Florida Keys Real EstateMonday Market UpdateNew ListingSold Listings November 3, 2025

Monday Morning Market Update – Florida Keys Real Estate

Another week has wrapped up here in paradise, and the Florida Keys market continues to buzz with activity!

Last week, 75 new properties were listed for sale across the Keys. There’s no shortage of impressive oceanfront estatesthat capture the dream of waterfront living, but there are also some fantastic budget-friendly options on the market. Whether you’re looking for a cozy condo, a townhome with amenities, or a private luxury retreat, there’s something for every lifestyle and price point.

👉 See the new listings here: View New Listings

On the sales side, 33 properties closed last week, showing the same wide range in prices. The highest sale was an incredible canal front estate that sold for $3,275,000 — proof that premium waterfront homes continue to attract strong interest.

👉 See the closed sales here: View Closed Sales

While the Florida Keys are often thought of as a “rich man’s paradise,” the truth is that there are homes available for every buyer — from entry-level condos to luxurious oceanfront estates. The Keys lifestyle is about more than price; it’s about enjoying the sun, the sea, and a community that feels like home.

If you’re thinking about buying or selling, now is a great time to take a closer look at what’s available.

 

closed salesFlorida Keys Real EstateMarket Activitynew listings October 27, 2025

Monday Market Update: Your Weekly Look at the Florida Keys Real Estate Scene

Welcome to another Monday Market Update. First, a quick note from me. I was a bit quieter online last week. Physical therapy during my surgery recovery has been a real workout. I am powering through, and I appreciate your patience and support.

Let’s jump into the good stuff.

New Listings: Fresh Homes and Fresh Possibilities

There were 68 new listings across the Keys last week. Prices ranged from $349,000 for a cute condo in Marathon to a breathtaking $15,750,000 open water estate in Lower Matecumbe. It shows that the Keys offer something for almost every budget and dream.

If you want to browse the latest homes on the market, click here.

Sold Listings: What Closed the Deal

We also saw 24 sales wrap up last week. A cozy cottage in Marathon sold for $245,000, while a private waterfront home on exclusive Shark Key reached $4,000,000. Sales like these show that well-priced homes are still moving and buyers are active from Key Largo to Key West.

You can view the closed sales here.

What This Means for You

Whether you are thinking about buying or selling, the market continues to offer real opportunities. Local knowledge and a smart plan make all the difference. That is where I come in. I live here. I work here. I have been helping people move in and move up in the Keys for more than 30 years.

If you are curious what your home might be worth today or want to explore options before the busy winter season ramps up, reach out anytime. I am here to help you make your move with confidence.

First Class FridaysFlorida KeysFlorida Keys Real EstateFlorida Keys Real Estate MarketKey LargoProperty Spotlight October 17, 2025

First Class Friday: Canalfront Living in Crosskey Waterways, Key Largo

Welcome to 614 Santa Anita Lane in Crosskey Waterways, a stunning canalfront home at Mile Marker 103 in Key Largo. This location offers the best of both worlds — an easy mainland commute from Miami-Dade and close proximity to all the shopping, dining, and entertainment that makes Key Largo so special.

Step inside to discover an immaculate, fully remodeled second floor with soaring ceilings, three bedrooms, and two bathrooms. The open-concept kitchen shines with warm wood cabinetry, recessed lighting, and plenty of natural light through impact-resistant windows and doors. A spacious screened patio extends from the living area, offering peaceful views of the pool, dock, and wide turning basin — the perfect spot for morning coffee or sunset cocktails.

But it’s the outdoor living spaces that truly make this home stand out. The backyard oasis features a sparkling private pool and a covered entertainment area complete with a fantastic outdoor bar, comfortable seating area, and a dockside bathroom for convenience. Whether you’re hosting friends for a weekend barbecue or relaxing by the water, this home was built for enjoying the Keys lifestyle.

