3,279

Shady Side, MD Homes

Section Image
    • /42

      Est $375,038

      Not Listed For Sale

      4737 Chesapeake Ave, Shady Side, MD 20764

      • 2 Beds
      • 1 Bath
      • 800 Sq Ft
      • Built 1940
      4737 Chesapeake Ave, Shady Side, MD 20764

      Last Sold Summary

      • 60 Days On Market

  • /41

    $399,000

    Under Contract
    • 3 Beds
    • 2.5 Baths
    • 1,344 Sq Ft

    4944 Beech St, Shady Side, MD 20764

    This lovely Colonial home is just steps away from the Avalon Shores private community beach. The home includes a gorgeous dine in kitchen, updated primary bedroom suite w/ balcony, cathedral ceilings, hardwood flooring, deck, nice front porch, shed, off st. parking and located on a quiet street. Owner's have lovingly cared for this home. Come and enjoy this lovely home and community.

    Payton Minor Taylor Properties

    4944 Beech St, Shady Side, MD 20764
  • /71

    $1,190,000

    Sold Aug 18, 2025

    1538 Robinson Rd, Shady Side, MD 20764

    • 3 Beds
    • 2.5 Baths
    • 2,060 Sq Ft
    • Built 2014

    Last Sold Summary

    • $578/SF
    • 142 Days On Market

    Current Estimated Value $1,207,547

    Last Listing Agent Jennifer Chaney Chaney Homes, LLC

    1538 Robinson Rd, Shady Side, MD 20764
    • /30

      Est $315,164

      Not Listed For Sale

      4854 Avery Rd, Shady Side, MD 20764

      • 2 Beds
      • 1 Bath
      • 704 Sq Ft
      • Built 1930
      4854 Avery Rd, Shady Side, MD 20764

      Last Sold Summary

      • 2 Days On Market

  • /2

    $25,000

    • Land
    • 4,791 Sq Ft
    • $227,273 per Acre

    0 Pine Ave Unit MDAA2139458, Shady Side, MD 20764

    ONLINE AUCTION: This auction takes place on the Ashland Auction Group Website Bidding Platform. Bidding begins 6/2/2026 @ 10:00 AM. Bidding ends 6/4/2026 @ 12:50 PM. List Price is Suggested Opening Bid. Deposit: $5,000. This +/- 4,750 ft2 parcel of land is located in located in Shady Side, MD within Anne Arundel County. Its location is just a few minutes away to Herring Bay. It also offers easy

    Adam Shpritz Ashland Auction Group LLC

    0 Pine Ave Unit MDAA2139458, Shady Side, MD 20764
  • /31

    $381,000

    Sold Jan 09, 2026

    1208 Oak Ave, Shady Side, MD 20764

    • 3 Beds
    • 2 Baths
    • 1,062 Sq Ft
    • Built 1981

    Last Sold Summary

    • $359/SF
    • 22 Days On Market

    Current Estimated Value $391,194

    Last Listing Agent Ray Mudd Schwartz Realty, Inc.

    1208 Oak Ave, Shady Side, MD 20764
    • /38

      Est $462,873

      Not Listed For Sale

      1195 Bayview Ave, Shady Side, MD 20764

      • 3 Beds
      • 2 Baths
      • 1,824 Sq Ft
      • Built 1960
      1195 Bayview Ave, Shady Side, MD 20764

      Last Sold Summary

      • 31 Days On Market

  • /12

    $99,000

    Pending
    • 3 Beds
    • 1 Bath

    1451 Shady Rest Rd, Shady Side, MD 20764

    Rare opportunity in Shady Side on 1.58 acres, just minutes from the Chesapeake Bay.1451 Shady Rest Rd features a partially built home.. The groundwork is in place, and the next owner can bring their own vision to life. The property includes a permitted 3-bedroom septic system and a working well, giving you a strong starting point for a new build. This desirable South County area is seeing

    Teal Clise EXP Realty, LLC

    1451 Shady Rest Rd, Shady Side, MD 20764
  • /5

    $389,000

    Sold May 21, 2026

    5839 Shady Side Rd, Churchton, MD 20733

    • 3 Beds
    • 2 Baths
    • 1,000 Sq Ft
    • Built 1962

    Last Sold Summary

    • $389/SF
    • 3 Days On Market

    Current Estimated Value $384,746

    Last Listing Agent Rebecca Gray Keller Williams Legacy

    5839 Shady Side Rd, Churchton, MD 20733
    • /54

      Est $490,737

      Not Listed For Sale

      1305 Maple St, Shady Side, MD 20764

      • 5 Beds
      • 2.5 Baths
      • 1,992 Sq Ft
      • Built 1992
      1305 Maple St, Shady Side, MD 20764

