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Waterfront Knowledge. Keys Lifestyle.

Led by Shane Wilson, the Shane “Waterfront” Wilson Team specializes in waterfront and luxury real estate throughout the Florida Keys. Backed by generations of local roots and decades of boating and waterfront expertise, the team provides trusted guidance, strategic marketing, and unmatched insight into the Keys lifestyle.

Modern white two-story home with large windows, palm trees, and a landscaped entry.

Buy a Home
Tall palm tree with arching fronds against a blue sky and scattered clouds.

Sell a Home
Modern living room with a white sectional and floor-to-ceiling windows overlooking turquoise water.

Contact Us

members of and referral partners with who's who in luxury real estate

Shane Wilson stands at a motorboat’s helm, with open water behind him.

Get To Know Us

The Shane “Waterfront” Wilson Team brings together deep local knowledge, waterfront expertise, and a passion for helping clients find their place in the Florida Keys. From oceanfront estates and canal homes to vacation retreats and investment properties, the team delivers a personalized experience rooted in authentic local insight.

Known for their understanding of boating access, waterfront property nuances, and the unique lifestyle the Keys offer, the team helps buyers and sellers navigate every step with confidence, professionalism, and care.

Known for their professionalism, responsiveness, and strong understanding of waterfront living, the team is committed to creating a seamless experience while helping clients make confident, informed real estate decisions.

Meet the Team Contact Us
What Our Clients Say

He is not only a professional realtor but a dutiful representative of the greater Fort Myers area. Shane has a wealth of knowledge of the waterways throughout South Florida. I highly recommend Shane to all of my friends when looking for a home in Southwest Florida.

— Buyer & Seller

What Our Clients Say

Made buying a house an easy and pleasurable experience. His assistance and local knowledge came to the rescue time and time again. He always had time for even the smallest of details and truly seemed to care about his customers. Because of his prior experience and knowledge of inventory, we were able to find the right house quickly and efficiently, and his assistant was always available to answer questio...

— Joules

What Our Clients Say

Wow! What an outstanding agent Shane turned out to be. He found just the right house and has jumped through so many hoops to help make this dream a reality. I highly recommend Shane and his wonderful team.

— Ariell P.

What Our Clients Say

We couldn't be more satisfied with Shane Wilson. He has all the attributes of a fine Realtor. He is professional, courteous, and knowledgeable. Shane goes out of his way to make you feel comfortable from the listing to the closing and stays involved personally during the entire process. If a question, you can call him directly and he'll answer. We would not hesitate to recommend Shane to anyone who is th...

— L. C.

What Our Clients Say

Shane and his group are the best! Shane found exactly what we were looking for. He got "us". You will be treated like a friend, not a payday. From the first phone call through to closing, everything was a breeze.

— Todd F.

What Our Clients Say

Call this man, he's one of the best agents I've ever dealt with. He helped us find a fabulous home in Cape Coral. He gave us great advice on a host of service people. As Canadian buyers, we couldn't have anyone with more knowledge and resources for our purchase.

— Tuffy M.

What Our Clients Say

Shane grew up in the Keys and is an outdoorsman who involves his whole family, so he has a very broad perspective of this area and lifestyle. His referrals for all the details that go into a new home in a new area are first-class in quality, service, and competitive rates. He is patient and helpful and will work hard to find you a good fit for what you are looking for.

— Simmon M.

What Our Clients Say

Shane has the rare gift of advising you like a friend and not a salesman. He listens to what you want in a home, and what you don't, and helps guide you to the right fit. He is very knowledgeable about the area and helped us make the right decision for our family. We love our new home, and love the area he helped us choose. When you are with him, you are his priority, meaning he doesn't spend all his tim...

— Buyer

What Our Clients Say

Shane is extremely knowledgeable in selling homes. We were always comfortable with his advice. He is professional and truly wants to sell your home. We would definitely recommend and use him again.

— James A.

