Countryside Golf & Country Club

Countryside Golf & Country Club gathers 1,133 homes behind one gate in Naples, east of Santa Barbara Boulevard between Davis Boulevard and Radio Road, in unincorporated Collier County. 912 are condominiums and 221 are single-family houses, all of them built between 1987 and 1992. It's finished: no developer, nothing new.

Before the floor plan, before the lanai, settle one thing. You don't pick a membership at Countryside. The home picks it for you. The club calls the place a "bundled community" and spells out the consequence: "your membership type depends on which of our 1,133 properties you choose to purchase."

Is the golf membership attached to the home or to the buyer?

Mostly to the home: the master declaration attaches full golfing privileges to 750 named lots and units, as an appurtenance that moves only with the deed of that home. The club counts 850 golf memberships and 283 social across the 1,133 homes. The other 100 golfing rights sit elsewhere, as personal Certificates held by social members: "Certificates are not appurtenant to the holder's Unit." So 850 golf memberships is not 850 golf homes. And a social home can't be upgraded by the person who buys it, so settle the grade first.

What does a social membership get you?

All of the club except the course. A social membership takes in the wellness center, the pool and courts, the clubhouse and the club's events. The declaration lets a social member use the course "only on a space-available basis", and says they "shall be assessed a reasonable fee for playing golf". Year-round access belongs to the homes carrying full golfing privileges, and what that leaves in a given season is a question for the club.

Can a social home be hit with a golf assessment?

No, and that is money rather than tee times. Assessments for "a capital improvement relating solely to the golf course" must be "approved only by two-thirds (2/3) of the Members having full golfing privileges, and shall be made solely against Members having full golfing privileges". Work on anything else needs two-thirds of both grades and is charged to every home.

What does a buyer owe at closing?

A capital contribution falls to the buyer at closing, above the agreed price. The declaration makes a resale capital contribution "due and payable to the Association by the transferee upon Conveyance of a Lot or Unit". Transferee means the buyer, and it's their own liability rather than the seller's to trade away, with a lien securing it against the home. The money goes into a fund for common-property improvements, and the board resets the figure each year, so get the number before writing an offer. An estoppel fee and any unspent food minimum come from the buyer too.

Who sends the bills?

Two bodies, for every home. Countryside Master Association, Inc. does business as Countryside Golf & Country Club: one corporation, not an association with a club bolted on. It owns the course, the clubhouse and the recreational property, and bills for those plus the roads, the street lighting and the drainage. Ownership is the only qualification for membership, with no opt-out.

The second bill comes from your neighborhood, one of 34 associations inside the gate. "Most associations have a quarterly condo fee which covers costs specific to that association; therefore, fees vary from neighborhood to neighborhood." Owners also covenant to spend a minimum at the clubhouse on food and drink, and the association can lien a home for that.

What do homes here cost?

Two markets behind one gate. Condominiums have sold from the $200,000s up to around $530,000, houses from the $470,000s up to around $880,000. Inside the condominiums the split runs again: the larger units in Country Hollow have changed hands for roughly double what Country Glen has, on the same master assessment. Condominiums measure about 950 square feet at the smallest, about 1,450 at the largest; houses run between about 1,700 and about 3,300.

The condominium buildings date from 1987 to 1992, and Florida holds buildings that old to a structural inspection and to reserves funded for what it finds. What a building's inspection found, and how its association has paid for the repairs, decides whether the fee holds or a special assessment lands, so ask for that report.

What is at the club?

An 18-hole, par 70 course, designed by Arthur Hills and redesigned by Kipp Schulties in 2019. A cart barn, pro shop and driving range sit beside it, with a pool, deck and spa, four courts for tennis, four for pickleball and two for bocce. The clubhouse was rebuilt in a renovation finished at the start of 2026. The wellness center is its own 6,500-square-foot building, open seven days a week from 5am to 10pm.

What are the rules?

• Pets. Cats, dogs and other household pets, not kept for commercial purposes and leashed outside the home. Neighborhood associations add their own terms.
• Exterior work. Nothing changes outside a home without written approval, repainting included. Fences need the board. No drones.
• Selling. One on-premises sign, four square feet at most, in or on a window.

Title work calls the place something else. Countryside's plats are recorded as Countryside at Berkshire Lakes, Sections One through Four, because the land sits inside the larger Berkshire Lakes master plan. The community called Berkshire Lakes is a different place with its own association.