Shady Side, MD Homes

• 

  

  

  /49

  Est $520,515 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
• 

  

  

  /77

  $770,000 Pending

  • 5 Beds
  • 3.5 Baths
  • 3,553 Sq Ft

  676 Plantation Blvd, West River, MD 20778

  Welcome home to this stunning 5-bedroom, 3.5-bath Colonial nestled in a highly desirable neighborhood featuring sidewalks, walking trails, and water access. Enjoy the charm of a huge front porch, ideal for relaxing evenings or morning coffee. Inside, you’ll find professionally refinished oak floors throughout the main level, new carpet upstairs, and an inviting layout perfect for family living.

  Jamie Spindle Curtis Real Estate Company

  676 Plantation Blvd, West River, MD 20778
• 

  

  

  /70

  $510,000 Sold Aug 20, 2025

  • 1,756 Sq Ft
  • $290/SF
  • 123 Days On Market

  • 4 Beds
  • 2.5 Baths
  • Built 2005

  4906 Lee Blvd, Shady Side, MD 20764

  **Move-in ready home in the private, water-privileged Westelee community of Avalon Shores**Access to beach, boat ramp, boat slips with electric, kayak rack, new waterfront playground and gazebo **Owner Suite on main level with walk in closet and private bath **Open cathedral ceilings in family room with cozy gas Fireplace and 8' double windows for abundant natural light **Hardwood floors

  Sandy Wing RE/MAX Leading Edge

  4906 Lee Blvd, Shady Side, MD 20764
• 

  

  

  /79

  Est $882,009 Not Listed For Sale

  • 3 Beds
  • 4.5 Baths
  • 1,888 Sq Ft

  5060 Lerch Dr, Shady Side, MD 20764

  5060 Lerch Dr, Shady Side, MD 20764
• 

  

  

  /11

  $169,900 Pending

  • Land
  • 0.14 Acre
  • $1,213,571 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
• 

  

  /71

  $1,190,000 Sold Aug 18, 2025

  • 2,060 Sq Ft
  • $578/SF
  • 142 Days On Market

  • 3 Beds
  • 2.5 Baths
  • Built 2014

  1538 Robinson Rd, Shady Side, MD 20764

  OPEN Bay-front at this STUNNING Custom Coastal with private pier, Located in coveted Columbia Beach, this airy WATERFRONT is a head-turner, boasting an open floor-plan, with the finest of finishes! Direct Chesapeake Bay location, 100' private pier & 3 jet-ski lifts makes this the perfect retreat - or year round treat- With 3 spacious bedrooms, 2.5 beautiful baths, 9' ceilings & hickory flooring-

  Jennifer Chaney Chaney Homes, LLC

  1538 Robinson Rd, Shady Side, MD 20764
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  /26

  Est $415,145 Not Listed For Sale

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

  1210 Oak Ave, Shady Side, MD 20764

  1210 Oak Ave, Shady Side, MD 20764
• 

  

  /86

  $1,050,000 Pending

  • 4 Beds
  • 4.5 Baths
  • 3,432 Sq Ft

  4992 Lerch Dr, Shady Side, MD 20764

  WATERFRONT LUXURY LIVING with panoramic West River views & unbelievable sunsets! This "3-year-young" custom home is perfectly positioned in the highly coveted community of Shady Side!! Designed for seamless indoor-outdoor coastal living. From the moment you step through the front door, the open-concept design draws your eye straight through to the water & pier — where your dock, boat lift, and

  Joan Stansfield Samson Properties

  4992 Lerch Dr, Shady Side, MD 20764
• 

  

  /18

  $321,000 Sold Aug 15, 2025

  • 960 Sq Ft
  • $334/SF
  • 1 Day On Market

  • 3 Beds
  • 1 Bath
  • Built 1980

  1179 Maple Ave, Shady Side, MD 20764

  Adorable home at a great price! This home has a great wrap around deck, nice yard and 2 sheds. Just a walk away from the community area/bay. Newer frig & stove, HVAC & water softener. Hardwood floors. Great starter OR downsizer home! Don't miss out...Priced to sell !

