Southwind Homes for Sale

Welcome to Southwind, a picturesque subdivision nestled in the charming town of Chester, Maryland, within the serene Queen Anne's County. This hidden gem offers a perfect blend of tranquility and community, making it an ideal choice for families, retirees, and anyone seeking a peaceful lifestyle without sacrificing convenience.

Southwind boasts a variety of beautifully designed homes that cater to diverse tastes and budgets. From modern single-family residences to cozy townhomes, you’ll find properties that reflect both elegance and comfort. Each home is thoughtfully crafted with spacious layouts, contemporary finishes, and lush outdoor spaces, perfect for enjoying Maryland’s stunning seasons. With homes for sale in Southwind, you have the opportunity to create your dream residence in a community that truly feels like home.

The subdivision is conveniently located just minutes from the Chesapeake Bay, offering residents easy access to waterfront activities, including boating, fishing, and scenic picnics. Additionally, Chester is known for its excellent schools, vibrant local shops, and delightful dining options, ensuring that everything you need is right at your fingertips.

Families will appreciate the close-knit community atmosphere, where neighbors become friends and local events foster a sense of belonging. Whether you’re strolling through the tree-lined streets or enjoying a sunset by the bay, Southwind invites you to embrace a lifestyle filled with warmth and connection.

Explore the homes for sale in Southwind today and discover the perfect place to call your own in this idyllic Maryland community!

Newest Southwind Homes for Sale

$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

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