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

Cottages At Winding Creek market snapshot (as of September 19, 2026): the median sale price is about $282K ($187 per sq ft over the trailing 12 months of closed sales), a median 92 days on market for closed sales, and 2.0 months of supply, a balanced market. The trailing-12-month median is down 8% from the prior 12 months, computed from record-level realMLS closed sales (6 closings in the current window).

In ZIP 32086 (St. Augustine), 453 homes closed in the last 12 months at a median of $320K ($201/sq ft), down 4.5% year over year, with a median 68 days on market. Right now 119 active and 34 pending listings put supply at about 4.7 months — a buyer's market. See the live ZIP 32086 housing market and the St. Johns County market.

realMLS (Northeast Florida) sales records identify 61 homes in Cottages At Winding Creek that have changed hands since 2009, built between 2007 and 2010 (median 2010), with a median living area of about 1,594 sq ft and a typical 3-bedroom, 2.5-bath layout; 95% are condominiums. Source: realMLS (Northeast Florida) closed-sale history compiled by Momentum Research; counts reflect homes with a recorded MLS sale, not every home in the community.

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.

Listings in this community report association dues of about $299 per month ($3,588 a year) — the median AssociationFee across 49 MLS records, normalised to a monthly figure; most are billed monthly. Dues change with budgets and can differ by section or product type; confirm the current figure with the association before you offer. Source: MLS listing records, 2026-09.

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