3,274

Shady Side, MD Homes

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  • /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 $1,200,184

    Last Listing Agent Jennifer Chaney Chaney Homes, LLC

    1538 Robinson Rd, Shady Side, MD 20764
    • /38

      Est $469,485 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

      • 6% Above List Price
      • $242/SF
      • 31 Days On Market
      • Last Sold Price $441,000
      • Sep 26, 2023

      Last Listing Agent Alissa Bond Berkshire Hathaway HomeServices Homesale Realty

  • /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
  • /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 $395,997

    Last Listing Agent Ray Mudd Schwartz Realty, Inc.

    1208 Oak Ave, Shady Side, MD 20764
    • /54

      Est $495,646 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

      • 7% Above List Price
      • $233/SF
      • 17 Days On Market
      • Last Sold Price $465,000
      • Feb 28, 2025

      Last Listing Agent Pattee McInerney Scott McInerney RE/MAX

  • /5

    $389,900 Pending

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

    5839 Shady Side Rd, Churchton, MD 20733

    Completely updated and move-in ready, this 3-bedroom, 2 full bath home is ideally located in the Churchton/Shady Side area just minutes from the water!! Major recent improvements include brand new HVAC, and new roof! The interior has been refreshed with new flooring throughout and a renovated kitchen featuring new cabinets, countertops, and appliances. Both bathrooms fully updated! A great

    Rebecca Gray Keller Williams Legacy

    5839 Shady Side Rd, Churchton, MD 20733
  • /20

    $310,000 Sold May 30, 2025

    4871 Avery Rd, Shady Side, MD 20764

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

    Last Sold Summary

    • $371/SF
    • 4 Days On Market

    Current Estimated Value $355,890

    Last Listing Agent Melanie Montague EXP Realty, LLC

    4871 Avery Rd, Shady Side, MD 20764
    • /22

      Est $385,702 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

      • 6% Above List Price
      • $326/SF
      • 10 Days On Market
      • Last Sold Price $365,000
      • May 30, 2024

      Last Listing Agent Alexandra McDowell Compass

  • /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
  • /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 $1,094,947

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

    1323 Jordan Dr, Shady Side, MD 20764
    • /39

      Est $628,340 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

      • 5% Above List Price
      • $234/SF
      • 138 Days On Market
      • Last Sold Price $599,900
      • Oct 17, 2024

      Last Listing Agent Kara Leddy Coldwell Banker (NRT-Southeast-MidAtlantic)

  • /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
  • /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 $326,735

    Last Listing Agent Ray Mudd Schwartz Realty, Inc.

    1241 Steamboat Rd, Shady Side, MD 20764
    • /23

      Est $454,725 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

      • 6% Above List Price
      • $274/SF
      • 3 Days On Market
      • Last Sold Price $430,000
      • Jun 09, 2023

      Last Listing Agent Rick Gloekler RE/MAX

  • /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
  • /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 $600,647

    Last Listing Agent Carey Laycock RE/MAX Leading Edge

    4951 Dogwood St, Shady Side, MD 20764
    • /34

      Est $364,386 Not Listed For Sale

      4912 Beech St, Shady Side, MD 20764

      • 2 Beds
      • 2 Baths
      • 864 Sq Ft
      • Built 1989
      4912 Beech St, Shady Side, MD 20764

      Last Sold Summary

      • 14% Above List Price
      • $370/SF
      • 5 Days On Market
      • Last Sold Price $320,000
      • Jan 05, 2024

      Last Listing Agent Mark Frisco Century 21 New Millennium

  • /12

    $198,000 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
  • /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 $968,568

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

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

      Est $521,827 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

      • 22% Above List Price
      • $245/SF
      • 122 Days On Market
      • Last Sold Price $429,000
      • Aug 17, 2023

      Last Listing Agent Robyn Day RE/MAX

  • /42

    $429,900

    • 3 Beds
    • 1.5 Baths
    • 1,386 Sq Ft

    4912 Mariners Dr, Shady Side, MD 20764

    Coastal Affordable Living with a Boat Slip Included Discover the charm of Snug Harbor, where coastal living meets everyday affordability. This beautifully updated home offers gorgeous Chesapeake Bay views and the rare bonus of an included boat slip — making waterfront living more accessible than ever. Inside offers a light-filled floorplan, wide open living room, an open kitchen shines with

    Sam Barbieri RE/MAX United Real Estate

    4912 Mariners Dr, 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 $448,557

    Last Listing Agent Ronald Watson Flag Real Estate Inc.

