Megan Gaylord Realtor

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Megan Gaylord Realtor

📍 Florida Keys + South Florida Real Estate
🌴 Buy • Sell • Invest
🌊 Listings, Local Insight + Coastal Living
☀️ Work With Me | megangaylord.com

03/13/2026

Thinking about life in the Florida Keys? 🌴
Here’s a little preview: seafood festivals, concerts, boat races + parades, and some of the most vibrant holiday celebrations anywhere!

This is your local’s guide to the biggest annual events in the Florida Keys. Save this for later so you don’t miss the fun!

🍤
• Marathon Community Park | Sat + Sun, Mar 14th - 15th (All Day)

🍷
• Truman Waterfront | Mon, Mar 23rd (6-9 PM)

🏃🏼‍♀️
• West Side 7 Mile Bridge | Sat, Apr 11 (6:45 AM)

🎣 FL Keys Lionfish Derby + Arts Festival by
• Captains Meeting/Team Check-In | Sharkey’s Sharkbite Grill | Thur, Apr 23rd (5 PM)
• Arts Festival at REEF Campus Key Largo | Sun, Apr 26th (12-4 PM)

🪕
• Multiple Locations (KW) + Times | Wed, Apr 29th - Sun, May 3rd

🎆 4th of July Celebration by and
• Marathon HS to Sombrero Beach | Patriotic Parade (11 AM)
• Sombrero Beach | Fireworks (9 PM)

📖
• Multiple Locations (KW) + Times | Tues, Jul 21st - Sun, Jul 26th

🍹
• Multiple Locations (KW) + Times | Wed, Aug 12th - Sun, Aug 16th

🍻 by +
• Multiple Locations (KW) + Times | Tent. Thurs, Sept 3rd - Monday, Sept 7th (Labor Day Weekend)

🪅
• Multiple Locations (KW) + Times | Fri, Oct 16th - Sun, Oct 25th

🚤 Powerboat Races
• Multiple Locations (KW) + Times | Sun, Nov 1st - Sun, Nov 8th

🎬
• Multiple Locations (KW) + Times | Sun, Nov 11th - Sun, Nov 15th

🎄Lighting of the Bight: Harbor Walk of Lights
• | Fri, Nov 27th (5 PM)
• Enjoy Lights Nightly through N.Y.E.

🌲 House Annual Christmas Tree Lot
• MARC House, 1401 Seminary St, KW | Fri, Nov 27th (9 AM-7 PM, Daily)

🎅🏼 Key West Hometown Holiday Parade
• Duval St, KW (beginning at Truman Ave and White St) | Sat, Dec 5th (7 PM)

Continued in comments…

02/26/2026

Life’s too short not to live on the water. 🌅
Looking for an updated Big Pine Key retreat, ready to entertain, with boating access in the back yard? This is the place!

1672 Pandorea Lane ☀️
Listed at $799,000
Open this Sunday (3/1) from 11-1
Call/Text me for details: 352-601-5890

01/24/2026

Kicking off a new series, featuring my favorite small businesses, island by island! ☀️

These are the local spots we love, revisit again and again, and always take friends to when they’re in town; the places that truly make the Keys feel like home.

First stop: Key West ⛵️ Swipe through for a few must-visit spots, and follow to keep exploring the Keys with me!

🌴
• 1203 Duval St, KW
• 305-900-8303
• keywestpottery.com

🌴
• 632 Olivia St, KW
• 305-204-4762
• littlepearlkeywest.com

🌴
• 1128 Duval St, KW
• 305-780-7225
• bellalaineart.com

🌴
• 207 Petronia St 101, KW
• 305-296-7691
• santiagosbodega.com

🌴
• 612 Fleming St, KW
• 305-419-4877
• keywestyogasanctuary.com

🌴
• 0 Duval St, KW
• 305-295-7017
• oceankey.com

🌴
• 1114 Truman Ave, KW
• 774-627-8703
• cupcakesushi.com

01/18/2026

It might look like I've got a green thumb, but really it’s just Keys living. 🌞🌺

My mornings start with coffee on the porch, a quiet canal view, and orchids often in full bloom. Living here almost feels like cheating when it comes to keeping plants happy, year-round sunshine and warm ocean air do most of the work.

