Shady Side Homes for Sale

Shady Side Homes for Sale

Welcome to Shady Side, Maryland, a hidden gem nestled in the heart of Anne Arundel County. This picturesque waterfront community offers a unique blend of serene living and vibrant outdoor activities, making it an ideal place for families, retirees, and anyone seeking a peaceful retreat close to nature. With its charming streets lined with historic homes and modern residences, Shady Side captures the essence of small-town charm while providing easy access to the bustling city life of nearby Annapolis and Washington, D.C.

Shady Side is renowned for its stunning views of the Chesapeake Bay, making it a haven for boating enthusiasts and nature lovers alike. Residents enjoy a variety of recreational opportunities, from kayaking and fishing to hiking along scenic trails. The area is also home to several parks, providing ample space for picnics, sports, and family gatherings.

When it comes to real estate, Shady Side offers a diverse range of homes for sale, catering to various tastes and budgets. Whether you’re looking for a cozy cottage with waterfront access or a spacious family home, you’ll find plenty of options to suit your needs. Many properties boast beautiful gardens, modern amenities, and breathtaking views, ensuring that you can enjoy the tranquility of this charming community.

Discover the allure of Shady Side, where you can enjoy a relaxed lifestyle amidst nature while being close to urban conveniences. Explore our listings today and find your dream home in this enchanting Maryland locale!

Newest Shady Side Homes for Sale

8 Beds ⋅ 7 Baths

A Rare Chesapeake Bay Waterfront Offering at this price. Encompassing more than 9,000 square feet of refined living space, this bespoke 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 6+ 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

1 Beds ⋅ 1 Baths

This is an estate sale. Cute 1 BR 1BA cottage located a few hundred yard from the bay. Needs some TLC but livable. Roof is less than 7 years old. Solar panels are owned and not leased. Includes boat slip number 7. Would make a great getaway home or investment property. Sold strictly "as is". Seller will make no repairs.

1737 Cedar Ave, Shady Side

Listing courtesy of RE/MAX Realty Plus. Contact:

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

4 Beds ⋅ 3 Baths

This Stylish New home is move in ready and just in time to enjoy the summer breezes at the community Beach areas and play grounds! It is ready for your personal touch to make it your own! Main level features include Luxury Vinyl Plank flooring, 9' ceilings, Luxury kitchen with granite countertops, stainless steel appliances accented with sleek white cabinets with soft close drawers and a center island with breakfast bar area! The open flow from the kitchen to dining area and then into the living area with corner gas fireplace in view, is a dream! The upper level features large bedrooms and the owners suite features a walk-in closet with built-ins and luxurious bath with double vanity and glass-enclosed tile shower! The additional bedrooms are designed to allow the Sunlight in with the central bath having a dual vanity as well. Come enjoy all the amenities this neighborhood has to offer, like the community Beach, playground areas, dock and boat ramp for accessing South Creek and the Rivers and Bay! You will know you are home when you arrive, come take a look!

1316 Juniper St, Shady Side

Listing courtesy of Long & Foster Real Estate, Inc.. Contact:

3 Beds ⋅ 3 Baths

1211 Linton Ln, Shady Side

Listing courtesy of Keller Williams Capital Properties. Contact:

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:

3 Beds ⋅ 3 Baths

Opportunity awaits at this charming farmhouse nestled in the waterfront community of Shady Side. Situated on a spacious lot, this home offers a peaceful setting with convenient access to local marinas, parks, dining, and commuter routes. The interior presents a functional layout with generous living spaces, abundant natural light, and endless potential for customization. Enjoy the privacy of the surrounding landscape while taking advantage of the area's relaxed coastal lifestyle. Whether you're looking for a primary residence, a weekend retreat, or an investment opportunity, this property provides a wonderful chance to create your vision in a desirable Anne Arundel County location. Don't miss the opportunity to explore the possibilities this home has to offer.

6372 Shady Side Rd W, Shady Side

Listing courtesy of Maryland Realty Connection. Contact: admin@mdreoconnection.com

3 Beds ⋅ 3 Baths

**OPEN HOUSE SAT 7/25 11am-1pm**New roof & gutters installed last week! 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. 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. 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

2 Beds ⋅ 1 Baths

REDUCED $45,000.00 ALL CASH OFFERS-FIRE DAMANGED INTERIOR- TOTAL REHAB-2 BR 1 Bath quiet secluded street. New Homes being built on same street. Owner reserves right to accept or reject any offer. Owner doing 1031 tax free exchange. Settlement 7-30 days. Haile Parkway/tax record Heile

1432 Heile/Haile Pkwy, Shady Side

Listing courtesy of Flag Real Estate Inc.. Contact:

4 Beds ⋅ 3 Baths

Spacious 2,807 sq. ft. home offering exceptional potential for investors, multi-generational living, or rental income opportunities. The main residence features two bedrooms, one full bath, a kitchen, utility room, and a spacious family room with sliding doors leading to the rear deck. The attached in-law suite has its own private entrance and separate electric meter. Currently tenant-occupied by a long-term tenant who would love to remain, it includes a living room, bedroom, kitchenette, and full bath. The upper level of the home is accessible from both the interior of the main house and a separate exterior entrance. This space offers a living room, kitchenette, and two additional bedrooms, providing even more flexibility for extended family or potential rental use. Situated on a generous ½-acre lot, this property offers endless possibilities for the right buyer. The home requires updating and is being sold "As Is". Conventional financing or cash buyers only.

6201 Shady Side Rd, Shady Side

Listing courtesy of Schwartz Realty, Inc.. Contact:

2 Beds ⋅ 2 Baths

Non-riparian waterfront home offering sweeping, unobstructed views of the Chesapeake Bay. Wake each morning to breathtaking sunrises over the water, best enjoyed from your expansive deck with a cup of coffee in hand—an experience that never gets old. Inside, the home is filled with natural light and features an open-concept layout designed to maximize those stunning bay views. The main level boasts hardwood floors throughout, along with two comfortable bedrooms and a full bath. Upstairs, a versatile loft space with a half bath is ideal for a home office, guest accommodations, or a quiet retreat. Located just steps from the community pier, boat ramp, and additional amenities, this property offers the perfect blend of relaxation and coastal living. Flood insurance is not required.

5211 Al Jones Dr, Shady Side

Listing courtesy of Schwartz Realty, Inc.. Contact:

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