Oakleigh
Par 28 - Level 3 - 82 Slope Rating
Plays from 1,005 – 1,517 yards
Some say Oakleigh is the ugly stepsister to its neighboring Amberwood. Harsh? Maybe. But the two sister course will always draw comparisons. Oakleigh lacks Amberwood’s heavenly glow and storybook charm, but it make up for it with a little “step-mother” attitude.
Fairy tales aside, Oakleigh makes you earn whatever magic you find. So let’s skip the prologue and head to the first tee.
The opener eases you in with a welcoming look and a green that slopes gently forward. Leave your approach short and you’ll be rewarded with an uphill putt - an encouraging start before the spell wears thin. That happens quickly at Oakleigh’s 2nd hole, the first true wicked-stepmother test. An expanse of sand guards the entire front of the green, and anything less than a perfectly floated drop shot risks turning your scorecard into a pumpkin.
The 3rd hole is short - very short - but don’t let its length fool you. The rolling green makes it deceptively tricky, and a mischievous cup placement can turn an 80-yard wedge into an ego-bruising bogey. Few things in golf feel more “cruella” than registering a four on a hole that short.
The 4th and 5th holes circle a pond as you make the turn, and the 5th is Oakleigh at its best. It’s easily the most picturesque hole on the course - and the most punishing. The green is the toughest you’ll face all day. Try to land on the left side if you want to avoid three-putt misery.
The 6th is a straightforward par four that rewards accuracy off the tee to avoid fairway sand. At just 250 yards, the unprotected green offers your best chance at birdie if you’re willing to be aggressive. The 7th brings another short wedge shot, but not much else. And the 8th features a right-side trap that seems to hold a very personal grudge against me.
Then, as the clock creeps toward midnight, Oakleigh unveils its final test. The 9th plays 181 yards uphill to a long, narrow green, flanked by bunkers both front and back. It’s not just the toughest hole on the course - it’s one of the hardest in town. There’s no fairy godmother here, no last-second rescue. You either execute, or you don’t. Talk about saving the best for last.
So, after a round at Oakleigh, how does the “ugly stepsister” label feel when held up against Amberwood’s Cinderella reputation? Too Grimm? Or is Amberwood’s glass-slipper status a little generous? The truth, as always, takes more than one dance to uncover. Play them both a few times - and then decide for yourself if the shoe really fits.
Toughest to Easiest:
9, 2, 4, 5, 6, 3, 8, 7, 1 – toughest green 5
From the blacks!
Oakleigh should be played from the black tees – period. You may even use 7 different clubs off the box. #9 is already the hardest hole on the course, but from blacks it’s over 200 – wow! And three of the shortest holes, #3, 6 & 7, play like regular par threes from the back tees. #2 requires your most precise shot to hit over the trap onto the narrow green. And #5 plays from a fun new angle shooting over water to land onto Oakleigh’s most difficult green. From the black tees, Oakleigh is certainly striking midnight at the ball!
Go Green!
All but two holes play really short from the green tees. Just the par four 6th and the closing par three 9th hole are still pretty long. You’ll also like that the angle to the green is more advantageous around the pond on #4 & 5. In fact, you may just find the whole course a bit more Charming from the greens!
What’s nearby?
The First Responder Recreation Center is just a mile north of Oakleigh. It’s one of the newest rec centers in The Villages complete with a huge pool, lawn croquet and all the standard outdoor amenities and games. But the reasons it’s worth every foot of the one mile to get there are these three things: 1) a new 18 hole putting course – the Stars and Stripes; 2) the largest game room in The Villages including darts, ping-pong, pop-a-shot, table shuffleboard and hundreds of familiar video games; 3) most importantly, an amazing collection of memorabilia from all branches of First Responders presented in a patriotic theme. Check this video out: First Responders Recreation Center. You better go after you play Oakleigh or my guess is you’ll get so immersed you’ll miss your tee time. It’s that worth it – as is every First Responder in our nation!
I’ve had more complaints about this story than any other - clearly my Grimm take on Oakleigh struck a nerve. A few readers have even suggested I take a bite of my own apple. Maybe I am the Big Bad Wolf in this tale. But that’s the thing about opinions: they’re rarely anyone else’s. So, I’ll keep playing Oakleigh, stay open to persuasion, and see if this story continues to soften with every round. After all, not every fairy tale reveals its happy ending on the first reading.
My impressions are based on playing from the Gold tee boxes. The Black and the Green tee boxes pose different challenges or benefits described as well. The rankings of the toughest to easiest holes are just my opinions - yours will be far different, as will your favorite courses and most difficult and attractive holes. I welcome your opinions or thoughts on any of this - click to leave a comment.
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