Expert commentary + data-driven predictions from ShineGroup — what Keys buyers, sellers, and investors need to know next year. Key takeaways up front Prices are cooling but remain high  — Monroe County’s median home price sits well over $900K–$1.2M depending on the dataset, and the market is showing signs of normalization after pandemic-era highs.  Inventory and days-on-market are rising,  giving buyers more options and bargaining power in many segments.  Short-term rental (STR) rules remain a major driver  — stricter permitting, zoning, and advertising rules are reshaping the STR investment thesis across the Keys. Compliance and local licensing are essential for 2026.  Tourism fundamentals are steady  (occupancy and TDT revenues holding), supporting vacation-rental demand—though growth is more modest than prior years.  1) 2025 context → how it shapes 2026 2025 closed with higher inventory and longer time-to-sale compared with the red-hot market of 2020–2022. Median listing and sale prices in Monroe County remain among Florida’s highest, but month-to-month figures show a softening trend rather than a crash. That combination points to a  gradual market correction  in 2026 rather than a sudden droP especially for non-waterfront, non-luxury homes.  Why this matters:  sellers who priced aggressively in 2021–22 will need to be realistic; buyers can find better negotiating leverage on more listings. 2) Price & inventory outlook (what to expect) Price range:  Expect a  modest downward or flat adjustment  (low single-digit percentage range) for many neighborhoods in 2026 as mortgage rates continue to influence affordability and sellers adjust to new comps. Luxury waterfront properties and unique island estates will be more resilient.  Inventory:  More active listings and moderately longer days on market give buyers time to compare, and could push some sellers to offer incentives (credit for insurance, closing assistance, flexible escrow).  Renter demand:  Seasonal tourism remains supportive for demand in desirable short-term markets; mid-term and long-term rentals may see upticks as buying becomes less affordable for some. 3) Short-term rentals & regulations — the biggest variable for investors Regulatory changes are the single largest risk/reward factor for STR investors heading into 2026. Monroe County’s  Special Vacation Rental Program  and city-level licensing in places like Key West require permits, manager licensing, and advertising that reflects minimum stay requirements. Non-compliance risks fines, delisting from platforms, or permit denial.  Prediction:  Local governments will continue to refine STR policy expect stricter enforcement, clearer permitting timelines, and potentially more caps or zoning-based restrictions in higher-density areas. Investors must add regulatory risk to underwriting models. Action for investors:  before you buy for STR income, verify (1) zoning, (2) permit pathway, (3) local occupancy taxes and TDC registration, and (4) realistic occupancy/ADR assumptions accounting for possible 28-day minimums in some districts. 4) Neighborhoods & product types to watch Old Town Key West / Historic Core:  Remains premium—strong demand for turnkey, historic cottages; limited supply keeps values higher. STR rules and historic preservation may limit investor conversions.  Waterfront & island estates:  Luxury will stay resilient; buyers seeking lifestyle and scarcity will continue to compete. Marathon / Lower Keys:  More land and comparatively lower entry price for waterfront living attractive to second-home buyers and longer-term rentals. Infill / condos / 55+ product:  With affordability pressures, look for growth in condos and age-restricted communities that target downsizers and seasonal residents. 5) Insurance, climate risk & lending — practical considerations Insurance costs & availability  continue to be a top practical factor for transactions in the Keys. Underwriting changes and higher premiums will affect net buyer budgets and should be forecasted into offers. Flood risk and resiliency measures  (elevations, impact windows, newer roofs) are increasingly valuable in pricing and in qualifying for better insurance rates. ShineGroup tip:  show buyers an insurance estimate early in the process. It’s a deal-maker (or breaker) in many Monroe County transactions. Final word why ShineGroup is your 2026 Keys partner The Keys market is local, nuanced, and heavily influenced by regulations, tourism, and climate-related costs. ShineGroup blends island-level market intel with hands-on transaction experience and community connections. Whether you’re buying a cozy Old Town cottage, selling an estate, or evaluating an investment with STR risk, we provide the data, local insight, and tactical guidance you need. Want a custom Monroe County market snapshot for your neighborhood or an investment feasibility model? Tell us the address or property type and we’ll build a tailored analysis with local comps, projected cash flow, and compliance checklist. — Krystal & Jess

