3,279

Shady Side, MD Homes

Section Image
  • /40

    $354,500

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

    1617 Winters Ave, Shady Side, MD 20764

    Discover your waterfront retreat with Chesapeake Bay views, community water access, and an ideal location for both everyday living and weekend escapes. The stunning upper-level living area features vaulted ceiling, a classic wood-burning fireplace, and beautiful hardwood flooring that creates a warm and inviting atmosphere. Large, upgraded windows fill the home with natural light while showcasing

    Jeffrey Lewis Berkshire Hathaway HomeServices PenFed Realty

    1617 Winters Ave, Shady Side, MD 20764
  • /48

    $572,465

    Sold May 12, 2026

    5208 Hawk Channel Dr, West River, MD 20778

    • 3 Beds
    • 2.5 Baths
    • 1,820 Sq Ft
    • Built 1989

    Last Sold Summary

    • 2% Above List Price
    • $315/SF
    • 2 Days On Market

    Current Estimated Value $557,945

    Last Listing Agent Jenna Maseritz Park Modern Realty

    5208 Hawk Channel Dr, West River, MD 20778
    • /33

      Est $402,809

      Not Listed For Sale

      1422 Columbia Beach Rd, Shady Side, MD 20764

      • 2 Beds
      • 2 Baths
      • 1,285 Sq Ft
      • Built 1950
      1422 Columbia Beach Rd, Shady Side, MD 20764

      Last Sold Summary

      • 109 Days On Market

  • /2

    $100,000

    • Land
    • 29,620 Sq Ft
    • $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 effortless—yet

    Joan Stansfield Samson Properties

    1445 & 1447 Haile Pkwy, 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 $495,962

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

    1216 Grove Ave, Shady Side, MD 20764
    • /79

      Est $951,323

      Not Listed For Sale

      5060 Lerch Dr, Shady Side, MD 20764

      • 3 Beds
      • 4.5 Baths
      • 1,888 Sq Ft
      • Built 1998
      5060 Lerch Dr, Shady Side, MD 20764

      Last Sold Summary

      • 20 Days On Market

  • /2

    $125,000

    • Land
    • 4 Acres
    • $31,250 per Acre

    1495 Shady Rest Rd, Shady Side, MD 20764

    Discover a unique investment opportunity with this expansive 4-acre parcel of land, perfect for those looking to capitalize on future development potential. Nestled in a serene setting, this property offers ample space for creative vision-whether you envision a private retreat, agricultural venture, or a residential community. The generous lot size provides flexibility for various projects,

    Shawn Kerr Union Preferred Realty

    1495 Shady Rest Rd, Shady Side, MD 20764
  • /39

    $385,000

    Sold May 06, 2026

    1330 Jordan Dr, Shady Side, MD 20764

    • 3 Beds
    • 2.5 Baths
    • 1,440 Sq Ft
    • Built 1991

    Last Sold Summary

    • 8% Below List Price
    • $267/SF
    • 59 Days On Market

    Current Estimated Value $399,219

    Last Listing Agent Emily Motto Investors Management, Inc.

    1330 Jordan Dr, Shady Side, MD 20764
    • /26

      Est $400,725

      Not Listed For Sale

      1210 Oak Ave, Shady Side, MD 20764

      • 3 Beds
      • 2 Baths
      • 1,062 Sq Ft
      • Built 1981
      1210 Oak Ave, Shady Side, MD 20764

      Last Sold Summary

      • 4 Days On Market

  • /14

    $199,900

    $35K PRICE DROP Pending
    • 2 Beds
    • 1 Bath
    • 736 Sq Ft

    1502 Garst Rd, Shady Side, MD 20764

    Investor special in the charming Columbia Beach community of Shadyside. This quaint 2-bedroom, 1-bath home offers great potential for investors, renovators, or buyers looking to create their own coastal retreat. Inside, you'll find classic panel walls, a cozy fireplace, and a bright sunroom that adds extra living space and character. Nestled in a peaceful setting near the water, this property is

    Victoria Carmon-Brown Fusion Elite Realty

    1502 Garst Rd, Shady Side, MD 20764
  • /40

    $385,999

    Sold Feb 27, 2026

    4937 Aspen St, Shady Side, MD 20764

    • 2 Beds
    • 2 Baths
    • 886 Sq Ft
    • Built 1939

    Last Sold Summary

    • 2% Above List Price
    • $436/SF
    • 14 Days On Market

    Current Estimated Value $381,099

    Last Listing Agent Pedro Paz Coldwell Banker Realty

    4937 Aspen St, Shady Side, MD 20764
    • /62

      Est $484,943

      Not Listed For Sale

      1345 Jordan Dr, Shady Side, MD 20764

      • 3 Beds
      • 2.5 Baths
      • 1,540 Sq Ft
      • Built 2001
      1345 Jordan Dr, Shady Side, MD 20764

