Shady Side, MD Homes

• 

  

  

  /60

  $449,000

  • 4 Beds
  • 2 Baths
  • 1,300 Sq Ft

  4738 Idlewilde Rd, Shady Side, MD 20764

  Amazing opportunity to own a beautifully remodeled home in the waterfront community of Idlewilde by the Bay in Shady Side. Just steps from the Chesapeake Bay, this 4-bedroom, 2-bath home offers approximately 1,300 square feet of modern living with a brand-new signature designer kitchen featuring an eat-in island, new appliances, and high-end finishes throughout.The spacious primary suite

  

  Jesse Marks

  Realinvestors Real Estate Services, LLC

  (410) 927-5552

  4738 Idlewilde Rd, Shady Side, MD 20764
• 

  

  

  /18

  $1,900 per month

  • 1 Bed
  • 1 Bath
  • 750 Sq Ft
  • Condo for Rent

  1012 S Creek View Ct, Churchton, MD 20733

  Stunning waterfront studio tucked away in a tranquil community on South Creek! Blending comfort, charm and lifestyle seamlessly, you may never leave! This studio offers a full updated kitchen with an eat in area with beautiful views of the water, a full sized washer and dryer and a private entrance to the patio. Upstairs offers a wonderful open concept studio designed for relaxation-a cozy

  Kelly Parks Coldwell Banker Realty

  1012 S Creek View Ct, Churchton, MD 20733
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  /28

  $340,000 Sold Oct 17, 2025

  • 1,088 Sq Ft
  • $312/SF
  • 4 Days On Market

  • 3 Beds
  • 1 Bath
  • Built 1965

  1197 Poplar Ave, Shady Side, MD 20764

  Charming one-level home tucked away in the waterfront community of Cedarhurst! This property is loaded with curb appeal, featuring newer navy-blue siding, a spacious driveway that easily fits 5+ cars, a welcoming front porch, and a fully fenced backyard that’s both flat and expansive & complete with a large storage shed. Inside, you’ll find 3 comfortable bedrooms and an updated full bathroom with

  Delaney Burgess RE/MAX United Real Estate

  1197 Poplar Ave, Shady Side, MD 20764
• 

  

  

  /39

  Est $640,355 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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  /70

  $515,000 Pending

  • 4 Beds
  • 2.5 Baths
  • 1,756 Sq Ft

  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

  (443) 234-8208

  4906 Lee Blvd, Shady Side, MD 20764
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  /63

  $5,000 per month

  • 3 Beds
  • 2.5 Baths
  • 2,360 Sq Ft
  • House for Rent

  4962 Lerch Dr, Shady Side, MD 20764

  AVAILABLE FURNISHED ($5000) or UNFURNISHED ($4,000/month) — just bring your personal belongings and settle in! Welcome to “Pier Joy” – Your SUNSATIONAL Waterfront Retreat! Turn-key, This stunning 3-bedroom, 2.5-bath on trend home is perfectly appointed with contemporary furnishings, linens, utensils, and some utilities included. Formerly a popular Airbnb, everyone RAVES about their stay in this

  Joan Stansfield Samson Properties

  4962 Lerch Dr, Shady Side, MD 20764
• 

  

  /27

  $449,950 Sold Oct 16, 2025

  • 1,224 Sq Ft
  • $368/SF
  • 8 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 1988

  1192 Oak Ave, Shady Side, MD 20764

  Come live the Chesapeake lifestyle!!! This amazing house features 3 bedrooms, 2 full baths, first and second floor bay windows, hardwood floors, remodeled kitchen with quality cabinetry, stainless appliances, space for a large table in the kitchen,1 car garage, front porch, rear wrap around deck, fire pit, newer shed, fenced XL yard (1.5 lots), a generous main driveway plus an additional driveway

  Ronald Watson Flag Real Estate Inc.