      Last Sold Summary

      • 17 Days On Market

  • /71

    $995,000

    Pending
    • 4 Beds
    • 3 Baths
    • 2,200 Sq Ft

    4936 Lerch Dr, Shady Side, MD 20764

    Waterfront luxury meets modern craftsmanship in this custom-built 2023 home, designed to capture stunning water views from nearly every room. Privately set with a pier, sun deck, 10,000 lb boat lift, and jet ski lift (2023), this is effortless waterfront living. Inside, no detail was overlooked—Anderson windows, shiplap accents, and a carpet-free design throughout. The main level offers two

    Nicki Palermo RE/MAX One

    4936 Lerch Dr, Shady Side, MD 20764
  • /90

    $1,100,000

    Sold Oct 15, 2025

    1323 Jordan Dr, Shady Side, MD 20764

    • 5 Beds
    • 3 Baths
    • 2,671 Sq Ft
    • Built 1940

    Last Sold Summary

    • $412/SF
    • 2 Days On Market

    Current Estimated Value $1,117,059

    Last Listing Agent Karlton Morris Long & Foster Real Estate, Inc.

    1323 Jordan Dr, Shady Side, MD 20764
    • /22

      Est $382,854

      Not Listed For Sale

      1170 Maple Ave, Shady Side, MD 20764

      • 3 Beds
      • 2 Baths
      • 1,120 Sq Ft
      • Built 1980
      1170 Maple Ave, Shady Side, MD 20764

      Last Sold Summary

      • 10 Days On Market

  • /76

    $3,500,000

    • 5 Beds
    • 5.5 Baths
    • 4,620 Sq Ft

    4750 Frederick Ave, Shady Side, MD 20764

    Silver Water is a rare west-facing waterfront home designed in direct response to the Chesapeake—offering broad water views, remarkable sunsets, and a level of architectural clarity seldom found in the area. Set behind a private gate on a beautifully landscaped one-acre lot along the West River, the property combines seclusion with convenient access to Annapolis and Washington, DC. Spanning over

    David Orso Berkshire Hathaway HomeServices PenFed Realty

    4750 Frederick Ave, Shady Side, MD 20764
  • /21

    $314,400

    Sold Apr 24, 2026

    1241 Steamboat Rd, Shady Side, MD 20764

    • 2 Beds
    • 1.5 Baths
    • 1,728 Sq Ft
    • Built 1948

    Last Sold Summary

    • 10% Below List Price
    • $182/SF
    • 61 Days On Market

    Current Estimated Value $324,173

    Last Listing Agent Ray Mudd Schwartz Realty, Inc.

    1241 Steamboat Rd, Shady Side, MD 20764
    • /39

      Est $615,217

      Not Listed For Sale

      1004 Hawk Channel Ct, West River, MD 20778

      • 4 Beds
      • 3.5 Baths
      • 2,566 Sq Ft
      • Built 1989
      1004 Hawk Channel Ct, West River, MD 20778

      Last Sold Summary

      • 138 Days On Market

  • /2

    $25,000

    • Land
    • 24,829 Sq Ft
    • $43,860 per Acre

    0 Haile Pkwy Unit MDAA2141624, 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, Baltimore, or

    Joan Stansfield Samson Properties

    0 Haile Pkwy Unit MDAA2141624, Shady Side, MD 20764
  • /31

    $599,999

    Sold Apr 30, 2026

    4951 Dogwood St, Shady Side, MD 20764

    • 4 Beds
    • 2.5 Baths
    • 2,586 Sq Ft
    • Built 2007

    Last Sold Summary

    • $232/SF
    • 14 Days On Market

    Current Estimated Value $600,864

    Last Listing Agent Carey Laycock RE/MAX Leading Edge

    4951 Dogwood St, Shady Side, MD 20764
    • /23

      Est $470,204

      Not Listed For Sale

      4961 Filbert St, Shady Side, MD 20764

      • 3 Beds
      • 2.5 Baths
      • 1,568 Sq Ft
      • Built 1995
      4961 Filbert St, Shady Side, MD 20764

      Last Sold Summary

      • 3 Days On Market

  • /61

    $849,990

    Open Sun 11AM - 1PM
    • 4 Beds
    • 3.5 Baths
    • 4,204 Sq Ft

    5331 Sweetwater Dr, West River, MD 20778

    Stately brick-front Colonial located in the highly sought-after water-privileged community of West River Estates. This absolutely gorgeous home offers exceptional space, charm, and amenities throughout. The beautifully appointed kitchen features granite countertops, double wall ovens, a large center island with built-in cooktop, and ample cabinetry. French doors open to a bright all-season

    Ray Mudd Schwartz Realty, Inc.