      Last Sold Summary

      • 2 Days On Market

  • /72

    $540,000

    $10K PRICE DROP
    • 4 Beds
    • 2.5 Baths
    • 1,812 Sq Ft

    1005 Hawk Channel Ct, West River, MD 20778

    BUYERS GOT COLD FEET! No inspections were completed. Welcome to the rarely available water- privileged Cedarlea community in West River—Tucked away at the end of a quiet, family-friendly cul-de-sac, this beautifully maintained 4-bedroom, 2.5-bath home offers the perfect blend of comfort, space, and privacy and is ready for its new owners. From the moment you arrive, the inviting front porch sets

    Stephanie Smith Douglas Realty, LLC

    1005 Hawk Channel Ct, West River, MD 20778
  • /51

    $389,000

    Sold Aug 15, 2025

    4977 Lerch Dr, Shady Side, MD 20764

    • 3 Beds
    • 1 Bath
    • 1,407 Sq Ft
    • Built 1940

    Last Sold Summary

    • $276/SF
    • 21 Days On Market

    Current Estimated Value $413,591

    Last Listing Agent Suebina Wong Douglas Realty, LLC

    4977 Lerch Dr, Shady Side, MD 20764
    • /57

      Est $423,824

      Not Listed For Sale

      4911 Chestnut St, Shady Side, MD 20764

      • 3 Beds
      • 2 Baths
      • 1,356 Sq Ft
      • Built 1990
      4911 Chestnut St, Shady Side, MD 20764

      Last Sold Summary

      • 4 Days On Market

  • /101

    $2,425,000

    Under Contract
    • 5 Beds
    • 5 Baths
    • 5,854 Sq Ft

    1125 Cherry Point Rd, West River, MD 20778

    Prepare to be WOW'd by this stunning, custom-built waterfront showpiece where every detail has been thoughtfully curated and nothing is ordinary. From the moment you arrive, the approach makes a lasting impression -- both private and substantial. The paver driveway with expanded parking, framed by professionally designed landscaping with full irrigation, is anchored by an expansive lush front

    Joan Stansfield Samson Properties

    1125 Cherry Point Rd, West River, MD 20778
  • /21

    $370,000

    Sold Aug 29, 2025

    1216 Hawthorne St, Shady Side, MD 20764

    • 3 Beds
    • 2.5 Baths
    • 1,100 Sq Ft
    • Built 1992

    Last Sold Summary

    • $336/SF
    • 47 Days On Market

    Current Estimated Value $386,561

    Last Listing Agent TJ Alves Cummings & Co. Realtors

    1216 Hawthorne St, Shady Side, MD 20764
    • /44

      Est $467,001

      Not Listed For Sale

      1229 Holly Ave, Shady Side, MD 20764

      • 3 Beds
      • 2.5 Baths
      • 1,544 Sq Ft
      • Built 2005
      1229 Holly Ave, Shady Side, MD 20764

      Last Sold Summary

      • 4 Days On Market

  • /2

    $499,990

    Open House 7/12 Coming Soon
    • 3 Beds
    • 2.5 Baths
    • 1,783 Sq Ft

    1016 Allen Ave, West River, MD 20778

    Welcome home to this beautiful brick-front Colonial nestled in the sought-after waterfront community of Back Bay Beach in West River! Just in time for summer, enjoy the ultimate Chesapeake Bay lifestyle with community access to a boat launch—perfect for launching your boat, jet skis, kayaks, and all your favorite water toys for endless days on the water. Situated on a spacious lot, this

    Nicki Palermo RE/MAX One

    1016 Allen Ave, West River, MD 20778
  • /30

    $530,000

    Sold Mar 30, 2026

    1006 Allen Ave, West River, MD 20778

    • 4 Beds
    • 2.5 Baths
    • 1,900 Sq Ft
    • Built 2003

    Last Sold Summary

    • 1% Above List Price
    • $279/SF
    • 1 Day On Market

    Current Estimated Value $526,918

    Last Listing Agent Dawn Riley Deep Roots Real Estate

    1006 Allen Ave, West River, MD 20778
    • /50

      Est $557,220

      Not Listed For Sale

      4940 W End Ave, Shady Side, MD 20764

      • 4 Beds
      • 3.5 Baths
      • 2,012 Sq Ft
      • Built 1990
      4940 W End Ave, Shady Side, MD 20764

