About Churchill Oaks
Churchill Oaks sits on Choctawhatchee Bay in North Santa Rosa Beach, gated and tucked into the bend where Churchill Bayou meets Hogtown Bayou, just north of Highway 98 and minutes from the Gulf. It is a bayfront community of only 102 homesites built around deep-water boating, preserved land, and full-time living rather than beach frontage, and getting that straight changes how you value it against anything on 30A. The draw here is not the sand. It is the water you can put a real boat on.
What actually defines it
The identity of this community is the bay and its private marina. Churchill Oaks has 36 private deep-water slips with shore power and fresh water, able to handle boats up to 70 feet, described locally as the first private deep-water marina built in this area in decades. From your slip you can run to Crab Island, Destin Harbor, Baytowne Wharf, and out to the Gulf, all from inside a residential neighborhood, which is genuinely rare on this coast. Add over half a mile of bayfront, an eight-foot elevated boardwalk running nearly a mile along the shoreline, and two spring-fed lakes stocked with bass and perch, and the whole place is built for people who live on the water.
The clubhouse backs that up. At more than 8,000 square feet it holds three pools (including a bayfront zero-entry), a full commercial kitchen, a media room, a fitness center, an outdoor bar, and large gathering rooms, and it is open to all owners. A planned phase two adds pickleball and basketball courts, grills, paddleboard racks, and an adults-only clubhouse.
The other defining trait is how lightly it is built with homes clustered into enclaves buffered by parks and preservation. Lots are large enough for courtyards and outdoor kitchens, the architecture holds to a Low Country and Colonial standard through an approved-architect list, and short-term rentals are not permitted. This is a full-time and second-home community, not a rental corridor.
One question decides more value here than any finish level: the boat slip. Slips are sold separately from the homes, they are limited, and demand has run ahead of supply. So the first thing to establish on any Churchill Oaks home is whether a slip conveys, and if it does not, whether one can even be had. That single detail can move the number materially, and it is the thing most buyers do not think to ask until late.
How buying works here, and why it matters
Churchill Oaks is still in build-out, so you are really looking at two different buys. One is a completed or under-construction custom home. The other is a vacant homesite you purchase and build on using an approved architect and builder. Those are very different transactions with very different timelines and risk, and the right move depends on inventory at the moment you are looking.
If you build, the approved architect and builder list controls who you can work with and the design standards are strict. That protects long-term value across the community, but it narrows your options, and pricing a build correctly (lot, hard costs, and a slip if you want one) takes someone who knows the local numbers. It is also worth knowing that new construction and developer-held inventory here has historically run through the developer's exclusive on-site listing agent, who represents the seller. Having your own representation across the table matters more in that setup than in an ordinary MLS resale.
On price, with only 102 homesites and thin inventory, the spread is wide. Completed homes generally run from the seven figures well into the multi-millions for bayfront estates, while vacant and premium bay or lake homesites price separately as their own entry point. The listings below carry the live numbers, but where a given property lands depends heavily on water frontage, whether a slip is included, and lot position.
Why work with me on Churchill Oaks specifically
I work the bay side of South Walton as closely as the beach side, and Churchill Oaks is a specific kind of buy: part real estate, part boat-slip strategy, part new-construction diligence. Most agents treat it like any other listing. It is not one.
The edge here is knowing which homes actually carry slips, which lots are worth building on, what an approved build really costs, and how to represent you against a developer's exclusive agent rather than walking in unrepresented. And in a community of only 102 homesites, knowing what is about to come available before it hits the market is most of the game.
The listings below are the starting point. If you are weighing Churchill Oaks against a Gulf-proximate 30A home, or against a community like Watersound Origins for full-time living, that trade-off is worth a real conversation. Reach out and let's have it.
