Islamorada Real Estate

Waterfront Estates

Islamorada Real Estate

Canal-front estates, oceanfront bluffs, bayside retreats. Islamorada offers the most sought-after waterfront addresses in the Florida Keys — with deep-water canal access and world-class boating and fishing at your doorstep.

By Neighborhood

Islamorada’s Best Waterfront Neighborhoods

Every neighborhood offers a different boating experience. The right canal depth for your vessel is the first decision. Here’s how they compare.

Venetian Shores deep water canal Islamorada
Upper Matecumbe Key

Venetian Shores

100-foot-wide deep-water canals. Direct Atlantic and Florida Bay access via Snake Creek. Top choice for serious boaters with large vessels. $3M–$12M.

Explore Venetian Shores →
Port Antigua Islamorada canal community
Lower Matecumbe Key

Port Antigua

Protected canal entries, HOA beach park on the Atlantic, and a community boat ramp. Coveted for its deep access and neighborhood feel. $2.5M–$9M.

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Oceanfront estate Islamorada Florida Keys
Windley Key & Tea Table

Oceanfront Bluffs

Rare true oceanfront with private beaches and dramatic Atlantic views. The most sought-after addresses in the Keys. $8M–$50M+.

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Bayside home Islamorada with sunset views
Florida Bay Side

Bayside Retreats

Calm flats-perfect water and the Keys’ most spectacular sunsets. Ideal for backcountry fishing and paddling access. $1.8M–$7M.

Explore Bayside Homes →
Before You Buy

What Every Islamorada Buyer Should Know

ROGO building limits, flood insurance realities, dock permitting, canal depth vs. vessel size — the Florida Keys have unique complexity that makes specialist knowledge essential.

Read the Buyer’s Guide
Key Facts
  • Canal-front: $1.8M–$12M by width & access
  • Oceanfront bluffs: $8M–$50M+
  • ROGO strictly limits new construction
  • Flood insurance: verify elevation cert first
  • Dock rights transfer with property
Find Your Islamorada Agent

Work With a Local Waterfront Specialist

Gold Peach Realty’s referral network matches you with the most experienced Islamorada agents — specialists who know the canals, the flood zones, and the off-market inventory.

(770) 283-1223

Looking for homes in North Georgia? Visit Gold Peach Realty at goldpeachrealty.com — your local experts in Dahlonega, Gainesville, and the surrounding mountain communities. Call (770) 283-1223.