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Shady Side, MD Homes for Sale

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  • /68

    $515,000

    • 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

    Agent Photo

    Sandy Wing

    RE/MAX Leading Edge

    (443) 234-8208

    4906 Lee Blvd, Shady Side, MD 20764
  • /6

    $649,900 Coming Soon

    • 4 Beds
    • 2.5 Baths
    • 3,178 Sq Ft

    4911 Lerch Dr, Shady Side, MD 20764

    Coming Soon: Expansive Colonial in Water-Oriented Avalon Shores!Get ready to discover your dream home! A welcoming and spacious Colonial is soon to hit the market, perfectly situated on a desirable corner lot within the serene, water-oriented community of Avalon Shores on the peaceful Shady Side Peninsula.This impressive 4-bedroom, 3-bath residence offers an idyllic Chesapeake Bay Lifestyle, just

    Agent Photo

    Kara Leddy

    Coldwell Banker Realty

    (410) 421-7593

    4911 Lerch Dr, Shady Side, MD 20764
  • /27

    $603,000

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

    1605 Depriest Dr, Shady Side, MD 20764

    HONEY STOP THE CAR!!! It's better at the Beach! Incredible peninsula location with 180 degree views of the Chesapeake Bay in the gated community of Columbia Beach in Shady Side , Maryland. This 2 level 3B/1.5 BA home with an inverted floor plan is the perfect weekend retreat or full time main residence. Vacation every day! You can see the Chesapeake Bay Bridge on clear days right from your

    Lydia Newman Fairfax Realty Premier

    1605 Depriest Dr, Shady Side, MD 20764
  • /65

    $799,900

    • 4 Beds
    • 4.5 Baths
    • 3,352 Sq Ft

    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
  • /20

    $599,999

    • 4 Beds
    • 2.5 Baths
    • 2,392 Sq Ft

    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
  • /26

    $729,000

    • 2 Beds
    • 1.5 Baths
    • 1,540 Sq Ft

    4801 Avery Rd, Shady Side, MD 20764

    Water! Water everywhere! This adorable mid-century cottage faces Hopkins Cove , borders Parish Creek and looks out to the Chesapeake Bay Bridge. It is a dream come true for those who love living on the water, and could be your weekend getaway cottage. Not a fan of cottages? Then, go all in and remodel to make it your own! The possibilities are endless..... The property is being sold "as is".

    Theresa Kurtz EXP Realty, LLC

    4801 Avery Rd, Shady Side, MD 20764
  • /30

    $578,102

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

    5211 Al Jones Dr, Shady Side, MD 20764

    Newly priced and ready for summer, here is your chance to own and enjoy a coastal contemporary “cottage” with panoramic views and the soothing sounds of the Chesapeake Bay. 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
  • /35

    $789,000

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

    5235 Chalk Point Rd, West River, MD 20778

    Step into timeless elegance with this beautifully updated 5-bedroom, 3-bath Colonial, offering over 3,000 sq ft of thoughtfully designed living space on a private 1.37-acre lot. Perfectly positioned in the coveted West River community, this home delivers the ideal blend of space, style, and convenience.Built in 1990 and freshly enhanced throughout, this home boasts:Two spacious primary

    Bonnie O'Donnell RE/MAX One

    5235 Chalk Point Rd, West River, MD 20778
  • /33

    $999,900

    • 4 Beds
    • 2.5 Baths
    • 3,445 Sq Ft

    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. Hop in your boat and be at one of 2 waterfront restaurants or West River Sailing Club in a couple of minutes. You can join Chesapeake Yacht Club

    William Whitman Long & Foster Real Estate, Inc.

    4927 Hine Dr, Shady Side, MD 20764
  • /10

    $600,000

    • 2 Beds
    • 1 Bath
    • 862 Sq Ft

    1337 W River Rd, Shady Side, MD 20764

    Price Reduction!!Your Own Private Retreat, get away from the Rat Race and make this a great place for you and your family.1337 West River Road , located in Shady Side, MDis a secluded waterfront property that sits on 1.5 acres with 592 feet of waterfront on the South Creek.This property has a home with 2 beds and 1 bath that will need remodeling and/or teardown.it's located 1/4 mile off the main

    Bruce Thompson Long & Foster Real Estate, Inc.