Because palm trees look even better wrapped in twinkle lights.   The holidays hit different down here in Key West instead of snowflakes, we get salt air; instead of fireplaces, we gather by the water. But trust us, the island knows  exactly  how to bring the festive spirit, island-style! Lighted Boat Parade – December 14, 2025 Nothing says “Florida Christmas” quite like a parade of boats decked out in twinkling lights, wreaths, and inflatable flamingos. The  Key West Lighted Boat Parade  is a local legend picture yachts, fishing boats, and even kayaks gliding through the Historic Seaport, all aglow. Pro tip:  Grab a spot early along the Harbor Walk or book a dinner reservation at one of the waterfront restaurants for the best view (and a margarita in hand). Holiday Historic Inn Tour – December 6 & 13, 2025 Take a stroll through Key West’s most charming inns, each dressed up for the holidays with island flair. Think lush tropical wreaths, vintage decorations, and plenty of warm welcomes. This annual event supports the  Hospice & Visiting Nurse Association , so you’ll be giving back while soaking in some serious holiday charm. Don’t miss:  Complimentary treats and cocktails at each stop a little taste of local hospitality never hurts! Key West Holiday Village – All December at Truman Waterfront Park The  Key West Holiday Village  turns Truman Waterfront Park into a twinkling wonderland the whole month of December. Expect festive lights, a pop-up market, food trucks, live music, and even a visit from Santa (who, yes, sometimes arrives by boat). It’s perfect for families, date nights, or anyone who just wants to stroll through holiday cheer in board shorts. Bonus Festivities You’ll Love Historic Seaport “Bight Before Christmas” Celebration  – nightly lights, carolers, and waterfront vibes. New Year’s Eve Drops  – from the famous Conch Shell at Sloppy Joe’s to the Red Shoe Drop on Duval, Key West rings in the New Year like no one else. Island Holiday Markets  – shop local for handmade gifts, art, and tropical ornaments you won’t find anywhere else. Tag your photos with  #KeyWestHolidays  and share the island magic because down here, Christmas is all about sunshine, smiles, and a touch of salt air.

Ask anyone who calls Key West home, and they’ll tell you November is pure magic. The summer heat has softened, the skies stay brilliantly blue, and a light breeze rolls in that makes every bike ride, beach walk, and evening on the porch feel just right. It’s the kind of weather that reminds you why you fell in love with island life in the first place. This is the locals’ season , the calm before the holiday rush, when the streets are lively but never too crowded, and you can still grab a seat at your favorite restaurant without a wait. It’s the month when the snowbirds start to trickle in, the marinas hum with activity, and boating days are picture-perfect. The water is warm, the sunsets are breathtaking, and the pace of life hits that perfect Key West rhythm, easygoing yet full of possibility. For us at ShineGroup, November captures the heart of what it means to live in the Keys. It’s a time to reconnect with community, to enjoy the small moments, morning strolls along the harbor, local art walks, sunset sails with friends. It’s also the start of the season when the island begins to sparkle with holiday lights and a spirit of togetherness that only Key West can create. So, as the rest of the country pulls out sweaters and snow shovels, we’re grateful for balmy evenings, salty breezes, and that unmistakable island charm that makes every November here feel a little like a homecoming. 🌴☀️

If you bought a home in the Florida Keys this year, now’s the time to get ready for one of the biggest homeowner perks the Florida Homestead Exemption. This benefit can save you thousands on your property taxes each year, but only if you file on time! What Is the Homestead Exemption? The Florida Homestead Exemption reduces the taxable value of your primary residence by up to $50,000, potentially lowering your annual property tax bill. It also caps how much your assessed value can increase each year (no more than 3%), offering long-term protection from rising taxes a huge advantage in our appreciating Keys market. Key Filing Deadlines for 2025 Filing period: January 1 – March 1, 2025 Where to file: Monroe County Property Appraiser’s Office ( mcpafl.org ) Who qualifies: Florida residents who own and occupy their home as their primary residence as of January 1, 2025 If you miss the March 1 deadline, you’ll likely have to wait another year to receive the exemption so planning this November is key. What You’ll Need Gather your documents early so you’re ready to file right after the new year. You’ll typically need: Florida driver’s license or ID with your home address Vehicle registration (with the same address) Voter registration or Declaration of Domicile Property deed or closing statement Why Prepping in November Matters Taking a few minutes now to organize your paperwork can mean real savings later. Many homeowners wait until January, only to scramble or miss out entirely. By preparing early, you’ll be ready to file right away and lock in valuable tax savings for years to come. If Key West (or anywhere in the Keys) is truly home, make it official with the Homestead Exemption. Mark your calendar for January 1, have your documents ready, and give yourself the gift of lower taxes in 2025!