  1192 Oak Ave, Shady Side, MD 20764
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  /63

  Est $511,959 Not Listed For Sale

  • 4 Beds
  • 2.5 Baths
  • 1,914 Sq Ft

  1306 Butternut St, Shady Side, MD 20764

  1306 Butternut St, Shady Side, MD 20764
• 

  

  /14

  $54,900

  • Land
  • 1.53 Acres
  • $35,882 per Acre

  6152 Shady Side Rd, Shady Side, MD 20764

  1.53 Acre lot zoned R1 located in within Anne Arundel County in quiet Shady Side MD. Take a drive and see how this prime location can fulfill your needs! Owner Financing Available! Buyer to ascertain all necessary information for their intended use. Seller prefers Diana Khan of DK Law Group for Title and Closing.Property lines shown are approximate and need to be verified by purchaser.

  

  Kara Leddy

  Coldwell Banker Realty

  (410) 701-3561

  6152 Shady Side Rd, Shady Side, MD 20764
• 

  

  /49

  $2,200 per month

  • 2 Beds
  • 2 Baths
  • 840 Sq Ft
  • House for Rent

  4718 Frederick Ave, Shady Side, MD 20764

  This your chance to enjoy one of the Best-Kept Secrets of SOCO Maryland -- life by the Bay in Idlewilde!Tenants vacate this weekend, and it can be yours!Tucked away on the serene tip of the peninsula in Shady Side, MD, just 24 minutes from Annapolis, lies the charming and picturesque community of Idlewilde. This delightful, fully renovated bungalow/cottage is the perfect retreat,

  Joan Stansfield Samson Properties

  4718 Frederick Ave, Shady Side, MD 20764
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  /81

  $1,950,000 Sold Oct 16, 2025

  • 3,745 Sq Ft
  • $521/SF
  • 108 Days On Market

  • 4 Beds
  • 2.5 Baths
  • Built 2005

  1100 Steamboat Rd, Shady Side, MD 20764

  Spectacular West River waterfront! A serene lot with panoramic water views, a custom-built home that exudes coastal style, a private dock with two boat slips, a detached 3-car garage with a storage loft, a spacious yard for playing and entertaining, an exquisite vantage point for enjoying the area’s natural beauty, from waterfowl to sunsets. Welcome to 1100 Steamboat Road, offering the best of

  Kirsten Rowan Compass

  1100 Steamboat Rd, Shady Side, MD 20764
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  /30

  Est $500,623 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,786 Sq Ft

  1421 Snug Harbor Rd, Shady Side, MD 20764

  1421 Snug Harbor Rd, Shady Side, MD 20764
• 

  

  /47

  $674,900 Pending

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

  1195 Cedar Ave, Shady Side, MD 20764

  This beautifully crafted home blends timeless coastal charm with modern luxury. Featuring classic board and batten siding and a welcoming front porch, the exterior makes a striking first impression. Step inside to an open-concept layout that seamlessly connects the dining and family room, ideal for both everyday living and entertaining.At the heart of the home is a spacious kitchen

  

  Jamie Richardson

  RE/MAX United Real Estate

  (410) 724-1563

  1195 Cedar Ave, Shady Side, MD 20764
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  /90

  $1,100,000 Sold Oct 15, 2025

  • 2,671 Sq Ft
  • $412/SF
  • 2 Days On Market

  • 5 Beds
  • 3 Baths
  • Built 1940

  1323 Jordan Dr, Shady Side, MD 20764

  **OFFER DEADLINE SUNDAY SEPTEMBER 14th AT 6:00PM**OPEN HOUSES THIS WEEKEND ONLY, SATURDAY & SUNDAY 12pm to 5pm, Sept 13th & 14th** Wonderful waterfront on West River. Five bedrooms and three full baths in this modern open floor plan home with 9-foot ceilings and tranquil water views from nearly every room. The large, fenced yard keeps people and pets safe while beckoning you to the water's edge.

  Karlton Morris Long & Foster Real Estate, Inc.