What Our Clients Say

Can’t recommend Shane and his team enough! You will not be disappointed as he is the hardest-working realtor in the business. They are caring and realize that your purchase is a life changer. I have had dealings with Shane over the years, and it’s always been nothing less than professional. Shane has a way of making all his customers feel comfortable and welcomed. There is no other realtor in SW Florida ...

— Bill H.

What Our Clients Say

Shane and his team have been outstanding. He drove us around for days trying to find the perfect home. His responsiveness (even while on vacation) and attentiveness are stellar. I highly recommend him!

— Heather S.

What Our Clients Say

Shane and Anne were just as vested in the success of our family finding the right property for our lifestyle as we were! We saw an unusual number of homes in 2 days, and found the best option for our family!

— Cassandra B.

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Featured Properties

For Sale

Waterfront home with a pool and dock beside a mangrove-covered island and canal.
$4,999,999

1590 Pelican, Marathon, FL 33050

  • 5 BEDS
  • 5 BATHS
  • 3,346 Sq.Ft.

For Sale

Aerial view of a waterfront home with a pool, palm trees, and boats docked beside it.
$4,445,000

136 San Remo Drive, Plantation Key, FL 33036

  • 8 BEDS
  • 4 BATHS
  • 4,681 Sq.Ft.

For Sale

Aerial view of a modern waterfront home with a pool, tropical landscaping, and boats at its private dock.
$3,595,000

362 E Seaview Drive, Duck Key, FL 33050

  • 4 BEDS
  • 4 BATHS
  • 3,479 Sq.Ft.

Active Under Contract

Aerial location graphic with a red arrow pointing to a site near Overseas Highway, Friendship Park, and TradeWinds Shopping Center.
$1,295,000

101201 Overseas Highway, Key Largo, FL 33037

For Sale

Aerial view of a canal-side home with a tiled roof, broad lawn, and waterfront homes across the canal.
$985,000

14661 Fair Havens RD, Fort Myers, FL 33908

  • 3 BEDS
  • 2 BATHS
  • 1,940 Sq.Ft.

For Sale

Vacant waterfront lot outlined in red beside homes and marina slips.
$649,000

12110/12112 Siesta DR, Fort Myers Beach, FL 33931

For Sale

Waterfront condominium towers and docks beside turquoise water, with a long bridge in the distance.
$599,000

15021 Punta Rassa RD 403, Fort Myers, FL 33908

  • 2 BEDS
  • 2 BATHS
  • 1,167 Sq.Ft.

For Sale

12755 Brewster DR
$575,000

12755 Brewster DR, Fort Myers, FL 33908

  • 2 BEDS
  • 1 BATH
  • 1,056 Sq.Ft.

For Sale

Beachfront condominium tower with rows of balconies, palm-lined grounds, a pool, and ocean beyond.
$569,900

7500 Estero BLVD 203, Fort Myers Beach, FL 33931

  • 2 BEDS
  • 2 BATHS
  • 1,042 Sq.Ft.

For Sale

White condominium building with balconies, palm trees, and covered parking beneath a clear blue sky.
$294,500

20930 ISLAND SOUND CIR 204, Estero, FL 33928

  • 2 BEDS
  • 2 BATHS
  • 1,207 Sq.Ft.

For Sale

Harbor Grand waterfront condominium towers beside a blue bay, with palm-lined grounds and a bridge in the distance.
$229,900

3000 Oasis Grand BLVD 1206, Fort Myers, FL 33916

  • 1 BED
  • 2 BATHS
  • 867 Sq.Ft.

For Sale

5471 PEPPERTREE DR 7
$227,900

5471 PEPPERTREE DR 7, Fort Myers, FL 33908

  • 2 BEDS
  • 2 BATHS
  • 1,018 Sq.Ft.

