Winchester On The Severn Real Estate

Welcome to Winchester On The Severn, an enchanting subdivision nestled in the heart of Annapolis, Maryland, within the picturesque Anne Arundel County. This charming community offers a unique blend of serene waterfront living and vibrant suburban amenities, making it an ideal place to call home.

Winchester On The Severn boasts stunning views of the Severn River, where residents can enjoy tranquil mornings and breathtaking sunsets. The neighborhood is characterized by its beautifully designed homes, many of which feature classic architectural styles and lush, well-maintained landscaping. With tree-lined streets and a friendly atmosphere, this community fosters a sense of belonging and camaraderie among its residents.

One of the standout features of Winchester On The Severn is its proximity to Annapolis, the state capital, which is renowned for its rich history, vibrant arts scene, and delectable dining options. Residents can easily explore the charming downtown area, filled with boutiques, galleries, and waterfront parks. For those who appreciate outdoor activities, the nearby parks and nature trails provide ample opportunities for hiking, biking, and enjoying the beauty of Maryland’s natural landscapes.

Families will also appreciate the top-rated schools within the area, ensuring a quality education for children of all ages. With its blend of natural beauty, community spirit, and convenient access to urban amenities, Winchester On The Severn truly embodies the best of Maryland living. Whether you’re seeking a peaceful retreat or an active lifestyle, this subdivision has something for everyone. Come discover your dream home in this idyllic setting!

Newest Listings in Winchester On The Severn

$680,000

3 Beds ⋅ 2 Baths ⋅ MDAA2155150 MLS

Don't miss this incredible opportunity to own a piece of one of the area's most coveted neighborhoods - Winchester on the Severn! From the moment you arrive, you'll feel right at home. Step onto the charming wrap-around front deck, perfect for relaxing and taking in the neighborhood's beautiful surroundings. Inside, the spacious family room is anchored by a classic brick-front fireplace, setting a warm and welcoming tone throughout. The open layout flows seamlessly from the living room into the dining area and sitting room, making it ideal for everyday living and entertaining alike. The kitchen features stainless steel appliances, granite countertops, and gas cooking. Three generous bedrooms, including the owner's suite, are all conveniently located on the main level. The lower level offers the perfect flex space, whether you need a family room, home office, or den, complete with a full bath, laundry room, and direct entry into the garage. Head outside to enjoy a private patio with a fire pit, the perfect spot for unwinding under the stars, and a dedicated woodworking shed ready for your next project. The community amenities include a private beach on the spectacular Severn River with a pavilion, a pier ideal for fishing and crabbing, kayak and paddle board storage, a neighborhood pool and swim club, a dog-friendly beach, and a playground. All of this just minutes from major commuter routes 50 & 97 and close to downtown Annapolis, by car or by boat.

1505 Riverdale Dr, Annapolis

$2,500,000

6 Beds ⋅ 7 Baths ⋅ MDAA2142274 MLS

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

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