Southwind Real Estate

Welcome to Southwind, a picturesque legal subdivision nestled in the charming town of Chester, Maryland. Located in Queen Anne's County, Southwind embodies the perfect blend of serene landscapes and vibrant community living. This idyllic neighborhood is known for its spacious lots, beautifully maintained homes, and a welcoming atmosphere that makes it an ideal place for families, retirees, and everyone in between.

One of the standout features of Southwind is its proximity to the stunning Chesapeake Bay. Residents enjoy easy access to waterfront activities, including boating, fishing, and kayaking, making it a paradise for outdoor enthusiasts. The lush greenery surrounding the subdivision provides a tranquil backdrop, perfect for morning strolls or afternoon picnics in the park.

Southwind also boasts a strong sense of community, with friendly neighbors who take pride in their homes and surroundings. The subdivision hosts various community events throughout the year, fostering connections and creating lasting friendships. With well-maintained roads and public spaces, it’s easy to see why so many choose to call Southwind home.

Education is a priority in this area, with highly-rated schools just a stone's throw away, ensuring that children receive the best possible education. Additionally, Chester's convenient location provides easy access to major highways, making commutes to nearby cities a breeze.

Whether you’re seeking a peaceful retreat or an active lifestyle, Southwind is the perfect place to plant your roots. Discover the charm of this exceptional subdivision and experience the warmth of community living in Chester, Maryland. Your dream home awaits!

Newest Listings in Southwind

$2,400,000

4 Beds ⋅ 4 Baths

Discover an exquisite Mediterranean-style residence nestled in the prestigious Southwind community, where luxury meets comfort while enjoying breathtaking sunset views. This stunning 4-bedroom, 3.5-bathroom home boasts 4,331 sq. ft. The gourmet kitchen features high-end stainless steel appliances, including a built-in microwave, wall oven, and a sleek cooktop, ensuring culinary excellence. Step outside to your private oasis, where a concrete pool invites relaxation amidst lush landscaping on a generous 1.2-acre lot that includes a covered built in Lynx grill and bar seating. Enjoy direct access to Cox Creek, complete with a private dock for fishing, kayaking, or simply soaking in the serene water views. With a double sided fireplace and three tankless water heater, this home combines elegance with modern convenience, making it a true sanctuary. The main living room features sky high ceilings and a wet bar making hosting a snap and flows into the added sunroom that features heated tile flooring. And the three season room off the back is the perfect gathering space with a wall of sliders to maximize the view. Meticulously maintained and thoroughy enjoyed by the original owners. The expansive rear yard and rip-rap shoreline enhance the outdoor experience, while the community amenities, including a beach, tennis/basketball courts, and fishing pier and boat launch, offer an exclusive lifestyle on Maryland's Eastern Shore.

2882 Cox Neck Rd, Chester

Listing courtesy of Wilson Realty & Staging LLC. Contact: 4103042250

$1,195,000

4 Beds ⋅ 5 Baths

Located in the prestigious Southwind community, a penisula between Crab Alley Bay & Cox Creek, this elegant contemporary ranch-style home offers an unparalleled lifestyle of luxury and comfort. Spanning over 4,400 sq. ft. of finished space, the interior boasts elegant marble flooring, complemented by crown moldings and built-ins that enhance its sophisticated charm. The gourmet kitchen, featuring upgraded countertops and a spacious island, flows seamlessly into the family room, perfect for entertaining. Relax in the primary suite with a lavish bath or unwind in the inviting family room by the fireplace with views out to Crab Alley. Three additional bedrooms (or two bedrooms and an office) and two baths round out the main level that offers sweeping scenic views from every vantage point. Step outside to discover a private oasis on 1.25 acres, complete with extensive hardscaping, a heated in-ground pool, and a soothing hot tub. Enjoy picturesque water views out the front and back, with access for kayaking and boating. The community amenities, including a beach, clubhouse, and tennis courts, elevate your living experience. This home is not just a residence; it's a lifestyle waiting to be embraced and enjoyed. Start living your best 'Shore Life' at 2855 Cox Neck Rd.

2855 Cox Neck Rd, Chester

Listing courtesy of Wilson Realty & Staging LLC. Contact: 4103042250

Start Your Search