Shady Side, MD Homes

• 

  

  

  /38

  Est $473,296 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,824 Sq Ft

  1195 Bayview Ave, Shady Side, MD 20764

  1195 Bayview Ave, Shady Side, MD 20764
• 

  

  

  /28

  $275,000

  • 2 Beds
  • 1 Bath
  • 1,000 Sq Ft

  4725 Idlewilde Rd, Shady Side, MD 20764

  Calling all investors, second-home seekers, and visionaries—this is the project you’ve been waiting for! AND it just got better with a price improvement!! Located just steps from the water in the charming community of Idlewilde, this 2-bedroom cottage-style home sits on a rare double lot with Chesapeake Bay views from the backyard and access to fantastic community amenities.While the

  Clinton Auman EXP Realty, LLC

  4725 Idlewilde Rd, Shady Side, MD 20764
• 

  

  

  /20

  $600,000 Sold Sep 12, 2025

  • 2,392 Sq Ft
  • $251/SF
  • 46 Days On Market

  • 4 Beds
  • 2.5 Baths
  • Built 1999

  1601 Snug Harbor Rd, Shady Side, MD 20764

  Charming and spacious colonial, situated on nearly 2 picturesque acres in Shady Side. Boasting 4 bedrooms and 2.5 bathrooms, this lovely home features a formal dining room, a spacious family room with a fireplace, and large sitting rooms off to the side, a finely appointed kitchen with granite counters and SS appliances, a large addition off the back of the home with vaulted ceilings and wood

  Alex Estill Long & Foster Real Estate, Inc.

  1601 Snug Harbor Rd, Shady Side, MD 20764
• 

  

  

  /22

  Est $385,363 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
• 

  

  

  /49

  $419,900

  • 3 Beds
  • 2 Baths
  • 1,456 Sq Ft

  4721 Girton Ave, Shady Side, MD 20764

  Perfect time to buy this updated home with a detached garage in the beautiful Chesapeake Bay front communnity of Idlewilde! Main level bedroom and full bathroom, waterview from front second level bedroom, and off street parking. This home has been completely updated with the main level having luxury vinyl flooring and fresh paint. The spacious kitchen has granite countertops, wood cabinets, and

  Sheri Stevens Samson Properties

  4721 Girton Ave, Shady Side, MD 20764
• 

  

  /34

  $400,000 Sold Sep 05, 2025

  • 1,120 Sq Ft
  • $357/SF
  • 1 Day On Market

  • 3 Beds
  • 2 Baths
  • Built 1989

  1228 Avalon Blvd, Shady Side, MD 20764

  Welcome to 1228 Avalon Boulevard, where top-tier renovations meet thoughtful design in every detail. From the moment you arrive, you'll appreciate the newly expanded driveway offering ample parking, complemented by a new paver walkway, meticulous landscaping, and a beautifully stained front deck.Step inside to an open-concept floor plan featuring brand new luxury vinyl plank flooring that

  Terry McAllister RE/MAX One

  1228 Avalon Blvd, Shady Side, MD 20764
• 

  

  /39

  Est $626,482 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
• 

  

  /5

  $150,000

  • Land
  • 4.03 Acres
  • $37,221 per Acre

  0 Shady Side Rd Unit MDAA2113156, Shady Side, MD 20764

  This beautiful four acre lot is heavily wooded, flat and level. Approximately 1,000' off the main road makes it very private and secluded. It abuts an additional four acre lot also available for sale. It is believed that because some of the property is in non-tidal wetlands that it cannot be subdivided but buyers should investigate with a civil engineer of choice to confirm. The access

  Sam Tanner Keller Williams Flagship

  0 Shady Side Rd Unit MDAA2113156, Shady Side, MD 20764
• 

  

  /34

  $335,000 Sold Sep 04, 2025

  • 1,060 Sq Ft
  • $316/SF
  • 3 Days On Market

  • 2 Beds
  • 1 Bath
  • Built 1989

  4925 Aspen St, Shady Side, MD 20764

  Enjoy coastal living without the high price in Avalon Shores. This water-oriented community offers boat ramp, a pier, private beaches, swimming area, & playgrounds. Quiet community with wonderful neighbors often riding bikes, golf carts or walking dogs. 2 bedrooms, 1 bath with addition off the master bedroom that would make the perfect office, exercise room or nursey. Kitchen updated, new