If you own property in Monroe County (the Florida Keys), here’s a friendly breakdown of how assessments, tax bills, and appeals work and what you should do as the year winds down. How Property Assessments Work The sets assessed values for real property as of January 1 each year. They apply exemptions (like the homestead exemption) and classifications that can reduce the taxable value. Once values are set and taxing authorities decide their millage (tax) rates, the tax roll is certified and sent for billing. When Tax Bills Arrive & Payment Timing Tax notices are generally mailed out on or before November 1. You’ll usually find early-payment discount opportunities: 4% discount for payments made in November 3% in December 2% in January 1% in February Full gross amount due in March; delinquent as of April 1. Make sure your mailing address is current. If you don’t receive a bill, you’re still responsible for paying. How to Plan & Prepare Ahead Review your assessed value as soon as the new assessment roll is posted (usually early in the year). Compare to recent comparable sales to check accuracy. Confirm exemptions if you qualify (homestead, senior, widow(er), etc.), and make sure they’re applied correctly before the deadline. Budget for payment, given the timing and discounts, it's wise to earmark funds now so you can pay early and save. Save documentation, keep recent appraisal reports, purchase or remodel receipts, photos, etc., in case you need to appeal. Set aside for possible appeals, if you believe the assessed value is too high, you have the right to file a value-adjustment appeal (through the appropriate board) within stated deadlines. As we approach year-end, this is a smart time to check in  on your property’s assessed value, ensure all exemptions are in place, and plan your payment strategy (or potential appeal). Being proactive means fewer surprises and more control over your tax exposure heading into the new year.

If you own a home (or plan to buy one) in the Florida Keys, flood insurance is more than a box to check; it’s a key part of living smart on the island. With FEMA updates, new flood maps, and evolving insurance rates, understanding how it all fits together can save you money and stress. Here’s what homeowners should know heading into the new year. FEMA Updates & Flood Zones FEMA’s flood maps, known as Flood Insurance Rate Maps (FIRMs),   outline which areas are at higher risk of flooding. Many parts of the Keys fall within Special Flood Hazard Areas (SFHAs), where flood insurance is typically required for homes with a mortgage. Over the last few years, FEMA has updated these maps to reflect modern data on sea level rise and storm impacts. That means your property’s zone may have shifted — and so could your insurance requirements. Tip: You can check your property’s flood zone at msc.fema.gov . Even if you’re not in a “high-risk” zone, coverage is still worth considering. Elevation Certificates: Your Secret Weapon Your Elevation Certificate (EC) measures how your home’s lowest floor compares to the base flood elevation for your area. Insurers use it to calculate premiums — and sometimes, it can make a big  difference in cost. If your home sits higher than the base flood level, your premium could be significantly lower. If you’ve made improvements or raised your foundation, it might be time for a new EC to reflect those updates. FEMA’s “Risk Rating 2.0”: How Premiums Are Calculated Now FEMA’s new Risk Rating 2.0  system has modernized the determination of flood insurance costs. Instead of just using flood zones, the new model considers factors like: Distance from water Property elevation Rebuild cost value Flood frequency history The goal is to make rates more accurate — but for some properties, that means increases. The good news? Discounts and gradual phase-ins help soften the impact for many homeowners. What Buyers and Homeowners Should Do Now Review your current flood policy. Check your renewal date and make sure your coverage still meets your needs. Ask for the Elevation Certificate when buying a home — it’s key to understanding your true insurance costs. Talk to a local insurance expert. Florida Keys agents understand island-specific risks and can often find better options than national carriers. Don’t wait until storm season. Policies usually take 30 days to take effect — so plan early. Flood insurance in the Keys isn’t just about compliance — it’s about peace of mind. With new FEMA updates, evolving flood zones, and smarter pricing models, now’s the perfect time to review your coverage and make sure your home is protected for the year ahead.

If you’ve been thinking about selling your Key West home, November might just be your secret weapon month. While many sellers wait until after the holidays, the smart ones know pre-season timing is everything  here in paradise. 🌞 1. Pre-Season Buyers Are Already Here Snowbirds are arriving, investors are scouting, and seasonal visitors are falling in love with island life all over again. Many are ready to buy now, before peak season competition and rental bookings make it harder to find the right property. Listing in November means you’ll catch these motivated early buyers before the winter rush. 🎁 2. Holiday Timing Works in Your Favor Believe it or not, the holidays bring serious buyers, especially those planning a relocation or second home purchase for the new year. People visiting family (or escaping the cold!) often use their trip to explore real estate options. A well-presented listing during this time stands out when buyer attention is high and inventory is still limited. 🏝️ 3. Limited Inventory = Less Competition Many homeowners wait until January or February to list, meaning November sellers enjoy a quieter playing field. With fewer comparable homes on the market, your property has a better chance to shine and potentially sell faster and closer to the asking price. 💡 The Bottom Line November offers the sweet spot between the quiet fall market and the high-energy winter season. Serious buyers are here, inventory is still low, and the island vibe is just starting to buzz again. If you’ve been on the fence about selling, this could be your moment to make a move before everyone else does.