    5331 Sweetwater Dr, West River, MD 20778
  • /33

    $925,000

    Sold Aug 08, 2025

    4927 Hine Dr, Shady Side, MD 20764

    • 4 Beds
    • 2.5 Baths
    • 3,445 Sq Ft
    • Built 1993

    Last Sold Summary

    • $269/SF
    • 127 Days On Market

    Current Estimated Value $989,528

    Last Listing Agent William Whitman Long & Foster Real Estate, Inc.

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

      Est $518,686

      Not Listed For Sale

      6039 Shady Side Rd, Shady Side, MD 20764

      • 3 Beds
      • 2.5 Baths
      • 1,748 Sq Ft
      • Built 2007
      6039 Shady Side Rd, Shady Side, MD 20764

      Last Sold Summary

      • 122 Days On Market

  • /2

    $352,000

    Coming Soon
    • 2 Beds
    • 2 Baths
    • 1,144 Sq Ft

    1500 Garst Rd, Shady Side, MD 20764

    Maggie Richards Berkshire Hathaway HomeServices PenFed Realty

    1500 Garst Rd, Shady Side, MD 20764
  • /2

    $760,000

    Sold May 21, 2026

    617 Plantation Blvd, West River, MD 20778

    • 4 Beds
    • 2.5 Baths
    • 3,679 Sq Ft
    • Built 1990

    Last Sold Summary

    • 1% Above List Price
    • $207/SF
    • 5 Days On Market

    Current Estimated Value $750,417

    Last Listing Agent Nicki Palermo RE/MAX One

    617 Plantation Blvd, West River, MD 20778
    • /20

      Est $356,660

      Not Listed For Sale

      1206 Holly Ave, Shady Side, MD 20764

      • 2 Beds
      • 1 Bath
      • 1,083 Sq Ft
      • Built 1950
      1206 Holly Ave, Shady Side, MD 20764

      Last Sold Summary

  • /27

    $379,900

    $20K PRICE DROP
    • 3 Beds
    • 2 Baths
    • 1,223 Sq Ft

    4738 Washington Ave, Shady Side, MD 20764

    Perfect little rancher in a water access community. 3 bedrooms, 2 full baths, and a full fenced yard. Heated family/sun room out back and setup for a stackable washer/dryer inside.

    Kyle Squires Lazar Real Estate

    4738 Washington Ave, Shady Side, MD 20764
  • /27

    $449,950

    Sold Oct 16, 2025

    1192 Oak Ave, Shady Side, MD 20764

    • 3 Beds
    • 2 Baths
    • 1,224 Sq Ft
    • Built 1988

    Last Sold Summary

    • $368/SF
    • 8 Days On Market

    Current Estimated Value $453,751

    Last Listing Agent Ronald Watson Flag Real Estate Inc.

    1192 Oak Ave, Shady Side, MD 20764
    • /24

      Est $374,975

      Not Listed For Sale

      1172 Maple Ave, Shady Side, MD 20764

      • 3 Beds
      • 1.5 Baths
      • 1,040 Sq Ft
      • Built 1979
      1172 Maple Ave, Shady Side, MD 20764

      Last Sold Summary

      • 13 Days On Market

  • /42

    $325,000

    • 3 Beds
    • 1 Bath
    • 864 Sq Ft

    1172 Cedar Ave, Shady Side, MD 20764

    Welcome to Cedarhurst on the Bay, a charming waterfront community on the Shady Side Peninsula, conveniently located between Annapolis and Deale Maryland. This cute, updated rancher style home offers a rare affordable opportunity to enjoy Chesapeake Bay living, just one hour from the City. So much potential! Make it your weekend retreat, an Air B&B, or perhaps a tranquil place to retire, without

    James Basuel Weichert, REALTORS

    1172 Cedar Ave, Shady Side, MD 20764
  • /24

    $400,000

    Sold Mar 19, 2026

    5218 Nick Rd, Shady Side, MD 20764

    • 3 Beds
    • 2 Baths
    • 1,099 Sq Ft
    • Built 1940

    Last Sold Summary

    • $364/SF
    • 8 Days On Market

    Current Estimated Value $387,361

    Last Listing Agent Jonathan Vanegas Samson Properties

    5218 Nick Rd, Shady Side, MD 20764
    • /33

      Est $443,895

      Not Listed For Sale

      1016 Cosimano Place, West River, MD 20778

      • 3 Beds
      • 2.5 Baths
      • 1,714 Sq Ft
      • Built 1989
      1016 Cosimano Place, West River, MD 20778