    1337 W River Rd, Shady Side, MD 20764
  • /41

    $765,000

    • 4 Beds
    • 1.5 Baths
    • 2,144 Sq Ft

    1462 Snug Harbor Rd, Shady Side, MD 20764

    4 beds/ 1 full bath and 1/2 bath with shower.2144 SQ FT. Home and income opportunity goes with this four bedroom home on .57 acres of (C1B) commercial zoned property. Additional .375 acres and .1243 acres of (MA2) marine zoned property, totaling 1.0693 acres, with 135 feet of bulk headed waterfront, 200 foot pier, and 12 boat slips. Water depth from 4 to 8feet, that can accommodate boats in

    George Heine Schwartz Realty, Inc.

    1462 Snug Harbor Rd, Shady Side, MD 20764
  • /62

    $599,000

    • 3 Beds
    • 2.5 Baths
    • 1,839 Sq Ft

    1203 Cove Dr, Churchton, MD 20733

    Coastal Colonial with Water Views and secluded Pier Access in Sought-After Franklin Manor Beach! Enjoy the Chesapeake Bay lifestyle in this well-maintained Coastal Colonial, offering serene views of Deep Cove Creek and easy access to the water via a secluded pier—ideal for launching kayaks or a small boat. Nestled in a tranquil, natural setting, the home is part of a vibrant waterfront community

    Susan Cahill-Tully Compass

    1203 Cove Dr, Churchton, MD 20733
  • /34

    $469,900

    • 4 Beds
    • 2 Baths
    • 2,440 Sq Ft

    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, enjoy a

    Terry McAllister RE/MAX One

    1440 Cedarhurst Rd, Shady Side, MD 20764
  • /42

    $499,620

    • 5 Beds
    • 2.5 Baths
    • 2,051 Sq Ft

    1216 Grove Ave, Shady Side, MD 20764

    Recent Price reduction! 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

    Paul Lee Long & Foster Real Estate, Inc.

    1216 Grove Ave, Shady Side, MD 20764
  • /31

    $335,000

    • 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! 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 property needs renovation—including electric installation,

    Clinton Auman EXP Realty, LLC

    4725 Idlewilde Rd, Shady Side, MD 20764
  • /18

    $384,000

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

    1617 Winters Ave, Shady Side, MD 20764

    Welcome to 1617 Winters Ave – Coastal Charm with Modern Updates in Idlewild on the BayBeautifully updated and move-in ready, this 3-bedroom, 2-bath gem is nestled in the water-access community of Idlewild on the Bay. Situated just one block from the Chesapeake Bay, this home boasts fresh interior updates, a fully fenced yard, and two spacious decks ideal for entertaining or relaxing by the

    John Kreamer Taylor Properties

    1617 Winters Ave, Shady Side, MD 20764
  • /21

    $389,990

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

    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 new

    TJ Alves Cummings & Co. Realtors

    1216 Hawthorne St, Shady Side, MD 20764
  • /17

    $349,870

    • 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
  • /34

    $1,750,000

    • 3 Beds
    • 3 Baths
    • 2,985 Sq Ft

    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
  • /84

    $2,450,000

    • 4 Beds
    • 2.5 Baths
    • 3,745 Sq Ft

    1100 Steamboat Rd, Shady Side, MD 20764

    Imagine: welcoming friends and guests as they approach your home by powerboat, sailboat, or stand-up paddleboard; greeting osprey as they return to their annual nesting spot to raise their young each spring; watching Wednesday night sailboat racers make their way out of the river; relishing spectacular year-round sunsets…And now imagine enjoying this incredible backdrop from the comfort of your

    Kirsten Rowan Compass

    1100 Steamboat Rd, Shady Side, MD 20764
  • /41

    $399,000

    • 2 Beds
    • 2 Baths
    • 1,027 Sq Ft

    1215 Pine Ave, Shady Side, MD 20764

    Location, location, location! Just blocks from the sparkling Chesapeake Bay, this Shady Side gem is cute as can be and full of charm. This 2-bedroom, 2-bath home is flooded with natural light and features cathedral & vaulted ceilings, exposed beams, two brick fireplaces, and luxury vinyl plank flooring throughout. The kitchen opens up to a spacious, versatile room that can serve as a dining room

    Joan Stansfield Samson Properties

    1215 Pine Ave, Shady Side, MD 20764
  • /69

    $2,395,000

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

    4819 Avery Rd, Shady Side, MD 20764

    Discover unparalleled luxury in this stunning Five bedroom, four and half bath waterfront home, offering two hundred and seventy feet of private shoreline and breathtaking views. Designed for refined living and effortless entertaining, this home delivers an exceptional lifestyle both inside and out. The exterior is a private resort, featuring a heated in-ground pool, outdoor grilling area, fire