  Tonia Parent RE/MAX United Real Estate

  1179 Maple Ave, Shady Side, MD 20764
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  /16

  Est $312,322 Not Listed For Sale

  • 2 Beds
  • 1 Bath
  • 880 Sq Ft

  5312 Al Jones Dr, Shady Side, MD 20764

  5312 Al Jones Dr, Shady Side, MD 20764
• 

  

  /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
• 

  

  /51

  $389,000 Sold Aug 15, 2025

  • 1,407 Sq Ft
  • $276/SF
  • 21 Days On Market

  • 3 Beds
  • 1 Bath
  • Built 1940

  4977 Lerch Dr, Shady Side, MD 20764

  Discover your own slice of water-view paradise at 4977 Lerch Drive—a lovingly maintained 3-bedroom, 1-bath retreat just steps from the West River. Every corner of this home reflects the care and attention poured in by its current owner, from the bright, open-concept living spaces to the thoughtful updates throughout the interior Step inside to 1,407 sq ft of refreshed living space, where an

  Suebina Wong Douglas Realty, LLC

  4977 Lerch Dr, Shady Side, MD 20764
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  /62

  Est $478,533 Not Listed For Sale

  • 3 Beds
  • 2.5 Baths
  • 1,540 Sq Ft

  1345 Jordan Dr, Shady Side, MD 20764

  1345 Jordan Dr, Shady Side, MD 20764
• 

  /2

  $65,000 Pending

  • Land
  • 4.75 Acres
  • $13,684 per Acre

  5365 Deale Churchton Rd, Churchton, MD 20733

  Joseph Butcher Long & Foster Real Estate, Inc.

  5365 Deale Churchton Rd, Churchton, MD 20733
• 

  

  /43

  $449,900 Sold Aug 15, 2025

  • 1,904 Sq Ft
  • $236/SF
  • 8 Days On Market

  • 4 Beds
  • 2.5 Baths
  • Built 1990

  1207 Avalon Blvd, Shady Side, MD 20764

  Welcome to this classic colonial, nestled in the desirable water-privileged community of Avalon Shores! A wide covered front porch spans the entire front of the home, creating the perfect spot to sit and unwind in the evenings and chat with neighbors, or enjoy a quiet cup of coffee. This estate sale is being sold as-is, yet the home is in solid condition, simply awaiting a few personal touches

  Mary Gatton Redfin Corp

  1207 Avalon Blvd, Shady Side, MD 20764
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  /44

  Est $467,456 Not Listed For Sale

  • 3 Beds
  • 2.5 Baths
  • 1,544 Sq Ft

  1229 Holly Ave, Shady Side, MD 20764

  1229 Holly Ave, Shady Side, MD 20764
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  /2

  $39,000 Pending

  • Land
  • 0.21 Acre
  • $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
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  /61

  $402,500 Sold Aug 11, 2025

  • 1,364 Sq Ft
  • $295/SF
  • 6 Days On Market

  • 4 Beds
  • 3 Baths
  • Built 1983

  4723 Washington Ave, Shady Side, MD 20764

  This home has it all! Updated eat in kitchen with granite counters & stainless appliances. Roof replaced within the last 10 years. HVAC replace with Trane System in 2020. 6ft tall privacy fence for your double lot rear yard with deck. Walk to the community pier & water access one block away. While home has been freshly painted. Primary suite with additional sitting area & private full bath with

  Nicki Palermo RE/MAX One

  4723 Washington Ave, Shady Side, MD 20764
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  /50

  Est $550,167 Not Listed For Sale

  • 4 Beds
  • 3.5 Baths
  • 2,012 Sq Ft

  4940 W End Ave, Shady Side, MD 20764

  4940 W End Ave, Shady Side, MD 20764
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  /6

  $375,000 Pre-Foreclosure

  • 3 Beds
  • 2 Baths
  • 1,408 Sq Ft

  4900 Thomas Dr, Shady Side, MD 20764

  Just two doors from the water and steps from a children’s park and boat ramp, this 3-bedroom, 2-bath rancher offers 1,408 sq. ft. of potential. Renovations are underway with many improvements already complete—kitchen updates started, dishwasher included but not yet installed, and bedrooms ready for new flooring. New flooring will be installed throughout the home prior to closing, offering buyers

  Shannon Thayer Douglas Realty, LLC

  4900 Thomas Dr, Shady Side, MD 20764
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  /33

  $925,000 Sold Aug 08, 2025

  • 3,445 Sq Ft
  • $269/SF
  • 127 Days On Market

  • 4 Beds
  • 2.5 Baths
  • Built 1993

  4927 Hine Dr, Shady Side, MD 20764

  Post & beam architect design home with passive solar elements and lots of glass facing the water. A beautiful waterfront lot with southern exposure and wonderful view! Very well protected water on West River, stone rip rap. Pier only a few years old. 5 feet depth at average low tide. Hop in your boat and be at one of 2 waterfront restaurants or West River Sailing Club in a couple of minutes.

