Par 28

Level 3 playing from 854 - 1,661 yards

Longleaf is the furthest southern course in The Villages.  For now.  As more are built near Eastport and Middleton, that designation will end.  And who knows, based on the incredible southerly growth, someday Longleaf might be considered centrally located!  But for now, when you’re putting on #5, know you're on an executive green that's closer to Key West than anywhere else in The Villages!  And over 20 miles from Amberwood, the most northerly executive course.  Ok, enough of the geographic fun facts!  A better "bottom line" is that it's one of my top five courses in 2024!   


Longleaf has the most famous oak in The Villages - it'll vex you on 3 and mesmerize you on 8 (see the picture above).  Along the way you'll use five different clubs off the tees. But before you think about your drives, get to Longleaf early and take advantage of a huge practice green to focus on your short game.  The practice area is located behind the starter shack on the path to Loblolly.  You’ll have ample room to work on your chipping game.  Since all the executive courses have thin, difficult fringes, getting some practice on your short approach shots will certainly be helpful. 


With your short game polished up, let’s tee off!  Your first drive will be a tester.   It plays longer than it looks to an elevated green and into the usual prevailing wind.  The green’s severe downslope to the pond on the left requires your first shot of the day to land right of the pin to get a par.  #2 is shorter and easier - a respite before the storm!  Longleaf 3 is the signature hole – a beautiful long par four that bends to the right around a large pond.  But that’s not the challenging part – it’s the massive oak that drapes over the center of the fairway.  Driving past it from the golds requires a 230+ yard shot.  Anything shorter means you’ll be hitting under, around, over, or through it on your second shot.  If you can somehow manage to get on in two, getting a par will be easy work as the green is flat and fair.  But getting on in two is one of the hardest tasks in town - that’s why Longleaf 3 is included in my Hardest Holes List.  


#4 proves the point that short doesn’t equal easy.  This elevated green punishes any shot that doesn’t stick.  And it’s got a crazy roller coaster drop in the center, so depending on the pin placement this can be a three-putt candidate. #5 runs between a pond on the right and homes on the left to a backdrop of beautiful oaks.  The green has a subtle ridge along the middle making it a deceptively hard (and most southern) putt.  #6 doubles back to the north, so the wind you dealt with on 5 will be the opposite on 6.  A guy in a home near the tee box used to have a sign up offering to sell balls he fished out of the pond – I don’t see the sign anymore – but the gator is still there! Survival of the fittest?  Moving on, the 7th has something equally disturbing - a green that looks like it has a sinkhole in the middle. Which is more dangerous?  The gator on 6 or the crater on 7?   Tough question.  Here's something not tough at all - Longleaf 8 is one of the best-looking golf shots in The Villages!  For sure a Postcard!  And if you’re playing in the late afternoon, the sunset will accentuate that magnificent oak!  By the way - that perfect oak in the back of 8 that gets so much praise, is the same tree that gets all the complaints on #3, proving that everything is a matter of perspective!  And now you come to one of the most difficult finishing holes in The Villages.  Water along the left and in front of the green requires a precise shot to #9. Not easy to do at the end of a round.  Plus, you may have some onlookers watching from the starter shack for some added pressure.  So, embrace the pressure and let it rip. 

Bottom Line: Longleaf's worth the trek to the bottom of town!   

Toughest to Easiest:

3, 9, 7, 5, 1, 6, 4, 8, 2 – hardest green #4

From the blacks!   

The stress of playing from the black tees is that the angle of approach to the green requires more accuracy, or the shear extra length intensifies the challenge.  For Longleaf, the black tees that cause the most stress are #3, 7 & 9.  The oak on 3 makes this hard enough from the gold, adding 40 more yards just means your second shot will have a higher probability of dealing with that tree, making it nearly impossible to land in regulation (at least for me!).  #7 plays 190 which is super long for a par three.  And the 9th tee box is further left so you’ll need to carry more of the pond, and the landing zone on the elongated narrow green is tighter.  It’s worth the challenge but play Longleaf from gold first – you’ll probably find that’s hard enough!

Go Green!

Water?  What water!  I don’t see any water?  Not from the green tees.  You’ll still have to deal with that huge oak on 3, but the remainder of Longleaf averages just 77 yards.  You’ll especially appreciate that on the opening and closing holes. 

What’s nearby? 

Just a mile west of the Longleaf starter shack is the 18-hole Fenny Putt and Play course.  This is The Village’s original putting course that's been so popular three more elaborate versions have been built – two near Sawgrass Grove and one up north at the First Responder Rec Center.  It sits on an "island" and the only parking available is for golf carts.  If you’re lucky you might even see a game of croquet next door.  And on the drive from Longleaf to the Fenny Putt and Play, look for a very interesting combo – the Dudley Canine Park right next to an Archery Range.  Think about that and fill in your own punch line!  Especially if you’re a cat lover!

Longleaf Looking Good

That's the tree on 3!  

The green on 5 is your farthest point south in The Villages - for now.  

The 7th is really a hidden gem.  It's gorgeous and about 160 to the center with a really difficult green - it's got it all.

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.