Shady Side MD Real Estate & Homes for Sale

Welcome to an extraordinary waterfront estate offering the perfect balance of luxury, function, and efficiency on Marylands treasured Western Shore. This 9-bedroom, 6.5-bath residence spans 8,400+ square feet and is built to withstand the elements while embracing the serene lifestyle of the Chesapeake Bay. Set on over 2/3 of an acre with 260 feet of water frontage, this solid brick & block home was constructed with reinforced steel walls, high R-value insulation, a poured concrete foundation, and a roof system designed to withstand high winds - all topped with 40-year architectural shingles (inspected Nov. 2024). This is a true fortress disguised as a coastal retreat. Inside, youll find three full-size primary suites with private baths, a massive 3,200+ sqft walkout basement for entertaining or storage, and energy-efficient systems throughout: geothermal heating and AC, multiple radiant and baseboard heating zones, and a combination of solar, propane, oil, and electric systems-keeping average monthly electric costs to just $165. The home also features six 80-gallon water heaters and 3 backup AC systems for ultimate comfort and efficiency. Need room for guests or passive income potential? The spacious guest wing with a separate entrance, two bedrooms, full kitchen, private bath, and a large water-view balcony is perfect for visiting friends, multi-generational living, or Airbnb. The property has two full-size laundry rooms. Step outside to your 2024-renovated 250 pier with 8 deep water, heavy electric service, two boat lifts, two jet ski lifts, and room to add more. The bulkhead is currently being repaired, ensuring long-term value and waterfront stability. Shady Side is a charming and peaceful bayfront community just a short ride to Annapolis, with convenient access to Washington, DC, and Baltimore. Locals enjoy crabbing, fishing, waterfront parks, scenic trails, and the neighborly vibe of this Southern Anne Arundel County gem. This is a rare chance to own a high-performance home with panoramic views, protected shoreline, and multi-generational living opportunities-all in a sought-after Chesapeake Bay setting.

Two story Colonial style home on Steamboat Road. The exterior has a front porch, fenced rear yard and large deck. There is an open floorplan on the first level, 3 bedrooms are located upstairs. This property is located close to the Chesapeake Bay with easy commute to AAFB, DC & Annapolis. Sold in AS IS condition, seller will make no repairs.

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.

PRICE REDUCED! Waterfront Stunner! 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 out 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.

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.

Welcome to this incredible home to-be-built on 1.6 waterfront acres just south of Annapolis. This waterfront lot offers breathtaking West River Views, a deep-water pier, two docks and two boat lifts that convey. Located in shady Side, this property offers the best of both worlds; quiet, small-town charm with easy access to Annapolis and DC. Proposed home is by Whitehall Building, a premier waterfront builder in the Annapolis area. While the design is already thoughtfully planned, you have the unique opportunity to personalize selections and make modifications, ensuring your home fits your vision. Surrounded by estate homes, the drive-in is picturesque, setting the tone for this exceptional property. If you're looking for stunning waterfront and privacy without the hustle of city life, this is it. Ready to build your dream home?

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!

Charming Chesapeake Bay cottage with breathtaking water views from nearly every room! Start your mornings with a stunning sunrise from the all-season front porch. This well-maintained home features beautiful hardwood floors, new windows (2013), fresh paint (2015), and a fully encapsulated crawl space (2022). A detached garage provides extra storage. Just steps from the community beach, marina, pier, boat ramp, playground, and more. This cherished family home, rarely available in such pristine condition with these incredible views, is a true gem. Dont miss this opportunity!. Not in a flood zone. Most furniture can convey if needed. 100% financing available through USDA loan.

Welcome to 1508 Cedarhurst Road in the water-privileged community of Cedarhurst on the Bay. The home features 3 bedrooms, 1 bathroom, and a spacious, fenced-in backyard. Super waterfront community featuring a pier, community house, and nearly 4 acres of waterfront property. Cedarhurst on the Bay is not a homeowners' association (HOA) and does not have monthly fees. It is a tax benefit district. The county collects taxes for Cedarhursts Special Community Benefit District (SCBD) and Shoreline Erosion Control District (SECD). Flood Insurance is NOT required for this property. Home is being SOLD AS-IS. Inspections are for informational purposes only.

An adorable cottage with almost 200' of waterfront facing Hopkins Cove with views of the Chesapeake Bay Bridge. This could be your weekend getaway cottage, or 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.

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..

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.