  William Whitman Long & Foster Real Estate, Inc.

  4927 Hine Dr, Shady Side, MD 20764
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  /55

  Est $512,784 Not Listed For Sale

  • 5 Beds
  • 3 Baths
  • 2,220 Sq Ft

  4727 Frederick Ave, Shady Side, MD 20764

  4727 Frederick Ave, Shady Side, MD 20764
• 

  

  /34

  $325,000 Under Contract

  • 2 Beds
  • 1 Bath
  • 900 Sq Ft

  1731 Columbia Beach Rd, Shady Side, MD 20764

  Beautiful updated coastal cottage in the heart of Columbia Beach! *New roof 2023* This move-in ready 2-bedroom home features hardwood floors, a brand-new kitchen with stainless steel appliances, quartz countertops, and updated cabinets. Amazing loft area inside. Enjoy skylights and beautiful views. Beautifully landscaped level lot with a spacious back deck ideal for relaxing or entertaining.

  Jose Salvador Rivera Jr RE/MAX Excellence Realty

  1731 Columbia Beach Rd, Shady Side, MD 20764
• 

  

  /36

  $398,000 Sold Aug 07, 2025

  • 1,354 Sq Ft
  • $294/SF
  • 5 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 1997

  6040 Shady Side Rd, Shady Side, MD 20764

  Charming 3-Bedroom Home in Quaint Shady Side, MDWelcome to this lovely 3-bedroom, 2 full-bath home nestled in the heart of Shady Side! Perfectly blending comfort, convenience, and outdoor charm, this well-maintained property is a rare find.Step outside to your huge fenced-in backyard, ideal for gatherings, play, or peaceful relaxation. Enjoy evenings around the cozy fire pit, or

  Theresa Mills Home Towne Real Estate

  6040 Shady Side Rd, Shady Side, MD 20764
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  /49

  Est $454,919 Not Listed For Sale

  • 4 Beds
  • 2.5 Baths
  • 1,728 Sq Ft

  1213 Grove Ave, Shady Side, MD 20764

  1213 Grove Ave, Shady Side, MD 20764
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  /10

  $229,999 Under Contract

  • Land
  • 15.59 Acres
  • $14,753 per Acre

  5162 Cedarlea Dr, West River, MD 20778

  Rare find of 15+ acres in West River. Public hook up for sewer is approved. Buyer must verify information from the plat with the county.

  Edith Marie Simpson Long & Foster Real Estate, Inc.

  5162 Cedarlea Dr, West River, MD 20778
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  /3

  $255,500 Sold Aug 05, 2025

  • 1,794 Sq Ft
  • $142/SF
  • 18 Days On Market

  • 3 Beds
  • 1 Bath
  • Built 1940

  5027 Chalk Point Rd, West River, MD 20778

  This porchfront home, located in the water-oriented community of Back Bay Beach, offers 1,794 square feet of living space and has 3 bedrooms, 1 full bathroom, spacious living room, a nice sized kitchen with appliances and a detached garage. Home is not only close to both West River and South Creek but also has easy access to piers, marina and West River Center.

  Gina Gargeu Century 21 Downtown

  5027 Chalk Point Rd, West River, MD 20778
• 

  

  /31

  Est $540,333 Not Listed For Sale

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

  1006 Allen Ave, West River, MD 20778

  1006 Allen Ave, West River, MD 20778
• 

  

  /30

  $349,900 Under Contract

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

  4913 Chestnut St, Shady Side, MD 20764

  Don’t miss this wonderful opportunity to own a well-maintained home at an affordable price! This inviting property features a spacious living/dining room combo with soaring cathedral ceilings that create an open, airy feel. The primary bedroom includes a full en-suite bath and sliding doors that lead to your private deck—perfect for enjoying the large, fully fenced backyard. The kitchen boasts

  Ray Mudd Schwartz Realty, Inc.