      Last Sold Summary

      • 24 Days On Market

  • /16

    $560,000

    Open Sat 11AM - 1PM
    • 4 Beds
    • 2 Baths
    • 1,713 Sq Ft

    6213 Shady Side Rd, Shady Side, MD 20764

    Charming 4-bedroom, 2-bath cottage situated on 10 picturesque acres, offering the perfect blend of comfort, privacy, and country living. Enjoy endless opportunities for gardening, outdoor recreation, and creating your own private retreat. The expansive property provides plenty of space for entertaining family and friends, hosting gatherings, or simply relaxing and enjoying the peaceful

    Shate Jackson Coldwell Banker Realty

    6213 Shady Side Rd, Shady Side, MD 20764
  • /67

    $1,000,000

    Sold Oct 10, 2025

    4715 Oak Rd, Shady Side, MD 20764

    • 4 Beds
    • 2.5 Baths
    • 3,244 Sq Ft
    • Built 1936

    Last Sold Summary

    • $308/SF
    • 67 Days On Market

    Current Estimated Value $1,029,211

    Last Listing Agent Angie Carr Riverscape Realty

    4715 Oak Rd, Shady Side, MD 20764
    • /55

      Est $506,835

      Not Listed For Sale

      4727 Frederick Ave, Shady Side, MD 20764

      • 5 Beds
      • 3 Baths
      • 2,220 Sq Ft
      • Built 1965
      4727 Frederick Ave, Shady Side, MD 20764

      Last Sold Summary

      • 23 Days On Market

  • /2

    $120,000

    • Land
    • 19,166 Sq Ft
    • $272,727 per Acre

    1186 & 1188 Poplar Ave, Shady Side, MD 20764

    Sale includes both 1186 & 1188 Poplar Ave. Lots: 10,11,12,13 Rare opportunity to purchase two adjoining parcels totaling approximately 19,000 square feet or nearly 1/2 acre in the water-privileged community of Cedarhurst on the Bay. Build your dream home and enjoy the relaxed Chesapeake Bay lifestyle that makes Shady Side one of Anne Arundel County's hidden gems. Community amenities include Bay

    Adam Carpenter Keller Williams Flagship

    1186 & 1188 Poplar Ave, Shady Side, MD 20764
  • /44

    $2,000,000

    Sold Oct 31, 2025

    4819 Avery Rd, Shady Side, MD 20764

    • 5 Beds
    • 4.5 Baths
    • 5,151 Sq Ft
    • Built 2007

    Last Sold Summary

    • $388/SF
    • 2 Days On Market

    Current Estimated Value $2,033,547

    Last Listing Agent Brad Kappel TTR Sotheby's International Realty

    4819 Avery Rd, Shady Side, MD 20764
    • /49

      Est $448,110

      Not Listed For Sale

      1213 Grove Ave, Shady Side, MD 20764

      • 4 Beds
      • 2.5 Baths
      • 1,728 Sq Ft
      • Built 1984
      1213 Grove Ave, Shady Side, MD 20764

      Last Sold Summary

      • 7 Days On Market

  • /72

    $1,099,000

    $50K PRICE DROP Under Contract
    • 3 Beds
    • 2 Baths
    • 1,964 Sq Ft

    1268 Hayes Rd, Shady Side, MD 20764

    Discover your dream lifestyle in this exceptional 3 bedroom 2 full bath waterfront property located at 1268 Hayes Road in the charming community of Shady Side, MD. combining the peacefulness of a secluded setting with essential modern amenities. As you step inside you'll notice the sun drenched open floor plan complete with a large cooks kitchen featuring a huge center island, cozy breakfast nook

    Casey A Sutherland Maryland Waterfront Properties LLC

    1268 Hayes Rd, Shady Side, MD 20764
  • /2

    $415,000

    Sold Mar 31, 2026

    1176 Spruce Ave, Shady Side, MD 20764

    • 3 Beds
    • 2 Baths
    • 1,400 Sq Ft
    • Built 1987

    Last Sold Summary

    • 5% Above List Price
    • $296/SF
    • 0 Days On Market

    Current Estimated Value $407,338

    Last Listing Agent Steve Brien Home Towne Real Estate

    1176 Spruce Ave, Shady Side, MD 20764
    • /40

      Est $1,692,416

      Not Listed For Sale

      1243 Bast Ln, Shady Side, MD 20764

      • 5 Beds
      • 5 Baths
      • 4,179 Sq Ft
      • Built 2024
      1243 Bast Ln, Shady Side, MD 20764

      Last Sold Summary

      • 0 Days On Market

  • /35

    $600,000

    Pending
    • 4 Beds
    • 3.5 Baths
    • 2,071 Sq Ft

    1205 Hawthorne St, Shady Side, MD 20764

    This stunning Craftsman-style home in the Avalon Shores community offers a perfect blend of modern luxury and serene bayside living. Featuring beautiful quartz countertops, a functional island, a pantry, and stainless steel appliances. Enjoy open-concept living with 9'+ ceilings, luxury vinyl plank (LVP) waterproof flooring, and Craftsman-style trim. The three-story design includes upper-level

