Shady Side Homes with Pool

Shady Side Homes with Pool

Welcome to Shady Side, Maryland—a hidden gem nestled along the picturesque shores of the Chesapeake Bay in Anne Arundel County. This charming waterfront community offers a unique blend of serene living and vibrant coastal lifestyle, making it an ideal place for families, retirees, and anyone seeking a peaceful retreat from the hustle and bustle of city life.

Shady Side is renowned for its stunning natural beauty, with lush landscapes, scenic views, and easy access to the bay. The area is perfect for outdoor enthusiasts, offering a variety of recreational activities such as boating, fishing, and hiking. The local parks and waterfront areas provide ample opportunities for picnics, birdwatching, and simply soaking in the breathtaking sunsets over the water.

One of the standout features of Shady Side is its collection of homes with pools, providing residents with a private oasis to unwind and enjoy the warm Maryland summers. Imagine hosting barbecues by your sparkling pool, relaxing with a good book under the sun, or enjoying evening swims under the stars—all from the comfort of your own backyard. These homes not only offer a luxurious lifestyle but also create a perfect environment for family gatherings and entertaining friends.

With a close-knit community feel, Shady Side boasts a variety of local shops, restaurants, and cultural attractions, ensuring that residents have everything they need within reach. Whether you’re looking for a cozy cottage or a spacious family home, Shady Side offers a diverse range of properties that cater to every taste and lifestyle. Come discover the charm of Shady Side, where your dream home with a pool awaits!

Newest Shady Side Homes with Pool

$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
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