Olde Cypress Naples, FL Homes for Sale & Community Guide
A private gated golf and country club community in North Naples with approximately 550 residences, an established P.B. Dye-designed golf course and a mix of villas through larger estate homes.
An established North Naples golf community with more variety than first meets the eye.
Olde Cypress is a gated golf and country club community in North Naples, just east of I-75 off the Immokalee Road corridor. Established in 2000, the community spans approximately 540 acres and includes about 550 residences.
Homes are arranged throughout distinct residential sections with golf-course, lake and preserve settings. Housing ranges from attached villas and smaller single-family residences to larger custom and estate homes.
That variety is important for buyers. Olde Cypress is not a community where every street contains the same builder, floor plan or style of home.
Olde Cypress homeowners become social members of The Club at Olde Cypress, providing access to club amenities. Higher membership levels, including golf, are optional. The golf club is separately owned and managed rather than being an asset of the residential master association.
Olde Cypress at a glance.
Olde Cypress combines the scale of an established golf community with a relatively limited number of residences. Its multiple residential sections create noticeable differences in home style, size and ownership experience.
The individual neighborhood matters here.
Olde Cypress was developed in stages, which helps explain the variety of real estate found behind the gates. Attached villas, single-family homes and larger estate properties can all be found within the community.
Homes also differ considerably by construction era, floor plan, renovation level, garage configuration, outdoor living space and homesite.
Golf, lake and preserve positions can further separate otherwise similar properties. For that reason, buyers should look beyond a community-wide average when comparing Olde Cypress homes.
From villas to custom estate homes.
Olde Cypress offers a broader mix of housing than many buyers expect from a community of roughly 550 residences. The size, design and character of a home can change significantly from one residential section to another.
Attached Villas
Villa residences provide an alternative for buyers who prefer a smaller home footprint while remaining within the Olde Cypress club community.
Single-Family Homes
Single-family residences make up a substantial part of Olde Cypress and vary in size, layout, construction era and level of updating.
Custom & Estate Homes
Larger residences and custom estates occupy another segment of the community, often with substantial outdoor living areas and golf, lake or preserve settings.
Olde Cypress was not built from one collection of homes.
Olde Cypress contains homes from multiple Southwest Florida builders rather than one community-wide floor-plan collection. That is another reason the individual residential section matters when comparing properties.
One of the best-documented later sections is Lantana at Olde Cypress, where Stock Development offered several collections of single-family home designs.
Stock Development floor plans.
Lantana included Stock Development's Topaz, Onyx and Sapphire home series. The documented plans ranged from smaller two-bedroom designs through larger three- and four-bedroom homes, with both two- and three-car garage configurations.
Original builder plans are useful for understanding a home's design, but they may not describe the property exactly as it exists today. Renovations, additions and owner modifications should be verified for the specific resale home.
Why two Olde Cypress homes can be priced very differently.
Villa-sized properties occupy a very different part of the market from larger custom estate homes. Even homes with similar square footage can have substantial differences in value depending on their condition, homesite and improvements.
Home & Condition
Living area, floor plan, construction era, renovation history, roof and mechanical updates all influence how a resale home should be compared.
Homesite & View
Golf-course frontage, lake views, preserve exposure, privacy and the orientation of the homesite can create meaningful differences between otherwise similar homes.
Outdoor Living
Pool design, lanai improvements, outdoor kitchens, garage capacity and other major improvements can also affect how buyers compare one property with another.
Olde Cypress homes currently for sale.
Current Olde Cypress listings may include everything from villa residences to larger custom homes, so look beyond price alone when comparing what's available.
Pay attention to the residential section, home size, condition, renovations, outdoor living and whether the property faces the golf course, a lake or preserve area.
Live listings below update as properties enter the market, change status or sell.
Olde Cypress
Olde Cypress has more than one layer of association.
Olde Cypress is organized differently from a community with one HOA governing every residential detail. The community includes a Master Property Owners Association along with nine individual Neighborhood Homeowners Associations.
