Neighborhood Guide
Waterfront Communities of
the Upper Florida Keys
Each Keys neighborhood has its own character, community, and market. Whether you're searching for waterfront homes in Key Largo, waterfront homes in Islamorada, or canal-front properties in Tavernier, this guide gives you an insider's look at the communities Jaclyn Kelley and The Jaclyn Kelley Group know best — from boating access and dock conditions to market pricing and flood zone details. With 21 years serving these communities, Jaclyn leads the team that is the go-to expert for understanding what makes each one unique.
The First of the Keys
Key Largo
- Deep-water canal communities
- Ocean access properties
- Close to John Pennekamp State Park
- Diverse dining and shopping
- Active marina community
Key Largo is the gateway to the Florida Keys — the largest and most populous of the Upper Keys. This vibrant community offers a mix of waterfront estate, canal-front homes, and oceanfront properties. With multiple boat ramps, marinas, and world-class diving at John Pennekamp Coral Reef State Park, Key Largo attracts buyers who want both waterfront access and an active community. Home prices in the waterfront market typically range from $1.5M to $5M+.
Ask about Key LargoSportfishing Capital of the World
Islamorada
- World-class sportfishing
- Stunning sunset views
- Upscale waterfront estates
- Art galleries and fine dining
- Beach access at Anne's Beach
Islamorada is known worldwide as the sportfishing capital, but it is so much more than that. This Village of Islands offers some of the most exclusive waterfront properties in the Upper Keys, with stunning ocean views, pristine beaches, and a refined yet relaxed dining scene. Sunset views here are legendary. The market features high-end waterfront homes, luxury condos, and boutique investment properties, with waterfront prices often in the $2M–$8M range.
Ask about IslamoradaQuiet Waterfront Charm
Tavernier
- Affordable canal-front options
- Family-friendly community
- Local marina and boat ramps
- Central Upper Keys location
- Less tourist traffic
Tavernier sits between Key Largo and Islamorada and offers a quieter, more residential character. Canal-front homes here tend to be more value-oriented, making it popular with families and buyers seeking a laid-back Keys lifestyle. The community has its own marina, local restaurants, and easy access to both Key Largo and Islamorada. Waterfront homes typically range from $1M to $3M.
Ask about TavernierDeep-Water Canal Community
Port Largo
- Deep-water canal access
- Direct ocean access available
- Active boating community
- Strong property values
- Established neighborhood
Port Largo is one of the most sought-after canal communities in Key Largo, known for deep-water canal access popular with boaters. Many homes offer direct ocean access, making it ideal for sailors and sportfishermen. The neighborhood has a strong sense of community with neighbors who share a love of the water. Properties here consistently hold strong resale value.
Ask about Port LargoExclusive Waterfront Enclave
Indian Harbor & Waterways
- Wide deep-water canals
- Premium dock access
- Quiet upscale setting
- Well-maintained homes
- Strong boating infrastructure
Indian Harbor and the Indian Waterways represent some of the most exclusive waterfront living in the Upper Keys. These communities feature wider canals, premium dock access, and well-maintained homes in a quiet, residential setting. Buyers who prioritize boating access and a peaceful, upscale neighborhood often gravitate here.
Ask about Indian Harbor & WaterwaysIsland Living with Ocean Views
Venetian Shores
- Wide-water ocean views
- Elevated modern construction
- Island community feel
- Close to Islamorada dining
- Resort-style residential setting
Venetian Shores is an upscale island community in Islamorada offering wide-water views and a distinctly tropical atmosphere. Homes here often feature elevated construction, modern amenities, and panoramic ocean or bay views. The neighborhood appeals to buyers seeking a resort-like residential experience in the heart of the Upper Keys.
Ask about Venetian ShoresCanal-Front Living on Plantation Key
Plantation Key Colony
- Canal-front homes with boat lifts
- Waterfront homeowners park
- Direct access to Florida Bay
- Boat dock access
- Quiet residential setting
Plantation Key Colony is a canal-front community on Plantation Key in Islamorada, situated near mile marker 90 on the Gulf side of the Overseas Highway. Many properties feature boat lifts and private docks with access to Florida Bay and the Atlantic. The neighborhood includes a waterfront homeowners park and attracts buyers who value a quiet, boating-oriented lifestyle within Islamorada.
Ask about Plantation Key ColonyBoating Community in Key Largo
Taylor Creek Village
- Community boat ramp
- Waterfront amenities
- Boat trailer storage
- Strong community association
- Convenient Upper Keys location
Taylor Creek Village is a boating-oriented community in Key Largo near mile marker 104.5. Residents enjoy a boat ramp, waterfront chickee hut, boat trailer storage, and a strong sense of community. The neighborhood appeals to buyers who prioritize direct water access and a casual, Keys lifestyle in a tight-knit setting.
Ask about Taylor Creek VillageWhich Community Is Right for You?
Every neighborhood has a different feel, price point, and lifestyle. I'd love to help you explore which one fits your vision — whether you're buying, selling, or just curious.