Experience the course like never before with our Flyover feature. Get a bird's-eye view of each hole, helping you strategize your round and navigate the course with precision.
Plan your shots effectively with our Yardage Maps. Click on the yardage maps for detailed measurements on every hole, including distances to hazards and key landmarks, ensuring you make the right decisions on every swing.
Back in 1974 when award-winning golf course designer Ron Garl built Cypresswood Country Club in Winter Haven, FL, not too far from his hometown of Lakeland, it was the talk of the town. Golfers from all over Florida would converge on the course to see what it was all about and during the winter months, tee times were at a premium. The course has always been in good shape and didn’t require anything other than routine maintenance with no major changes other than a greens renovation in 2000. That was until last year when Operator Bob Schade - who started working at Cypresswood as a golf cart attendant in 1986 and has been a mainstay ever since – and the board of directors of the Community Association decided to give the course a makeover in 2017. They started with an all-new irrigation system in 2018 and then a major facelift in the summer of 2020.Sadler Site Work was chosen as the contractor and did all of the construction. Schade and his team spent a lot of time on the shaping of the greens to make Cypresswood the most golfer friendly course in the area. Ron Garl would occasionally show up at the course and give Schade and his team some advice and suggestions. The pandemic that started last spring enabled them to get a lot of work done in a much shorter period of time since there was little to no play on the golf course. Nevertheless, operations were shut down in May. All 18 greens were rebuilt and replanted with TifEagle grass, tee boxes were laser leveled, and bunkers were expanded and flattened; everything geared toward making the course a lot more player-friendly. The focus of this redesign is clear: Hit the shot that the architect intended. In November of 2020, Cypresswood Country Club had its grand reopening. In comparing the course then and now, it is night and day; the course is a lot greener and although the fairways are still growing, it’s a lot plusher than before. If you’ve played here before, you’ve probably noticed some of the changes, like the coquina-shelled parking area left of the greenside bunker on #8 and the pathway that goes through it. Number 12 has a completely new look from the White and Gold Tee boxes. The fairway bunker on the right has been greatly enlarged and should come into play more often especially for those trying to cut the corner of this dogleg right par 4. The fairway bunker on the left side was also enlarged. To me, 17 and 18 are still two holes that can make or break your round. Number 17 is a slight dogleg left par 4 that plays 376 yards from the White tees. Push your tee shot too far right and you can easily find the road, there are fairway bunkers on either side that come into play more often than not. A good drive will leave a short iron or wedge into an elevated green that features a lot of undulation and is well protected by bunkers.Number 18 is also a dogleg left that plays 402 yards. Hit your drive too far or push it right and you can easily find the water; the fairway bunker on the left has been known to ruin some good scores too. Hit your drive out over the bunkers and you’ll be left with an approach shot of about 150 yards into a relatively flat, long narrow green that is protected with bunkers on either side. The slope that was in the middle of the 18th green was flattened to create more pin placements. Number 3 has always been one of my favorite holes. This dogleg right par 5 plays 531 yards from the White tees. Water can come into play on the right side off the tee. Trees line both sides of the fairway off the tee and on your layup shot, so hit something you can control. Your approach shot is into a relatively flat, slightly elevated green that falls off on the left side There’s a lot of mounding around the green and a large bunker on the right.After your round, stop by the Cypresswood Pub. They have all of your favorite adult beverages including ice-cold draft beer, house wines, and mixed drinks, and some of the best clubhouse food in the area. The menu is pretty basic but let me tell you, they have some of the best chicken wings I have ever had and their burgers are second to none. It’s no wonder golfers and non-golfers alike can be found at the Pub for lunch and dinner enjoying some great food!.Membership at Cypresswood is easy and affordable. There’s no initiation fee – which is surprising with all the money that has recently been put into the facility – and you don’t have to live within this gated community. Best of all, there aren’t a lot of choices, no social memberships, junior memberships out-of-state memberships, or senior memberships to choose from; you’re either a resident of the community or you’re not. Non-residents pay a flat fee of $300 per month for an individual ($450 for a family). Residents pay $250/$375. For that, you’ll receive unlimited cart fees, greens fees, and range balls. Plus you can make tee times up to 14 days in advance. If you prefer to use your own cart, you can do that without an added trail fee; just show proof of liability insurance. That’s it. No food and beverage minimum – although the food is terrific – no pro shop minimum, etc. It’s the best membership value in Central Florida! There have been a lot of improvements to the golf course and the clubhouse at Cypresswood. The pro shop has a good selection of logoed golf apparel and equipment from PUMA and Cobra as well as several upcoming Cobra Demo Days on the range. And, as always, Bob Schade is available to help fix your swing or answer any questions you may have about the club.