Here are some top spots in Key West to enjoy Thanksgiving dinner (or takeout!) ranging from relaxed to upscale perfect for a holiday meal or sharing with friends and clients of the ShineGroup. 1. Cafe Marquesa An elegant choice in Old Town — they’re known for a refined Thanksgiving menu featuring roasted turkey, creative sides, and a cozy historic atmosphere. Why ShineGroup loves it :  Ideal for clients or guests seeking a high-end, memorable holiday meal. 2. Conch Republic Seafood Company For a blend of island flavor and holiday tradition, this spot offers a “Thanksgiving in Paradise” vibe, traditional turkey dinner plus Key West flair. Why ShineGroup recommends it :  Great for families or groups who want a fun, local-flavored holiday experience. 3. Four Marlins (Oceanfront Dining) Located in the Reach Resort, this venue serves a la carte Thanksgiving specials and also offers a to-go turkey dinner option for two. Why ShineGroup likes it: Ideal for guests staying in vacation homes who want takeaway or a relaxed ocean-view dinner. 4. Cafe Sole Known for New England-style Thanksgiving fare—turkey with smoked oyster & apple stuffing, mashed potatoes, cranberry-orange compote—offering a traditional holiday meal in Key West. Why ShineGroup books it: A solid choice for clients wanting a more classic Thanksgiving feast in a relaxed setting. ✅ Booking & Take-out Tips Reservations are highly recommended. Thanksgiving is a busy day in Key West. Many restaurants offer special holiday menus and to-go options. If you’re coordinating for clients or rental guests, mention that some places also handle larger parties or group bookings. Confirm holiday hours and pricing ahead of time menus and availability can change.

The holidays in the Florida Keys are about more than sunshine, palm trees, and festive lights; they’re also about community. As we move through the season of gratitude, it’s the perfect time to shine a light on some amazing local organizations making a difference right here in our island paradise. ☀️ Shoveling Sunshine This incredible local nonprofit spreads kindness throughout the Keys, delivering care packages, meals, and small acts of joy to those who need a lift. Their mission is simple: brighten someone’s day, one thoughtful gesture at a time. You can help by donating, volunteering, or sponsoring a “Sunshine Bag” for families and individuals facing tough times this season. ⚓ Rotary Club of Key West The Rotary Club has been serving the Keys community for decades, supporting scholarships, local youth programs, and disaster relief efforts. During the holidays, they ramp up their giving with food drives, holiday events, and community service projects. Joining a Rotary event or donating to their community fund is a great way to give back locally and see your efforts directly impact neighbors in need. 🐾 Florida Keys SPCA The holidays are a perfect time to show love to our furry friends, too! The FKSPCA works year-round rescuing, sheltering, and finding homes for animals throughout the Keys. Donations of supplies, food, or even a few volunteer hours can go a long way, and who knows, you might meet your new best friend while you’re there. 🏡 Habitat for Humanity of Key West and Lower Florida Keys Habitat helps local families build strength and stability through affordable housing. From construction projects to ReStore donations, there are plenty of ways to get involved. Helping someone find a safe place to call home is one of the most meaningful gifts you can give this season. 🌴 Keys Strong & Local Food Pantries Local grassroots groups like Keys Strong and the SOS Foundation continue to support families with food assistance, disaster recovery, and community resources. As the cost of living rises, their services are more critical than ever, and every dollar, grocery bag, or hour volunteered truly makes a difference. 💛 The Spirit of the Season In the Keys, “community” isn’t just a word; it’s a way of life. Whether you donate, volunteer, or simply spread a little kindness, every effort adds up. This holiday season, let’s all do our part to make sure the warmth we feel here extends beyond our own homes.

Hey! November is here, and if you’ve been around town, you’ve probably noticed things picking up more visitors, more golf carts, and yes, more real estate activity. Let’s break down what’s happening as snowbirds return and the season kicks into gear. 🏝️ Inventory: A Gentle Uptick Listings are slowly increasing as seasonal homeowners return, but supply is still tight overall. The most desirable homes especially in Old Town and Casa Marina — continue to move quickly. You’ll find more options now than in summer, but it’s still very much a seller’s market for move-in-ready properties. 💰 Pricing: Steady but Strategic Average home values hover around $1M, with slight softening in some condo and New Town segments. Sellers who price smartly and present their homes well are still landing strong offers. Overpriced or outdated listings? They’re sitting longer. 🚤 Buyer Activity: Snowbirds + Investors November brings cash buyers, second-home shoppers, and investors eyeing rental-income potential. Many are motivated to secure a property before peak season, so well-priced homes are drawing attention fast. 🌴 What National Reports Miss Key West is its own world. Short-term rental demand, flood insurance costs, and micro-neighborhood trends shape our market far more than national averages. A property’s exact location sometimes just a few blocks apart can make a big difference. ✨ Bottom Line Yes, the Key West market is heating up slowly but surely. Inventory is creeping higher, buyers are back, and the best homes still sell fast. If you’re thinking about buying or selling this season, now’s the perfect time to make your move while the island energy is high and the competition hasn’t peaked.

