Home with a tile roof, arched entry and circular paver drive under oaks at Olde Cypress, North Naples, Florida

Olde Cypress Homes & Real Estate

Olde Cypress, Naples FL

Search the newest Olde Cypress homes for sale & real estate below! Olde Cypress is a gated golf community of about 550 homes on 540 acres off Immokalee Road in North Naples, Florida, built around P.B. Dye’s first championship course in Collier County. A social membership at The Club at Olde Cypress comes with every home and is mandatory; golf is optional and capped. Nineteen homes sold between January and August 2026 at a median of $1,110,000, from $634,800 to $2,990,000.

Compare Olde Cypress with other communities in our Naples neighborhood guides.

Quick Facts

  • $1,110,000, 19 sales Median sold 2026
  • $634,800 to $2.99M Range
  • $477 Median price per sq ft
  • 20, median Days on market
  • Mandatory for every owner Social membership
  • Optional, capped at 350 Golf

Current Homes For Sale in Olde Cypress

Social Membership Is Mandatory, Golf Is Not

Every Olde Cypress owner belongs to the club, but only as a social member unless they choose to add golf. That structure decides the annual cost more than the house does.

Every owner is a social member
A social membership comes with the purchase of any home, and it carries the fitness center, tennis, pickleball, bocce, pools and the clubhouse dining rooms. Published figures put its annual dues near $5,975 with no initiation fee.
Golf is an upgrade, and limited
Full golf membership has been published at about $175,000 to join and $19,600 a year, with associate golf at roughly $35,000 and $9,100. Full golf is capped at 350 members, so availability is not guaranteed when you buy.
That suits buyers who do not play
In communities where golf membership is compulsory, a non-golfer pays for a course they never use. Here the mandatory element is the social membership, which is why Olde Cypress draws buyers who want a club without the golf commitment.
Ask what transfers with the house
Some resales come with a golf membership available at closing and some do not, and the difference is worth six figures. Confirm the category, the transfer terms and who pays the initiation before you agree a price.
Figures need checking
The membership numbers published online come from golf-community directories rather than the club, and clubs revise them. Ask the club for the current schedule for the category you want.

The Newer Enclaves Sell Fastest

Olde Cypress was built in stages over more than twenty years, and the market treats those stages very differently.

Lantana leads on both counts
The eight Lantana sales came in at a median of $1,495,000 and just 9 days on the market, the newest and quickest part of the community.
The original sections take longer
The six sales in the original Olde Cypress sections closed at a median of $1,052,500 after 42 days, at $438 per square foot against Lantana’s $546 for houses of a similar size.
Villas are the entry point
Santorini Villas sold at a median of $638,900 and $338 per square foot, the least expensive way into the community, though the two sales there took a median of 105 days.
Buyers negotiated modestly
Thirteen of the nineteen sales closed below the final asking price and one above it, at a median of 98% overall. The median marketing period across the community was 20 days.
Compare within the enclave
A Lantana house and an original Olde Cypress house of the same size are different products with different prices per foot. Match a listing to sales in its own neighborhood before looking at the community median.

Weighing Olde Cypress

Pros

  • Golf is optional, not compulsory
  • P.B. Dye championship course
  • About 550 homes on 540 acres
  • More than 200 acres of lakes and preserve

Cons

  • Social membership is mandatory for every owner
  • Full golf is capped at 350 members
  • Published club fees are directory figures; confirm them
  • No beach access included
Mercato at sunset with cinema, shops and patio dining, a short drive from Olde Cypress in North Naples, Florida

Olde Cypress Shopping and Dining

Shopping

  • Founders Square and Seed to Table minutes away
  • Shops along Immokalee Road
  • Mercato a short drive west
  • Nothing walkable outside the gate

Dining

  • Clubhouse dining rooms and lounges
  • Restaurants along Immokalee Road
  • Mercato and North Naples dining nearby
  • Seasonal reservations essential from January to April

Olde Cypress Club and Lifestyle

Beach

  • Gulf beaches a drive west
  • No beach access included with ownership
  • Lakes and preserve throughout the community
  • Golf carts used throughout

Lifestyle

  • 18-hole P.B. Dye championship course
  • Tennis, pickleball and bocce
  • Fitness center and resort pool
  • Clubhouse with several dining rooms

What to Know Before Buying in Olde Cypress

Olde Cypress is a gated golf community of about 550 homes on 540 acres, laid out around the first championship course P.B. Dye built in Collier County. More than 200 of those acres are lakes and preserve, and most homes look over one or the other.

