3,279

Shady Side, MD Homes

Section Image
  • 5227 Al Jones Dr, Shady Side, MD 20764
    5227 Al Jones Dr, Shady Side, MD 20764
    5227 Al Jones Dr, Shady Side, MD 20764
    /18

    $414,900

    Sold Jun 24, 2025

    5227 Al Jones Dr, Shady Side, MD 20764

    • 3 Beds
    • 2 Baths
    • 1,269 Sq Ft
    • Built 1940

    Last Sold Summary

    • $327/SF
    • 3 Days On Market

    Current Estimated Value $441,233

    Last Listing Agent Lydia Newman Corner House Realty

    5227 Al Jones Dr, Shady Side, MD 20764
    • 1727 Columbia Beach Rd, Shady Side, MD 20764
      1727 Columbia Beach Rd, Shady Side, MD 20764
      1727 Columbia Beach Rd, Shady Side, MD 20764
      /53

      Est $398,744

      Not Listed For Sale

      1727 Columbia Beach Rd, Shady Side, MD 20764

      • 3 Beds
      • 1.5 Baths
      • 1,388 Sq Ft
      • Built 1958
      1727 Columbia Beach Rd, Shady Side, MD 20764

      Last Sold Summary

      • 1 Day On Market

  • 4909 Olive St, Shady Side, MD 20764
    4909 Olive St, Shady Side, MD 20764
    4909 Olive St, Shady Side, MD 20764
    /40

    $499,900

    • 3 Beds
    • 2.5 Baths
    • 1,848 Sq Ft

    4909 Olive St, Shady Side, MD 20764

    Welcome to 4909 Olive Street, a newer construction three bedroom, two and a half bath home in the waterfront community of Avalon Shores. Offering a functional layout, contemporary finishes, open living spaces, a fully fenced in backyard, and a private driveway. Avalon Shores residents enjoy access to a community beach, fishing pier, boat ramp, kayak launch, waterfront park, playground, basketball

    Erica Baker TTR Sotheby's International Realty

    4909 Olive St, Shady Side, MD 20764
  • 4913 Chestnut St, Shady Side, MD 20764
    4913 Chestnut St, Shady Side, MD 20764
    4913 Chestnut St, Shady Side, MD 20764
    /30

    $347,000

    Sold Dec 08, 2025

    4913 Chestnut St, Shady Side, MD 20764

    • 3 Beds
    • 2 Baths
    • 1,152 Sq Ft
    • Built 1989

    Last Sold Summary

    • $301/SF
    • 23 Days On Market

    Current Estimated Value $358,503

    Last Listing Agent Ray Mudd Schwartz Realty, Inc.

    4913 Chestnut St, Shady Side, MD 20764
    • 5207 Nick Rd, Shady Side, MD 20764
      5207 Nick Rd, Shady Side, MD 20764
      5207 Nick Rd, Shady Side, MD 20764
      /42

      Est $427,003

      Not Listed For Sale

      5207 Nick Rd, Shady Side, MD 20764

      • 4 Beds
      • 2 Baths
      • 1,320 Sq Ft
      • Built 1996
      5207 Nick Rd, Shady Side, MD 20764

      Last Sold Summary

      • 44 Days On Market

  • 1316 Juniper St, Shady Side, MD 20764
    1316 Juniper St, Shady Side, MD 20764
    1316 Juniper St, Shady Side, MD 20764
    /41

    $569,900

    New Construction
    • 4 Beds
    • 2.5 Baths
    • 1,949 Sq Ft

    1316 Juniper St, Shady Side, MD 20764

    This Stylish New home is move in ready and just in time to enjoy the summer breezes at the community Beach areas and play grounds! It is ready for your personal touch to make it your own! Main level features include Luxury Vinyl Plank flooring, 9' ceilings, Luxury kitchen with granite countertops, stainless steel appliances accented with sleek white cabinets with soft close drawers and a center

    Paul Lee Long & Foster Real Estate, Inc.

