Shady Side MD Waterfront Real Estate, Homes, Condos for Sale

Waterfront living at its finest in Avalon Shores on South Creek! This 3-bedroom, 4.5-bath home features a versatile study/bonus room, beautiful wood floors, updated kitchen and baths, and modern fixtures throughout. Enjoy water views from the expansive screened-in back porch or multiple decks spanning the second and third levels. The waterfront setup is ideal for boating enthusiasts with a remote-controlled boat lift and three jet ski lifts. A 2-car garage provides convenient parking and storage. New roof installed in 2023, while bulkhead was redone in 2016. Enjoy relaxing, entertaining, and life on the water!

5060 Lerch Dr, Shady Side

Listing courtesy of Redfin Corp. Contact: 3016586186

$998,000

4 Beds ⋅ 3 Baths

Waterfront living at its finest! This custom-built Chesapeake Bay home offers breathtaking panoramic views stretching all the way to the Bay Bridge. Meticulously maintained and truly move-in ready, this exceptional property combines luxury, comfort, and the best of coastal living. The main level features beautiful hardwood floors, a spacious gourmet kitchen with granite countertops, stainless steel appliances, and an open layout overlooking the inviting family room with a gas fireplace and spectacular Bay views. A main-level bedroom and full bath provide the perfect accommodations for guests. Upstairs, you'll find three additional bedrooms and two full baths, including a stunning waterfront primary suite. Wake up each morning to endless water views through walls of glass, then step onto your private covered terrace to enjoy your morning coffee while watching the sunrise over the Chesapeake Bay. Outside, your private pier offers the perfect place to fish, crab, or take the boat for a day on the water. Cruise to the many nearby waterfront restaurants and marinas, or simply relax and enjoy the peaceful waterfront setting. Conveniently located with an easy commute to Annapolis, Washington, D.C., and Baltimore, this remarkable home is nestled in the charming waterfront community of Felicity Cove. If you've been dreaming of exceptional Chesapeake Bay waterfront living, this is a home you won't want to miss.

4721 Oak Rd, Shady Side

Listing courtesy of Schwartz Realty, Inc.. Contact:

$1,600,000

8 Beds ⋅ 7 Baths

BY APPOINTMENT ONLY Saturday September 12th 12-3. Rich in history, timeless in character, and unmatched in location, this extraordinary waterfront estate traces its origins to the early 1900s as the historic Girton House Hotel. Perfectly positioned at the tip of Curtis Point, where the West River meets the Chesapeake Bay, the property later became the beloved Danes on the Bay restaurant, a cherished local landmark. Today, this remarkable estate offers an exceptional blend of historic significance, architectural character, and one of the Chesapeake Bay’s most spectacular waterfront settings. Encompassing more than 9,000 square feet of living space, this waterfront estate is gracefully sited on a premier point of land just under one acre, with over 250 feet of protected shoreline and a private deep-water pier with approximately six plus feet of mean low water depth, ideally suited for both elegant sailing vessels and substantial power yachts. Located just 20 miles from historic Annapolis and approximately 45 miles from Washington, D.C., the residence offers an extraordinary balance of secluded waterfront luxury and effortless access to major metropolitan destinations. Commanding sweeping vistas of the Chesapeake Bay and West River, the estate features multiple boat lifts, eight bedrooms, and an array of expansive, thoughtfully designed entertaining spaces. A truly rare offering, it stands among the most compelling values for a luxury waterfront estate in the region.

4701 Girton Ave, Shady Side

Listing courtesy of TTR Sotheby's International Realty. Contact: (410) 280-5600

$699,900

4 Beds ⋅ 2 Baths

Buy the waterfront. Make the house your own. Rare Waterfront Opportunity on South Creek! Bring your vision and make this special waterfront property your own! Situated on a rare 0.74-acre lot, this home has been lovingly maintained by the same family for many years and is ready for its next chapter. Enjoy the waterfront lifestyle with your private pier, offering easy access for boating, fishing, kayaking, or simply relaxing by the water. The spacious home features a main-level bedroom (currently used as sitting room), generous living areas, 2 full baths, and an attached two-car garage with two driveways - providing a flexible floor plan with room to grow. Major improvements include a new roof (2023), while the home's spacious interior provides the perfect canvas for your personal updates and design ideas. Properties like this are becoming increasingly difficult to find. Whether you're looking for a year-round residence, weekend retreat, or investment in waterfront living, this is an exceptional opportunity to create something truly special. Flood Zone information to be independently verified by buyers. Sold strictly As-Is.