    1192 Oak Ave, Shady Side, MD 20764
    • /20

      Est $354,533 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

      • 14% Above List Price
      • $286/SF
      • Last Sold Price $310,000
      • Nov 13, 2023

      Last Listing Agent Jerry Kline Keller Williams Flagship

  • /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
  • /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 $373,499

    Last Listing Agent Jonathan Vanegas Samson Properties

    5218 Nick Rd, Shady Side, MD 20764
    • /24

      Est $383,568 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

      • 2% Above List Price
      • $362/SF
      • 13 Days On Market
      • Last Sold Price $376,000
      • Dec 16, 2024

      Last Listing Agent Bita Dayhoff Compass

  • /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
  • /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
    • /75

      Est $1,251,072 Not Listed For Sale

      1326 W River Rd, Shady Side, MD 20764

      • 4 Beds
      • 3 Baths
      • 2,617 Sq Ft
      • Built 1966
      1326 W River Rd, Shady Side, MD 20764

      Last Sold Summary

      • 4% Below List Price
      • $501/SF
      • 1 Day On Market
      • Last Sold Price $1,310,000
      • May 26, 2023

      Last Listing Agent Nicki Palermo RE/MAX One

  • /71

    $995,000 Under Contract

    • 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
  • /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 $423,080

    Last Listing Agent Joshua Shapiro Douglas Realty, LLC

    5196 Chesapeake Ave, Shady Side, MD 20764
    • /33

      Est $450,861 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

      • 6% Above List Price
      • $248/SF
      • 8 Days On Market
      • Last Sold Price $425,000
      • Apr 23, 2024

      Last Listing Agent Julie Katcef Engel & Völkers Annapolis

  • /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
  • /32

    $450,000 Sold May 16, 2025

    1233 Juniper St, Shady Side, MD 20764

    • 4 Beds
    • 2.5 Baths
    • 1,899 Sq Ft
    • Built 2007

    Last Sold Summary

    • $237/SF
    • 0 Days On Market

    Current Estimated Value $474,574

    Last Listing Agent Nicki Palermo RE/MAX One

    1233 Juniper St, Shady Side, MD 20764
    • /84

      Est $1,514,840 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

      • 3% Above List Price
      • $312/SF
      • 80 Days On Market
      • Last Sold Price $1,475,000
      • Feb 28, 2025

      Last Listing Agent Kara Chaffin Donofrio Long & Foster

  • /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
  • /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 $188,402

    Last Listing Agent Bill Beam Beam Realty Group, Inc.

    1344 E West Shady Side Rd, Shady Side, MD 20764
    • /54

      Est $526,401 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

      • 2% Above List Price
      • $275/SF
      • 12 Days On Market
      • Last Sold Price $515,000
      • Jun 26, 2023

      Last Listing Agent Mary Gatton Redfin Corp

  • /53

    $370,000 Pending

    • 3 Beds
    • 2.5 Baths
    • 768 Sq Ft

    5063 Lerch Dr, Shady Side, MD 20764

    Delaney Clarke RE/MAX United Real Estate

    5063 Lerch Dr, Shady Side, MD 20764
  • /42

    $465,000 Sold Sep 26, 2025

    1216 Grove Ave, Shady Side, MD 20764

    • 5 Beds
    • 2.5 Baths
    • 2,051 Sq Ft
    • Built 1965

    Last Sold Summary

    • $227/SF
    • 37 Days On Market

    Current Estimated Value $484,610

    Last Listing Agent Paul Lee Long & Foster Real Estate, Inc.

    1216 Grove Ave, Shady Side, MD 20764

Showing Results 81 - 120, Page 3 of 18

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