NAPLES, FLORIDA · LIVINGSTON ROAD · EST. 1981

Wyndemere

Wyndemere is a private, guard-gated club community in central Naples — 634 homes in 16 neighbourhoods on about 450 acres behind a guarded entrance on Livingston Road, directly across from Grey Oaks, built around the member-owned Wyndemere Country Club. Membership is not an option here: every owner holds a club membership, with Sports as the minimum tier and Golf as the elective upgrade. Opened in 1981 and built out through the 1980s and 1990s, it is one of Naples' established club communities — mature landscaping, an Arthur Hills golf course, and homes from mid-rise condominiums to custom estates. This guide covers what buyers actually ask us: how the membership works, what the layered fees look like in real listings, how the neighbourhoods differ, the schools, and the market.

LAST UPDATED: OCTOBER 2026 · ASSOCIATION FIGURES AS OF EARLY-2026 LISTINGS WHERE DATED; MARKET DATA: DIRECT MLS PULL, OCTOBER 31, 2026

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The market right now

Start with the warning, because this community's headline number needs one: Wyndemere trades only about 46 homes a year, spread across mid-rise condominiums, villas and custom estates, so the $1,020,000 all-property median sold price is mix-driven — it records what sold, not what any particular home costs, and it should never be read as "Wyndemere homes cost $1M." Read the market by the format you are shopping: over the last twelve months single-family homes closed at a median of $1,335,000 across 20 sales, while condominiums, villas and townhouses closed at a median of $737,500 across 26 sales. Supply is genuinely thin — just 3 homes are actively listed, at a median list price of $725,000, with 4 more under contract — 0.8 months of inventory, a considered market in a community where most homes change hands inside the gates' own rhythm.

Market data: Southwest Florida MLS (Matrix) direct pull, Development = WYNDEMERE, October 31, 2026. Refreshed monthly — see our full Naples market report.

What it costs to own in Wyndemere — three layers, kept separate

There is no single Wyndemere fee, and any page that quotes one is guessing. Ownership here is a stack of three layers — a master association fee, a fee to your own neighbourhood's association where your section has one, and the mandatory club layer — and the layers are printed separately below, because adding them into one community figure would hide exactly the differences that decide what a specific home costs to carry. One more caution from the listings themselves: the recurring-fee totals printed on individual listings include charges their own itemised fields do not break out, so this page never quotes a listing total. Underwrite the specific home, layer by layer, from its estoppel.

The honest summary: a dated master fee, a section fee that depends entirely on which of the 16 neighbourhoods you buy in, and a mandatory club membership whose current terms only the club can quote. The number to underwrite is the stack for your section and your tier — not a community average, because there isn't one.

The club — membership comes with the home; the tier is your choice

Wyndemere Country Club, at 700 Wyndemere Way, is a member-owned club, and membership is mandatory for owners — each homeowner is required to maintain a club membership for the duration of ownership. The club offers two memberships: Sports, the mandatory minimum tier, and Golf, the elective upgrade. That distinction is the one buyers most often get wrong about Wyndemere: the membership goes with the home, but golf does not — you must hold a membership, and you choose whether it includes golf. Confirm current initiation, dues and what each tier includes directly with the club; it publishes no schedule, and this page prints no figures for it.

The golf. 27 holes designed by Arthur Hills, in three nine-hole courses played in 18-hole combinations, with a double-ended driving range, short-game area and putting greens — and a newer indoor golf training centre with simulators for summer and rainy-day work.

Beyond golf. 10 Har-Tru tennis courts (four lighted, with stadium seating), pickleball courts, bocce courts and croquet lawns; a resort-style zero-entry infinity pool with lap lanes and poolside service; a fitness centre with a full-service spa and salon; and clubhouse dining across casual and formal venues, including the Tiebreaker café. The club is a 2025–2026 Platinum Club of America, and the course has held Certified Audubon Cooperative Sanctuary status (Audubon International) since 2001 — an environmental certification for golf properties. The renovated clubhouse reopened in January 2013.

Homes — sixteen neighbourhoods, four formats

Sixteen neighbourhoods share the gates, and they are not one product repeated: Wyndemere runs from mid-rise condominiums to custom estates of 4,500+ square feet, with golf-course, lake and preserve views throughout.