5078 Lerch Dr, Shady Side

Listing courtesy of CENTURY 21 New Millennium. Contact: 4102669005

$995,000

3 Beds ⋅ 2 Baths

Exceptional value for this exquisite, recently renovated coastal waterfront retreat, offering the perfect blend of luxury, comfort, and breathtaking water views throughout. The home features three generously sized bedrooms, including a convenient main-level primary bedroom, and two elegantly appointed bathrooms. The bright, open floor plan is enhanced by vaulted ceilings, recessed lighting, solar-powered skylights with built-in remote-controlled shades, and beautifully refinished oak hardwood flooring throughout the main level. Recent improvements include a new architectural-shingle roof, new upper-level carpeting in both bedrooms, new water treatment system, and professionally and tastefully painted inside and out. At the heart of the home, the gourmet kitchen features solid wood white cabinetry, updated appliances, new quartz countertops, a huge center island with cooktop, prep sink, ample seating, and a spacious eat-in area—ideal for the culinary enthusiast as well as for everyday living and entertaining. The inviting great room, complete with a cozy gas fireplace, is the perfect place to relax and unwind and take in the wonderful views. Step outside to a beautifully landscaped, level 0.24-acre lot and enjoy your own private L-shaped pier with resurfaced decking, multiple slips, and a boat lift. A new bulkhead adds even more value to this exceptional property situated on South Creek, just off the West River and Chesapeake Bay—perfect for boating, crabbing, fishing, and enjoying life on the water. Take in the expansive views from the multi-level decks and adjoining screened-in area, creating an outstanding setting for relaxing and entertaining. An oversized one-car garage provides additional storage, while the newly paved driveway offers off-street parking for six or more vehicles. Community amenities are complete with a swimming beach, dock, picnic area, and playground. Come experience the sought-after lifestyle of South County waterfront living—your dream coastal oasis awaits!

4958 Lerch Dr, Shady Side

Listing courtesy of Beam Realty Group, Inc.. Contact: 4438656969

$699,000

3 Beds ⋅ 3 Baths

***OPEN HOUSE SAT 9/12 11am-1pm***Welcome to the Honey Hole of the South Creek! New roof & gutters freshly installed! Welcome to your own private waterfront retreat nestled at the peaceful head of South Creek, where breathtaking views, abundant wildlife, and the ultimate Chesapeake Bay lifestyle come together. Perfectly positioned on a beautifully level lot, this exceptional property offers a private pier ideal for launching a kayak, canoe, paddleboard, or boat, while the nearby community marina provides access to deep-water slips for larger vessels. Residents also enjoy access to the community beach, making every day feel like a vacation. An added bonus is the inclusion of the adjacent Lots 17 & 18 (4907 Thomas Drive), providing additional privacy, flexibility, and future possibilities. Step inside to discover a bright, open floor plan designed to maximize both the water views and natural light. The spacious kitchen features a center island, ample cabinetry, and a sunny breakfast area highlighted by a large picture window overlooking the creek—an unforgettable place to enjoy your morning coffee. The adjoining living room offers the warmth and charm of a wood-burning stove along with sliding glass doors leading to the expansive wraparound screened porch, creating the perfect space for indoor-outdoor entertaining or simply relaxing while watching osprey, herons, and other local wildlife. Large pantry area for additional storage and separate dining room for additional room to spread out. Upstairs, all three bedrooms are thoughtfully situated, including a spacious primary suite that serves as a true waterfront sanctuary. Wake up each morning to panoramic water views from your private balcony, then unwind in the en-suite bath featuring a walk-in closet and plenty of room to recharge after a day on the water. The additional bedrooms are generously sized, with one also enjoying beautiful water views, and are served by a second full bathroom on the upper level. This home has been thoughtfully updated for peace of mind and long-term enjoyment. It may say it was built in 1941, but this home went through an extensive remodel in 1991 taking the original beach bungalow to the oversized colonial it is today. Recent improvements include a brand-new roof (2026), renovated Tigerwood deck, and a professionally encapsulated crawlspace complete with a dehumidification system. If you’ve been dreaming of a waterfront lifestyle that combines privacy, natural beauty, and everyday comfort, this is a rare opportunity to own a special piece of Southern Anne Arundel County. Whether you’re boating, crabbing, kayaking, entertaining on the screened porch, or simply enjoying the peaceful creek views, you’ll quickly understand why this location is so special.

1241 Johnson Dr, Shady Side

Listing courtesy of RE/MAX One. Contact: 4105356291

$149,900

WATERFRONT OPPORTUNITY!! Discover the perfect setting to build your dream home or weekend retreat on this waterfront lot offering breathtaking views of the Chesapeake Bay. Nestled in the quiet, secluded community of Columbia Beach, this approximately 4,450-square-foot homesite is already serviced by public sewer, making it an exceptional opportunity to bring your vision to life. Wake up to stunning sunrises, enjoy the peaceful waterfront surroundings, and embrace the laid-back Chesapeake lifestyle with boating, fishing, kayaking, and endless opportunities to relax by the water. Whether you're looking to create a full-time residence or a private coastal escape, this rare waterfront property offers the chance to own a slice of the Bay in a tranquil setting. Don't miss this unique opportunity!