  Jaime Rollins CENTURY 21 New Millennium

  4925 Aspen St, Shady Side, MD 20764
• 

  

  /23

  Est $461,227 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
• 

  

  /35

  $725,000

  • 5 Beds
  • 3 Baths
  • 3,052 Sq Ft

  5235 Chalk Point Rd, West River, MD 20778

  This spacious 5-bedroom, 3-bathroom home offers the perfect blend of comfort, convenience, and Chesapeake Bay lifestyle. Located in highly sought-after Southern Anne Arundel County, this property sits just moments from the Bay, marinas, and local seafood favorites—ideal for those who love the water and small-town living. Step inside to find a bright open layout with generous living spaces,

  Bonnie O'Donnell RE/MAX One

  5235 Chalk Point Rd, West River, MD 20778
• 

  

  /27

  $565,000 Sold Sep 04, 2025

  • 1,152 Sq Ft
  • $490/SF
  • 69 Days On Market

  • 3 Beds
  • 1.5 Baths
  • Built 1985

  1605 Depriest Dr, Shady Side, MD 20764

  PURCHASE THIS BEAUTIFUL MOVE - IN READY HOME WITH 2 ATTACHED LOTS!! Incredible peninsula location with 180 degree WATER VIEWS of the Chesapeake Bay in the historical gated community of Columbia Beach in Shady Side , Maryland. This 2 level 3B/1.5 BA home is the perfect WEEKEND RETREAT and/or full time YEAR ROUND MAIN RESIDENCE. Great home to work remotely from and also a great location

  Lydia Newman Fairfax Realty Premier

  1605 Depriest Dr, Shady Side, MD 20764
• 

  

  /47

  Est $1,127,919 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
• 

  

  /6

  $259,999

  • Land
  • 0.77 Acre
  • $337,661 per Acre

  4846 Woods Wharf Rd, Shady Side, MD 20764

  Vacant Lot Ideal for Expansion or New Venture. Perfect for Boat Storage or New Building. Leverage its proximity to high-demand recreational areas for profitable boat and trailer storage, or business vehicles, or develop the lot into a commercial building for your business, or to lease the space to a business who is looking to serve the local community.

  Scott Cleary RE/MAX One

  4846 Woods Wharf Rd, Shady Side, MD 20764
• 

  

  /63

  $1,650,000 Sold Sep 03, 2025

  • 4,109 Sq Ft
  • $402/SF
  • 9 Days On Market

  • 5 Beds
  • 3 Baths
  • Built 1994

  1471 Nieman Rd, Shady Side, MD 20764

  Waterfront Paradise with Breathtaking Chesapeake Bay Views Welcome to your private waterfront retreat, nestled on a serene point along the West River with sweeping, panoramic views of the Chesapeake Bay. Just one hour from Washington, DC and without the hassle of crossing the Bay Bridge, this immaculate 5-bedroom, 3-bathroom home offers over 4,100 square feet of updated living space and

  Chris Craddock EXP Realty, LLC

  1471 Nieman Rd, Shady Side, MD 20764
• 

  

  /11

  Est $312,557 Not Listed For Sale

  • 3 Beds
  • 1 Bath
  • 1,166 Sq Ft

  1519 Lincoln Rd, Shady Side, MD 20764

  1519 Lincoln Rd, Shady Side, MD 20764
• 

  

  /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,

  John Halpin RE/MAX Premiere Selections

  1133 Steamboat Rd, Shady Side, MD 20764
• 

  

  /100

  $940,000 Sold Aug 29, 2025

  • 5,694 Sq Ft
  • $165/SF
  • 39 Days On Market

  • 5 Beds
  • 3.5 Baths
  • Built 1996

  1015 S Creek View Ct, Churchton, MD 20733

  Some homes impress you with features. This one leaves you with a feeling: luxury, elegance, features, form, utility, and most of all—home.Hidden in its own oasis of a quiet cul-de-sac, this home opens to sweeping, year-round water views—sunrises casting light across its front, golden-hour sunsets melting into the trees behind. It’s the kind of place that gives you permission to slow down

