Shady Side, MD Homes

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  /130

  $700,000 Under Contract

  • 5 Beds
  • 3 Baths
  • 2,620 Sq Ft

  4919 Mariners Dr, Shady Side, MD 20764

  Welcome to a home that doesn’t just offer a place to live—it offers a lifestyle on the Chesapeake Bay. As you approach the property, the experience begins immediately. The driveway and gated entry set the tone, leading you toward a waterfront sanctuary where every detail elevates coastal living. This home sits directly on the water, complete with a slip and a finger pier, so you can tie up your

  Lily Vallario EXP Realty, LLC

  4919 Mariners Dr, Shady Side, MD 20764
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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 $1,189,140

  Last Listing Agent Jennifer Chaney Chaney Homes, LLC

  1538 Robinson Rd, Shady Side, MD 20764
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  /22

  Est $387,522 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,120 Sq Ft

  1170 Maple Ave, Shady Side, MD 20764

  1170 Maple Ave, Shady Side, MD 20764
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  /39

  $300,000 Pending

  • 4 Beds
  • 2 Baths
  • 1,344 Sq Ft

  6070 Shady Side Rd, Shady Side, MD 20764

  Don't miss this wonderful opportunity to own this porch front home seated in an expansive private lot approximately 3.38 acres. Home features hardwood floors that flows from the combined living and dining rooms to the nice sized kitchen with appliances and main level bedroom and bath. There is a full bath on each level and three more bedrooms on the upper level. The sunroom with wide windows and

  Gina Gargeu Century 21 Downtown

  6070 Shady Side Rd, Shady Side, MD 20764
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  /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

  Last Listing Agent Ray Mudd Schwartz Realty, Inc.

  1208 Oak Ave, Shady Side, MD 20764
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  /39

  Est $620,139 Not Listed For Sale

  • 4 Beds
  • 3.5 Baths
  • 2,566 Sq Ft

  1004 Hawk Channel Ct, West River, MD 20778

  1004 Hawk Channel Ct, West River, MD 20778
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  /27

  $335,000

  • 3 Beds
  • 2.5 Baths
  • 1,512 Sq Ft

  1512 Lincoln Rd, Shady Side, MD 20764

  Home Sweet Home! Come tour this 2 level, 3 bedroom, 2 full bath just a couple blocks to the water. Situated in Columbia Beach, feel like you're vacationing year round! Whether your taking a walk in the gated community, or entertaining in the spacious home, you'll enjoy living here! No HOA. Please read agent remarks.

  Cheryl Bare CENTURY 21 New Millennium

  1512 Lincoln Rd, Shady Side, MD 20764
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  /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 $363,310

  Last Listing Agent Melanie Montague EXP Realty, LLC

  4871 Avery Rd, Shady Side, MD 20764
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  /23

  Est $458,649 Not Listed For Sale

  • 3 Beds
  • 2.5 Baths
  • 1,568 Sq Ft

  4961 Filbert St, Shady Side, MD 20764

  4961 Filbert St, Shady Side, MD 20764
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  /15

  $269,950

  • 3 Beds
  • 1.5 Baths
  • 1,320 Sq Ft

  1160 Oak Ave, Shady Side, MD 20764

  Offers cannot be submitted for seller review until 1/18/26. Set in a peaceful bayside community, this 3-bedroom, 1.5-bath home offers 1,320 square feet and the chance to create your vision near the water. The home features a rear deck and is within walking distance to the beach. The property requires substantial renovation and is priced accordingly. Sold As-Is with no repairs. A great opportunity

  Mike McCarthy Metro DMV Realty

  1160 Oak Ave, Shady Side, MD 20764
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  /23

  $480,000 Sold Feb 17, 2025

  1241 Avalon Blvd, Shady Side, MD 20764

  • 3 Beds
  • 2.5 Baths
  • 1,326 Sq Ft
  • Built 1993

  Last Sold Summary

  • $362/SF
  • 60 Days On Market

  Current Estimated Value $475,793

  Last Listing Agent DAVID LUCKE Turnock Real Est. Services, Inc.