    Adam Light Monument Sotheby's International Realty

    4819 Avery 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
  • /46

    $1,195,000

    • 4 Beds
    • 3.5 Baths
    • 3,216 Sq Ft

    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
  • /42

    $515,620

    • 5 Beds
    • 2.5 Baths
    • 2,051 Sq Ft

    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
  • /2

    $100,000

    • Land
    • 0.68 Acre
    • $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

    Joan Stansfield Samson Properties

    1445 & 1447 Haile Pkwy, Shady Side, MD 20764
  • /2

    $65,000

    • Land
    • 0.30 Acre
    • $216,667 per Acre

    1408 & 1410 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 & Route 4, commuting to Annapolis, Baltimore, or Washington, D.C.,

    Joan Stansfield Samson Properties

    1408 & 1410 Haile Pkwy, Shady Side, MD 20764
  • /11

    $179,900

    • Land
    • 0.14 Acre
    • $1,285,000 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

    Jennifer Koenig Long & Foster Real Estate, Inc.

    5250 Al Jones Dr, Shady Side, MD 20764
  • /61

    $1,250,000

    • 3 Beds
    • 2.5 Baths
    • 2,060 Sq Ft

    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
  • /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
  • /2

    $48,900

    • Land
    • 0.08 Acre
    • $611,250 per Acre

    1639 Columbia Beach Rd, Shady Side, MD 20764

    Nice, level lot ready for your dream home! Located right by Flag Pond, this property has a sewer hookup available, and the suggested building footprint is 30 ft x 40 ft. Bring your own builder and make it your own.

    Rob Schou EXP Realty, LLC

    1639 Columbia Beach Rd, Shady Side, MD 20764
  • /2

    $42,000

    • Land
    • 1.53 Acres
    • $27,451 per Acre

    6152 Shady Side Rd, Shady Side, MD 20764

    DISCOVER THIS 1.53 ACRE LOT AVAILABLE IN SHADY SIDE , MD WITHIN ANNE ARUNDEL COUNTY. ZONING R1. DRIVE BY TODAY TO DETERMINE FOR YOURSELF HOW IT CAN WORK FOR YOUR NEEDS!

    Jennifer Drennan Taylor Properties

    6152 Shady Side Rd, Shady Side, MD 20764
  • /15

    $997,000

    • Land
    • 1.60 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
  • /11

    $185,000

    • Land
    • 1.00 Acre
    • $185,000 per Acre

    6508 Shady Side Rd, Shady Side, MD 20764

    Build your dream home! few lots like this one. Dry area, very private & wooded lot surrounded by 73 acres in conservation easement. Enjoy peaceful nature. This lot has a right of way agreement along with lot at 6512 W Shady Side Rd See attached documents and maps. Located close to the west river and community Baseball diamond and basketball courts.

    George Heine Schwartz Realty, Inc.

    6508 Shady Side Rd, Shady Side, MD 20764
  • /12

    $198,000

    • Land
    • 1.44 Acres
    • $137,500 per Acre

    6512 Shady Side Rd, Shady Side, MD 20764

    This lot could .be yours, surrounded by nature, in conservation easement, Dry wooded lot! Build your dream home, surrounded by trees and by 73 acres in conservation easement. Next to 6508 lot, they share an easement for driveway. The best lot in the area!! Close to Baltimore, DC, and Annapolis. Located near the West River and community baseball diamond and basketball court.

    George Heine Schwartz Realty, Inc.

    6512 Shady Side Rd, 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
  • /2

    $100,000

    • Land
    • 1.00 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
  • /2

    $25,000

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

    0 Haile Pkwy Unit MDAA2109444, 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 MDAA2109444, Shady Side, MD 20764
  • /2

    $150,000

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

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

    Sam Tanner Keller Williams Flagship

    0 Shady Side Rd Unit MDAA2113166, Shady Side, MD 20764
  • /2

    $150,000

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

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

    Sam Tanner Keller Williams Flagship

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

Showing Results 1 - 40, Page 1 of 2

Frequently Asked Questions

What are the most popular zip codes in Shady Side, MD?
The most popular zip codes in Shady Side, MD include 20774, 20772, 21403, 21401 and 20613.
What are the most popular neighborhoods near Shady Side, MD?
The most popular neighborhoods near Shady Side, MD are Harwood, Selby-on-the-Bay, Davidsonville, Victor Haven and Tyler Heights-Primrose Acres.
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