As we step into the final quarter of 2025, the Florida Keys real estate market shows a return to balance after two years of dynamic shifts. While summer brought record-level activity across Key West and the Middle and Lower Keys, September reflected the usual seasonal cooling with prices stabilizing, days on market lengthening, and buyers regaining negotiation power. Let’s take a closer look at how each area performed and what these numbers could mean heading into year-end. Key West (33040): Cooling into a Healthy Balance The Key West market remains strong even as activity slows seasonally. The average sale price rose to $1.34M, up 26% year-over-year, driven by luxury and mid-range homes. The median price reached $877,500, slightly below August’s $900K.Inventory increased 13% YoY to 1,414 listings, though new listings fell to 199. Homes are taking longer to sell at 117 days on average, yet demand remains steady with an absorption rate of 10.16. Outlook: Expect stable prices through the holidays as sellers adjust and well-priced homes continue to attract buyers. Middle Keys (33043): Resilient Growth, Steady Demand The Middle Keys continue to thrive with an average sale price of $1.35M, up 26% YoY, and a slight rise in median values. Despite 22% fewer new listings, sales climbed to 136 homes, showing strong buyer activity. Homes now spend 117 days on market, but pricing confidence remains firm. Outlook: The region is on track for healthy, sustainable growth into 2026, offering a balanced market where both buyers and sellers have room to negotiate. Lower Keys (33042): Signs of Stabilization After Correction The Lower Keys show a 35% drop in average sale price from $1.63M to $1.06M, reflecting fewer luxury sales. However, the median price rebounded 11% MoM to $999K, signaling early recovery. Inventory is steady at 146 listings, with few new entries (15). Homes take around 90 days to sell, indicating a slower but stabilizing market. Outlook: The area favors buyers for now, though limited new listings could tighten supply again by winter. Florida Keys Outlook: Q4 2025 and Beyond The Florida Keys are moving toward sustained equilibrium after years of volatility. Inventory is steady, pricing is holding, and longer market times point to a healthier, more deliberate pace. Prediction: Expect moderate price growth and balanced absorption through late 2025, with renewed demand likely in early 2026 as mortgage rates ease. Takeaway: Balance is back. For sellers, strategic pricing and presentation are key. For buyers, now is the moment to act before spring competition heats up.

November 1 9th Annual Tiki Man Radio Songwriters Dead- Zep Trop Rock Junkies at Schooner Wharf Bar November 2 Key West Artisan Market: Keys to the Future Edition 44th Annual Offshore World Championship First State Bank World's Fastest Boat Parade November 3 44th Annual Offshore World Championship Trivia Night November 4 44th Annual Offshore World Championship November 5 44th Annual Offshore World Championship November 6 44th Annual Offshore World Championship November 7 Dual Street Party _ Key West Style 44th Annual Offshore World Championship Thomas Dolby " The Icon of the 80's" @ Key West Theater November 8 44th Annual Offshore World Championship Wheeland Brothers @ Key West Theater November 9 44th Annual Offshore World Championship Sheriff's Animal Farm Open House November 10 November 11 November 12 Key West Film Festival 2025 Elton Dan @ Key West Theater November 13 Key West Film Festival 2025 November 14 Key West Film Festival 2025 Annual Casino Night Gala November 15 Key West Film Festival 2025 The Garcia Project: Performing a full Classic Jerry Garcia set November 16 Key West Film Festival 2025 Golden Girls: The Tribute Show- A Drag Parody @ Key West Theater Zack Seemiller: This Show Saves Lives November 17 November 18 November 19 November 20 November 21 A Celebration of the Songs of Pete & Wayne November 22 Crystal Gayle @ Key West Theater November 23 Sheriff's Animal Farm Open House November 24 The Carole King & James Taylor November 25 November 26 Annual Lobster Trap Christmas Tree Lighting Lighting of the Bight Tony Baltimore- Dinner & A Show ft Tim Conroy November 27 Thanksgiving Day November 28 November 29 The Broken Hearts 30th Annual 5K Hog Trot November 30 Kilts in the Keys