Single-family and estate neighbourhoods — Mahogany Bend, the largest single-family section (91 homes on roughly third-acre lots); Grasmere, 48 custom homes of 3,200+ square feet on the southern side; Rosemeade, estate homes averaging about 3,500 square feet on cul-de-sacs; Glendevon, 36 homes of about 2,300–2,600 square feet within walking distance of the clubhouse; Coco Plum, 26 single-family homes of about 1,900–2,500 square feet with New England-style exteriors (the Golf Cottages sit in this family); plus The Estates, Edgewood and the Wyndemere Lodgings sections. Best for: full-time residents and buyers who want a house, a lot and the club life around both.

Villas and patio homes — Villa Floresta, 64 patio homes, most with private screened pools and their own gated entry; Mahogany Run, 15 detached villas of about 2,200–3,300 square feet; Glen Meadow, 13 single-family villas of about 2,500–3,000 square feet; Pond Apple Preserve, 36 attached patio homes of about 2,184–3,224 square feet; Amblewood, 42 attached villas of about 1,500–1,940 square feet in three floor plans; and Water Oaks, attached villas of about 1,650–2,258 square feet near the clubhouse. Best for: the club address with association-handled exteriors and, in many sections, a private pool of your own.

Condominiums — the Commons at Wyndemere (also coded Cypress Commons in MLS records): the mid-rise buildings at 100–400 Wyndemere Way, built from 1982, the community's original condominium stock; and Courtside Commons, on Courtside Drive by the tennis centre. Best for: lock-and-leave ownership at the lowest entry point inside the gates — with the section's own fee layer confirmed per home (see the fee section above).

A short history — opened in 1981, mature ever since

Wyndemere Country Club opened its gates in 1981, and the community was built out neighbourhood by neighbourhood through the 1980s and 1990s — the Commons buildings date from 1982, and homes across the sections followed over the next two decades. The clubhouse was renovated and reopened in January 2013. What that timeline buys a purchaser today is the thing new construction cannot sell: a finished, fully grown-in club community — canopy trees, established streetscapes and a club with four decades of membership behind it — in the middle of Naples rather than at its expanding edge.

Schools

Wyndemere addresses are zoned for Poinciana Elementary School, Gulfview Middle School and Naples High School (Collier County Public Schools) — the same trio in current records for addresses at both ends of the community. School zoning is address-specific; confirm with the district for a particular home.

School assignments are per Collier County Public Schools zoning — confirm for your specific address with CCPS before you buy. Assignments shown as of October 2026.

Wyndemere questions, answered

Where exactly is Wyndemere?
In central Naples, behind its guarded entrance on the east side of Livingston Road — directly across Livingston Road from the entrance to Grey Oaks, between Golden Gate Parkway to the south and Pine Ridge Road to the north, west of I-75. ZIP 34105, in unincorporated Collier County.

Do I have to join the club?
Yes. Membership in Wyndemere Country Club is mandatory for owners, for the duration of ownership. What you choose is the tier: Sports is the mandatory minimum, and Golf is the elective upgrade.

What are the club's initiation and dues?
The club publishes no initiation figure or dues schedule — pricing is by inquiry to the club, so this page prints none. Joining carries a one-time capital assessment fee and annual capital dues exist, without published amounts. Confirm the current initiation, dues and tier privileges with the club before you write an offer, and budget them as a real layer of the carrying cost.

How much are the HOA fees in Wyndemere?
Budget a stack, not a single fee: the master association fee was $1,227 per quarter in early-2026 listings; your neighbourhood's own association fee comes on top where your section has one — documented listings run from $880/qtr in a single-family section to $3,040–$3,917/qtr in the condominium sections — and the mandatory club membership is a third layer, confirmed with the club. There is no CDD.

What kinds of homes are in Wyndemere?
Four formats across 16 neighbourhoods: custom estate and single-family homes, detached and attached villas and patio homes, and low-/mid-rise condominiums — from about 1,300 sq ft condominiums to estates of 4,500+ sq ft, with golf-course, lake and preserve views.

What schools serve Wyndemere?
Poinciana Elementary School, Gulfview Middle School and Naples High School (Collier County Public Schools), in current records for addresses at both ends of the community. Zoning is address-specific — confirm for your specific address with CCPS before you buy.

Is Wyndemere gated, and is it 55+?
Gated, yes — a private, guard-gated community entered from Livingston Road. 55+, no — it is an all-ages community.