For boaters, the concrete dock includes a 20,000 lb. boat lift and fish-cleaning station, offering easy access to the ocean or bay via nearby Adams Cut. Built on solid concrete columns and beams, this modular home also includes an elevator shaft ready for future installation.

Beautifully updated and designed for entertaining, this Crosskey Waterways gem perfectly captures the relaxed luxury of life in the Florida Keys.

Click here to see the full listing information and more photos

Listing information provided courtesy of Robert Valenzuela and Century 21 Circle

Community SpotlightFlorida Keys Real EstateKey LargoThe Landings of Largo October 15, 2025

Discover The Landings of Largo

If you’re dreaming of a Keys lifestyle that blends comfort, community, and easy access to the water, look no further than The Landings of Largo. This gated community in the heart of the Upper Keys offers everything from cozy garden apartments to spacious townhomes — all surrounded by tropical landscaping and gentle sea breezes.

A Community Built for Relaxation

Life at The Landings of Largo feels like a retreat. The property features two beautiful swimming pools, including a large one beside the clubhouse — a favorite spot for social gatherings and casual get-togethers. Whether you’re enjoying a morning swim or an evening chat with neighbors, it’s the kind of place that invites you to slow down and stay awhile.

For boaters, the community’s private marina and boat ramp make it simple to get out on the water. Drop your boat in and head toward nearby ocean or bay waters — it’s one of the easiest ways to experience the Keys lifestyle right from home.

Variety and Style in Every Building

The Landings isn’t a cookie-cutter community. It’s made up of several buildings, each with its own unique style and floor plan.

  • Some homes are charming garden apartments, perfect for those who want a low-maintenance space with easy access to community amenities.

  • Others are spacious townhome-style residences with covered parking and multiple levels of living space.

A few of the townhome units even overlook a peaceful pond and mangroves, offering tranquil views that stretch all the way out toward the water. It’s hard to beat sipping your morning coffee while watching the herons glide by.

A Place Close to My Heart

The Landings of Largo isn’t just another beautiful Upper Keys community — it’s personal for me. This is where I cut my teeth as a budding Realtor, learning the ins and outs of Keys real estate and getting to know the incredible people who call this area home. Every time I visit, I’m reminded why I fell in love with this career — and with this community.

Living in the Upper Keys

When you live at The Landings, you’re close to everything that makes the Keys special:

  • Boating and fishing just minutes from your door.

  • Local dining and shops in nearby Tavernier and Key Largo.

  • Top-rated schools and conveniences within easy reach.

  • And of course, the laid-back island lifestyle that draws so many to the Florida Keys.

Explore Available Homes

The Landings of Largo offers a range of home styles and price points. You can view all current listings right here:
👉 See available units at The Landings of Largo

Whether you’re searching for a weekend getaway, a full-time residence, or an investment in paradise, The Landings offers a perfect mix of comfort, convenience, and coastal charm.

financialFlorida Keys Real EstatehomeownershipInvestmentMortgage Advice October 14, 2025

Should I Pay Off My Mortgage or Invest the Money Instead? My Real-Life Dilemma

This isn’t a theoretical question — it’s my real-life decision.

I owe about $108,000 on my home — which is worth roughly $650,000 — at a 4.875% interest rate. My monthly payment is $837, and if I keep making those payments, my last one will be due on December 1, 2040.

But lately, I’ve been wondering:
Would it make more sense to pay off the mortgage right now, and then take that $837 each month and invest itinstead of sending it to the bank?

Let’s look at both sides.

🏠 Option A: Keep the Mortgage

If I keep things as they are, I’ll pay off the home in 15 years and pay around $42,000 in interest by the end.

That’s not terrible, but it’s still money that could be working for me elsewhere.

Pros:

  • I keep my savings intact for emergencies.

  • I benefit from inflation over time (my payment stays the same even as prices rise).

  • I retain flexibility with my cash.

Cons:

  • I’ll still be paying $837 every month until 2040.

  • I’ll pay tens of thousands in interest to the bank.