    Brandi Bradshaw Keller Williams Select Realtors of Annapolis

    1205 Hawthorne St, Shady Side, MD 20764
  • /55

    $835,000

    Sold Apr 06, 2026

    1379 McDonald Rd, Shady Side, MD 20764

    • 4 Beds
    • 2.5 Baths
    • 2,485 Sq Ft
    • Built 2025

    Last Sold Summary

    • $336/SF
    • 32 Days On Market

    Current Estimated Value $826,397

    Last Listing Agent Adam Ellison Long & Foster Real Estate, Inc.

    1379 McDonald Rd, Shady Side, MD 20764
    • /27

      Est $484,154

      Not Listed For Sale

      4722 Girton Ave, Shady Side, MD 20764

      • 3 Beds
      • 2.5 Baths
      • 1,788 Sq Ft
      • Built 2019
      4722 Girton Ave, Shady Side, MD 20764

      Last Sold Summary

  • /35

    $729,900

    • 3 Beds
    • 2 Baths
    • 1,866 Sq Ft

    1650 Cedar Ln, Shady Side, MD 20764

    Experience Unmatched Privacy and Tranquility from this unique non-riparian waterfront home set on over 3+ scenic acres. Fall in love with sweeping water views and the serene presence of native wildlife—waterfowl, deer, eagles, and more—all just outside your door. Enjoy panoramic vistas of a natural pond, with the stunning Chesapeake Bay visible in the distance. On clear days, the Bay Bridge is

    Ray Mudd Schwartz Realty, Inc.

    1650 Cedar Ln, Shady Side, MD 20764
  • /2

    $850,000

    Sold May 04, 2026

    5229 Al Jones Dr, Shady Side, MD 20764

    • 3 Beds
    • 3 Baths
    • 2,200 Sq Ft
    • Built 1945

    Last Sold Summary

    • 6% Above List Price
    • $386/SF
    • 4 Days On Market

    Current Estimated Value $804,589

    Last Listing Agent Greg Fisk Douglas Realty, LLC

    5229 Al Jones Dr, Shady Side, MD 20764
    • /41

      Est $628,620

      Not Listed For Sale

      1240 W River Rd, Shady Side, MD 20764

      • 3 Beds
      • 3.5 Baths
      • 2,081 Sq Ft
      • Built 2008
      1240 W River Rd, Shady Side, MD 20764

      Last Sold Summary

      • 38 Days On Market

  • /40

    $365,000

    • 2 Beds
    • 2 Baths
    • 864 Sq Ft

    4912 Beech St, Shady Side, MD 20764

    Welcome to this charming 2-bedroom, 2-bath home in the water-oriented community of Avalon Shores. Perfect for those looking to start out, scale down, or a second home! Freshly updated with new flooring, a new roof, and fresh paint- this home is truly move-in ready! Enjoy a fully renovated bathroom, a spacious deck, and a fully fenced backyard—perfect for pets, gatherings, or quiet relaxation.Step

    Juliet Patterson Samson Properties

    4912 Beech St, Shady Side, MD 20764
  • /34

    $325,000

    Sold Dec 19, 2025

    1731 Columbia Beach Rd, Shady Side, MD 20764

    • 2 Beds
    • 1 Bath
    • 900 Sq Ft
    • Built 1982

    Last Sold Summary

    • $361/SF
    • 13 Days On Market

    Current Estimated Value $330,333

    Last Listing Agent Jose Salvador Rivera Jr RE/MAX Excellence Realty

    1731 Columbia Beach Rd, Shady Side, MD 20764
    • /103

      Est $2,114,273

      Not Listed For Sale

      1258 W River Rd, Shady Side, MD 20764

      • 5 Beds
      • 4.5 Baths
      • 6,100 Sq Ft
      • Built 1930
      1258 W River Rd, Shady Side, MD 20764

      Last Sold Summary

      • 53 Days On Market

  • /61

    $659,990

    New Construction
    • 4 Beds
    • 2.5 Baths
    • 2,710 Sq Ft

    5314 Al Jones Dr, Shady Side, MD 20764

    4/6/26. Just broke ground. Late summer delivery. Coastal Living Just Steps from the Chesapeake Bay! Schaefer Homes invites you to make this beautifully designed coastal-style residence your own located across the street from the bay offering nice water views. Offering over 3 stories of wide open living with time to personalize your selections so you can create a home that perfectly reflects your

    Ray Mudd Schwartz Realty, Inc.

    5314 Al Jones Dr, Shady Side, MD 20764

Showing Results 121 - 160, Page 4 of 18

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