Golf at Olde Cypress
The Club at Olde Cypress, its P.B. Dye-designed course, and how membership works for homeowners in North Naples.
The Olde Cypress Golf Guide
The Club at Olde Cypress is the private, privately owned country club at the center of Olde Cypress, a gated community of about 550 single-family homes in North Naples, Florida. Its P.B. Dye-designed 18-hole championship course is paired with a renovated 34,000-square-foot clubhouse, tennis, pickleball, bocce, a fitness center, and a pool, and social membership is tied to home ownership while golf membership is a separate, optional category.
That structure is the first thing to understand when comparing Olde Cypress with other North Naples golf communities. Owners join the club at the social level, and choose whether to add golf, rather than buying into a bundled golf community where golf is included.
Jeremy O’Guinn, Broker Associate and Certified Negotiation Expert with Downing-Frye Realty, helps buyers confirm the membership details in writing with the club before they make an offer.
The P.B. Dye Golf Course at Olde Cypress
Design, conditioning, and practice facilities
The course winds through the community on pine and cypress preserves, with homes set back along the fairways.
Design
An 18-hole championship layout by architect P.B. Dye, known for blending links-style and traditional features. Published sources list it at par 72.
Remastered Course
The club remastered the course in 2021 as part of a multimillion-dollar investment by its owner, followed by a renovation of the clubhouse interior.
Practice Facilities
A grass driving range, a putting green, and a golf practice facility support a full golf routine for members.
For the current scorecard, ratings, and tee options, contact the club at OldeCypress.com.
Olde Cypress Club Membership
Social and golf categories
Membership categories, availability, and fees change, so confirm every detail with the club for the specific address you are considering.
Social Membership
Tied to home ownership for residents who do not hold a higher category. It covers clubhouse dining, tennis, pickleball, bocce, the fitness center, the pool, and social events.
Full Golf Membership
Adds the championship course, the driving range, and member golf events to the club’s other amenities. Availability is limited and has included a waitlist.
Associate Golf Membership
A golf category the club has offered alongside Full Golf. Ask which golf categories are open now and how they differ.
Sources: The Club at Olde Cypress, published club and golf industry news, and MLS listing descriptions. Fees are not shown here. Confirm current terms with the club.
Beyond Golf at The Club at Olde Cypress
Dining, racquet sports, fitness, and social events
Dining and Social Life
Indoor and outdoor dining in the renovated clubhouse, including the Greenside Grille, and a year-round calendar of dinners, tastings, and events.
Tennis, Pickleball, and Bocce
Har-Tru tennis courts and active pickleball and bocce programs.
Fitness and Pool
A fitness center with wellness programming and a pool at the clubhouse.
What to Confirm Before Buying for the Golf
Questions to answer in writing with the club
Required membership
Confirm which membership the home requires and what it includes.
Golf availability
Ask whether golf categories are open, whether a waitlist applies, and whether a membership is available or included with a specific home.
Initiation fees and dues
Get current initiation fees and dues for each category in writing from the club.
Transfer terms
Ask how a membership transfers on resale and what happens to the fees you pay.
HOA terms
Confirm HOA dues, transfer fees, and any assessments for the specific address.
Setting and exposure
Compare golf course, lake, and preserve settings, and the sun exposure of the lanai.
Olde Cypress vs. Other Naples Golf Communities
How buyers compare golf structures
Golf structures differ across Naples, from private clubs with optional golf to bundled communities where golf is included. Compare the terms for the specific home you are considering.
Homes in Olde Cypress
Villas to larger estate homes around the club
See the latest Olde Cypress homes below, review the market data, or request a confidential valuation if you own in the community.
A Note From Jeremy
Broker Associate · Certified Negotiation Expert · Downing-Frye Realty
“At Olde Cypress, the club details matter as much as the house. I help buyers confirm the membership, fees, and transfer terms in writing before they make an offer, so the golf lifestyle they want is the one they get.”
Golf at Olde Cypress: FAQ
Common questions about golf and membership at Olde Cypress, Naples FL
What is The Club at Olde Cypress?
The Club at Olde Cypress is the private, privately owned country club at the center of Olde Cypress, a gated community of about 550 single-family homes in North Naples. It offers a P.B. Dye-designed 18-hole championship golf course, a renovated 34,000-square-foot clubhouse, tennis, pickleball, bocce, a fitness center, and a pool.
Who designed the golf course at Olde Cypress?
The 18-hole championship course at Olde Cypress was designed by P.B. Dye. The club remastered the course in 2021, and published sources list it as a par 72 of about 6,700 yards from the longest tees. Ask the club for the current scorecard and ratings.
Do I have to join the golf club to live in Olde Cypress?
Golf membership is optional. The club describes Social Membership as mandatory for residents who do not hold a higher category of membership, and it includes clubhouse dining, tennis, pickleball, fitness, and social events. Confirm the current requirements for the specific address with the club.
What golf membership categories does Olde Cypress offer?
The club has offered Full Golf and Associate Golf memberships, with availability that changes and, at times, a waitlist. Some categories have also been offered to non-residents. Ask the club which categories are open now and what the initiation fees and dues are.
What amenities does The Club at Olde Cypress offer besides golf?
Besides golf, the club offers a driving range and practice facility, a putting green, Har-Tru tennis courts, pickleball and bocce courts, a fitness center with wellness programming, a pool, indoor and outdoor dining, and a year-round social calendar.
Is Olde Cypress a private club?
Yes. The Club at Olde Cypress is a private, privately owned country club, and access to its facilities is through membership. Ask the club about guest and visitor policies.
What should buyers confirm about golf before buying in Olde Cypress?
Confirm which membership the home requires, whether a golf membership is available or included, the initiation fees and dues, and any transfer terms, then verify the HOA terms. Jeremy will help you collect these in writing from the club before you make an offer.
How do I start buying a home in Olde Cypress?
Decide whether golf matters to you and what style and size of home you want, then call or text Jeremy O’Guinn at 239-963-4474. Jeremy will show you homes in the right neighborhoods and help you confirm the membership details.
Explore More Ways to Search
Guides to help you compare Naples golf communities and plan your purchase.
Find Your Olde Cypress Home
Whether you want a villa near the clubhouse or a larger home on the course, Jeremy can help you find the right Olde Cypress fit, confirm the membership terms, and negotiate with confidence.
The data relating to real estate for sale on this web site comes in part from the Broker Reciprocity Program (BR Program) of M.L.S. of Naples, Inc. Properties listed with brokerage firms other than this company are marked with the BR Program Icon or the BR House Icon and detailed information about them includes the name of the listing brokers. The properties displayed may not be all the properties available through the BR Program. The information provided is for consumers’ personal, non-commercial use and may not be used for any other purpose.