Winchester On The Severn Real Estate

Welcome to Winchester On The Severn, a picturesque subdivision nestled in the heart of Annapolis, Maryland. This charming community offers a unique blend of tranquility and accessibility, making it a perfect choice for families, retirees, and anyone seeking a serene lifestyle just moments away from the vibrant culture of the capital.

Winchester On The Severn is renowned for its stunning waterfront properties that boast breathtaking views of the Severn River. Imagine waking up to the gentle sounds of water lapping at the shore and enjoying your morning coffee while watching the sunrise over the horizon. The community is characterized by its beautiful homes, meticulously maintained landscapes, and a friendly atmosphere that fosters a strong sense of belonging among residents.

Nature lovers will appreciate the abundance of outdoor activities available in and around the subdivision. With easy access to parks, walking trails, and the scenic waterfront, residents can indulge in kayaking, fishing, or simply enjoying a leisurely stroll along the riverbanks. The community is also conveniently located near the historic charm of downtown Annapolis, where you can explore boutique shops, dine in exquisite restaurants, and immerse yourself in rich maritime history.

Families will find an array of top-rated schools and recreational facilities within close proximity, ensuring that children have access to quality education and fun activities. With its perfect blend of suburban tranquility and urban excitement, Winchester On The Severn truly offers a lifestyle that many dream of. Come and discover your new home in this enchanting community, where every day feels like a vacation!

Newest Listings in Winchester On The Severn

$799,999

4 Beds ⋅ 3 Baths

Please note, there is a basement in this home. See pictures. Welcome to Winchester On The Severn. One of Annapolis's most established waterfront community's. This home provides mature landscaping with a canopy of lovely trees and bushes both in the front and rear yard. Covered front porch! You will be pleased to enter a spacious foyer. Main level bedroom with a full bath to the left. A few steps up to the open floor plan with spacious living room that feeds into the dining room. Be prepared to enjoy the screened porch off the dining room. A wonderful spot to relax and enjoy the back yard. The eat in kitchen is filled with light! Comfortable family room is complimented with a wood burning fireplace. And you can also walk out from the family room to the back yard! The basement is dry and has a new 2025 heat pump. The 3 additional bedrooms have fresh paint. The larger bedroom is en-suite. Ready to know about the neighborhood? Amenities include private beach on the Severn River, marina, boat ramp, multiple piers, dog beach, beach pavilion, and the Chase Creek swim club. Nearby is the B&A trail. You may not want to leave the home but if you do it is a short ride to Annapolis and all major routes. Welcome. Enjoy

1518 Winchester Rd, Annapolis

Listing courtesy of Coldwell Banker Realty. Contact: kelly.thompson@cbmove.com

$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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