    1316 Juniper St, Shady Side, MD 20764
  • 5235 Chalk Point Rd, West River, MD 20778
    5235 Chalk Point Rd, West River, MD 20778
    5235 Chalk Point Rd, West River, MD 20778
    /69

    $699,000

    Sold May 14, 2026

    5235 Chalk Point Rd, West River, MD 20778

    • 5 Beds
    • 3 Baths
    • 3,052 Sq Ft
    • Built 1990

    Last Sold Summary

    • $229/SF
    • 22 Days On Market

    Current Estimated Value $718,456

    Last Listing Agent Karleen Monday Peninsula Properties, LLC.

    5235 Chalk Point Rd, West River, MD 20778
    • 4933 Aspen St, Shady Side, MD 20764
      4933 Aspen St, Shady Side, MD 20764
      4933 Aspen St, Shady Side, MD 20764
      /38

      Est $735,590

      Not Listed For Sale

      4933 Aspen St, Shady Side, MD 20764

      • 4 Beds
      • 3.5 Baths
      • 3,613 Sq Ft
      • Built 2008
      4933 Aspen St, Shady Side, MD 20764

      Last Sold Summary

      • 81 Days On Market

  • 4908 Olive St, Shady Side, MD 20764
    4908 Olive St, Shady Side, MD 20764
    4908 Olive St, Shady Side, MD 20764
    /44

    $599,990

    New Construction Under Contract
    • 4 Beds
    • 2.5 Baths
    • 2,091 Sq Ft

    4908 Olive St, Shady Side, MD 20764

    5/16/26 Under roof and ready for drywall. EXPECTED JULY 2026 DELIVERY. 100% financing available with USDA loan. $10k. closing assistance with use of preferred lender and title company. 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,

    Ray Mudd Schwartz Realty, Inc.

    4908 Olive St, Shady Side, MD 20764
  • 1179 Maple Ave, Shady Side, MD 20764
    1179 Maple Ave, Shady Side, MD 20764
    1179 Maple Ave, Shady Side, MD 20764
    /18

    $321,000

    Sold Aug 15, 2025

    1179 Maple Ave, Shady Side, MD 20764

    • 3 Beds
    • 1 Bath
    • 960 Sq Ft
    • Built 1980

    Last Sold Summary

    • $334/SF
    • 1 Day On Market

    Current Estimated Value $339,202

    Last Listing Agent Tonia Parent RE/MAX United Real Estate

    1179 Maple Ave, Shady Side, MD 20764
    • 1728 Maryland Ave, Shady Side, MD 20764
      1728 Maryland Ave, Shady Side, MD 20764
      1728 Maryland Ave, Shady Side, MD 20764
      /53

      Est $325,548

      Not Listed For Sale

      1728 Maryland Ave, Shady Side, MD 20764

      • 3 Beds
      • 1 Bath
      • 1,182 Sq Ft
      • Built 1954
      1728 Maryland Ave, Shady Side, MD 20764

      Last Sold Summary

      • 61 Days On Market

  • 1222 Juniper St, Shady Side, MD 20764
    1222 Juniper St, Shady Side, MD 20764
    1222 Juniper St, Shady Side, MD 20764
    /32

    $479,990

    $20K PRICE DROP Pending
    • 3 Beds
    • 2.5 Baths
    • 1,598 Sq Ft

    1222 Juniper St, Shady Side, MD 20764

    Would you love to live in a water oriented community? Have you ever? Come take a look at this year 2020 built 3 bedroom 2.5 bathroom home located in the AVALON SHORES community surrounded by the beautiful Chesapeake Bay and tributaries. Avalon Shores has wonderful neighborhood amenities including play areas, beach and boat launch . Come see this traditional home with an open floor plan. Plenty of

    Jesse Hoffman HomeSmart

    1222 Juniper St, Shady Side, MD 20764
  • 1037 Biltmore Ave, West River, MD 20778
    1037 Biltmore Ave, West River, MD 20778
    1037 Biltmore Ave, West River, MD 20778
    /43

