Winchester On The Severn Homes for Sale

Winchester On The Severn Homes for Sale

Welcome to Winchester On The Severn, a charming waterfront subdivision nestled in the heart of Annapolis, Maryland. This idyllic community offers a unique blend of serene living and vibrant local culture, making it one of the most sought-after neighborhoods in Anne Arundel County. With its picturesque views of the Severn River and lush, tree-lined streets, Winchester On The Severn is a haven for those seeking a tranquil lifestyle without sacrificing proximity to the bustling charm of downtown Annapolis.

The homes for sale in Winchester On The Severn are as diverse as the residents themselves, featuring an array of architectural styles that cater to various tastes and preferences. From elegant waterfront estates to cozy family homes, each property is thoughtfully designed to maximize comfort and style. Many homes boast expansive decks and patios, perfect for entertaining and enjoying the stunning sunsets over the river. Inside, you’ll find spacious layouts, modern amenities, and high-quality finishes that make everyday living a pleasure.

Living in Winchester On The Severn means embracing an active lifestyle. Residents have access to private community amenities, including walking trails, parks, and boat ramps, allowing for easy exploration of the beautiful waterways. Plus, with Annapolis just a short drive away, you’ll have access to a wealth of dining, shopping, and cultural experiences.

If you’re looking for a home that combines natural beauty, community spirit, and modern convenience, Winchester On The Severn may just be the perfect place for you. Explore our listings today and discover your dream home in this enchanting neighborhood!

Newest Winchester On The Severn Homes for Sale

$2,500,000
6 Beds 7 Baths
READY TO BUILD NOW!! Introducing an exceptional opportunity to build your dream home with a local custom home builder on a rare 2.19-acre homesite in the highly sought-after water-privileged community of Winchester on the Severn—a neighborhood where everyday living feels like a vacation. This thoughtfully designed custom home will offer over 6,700 square feet of finished living space, featuring 6 bedrooms, 6 full baths, and 1 half bath, along with a 3-car garage, blending timeless craftsmanship with modern luxury and functionality. The main level is designed with both comfort and entertainment in mind, showcasing an open-concept floor plan anchored by a gourmet kitchen featuring high-end appliances, an expansive workspace, and seamless flow into gathering spaces. A beautifully appointed butler’s pantry includes a built-in ice maker and is complemented by a walk-in pantry, demonstrating the careful attention to detail found throughout the home. A rare main-level bedroom with en suite bath, along with a dedicated private office, provides exceptional flexibility for guests, multi-generational living, or work-from-home convenience. Upstairs, you’ll find four generously sized bedrooms, each offering its own walk-in closet and own en suite bathroom —a rare and highly desirable feature. The primary suite serves as a luxurious retreat, complete with separate his-and-hers walk-in closets and a spa-inspired bathroom featuring a soaking tub and oversized walk-in shower. The finished lower level is designed for entertainment and relaxation, featuring a spacious recreation room, a dedicated theater room, and an optional bar area with its own pantry and possible wine storage room. An additional en suite bedroom on this level makes the space ideal for extended guests, in-laws, or a live-in nanny. Set on an exceptionally rare 2.19-acre homesite, the property offers endless possibilities for outdoor living, including space approved for a future pool, pickleball court, or custom outdoor entertainment retreat of your choice —creating the ultimate private backyard oasis. Life in Winchester on the Severn offers an unmatched lifestyle. Simply hop on your golf cart and head to one of the finest community beaches on the Severn River, where residents enjoy a playground, pavilion, sandy beach, swimming pier, kayak and paddleboard storage and launch, boat ramp, and breathtaking sunsets over the water. This is an extremely rare opportunity to create a custom residence in one of the area’s most desirable water-privileged communities—where luxury, space, and lifestyle come together seamlessly.

1603 Winchester Rd, Annapolis

Listing courtesy of Berkshire Hathaway HomeServices PenFed Realty. Contact:

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