Three House Tours from Key West, Florida

An Old Town estate with two guest cottages, pool & gardens, an historic eyebrow house with an exceptional finish, pool and four bedrooms, and a monthly holiday rental on millionaire’s row!

JP Clark
Apr 12, 2026

Hi there friendly faces and I hope you are all doing well on this fine Sunday. I’m back home from the Florida Keys and was very happy to be greeted by sunshine and a garden in bloom, although the temperature in West Sussex has plummeted somewhat since our arrival.

Today’s post is centred on home tours in America. I know, I know! We had so many friends and family asking why we were travelling there with everything that is going on. But, the way I see it, we meet around 30 friends there every year, dear friends we love, none of which support the current administration.

In fact, they are all firmly against everything the government is doing, and actually feel quite ashamed to call themselves Americans right now. But, also, I don’t think it’s right to punish a guesthouse, a business, which we love dearly, and its guests who share nothing but kindness, just because of their president’s actions. They didn’t vote him in.

It was incredibly strange being there with them, going to bed thinking the world was about to end just because of one man. Please know many Americans feel as helpless, sorrowful and indignant all at the same time, just like we do.

Anyway, on a lighter note, the tulips I planted in December are out, and I can’t tell you how happy I was to see so many survived the squirrel’s midnight munching. There are gaps though, and for some reason Queen of the Night seemed to be their favourite, along with White Triumphator. But, the Purple Heart and Silver Cloud varieties are glorious, the sunlight only adding to their splendour. My full list of tulip bulb choices can be found here.

Tomorrow the scaffolding will start to be erected around the barn ready for the build and renovations. I’ve been told it’s going to take 2-3 weeks to construct the protective frame and tin roof, but I’m hoping it’s less. We’ve been finishing off moving everything out over the last few days and, as of this evening, the annexe will be home for the foreseeable future (which, I have to say is an absolute luxury, and the first time we will ever get to stay on site without having to live with no roof and endless rubble and dust). It’s all very exciting and scary at the same time, but I can’t wait to bring you all along for the ride.

If you’re new here, then welcome and thank you for choosing to subscribe to Home & Hort. There are so many fabulous choices on Substack, so I feel truly honoured you are here. As a catch up, here’s something that will tell you all about our plans.

House Tours

But, let’s get on to the point of today’s post: a good old nosey around a few islander’s homes. Saturday and Sunday in Key West is open house day. You can find listings online and just rock up to any house that takes your fancy, it’s the most fun ever.

The Key West I know is so very different from the one that most tourists see. The crazy, fun-loving, boozy Duval Street and Mallory Square is great for a short while, but I want the tranquil beauty of the historic home district away from the hustle and bustle.

We always stay on Fleming Street at Alexander’s Guesthouse, and today I’ll be showing you three properties that are within striking distance. I must thank Terri Spottswood and her son John for showing me the first two homes, and Jeff Smead for the invite to see the stunning holiday villa.

1113 Stump Lane

Built in 1938, 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.

For someone with a cool $4,450,000, this home is pretty damn perfect. No one needs a huge plot in the keys, it’s too darn hot, to quote Cole Porter, for faffing with weeding and maintenance. All you need is an outside space for dining, a pool, plus verandahs and balconies for whiling away the hours. This house has that in spades.

It’s 2,985 sqft with four bedrooms and 4.5 baths, which are truly spa-like, two contemporary staircases, a fabulous open-plan kitchen/diner, the perfect sized pool, outdoor shower, which can be accessed from both inside and out, and a surprisingly large rear garden. See listing.

The Eyebrow House

Typically gable-roofed, the Eyebrow House is distinguished by a large canopy over the top floor windows designed specifically to block out the sun. 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.

Next up is a very rare thing on the island: a home with two extra guest cottages.

1006-1008 Fleming Street

In 2014 on our annual pilgrimage to Key West, I fell in love with what I thought was a tiny little house on Fleming Street. I could see that it extended a little further back, but had no idea it was as vast as you’re about to see! The style and colouring of the exterior would form the inspiration for our previous weatherboard home in Surrey, England, which we completed in 2017.

The little house at the front is actually a guest cottage, with the main home in the centre of the plot. A very inviting saltwater pool, patio and gardens separate the house from another guest cottage at the end of the plot, which also has its own private courtyard. See listing.

Finally, it’s the holiday home you can rent on a monthly basis.

The Villas at Island Mates Manor

Across the road from where we stay is an all-male gay guest house called Island House. Next to it, married owners Jeff & James, live in a historic home at the front of the property facing Fleming St. The two Villas in the rear of the property were built from the ground up in 2025. Each of the two luxury Villas feature a split-level layout on three floors, and have 2 bedrooms and 2.5 bathrooms each, offering all King beds, en suites with private balconies and dedicated work/study spaces. The Villas feature ultra-modern chef-style kitchen/living areas. Both units have dedicated covered parking. The Villas and the property owners exclusively share a large swimming pool, hot tub, and deck.

Residents can enjoy private access to the 24-hour Island House Cafe & Bar located directly next door. Now, the pool area is generally clothing optional when its residents are gay males, but anyone of any persuasion can actually book either of the villas, and when that’s the case, any modesty will be accommodated and respected. Book a villa.

That’s it for this week my friends. I’ll be back on Thursday with a little about the barn renovations and the garden.