Shady Side Homes with Coastal Style

Shady Side Homes with Coastal Style

Welcome to Shady Side, Maryland – a hidden gem nestled along the picturesque shores of the Chesapeake Bay in Anne Arundel County. With its charming coastal vibe, Shady Side offers a unique blend of serene waterfront living and a tight-knit community atmosphere, making it an ideal place to call home.

The town is characterized by its stunning waterfront properties, many of which boast classic coastal architecture that harmonizes beautifully with the natural surroundings. Imagine waking up to the gentle sound of waves lapping against the shore and enjoying your morning coffee on a sun-drenched deck overlooking the bay. Homes in Shady Side often feature expansive windows, open floor plans, and inviting outdoor spaces, perfect for entertaining family and friends or simply soaking in the breathtaking views.

Shady Side is not just about its stunning homes; it’s also a lifestyle. Residents enjoy an array of outdoor activities, from kayaking and fishing to exploring the nearby parks and trails. The community is rich in history and culture, with local events that bring neighbors together, fostering a sense of belonging that is hard to find elsewhere.

With its coastal charm and vibrant community spirit, Shady Side offers a unique opportunity for those seeking a tranquil retreat without sacrificing convenience. Just a short drive from Annapolis and Washington, D.C., you can enjoy the best of both worlds – a peaceful coastal lifestyle paired with easy access to urban amenities. Discover your dream home in Shady Side and embrace the coastal living experience today!

Newest Shady Side Homes with Coastal Style

8 Beds ⋅ 7 Baths

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 on nearly five private acres 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, 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

4 Beds ⋅ 2 Baths

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

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

4 Beds ⋅ 3 Baths

Enjoy water views of the community harbor with 60 boat slips and direct access to the Chesapeake Bay—a dream setting for boating and coastal living. This beautifully crafted home features classic board-and-batten siding and a welcoming front porch that creates timeless curb appeal. Inside, the open-concept layout seamlessly connects the dining area and family room, making it perfect for everyday living and entertaining. The spacious kitchen is the heart of the home, showcasing an oversized quartz island, stainless steel appliances, and abundant cabinetry for both casual meals and gatherings. A main-level home office or flexible choice room offers the ideal space for working from home or relaxing. Upstairs, the owner’s suite features a large picture window, expansive walk-in closet, and a spa-inspired bath with a luxury shower. Just a short walk to the community center and playground, residents also enjoy Cedarhurst’s rare four acres of community-owned waterfront property with panoramic bay views, open lawns, wetlands, picnic areas, playgrounds, ball fields, and opportunities to watch sunrises, sailboats, waterfowl, and local watermen working the bay.

1237 Spruce Ave, Shady Side

Listing courtesy of RE/MAX United Real Estate. Contact:

4 Beds ⋅ 4 Baths

There aren't many opportunities left to build brand new in Anne Arundel County at this price point, and 1430 Haile Parkway is one of them. Haile Parkway is quiet, wooded, and tucked into the laid-back charm of Shady Side, close enough to everything you need, far enough away to actually exhale. New construction at this level of quality and finish from one of the area's most respected builders is a rare find, and the price makes it even more compelling. Whitehall backs every home with a fixed-price contract, weekly progress reports, and a 5-year structural warranty, the kind of transparency that makes the building process smooth and confidence-inspiring. Construction-to-permanent or cash financing required; 100% VA financing options available for those who qualify. Whitehall Building & Company's Chessie plan is a thoughtfully designed three-level home offering over 3,000 square feet that lives larger than it looks. The main level centers around a generous family room with fireplace, a well-proportioned kitchen with pantry, dining area, and a dedicated office, the kind of layout that feels spacious and connected. A covered porch off the main level brings the peaceful, wooded setting into the daily experience. Upstairs, the primary suite is a true retreat, complete with a private bath and walk-in closet. Two additional bedrooms, a shared full bath, and upper level laundry round out the second floor. The lower level includes a bedroom and full bath, ideal for guests or added flexibility, along with a two-car garage and entry foyer.

1430 Haile Pkwy, Shady Side

Listing courtesy of Hubble Bisbee Christie's International Real Estate. Contact:

4 Beds ⋅ 3 Baths

AUGUST Delivier!!!! Enjoy water views of the community harbor with 60 boat slips and direct access to the Chesapeake Bay—a dream setting for boating and coastal living. This beautifully crafted home features classic board-and-batten siding and a welcoming front porch that creates timeless curb appeal. Inside, the open-concept layout seamlessly connects the dining area and family room, making it perfect for everyday living and entertaining. The spacious kitchen is the heart of the home, showcasing an oversized quartz island, stainless steel appliances, and abundant cabinetry for both casual meals and gatherings. A main-level home office or flexible choice room offers the ideal space for working from home or relaxing. Upstairs, the owner’s suite features a large picture window, expansive walk-in closet, and a spa-inspired bath with a luxury shower. Just a short walk to the community center and playground, residents also enjoy Cedarhurst’s rare four acres of community-owned waterfront property with panoramic bay views, open lawns, wetlands, picnic areas, playgrounds, ball fields, and opportunities to watch sunrises, sailboats, waterfowl, and local watermen working the bay.

1235 Spruce Ave, Shady Side

Listing courtesy of RE/MAX United Real Estate. Contact:

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