Feeling grateful for these slow, simple moments. Happy Sunday, y’all. 😌 Follow for more everyday magic in the Keys.

01/12/2026

There’s just something about an intentional workspace. 😌

I don’t know about you, but I work so much more efficiently in a space that’s organized and inspiring. Clean desk, clear mind. 🪷

Working from home isn’t for everyone, but for me it minimizes outside distractions and supports my most focused, consistent work.

This desk reset feels symbolic for 2026, a reminder that some of the most important progress happens quietly, behind the scenes, long before it’s visible. But quiet growth still counts.

Last year felt like a lot of invisible progress. This year is about building on all of that with clarity and momentum.

And yes… the workday officially starts once Griff 🐾 settles in next to me.

Here’s to fresh starts, focused days, and seeing the results of the work already in motion.

09/05/2025

Morning coffee with a sunrise view? This is the place! ☕️🌅This Tropical Bay Estates home was fully remodeled in 2020 and the views are the focal point. Light-filled living areas, a chef’s kitchen, and a backdrop of Bogie Channel where the Atlantic and Gulf are just minutes away. ☀️

Listed by Anneliese Dietrick for $1,399,000

📱Call/text for more info or to schedule a showing: 352-601-5890

09/04/2025

Looking for a tranquil Florida Keys home surrounded by nature? 🌿🦌

This is the lowest-priced, stilted 3-bedroom in Big Pine Key, and it’s tucked right in the heart of Key Deer country. Walkable to the Blue Hole, the Watson and Mannillo Nature Trails, and bike paths that wind through the island. Plus, you’re only minutes from the Eden Pines boat ramp for quick access to the Gulf and Atlantic waters. Fresh updates, sunrise and sunset decks, and plenty of room for parking and trailer storage make this a must-see property.

Watch til the end… some of Big Pine’s cutest locals decided to crash my open house. 😍🦚

📍 2421 Pensacola Rd, Big Pine Key
Listed by the Patti Nickless Group for $565,000

08/08/2025

✌ Awesome Big Pine Key listings to see TOMORROW + SATURDAY!

🌴 29153 Cedar Drive, Big Pine Key — Listed by Anneliese Dietrick, reduced to $899,000! Move-in ready on a fenced ¼-acre with boat lift and access to Pine Channel, Back Country + the Atlantic. Open Fri (8/8) • 11–1

🦌 2421 Pensacola Rd, Big Pine Key — Listed by The Patti Nickless Group, asking $565,000! In the heart of the National Key Deer Refuge, this 3BR offers peace, privacy + plenty of space. Open Sat (8/9) • 11–1

Can’t make it? Call/Text 352-601-5890 for details or a private tour.

07/18/2025

T O M O R R O W (7/19) Join me for an open house in Big Pine Key at 2421 Pensacola Road from 11am - 1pm! Nestled in the heart of the National Key Deer Refuge and just a short walk to nature trails, the Blue Hole and a short drive to town, this recently updated 3-bedroom home offers tranquility and convenience with modern comforts! Listed by the Patti Nickless Group, asking $565,000🌴

📸: Salty Orchid Photography

06/09/2025

🌴Open House Today | 11AM–1PM
📍 29559 Ranger Ave, Big Pine Key

Canal-front slice of paradise in Pine Channel Estates! No-bridge access to the Gulf and a quick boat ride to the Atlantic and world-class fishing and diving; 75' concrete seawall with 16K boat lift + davits! Inside, enjoy an open-concept living space ideal for entertaining, offering a spacious kitchen, and large deck overlooking the water. Two spacious bedrooms, with additional storage space downstairs, and a permitted 2-car garage! Tranquil living just minutes from town — come see it today!

04/17/2025

Big Pine Key Open House this S A T U R D A Y ! Hope to see you there. 😊

04/04/2025

Big Pine Key open house T O M O R R O W from 11-1 at 29737 Newfound Blvd! This fantastic property is updated with partial Open Water Views in front, and serene canal views in back! No-bridge access to the Atlantic, and just minutes to world famous fishing! See you there.☀️

Address

29967 Overseas Highway
Big Pine Key, FL
33043

Telephone

+13526015890

Website

http://megangaylord.com/

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