A lot of sailors find the Upper Keys Sailing Club on a visit. They race a regatta, take a lesson, or bring a kid to a youth clinic. Then they join. Then they start looking at houses. If that sounds like where you are, this post is for you.
Sunset over the Upper Keys Sailing Club main dock on Buttonwood Sound. Photo by Jim Signor.
The closest homes are in Buttonwood Shores, Point Pleasant, and Lazy Lagoon. The Sanctuary is the nearest condo, and Islamorada adds more options a few minutes south. Below, I walk through each one in Key Largo and beyond, from the perspective of someone who has been a member for almost 50 years.
A Member Since 1978
My family joined the Upper Keys Sailing Club in 1978, when I was a kid. I watched the clubhouse become a sailing club, and once the pilings were set, I watched club members build the original main dock themselves. That dock still holds the majority of the club’s boat slips today.
I have sailed, and mostly raced, on Buttonwood Sound for nearly 50 years. I started out finishing last in every race of the Portsmouth series, the club’s handicap racing for small boats. Fast forward to today: I recently won the Force 5 Midwinter Championship as I approached my 60s.
My wife and I racing our Flying Scot on Buttonwood Sound.
Racing fleets come and go. Over the years I was very active in the Sunfish and Flying Scot fleets. The club no longer has a Flying Scot fleet, but my wife and I still race the yearly Flying Scot Florida District series, which wraps up each year at the Upper Keys Sailing Club. She and I host that final event.
All those years on the water shaped how I sell real estate here. I have been helping buyers find homes in the Florida Keys since 1988. Many of them first fell for the Keys from the deck of a sailboat, and many still keep their primary home elsewhere in South Florida. When a new member asks me where to live near the club, I answer as a sailor first and a Realtor second.
Where Is the Upper Keys Sailing Club?
The Upper Keys Sailing Club sits at 100 Ocean Bay Drive, near mile marker 99.5 on the bayside of Key Largo. It fronts Buttonwood Sound, one of the best small-boat sailing venues in the Keys.
The club was founded in 1973 and bought its Ocean Bay Drive property a few years later, which is why the clubhouse conversion and the main dock came after. Today it runs a full calendar of club racing, with small boats racing under the Portsmouth handicap and larger boats under PHRF (Performance Handicap Racing Fleet). It also hosts major events like the Force Five Midwinter Championship and the Buccaneer Blast Youth Championship, and it is just as much home to cruisers and daysailors. Members keep their sailboats in the club’s slips and dry storage, and boats drawing up to 5 feet tie up at the outer end of the main dock.
Families should know about the Mark Sorensen Youth Sailing Program, which serves kids ages 8 to 18. It began in 2006 with one generous donation and nothing else: no boats, no kids. I was its first youth sailing director. Today it has its own fleet and a new generation of Keys sailors coming up through it.
Neighborhoods Right Next to the Club
Three neighborhoods border the club directly. Buttonwood Shores and Point Pleasant offer a mix of bayfront and non-waterfront homes, and Lazy Lagoon is all non-waterfront, sitting a bit closer to US-1. From any of them, the club is a short walk or bike ride away, whether you head out to race, cruise, or just go for a sail.
These are small neighborhoods, so the inventory of homes for sale can be limited at times. The listing feed on each neighborhood page is live and changes as the market does.
The Club Membership Advantage
Here is the math most sailors miss. With your sailboat in a club slip or dry storage, when space is available, you do not need a waterfront home to sail every week. A non-waterfront home in Buttonwood Shores, Point Pleasant, or Lazy Lagoon, paired with a club membership, can save hundreds of thousands of dollars compared to buying on the water.
Condos Near the Upper Keys Sailing Club
The closest condominium to the club is The Sanctuary. It is a low-density community with a pool, tennis, and dry boat storage with launch service, and it puts condo living a short drive from the club. Inventory there can also be limited at times, and its page shows whatever is on the market right now.
If you want more options, browse all Key Largo condos and townhouses for sale or all Islamorada condos and townhouses for sale. Both pages update from the MLS with current listings.
Buccaneer Point: A Notable Bayside Option
A short drive south, Buccaneer Point sits near mile marker 98. It offers bayfront and lakefront homes on two saltwater lakes, and it is one of the more sought-after bayside neighborhoods in Key Largo for sailors who want a waterfront home near the club.