  Phil Gerdes Real Broker, LLC - Annapolis

  1015 S Creek View Ct, Churchton, MD 20733
• 

  

  /23

  Est $516,537 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
• 

  /2

  $40,000

  • Land
  • 0.34 Acre
  • $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

  $370,000 Sold Aug 29, 2025

  • 1,100 Sq Ft
  • $336/SF
  • 47 Days On Market

  • 3 Beds
  • 2.5 Baths
  • Built 1992

  1216 Hawthorne St, Shady Side, MD 20764

  Move-In Ready Coastal Gem in Shady Side – No HOA, Big Yard, and Modern Upgrades!Tucked away in a peaceful, water-oriented community just minutes from the Chesapeake Bay, this 3-bedroom, 2.5-bathroom home offers the perfect blend of charm and convenience. Enjoy recent updates including a new HVAC system, water heater, well pump & softener, electrical upgrades, and fresh paint — plus stylish

  TJ Alves Cummings & Co. Realtors

  1216 Hawthorne St, Shady Side, MD 20764
• 

  

  /20

  Est $352,335 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
• 

  /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,

  Joan Stansfield Samson Properties

  0 Haile Pkwy Unit MDAA2127474, Shady Side, MD 20764
• 

  

  /38

  $390,000 Sold Aug 29, 2025

  • 1,340 Sq Ft
  • $291/SF
  • 15 Days On Market

  • 3 Beds
  • 1.5 Baths
  • Built 1992

  1334 Jordan Dr, Shady Side, MD 20764

  Welcome to 1334 Jordan Drive, an adorably updated home nestled in the coveted waterfront community of Avalon Shores. With the perfect blend of modern elegance and functional design, this property offers a wonderful living experience. Gorgeous flooring flows seamlessly throughout, setting the stage for a home that exudes both warmth and sophistication. Walking in the front door you'll find an

  Susanne Modica Anne Arundel Properties, Inc.

  1334 Jordan Dr, Shady Side, MD 20764
• 

  

  /75

  Est $1,285,647 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
• 

  /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

  Joan Stansfield Samson Properties

  1436 Haile Pkwy, Shady Side, MD 20764
• 

  

  /65

  $710,000 Sold Aug 28, 2025

  • 3,352 Sq Ft
  • $212/SF
  • 64 Days On Market

  • 4 Beds
  • 4.5 Baths
  • Built 2011

  1109 Cherry Point Rd, West River, MD 20778

  First time on the market! This custom-built water view home, set on a picturesque one-acre lot, was thoughtfully designed by its original owners. Featuring a first-floor primary suite, wide hallways and doors for wheelchair accessibility, and a roll-in shower in the primary bath, every detail was carefully planned. The exquisite gourmet kitchen boasts a commercial gas stove, wall oven, spacious

  Ray Mudd Schwartz Realty, Inc.

  1109 Cherry Point Rd, West River, MD 20778
• 

  

  /33

  Est $460,711 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
• 

  /2

  $150,000

  • Land
  • 4.03 Acres
  • $37,221 per Acre

  0 Shady Side Rd Unit MDAA2113166, Shady Side, MD 20764

  This beautiful four acre lot is heavily wooded, flat and level. Approximately 1,000' off the main road makes it very private and secluded. It abuts an additional four acre lot also available for sale. It is believed that because some of the property is in non-tidal wetlands that it cannot be subdivided but buyers should investigate with a civil engineer of choice to confirm. The access

  Sam Tanner Keller Williams Flagship

  0 Shady Side Rd Unit MDAA2113166, Shady Side, MD 20764
• 

  

  /53

  $617,900 Sold Aug 27, 2025

  • 3,178 Sq Ft
  • $194/SF
  • 26 Days On Market

  • 4 Beds
  • 2.5 Baths
  • Built 2005

  4911 Lerch Dr, Shady Side, MD 20764

  Get ready to discover your Dream Home on the peaceful Shady Side Peninsula! A Welcoming and Spacious Colonial has hit the market, perfectly situated on a desirable Corner Lot within the serene, Water-oriented Community of Avalon Shores.This impressive 4-bedroom, 2.5 bath residence offers an idyllic Chesapeake Bay Lifestyle, just a few blocks from the community's private beach, playgrounds,

