Shady Side, MD Houses for Sale

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

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

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.

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.

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

Experience a serene lifestyle by the Chesapeake Bay—trading the fast-paced chaos for peaceful coastal living. 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,

Bonnie O'Donnell RE/MAX One

Merchant Unmatched water views. Over 8,000 sq ft of curated living. A property that doesn’t just stand out—it stands alone.Tucked away in the quiet, rural charm of Shady Side, this architecturally bold residence offers year-round views of the West River and a lifestyle that feels worlds away—yet keeps you close to everything that matters. Step inside and you’re immediately immersed in

Phil Gerdes Real Broker, LLC - Annapolis

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.

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.

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.

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

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

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

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

Welcome to this delightful coastal cottage nestled in the heart of the Columbia Beach community! Spacious wide beach, tot lot, tennis courts and basketball too. This beautifully updated home perfectly balances modern comfort with timeless charm. Offering two spacious bedrooms and a full bath, the layout is thoughtfully designed for easy living and effortless style.Step inside to find

Amy Juras Long & Foster Real Estate, Inc.

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

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

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

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.

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

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

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

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

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

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.

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 living, dining, kitchen, 2 bedrooms, a

Celeste Blessin Coldwell Banker Realty

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

Unique Waterfront Dream Home Opportunity at Columbia Beach – Build Your Dream Home on the Chesapeake Bay. Don't miss this rare chance to build or own waterfront Dream Home 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.,

Rodrigo Cruz Long & Foster Real Estate, Inc.

Professional photos coming soon! 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

Nicki Palermo RE/MAX One

Welcome to 5122 Marx Drive, nestled in the highly sought-after, water-privileged community of Cedarlea. Situated on nearly half an acre, this home features bright, open spaces with large windows and vaulted ceilings in the living room, primary bedroom, and sunroom. Arrive home to the spacious two-car garage with plenty of room for vehicles, tools, or a jet ski trailer! The main level offers a

Tom Atwood Keller Williams Legacy

Coming Soon. Professionally photos will be loaded in July. Beautiful fenced rear yard with extensive hardscape.

Ray Mudd Schwartz Realty, Inc.

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

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 combine living and dining rooms to the a nice sized kitchen with appliances and main level bedroom. There is a full bath in each level and three more bedrooms in the upper level. The sunroom with wide windows and lots of

Gina Gargeu Century 21 Downtown

Cindy Martin Samson Properties