Top Islamorada Neighborhoods to Buy Real Estate in 2025 | Buyer’s Guide from a Local Expert

Buying in Islamorada: Neighborhoods Explained by a Local Real Estate Expert

Thinking about buying real estate in Islamorada? Explore the best neighborhoods in this Florida Keys paradise with expert insight into each area’s lifestyle, home values, and investment potential.

Why Buyers Are Drawn to Islamorada

Known as the Sportfishing Capital of the World, Islamorada is a luxury coastal destination nestled in the Upper Florida Keys. Buyers come here for the boating, the relaxed lifestyle, and the rare chance to own waterfront property with character. But choosing the right neighborhood—especially for those new to the area—can be overwhelming.

This guide breaks down Islamorada's key neighborhoods by mile marker, giving you a clear sense of direction as you move from north to south along the famous Overseas Highway (US-1). Whether you want walkability, dockage, or an income-generating investment, you’ll find it below.

Understanding the Difference: Plantation Key vs. Tavernier (MM 91–87)

One of the most common questions I get from buyers is:
“What’s the difference between Tavernier and Plantation Key?”

It’s a great question—because while they’re geographically side by side and often grouped together, there are a few key distinctions that matter when buying real estate.

Plantation Key (MM 90–87) is officially part of the Village of Islamorada, offering a blend of canal front neighborhoods, residential streets, and close proximity to Plantation Key School. Popular neighborhoods here include Plantation Lake Estates, Plantation Shores, and Plantation Key Colony. Municipal services, zoning, and permitting fall under the Village of Islamorada, which may affect future building or renovation plans.

Tavernier (MM 91–88), on the other hand, is unincorporated Monroe County, meaning it falls outside Islamorada’s jurisdiction. While not technically part of Islamorada, it's often considered part of the “greater Islamorada area” due to its lifestyle and proximity. Tavernier offers a more classic Keys vibe with charming conch-style homes and neighborhoods like Hammer Point, Blue Harbor, and areas near Tavernier Creek. It’s also home to Mariners Hospital and Tavernier Towne Center, making it a convenient choice for full-time residents.

• 💡 Local Tip: While Tavernier may not fall within Islamorada’s legal boundaries, locals and even most real estate platforms treat it as part of the Islamorada lifestyle. It shares the same waters, boating culture, and island energy—making it a top choice for buyers who want the feel of Islamorada without the price tag. Living in the Florida Keys: Pros and Cons

1. Plantation Key (MM 90–87)

Best for: Families, Schools, Larger Homesites

Plantation Key is a favorite among year-round residents for its family-friendly atmosphere, deepwater canals, and excellent access to schools and services. It's the ideal blend of laid-back Keys living with functional infrastructure for daily life.

• Waterfront options: Yes, especially in neighborhoods like Plantation Lake Estates
• Zoning: Governed by Islamorada Village
• Proximity to schools and parks: Excellent
• Investment potential: Strong for long-term rentals and resale

2. Tavernier (MM 91–88)

Best for: Value buyers, Old Florida charm, and convenience

Tavernier offers slightly more accessible pricing and a relaxed, residential feel that long-time Keys locals love. It’s known for its marina access, smaller neighborhoods with character, and proximity to essential services.

• Home styles: Conch cottages to updated canal homes
• Notable neighborhoods: Hammer Point, Blue Harbor, Tavernier Oceanside
• Vibe: More local, less touristy, near many restaurants stores and businesses.
• Bonus: Fast access to grocery stores, CVS, and hospital

📍 Check homes for sale in Tavernier here.

3. Upper Matecumbe Key (MM 84–81)

Best for: Walkability, dining, boutique shopping

This area is often called the "downtown" of Islamorada, offering walkable access to the Morada Way Arts District, local marinas, and world-class dining like Pierre’s and Morada Bay. It’s perfect for buyers who want to experience Islamorada's cultural and culinary scene without sacrificing water access.

• Home types: Upscale condos, canal homes, bungalows, large estate homes
• Vibe: Artistic, walkable, and social
• Ideal for: Second-home buyers and lifestyle seekers

✨ Live in the heart of Islamorada—see listings here.

4. Indian Harbor / Venetian Shores (MM 86–85.5)

Best for: Boaters, luxury waterfront homes, quick ocean access

Venetian Shores and neighboring Indian Harbor are some of the most boating-optimized neighborhoods in the Upper Keys. Featuring deepwater canals and immediate access to both ocean and bay via Snake Creek, these homes are ideal for large boats, and serious fishing enthusiasts.

• Homes: Large, luxury homes with docks, lifts, and pools
• Canal access: Among the best in the Keys
• Buyer profile: High-end boaters and waterfront investors, great monthly rental income

⚓ Explore listings in Venetian Shores and nearby here.

5. Lower Matecumbe Key (MM 78–73)

Best for: Luxury buyers, privacy, bay & oceanfront estates

Lower Matecumbe Key is known for its exclusive, low-density atmosphere and prestigious waterfront homes. With wide canals, white sand community beaches, and neighborhoods like Port Antigua and White Marlin Beach, it's a dream location for high-net-worth buyers and second-home seekers.

• Home styles: Custom estates, canalfront homes, and beachfront retreats
• Water access: Exceptional, with private boat ramps and beaches
• Rental potential: High, especially in weekly rental zones
• Best for: Buyers seeking privacy and prestige

🔗 Explore Lower Matecumbe Key real estate here.

Why Buying in Islamorada Is a Smart Investment

Islamorada continues to attract second-home buyers, retirees, and investors due to:

• 📈 Strong appreciation: Limited inventory keeps prices rising
• 🛥️ Lifestyle appeal: Marinas, art, world-class fishing
• 🏝️ Scarcity: Strict zoning and building limits protect long-term value
• 💰 Vacation rental demand: Especially strong for monthly and seasonal rentals, offer some but few weekly rental properties.

Whether you’re looking to live full-time or generate passive income, Islamorada offers incredible long-term upside.

Map Your Move: Understanding the Mile Markers

The Mile Marker (MM) system helps buyers navigate the Keys. As you move south from Key Largo to Key West, here’s how the neighborhoods line up:

• MM 91–88: Tavernier (unincorporated Monroe County)
• MM 90–87: Plantation Key (part of Islamorada)
• MM 86–85.5: Venetian Shores & Indian Harbor
• MM 84–81: Upper Matecumbe Key
• MM 78–73: Lower Matecumbe Key

Each mile marker represents a shift in vibe, lifestyle, and often price point. I’ll help you make sense of which is best for your goals.

Ready to Buy in Islamorada?

Whether you're buying your dream waterfront home or making an investment in one of the most sought-after markets in the Florida Keys, having the right local agent matters. Check out my Ultimate Buying Guide in the Florida Keys if this lifestyle is calling your name!

As a fourth-generation Florida Keys native and full-time real estate expert, I bring unmatched insight into each neighborhood’s nuances, market timing, and hidden opportunities.