  • The debt — even manageable — still hangs over my head.

💸 Option B: Pay Off the Mortgage Now and Invest the $837 Monthly

Now imagine this: the mortgage is gone. No more payments. And instead of sending $837 to the bank each month, I invest it — steadily, month after month — for the same 15 years.

Here’s what that might look like based on different average annual returns:

Scenario Average Annual Return Total After 15 Years (Investing $837/month)
Conservative 4% $181,000
Moderate 5% $225,000
Optimistic 6% $243,000
Aggressive 7% $264,000

That’s the potential of compound growth — even small, steady investments can snowball over time.

Of course, markets can fluctuate, and returns aren’t guaranteed. But history shows that long-term investing tends to outperform the cost of most fixed-rate mortgages — especially ones below 5%.

⚖️ Comparing the Two Paths

Pay Off the Mortgage Now Invest the $837 Monthly
Guaranteed 4.875% “return” Potential 6–7% long-term return
Complete peace of mind — no debt More financial growth potential
Frees up $837/month immediately Keeps the mortgage until 2040
Simplifies retirement and lowers expenses Keeps cash more flexible and liquid

🧭 The Bottom Line

Financially, investing the $837 each month could lead to greater long-term gains — assuming the market performs well.

Emotionally and practically, though, paying off the mortgage offers a guaranteed return, immediate relief, and flexibility with future cash flow.

✍️ Tracy’s Take: Why I’m Leaning Toward Paying It Off

For me, peace of mind carries real value. Knowing my home is completely mine — no bank, no payment, no balance — feels like true financial freedom.

Once that monthly $837 isn’t going to the mortgage, I can redirect it however I choose:

  • Invest it each month and watch it grow.

  • Use it for home improvements that boost comfort and value.

  • Or simply enjoy having a little more breathing room in my budget.

It’s not just about numbers — it’s about freedom, flexibility, and the feeling of owning my home outright. And that, to me, is worth every penny.

closed salesFlorida KeysFlorida Keys Real Estatenew listings October 13, 2025

Monday Morning Market Update

Good morning, everyone!

First, I want to take a moment to thank my readers for their patience during my short break last week. I’ve been recovering from surgery and am happy to be back with your weekly look at what’s happening in the Florida Keys real estate market.

This week’s update comes in two parts — new listings and recent sales — so let’s dive right in.

🏡 New Listings

There were 65 new listings added to the MLS this past week, with prices ranging from $319,000 to $3,500,000.
It’s worth noting that a few of these “new” listings are actually properties that were re-entered into the MLS to appear fresh — a common tactic in our market.

Among the standout new entries is a rare listing on coveted Cook’s Island, a true Keys gem for those who crave privacy and waterfront tranquility.

Click here to see the new listings

💰 Recent Sales

On the sales side, we saw 24 closings last week. The highlight? An absolutely stunning oceanfront estate purchased by Barstool Sports founder Dave Portnoy for a record-setting $27,750,000.
This sale is not only headline-worthy but also a strong indicator of continued demand for ultra-luxury properties throughout the Keys.

Click here to see the recent sales

📊 Wrapping It Up

Overall, inventory remains active, with a healthy mix of new and luxury listings making waves across the islands. Whether you’re buying, selling, or just keeping an eye on market trends, the Florida Keys continue to offer some of the most desirable real estate in the country.

Community SpotlightFlorida Keys Real EstateIsland LivingKey HavenKey WestWaterfront Homes October 3, 2025

First Class Fridays: Spotlight on Key Haven

When I first moved to the Keys back in 1987, the very first place I called home was Key Haven. Maybe that’s why this community has always held a special place in my heart. Tucked just outside of Key West, Key Haven has long been one of the most desirable neighborhoods in the Lower Keys—and for good reason.

