Living in Key West

Stephanie & Greg

Welcome to Living in Key West, where island life, local stories, and Florida Keys real estate come together. Join Stephanie and Greg Gordon for Wake Up in Key West, a morning show featuring conversations about life on the island, local news, fascinating history, community happenings, and the occasional unexpected detour. From the places and people that make Key West special to the realities of living and owning property throughout the Florida Keys, we bring you an insider's perspective with plenty of personality. Greg is the broker and owner of The Island Collective Realty, a boutique real estate brokerage serving Key West and throughout the Florida Keys. Together, we share local insight, real estate conversations, and a genuine appreciation for the communities we call home. Whether you live here, dream of moving here, or simply love the Keys, we're glad you're joining us.

  1. 2d ago

    Wake Up in Key West | Haunted Cemetery, Local News & Real Estate

    Would you walk through the Key West Cemetery alone at night? 👻🌴 Grab your coffee because today we’re heading into one of the most fascinating places in Key West. We’re digging into the history of the Key West Cemetery, including the hurricane that led to its creation, the surprising number of people believed to be buried there, and some of the ghost stories and strange encounters that have become part of its lore. And since we’re talking cemeteries, we also decided what we’d put on our own headstones. 😂 We’re not giving those away here, but Stephanie’s probably won’t surprise anyone who knows her. Which leads to the very important question... If you could choose your own Key West headstone inscription, what would it say? Before things get spooky, we’re catching up on some big conversations happening around the island. Greg has a property of the day and a little real estate education about transient versus nontransient rentals in Key West. We’re also talking about the proposals for the future of our only hospital, the latest movement on Key West’s sargassum problem, and the debate over what should happen to the old Diesel Plant in Bahama Village. 🌴 Local news, real estate, Key West history, ghosts and whatever else we happen to get into along the way. Basically, another morning with us. ☕️🌴 🎙️ Wake Up in Key West New episodes Monday, Wednesday + Friday. Support the show

    Wake Up in Key West | Haunted Cemetery, Local News & Real Estate

  2. 4d ago

    Wake Up in Key West | Robert the Doll, Real Estate & Island Happenings

    Custom T shirts, long distance sourdough lessons and a haunted doll who apparently expects you to mind your manners. Just another morning in Key West. ☕️🌴 Today we’re catching up on our week before heading into a little Key West history with some Truman Little White House trivia. And somehow Greg manages to turn that into the perfect excuse to show you a pretty incredible double property on Truman Avenue with transient licenses for nightly rentals. 👀🏡 We’re also talking about two things happening in our community right now. The big decision ahead for Key West’s only hospital and the Key West Little Pantry, where neighbors are quietly helping neighbors right here on the island. ❤️ And then things get weird. Stephanie tells Greg the story of Robert the Doll, including the very important rule that you’re supposed to ask Robert’s permission before taking his picture. So naturally, we need to know... Would YOU ask a doll for permission before taking his picture? 👻😂 Grab your coffee and come hang out with us. 🎙️ Wake Up in Key West New episodes Monday, Wednesday + Friday. Support the show

    Wake Up in Key West | Robert the Doll, Real Estate & Island Happenings

  3. 6d ago

    Wake Up in Key West | Ghosts, Black Cats, Football & Island Life

    Grab your coffee because we have a very October morning in Key West for you. ☕️🌴👻 We’re puppy sitting, talking football, and sharing some of what’s happening around the island this week, including a new BBQ spot we tried, the reopening of Café Solé, what’s coming to the Waterfront Playhouse, and an interactive art installation headed to Fantasy Fest. We’re also talking about the absolutely ridiculous amount of rain Key West got last week. If it felt historic, apparently it was. October 1 brought 3.64 inches of rain and broke a daily rainfall record that had stood for 83 years. ☔️ And because October is Black Cat Awareness Month, we’re talking about why black cats have historically had a harder time getting adopted, where some of those old superstitions came from, and the cultures where a black cat is actually considered a sign of good luck. 🐈‍⬛ Then things get a little spooky. Our Key West trivia question takes us to Captain Tony’s Saloon and the surprising original use of the building. From there, we get into the story of the enormous tree growing right through the middle of the bar, the legend of the Lady in Blue, and some very creepy discoveries reportedly made beneath the floor during renovations. 👻 Some of it is documented Key West history. Some of it is legend. All of it is very Key West. Football, food, puppies, black cats, island happenings and a Key West ghost story. Basically, another morning with us. ☕️🌴 🎙️ Wake Up in Key West New episodes Monday, Wednesday + Friday. Support the show

    Wake Up in Key West | Ghosts, Black Cats, Football & Island Life

  4. Oct 2

    Wake Up in Key West | The Sargassum Problem, Football & October on the Island

    Happy October from Key West! 🎃🌴☕️ Grab your coffee because we have plenty to talk about this morning. We’re kicking things off with a little college football chatter, making our picks for some of the best games this weekend and, arguably more importantly, talking about what we’re cooking and eating while we watch. 🏈 We’re also tackling one of October’s most divisive questions. Candy corn. Are you eating it or throwing it directly in the trash? 😂 Then we’re talking about our attempts to go a little more analog, sharing some book recommendations, and discussing just how rainy Key West has been lately. But our biggest conversation today is about something anyone who lives in or visits the Keys has probably encountered: sargassum. What exactly is causing the sargassum problem? Why has there been so much of it? What is Key West doing about it? What solutions are being explored, and what can we learn from the way other places around the world are dealing with it? It’s one of those complicated island issues without a simple answer, so we’re digging into what’s happening and what could potentially be done about it. College football, books, candy corn, island life and a deep dive into one of the biggest environmental challenges facing Key West. Basically, another morning with us. ☕️🌴 🎙️ Wake Up in Key West New episodes Monday, Wednesday + Friday. Support the show