The neighborhood associations govern matters within their respective residential sections, while the master association handles broader community responsibilities and common areas that are not assigned to an individual neighborhood association.
Master Association
The master association oversees broader community responsibilities and common infrastructure, including areas such as landscaping, streetlights, signage, paving and stormwater systems.
Nine Neighborhood HOAs
Olde Cypress contains nine neighborhood associations. The rules and responsibilities affecting a specific home can therefore depend on the residential section in which the property is located.
Architectural Review
Exterior modifications can involve both neighborhood and master-level review. Buyers planning exterior changes should review the current architectural requirements for the specific property.
That does not mean ownership is free of community-related expenses. Buyers still need to account for the applicable master and neighborhood association obligations as well as the resident club membership structure. Current fees, assessments and governing documents should be verified for the specific property before purchasing.
The club and the residential community are separate.
This is one of the most important things for an Olde Cypress buyer to understand. The Club at Olde Cypress and the residential associations are separate organizations. The golf club is not an asset of the residential master association.
Social membership is part of the ownership structure.
Olde Cypress homeowners become social members of The Club at Olde Cypress, providing access to the club's social amenities.
Buyers who want additional club privileges can select higher membership levels, including golf. Full golf membership is not automatically required simply because you own a home in Olde Cypress.
Part of living in Olde Cypress.
The resident social relationship provides access to club amenities and distinguishes Olde Cypress from a gated community with no private-club component.
Golf is optional.
Residents who want expanded privileges can consider additional membership levels up to full golf. Buyers should confirm current categories, availability, dues and membership terms directly with the club.
An 18-hole championship course designed by P.B. Dye.
Golf is a defining part of the Olde Cypress setting. The private 18-hole championship course was designed by P.B. Dye and incorporates lakes, sculpted bunkering and changes in elevation throughout the layout.
One of its best-known features is the 12th hole, a short par three with an island green.
Golf is central to the setting, but full golf membership is a choice.
Buyers can enjoy the atmosphere of an established golf community without automatically being required to hold the highest golf membership level. That distinction is one of the features that separates Olde Cypress from communities where golf membership is bundled with every residence.
There is more to Olde Cypress than golf.
The Club at Olde Cypress extends beyond the golf course. Residents have access to social and recreational amenities that include swimming, fitness and wellness, racquet sports, dining and member activities.
That distinction matters for buyers who like the setting and private-club atmosphere of a golf community but do not necessarily plan to make golf the center of their lifestyle.
Recreation, wellness and social life in one club setting.
The club provides residents with places to stay active, meet other members, dine and participate in organized activities throughout the year. Buyers should confirm current club access and membership privileges for the membership category they are considering.
How residents spend their time beyond the course.
Olde Cypress offers several ways to stay active without stepping onto the golf course. The club's recreational amenities include swimming, fitness and wellness, pickleball, tennis and bocce.
Swimming Pool
The club swimming pool gives residents another place to relax and enjoy the Southwest Florida climate away from the golf course.
Fitness & Wellness
Fitness and wellness facilities are part of the club amenity offering for residents who want an active lifestyle close to home.
Pickleball & Tennis
Both pickleball and tennis are available through the club, giving residents additional racquet-sport options beyond golf.
Bocce
Bocce adds another recreational and social option to the club's amenity mix and provides a more casual way for residents to spend time together.
Where is Olde Cypress?
Olde Cypress is in North Naples, east of Interstate 75 and north of Immokalee Road. Its location gives residents convenient access to the Immokalee Road commercial corridor while keeping the community itself centered around golf, lakes and preserve areas.
Access to I-75 also makes Olde Cypress practical for buyers who regularly travel throughout Naples or north toward other parts of Southwest Florida.
East of I-75 near the Immokalee Road corridor.
Olde Cypress offers an inland North Naples location with relatively direct access to major shopping, dining, healthcare and transportation corridors.
7165 Treeline Drive
Naples, FL 34119
North Naples conveniences are within reach.
Olde Cypress is positioned near several of the shopping, dining, recreation and transportation areas buyers commonly consider when choosing a North Naples community.