  1323 Jordan Dr, Shady Side, MD 20764
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  /35

  Est $512,450 Not Listed For Sale

  • 4 Beds
  • 2.5 Baths
  • 1,960 Sq Ft

  5031 Lerch Dr, Shady Side, MD 20764

  5031 Lerch Dr, Shady Side, MD 20764
• 

  

  /49

  $449,000

  • 4 Beds
  • 2 Baths
  • 2,500 Sq Ft

  5840 Shady Side Rd, Churchton, MD 20733

  Just minutes from Franklin State Park, the West River, and the Chesapeake Bay, this 4-bedroom, 2-bath Churchton home captures the essence of relaxed coastal living. Whether you're drawn to peaceful waters, community piers, bayside dining, or quaint local shops, this location offers it all. Step inside to a spacious main level with warm wood flooring and architectural columns that subtly define

  Bob Lucido Keller Williams Lucido Agency

  5840 Shady Side Rd, Churchton, MD 20733
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  /4

  $420,000 Sold Oct 10, 2025

  • 934 Sq Ft
  • $450/SF
  • 0 Days On Market

  • 2 Beds
  • 2 Baths
  • Built 1986

  5196 Chesapeake Ave, Shady Side, MD 20764

  Stunning home situated with a direct, unobstructed waterview of the gorgeous Chesapeake Bay. Featuring 2 bedrooms and 2 full bathrooms, this one-level home offers a serene vacation getaway or full-time residence. Cedarhurst on the Bay is a wonderful community offering boat slips, a community hall, playgrounds and a pier!

  Joshua Shapiro Douglas Realty, LLC

  5196 Chesapeake Ave, Shady Side, MD 20764
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  /17

  Est $390,413 Not Listed For Sale

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

  1196 Bay View Ave, Shady Side, MD 20764

  1196 Bay View Ave, Shady Side, MD 20764
• 

  

  /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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  /67

  $1,000,000 Sold Oct 10, 2025

  • 3,244 Sq Ft
  • $308/SF
  • 67 Days On Market

  • 4 Beds
  • 2.5 Baths
  • Built 1936

  4715 Oak Rd, Shady Side, MD 20764

  Welcome to the Chesapeake Bay! Relax while sipping your morning coffee or unwinding with a glass of wine. This waterfront cottage offers over 3000 sf of living space with panoramic views from every room! Unique features include wood beams on the first and second levels; two staircases access the second level; authentic cedar doors, closets, and drawers take you back to the 1930s; while the

  Angie Carr Riverscape Realty

  4715 Oak Rd, Shady Side, MD 20764
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  /3

  Est $164,667 Not Listed For Sale

  1452 Shady Rest Rd, Shady Side, MD 20764

  1452 Shady Rest Rd, Shady Side, MD 20764
• 

  

  /43

  $489,999 Open Sat 11AM - 1PM

  • 3 Beds
  • 2.5 Baths
  • 1,784 Sq Ft

  1037 Biltmore Ave, West River, MD 20778

  Welcome to your new water-access home! This charming 3-bedroom, 2.5-bath property is move-in ready and waiting for its new owners. Step inside to find a spacious living room, a flexible large dining room that can also serve as a family room, and a large eat-in kitchen featuring upgraded countertops, a tiled backsplash, and stainless steel appliances. The flooring is newly installed, and the HVAC

  Dawn Marie Miller Coldwell Banker Realty

  1037 Biltmore Ave, West River, MD 20778
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  /26

  $525,000 Sold Sep 30, 2025

  • 1,806 Sq Ft
  • $291/SF
  • 35 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 1928

  4727 Oak Rd, Shady Side, MD 20764

  Rare Chesapeake Bay waterfront property with panoramic views and endless potential! This 3-bedroom, 2-bath home sits on a prime waterfront lot with a private pier, spacious yard, and mature landscaping. Enjoy sweeping Bay views from the sunroom, living room, and multiple bedrooms, along with the soothing sounds of the water just steps away.The home features charming wood ceilings, exposed

  Frank Gamez REMAX Platinum Realty

  4727 Oak Rd, Shady Side, MD 20764
• 

  

  /12

  Est $140,974 Not Listed For Sale

  1190 Steamboat Rd, Shady Side, MD 20764

  1190 Steamboat Rd, Shady Side, MD 20764
• 

  

