Shady Side MD Real Estate & Homes for Sale

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 or great room for entertaining, with a brick fireplace, cathedral ceiling, exposed beams, and large windows. You'll love this charming space! The living room also has a brick fireplace, lots of windows, LVP flooring and sliding glass doors that open to the brick enclosed patio overlooking the lovely fenced yard. The renovated primary suite includes stylish sconces, large vanity w/chrome fixtures, quartz countertops, and an on-trend walk-in glass framed shower. The second bath has new lighting, mirror, fixtures, a tub/shower combo, and also hosts the full-size washer and dryer with shelving, The second bedroom boasts a custom Elfa closet system. Step outside to enjoy a fully fenced yard, a patio area framed by brick, a beautifully landscaped garden, and a large shed for extra storage. All this and a newly paved driveway that can hold up to 4 vehicles! Youll love the laid-back lifestyle of Cedarhurst on the Bay --a vibrant community with a clubhouse, dock, playground, & MORE with easy access to waterfront marinas, community parks, and beloved local spots like JesseJays Latin Inspired Kitchen, Petie Greens Bar & Grill, and the Driftwood Diner. Plus, you're just a 20-min drive to Annapolis and under an hour to Washington, D.C., making this the perfect blend of coastal retreat and commuter convenience. Dont miss your chance-this home shows beautifully and wont last long!

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 pit, kayake launch and impeccably landscaped grounds. A private pier with a boat lift provides direct access to the water, making this the perfect setting for boating enthusiasts and those seeking tranquility by the shore. Inside, the home is richly appointed with custom finishes and a spacious open-concept design. The gourmet kitchen offers premium appliances, custom cabinetry, and expansive water views that flow into the main living and dining areas. Every detail has been thoughtfully curated for both function and elegance.The bathrooms have been recently remodeled with luxurious, spa-inspired touches. The primary suite is a sanctuary, complete with a serene spa-like bath, walk-in shower, soaking tub, and private access to an outdoor sauna - your personal retreat just steps from the bedroom. Additional highlights include a new roof, upgraded geothermal HVAC system for efficient, year-round comfort, and a three car garage with ample storage space. Whether youre hosting guests, spending weekends on the water, or simply enjoying peaceful moments at home, this extraordinary property offers the perfect blend of sophistication, comfort, and waterfront charm.

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 ceiling accents. The home also features a large 2 car garage, and a spacious yard which includes ample front back and side yards.

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. Upstairs features four bedrooms, including a primary suite with views of both the Bay and Flag Pond, plus an en-suite bath, three additional bedrooms, and a full hall bath. A two-car garage includes an extra storage room. While the home could use some updating and TLC, it presents a fantastic opportunity to make it your own. Located in a vibrant waterfront community with amenities such as a boat ramp, pier, tennis courts, and more. Come experience the Chesapeake Bay lifestyle.

Ready for Viewing! Welcome to this wonderfully unique and updated home in the small community of Felicity Cove. Felicity Cove is a private, waterfront community of only 34 homes with a large community pier and outdoor areas. With part-time and full-time residences there is not a lot of turnover in the community. This home is 2 story brick and vinyl clad Cape Cod style with a Mid-century Modern vibe. Built in 1976. The home is move in ready! In about 2200 square feet there are 4/5 bedrooms, 3.5 bathrooms, bonus office or 5th bedroom and family room. The family room has vaulted ceiling and hearth for a wood or pellet stove. Living room and office/5th bedroom have fireplaces. Enjoy the bay air and view from the 3-season porch. There is oak flooring throughout both floors. Custom wood trim and slate floor in the open 2-story foyer. 3 full bathrooms were remodeled in 2024-25 with custom tile. The Primary bedroom has plenty of room for a king size bed. Be the first to utilize the new ensuite walk-in shower and dual vanities. The galley style kitchen was remodeled with granite counters. The fridge, range and water heater were replaced this year. In 2014, 2 heat pump systems were installed including ducting (recently serviced). 2016 New insulation and vapor barrier installed in the crawl space. New vinyl siding, house wrap, vinyl eaves, vinyl wrapped exterior beams and a new bay window were installed. New roof was installed with 40 year shingles in the fall of 2023, flat roof portion was replaced in 2014. New gutters system installed spring of 2024. The home sits on almost 1/4 acre with partial privacy hedges and off-street parking for 3 vehicles and/or a boat. Large shed in great condition and conveys.

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 natural lights have a great view of the backyard and leads to the rear deck, which is a perfect spot for outdoor fun. The rear exterior includes a 3-car detached garage with large workshop and a shed. Home is located in a water-oriented community and is conveniently close to the beach, marina and Shady Side Market.

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". Please contact AACO and the Critical Area Division regarding remodeling permit requirements.

Here is your chance to own and enjoy a coastal contemporary â??cottageâ? 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 full bathroom, and laundry . Take advantage of the loft, with its natural light, perfect for a home office or studio. Plus a half bathroom and additional storage. Enjoy seamless indoor - outdoor living, expanded with a new low maintenance deck. Perfect for morning coffee and entertaining on the bay. Replaced: Deck in 2024.. Sump Pump and exterior faucet 2024.., Main level bathroom 2020.. Leaf Filter Gutter Guards , 2019,.. Split 2018.. Bedroom windows, 2016.. Roof, 2014 . Upper half bathroom added in 2009. Situated in the gated water privileged community of Columbia Beach. The community offers residents opportunities for boating, fishing, and other recreation: boat launch, short fishing pier, a long pier, waterfront park, childrens play area, regulation size basketball court, and tennis. The community walking path, along the rocks that line the cove, is marked by oval signs featuring a swan. Vacation Year Round !