    $466,000

    Sold Jan 12, 2026

    1037 Biltmore Ave, West River, MD 20778

    • 3 Beds
    • 2.5 Baths
    • 1,784 Sq Ft
    • Built 2000

    Last Sold Summary

    • $261/SF
    • 8 Days On Market

    Current Estimated Value $470,548

    Last Listing Agent Dawn Marie Miller Coldwell Banker Realty

    1037 Biltmore Ave, West River, MD 20778
    • 5268 Chalk Point Rd, West River, MD 20778
      5268 Chalk Point Rd, West River, MD 20778
      5268 Chalk Point Rd, West River, MD 20778
      /34

      Est $857,230

      Not Listed For Sale

      5268 Chalk Point Rd, West River, MD 20778

      • 4 Beds
      • 2.5 Baths
      • 3,143 Sq Ft
      • Built 2006
      5268 Chalk Point Rd, West River, MD 20778

      Last Sold Summary

      • 230 Days On Market

  • 1428 Haile Pkwy, Shady Side, MD 20764
    1428 Haile Pkwy, Shady Side, MD 20764
    /2

    $39,000

    Pending
    • Land
    • 9,147 Sq Ft
    • $185,714 per Acre

    1428 Haile Pkwy, Shady Side, MD 20764

    Stacey Gembicki Berkshire Hathaway HomeServices PenFed Realty

    1428 Haile Pkwy, Shady Side, MD 20764
  • 1223 Pine Ave, Shady Side, MD 20764
    1223 Pine Ave, Shady Side, MD 20764
    /2

    $315,000

    Sold Jun 15, 2026

    1223 Pine Ave, Shady Side, MD 20764

    • 2 Beds
    • 1 Bath
    • 960 Sq Ft
    • Built 1940

    Last Sold Summary

    • 3% Below List Price
    • $328/SF
    • 9 Days On Market

    Current Estimated Value $318,920

    Last Listing Agent Ryan Hutchins Hutchins Properties

    1223 Pine Ave, Shady Side, MD 20764
    • 4907 Magnolia St, Shady Side, MD 20764
      4907 Magnolia St, Shady Side, MD 20764
      4907 Magnolia St, Shady Side, MD 20764
      /52

      Est $531,240

      Not Listed For Sale

      4907 Magnolia St, Shady Side, MD 20764

      • 4 Beds
      • 2.5 Baths
      • 2,160 Sq Ft
      • Built 2008
      4907 Magnolia St, Shady Side, MD 20764

      Last Sold Summary

      • 6 Days On Market

  • 4950 Bonniewood Dr, Shady Side, MD 20764
    4950 Bonniewood Dr, Shady Side, MD 20764
    4950 Bonniewood Dr, Shady Side, MD 20764
    /73

    $795,000

    • 3 Beds
    • 2 Baths
    • 2,304 Sq Ft

    4950 Bonniewood Dr, Shady Side, MD 20764

    Waterfront living with a private dock—all for under $800,000! Nestled in the charming Avalon Shores community, this beautifully updated coastal home perfectly blends classic elegance with modern comfort. The open-concept layout features two distinct living areas, ideal for both entertaining and daily relaxation. At the heart of the home is a premium kitchen equipped with granite countertops,

    Jamie Angichiodo RE/MAX Leading Edge

    4950 Bonniewood Dr, Shady Side, MD 20764
  • 4717 Frederick Ave, Shady Side, MD 20764
    4717 Frederick Ave, Shady Side, MD 20764
    4717 Frederick Ave, Shady Side, MD 20764
    /32

    $274,000

    Sold Feb 23, 2026

    4717 Frederick Ave, Shady Side, MD 20764

    • 2 Beds
    • 1 Bath
    • 714 Sq Ft
    • Built 1920

    Last Sold Summary

    • 5% Below List Price
    • $384/SF
    • 59 Days On Market

    Current Estimated Value $277,313

    Last Listing Agent James Weiskerger Next Step Realty

    4717 Frederick Ave, Shady Side, MD 20764
    • 1311 Holly St, Shady Side, MD 20764
      1311 Holly St, Shady Side, MD 20764
      1311 Holly St, Shady Side, MD 20764
      /35

