or entertaining. Enjoy formal spaces with both a living room and dining room, along with a generous primary suite complete with a private full

    Ray Mudd Schwartz Realty, Inc.

    4949 Idlewilde Rd, Shady Side, MD 20764
  • /22

    $2,300 per month

    • 2 Beds
    • 1 Bath
    • 784 Sq Ft
    • House for Rent

    4955 Chestnut St, Shady Side, MD 20764

    Charming 2BR/1BA Cottage with Loft & Water Access in Avalon Shores! Charming cottage with white picket fencing, water access, and views of the Western River right from the driveway. The sunny foyer features wainscoting, bench seating, and storage. Enjoy an open layout with rustic hardwood floors and a cozy living area centered around a painted brick wood-stove fireplace with built-ins. An arched

    Jenna Maseritz Park Modern Realty

    4955 Chestnut St, Shady Side, MD 20764
  • /66

    $515,000 Sold Jul 08, 2025

    4726 Poplar Rd, Shady Side, MD 20764

    • 5 Beds
    • 3.5 Baths
    • 2,179 Sq Ft
    • Built 1976

    Last Sold Summary

    • $236/SF
    • 34 Days On Market

    Current Estimated Value $529,109

    Last Listing Agent Suzanne Kerill Taylor Properties

    4726 Poplar Rd, Shady Side, MD 20764
    • /17

      Est $384,402 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
  • /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
  • /7

    $1,350 per month

    • 1 Bed
    • 1 Bath
    • 700 Sq Ft
    • Condo for Rent

    1154 Steamboat Rd, Shady Side, MD 20764

    Nice upstairs apartment with private rear entrance. Unit is all electric and has its own electric meter. It includes; kitchen, living room, bedroom and full bath. It has a small deck area for tenant use and a storage shed if needed. References and application required. Credit score of 650 plus or compensating factors. No pets and no smoking in unit.

    Paul Lee Long & Foster Real Estate, Inc.

    1154 Steamboat Rd, Shady Side, MD 20764
  • /52

    $743,750 Sold Mar 28, 2025

    4922 Hine Dr, Shady Side, MD 20764

    • 4 Beds
    • 3 Baths
    • 2,268 Sq Ft
    • Built 2015

    Last Sold Summary

    • $328/SF
    • 4 Days On Market

    Current Estimated Value $754,494

    Last Listing Agent Joan Stansfield Samson Properties

    4922 Hine Dr, Shady Side, MD 20764
    • /3

      Est $94,500 Not Listed For Sale

      1452 Shady Rest Rd, Shady Side, MD 20764

      1452 Shady Rest Rd, Shady Side, MD 20764
  • /45

    $1,520,000 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’ leading luxury waterfront builder. Set within the sought-after Columbia Beach community, this coastal-style home captures the best of Chesapeake Bay living with panoramic views and the rare protection of a cove-front setting. With Whitehall, the path to building is refreshingly simple. Their step-by-step process begins with a complimentary

    Lynn Peaper Hubble Bisbee Christie's International Real Estate

    5235 Al Jones Dr, Shady Side, MD 20764
  • /13

    $2,500 per month

    • 3 Beds
    • 2 Baths
    • 1,344 Sq Ft
    • House for Rent

    6432 W Shady Side Rd, Shady Side, MD 20764

    Don't miss this rare opportunity to rent a beautifully updated home in a quiet location in Shady Side. 3 bedroom, 2 full bathrooms, and move-in ready.Plus lawn care included in rent!! Use the rent-spree link to start your application!!

    Megan Huebner Berkshire Hathaway HomeServices PenFed Realty

    6432 W Shady Side Rd, Shady Side, MD 20764
  • /3

    $33,500 Sold Jun 17, 2025

    5347 Offer Ln, Churchton, MD 20733

    • Land
    • 3.04 Acres
    • $11,020 per Acre

    Last Sold Summary

    • 24 Days On Market

    Current Estimated Value $202,333

    Last Listing Agent Luis Arrazola A.J. Billig & Company

    5347 Offer Ln, Churchton, MD 20733
    • /12

      Est $127,048 Not Listed For Sale

      1190 Steamboat Rd, Shady Side, MD 20764

      1190 Steamboat Rd, 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
  • /20

    $2,150 per month

    • 2 Beds
    • 2 Baths
    • 824 Sq Ft
    • House for Rent

    4715 Frederick Ave, Shady Side, MD 20764

    LIVE ON THE CHESAPEAKE BAY AT IDLEWILE COMMUNITY LANDLORD WILLING TO SPLIT SECURITY DEPOSIT OVER TWO MONTHS. Completely furnished and ready for Move-in! This 2-bedroom/2-bath cottage on the Chesapeake Bay features a modern kitchen with lots of natural light; the den space can function as a guest room or office. Brand new W/D, living rm rug and couch. Backyard patio lets you spread out on game day