To see everything currently on the market, browse all Key Largo homes for sale.
Prefer the Ocean Side?
Some sailors also want quick access to the Atlantic and the reef. If that is you, visit our Key Largo oceanside homes page for links to those neighborhoods. The club is still only a few minutes away by car.
If you plan to move a sailboat between the bay and the ocean, know the routes. Sailboats pass through Angelfish Creek to the north or Snake Creek, with its drawbridge, to the south. Adams Waterway connects the two sides in Key Largo, but its fixed bridge keeps standing sailboat masts out.
Living in Islamorada and Sailing at the Club
You do not have to live in Key Largo to be an active member. Islamorada starts a short drive south on the Overseas Highway, and members live in both communities.
Islamorada suits sailors who want a little more distance from the mainland and can still be on Buttonwood Sound in minutes. Browse all Islamorada homes for sale to see what is available.
What Sailors Should Look For in a Keys Home
Buying near the club is different from buying a typical waterfront home. A few things to think through:
- Where the boat will live. If it lives at the club, your home may not need a dock at all, which opens up more neighborhoods.
- Club space and terms. Slip and storage availability depends on the club, so confirm it with them before buying a home that counts on it.
- Room for a trailer and gear. Small-boat sailors often need space for a boat, a trailer, sails, and spars.
- Hurricane plans for both the house and the boat. Ask how the home and the vessel are protected before you buy.
Draft Is the Number That Matters
Compared to many boating destinations, the Florida Keys are shallow-draft waters. If you plan to keep a keelboat or a larger powerboat at home, draft is the single most important measurement in your search.
The critical spot is usually not the canal itself. It is the opening where the canal meets open water. Many Keys canals were dug out, with the fill used to raise the surrounding lots, so the canal often runs much deeper than the entrance that connects it to the bay or ocean.
On the ocean side, the tide adds another variable. A canal entrance that works at high tide may not at low tide, so timing matters when you measure and when you plan to come and go.
Here in the Upper Keys, checking draft is part of how I help buyers during the inspection period. When a buyer needs a real number, we go out by boat and stick a pole in the water at the canal opening to measure it. For a buyer with a deep-draft boat, there is no better first look than seeing it firsthand.
Frequently Asked Questions
Where is the Upper Keys Sailing Club located?
The Upper Keys Sailing Club is at 100 Ocean Bay Drive in Key Largo, near mile marker 99.5 on the bayside, on Buttonwood Sound. It was founded in 1973 and operates as a nonprofit club.
What neighborhoods are closest to the Upper Keys Sailing Club?
Buttonwood Shores, Lazy Lagoon, and Point Pleasant sit immediately next to the club. Buttonwood Shores and Point Pleasant offer a mix of bayfront and non-waterfront homes, while Lazy Lagoon is non-waterfront. The Sanctuary is the closest condominium.
How deep are canal entrances in the Upper Keys?
Most canal entrances in the Upper Keys carry about 4 to 5 feet of water, though some are shallower and some are deeper. The entrance is usually shallower than the canal itself, and on the ocean side the tide also changes the usable depth, so each property should be measured before purchase.
Can I live in Islamorada and still be active at the Upper Keys Sailing Club?
Yes. Islamorada begins a short drive south of the club on the Overseas Highway, and club members commonly live in both Key Largo and Islamorada.
Does the Upper Keys Sailing Club have a youth sailing program?
Yes. The Mark Sorensen Youth Sailing Program at the club serves children ages 8 to 18 and offers sailing instruction close to the surrounding neighborhoods.
Talk to a Realtor Who Knows the Water
Any agent can pull up listings near the club. Knowing which neighborhoods suit a sailor’s routine, and which canal entrances suit your boat, comes from decades on the water.
I can help you compare homes and condos based on your boat and how you sail. Call me at 305-394-4449 or email [email protected]. You can also start with my Florida Keys home buying page.
Need financing? I am also a licensed mortgage loan originator (NMLS #2773431) with LoKation Mortgage (NMLS #2682974). Visit KeysLender.com to learn more.
Jim Signor - Florida Keys Real Estate, Broker-Associate, LoKation Real Estate