What Is Cypress Woods Golf & Country Club?

Cypress Woods Golf & Country Club is a gated bundled golf community in North Naples offering a range of residential product types — condominiums, coach homes, villas, and single-family homes — centered on an 18-hole championship golf course designed by Gordon Lewis. Golf membership is bundled with every home purchase: no initiation fee, no separate annual golf dues, no tiered membership structure. Every resident plays from day one.

Cypress Woods occupies a distinct position in the North Naples market. It is not the most expensive or most prestigious golf community in the area — Grey Oaks and Tiburon serve that tier — nor is it the cheapest. What Cypress Woods consistently delivers is a genuine, warm community atmosphere that many buyers find more appealing than larger or more exclusive golf communities where residents may feel anonymous. The friendliness and approachability of Cypress Woods is a recurring theme in buyer feedback, and it reflects the bundled golf structure's social effect: when everyone plays and everyone participates, a cohesive community culture forms naturally.

The North Naples location is one of the community's strongest assets. Cypress Woods sits in the established North Naples corridor with fast access to Mercato, Waterside Shops, top-rated healthcare at NCH North Naples Hospital, multiple grocery options, and I-75 access for travel to RSW Airport and Fort Myers. Naples' Gulf beaches are approximately 15–20 minutes west — the standard drive time for most North Naples golf communities. Buyers who want to be within a 5-minute walk of the beach will not find that at Cypress Woods, but buyers who want the full North Naples lifestyle infrastructure package around a bundled golf community will.

Cypress Woods Location and Drive Times

Cypress Woods is located in North Naples off Vanderbilt Beach Road, one of the most well-developed residential corridors in Collier County. The Vanderbilt Beach Road corridor gives residents efficient east-west access — east to I-75 and west toward the Gulf — while the broader North Naples area provides the commercial and medical infrastructure that full-time and seasonal residents both depend on.

The North Naples location distinguishes Cypress Woods from East Naples bundled golf communities like Cedar Hammock and Forest Glen, which are positioned further from the core commercial and medical services that North Naples offers. For buyers who want to be close to the Ritz-Carlton Tiburón, Mercato's restaurant scene, NCH North Naples Hospital, and the Vanderbilt Beach corridor while living in a bundled golf community, Cypress Woods is one of the few options in that specific geographic position.

Collier County's A-rated schools serve the Cypress Woods area — Pelican Marsh Elementary, North Naples Middle School, and Barron Collier High School. This school access adds a family buyer segment to the community that East Naples bundled golf communities do not attract as strongly.

Cypress Woods Home Types and Price Ranges

Cypress Woods offers the broadest range of residential product types of the North Naples bundled golf communities — condominiums, coach homes, villas, and single-family homes all exist within the community. This variety means the same bundled golf membership and amenity campus is accessible to buyers at multiple price points, from a condo entry in the $300K range to a larger single-family home approaching $800K.

Condominiums are the most popular product type with seasonal residents and snowbirds who want a lock-and-leave property. Many condo units have screened lanais with golf course or lake views — delivering the visual benefit of the course even for buyers who may not golf every day. Coach homes appeal to buyers who want garage parking and more square footage while retaining the exterior maintenance coverage of a condo sub-association. Villas and single-family homes attract year-round residents and buyers who want private outdoor space, a pool, or maximum interior square footage.

The community is fully built out — all purchases are resale. This means buyers benefit from mature landscaping, a known community culture, and pricing that reflects actual market conditions. It also means every unit can be physically inspected rather than purchased off a plan. The Mediterranean and contemporary Florida architectural vocabulary — stucco exteriors, tile roofs, screened lanais, indoor-outdoor flow — is consistent throughout the community and maintains architectural harmony across property types.

Cypress Woods HOA Fees and What They Cover

HOA fees at Cypress Woods run between approximately $400 and $700 per month depending on the home type and sub-association. Condo and coach home units carry higher fees than single-family homes because the sub-association covers exterior building maintenance, roof reserves, and building insurance in addition to the amenity access that all home types receive. Single-family homeowners pay lower HOA fees but are responsible for their own lawn care, exterior maintenance, and individual homeowner's insurance policy.

The critical distinction — and the key financial advantage of Cypress Woods — is that golf is bundled into the HOA cost. There is no separate initiation fee and no annual golf membership dues paid outside of the standard HOA. Every homeowner, regardless of product type, has full access to the Gordon Lewis 18-hole championship course from the first day of ownership. When you compare this to optional-golf communities where a membership initiation costs $20,000–$75,000+ and annual dues add $8,000–$15,000/yr, the bundled model provides a clear cost advantage for buyers who plan to golf regularly during their ownership period.

There is no CDD assessment at Cypress Woods — a meaningful cost advantage over some North Naples communities where Community Development Districts add $1,500–$3,000/yr to the tax bill. Property taxes, homeowner's insurance, and flood insurance are separate from HOA fees. Buyers should verify the specific flood zone designation for any parcel before purchase, as this affects insurance cost significantly.

Golf, Clubhouse, and Resort Amenities at Cypress Woods

The Gordon Lewis-designed 18-hole championship course is the centerpiece of Cypress Woods, and its character reflects the community's overall personality — challenging enough to engage experienced golfers, approachable enough not to intimidate recreational players. Lewis is a respected Southwest Florida course designer, and the Cypress Woods course is considered one of the stronger bundled golf courses in the North Naples area, with fairways that wind through the community's lakes, preserves, and residential neighborhoods in a way that creates a visually rich playing experience.

The practice facility supports the playing experience year-round: a driving range, putting green, chipping area, and PGA-credentialed instruction program are all available. Organized leagues for men, women, and couples run throughout season (November–April) and maintain activity on the course year-round. For seasonal residents who arrive in January, there is a ready-made golf community and organized schedule from the first week.

The clubhouse at Cypress Woods is the social center of the community and a genuine gathering place. Casual and more formal dining options operate through season, with themed dinners, wine events, live entertainment, and charity fundraisers anchoring the social calendar. The resort-style pool, spa, fitness center, tennis, and pickleball courts serve the non-golf resident population and complement the golf lifestyle. Walking and biking paths through the preserve corridors add a nature-connected daily activity option that many residents use year-round.

Who Buys in Cypress Woods?

Cypress Woods vs. Comparable Naples Bundled Golf Communities

Buyers considering Cypress Woods typically evaluate it alongside other bundled golf options in Collier and Lee counties. The key differentiators are location, number of holes, fee structure, and community scale.

Pros and Cons of Cypress Woods Naples

Cypress Woods Naples — Buyer Q&A