  /56

  $699,000

  • 3 Beds
  • 3 Baths
  • 1,920 Sq Ft

  4922 Lerch Dr, Shady Side, MD 20764

  You can't beat the price for the WATERFRONT lifestyle in the Chesapeake Bay area! This stunning, RENOVATED open concept, 3-bedroom, 3-bath home was built in 2005 and has a PRIVATE dock -- blending modern updates, natural light, and serene water views. This home is the ideal size—not too big, not too small—offering the perfect balance of comfort, function, and privacy!Step inside an

  Joan Stansfield Samson Properties

  4922 Lerch Dr, Shady Side, MD 20764
• 

  

  /33

  $1,325,000 Sold Sep 30, 2025

  • 2,985 Sq Ft
  • $444/SF
  • 82 Days On Market

  • 3 Beds
  • 3 Baths
  • Built 1926

  1045 Back Bay Beach Rd, West River, MD 20778

  You said it HAD to be perfect. That you were NOT going to compromise. Good news! THIS is the one you've been waiting for, and it’s not every day that a home like this comes along. Perfectly positioned on a peaceful peninsula where the West River meets South Creek, this elegant retreat offers panoramic water views from every single room. No, really! EVERY. SINGLE. ROOM. From the moment you step

  Theresa Kurtz EXP Realty, LLC

  1045 Back Bay Beach Rd, West River, MD 20778
• 

  

  /39

  Est $546,354 Not Listed For Sale

  • 4 Beds
  • 2.5 Baths
  • 1,936 Sq Ft

  1220 Juniper St, Shady Side, MD 20764

  1220 Juniper St, Shady Side, MD 20764
• 

  

  /31

  $535,000

  • 3 Beds
  • 2 Baths
  • 2,024 Sq Ft

  4949 Idlewilde Rd, Shady Side, MD 20764

  This spacious and well-maintained home offers the ease of one-level living at it's best. The modern kitchen opens to a cozy family room featuring a gas fireplace and a sliding door that leads to a stunning sunroom and adjacent deck—perfect for relaxing or entertaining. Enjoy formal spaces with both a living room and dining room, along with a generous primary suite complete with a private full

  Ray Mudd Schwartz Realty, Inc.

  4949 Idlewilde Rd, Shady Side, MD 20764
• 

  

  /34

  $439,000 Sold Sep 29, 2025

  • 2,440 Sq Ft
  • $180/SF
  • 59 Days On Market

  • 4 Beds
  • 2 Baths
  • Built 1978

  1440 Cedarhurst Rd, Shady Side, MD 20764

  Welcome to 1440 Cedarhurst Road! This beautifully maintained home offers over 2,400 square feet of comfortable living space, featuring 4 bedrooms and 2 bathrooms on a spacious, flat lot.Step inside to discover gleaming hardwood and tile flooring throughout. The heart of the home is a spacious kitchen with a center island, seamlessly connected to an open dining area. Just off the kitchen,

  Terry McAllister RE/MAX One

  1440 Cedarhurst Rd, Shady Side, MD 20764
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  /37

  Est $487,957 Not Listed For Sale

  • 3 Beds
  • 2.5 Baths
  • 1,632 Sq Ft

  6318 Linden St, Shady Side, MD 20764

  6318 Linden St, Shady Side, MD 20764
• 

  

  /35

  $500,000

  • 3 Beds
  • 2.5 Baths
  • 1,784 Sq Ft

  1037 Biltmore Ave, West River, MD 20778

  Welcome to 1037 Biltmore Ave — A Waterfront Dream in West River!Nestled in the peaceful and picturesque community of West River, this beautifully maintained home offers the perfect blend of comfort, style, and coastal living. Just steps from the water and minutes to the Chesapeake Bay, this property is ideal for those who crave serenity without sacrificing convenience.This

  Matt Kalogeras Houwzer, LLC

  1037 Biltmore Ave, West River, MD 20778
• 

  

  /42

  $465,000 Sold Sep 26, 2025

  • 2,051 Sq Ft
  • $227/SF
  • 37 Days On Market

  • 5 Beds
  • 2.5 Baths
  • Built 1965

  1216 Grove Ave, Shady Side, MD 20764

  Chesapeake Bay views and close to the community dock and harbor! Feels like you are on vacation all year round! This home has 4 bedrooms 2.5 baths and a 3rd floor bonus room with balcony and Chesapeake Bay views! It can be used as a family room or a 5th bedroom! Owners suite also has a balcony with Bay views! Home has many new windows and the roof was replaced with Architectural shingles in

  Paul Lee Long & Foster Real Estate, Inc.