For Sale

Waterfront yacht club and marina with boat slips, small boats, and palm-lined docks.
$77,900

15051 PUNTA RASSA RD 528, Fort Myers, FL 33908

For Sale

Waterfront marina building with boat slips, docks, and a boat in the foreground.
$75,000

15051 PUNTA RASSA RD 414, Fort Myers, FL 33908

For Sale

Aerial view of a wooded vacant lot outlined in teal beside neighboring homes and a road.
$68,500

7835 22nd PL, Labelle, FL 33935

For Sale

Waterfront yacht club and marina with boats on lifts, turquoise water, and a multilevel balcony building.
$28,700

15051 PUNTA RASSA #382 RD, Fort Myers, FL 33908

For Sale

Waterfront yacht club marina with turquoise water, boats, docks, and multilevel buildings.
$28,500

15051 PUNTA RASSA RD 508, Fort Myers, FL 33908
View All

How Much is Your Home Worth?

  • Instant property valuation
  • Expert advice
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Florida Keys Neighborhoods

Aerial view of a Florida Keys island community, with a road between turquoise water and marinas.

Islamorada

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Florida Keys waterfront with palm trees, a thatched pavilion, boats, and kayaks.

Key Largo

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Palm-covered islands and boats in turquoise Florida Keys waters beneath a cloud-filled blue sky.

Key West

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Palm-lined sandy shoreline with a thatched hut beside the water at sunset.

Plantation Key

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Aerial view of a palm-lined beach curving beside a coastal neighborhood and turquoise water.

Marathon

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Florida Keys beach with turquoise water, a sailboat, palm trees, and a long bridge.

Big Pine Key

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Explore Our Videos

SW Florida Boating
A dolphin leaps beside a boat’s foamy wake on turquoise water.
Fort Myers Lifestyle Video from the Air to the Sea and Beaches with Shane "Waterfront" Wilson
Man in a pink polo and headset at the controls of a small aircraft.
Alligator Reef Light Chillin
White real estate boat floating in turquoise water near Alligator Reef Light.
Florida Keys real estate promotional graphic with an antique key, Shane Waterfront Wilson Team branding, and luxury real estate tagline.

The Key to LRE® – Cypress Realty

As a luxury real estate leader, Cypress Realty has been hand-selected to represent the Who’s Who in Luxury Real Estate and LuxuryRealEstate.com brands.

Read More

Recent Blog Posts

Man in sunglasses and headphones gestures beside a microphone in a tropical waterfront setting.
How Checking One Nail Saved Over $5,000 a Year on Florida Keys Wind Insurance

A real Florida Keys real estate deal showed how a current wind mitigation inspection and one missing detail (the third nail) dropped wind insurance from $12,000 to $5,… Read more
Man wearing headphones speaks into a microphone at a tropical waterfront table.
The Question I Ask Before I Show You a Florida Waterfront Home - Shane 'Waterfront' Wilson

Before I show a Florida waterfront home in the Keys, Cape Coral, or Fort Myers, I ask what boat you want. Draft, bridge height, and tide decide the neighborhood.

Outdoor pool with a stone waterfall, tropical landscaping, and two lounge chairs on a wooden deck.
Raising kids in the Florida Keys

Stay up to date on the latest Florida community and real estate trends by reading our blogs.

Bright living and dining area with arched windows, tropical greenery, and a round dining table.
Why Health is Your True Wealth: Lessons from a Lifetime of Hustle and Wisdom

Now they’re in their 60s, 70s, even 80s, sitting on piles of cash, but they can’t enjoy it.

Modern white kitchen with a large cooktop island and windows overlooking tropical landscaping.
Best Waterfront Restaurants in Key Largo With Dockage

Want to know which neighborhoods make it easiest to boat to these restaurants?

