Olde Cypress market snapshot
Homes, condos and townhomes. Source: Naples MLS listing data, updated October 28, 2026. Information deemed reliable but not guaranteed.
About Olde Cypress
Olde Cypress is a private, gated golf community in North Naples, encompassing approximately 540 acres of lakes, golf and landscaped residential neighborhoods. The community includes 550 single-family estate homes and attached villa residences arranged around an 18-hole P.B. Dye-designed championship golf course. Homes range from lower-maintenance villa-style properties to substantial estate residences, with many enjoying golf course, lake or landscaped views and private outdoor living areas.
The lifestyle at Olde Cypress is centered around The Club at Olde Cypress, but buyers should understand that this is not a bundled-golf community. Every homeowner is required to maintain at least a Social Membership, which provides access to the clubhouse, dining, fitness, swimming, tennis, pickleball and social amenities. Golf is available through separate Full Golf and Associate Golf memberships, allowing residents to choose whether golf should be part of their lifestyle. This structure makes Olde Cypress particularly appealing to households that want a private country club environment while retaining flexibility over the level of golf access they purchase.
Why People Like the Olde Cypress Community
- P.B. Dye Championship Golf: The private 18-hole course provides a distinctive golf experience for residents who choose an appropriate golf membership.
- Flexible Membership Structure: All homeowners participate in the Club through Social Membership, while Full and Associate Golf memberships provide additional golf privileges.
- Diverse Luxury Housing: Attached villas, single-family homes and substantial estate residences provide different options for size, maintenance and privacy.
- Strong Non-Golf Amenities: Fitness, swimming, tennis, pickleball, bocce, dining and social programming make the Club relevant even for residents who do not play golf.
- Golf and Lake Settings: Many residences enjoy views across the course, lakes and landscaped surroundings.
- Active Club Lifestyle: Dining, entertainment, sports, tournaments and organized events provide numerous opportunities for residents who enjoy an active social environment.
What You Need to Know About Living in Olde Cypress
- Social Membership Is Mandatory: Every Olde Cypress homeowner who does not hold a higher membership category must maintain a Social Membership at The Club at Olde Cypress.
- Golf Is Not Bundled With the Home: Purchasing a residence does not automatically provide golf privileges. Full Golf and Associate Golf memberships are separate membership categories.
- The Golf Club Is Separate From the Residential Association: The Club and golf course are privately owned and operated separately from the Olde Cypress residential community, an important distinction when evaluating fees and responsibilities.
- There Are Multiple Ownership Costs: Buyers should consider homeowners association obligations and Club membership expenses together when evaluating the total cost of ownership.
- Homes Vary Considerably: Residence type, renovations, hurricane protection, private pools, outdoor living and other features differ throughout the community.
- Current Rules and Membership Terms Should Be Verified: Club dues, golf membership availability, association fees, leasing, pets and other requirements should be reviewed when considering a specific property.
Current listings
Olde Cypress Homes for Sale
See the newest homes for sale in Olde Cypress, updated throughout the day from the Naples MLS. Want a private showing or an honest read on value? Call Renee Hahn at (239) 287-2576.
The source of this real property information is the copyrighted and proprietary database compilation of the M.L.S. of Naples, Inc. Accuracy of this information is not warranted or guaranteed. Information should be independently verified if any person intends to engage in a transaction in reliance upon it.
Olde Cypress Amenities
The Club at Olde Cypress serves as the social and recreational center of the community, offering both indoor and outdoor dining, gathering spaces and an extensive calendar of member activities. Dining ranges from casual experiences to more refined settings, while member events, entertainment and social programming create an active club environment throughout the year. Social Membership provides Olde Cypress homeowners with access to these clubhouse privileges without requiring them to purchase golf membership.
Fitness and recreation extend well beyond golf. Members have access to a fully equipped fitness and wellness center, swimming pool, tennis, pickleball and bocce, with organized programming available for residents who enjoy active recreation. Tennis and pickleball include opportunities for instruction, leagues and social play, while bocce adds another recreational and social option to the Club lifestyle.
For golfers, the centerpiece is the 18-hole P.B. Dye-designed championship course, supported by practice facilities, professional instruction, tournaments and organized golf events. Full Golf Membership provides year-round golf access, while Associate Golf Membership provides a different level of seasonal golf privileges. This tiered structure allows homeowners to choose the golf experience that best matches how frequently they expect to play rather than requiring every resident to support a bundled golf membership.
One unusual feature for resident golf members is the ability, subject to Club requirements and applicable fees, to use privately owned golf carts on the course. For homeowners who live within the community and enjoy moving between their residence, Club and golf course by cart, this can be a meaningful lifestyle benefit.
The Club’s dining, fitness, swimming, racquet sports, bocce, golf and extensive social calendar create a country club lifestyle that is not dependent solely on golf. That distinction is important at Olde Cypress because Social Membership is the foundation of resident Club participation, while golf remains an optional additional membership choice.
What Is Near Olde Cypress?
Downtown Naples (5th Avenue South): 10.4 miles
Closest beach: Vanderbilt Beach, 6.8 miles
RSW Airport: 18 miles
Notable shopping & dining nearby: Shoppes of Pebblebrooke, 1.6 miles
Closest park: Max A Hasse Jr Community Park, 4.2 miles
(Distances are approximate straight-line distances.)
Olde Cypress Floor Plans
Floor plans are provided as a complimentary resource to help you understand the layouts available in Olde Cypress. Plans and specifications can change, so confirm details for any specific home.
View Olde Cypress floor plans (PDF)
Where Is Olde Cypress?
Olde Cypress FAQ
Where is Olde Cypress located?
Olde Cypress is a private golf community in North Naples, covering roughly 540 acres of lakes, golf and landscaped neighborhoods.
What types of homes are in Olde Cypress?
Olde Cypress has 550 residences, a mix of attached villas and single-family estate homes set around the golf course. Homes range from lower-maintenance villas to substantial estates, many with golf, lake or landscaped views.
Is club membership required in Olde Cypress?
Yes, every homeowner must hold at least a Social Membership at The Club at Olde Cypress, but golf is not bundled. Full Golf and Associate Golf memberships are separate, optional categories, and the Club operates separately from the residential association, so budget for both HOA and Club costs.
What amenities does Olde Cypress offer?
The Club offers indoor and outdoor dining, a fitness and wellness center, a pool, tennis, pickleball, bocce and a busy social calendar. Golfers have an 18-hole P.B. Dye-designed championship course with practice facilities, instruction and tournaments.
Can I use my own golf cart at Olde Cypress?
Resident golf members may be able to use privately owned golf carts on the course, subject to Club requirements and fees. It is a fun perk for anyone who likes to cruise from home to the Club to the first tee.
Last updated October 2026 by Renee Hahn, Your Naples Expert. Community details, fees and amenities can change, so confirm specifics for any home you are considering.