Merchant Unmatched water views. Nearly 8,000 sq ft of curated living. A property that doesnt 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 youre immediately immersed in nearly 8,000 square feet of living space-designed with intention, filled with original art, historical artifacts, and featured in multiple publications for its distinctive character. This, all because this home, this masterpiece, boasts design elements created by one of the worlds most renowned artists. From the banquet-sized dining room to the grand living space that opens to the water, every room delivers scale, flow, and timeless style. The chefs kitchen anchors the home with form and function, while five spacious bedrooms and 5.5 baths offer more than enough room to retreat away for moments of relaxation and peace. Outside, an acre of manicured gardens and carefully curated sculptures surrounds the home-offering a peaceful backdrop for everything from morning coffee to sunset wine. And with no HOA, this is freedom at its finest. Just off the beaten path, yet only minutes from the dockside restaurants of Deale, the historic charm of Galesville, and the energy of Annapolis-with a surprisingly easy commute to DC and Baltimore-this home offers a balance few properties can match. Offered with the ability for the new owner to keep much of the furnishing and art pieces (to be negotiated with offers), this home isnt just a place to live-its a place to belong. Live bold. Live different. Welcome home.

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 2018. It has an oversized 1 car garage with workshop for storage for those handyman/handywomen projects. Sale contingent on owner finding a home of their choice and they may need a rent back to make that work. New photos will be coming!

Open Saturday, April 26 11:00 to 1:00. 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 at the end of Hine Drive and walk there! The Yacht Club offers slips, a pool, restaurant and other amenities. This is a unique property with 2 separate 2 story living areas, 2 exterior entrances. The two sides are easily united by just opening the living room to the other side.

Waterfront Stunner for under $750K! This home features main-level living with a large bedroom and full bath. The kitchen opens to the living area with tons of natural light. Upstairs, two additional bedrooms with private baths ensure everyone has their own space & privacy. Outside is a small finished entertainment area or walk to your private dock. Crab in the summer or take a kayak, SUP, or canoe for a sunset paddle. New Roof in 2024. Make sure to see this house before it's gone! Flood Insurance Required- Flood Zone AE. $135 annual Civil Owners Association is included with the taxes. It covers road maintenance, the two playground parks, and the boat ramp maintenance.

MAJOR PRICE ADJUSTMENT on this incredible property! You could not build this home in this location for this amount! Located on a private 2.5-acre lot with over 300 ft of West River waterfront, 1346 E West Shady Side Road offers immediate access to the Chesapeake Bay via a private pier with lifts for jet skis and a boat. This grand home combines luxury, craftsmanship, and stunning water views. The double-story foyer, with a Schonbeck chandelier and floating staircases, opens to a fabulous great room and waterside porch. The floor plan includes two main-level primary suites with gas fireplaces, an informal dining area, great room with two-story ceiling, and a chefs kitchen with Sub-Zero and Wolf appliances, all overlooking the water. Hardwood floors and unique features, like a water view window through the stone fireplace, make the home even more special. The second floor has four bedrooms with ensuite bathrooms, a bonus room, and an elevator servicing all three levels. The third floor has two more bedrooms, a bathroom, and a casual seating area-ideal for guests or as an au pair suite. The oversized four-car garage includes space for a boat or RV. Outside, a large terrace leads to the private beach and pier. The property is equipped with geothermal heating and cooling, multiple hot water heaters, and two backup generators. Just an hour from Washington DC and 40 minutes from Annapolis, this is an unparalleled waterfront retreat.

OPEN Bay-front at this newly listed, 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- throughout!- Inviting gourmet kitchen with gleaming granite countertops, large island with seating to host grandly, shiny stainless appliances & open to bright dining & living spaces w/ cozy gas fireplace & direct Bay views! Living spaces are extended by BOTH main-level AND upper-level full-length spaces- covered porch for late day cocktails and crabs after a fun day of boating, to coffee on upper deck waking up to the lap of the waves. Anderson windows, dual-zone HVAC, 'Generac' generator conveys!, Close to work & play with unbeatable open views, unmatched community amenities include boat ramp, tennis courts, playground, clubhouse, gated entry & fun events! Just minutes outside of Annapolis- and less than an hour to DC, this gorgeous retreat is sure to please! Hurry to claim today!

Welcome to 1419 Shady Rest Rd, it located on a quiet street not far from the water in one of Marylands Chesapeake Bay boating communities. This property has a drive way with plenty of space for parking. Being sold AS IS. Priced to sell so schedule your showing today! Please contact Torrence Hall for showings..

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, MD is 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 road (West River Road ) follow signs to property. use GPS (once on West River Road make a left turn pass the first house on the left and follow gravel road to the end.)

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 excess of 40 feet. Total income from 7 of the 12 slips in 2021 was $11,300. POTENTIAL $20,000 PLUS RENTAL INCOME IN ADDITION TO DRY STORAGE AVAILABLE. Many upgrades and extras. Information sheet in the document section of the listing or may be emailed to interested parties. Cold box has been removed.