SW Florida & Florida Keys Waterfront Home Real Estate Expert, Shane Waterfront Wilson
Southwest Florida & Florida Keys Waterfront Homes, Boating & Aviation Expert, Shane 'Waterfront' Wilson in 'Lovin' the Florida Lifestyle': Episode 001

Welcome to the debut episode of Loving the Florida Lifestyle with veteran Florida real estate broker Shane "Waterfront" Wilson. Grounded in Simon Sinek’s "Golden Circl… Read more
Living room with a pale pink sofa, ornate wall paneling, and cane chairs.
Waterfront Wilson Welcomes Newest Team Member

Becoming a real estate agent in the Florida Keys was a role he was born for.

Two men record a podcast at a table on a screened porch.
How We Continue to Sell Multiple Homes Per Month in Southwest Florida & the Florida Keys (Even In Tough Market Conditions)

Learn the power of fast responses, genuine customer care, turning ADHD into a superpower, and building lifelong client relationships.

Waterfront home with a palm-lined pool and several boats docked along the canal.
Big Boats. Big Family. Big Lifestyle. Welcome to 136 San Remo Drive, Venetian Shores

Homes with this kind of size, dockage, and access don’t hit the market often.

Furnished living room with sliding doors opening to a balcony overlooking water and a city skyline.
The Power of Real Estate: Changing Lives, One Closing at a Time

It’s what I’ve seen in those long marriages: beyond the ups and downs, there’s mutual admiration.

Open-plan living room with a dark sectional, modern kitchen, and tropical patio pool.
Kickin’ Off our “Lovin’ the Florida Lifestyle” Podcast – Get Fired Up and Inspired!

Catch you on the next episode – soon we’ll be takin’ these podcasts out in the field!

Oceanfront living room with white sectional sofas, a concrete fireplace, and expansive glass walls.
Port Largo: One of the Best Waterfront Neighborhoods in Key Largo

And when you’re ready to take the next step, reach out. We can tour by land — or by water.

Covered terrace dining area with arched openings, tropical plants, and an ocean view.
Best Waterfront Condo Communities in Key Largo

It’s ideal for buyers who want luxury + flexibility + boating all in one place.

Courtyard patio with a dining table beneath a shade canopy, surrounded by tropical plants.
The Ultimate Guide to Waterfront Condos in Islamorada

Let’s break down a few of the most popular and well-appointed communities.

Aerial view of mangrove-covered waterfront acreage, with homes, docks, and a landscaped island along the shore.
Looking for Acreage in the Florida Keys? This Rare Waterfront Property Might Be the One

3+ acres, deepwater dockage, ocean views, and privacy—this is the one you’ve been waiting for.

Open-plan living room with beige sofas, vaulted ceiling, and adjoining white kitchen.
What to Know Before Buying a Waterfront Property in the Florida Keys

When I tour waterfront homes with clients, I often take them out by boat too.

Open-plan living room with a white sectional, vaulted beam ceiling, and glass doors to a courtyard.
Living the Florida Keys Dream: How My Passion for Waterfront Real Estate Fuels My Everyday Life

Growing up in Florida, real estate wasn’t just a career choice—it was practically in my DNA.

Covered patio with wicker seating overlooking a swimming pool and paved deck.
The Ultimate Guide to Waterfront Condos in the Florida Keys

Affordable waterfront condos with boat slips, resort amenities, and short-term rental ability.

Open-plan living room with a light sofa, dark wood kitchen cabinetry, and tray ceiling.
Waterfront Homes in the Florida Keys – Pricing Your Home in Today’s Market

Recently, I sat down with a wonderful couple whose property wasn’t moving.

Waterfront home with a pool, palm trees, and two boats moored at its canal dock.
Living the Dream in Venetian Shores, Islamorada

It’s measured in sunsets, tight lines, and how quickly you can get from your dock to open water.

Contemporary reception lounge with a gray sofa, black leather chairs, and a wood-front desk.
Your Guide to Key Largo Neighborhoods

Because at the end of the day, finding the right home isn’t just about the house itself.

Furnished living room with a white sofa, wooden coffee table, and large windows overlooking the city.
Key Largo Real Estate Market Update: March 2025

If you’ve been waiting for the right time to jump in, this could be it.

