A Tongue in Cheek Tour of My Favourite House in Key West
A dream home with guest cottage, tropical gardens & pool and only two doors down from Sodom & Gomorrah. You only need a bonkers $6.3m. Starts raiding piggy bank!
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This is the final Key West post for this year (possibly), but I have saved the best till last. A week ago I took you on a thrilling, nay, scintillating tour of a lovely historic home on Southard Street, Key West. If you missed it then please catch up, honestly!
But, before I showed you around its fishing rod/stuffed barracuda calypso-crazy vibes, we walked past my favourite home on the island, just across the road from where we stay at the tranquil and supremely aloof LGBT/straight-friendly Alexander’s Guesthouse, 1118 Fleming Street.
Yes, Alexander’s may have a Sunbeam Grocery (don’t get your hopes up) next door with the odd minging hooker and drunk being sick outside, but if you put a peg on your nose when you’re shopping for Côtes De Provence you’d think you were in Notting Hill.
It’s the respectable side of the street you see, none of that all male Auld Lang Syne (think about it) saucy malarkey in the pool that you get from across the road at Island House, I’ll thank you kindly! Not with the lesbians close by at any rate.
Anyway, I digress. I told you a great big porky pie. I told you that house wasn’t for sale, but by Jiminy I was wrong!
It’s been on and off the market since 2021 more times than Katie Price’s pay per view knickers. I remember seeing it for sale last year and presumed it had been snapped up by some multi-millionaire idiot because it wasn’t listed in the open house pages.
Alas, I fear it may be on the market for some time longer as the website estimated value is around $5.7m (honestly, I can see this falling further) and it’s being marketed somewhat higher. Although, it has come down in price substantially from its 2021 price of $7.5m!



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Built in 1925, this historic Eyebrow House, as the style is known, encapsulates the shear beauty of the island and why I’m drawn to it so much. Don’t take my Tomfoolery to heart. I love this house. It’s exceptional. I just find the price completely bonkers and sincererely hope that Key West realty sees sense sometime soon.
The perfect symmetry on the front porch pleases me no end and its lush, tropical gardens are a prime example of Conch Republic charm. It was purchased in 2014 for a mere $1.3m and I remember seeing the extensive renovations unfold. They did an absolutely superb job, I must say. It oozes curb appeal with its chain-hung central lantern and matching wall sconces.
The shutters in the perfect blue-black (possibly Farrow and Ball’s Railings) are true working shutters for both shade and some protection from storms. But, it’s the central columns rising to the expansive overhang, or eyebrow, which makes this, for me, the quintessential Key West architectural style.
The Eyebrow House
If you’ve been looking at the photo of the front of this home and wondering why on earth it was designed to have such a huge overhanging canopy, which completely blocks the view from the upstairs windows, you would not be the first to be puzzled. In fact, it is Key West’s trademark form of architecture and it actually has a purpose.
Typically gable-roofed, the Eyebrow House is distinguished by a large canopy over the top floor windows designed specifically to block out the sun. No way! WAY!
Most of these homes were built prior to the water pipeline that was constructed to serve the island in 1942. That meant that the lush vegetation that we associate with The Keys didn’t really exist back then, which meant the much needed shade they provide was scarce.
Shutters and deep overhanging awnings were the only way to try and stay fresh and cool unless you fancied running around starkers in nothing but your crinoline, whilst wafting a feather duster at your undercarriage.






Inside 1109 Fleming
After seeing all the photos and the video tour (linked tantalisingly below) I now know why this is my favourite house on the island. Once inside you are transported to another world. It’s completely private.
It’s actually two homes in one expansive lot. That’s almost unheard of in Old Town Key West. With six ensuite bedrooms, a seventh bathroom just incase you get caught short, off-street parking, which is a very rare thing here, newly constructed guest accommodation and the most beautiful of salt water pools, it’s hard to beat. Although I can’t help thinking there’s a tiny hint of porn movie pool vibe going on, but maybe that’s just me.
The Dade County pine walls are a bit of a love it or hate it Marmite feature. Personally, I think they’re charming and showcase the home’s history, but some might find them too close to Trump satsuma orange. You could always paint them, although I do think that’s verging on sacrilegious.






There’s a 12-person dining room (I’d change that to eight, the four other people are always fillers and get on everyone’s nerves) and a very high spec chef’s kitchen. Elegant French doors open to a wrap-around porch that blends indoor and outdoor living perfectly.
The guest house is pretty darn fabulous with soaring vaulted ceilings, exposed cross beams, and the cutest of sleeping lofts fit for even the most vertically challenged of Oompa Loompas. There are two ensuite bedrooms there and a full kitchen fitted, so there’s almost no need for your guests to bother you at all.
Separating the two homes is the lushest of tropical paradises surrounding a saline pool and waterfall - just needs a swing (cue scene from The Bitch or The Stud).
What’s the quickest way I can get hold of $6.3m? Don’t say sell my body because I’ve tried that and only made £1.50 and that was with complimentary marmalade-flavoured macarons and quick game of ping pong. Answers on a postcard please. Honestly, you’re in for a treat. You can thank me later.
Go on, if you liked this then please show it! PLEASE do leave a heart ♥️ and a comment if you want to. If you really want to make my day Restack it (that’s the recycle symbol below) as well. It’s so important and it only takes a mo. Luv ya!
Oh my goodness, JP! You don't half make me laugh! I giggled all the way through this wonderful piece and just when I thought it couldn't get better I see a caption that includes "on a bike with no breaks"!😂😂 That's passion for you. I remember you talking about this house last time you were there. Wouldn't it be something if one day you actually owned it??!!! Or is the 'if only' more enticing than the veritable keys in hand?
I adore symmetry (my favourite houses are Georgian double- fronted, sigh...) and I adore weatherboard houses and particularly ones with porches. It reminds me of home ( though my home ones would be more rustic/shabby and not chic shabby😅)
Talking about that pool and your porn movie vibe take, I'm thinking of those Jackie Collins novels that had me hooked way back in the day. I couldn't get enough of them!
Thank you for sharing this, JP. Made my day.
Frannyx
Absolutely Florida design! Thank you for sharing the tour JP! A bit pricey! Ouch!💰🤑💰💸🌴🍹