  1216 Grove Ave, Shady Side, MD 20764
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  /65

  Est $824,293 Not Listed For Sale

  • 3 Beds
  • 2.5 Baths
  • 3,946 Sq Ft

  5317 Birch Ct, West River, MD 20778

  5317 Birch Ct, West River, MD 20778
• 

  

  /32

  $480,000

  • 5 Beds
  • 2 Baths
  • 1,812 Sq Ft

  1220 Grove Ave, Shady Side, MD 20764

  This spacious 5 bedroom, 2 full bath split foyer is located in the highly desirable Community; Cedarhurst on the Bay. This remarkable property showcases the epitome of every day, vacation living with stunning views of The Chesapeake Bay. You will quickly be captivated by the grandeur that awaits you. The open layout seamlessly connects the living, dining and kitchen area, creating an ideal

  Jessica Gosman-Bowen Curtis Real Estate Company

  1220 Grove Ave, Shady Side, MD 20764
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  /84

  $335,000 Sold Sep 19, 2025

  • 1,160 Sq Ft
  • $289/SF
  • 13 Days On Market

  • 3 Beds
  • 1 Bath
  • Built 1930

  5031 Chalk Point Rd, West River, MD 20778

  Escape to this charming coastal cottage, a tranquil retreat just steps from South Creek and the West River and directly across from the West River Center. Enjoy peaceful mornings and memory-making evenings in this delightful riverside haven. Let the easy coastal setting inspire your imagination. With a “perfect 10” location and plenty of square footage, this is the ideal canvas for your

  Jeanette Silor Homesource United

  5031 Chalk Point Rd, West River, MD 20778
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  /53

  Est $421,189 Not Listed For Sale

  • 3 Beds
  • 1.5 Baths
  • 1,388 Sq Ft

  1727 Columbia Beach Rd, Shady Side, MD 20764

  1727 Columbia Beach Rd, Shady Side, MD 20764
• 

  

  /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
• 

  

  /42

  $450,000 Sold Sep 19, 2025

  • 2,464 Sq Ft
  • $183/SF
  • 16 Days On Market

  • 4 Beds
  • 2.5 Baths
  • Built 1968

  1347 W River Rd, Shady Side, MD 20764

  Welcome to 1347 W River Rd. – A Private Retreat on 2.02 Acres in Shady Side, MD. This two-story colonial offers privacy, space, and the perfect blend of classic charm and a few modern updates. With approx. 2,464 sq ft of living space, this 4-bedroom, 2.5-bath home provides ample room for everyday living and entertaining. Step into the spacious foyer and take in the warmth of the shaker-style

  Elizabeth DuLaney EXP Realty, LLC

  1347 W River Rd, Shady Side, MD 20764
• 

  

  /11

  Est $333,343 Not Listed For Sale

  • 3 Beds
  • 1 Bath
  • 864 Sq Ft

  5806 Shady Side Rd, Churchton, MD 20733

  5806 Shady Side Rd, Churchton, MD 20733
• 

  

  /3

  $554,500

  • 2 Beds
  • 1.5 Baths
  • 1,244 Sq Ft

  5211 Al Jones Dr, Shady Side, MD 20764

  Great New Price ... here is your chance to own and enjoy a coastal contemporary “cottage” with panoramic views and the soothing sounds of the Chesapeake Bay year round. This Bay fronting property has an open airy interior, warm and inviting, with two story vaulted ceilings, walls of windows which showcase the Bay view. The ease of main level living, enhanced with wood floors, includes the

  Celeste Blessin Coldwell Banker Realty

  5211 Al Jones Dr, Shady Side, MD 20764

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