      Est $354,950

      Not Listed For Sale

      1311 Holly St, Shady Side, MD 20764

      • 2 Beds
      • 1 Bath
      • 840 Sq Ft
      • Built 1989
      1311 Holly St, Shady Side, MD 20764

      Last Sold Summary

      • 0 Days On Market

  • 4721 Oak Rd, Shady Side, MD 20764
    4721 Oak Rd, Shady Side, MD 20764
    4721 Oak Rd, Shady Side, MD 20764
    /59

    $1,160,000

    • 4 Beds
    • 3 Baths
    • 1,868 Sq Ft

    4721 Oak Rd, Shady Side, MD 20764

    Welcome to 4721 Oak Road, your waterfront paradise on the Chesapeake Bay! Nestled in the sought-after Felicity Cove community of Shady Side, this custom-built 2014 coastal home seamlessly blends modern luxury with effortless waterfront living. Boasting 4 spacious bedrooms, 3 full bathrooms, and 1,868 square feet of pristine living space, this residence shows like new. Step inside to an

    Angie Carr Riverscape Realty

    4721 Oak Rd, Shady Side, MD 20764
  • 1457 Nieman Rd, Shady Side, MD 20764
    1457 Nieman Rd, Shady Side, MD 20764
    1457 Nieman Rd, Shady Side, MD 20764
    /61

    $1,500,000

    Sold Nov 14, 2025

    1457 Nieman Rd, Shady Side, MD 20764

    • 5 Beds
    • 4 Baths
    • 3,064 Sq Ft
    • Built 2006

    Last Sold Summary

    • $490/SF
    • 4 Days On Market

    Current Estimated Value $1,489,521

    Last Listing Agent Doc Keane Washington Fine Properties, LLC

    1457 Nieman Rd, Shady Side, MD 20764
    • 629 Plantation Blvd, West River, MD 20778
      629 Plantation Blvd, West River, MD 20778
      629 Plantation Blvd, West River, MD 20778
      /67

      Est $778,756

      Not Listed For Sale

      629 Plantation Blvd, West River, MD 20778

      • 6 Beds
      • 3.5 Baths
      • 2,918 Sq Ft
      • Built 1992
      629 Plantation Blvd, West River, MD 20778

      Last Sold Summary

      • 41 Days On Market

  • 5250 Al Jones Dr, Shady Side, MD 20764
    5250 Al Jones Dr, Shady Side, MD 20764
    5250 Al Jones Dr, Shady Side, MD 20764
    /11

    $149,999

    • Land
    • 6,098 Sq Ft
    • $1,071,421 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 can

    Jennifer Koenig Long & Foster Real Estate, Inc.

    5250 Al Jones Dr, Shady Side, MD 20764
  • 1510 Callaway Dr, Shady Side, MD 20764
    1510 Callaway Dr, Shady Side, MD 20764
    1510 Callaway Dr, Shady Side, MD 20764
    /63

    $500,000

    Sold May 28, 2026

    1510 Callaway Dr, Shady Side, MD 20764

    • 4 Beds
    • 2 Baths
    • 2,074 Sq Ft
    • Built 1940

    Last Sold Summary

    • 4% Above List Price
    • $241/SF
    • 2 Days On Market

    Current Estimated Value $474,983

    Last Listing Agent Dave Luptak Long & Foster Real Estate, Inc.

    1510 Callaway Dr, Shady Side, MD 20764
    • 1501 Garst Rd, Shady Side, MD 20764
      1501 Garst Rd, Shady Side, MD 20764
      1501 Garst Rd, Shady Side, MD 20764
      /50

      Est $302,225

      Not Listed For Sale

      1501 Garst Rd, Shady Side, MD 20764

      • 2 Beds
      • 1 Bath
      • 680 Sq Ft
      • Built 1965
      1501 Garst Rd, Shady Side, MD 20764

      Last Sold Summary

      • 31 Days On Market

  • 4907 Quince St, Shady Side, MD 20764
    4907 Quince St, Shady Side, MD 20764
    4907 Quince St, Shady Side, MD 20764
    /4