Its distinguishing feature is the membership structure. Every owner joins the club socially, but golf is a separate decision, which makes it unusual among North Naples club communities.

What Does Olde Cypress Cost?

Nineteen homes in Olde Cypress sold between 8 January and 21 August 2026 at a median of $1,110,000, from $634,800 to $2,990,000. The median sale took 20 days, which is quick for a club community at this price.

The community-wide figure covers villas at about $640,000 and estate homes approaching $3 million, so the neighborhood matters more than the median.

Olde Cypress neighborhoods with closed sales, 8 January to 21 August 2026, highest median first. Source: Naples MLS, area NA21. One- and two-sale neighborhoods are indicative only. Sold to list compares the sale with the final asking price.
Neighborhood Sales Median sold Median size Per sq ft Days
Da Vinci Estates 1 $2,990,000 3,833 sq ft $780 —
Lantana 8 $1,495,000 2,731 sq ft $546 9
Terramar 2 $1,424,500 2,433 sq ft $580 50
Olde Cypress, original sections 6 $1,052,500 2,330 sq ft $438 42
Santorini Villas 2 $638,900 1,892 sq ft $338 105
All 19 $1,110,000 2,340 sq ft $477 20

Among nearby clubs, Quail Creek sells at a similar level and TwinEagles below it, while Talis Park and Mediterra sit well above.

Newer stages, faster sales

Lantana, the newest part of the community, accounted for eight of the nineteen sales and moved in a median of 9 days at $1,495,000. The original sections sold for $1,052,500 after 42 days.

Some of that gap is age and specification rather than address: newer houses need less work, and buyers pay for that. Compare a listing with sales in its own neighborhood and of its own vintage before reading anything into the difference.

What membership costs

Published membership figures for The Club at Olde Cypress, compiled September 2026 from golf-community directories rather than the club itself. Clubs revise fees, so confirm the current schedule with the club before making an offer.
Category Initiation Annual dues Who it is for
Social None published About $5,975 Every owner; mandatory
Associate golf About $35,000 About $9,100 Limited golf access
Full golf About $175,000 About $19,600 Unlimited play; capped at 350 members

The mandatory element is the social membership, which every owner pays whether or not they play golf. For a buyer who does not play, that is the whole club cost, and it is a fraction of what a compulsory golf community would charge.

For a golfer, the question is availability as much as price. Full golf is capped at 350 members, so ask where the category stands and whether a membership can transfer with the house you are considering.

Where is Olde Cypress?

Olde Cypress sits off Immokalee Road east of I-75, with the club at 7165 Treeline Drive. The course and its lakes run through the middle of the community, and the preserve areas form much of its boundary.

Founders Square, Seed to Table and the shops along Immokalee Road are a few minutes west, and I-75 is closer still. The Gulf beaches are a drive west.

Oakes Estates, the acreage neighborhood nearby off Immokalee Road, and Mediterra, further west on Livingston Road, are the nearest communities we cover.

Olde Cypress neighborhood boundary. Base map and boundary data from Google.

Additional Olde Cypress Information

Olde Cypress suits a buyer who wants a private club, a well-regarded course and a gated North Naples address without a compulsory golf membership. Its villas also make it one of the more accessible club communities in this part of Naples.

It is the wrong choice if you want beach access or a community without any club obligation. For a club where golf is compulsory, compare Grey Oaks or Collier’s Reserve; for optional membership on a larger scale, Pelican Marsh or Kensington; for acreage nearby with no club at all, Oakes Estates.