Immokalee Road
Shopping, restaurants, everyday services and access to the I-75 interchange.
Founders Square
A growing North Naples destination for restaurants, services and retail.
Mercato
Shopping, restaurants and entertainment in western North Naples.
Gulf Beaches
Vanderbilt Beach and other North Naples Gulf beaches are accessible from the community.
Seed to Table
Located along the Immokalee Road corridor with surrounding North Naples shopping.
Healthcare
North Naples medical and healthcare services are accessible from the community.
I-75
Interstate access provides connections throughout Naples and Southwest Florida.
RSW Airport
Southwest Florida International Airport is accessible north via the I-75 corridor.
Travel times vary with traffic, time of day and exact starting point. Use current mapping for route and drive-time information.
A few rules buyers should understand before purchasing.
Rental, pet, flood and insurance questions should be reviewed carefully for the specific Olde Cypress property. The community's multiple neighborhood associations make property-specific due diligence particularly important.
Rental Rules
Olde Cypress permits leasing, but rentals are regulated. The recorded master leasing amendment establishes a 60-day minimum lease term and limits an owner to no more than four leasehold interests for the same parcel during a calendar year.
Pet Rules
Olde Cypress governing documents contain pet provisions, but the individual neighborhood associations can add another layer of rules or restrictions.
Flood & Insurance
Flood-zone and insurance considerations should be evaluated property by property. One home's flood-zone, elevation or insurance situation should not be assumed to apply to another Olde Cypress property.
Not every Naples golf community works the same way.
Olde Cypress combines an established private-club setting with a membership structure that gives homeowners more flexibility than communities where full golf membership is bundled with every residence.
It also has an unusually broad range of housing for a community of approximately 550 residences, from attached villas through larger estate homes.
Golf Beyond Social Membership Is Optional
Homeowners have a resident social relationship with The Club at Olde Cypress, but buyers who do not want full golf membership are not required to select it.
The Club Is Separate
The golf club and residential associations are separate. The course is owned and managed independently rather than being an asset of the residential master association.
More Housing Variety
Multiple residential sections include attached villas, single-family residences and larger estate homes rather than one dominant home style or floor plan.
An Established Setting
Olde Cypress dates to 2000, with residences positioned around an established P.B. Dye golf course, lakes and mature residential areas.
Across Approximately 540 Acres
A relatively limited number of homes spread across a large community.
Approximately 550 residences occupy roughly 540 acres. That scale helps distinguish Olde Cypress from some of Naples' larger master-planned developments while still providing multiple residential sections and housing types.
Potential advantages and tradeoffs.
No community is the right fit for every buyer. These are some of the practical differences worth considering when comparing Olde Cypress with other Naples communities.
Why buyers may choose Olde Cypress.
Gated community access near the Immokalee Road and I-75 corridor.
Buyers can compare several housing types and residential sections instead of one repetitive product.
Buyers interested primarily in dining, fitness, racquet sports and social activities are not required to select the highest golf membership level.
The community combines mature residential areas with an established P.B. Dye golf course and club amenities.
What buyers should think through.
Olde Cypress is not the same as choosing a gated community with no private-club obligation.
Buyers need to review both the master association and the applicable neighborhood association documents.
Different construction periods, builders, renovations and neighborhoods can make similarly priced properties very different purchases.
Buyers prioritizing a marina, direct Gulf access or walk-to-beach living should compare a different group of Naples communities.
Is Olde Cypress the right fit for you?
Olde Cypress makes the most sense for buyers who want the setting and amenities of a private golf and country club community but still want choices in both housing and golf membership.
The biggest mistake is treating every Olde Cypress home as interchangeable. The residential section, association structure, condition of the home, homesite and club membership needs should all be considered together.
Those three pieces can make two Olde Cypress properties with similar prices very different choices for a buyer.
What is happening in the Olde Cypress real estate market?
Olde Cypress is a relatively small community, which means a limited number of sales can noticeably affect community-wide market statistics.
