Grey Oaks Homes & Real Estate

Grey Oaks is the closest thing Naples has to a full country club community within minutes of downtown. It is also the one where the purchase price is not the whole cost, because club membership is mandatory and its initiation runs into six figures.

It sits east of Airport-Pulling Road between Golden Gate Parkway and Pine Ridge Road, about ten minutes from Fifth Avenue South. Estuary, the Estates and the villages share one gate but trade as three separate markets.

What Does Grey Oaks Cost?

Thirty-five homes sold between January and August 2026 at a median of $4,250,000. That single figure hides three quite different markets inside one gate, and the differences are large enough that a buyer comparing across them is not comparing like with like.

Estuary homes closed at a median of $9 million, the Estates at $6.2 million and the villages at $3.16 million. The table sets them side by side, including how long each took to sell.

Across all 35 sales the median was 96% of final asking price, median size 3,821 square feet and median days on market 44. That 96% is worth holding on to: it is a tighter market than the inland acreage neighborhoods, where the comparable figure runs closer to 92%.

Neighborhood by neighborhood

Grey Oaks runs as eighteen separate neighborhoods, each with its own association, and the differences between them are substantial: Isle Royale’s estates reach 12,000 sq ft, while L’Ermitage and Terra Verde are condominiums and coach homes of 2,200 sq ft upward.

Sales are reported by area rather than by neighborhood, so the table above gives the market and this one gives the choice. A buyer deciding between Torino and Traditions is choosing between villas of 3,900 to 5,000 sq ft and coach homes from 2,500.

The most expensive homes take the longest to sell

The pattern in the bottom row of that table is the opposite of what most buyers assume. The Estates, at a median of $6.2 million, cleared in 21 days. The villages, at half that price, took 37. Estuary, the most expensive tier in the community, took 132 days.

That is a thin-market effect rather than a weakness. Five sales in eight months means a buyer for a $9 million Estuary house arrives rarely, so the marketing period stretches. For a seller it means pricing patiently. For a buyer it means there is usually something available and time to look at it properly.

What the club actually includes

Three championship golf courses give 54 holes: the Pine and Palm on the main campus and the Estuary course in its own section. Beyond golf there are two clubhouses, a wellness center of around 30,000 square feet, Har-Tru tennis, pickleball, bocce, a resort pool and several dining venues.

Full golf membership is capped at roughly 780 across the three courses, which is why a waitlist can form and why golf-in-waiting and sports categories are offered as alternatives.

How does Grey Oaks compare?

Grey Oaks and Pine Ridge Estates closed 2026 within $25,000 of each other on the median, which makes them a genuine choice rather than a step up or down.

What separates them is everything around the house: Grey Oaks gives three golf courses, a gate and a club you must join; Pine Ridge gives an acre of land, no gate and no dues.