Why Key Haven is So Special

Key Haven blends the best of island living with convenience. Imagine stepping out your back door and being just minutes from open water—perfect for boaters, anglers, and anyone who loves the sea breeze. At the same time, you’re only a short drive to downtown Key West, which means you can enjoy all the dining, shopping, and cultural experiences without sacrificing peace and quiet at home.

The Community Feel

One of the things I loved most when I lived there was the sense of neighborhood. Key Haven is made up of waterfront and dry lot homes, many with direct boating access. You’ll see neighbors out walking dogs, kids riding bikes, and folks waving as they head out for a sunset cruise. It’s upscale yet laid-back—the quintessential Keys lifestyle.

A Timeless Choice

Even decades later, Key Haven continues to be in high demand. The combination of its location, waterfront opportunities, and community charm makes it timeless. For anyone looking to be close to Key West but still enjoy a little more space and tranquility, Key Haven checks all the boxes.

For me, it will always be more than just a neighborhood—it’s where my Keys story began. 💛

Take a look at what’s available in this great Keys community.

Florida KeysFlorida Keys Real EstateFlorida Keys WeatherHurricane ConditionsIsland Livingweather October 2, 2025

Florida Keys Weather: Frost-Free, Fun, and a Little Feisty

One of the biggest reasons people love the Florida Keys? The weather. It’s the stuff vacation dreams are made of.

No Frost Allowed

Here’s a fun fact: the Keys are the only frost-free spot in the continental U.S. That means no scraping ice off windshields, no frozen toes, and no dead tropical plants. Your flip-flops are safe all year long.

Sunshine on Speed Dial

Most days, the forecast reads something like this: “Sunny with a chance of paradise.” Warm breezes and colorful sunsets are pretty much our brand. Locals know—it’s tough to stay grumpy when the ocean sparkles like that.

But Hold the Halo

Now, let’s be real. It’s not always perfection. Summers can feel like you’re walking through soup. Afternoon storms show up out of nowhere, dump a bucket of rain, and then disappear like nothing happened. And yes, humidity has a permanent residence here.

Hurricanes and Other Hazards

We can’t skip the big one—hurricane season. From June to November, locals keep a weather eye on the tropics. Most storms pass us by, but preparedness is part of the Keys lifestyle. Think of it as island survival skills 101.

Worth the Trade

So, what do we get in return? No frost. No shoveling snow. No gray, endless winters. Instead, we get sunshine, salty breezes, and weather that keeps us outdoors almost every day of the year. Sure, the Keys throw in a little drama now and then—but hey, that’s island life.

Community SpotlightFlorida KeysFlorida Keys HistoryFlorida Keys Real EstateFlorida Keys Real Estate MarketIsland LivingKey WestProperty Spotlight October 1, 2025

The 10 Most Prestigious Homes in Key West

When you think of Key West, you probably picture turquoise waters, swaying palms, and historic cottages. But tucked into this island paradise are some of the most prestigious single-family homes in the Florida Keys. These properties aren’t just houses—they’re retreats, status symbols, and income-generating investments rolled into one.

If you’ve ever wondered what the top tier of Key West real estate looks like, here’s your guide to the ten most exclusive homes currently on the market. 👉 View the full list here.

Spotlight: 1014 Southard Street, Old Town

Among the island’s most impressive properties, 1014 Southard Street is a rare jewel that combines rich history with modern upgrades.

Highlights

  • 4 bedrooms, 3.5 bathrooms

  • Over 3,000 sq. ft. of living space

  • Separate guest cottage with private entry

  • Saltwater pool + tropical gardens

  • Smart home features throughout

  • Tesla charging station + 2023 generator

Built in 1899 by William Cash, this estate exudes historic charm while offering all the comforts of modern living. Its classic design includes dark green shutters, French doors, and cranberry cut-glass transoms, while inside, reclaimed hardwood floors and Blue Castle Limestone bring warmth and sophistication.

The master suite is a sanctuary on the ground level, with a private den, library, and spa-like ensuite. French doors open directly to the pool and lush gardens. Upstairs, two bedrooms share a bath and veranda, while the detached guest cottage offers cathedral ceilings, a built-in bar, and its own poolside deck—perfect for entertaining or hosting guests.