    $50,000

    • Land
    • 7,405 Sq Ft
    • $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
  • 1509 Callaway Dr, Shady Side, MD 20764
    1509 Callaway Dr, Shady Side, MD 20764
    1509 Callaway Dr, Shady Side, MD 20764
    /49

    $375,000

    Sold May 18, 2026

    1509 Callaway Dr, Shady Side, MD 20764

    • 2 Beds
    • 1 Bath
    • 1,111 Sq Ft
    • Built 1952

    Last Sold Summary

    • 7% Above List Price
    • $338/SF
    • 2 Days On Market

    Current Estimated Value $350,088

    Last Listing Agent Cheryl Byrd Compass

    1509 Callaway Dr, Shady Side, MD 20764
    • 1207 Juniper St, Shady Side, MD 20764
      1207 Juniper St, Shady Side, MD 20764
      1207 Juniper St, Shady Side, MD 20764
      /77

      Est $493,954

      Not Listed For Sale

      1207 Juniper St, Shady Side, MD 20764

      • 4 Beds
      • 2.5 Baths
      • 2,064 Sq Ft
      • Built 1989
      1207 Juniper St, Shady Side, MD 20764

      Last Sold Summary

      • 152 Days On Market

  • 5771 Shady Side Rd, Churchton, MD 20733
    5771 Shady Side Rd, Churchton, MD 20733
    /2

    $40,000

    • Land
    • 14,810 Sq Ft
    • $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
  • 1503 Callaway Dr, Shady Side, MD 20764
    1503 Callaway Dr, Shady Side, MD 20764
    1503 Callaway Dr, Shady Side, MD 20764
    /25

    $276,000

    Sold Dec 22, 2025

    1503 Callaway Dr, Shady Side, MD 20764

    • 3 Beds
    • 2 Baths
    • 1,356 Sq Ft
    • Built 1950

    Last Sold Summary

    • $204/SF
    • 4 Days On Market

    Current Estimated Value $333,426

    Last Listing Agent Barb Atkinson RE/MAX Executive

    1503 Callaway Dr, Shady Side, MD 20764
    • 1505 Baker Rd, Shady Side, MD 20764
      1505 Baker Rd, Shady Side, MD 20764
      1505 Baker Rd, Shady Side, MD 20764
      /18

      Est $331,331

      Not Listed For Sale

      1505 Baker Rd, Shady Side, MD 20764

      • 2 Beds
      • 1 Bath
      • 960 Sq Ft
      • Built 1950
      1505 Baker Rd, Shady Side, MD 20764

      Last Sold Summary

      • 41 Days On Market

  • 1436 Haile Pkwy, Shady Side, MD 20764
    1436 Haile Pkwy, 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 accessibility. With

    Joan Stansfield Samson Properties

    1436 Haile Pkwy, Shady Side, MD 20764
  • 1181 Cedar Ave, Shady Side, MD 20764
    1181 Cedar Ave, Shady Side, MD 20764
    1181 Cedar Ave, Shady Side, MD 20764
    /44

    $420,000

    Sold Jul 25, 2025

    1181 Cedar Ave, Shady Side, MD 20764

    • 4 Beds
    • 2 Baths
    • 1,648 Sq Ft
    • Built 1940

    Last Sold Summary

    • $255/SF
    • 5 Days On Market

    Current Estimated Value $439,709

    Last Listing Agent Ben Miller Synergy Realty

    1181 Cedar Ave, Shady Side, MD 20764
    • 5326 Al Jones Dr, Shady Side, MD 20764
      5326 Al Jones Dr, Shady Side, MD 20764
      5326 Al Jones Dr, Shady Side, MD 20764
      /13

      Est $296,571

      Not Listed For Sale

      5326 Al Jones Dr, Shady Side, MD 20764

      • 2 Beds
      • 1 Bath
      • 576 Sq Ft
      • Built 1940
      5326 Al Jones Dr, Shady Side, MD 20764

