Olde Cypress

Make a two on the twelfth hole at Olde Cypress, a short par 3 to an island green, and you get to ring the Birdie Bell. An osprey pair is often seen in the tall pine by the first tee. Downstairs at the clubhouse, the Greenside Grille turns out hand-stretched pizzas from its own pizza oven, and its tables, some covered and some open-air, look across the course past fire pits and an outdoor bar with TVs.

The club puts Olde Cypress at about 550 homes on some 540 acres of North Naples, all houses and villas, wrapped around a private golf course. Treeline Drive, the way in, leaves Logan Boulevard North heading east a short way above Immokalee Road. The Club at Olde Cypress stands at 7165 Treeline Drive on the near side of the gate, so the club building sits outside the gated streets while the course runs through and around the homes. The club calls Olde Cypress a gated community.

How does the P.B. Dye course play?

As a par 72 that mixes links and traditional styles, with sculpted bunkers, lakes and changes in elevation. From the Champ tees P.B. Dye's 18 holes stretch to 6,711 yards, and from the Calusa tees they shrink to about 4,100. Three holes run through preserve with no houses beside them, the thirteenth and fourteenth among them. In 2021 the greens, practice green and chipping area were resurfaced with TifEagle Bermuda, and the driving range gained artificial-turf hitting stations.

Tuesday is Ladies' Day, with 18-hole groups in the morning and 9-hole groups after lunch. Wednesday is Men's Day, an ABCD format with lunch afterwards. Set Sundays in season bring themed couples rounds with dinner to follow, and a monthly interclub team travels to other courses. Fixtures run from the Cypress Cup member-guest and the Tradition member-member to club championships, Glow Ball and an Italian Open.

When the weather turns, a Full Swing simulator room in the clubhouse carries more than 45 courses, for practice, lessons and club fittings. From May 1 to October 31, the club's reciprocal list opens more than 40 private clubs across Southwest Florida to its members.

Clay courts, bocce and birding: what else is on the property?

The racquets complex pairs four clay courts for tennis, with stadium seating, and two for pickleball. Team tennis, daily doubles, round robins, clinics, camps and private lessons fill the program, with a Fast Feed clinic on Saturday mornings and pickleball clinics for beginner and intermediate players on alternate Saturdays.

Three bocce courts, lit and shaded, opened in 2025, and the club started co-ed bocce leagues that October. The fitness center, 4,000 square feet of cardio and strength equipment plus an aerobics room, opens daily, with group classes and personal training, and there's a club pool too.

The grounds staff keep purple martin houses and owl boxes. Once a year, usually in February or March, a specialist leads a two-hour birding walk across the property at daybreak.

What goes on at the clubhouse through the year?

The clubhouse reopened in 2026 after a year-long rebuild. Upstairs, a wraparound bar anchors the Grille Room and the Main Dining Room, where jackets aren't required and, at the reopening, the club set dinner at up to five nights a week. Off to the sides are a Private Dining Room lined with wine racks under a vaulted ceiling, the Cypress Room, home to a grand piano, and the Club Room with its billiards table.

Standing events on the club calendar include a Welcome Back party, the Holiday Dinner Dance, Casino Night, outdoor concerts, wine tastings, luaus and South Beach parties. Summer brings happy hour at the bar on Tuesdays and Fridays and Tuesday Tunes once a month. Through the year there are a monthly book club, card tables for bridge, mah jong and canasta, and a learn-to-play mah jong series.

What is within a half-hour drive?

All six, measured by road from the gate on Treeline Drive, with times for clear roads that season traffic stretches.

• NCH North Naples Hospital, about 4.6 miles, roughly 9 minutes
• Delnor-Wiggins Pass State Park, 6.9 miles, roughly 14 minutes
• Mercato, 7.2 miles, roughly 13 minutes
• Vanderbilt Beach, 8.3 miles, roughly 16 minutes
• Fifth Avenue South, 14.4 miles, roughly 23 minutes
• Southwest Florida International Airport terminal, 21.8 miles, roughly 28 minutes

What do houses and villas sell for at Olde Cypress?

There are two kinds of home and no condominiums. The detached houses are nearly all single-story ranch plans, the villas are attached, and the oldest were built in 2001.

Houses run from about 1,800 to about 5,550 square feet and villas from about 1,780 to about 2,150, with 2 to 4 bedrooms. Between April 2025 and August 2026, houses sold from the $770,000s to around $2.6 million. Villas sold from the $630,000s to around $800,000, a band that rests on five sales.

Does everyone who lives here have to join the club?

Yes, at least at the social level. The club states that its Social Membership is mandatory for each resident without a golf category, and that only people living inside the gates can hold it. Social covers club parties, dining, tennis, pickleball and fitness. Social carries dues of its own, a fixed cost of living here that the club doesn't publish, so have the club put the figure on paper first.

Golf is the optional step up. Full Golf gives unlimited play, with tee times bookable seven days out. Associate Golf gives limited play from November to April and unlimited play from May to October, along with the practice facilities all year and the whole clubhouse. In October 2026 the club listed both golf categories as open to residents and to people living elsewhere. Members who own a golf cart can drive it on the course by paying the club's annual cart plan fee.

Who does the club's "no assessments" promise cover?

Club members, and nobody else. The club is non-equity and privately owned: STOCK Development, the builder behind the community, owns it, its hospitality division runs it, and members hold no share and have no vote. The club says it imposes no food-and-drink minimum on members and does not assess them to pay for club improvements. STOCK paid for the 2025-26 clubhouse rebuild itself.

For the homeowners' association, budget around $1,000 a month. Set toward the high side on purpose, that number is not the middle, and plenty of homes here sit below it.

Nothing in the club's promise reaches the association. The homeowners' association at Olde Cypress can levy assessments of its own.