The mix of villas, single-family homes and larger estate properties also makes it important to look beyond a single average or median number when evaluating an individual property.
The numbers need context.
A community-wide statistic can include very different types of properties. A smaller villa and a renovated estate home may both be Olde Cypress sales, but they should not necessarily be used as direct comparisons when determining the value of a specific home.
What matters when comparing Olde Cypress sales.
Recent sales are useful, but the strongest comparison usually comes from properties that are similar in housing type, residential section, size, condition, homesite and major improvements.
Property Type
Villas, traditional single-family homes and larger estate properties occupy different parts of the Olde Cypress market. Start by comparing like with like.
Condition & Updates
Renovation level can materially change how buyers value two otherwise similar homes, particularly in an established community with different construction eras.
Homesite & Setting
Golf-course, lake and preserve settings, privacy, orientation and outdoor living can all influence how buyers compare competing properties.
Want the latest numbers?
The market statistics shown cover August 2025 through August 2026. For a more current market update, text or email George and we’ll send you the latest available statistics.
What else should you compare with Olde Cypress?
The best comparison depends on what matters most to you: golf membership, home style, community size, location, amenities or purchase price. These North Naples communities are useful places to start.
The Strand
Another North Naples private golf and country club community near the Immokalee Road and I-75 corridor. Its housing mix and golf structure differ from Olde Cypress, making it a useful comparison.
TwinEagles
A larger North Naples golf community farther east along the Immokalee Road corridor and worth comparing when golf itself is a major purchase priority.
Quail Creek
A North Naples private-club alternative for buyers comparing larger homes and a golf-oriented lifestyle.
Pelican Marsh
A gated North Naples community with a private golf-club component and convenient access to western North Naples.
The Quarry
Worth comparing for buyers who want gated North Naples living with golf while placing additional value on extensive water-oriented recreation.
Olde Cypress FAQs.
Quick answers to some of the questions buyers commonly have when researching Olde Cypress in Naples.
What is Olde Cypress in Naples?
Olde Cypress is a gated North Naples golf and country club community with approximately 550 residences across 540 acres surrounding an 18-hole P.B. Dye-designed golf course.
Is Olde Cypress gated?
Yes. Olde Cypress is a gated residential community. Buyers touring properties outside public open-house periods generally need authorized community access.
How many homes are in Olde Cypress?
Olde Cypress contains approximately 550 residences spread across roughly 540 acres.
When was Olde Cypress established?
Olde Cypress was established in 2000.
What types of homes are in Olde Cypress?
Housing includes attached villas and single-family residences, including larger estate homes. Home styles, sizes and construction periods vary among the community's residential sections.
Who designed the Olde Cypress golf course?
P.B. Dye designed the private 18-hole championship golf course at Olde Cypress.
Is golf membership mandatory at Olde Cypress?
Full golf membership is not mandatory. Homeowners become social members of The Club at Olde Cypress, while additional membership levels up to full golf are optional.
Does Olde Cypress have pickleball?
Yes. Pickleball is among the recreational amenities offered through The Club at Olde Cypress.
Does Olde Cypress have a CDD?
Current research indicates no Community Development District for Olde Cypress. Buyers should still verify current property-specific assessments and obligations before purchasing.
Can homes in Olde Cypress be rented?
Yes, subject to association restrictions. The recorded master leasing amendment establishes a 60-day minimum lease term and no more than four leasehold interests for the same parcel during a calendar year. Neighborhood-specific rules should also be reviewed.
What makes Olde Cypress different from other Naples golf communities?
Important differences include its approximately 550-residence, 540-acre layout, housing choices ranging from villas to estate homes, and its membership structure. Resident social membership is part of ownership while higher golf membership levels are optional, and the golf club is separate from the residential association.
Let's talk about Olde Cypress.
Whether you're considering buying a home in Olde Cypress or preparing to sell one, George can help you understand how the property fits within its individual neighborhood and the community as a whole.
From comparing recent sales and homesites to understanding club membership, housing styles and available properties, you'll get information specific to Olde Cypress and the home you're considering.