      Last Sold Summary

      • 13 Days On Market

  • 5211 Al Jones Dr, Shady Side, MD 20764
    5211 Al Jones Dr, Shady Side, MD 20764
    5211 Al Jones Dr, Shady Side, MD 20764
    /39

    $535,000

    • 2 Beds
    • 1.5 Baths
    • 1,244 Sq Ft

    5211 Al Jones Dr, Shady Side, MD 20764

    Non-riparian waterfront home offering sweeping, unobstructed views of the Chesapeake Bay. Wake each morning to breathtaking sunrises over the water, best enjoyed from your expansive deck with a cup of coffee in hand—an experience that never gets old. Inside, the home is filled with natural light and features an open-concept layout designed to maximize those stunning bay views. The main level

    Ray Mudd Schwartz Realty, Inc.

    5211 Al Jones Dr, Shady Side, MD 20764
  • 4925 Aspen St, Shady Side, MD 20764
    4925 Aspen St, Shady Side, MD 20764
    4925 Aspen St, Shady Side, MD 20764
    /34

    $335,000

    Sold Sep 04, 2025

    4925 Aspen St, Shady Side, MD 20764

    • 2 Beds
    • 1 Bath
    • 1,060 Sq Ft
    • Built 1989

    Last Sold Summary

    • $316/SF
    • 3 Days On Market

    Current Estimated Value $350,653

    Last Listing Agent Jaime Rollins CENTURY 21 New Millennium

    4925 Aspen St, Shady Side, MD 20764
    • 4931 Idlewilde Rd, Shady Side, MD 20764
      4931 Idlewilde Rd, Shady Side, MD 20764
      4931 Idlewilde Rd, Shady Side, MD 20764
      /58

      Est $612,028

      Not Listed For Sale

      4931 Idlewilde Rd, Shady Side, MD 20764

      • 3 Beds
      • 2 Baths
      • 1,534 Sq Ft
      • Built 1993
      4931 Idlewilde Rd, Shady Side, MD 20764

      Last Sold Summary

      • 2 Days On Market

  • 6512 Shady Side Rd, Shady Side, MD 20764
    6512 Shady Side Rd, Shady Side, MD 20764
    6512 Shady Side Rd, Shady Side, MD 20764
    /12

    $198,000

    $47K PRICE DROP Under Contract
    • Land
    • 1.44 Acres
    • $137,500 per Acre

    6512 Shady Side Rd, Shady Side, MD 20764

    This lot could .be yours, surrounded by nature, in conservation easement, Dry wooded lot! Build your dream home, surrounded by trees and by 73 acres in conservation easement. Next to 6508 lot, they share an easement for driveway. The best lot in the area!! Close to Baltimore, DC, and Annapolis. Located near the West River and community baseball diamond and basketball court.

    George Heine Schwartz Realty, Inc.

    6512 Shady Side Rd, Shady Side, MD 20764
  • 5321 Browns Way, Churchton, MD 20733
    5321 Browns Way, Churchton, MD 20733
    /2

    $110,000

    Sold Jan 09, 2026

    5321 Browns Way, Churchton, MD 20733

    • 2 Beds
    • 1 Bath
    • 768 Sq Ft
    • Built 1940

    Last Sold Summary

    • $143/SF

    Current Estimated Value $257,667

    Last Listing Agent Ray Mudd Schwartz Realty, Inc.

    5321 Browns Way, Churchton, MD 20733

Showing Results 41 - 80, Page 2 of 18

Maryland Anne Arundel County Shady Side

Real Estate & Homes

How to Buy a Home How to Finance a Home How to Sell a Home

Disclaimer: Certain information contained herein is derived from information provided by parties other than Homes.com. All information provided is deemed reliable, but is not guaranteed to be accurate and should be independently verified.

Homes.com Licensing Information

§ 442-H New York Standard Operating Procedures

New York Fair Housing Notice

TREC: Information about brokerage services, Consumer protection notice

California DRE #01937601

Contact Homes.com Brokerage

Copyright © 2026 CoStar Group