    Wake Up in Key West | The Sargassum Problem, Football & October on the Island

  5. Sep 30

    Wake Up in Key West | Duval Street, Lower Keys Boating & the Legend of Bum Farto

    Grab your coffee and Wake Up in Key West with us. ☕️🌴 Today’s episode has a little bit of everything that makes life in the Keys interesting. We’re talking about the recent traffic snafu on Duval Street, giving you the latest update in Greg’s ongoing beach chair saga, and reminding you about our Guide to Key West for anyone planning a trip to the island. Then we’re talking real estate and heading up the Keys for a conversation about something that can be confusing if you’re considering buying in the Lower Keys. What does boating and open water access actually look like depending on where you buy? We’re breaking down why location matters and some of the things you’ll want to understand before choosing an island or neighborhood. And finally, a little Key West trivia leads us into one of the island’s most legendary stories. The curious case of Bum Farto. 👀 Key West life, local stories, real estate, island history and whatever else we happen to get into that morning. Pour another cup and come hang out with us. ☕️🌴 🎙️ Wake Up in Key West New episodes Monday, Wednesday + Friday. Support the show

    Wake Up in Key West | Duval Street, Lower Keys Boating & the Legend of Bum Farto

  6. Sep 28

    Wake Up in Key West | Island Life, Our Gators Road Trip & What’s Next

    We’re back and we have a lot to catch up on. 🌴☕️ In today’s episode, we’re sharing what’s been going on with us lately, including our road trip to Auburn to watch the Gators come home with a win 🐊, what life has been looking like back on the island, and the fact that somehow going to the beach multiple times a week has become a completely normal part of our lives. We’re also talking about what’s next for the podcast. Going forward, you can Wake Up in Key West with us every Monday, Wednesday and Friday. More conversations about island life, what’s happening around Key West, real estate, and whatever else we happen to get into. And for those of you looking ahead at another long, cold winter… consider this your reminder that you don’t actually have to spend all of them that way. 😉 If owning a home in Key West or anywhere in the Florida Keys has been somewhere in the back of your mind, reach out. We’d love to help you explore what island life could look like for you. Grab your coffee and come hang out with us. ☕️🌴 🎙️ Wake Up in Key West New episodes Monday, Wednesday + Friday. Support the show

    Wake Up in Key West | Island Life, Our Gators Road Trip & What’s Next

  7. Feb 11

    New pod 🎙️ Season 2 Episode 2

    Keys real estate is heating up 🔥 + bread talk 🍞 + rescue pups 🐾 + weather + new restaurant spots 🍽️🌴 Support the show

  8. 10/22/2025

    Life in the Florida Keys: Starting Our Brokerage, Power Boat Races & Remembering Winnie

    Welcome back to the Living in Key West Podcast — your inside look at real life in the Florida Keys! 🏡✨ This episode is a big one. We’re sharing the story behind launching our own Florida Keys real estate brokerage and what it means for our future, our agents, and our community. We also talk about bringing on agents, current real estate trends, and iconic Florida Keys events happening this season. We cover: 🏝️ Starting our own brokerage & growing the team across the Florida Keys 🏠 Real estate market updates and what’s next for buyers and sellers 🎭 Fantasy Fest and island celebrations 🚤 Power Boat Races and why locals love this time of year 🐶 Remembering Winnie and honoring the heart of our journey Whether you’re dreaming of moving to the Florida Keys, buying or selling property, or just love island life — this episode gives a candid look behind the scenes of living and working in paradise. 👉 Don’t forget to like, comment, and subscribe for more weekly conversations about Florida Keys living, real estate, and building a business from the ground up. 📲 Follow us: Instagram: @livininkeywest TikTok: @livinginkeywest Website: https://theislandcollectiverealty.com Support the show

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5
out of 5
9 Ratings

About

Welcome to Living in Key West, where island life, local stories, and Florida Keys real estate come together. Join Stephanie and Greg Gordon for Wake Up in Key West, a morning show featuring conversations about life on the island, local news, fascinating history, community happenings, and the occasional unexpected detour. From the places and people that make Key West special to the realities of living and owning property throughout the Florida Keys, we bring you an insider's perspective with plenty of personality. Greg is the broker and owner of The Island Collective Realty, a boutique real estate brokerage serving Key West and throughout the Florida Keys. Together, we share local insight, real estate conversations, and a genuine appreciation for the communities we call home. Whether you live here, dream of moving here, or simply love the Keys, we're glad you're joining us.

Information

  • Creator
    Stephanie & Greg
  • Years Active
    2022 - 2026
  • Episodes
    64
  • Rating
    Clean
  • Copyright
    © 2026 Living in Key West
  • Show Website
    Living in Key West

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