255 Churchill Oaks Dr, Florida, 32459 | Santa Rosa Beach

Overview

The neighborhood

Churchill Oaks

Churchill Oaks is a private, gated waterfront community set along the quiet curve of Choctawhatchee Bay near Hogtown Bayou. Thoughtfully planned and intentionally low density, the neighborhood offers a peaceful alternative to the busier Gulf-front towns while remaining just minutes from the beaches of 30A.

One of the defining features of Churchill Oaks is its private deepwater marina, a rare amenity in South Walton. With slips designed to accommodate large vessels, the community supports a true waterfront lifestyle centered on boating, fishing, and life on the bay. The setting feels refined and serene, with an emphasis on natural beauty, privacy, and long-term livability.

Explore the latest listings and view homes for sale in Churchill Oaks below. Browse available properties across one of the most desirable areas along Florida’s Emerald Coast.

Lifestyle

Life in Churchill Oaks is centered on water, nature, and connection. Residents enjoy easy access to the bay for boating, paddleboarding, kayaking, and fishing, often stepping directly from their neighborhood into the water. The marina is both a functional amenity and a gathering place, reinforcing the community’s strong relationship with the bay.

The clubhouse serves as the social heart of the neighborhood, featuring bayfront zero-entry pools, open-air gathering spaces, and sweeping water views. Regular community events and shared amenities create a welcoming, close-knit atmosphere while still allowing residents to maintain a sense of retreat.

Despite its tranquil setting, Churchill Oaks is conveniently located near South Walton’s dining, shopping, golf courses, and coastal towns. Residents enjoy the balance of a quiet home environment with easy access to the broader 30A lifestyle.

Architecture

Homes in Churchill Oaks reflect a refined Low Country architectural style, emphasizing timeless design, quality craftsmanship, and livable elegance. Residences are designed with open floor plans, abundant natural light, and a strong connection between indoor and outdoor spaces.

Many homes feature courtyards, covered porches, and outdoor kitchens, allowing everyday living and entertaining to extend naturally outside. The community places a strong emphasis on preservation, with a significant portion of the neighborhood dedicated to green space. Mature live oaks, magnolias, and longleaf pines frame the homes, creating a setting that feels established, cohesive, and deeply connected to its surroundings.

Travel & Access

Getting There
Churchill Oaks is a private, gated waterfront community situated along Churchill Bayou and Choctawhatchee Bay in South Walton. Located just north of Scenic Highway 30A, the community offers a tranquil bayfront setting with convenient access to coastal destinations and regional routes via Highway 98.

Airports
Northwest Florida Beaches International Airport (ECP) is approximately 45 minutes east, offering nonstop service to major U.S. cities. Destin–Fort Walton Beach Airport (VPS) is about one hour west and provides additional commercial flight options. Private and charter aviation is available at nearby regional airports.

Drive Times
• ~10 minutes to Seaside
• ~15 minutes to Grayton Beach
• ~45 minutes to ECP Airport

Water Access
Churchill Oaks offers direct access to Choctawhatchee Bay via its private marina, with deepwater boat slips available to residents. From the bay, boating access extends to the Gulf of Mexico and surrounding coastal waterways.

Local Transportation
The community is primarily accessed by car, with internal walking trails supporting on-site mobility.

Seasonal Considerations
Churchill Oaks’ inland bayfront location allows for smoother access during peak 30A travel periods, offering a quieter arrival experience compared to Gulf-front communities.