Further east along Immokalee Road, TwinEagles offers 36 holes with a membership deeded to every home, and Quail Creek offers two courses with membership left optional.

Closer to the city, Wyndemere offers 27 holes but requires every owner to buy into the club.

Browse the wider market through Naples homes for sale, Naples golf course homes and Naples gated communities, or see every community in the Naples neighborhood guides. Its villas also sit within the market for Naples condos for sale and Naples golf course condos. Owners weighing a sale should start with a Naples home value estimate, and school zoning is covered in our guide to Collier County schools.

Early light across a putting green, the kind of morning round enjoyed in Olde Cypress, Naples, Florida

Olde Cypress, Low and Quiet

A mature, low-density golf community off Immokalee Road. We’ll set its homes, coach homes and villas side by side.

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Olde Cypress Schools

Collier County Public Schools serves Olde Cypress. The schools below are the assignment returned for a representative address in the neighborhood.

Assignment runs by parcel, not by neighborhood. Two houses on the same street can be zoned differently, and the district redraws boundaries from time to time. Check the specific address before relying on it.

Olde Cypress is zoned for Laurel Oak Elementary, Oakridge Middle and Aubrey Rogers High, confirmed on the county locator for 7165 Treeline Drive. A Lantana address returned no result on the locator and is assumed to match, so confirm the specific address before relying on it.

Private school distances are straight-line approximations from the neighborhood, offered for orientation rather than as a recommendation.

The district states that its maps provide general information and that accuracy is not guaranteed, nor should a result be taken as a guarantee of placement. Look up any address on the CCPS attendance zone locator, or call the Department of Student Assignment on (239) 377-0540.

Zoned schools for a representative address, verified September 2026. Source: Collier County Public Schools.
ElementaryLaurel Oak Elementary
MiddleOakridge Middle
HighAubrey Rogers High
DistrictCollier County Public Schools
Nearby private schools
NearestRoyal Palm Academy (~4.5 mi)
Also nearbyCommunity School of Naples (~6.0 mi)

Olde Cypress FAQs

Where is Olde Cypress in Naples?

Olde Cypress is in North Naples, Florida, in the 34119 ZIP code, off Immokalee Road east of I-75, with the club at 7165 Treeline Drive. The community covers about 540 acres, more than 200 of them lakes and preserve, and sits within a short drive of Founders Square and the shops along Immokalee Road.

Is club membership mandatory at Olde Cypress?

A social membership is mandatory and comes with every home; golf membership is optional. The social membership covers the clubhouse, dining, fitness center, tennis, pickleball and pools. Full and associate golf memberships are available separately, and full golf is capped at 350 members.

What does golf cost at Olde Cypress?

Published figures put full golf at about $175,000 to join with annual dues near $19,600, and associate golf at roughly $35,000 with dues near $9,100. Social dues are about $5,975 a year with no initiation. These come from golf-community directories rather than the club, so confirm the current schedule directly.

What do homes cost in Olde Cypress?

Nineteen homes sold between January and August 2026 at a median of $1,110,000, with the middle half between $900,000 and $1,657,500 and a full range from $634,800 to $2,990,000. Lantana homes sold at a median of $1,495,000, the original sections at $1,052,500 and Santorini Villas at $638,900.

Who designed the Olde Cypress golf course?

P.B. Dye, whose 18-hole championship course here was his first in Collier County and opened around 2000. It runs about 6,711 yards and shows the family traits: elevation changes, sculpted bunkering and elevated greens. The community was developed by Stock Development around it.

What neighborhoods are in Olde Cypress?

About ten, mixing single-family homes and villas: Lantana, Da Vinci Estates, Terramar, Santorini Villas, Egret Cove, Ibis Landing, Santa Rosa, Vita Tuscana, Biscayne Place, Strata Bella and Wild Orchid among them. They were built in stages from 2000 onward, which is why prices and pace differ across the community.

Naples Neighborhoods

Considering Olde Cypress?

Social membership is mandatory and golf is optional, and whether a membership transfers with the house is worth six figures. We can tell you what a listing really costs to own.

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