  1241 Avalon Blvd, Shady Side, MD 20764
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  /47

  Est $1,140,702 Not Listed For Sale

  • 4 Beds
  • 3.5 Baths
  • 3,040 Sq Ft

  4816 Atwell Rd, Shady Side, MD 20764

  4816 Atwell Rd, Shady Side, MD 20764
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  /2

  $25,000

  • Land
  • 0.57 Acre
  • $43,860 per Acre

  0 Haile Pkwy Unit MDAA2127474, 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 MDAA2127474, Shady Side, MD 20764
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  /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 $1,083,142

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

  1323 Jordan Dr, Shady Side, MD 20764
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  /23

  Est $528,616 Not Listed For Sale

  • 3 Beds
  • 2.5 Baths
  • 1,748 Sq Ft

  6039 Shady Side Rd, Shady Side, MD 20764

  6039 Shady Side Rd, Shady Side, MD 20764
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  /8

  $239,500

  • Land
  • 8.19 Acres
  • $29,243 per Acre

  6118 Shady Side Rd, Shady Side, MD 20764

  Only 31k per acre! This wonderful 8.19 acre wooded level lot conveniently located to the Chesapeake & West River is loaded with potential & ready to build your dream home! Off a hard surface road this terrific property is just minutes to multiple marinas, yacht clubs & harbors, shopping, dining and just 25 minutes to Annapolis & 45 minutes to DC. Public water and sewer available

  Tem Popoola Real Broker, LLC

  6118 Shady Side Rd, Shady Side, MD 20764
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  /35

  $400,000 Sold Feb 13, 2025

  6320 Shady Side Rd, Shady Side, MD 20764

  • 3 Beds
  • 2.5 Baths
  • 1,196 Sq Ft
  • Built 1944

  Last Sold Summary

  • $334/SF
  • 17 Days On Market

  Current Estimated Value $407,282

  Last Listing Agent Thomas Gavin Coldwell Banker Realty

  6320 Shady Side Rd, Shady Side, MD 20764
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  /20

  Est $357,838 Not Listed For Sale

  • 2 Beds
  • 1 Bath
  • 1,083 Sq Ft

  1206 Holly Ave, Shady Side, MD 20764

  1206 Holly Ave, Shady Side, MD 20764
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  /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
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  /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 $955,656

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

  4927 Hine Dr, Shady Side, MD 20764
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  /24

  Est $396,696 Not Listed For Sale

  • 3 Beds
  • 1.5 Baths
  • 1,040 Sq Ft

  1172 Maple Ave, Shady Side, MD 20764

  1172 Maple Ave, Shady Side, MD 20764
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  /29

  $815,000 New Construction

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

  6512 Shady Side Rd, Shady Side, MD 20764

  For buyers desiring a quicker move-in, this same model is under construction less than a mile away and will be completed in approximately 30 days — a perfect opportunity to preview the craftsmanship and finishes in person. This to-be-built custom Arts & Crafts residence by local builder Laine Street Homes blends timeless design with modern luxury. Set on a premium 1.5-acre homesite, the property

  Joshua Mast HomeSource Pro Real Estate

  6512 Shady Side Rd, Shady Side, MD 20764
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  /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 $450,406

  Last Listing Agent Ronald Watson Flag Real Estate Inc.

  1192 Oak Ave, Shady Side, MD 20764
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  /75

  Est $1,225,852 Not Listed For Sale

  • 4 Beds
  • 3 Baths
  • 2,617 Sq Ft

  1326 W River Rd, Shady Side, MD 20764

  1326 W River Rd, Shady Side, MD 20764
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  /27

  $499,900

  • 4 Beds
  • 2.5 Baths
  • 2,176 Sq Ft

  1711 Columbia Beach Rd, Shady Side, MD 20764

  Nestled between serene waters, this home offers stunning, unobstructed views of Flag Pond from the rear and views of the Chesapeake Bay from the front. Enjoy watching local waterfowl and soaking in the natural beauty from every angle. Inside, the spacious kitchen opens to the family room, perfect for gathering, along with a formal living room and a main-level office or potential 5th bedroom.

  Ray Mudd Schwartz Realty, Inc.

  1711 Columbia Beach Rd, Shady Side, MD 20764
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  /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 $420,937

  Last Listing Agent Joshua Shapiro Douglas Realty, LLC

  5196 Chesapeake Ave, Shady Side, MD 20764
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  /33

  Est $480,496 Not Listed For Sale

  • 3 Beds
  • 2.5 Baths
  • 1,714 Sq Ft

  1016 Cosimano Place, West River, MD 20778

  1016 Cosimano Place, West River, MD 20778
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  /20

  $304,000 Pending

  • 3 Beds
  • 2.5 Baths
  • 1,500 Sq Ft

  4908 Aspen St, Shady Side, MD 20764

  Welcome to this 2-story home nestled in the serene Avalon Shores community. This home features 3 bedrooms, 2 full baths, and 1 half bath. Eat in kitchen with additional room for table space. The exterior boasts multi-level decks ideal for outdoor entertaining, a shady yard offering privacy, and spacious 2 car garage. Located in the peaceful Avalon Shores subdivision, this home is close to Anne

  Brenda Sarver Maryland Realty Connection

  4908 Aspen St, Shady Side, MD 20764
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  /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 $468,718