5209 Al Jones Dr, Shady Side

Listing courtesy of CENTURY 21 New Millennium. Contact: 4439689595

$775,000

3 Beds ⋅ 2 Baths

Waterfront living with a private dock—all for only $775,000! Nestled in the charming Avalon Shores community, this beautifully updated coastal home perfectly blends classic elegance with modern comfort. The open-concept layout features two distinct living areas, ideal for both entertaining and daily relaxation. At the heart of the home is a premium kitchen equipped with granite countertops, stainless steel appliances, a center island with seating, and a sleek range hood. Large bay windows flood the main level with natural light. Enjoy beautifully finished bathrooms, a bedroom on the main living level, and two spacious bedrooms upstairs. Want more room? There’s extra space for an office, playroom, or a bedroom in the loft. Step outside to discover 63 feet of premier waterfront along South Creek. The spacious fully-fenced backyard and private dock with electric & water offer the perfect launchpad for kayaking, paddleboarding, or simply soaking in the tranquil scenery. The primary bedroom has a private balcony to enjoy the creek views. Enjoy peace of mind with new kitchen appliances (dishwasher, fridge - 2025; range hood - 2026), new roof (2025), new HVAC (2026), and sealing work and crawl space encapsulation (2020). Complete with an attached two-car garage with a 12kW Level 2 EV charger, offering secure inside access, and the convenience of a personal air-conditioned gym (or open the doors and enjoy the view and sounds of nature!). This turnkey property is a rare opportunity to live the ultimate waterfront lifestyle. Schedule your tour today!

4950 Bonniewood Dr, Shady Side

Listing courtesy of RE/MAX Leading Edge. Contact:

$3,500,000

5 Beds ⋅ 6 Baths

Silver Water is a rare west-facing waterfront home designed in direct response to the Chesapeake—offering broad water views, remarkable sunsets, and a level of architectural clarity seldom found in the area. Set behind a private gate on a beautifully landscaped one-acre lot along the West River, the property combines seclusion with convenient access to Annapolis and Washington, DC. Spanning over 4,600 square feet, the home blends classic Chesapeake architecture with modern scale, light, and livability. High ceilings, oversized doors, and expansive windows draw the water into nearly every room, creating a constant connection to the horizon. The layout balances open, light-filled gathering spaces with a thoughtful separation of private areas, making it equally suited for everyday living and hosting guests. The main-level primary suite is positioned to capture water views, with a fireplace, spa-like bath, and custom walk-in closet. At the center of the home, the kitchen is designed for both daily use and entertaining, anchored by professional-grade appliances and clean, functional design. Outdoor living is fully realized. A waterside saltwater pool, bluestone terraces, teak decking, and a fully equipped pool house create a seamless extension of the home—designed for both relaxed days and larger gatherings. The lawn stretches to a protected shoreline, reinforcing the home’s connection to the water. A private 70-foot pier with lift provides immediate access to the Chesapeake, ideal for day boating and spontaneous time on the water, with nearby marinas accommodating larger vessels. Additional features include mature landscaping, a smart irrigation system, multiple outdoor living areas, a detached three-car garage, and a separate storage structure. Silver Water offers a rare combination of design, setting, and livability—an intentional waterfront home where architecture and landscape come fully into alignment.

4750 Frederick Ave, Shady Side

Listing courtesy of Berkshire Hathaway HomeServices PenFed Realty. Contact: 4433727171

$699,000

4 BEDS/1FULL BATH AND1/2 BATH WITH SHOWER. 2144SQ FT. Home income opportunity goes with this four bedroom home on .57 acres of (C1B) commercial zoned property. Additional .375 acres and .1243 acres of (MC) heavy commercial 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 8 feet that can accommodate boats in excess of 40 feet. Total income from 6 of the 12 slips in 2025 was $6900!! POTENTIAL for much more PLUS Additional rental income from DRY STORAGE AVAILABLE. Many upgrades and extras. Information sheet in the document section of the listing or may be emailed to interested parties. .

1462 Snug Harbor Rd, Shady Side

Listing courtesy of Schwartz Realty, Inc.. Contact:

$699,900

3 Beds ⋅ 2 Baths

Experience Unmatched Privacy and Tranquility from this unique non-riparian waterfront home set on over 3+ scenic acres. Fall in love with sweeping water views and the serene presence of native wildlife—waterfowl, deer, eagles, and more—all just outside your door. Enjoy panoramic vistas of a natural pond, with the stunning Chesapeake Bay visible in the distance. On clear days, the Bay Bridge is even within sight. The home features a relaxing screened porch, a spacious kitchen that flows into a cozy living area with a wood stove—perfect for chilly evenings. The main level includes a bedroom and full bath, plus an additional room ideal for an office or second living space, also with a wood stove. Upstairs, the primary bedroom offers breathtaking water views, accompanied by another bedroom and a full bath. A barn/stable on the property makes it ideal for horses or a home-based business with office space. This is truly a one-of-a-kind property—peaceful, picturesque, and full of potential. Come see it for yourself.

1650 Cedar Ln, Shady Side

Listing courtesy of Schwartz Realty, Inc.. Contact:

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Shady Side Waterfront Real Estate