Olde Cypress

Every owner is a social member of The Club at Olde Cypress: the membership comes with the home. Golf is a separate, optional membership, full or associate, and it is open to people who live outside the gates as well.

Dining, the fitness center and the pool, four clay tennis courts, two pickleball courts and three bocce courts.

Dues and membership terms are set by the club and change from season to season, so they are not quoted here. Ask Deidre for the current figures and how they compare with the clubs nearby.

Stock Development owns the club, not its members. The club charges no assessments and sets no food and beverage minimum, and the owner paid for the $16 million clubhouse renovation finished in the spring of 2026.

No. Olde Cypress is not in a Community Development District.

No. Its 540 homes are single-family homes and villas that are deeded as single-family homes.

Eighteen holes by P.B. Dye, par 72 and 6,711 yards from the back tees. Three holes run through preserve with no homes beside them, the twelfth has a 120-yard island green, and the greens were resurfaced and the tees and bunkers reworked in 2021. The reputation of the course is that it is very challenging. However, since the community was built in 2000, there are golfers in every age group and in every skill level, and the golfers are comfortable in the group that matches their needs.

It is guard-gated, and the gate sits beyond the clubhouse, so visiting golfers and event guests never drive through the residential streets. Members may keep and use their own golf carts.

No, and that is the wonderful aspect of the community. Since it is on the smaller side, everyone gets to know one another, and it is not all about the golf. The newly transformed clubhouse as of 2026 is beautiful, and many social members enjoy the amenities. Bocce is very popular for all ages, and it is organized and can get competitive. Since the community is not large, getting tennis or pickleball court times is easy.

Off Logan Boulevard at Immokalee Road in North Naples (34119), a mile and a quarter from Exit 111 on I-75.

Every Naples golf community has its own personality, and Olde Cypress has a combination of golf, club amenities, residential character and location that makes it distinctive. When I help buyers compare communities, I don’t tell them there is a best choice. Instead, I ask questions such as:

• How important is golf to you?
• How often would you like to play?
• Do you want a challenging golf course?
• Do you want an active social club?
• Are tennis and pickleball important to you?
• Do you want a large or smaller community?
• Do you prefer a community that has minimal renters?
• How important is proximity to the beach?
• Are you interested in joining a private beach club?
• What type of home are you envisioning? What price range are you expecting?
• What membership structure are you interested in?
• Would you like me to explain CDDs?
• What is your lifestyle now, and if you had a magic wand, what would you change?

The answers to these questions usually tell me much more about the right community than me listing every community in Naples.

Olde Cypress home values vary considerably depending on the property, view, location, size, condition, renovations and current market conditions. Since 2000, many homes in the community have sold and have been completely redone. These homes have not come back on the market yet, so the equity build-up is happening throughout the community, but buyers won’t see that when comps are run. Some homes have had multimillion-dollar renovations. A renovated home with a premium golf or lake view, or in Da Vinci with complete privacy, can have a very different value from an older home without those attributes. I help buyers and sellers evaluate homes in Olde Cypress and understand how individual property characteristics affect value.

Homes range in Olde Cypress from the high $600s for villas that have not been updated to homes over $3.3 million.

Pool surfaces, lanai flooring, flooring throughout the home, generators, buried propane tanks that can supply gas cooking ranges, garage air conditioning, garage flooring, panoramic screen cages, Storm Smart shutters, smart home electronics and remote access to home controls, to name a few.

Another conversation we have is lanai exposure. Many new buyers to Naples insist on only considering western exposures. If a buyer is planning on only staying in Naples for a couple of winter months, this could be important. However, the sun here does shift differently. Depending on where the home is on the lot, and if the home is a single story or not, sun exposure on the lanai and the pool will vary. Western exposure will need shades or awnings for summer enjoyment. Also, interestingly, northern exposure does not mean one is in the shade all day. Eastern exposure can have sun on your pool until mid-afternoon. It all depends on the home and its position on the lot. I always recommend the app SunCalc. You can insert the address and the day of the year to see where the sun falls. If you are in a single-story home and have a two-story home on either side of you, natural light will be limited in the home.