  4913 Chestnut St, Shady Side, MD 20764
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  /35

  $530,000 Sold Jul 31, 2025

  • 2,058 Sq Ft
  • $258/SF
  • 5 Days On Market

  • 4 Beds
  • 2.5 Baths
  • Built 1964

  1041 Harding Blvd, West River, MD 20778

  Single-Level Living at Its Finest! This beautifully renovated home (2021/2022) offers modern comfort and style with no detail overlooked. The upgraded kitchen features a large center island, granite countertops, white cabinetry, a double wall oven, cooktop, and recessed lighting throughout. Enjoy new flooring, custom trim work, a new furnace, new windows, and a new roof—everything has been done

  Ray Mudd Schwartz Realty, Inc.

  1041 Harding Blvd, West River, MD 20778
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  /40

  Est $1,660,689 Not Listed For Sale

  • 5 Beds
  • 5 Baths
  • 4,179 Sq Ft

  1243 Bast Ln, Shady Side, MD 20764

  1243 Bast Ln, Shady Side, MD 20764
• 

  

  /17

  $349,870 Under Contract

  • Land
  • 0.15 Acre
  • $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
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  /51

  $465,000 Sold Jul 30, 2025

  • 1,838 Sq Ft
  • $253/SF
  • 5 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 1990

  4722 Oak Rd, Shady Side, MD 20764

  This charming 3 bedroom, 2 bath rancher offers 1,838 square feet of beautifully updated living space on a peaceful bay‐block lot. The layout is simple and smart—one level, no stairs, with a bright open living space, updated kitchen, and cozy bedrooms tucked away for privacy.The kitchen was fully renovated in 2018 and features a center island, plenty of counter space, and all the modern

  Jan Crowley Compass

  4722 Oak Rd, Shady Side, MD 20764
• 

  

  /27

  Est $488,354 Not Listed For Sale

  • 3 Beds
  • 2.5 Baths
  • 1,788 Sq Ft

  4722 Girton Ave, Shady Side, MD 20764

  4722 Girton Ave, Shady Side, MD 20764
• 

  

  /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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  /26

  $530,000 Sold Jul 29, 2025

  • 1,980 Sq Ft
  • $268/SF
  • 11 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 1960

  1216 Steamboat Rd, Shady Side, MD 20764

  Welcome to Shady Side on the Western bank of The Chesapeake Bay. Much more affordable than Annapolis to the north and way more relaxed and chill. All the benefits of The Chesapeake Bay and still convenient to The District, Baltimore and The Eastern Shore. We’ve just completed a thorough rehab of this wonderful rancher that sets far back off of the street and offers a 2 car detached garage, rear

  Jon Leary Cummings & Co. Realtors

  1216 Steamboat Rd, Shady Side, MD 20764
• 

  

  /41

  Est $568,052 Not Listed For Sale

  • 3 Beds
  • 3.5 Baths
  • 2,081 Sq Ft

  1240 W River Rd, Shady Side, MD 20764

  1240 W River Rd, Shady Side, MD 20764
• 

  

  /39

  $300,000

  • 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
• 

  

  /44

  $420,000 Sold Jul 25, 2025

  • 1,648 Sq Ft
  • $255/SF
  • 5 Days On Market

  • 4 Beds
  • 2 Baths
  • Built 1940

  1181 Cedar Ave, Shady Side, MD 20764

  Welcome to 1181 Cedar Ave, situated in the tranquil water privileged community of Cedarhurst on the Bay! This charming home features 4 spacious bedrooms and 2 well-appointed bathrooms, offering both comfort and style. The floor plan is highlighted by an open living space right off of the kitchen area, complimented by a custom-built kitchen galley kitchen and dining area. A full bathroom is

  Ben Miller Synergy Realty

  1181 Cedar Ave, Shady Side, MD 20764
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  /103

  Est $2,214,237 Not Listed For Sale

  • 5 Beds
  • 4.5 Baths
  • 6,100 Sq Ft

  1258 W River Rd, Shady Side, MD 20764

  1258 W River Rd, Shady Side, MD 20764

Showing Results 121 - 160, Page 4 of 18