Cottages At Winding Creek
Homes for Sale in St. Augustine, FL

Cottages At Winding Creek market snapshot (as of August 5, 2026): the median sale price is about $280K ($183 per sq ft over the trailing 12 months of closed sales), a median 102 days on market for closed sales, and 1.5 months of supply, a balanced market. The trailing-12-month median is down 10% from the prior 12 months, computed from record-level realMLS closed sales (8 closings in the current window).

Cottages At Winding Creek is a gated community in St. Augustine, St. Johns County, built around a shared clubhouse, pool, tennis courts, and playground rather than large private lot amenities — the kind of trade-off that keeps maintenance simpler but ties buyers to HOA-run common areas.

The amenity package here is dense for the price point: a gated entry with a security gate, entry phone/intercom, and security fence, plus a clubhouse, pool, tennis court(s), and playground, with grounds maintenance and trash handled through the HOA. That combination points to a community built for low-maintenance ownership rather than large individual yards — buyers are paying for shared infrastructure and access control, not square footage on a private lot. As always with HOA-reported amenities, current access and condition should be verified directly with the HOA before writing an offer.

On the numbers, this is a market where the sample size matters more than usual. Seven closings and one active listing is not enough data to draw firm conclusions about direction, and the 11.1% year-over-year decline in median price should be read in that light — it is a real number, but it is also a number that a single high- or low-priced closing can move substantially. The 104-day median time on market, set against a seller-leaning supply picture of 1.5 months, suggests homes here sell on patience and correct pricing rather than on scarcity alone.

A community this thin on transaction volume punishes generic pricing advice — with only seven closings and one listing active, a comp-pull that does not account for condition and unit-level differences will mislead a seller or a buyer. Momentum treats a market like this as a case-by-case pricing exercise, weighing the $280,000 median and $184.79 per square foot against the specific unit rather than the community-wide average, and building offers or list prices around the real 104-day selling pattern instead of what a low months-of-supply figure implies on its own.

Confirm the current HOA dues, exactly what they cover, and any CDD bond or special assessment for a specific address before you offer.