Winchester On The Severn Homes for Sale

Welcome to Winchester On The Severn, a picturesque subdivision nestled in the heart of Annapolis, Maryland. This charming community offers a perfect blend of serene living and vibrant local culture, making it an ideal place for families, retirees, and professionals alike.

Winchester On The Severn boasts a stunning array of homes for sale, each uniquely designed to cater to a variety of tastes and lifestyles. From elegant waterfront properties with breathtaking views of the Severn River to cozy single-family homes surrounded by lush greenery, there’s something for everyone in this delightful neighborhood. The homes are characterized by their spacious layouts, modern amenities, and meticulous craftsmanship, ensuring comfort and style for all residents.

Living in Winchester On The Severn means embracing a lifestyle filled with outdoor adventures and community spirit. The nearby Severn River offers ample opportunities for boating, fishing, and kayaking, while the beautifully maintained parks and walking trails invite you to explore the natural beauty of the area. With its close proximity to downtown Annapolis, residents can enjoy a vibrant culinary scene, boutique shopping, and rich historical attractions, all just a short drive away.

Families will appreciate the highly-rated schools in the area, as well as the strong sense of community that Winchester On The Severn fosters. Whether you’re looking for a peaceful retreat or an active lifestyle, this subdivision offers the perfect backdrop for your next chapter. Explore the homes for sale today and discover the charm of Winchester On The Severn – where your dream home awaits!

Newest Winchester On The Severn Homes for Sale

$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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