  Last Listing Agent Nicki Palermo RE/MAX One

  1233 Juniper St, Shady Side, MD 20764
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  /54

  Est $521,014 Not Listed For Sale

  • 4 Beds
  • 2.5 Baths
  • 1,870 Sq Ft

  1184 Holly Ave, Shady Side, MD 20764

  1184 Holly Ave, Shady Side, MD 20764
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  /45

  $395,000 Under Contract

  • 3 Beds
  • 2 Baths
  • 1,232 Sq Ft

  4929 Aspen St, Shady Side, MD 20764

  Move-in ready and recently updated, this bright rancher is located in a sought-after water-oriented community. Recent upgrades create a modern feel throughout, including new luxury vinyl plank flooring, an updated kitchen, two renovated full bathrooms, fresh interior paint, and new interior doors. The home offers a spacious primary bedroom with a private renovated full bath and dual closets. Two

  Lynne Ferrante Berkshire Hathaway HomeServices PenFed Realty

  4929 Aspen St, Shady Side, MD 20764
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  /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 $186,506

  Last Listing Agent Bill Beam Beam Realty Group, Inc.

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

  Est $472,994 Not Listed For Sale

  • 4 Beds
  • 2.5 Baths
  • 1,947 Sq Ft

  4718 Washington Ave, Shady Side, MD 20764

  4718 Washington Ave, Shady Side, MD 20764
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  /20

  $330,000

  • 2 Beds
  • 1 Bath
  • 960 Sq Ft

  1223 Pine Ave, Shady Side, MD 20764

  Welcome to this charming 2-bedroom home tucked away on a quiet street in the peaceful waterfront community of Shady Side. This inviting property offers a comfortable layout and a spacious yard, perfect for outdoor entertaining, gardening, or relaxing in a serene setting. Enjoy the coastal lifestyle with easy access to the Chesapeake Bay, nearby marinas, parks, and waterfront dining, all while

  Matthew Dubbaneh Samson Properties

  1223 Pine Ave, Shady Side, MD 20764
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  /54

  $465,000 Sold Feb 28, 2025

  1305 Maple St, Shady Side, MD 20764

  • 5 Beds
  • 2.5 Baths
  • 1,992 Sq Ft
  • Built 1992

  Last Sold Summary

  • $233/SF
  • 17 Days On Market

  Current Estimated Value $488,945

  Last Listing Agent Pattee McInerney Scott McInerney RE/MAX One

  1305 Maple St, Shady Side, MD 20764
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  /33

  Est $387,083 Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 1,285 Sq Ft

  1422 Columbia Beach Rd, Shady Side, MD 20764

  1422 Columbia Beach Rd, Shady Side, MD 20764
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  /5

  $145,000 Pending

  • Land
  • 0.17 Acre
  • $852,941 per Acre

  5314 Al Jones Dr, Shady Side, MD 20764

  Beautiful Chesapeake Bay property for sale! Don’t miss this rare opportunity to build your dream home in the quaint, gated community of Columbia Beach, a serene neighborhood offering breathtaking bay views. Enjoy coastal living with a private pier, boat ramp, playground, tennis and basketball courts, and pickleball. Perfect for boating, fishing, sailing, kayaking, or simply relaxing by the water

  Niesha Thomas NextHome Mims Realty Group

  5314 Al Jones Dr, Shady Side, MD 20764
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  /47

  $875,000 Sold May 02, 2025

  5070 Lerch Dr, Shady Side, MD 20764

  • 5 Beds
  • 3 Baths
  • 2,598 Sq Ft
  • Built 1956

  Last Sold Summary

  • $337/SF
  • 78 Days On Market

  Current Estimated Value $866,626

  Last Listing Agent Doc Keane Washington Fine Properties, LLC

  5070 Lerch Dr, Shady Side, MD 20764
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  /49

  Est $518,596 Not Listed For Sale

  • 3 Beds
  • 2.5 Baths
  • 1,964 Sq Ft

  6132 Shady Side Rd, Shady Side, MD 20764

  6132 Shady Side Rd, Shady Side, MD 20764
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  /15

  $997,000

  • Land
  • 1.6 Acres
  • $623,125 per Acre

  1133 Steamboat Rd, Shady Side, MD 20764

  BRING ON THE RIVER BOATS... Unparalleled access to the Chesapeake Bay, ideal for boating, sailing, fishing and crabbing enthusiasts!!! Discover the perfect canvas for your waterfront dream home on this stunning undeveloped lot in the prestigious Shady Side community offering ample space for building a custom waterfront estate. With 80 feet of prime waterfront frontage on the Chesapeake Bay, this

  John Halpin RE/MAX Premiere Selections

  1133 Steamboat Rd, Shady Side, MD 20764

Showing Results 81 - 120, Page 3 of 18