      Last Sold Summary

      • 8 Days On Market

  • /27

    $1,495,000

    Under Contract
    • 3 Beds
    • 2.5 Baths
    • 1,620 Sq Ft

    4923 E Chalk Point Rd, West River, MD 20778

    This coastal home in the sought-after Chalk Point community offers the best of waterfront living. Wake up in the waterfront primary suite with sweeping 180-degree views and enjoy your morning coffee from the private balcony overlooking the water. Designed for both privacy and entertaining, the home features a spacious deck and patio off the main living area, perfect for outdoor gatherings and

    Amelia Whitman Long & Foster Real Estate, Inc.

    4923 E Chalk Point Rd, West River, MD 20778
  • /10

    $255,000

    Sold Jan 21, 2026

    5162 Cedarlea Dr, West River, MD 20778

    • Land
    • 15.59 Acres
    • $16,357 per Acre

    Last Sold Summary

    • 7 Days On Market

    Current Estimated Value $240,500

    Last Listing Agent Edith Marie Simpson Long & Foster Real Estate, Inc.

    5162 Cedarlea Dr, West River, MD 20778
    • /84

      Est $1,497,058

      Not Listed For Sale

      4923 Thomas Dr, Shady Side, MD 20764

      • 4 Beds
      • 4.5 Baths
      • 4,720 Sq Ft
      • Built 2010
      4923 Thomas Dr, Shady Side, MD 20764

      Last Sold Summary

      • 80 Days On Market

  • /17

    $349,870

    • Land
    • 6,534 Sq Ft
    • $2,332,467 per Acre

    5235 Al Jones Dr, Shady Side, MD 20764

    Unique Waterfront Lot Opportunity at Columbia Beach – Build Your Dream Home on the Chesapeake Bay. Don't miss this rare chance to own a buildable waterfront lot in the serene, gated community of Columbia Beach, offering breathtaking views of the Chesapeake Bay. This exclusive neighborhood is just 30 minutes from the I-495 Beltway and Annapolis, and only 45 minutes to Washington, D.C., and the

    Rodrigo Cruz Long & Foster Real Estate, Inc.

    5235 Al Jones Dr, Shady Side, MD 20764
  • /4

    $420,000

    Sold Oct 10, 2025

    5196 Chesapeake Ave, Shady Side, MD 20764

    • 2 Beds
    • 2 Baths
    • 934 Sq Ft
    • Built 1986

    Last Sold Summary

    • $450/SF
    • 0 Days On Market

    Current Estimated Value $440,235

    Last Listing Agent Joshua Shapiro Douglas Realty, LLC

    5196 Chesapeake Ave, Shady Side, MD 20764
    • /54

      Est $522,172

      Not Listed For Sale

      1184 Holly Ave, Shady Side, MD 20764

      • 4 Beds
      • 2.5 Baths
      • 1,870 Sq Ft
      • Built 2011
      1184 Holly Ave, Shady Side, MD 20764

      Last Sold Summary

      • 12 Days On Market

  • /2

    $25,000

    • Land
    • 4,791 Sq Ft
    • $227,273 per Acre

    1205 Poplar Ave, Shady Side, MD 20764

    ONLINE AUCTION: This auction takes place on the Ashland Auction Group website bidding platform. Bidding begins 6/29/2026, 10:00 AM. Bidding ends 7/1/2026, 7:00 PM. The list price is the suggested opening bid. Deposit: $5,000. This +/- 4,750 ft2 parcel of land is located in Shady Side, MD within Anne Arundel County. It is just minutes away to Herring Bay and offers easy access to major traffic

    Adam Shpritz Ashland Auction Group LLC

    1205 Poplar Ave, Shady Side, MD 20764
  • /12

    $185,000

    Sold Jul 11, 2025

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

    • Land
    • 2.86 Acres
    • $64,685 per Acre

    Last Sold Summary

    • 91 Days On Market

    Current Estimated Value $191,626

    Last Listing Agent Bill Beam Beam Realty Group, Inc.

    1344 E West Shady Side Rd, Shady Side, MD 20764
    • /43

      Est $475,239

      Not Listed For Sale

      4718 Washington Ave, Shady Side, MD 20764

      • 4 Beds
      • 2.5 Baths
      • 1,947 Sq Ft
      • Built 2003
      4718 Washington Ave, Shady Side, MD 20764

      Last Sold Summary

      • 3 Days On Market

Showing Results 81 - 120, Page 3 of 18

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