  Kara Leddy Coldwell Banker Realty

  4911 Lerch Dr, Shady Side, MD 20764
• 

  

  /54

  Est $536,652 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
• 

  /2

  $54,000

  • Land
  • 1.32 Acres
  • $40,909 per Acre

  1461 Cedarhurst Rd, Shady Side, MD 20764

  Escape the hustle and bustle of city life with this exceptional land opportunity in Shady Side, MD. Nestled in a tranquil community, this parcel offers the perfect setting to build your dream home surrounded by nature’s beauty. Enjoy the best of both worlds—peaceful seclusion with easy access to Route 2 and Route 4, making travel to Annapolis, Baltimore, and Washington, D.C., a breeze. Immerse

  Joan Stansfield Samson Properties

  1461 Cedarhurst Rd, Shady Side, MD 20764
• 

  

  /33

  $450,000 Sold Aug 27, 2025

  • 2,296 Sq Ft
  • $196/SF
  • 2 Days On Market

  • 5 Beds
  • 2 Baths
  • Built 1999

  1027 Biltmore Ave, West River, MD 20778

  Beautiful 5-Bedroom Home on One of the Largest Lots in the Community! This spacious and well-maintained home sits on an expansive lot and features a fully fenced backyard—perfect for entertaining or relaxing with family. Enjoy the large 2-year-old patio complete with a built-in fire pit and take comfort in the recently installed underground French drain system throughout the rear yard, designed

  Ray Mudd Schwartz Realty, Inc.

  1027 Biltmore Ave, West River, MD 20778
• 

  

  /43

  Est $462,407 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
• 

  

  /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
• 

  

  /77

  $800,000 Sold Aug 25, 2025

  • 2,918 Sq Ft
  • $274/SF
  • 0 Days On Market

  • 6 Beds
  • 3.5 Baths
  • Built 1992

  5312 Beauvoir Ct, West River, MD 20778

  Welcome to West River Estates—one of South County's most coveted waterfront communities!Step into your own private backyard paradise, featuring a saltwater pool with a jumping rock waterfall, dual patios, and a Trex deck—perfect for soaking up the sun or entertaining under the stars. The flat, fully fenced yard backs to peaceful woods, offering a serene setting with plenty of space for

  Dawn Marie Miller Coldwell Banker Realty

  5312 Beauvoir Ct, West River, MD 20778
• 

  

  /33

  Est $383,661 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
• 

  

  /24

  $1,524,000 New Construction

  • 4 Beds
  • 3.5 Baths
  • 3,727 Sq Ft

  5235 Al Jones Dr, Shady Side, MD 20764

  To be built by Whitehall Building & Co., Annapolis’ largest luxury waterfront builder. Located in the desirable Columbia Beach neighborhood, this coastal-style home will offer 3,700 sqft of living space and the rare combination of panoramic Chesapeake Bay views with the protection of a cove-front setting. Designed for modern waterfront living, the open-concept layout features soaring 10' ceilings

  Lynn Peaper Hubble Bisbee Christie's International Real Estate

  5235 Al Jones Dr, Shady Side, MD 20764
• 

  

  /46

  $1,185,000 Sold Aug 22, 2025

  • 3,216 Sq Ft
  • $368/SF
  • 49 Days On Market

  • 4 Beds
  • 3.5 Baths
  • Built 1996

  1012 S Creek View Ct, Churchton, MD 20733

  Ideally situated on 1+ acre of land with 126 feet of South Creek waterfrontage, this stunning custom-built home is private and peaceful. The well-maintained community of South Creek View, with 32 homes, welcomes you with mature trees and landscaped yards. The private pier has 4-5 ft water depth and two boat slips, a boat lift, and a lounging platform. Located on the pristine South Creek, you are

  Reid Buckley Long & Foster Real Estate, Inc.

  1012 S Creek View Ct, Churchton, MD 20733
• 

  

  /55

  Est $406,277 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,056 Sq Ft

  1509 Wright Rd, Shady Side, MD 20764

  1509 Wright Rd, Shady Side, MD 20764

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