Backyard pool with submerged seating steps beside an aqua glass-enclosed sunroom and furnished deck.
Just Listed: Renovated Old Town Key West Pool Home — 1215 Margaret Street

You’re in the heart of it all, without being stuck in the middle of the buzz.

Living room with vaulted wood-beam ceiling, sliding glass doors, and patio grill.
Islamorada Residential Real Estate Market Update: January 2025

As the sun rises on a new year, so does the real estate landscape in Islamorada.

Open-plan living room with a vaulted wood ceiling, sliding glass doors, and tropical garden views.
How Key Largo’s Growing Inventory Impacts Buyers and Sellers: November 2024

Active listings climbed by 46.4% year-over-year, with 303 homes now available.

Coastal living room with a gray sofa, white coffee table, and upright wooden surfboard.
Fishing, Feasting, and Finding Homes: Shane’s Signature Florida Keys Client Experience

Once the cooler is full, we head straight to one of my favorite waterfront restaurants.

Bright white kitchen with a large island, wooden stools, and stainless steel appliances.
October 2024 Market Update: Florida Keys Townhouses and Condos

Here’s a standout stat: 88.6% of closed sales in October were cash transactions.

Pergola-covered patio with a sectional sofa, coffee table, lawn, tropical plants, and raised hot tub.
Hooked on Islamorada: Your Expert Guide to Waterfront Homes

Not all canals are created equal, though, and here’s where my local expertise comes into play.

Dining area with a round wood table, leafy plants, and a large abstract painting.
At Home

Find something you love to do, and you’ll never have to work a day in your life.

Bright white kitchen with a blue island, stainless steel refrigerator, and wood dining table.
Mini Season Lobstering in the Florida Keys

The United States Coast Guard approached us and asked permission to board our vessel.

Bright entryway with a natural wood door, built-in bench and shelving, and patterned runner rug.
Real Estate Q&A: Creative Mortgage May Be Too Risky

Our credit is not so great, and the seller can’t afford to pay off the existing mortgage.

Modern high-rise living room with floor-to-ceiling windows overlooking the water and city skyline.
We Love Helping People

Both men were raised in the Keys, and not only call it home, but make it their goal to help people.

Furnished waterfront balcony overlooking the ocean, with two cushioned chairs and a round table.
Your Own Slice of Paradise

Making sure people experience “the Keys way of life” is something this talented team does well.

Bright living room with a white sofa, rustic coffee table, gray chairs, and glass doors to greenery.
Selling a Waterfront Home in the Florida Keys

The Florida Keys is not a market where generalist experience translates directly.

View Blog

Let’s Find Your Dream Home

Decades of waterfront expertise, deep local roots, and a passion for the Florida lifestyle define every client experience. The Shane “Waterfront” Wilson combines extensive real estate knowledge with unmatched insight into the Florida Keys and Southwest Florida markets—helping buyers and sellers navigate every step with confidence and ease.

Contact Us

Get In Touch With Our Team

Get in Touch

By providing your contact information to Shane Wilson, your personal information will be processed in accordance with Shane Wilson's Privacy Policy. By checking the box(es) below, you expressly consent to receive marketing or promotional real estate communication from Shane Wilson in the manner selected by you. For SMS text messages, message frequency varies. Message and data rates may apply. Consent is not a condition of purchase of any goods or services. You may opt out of receiving further communications from Shane Wilson at any time. To opt out of receiving SMS text messages, reply STOP to unsubscribe. SMS text messaging is subject to our Terms of Use.
Rocky sandy beach beside calm turquoise water and palm-lined beachfront condominiums.

Contact Details

SHANE "WATERFRONT" WILSON

[email protected]
(239) 851-3861 

ADDRESS ISLAMORADA 85960 OVERSEAS HWY STE 4 ISLAMORADA, FL 33036 FORT MYERS 7270-4 COLLEGE PKWY FORT MYERS, FL 33907