Modern features include Zigbee smart lighting, Ecobee thermostats, an Eero mesh Wi-Fi system, Nest sensors, and advanced security. Off-street parking, a Tesla charging station, and a brand-new generator add convenience to this already exceptional home.

Why It Stands Out

While Key West’s top homes all boast luxury, 1014 Southard Street is special because it blends historic elegance with today’s cutting-edge comforts. It’s rare to find a home in Old Town that has been so thoughtfully restored and updated while preserving its timeless character.

Final Thoughts

The most prestigious homes in Key West aren’t just real estate—they’re a way of life. From waterfront estates with private docks to lovingly restored Victorians, each property offers something unique.

But if you’re looking for a residence that captures the best of both past and present, 1014 Southard Street stands as a shining example of Key West living at its finest.

👉 Curious about the rest? Explore all ten of Key West’s most exclusive homes here.

Spotlight listing provided courtesy of Suzanne Moore, of Suzanne Moore Real Estate

Florida Keys EcosystemFlorida Keys Real EstateFlorida Keys Real Estate MarketGreat Florida ReefIsland LivingLifestyle September 30, 2025

Eco-Friendly Homeownership in the Florida Keys: Protecting Paradise One House at a Time

The Florida Keys are more than just a chain of islands—they’re home to one of the most delicate ecosystems in the world. From our coral reef that acts as a protective barrier, to the freshwater we import and carefully conserve, to the endangered Key Deer that wander Big Pine, every piece of this environment is part of the charm that drew us here in the first place. And yet, many long-term locals worry: are we loving the Keys to death?

As homeowners, we play a critical role in protecting this fragile paradise. Here are some ways Keys residents can live sustainably while still enjoying the lifestyle that makes our islands unique.

1. Water: Our “Liquid Gold”

Freshwater in the Keys is scarce, expensive, and often piped in from the mainland. Simple choices—like installing low-flow fixtures, using rain barrels for irrigation, and xeriscaping with native plants—can make a big difference. Every gallon saved is a step toward preserving what many residents call “liquid gold.”

2. Landscaping the Native Way

The Keys aren’t meant for lawns of thirsty grass and imported ornamentals. By choosing native species like mangroves, sea grapes, or firebush, homeowners can cut down on watering, provide food for native wildlife, and resist pests naturally. Plus, native landscaping helps fight erosion and protects against storm surge.

3. Solar Energy and Sustainable Power

The sunshine that warms our waters can also power our homes. Installing solar panels not only reduces reliance on fossil fuels but also helps lower utility bills in the long run. Even small steps, like solar water heaters or outdoor solar lighting, can have a meaningful impact.

4. Protecting Our Coral Reef

Our coral reef is dying from warming waters, pollution, and overuse. As homeowners, we can help by choosing eco-friendly cleaning products, maintaining septic systems properly, and ensuring stormwater runoff doesn’t carry chemicals into our canals and ocean. What happens in your backyard can ripple all the way to the reef.

5. Being Good Neighbors to Wildlife

Key Deer, sea turtles, manatees, and countless species call the Keys home too. Homeowners can reduce nighttime lighting near beaches during turtle nesting season, drive carefully through wildlife zones, and avoid feeding wild animals. Thoughtful construction and slower traffic literally save lives.

Living in the Keys Means Stewardship

The Florida Keys aren’t just a place to own a home—they’re a responsibility. As development and traffic increase, locals often say the environment and ambiance that brought us here in the first place are being destroyed. The truth is, the Keys can remain paradise only if we protect it.

Eco-friendly homeownership isn’t just about lowering bills—it’s about preserving the natural beauty and delicate balance of our islands for the next generation of dreamers, boaters, divers, and families who fall in love with the Keys.

Because here in the Florida Keys, paradise isn’t just where we live. It’s what we must protect.