    Angie Carr Riverscape Realty

    4715 Frederick Ave, Shady Side, MD 20764
  • /52

    $565,000 Sold Dec 05, 2025

    5122 Marx Dr, West River, MD 20778

    • 3 Beds
    • 2.5 Baths
    • 2,550 Sq Ft
    • Built 1989

    Last Sold Summary

    • $222/SF
    • 124 Days On Market

    Last Listing Agent Tom Atwood Keller Williams Legacy

    5122 Marx Dr, West River, MD 20778
    • /39

      Est $546,690 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
  • /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
  • /56

    $3,500 per month

    • 3 Beds
    • 3 Baths
    • 1,920 Sq Ft
    • House for Rent

    4922 Lerch Dr, Shady Side, MD 20764

    You can't beat the price for the WATERFRONT lifestyle in the Chesapeake Bay area! This stunning, RENOVATED open concept, 3-bedroom, 3-bath home was built in 2005 and has a PRIVATE dock -- blending modern updates, natural light, and serene water views. This home is the ideal size—not too big, not too small—offering the perfect balance of comfort, function, and privacy! Step inside an inviting

    Joan Stansfield Samson Properties

    4922 Lerch Dr, Shady Side, MD 20764
  • /20

    $600,000 Sold Sep 12, 2025

    1601 Snug Harbor Rd, Shady Side, MD 20764

    • 4 Beds
    • 2.5 Baths
    • 2,392 Sq Ft
    • Built 1999

    Last Sold Summary

    • $251/SF
    • 46 Days On Market

    Current Estimated Value $611,595

    Last Listing Agent Alex Estill Long & Foster Real Estate, Inc.

    1601 Snug Harbor Rd, Shady Side, MD 20764
    • /37

      Est $483,734 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
  • /43

    $599,990

    • 4 Beds
    • 2.5 Baths
    • 2,091 Sq Ft

    4908 Olive St, Shady Side, MD 20764

    HOME TO BE BUILT. EXISTING HOME TO BE TORN DOWN. EXPECTED SPRING/SUMMER 2026 DELIVERY. Must use builder contract - buyer responsible for 100% transfer taxes**. Schaefer Homes brings to you their latest Monroe model located in water privilege community of Westelee offering community beach, pier, playground, boat slips, boat ramp and more. Select from 3 exterior elevations! This home will come

    Ray Mudd Schwartz Realty, Inc.

    4908 Olive St, Shady Side, MD 20764
  • /3

    $255,500 Sold Aug 05, 2025

    5027 Chalk Point Rd, West River, MD 20778

    • 3 Beds
    • 1 Bath
    • 1,794 Sq Ft
    • Built 1940

    Last Sold Summary

    • $142/SF
    • 18 Days On Market

    Current Estimated Value $310,307

    Last Listing Agent Gina Gargeu Century 21 Downtown

    5027 Chalk Point Rd, West River, MD 20778
    • /65

      Est $804,858 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
  • /31

    $355,000

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

    4738 Washington Ave, Shady Side, MD 20764

    Peaceful 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 opportunity 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 natural

    Nicole Hatch Samson Properties

    4738 Washington Ave, Shady Side, MD 20764
  • /7

    $1,800,000 Sold Oct 17, 2025

    1114 Cherry Point Rd, West River, MD 20778

    • 4 Beds
    • 4.5 Baths
    • 5,757 Sq Ft
    • Built 2026

    Last Sold Summary

    • $313/SF
    • 0 Days On Market

    Last Listing Agent Michael Reible Realty Advantage of Maryland LLC

    1114 Cherry Point Rd, West River, MD 20778
    • /53

      Est $419,232 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
  • /32

    $278,500

    • 2 Beds
    • 1 Bath
    • 714 Sq Ft

    4717 Frederick Ave, Shady Side, MD 20764

    Welcome to 4717 Frederick Avenue — a charming and updated cottage just two blocks from the West River in the Idlewilde on the Bay community. This 2-bedroom, 1-bath ranch-style home offers comfortable one-level living with thoughtful improvements throughout. Step inside to a bright, open living area featuring neutral finishes and a cozy fireplace, ideal for everyday relaxation. The renovated

    James Weiskerger Next Step Realty

    4717 Frederick Ave, Shady Side, MD 20764
  • /2

    $149,000 Sold Apr 18, 2025

    6101 Shady Side Rd, Shady Side, MD 20764

    • 2 Beds
    • 1 Bath
    • 712 Sq Ft
    • Built 1935

    Last Sold Summary

    • $209/SF
    • 11 Days On Market

    Current Estimated Value $178,604

    Last Listing Agent Joan Stansfield Samson Properties

    6101 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
$421,250
Median Single Family Sale Price
$420,000
Average Price Per Sq Ft
$310
Number of Homes for Sale
21
Last 12 months Home Sales
96
Months of Supply
2.60
Median List Price
$421,250
Median Change From 1st List Price
0%
Median Home Sale Price YoY Change
9%
How to Buy a Home How to Finance a Home How to Sell a Home