# 16 Avacado Street, Upper Matecumbe Key Islamorada, FL 33036

> **TL;DR:** 9bd/10ba single family, $23,500,000 ($3188/sqft), built 2023, 7,372 sqft.
> Pool, Waterfront, A/C. Est. $125,683/mo. Listed 11 days.

## Property at a Glance

| Attribute | Value |
|-----------|-------|
| Price | $23,500,000 |
| Price/sqft | $3188 |
| Bedrooms | 9 |
| Bathrooms | 9 full, 2 half |
| Square Feet | 7,372 |
| Year Built | 2023 |
| Lot Size | 25,770 sqft (0.59 acres) |
| Property Type | Single Family (Single Family Residence) |
| Status | Active |
| Days on Market | 11 |

## Why This Home Stands Out

- **Pool** - Porch, Patio
- **Waterfront** - Waterfront location listed

## Estimated Monthly Costs

| Category | Amount |
|----------|--------|
| Principal & Interest (20% down, 30-year at 6.5%) | $118,829 |
| Estimated Insurance | $6,854 |
| **Total** | **$125,683** |

## Key Amenities

- Pool
- Waterfront
- A/C

## Property Highlights

- Built in 2023
- 0.59 acre lot
- Private pool
- Waterfront

## Description

### Agent Description
Rarely do the lines intersect between architectural excellence, positioning, thoughtfulness, and elite water access, until now. Set on a private street in downtown Islamorada, this gated bayfront property includes a main house, guest house, sunset views, and 170 feet of dockage. Built above flood, the main house offers 6 bedrooms, 6 bathrooms, 2 half baths, and an office. A pivot front door opens to living spaces overlooking the bay. The formal dining room includes a wet bar and wine cellar, while the kitchen's double islands provide room for preparing meals and gathering. A water vapor fireplace anchors the living room, and ceilings open to the second floor above both the living room and kitchen. A floating staircase and elevator connect the two levels. Two primary suites, one on each floor, offer a choice of setting. Both feature freestanding soaking tubs and bay-facing windows that turn opaque at the touch of a button. A powder room serves the main living area, and a cabana bath is located by the pool. Outside, the infinity pool's swim-up bar and submerged seating meet the outdoor kitchen counter. The gazebo is equipped with roll-down hurricane shades. Along the waterfront, a 70-foot concrete jetty shelters the basin around the beach. An additional 100-foot wood dock provides two boatlifts (30,000 lb & 10,000 lb) and space for visiting boats. Across the front courtyard, the guest house offers independent living space, including 3 bedrooms and 2 bathrooms upstairs. Three air-conditioned garage bays occupy the ground floor. Tropical landscaping chosen for the Keys climate keeps upkeep manageable. A 100 kW standby propane generator serves the entire property, and an organic mosquito misting system helps make the grounds more comfortable. Years of planning and construction come together in a property designed for life on the bay, from everyday living to time spent on the water.

## Location

- **Address:** 16 Avacado Street, Upper Matecumbe Key Islamorada, FL 33036
- **County:** Monroe
- **Neighborhood:** Strattons (82.5)
- **Coordinates:** 24.930005, -80.623746
- **Google Maps:** https://www.google.com/maps?q=24.930005,-80.623746

## Listing Agent

- **Name:** AJ Vetter · **License:** 3296730
- **Brokerage:** Palm House Real Estate
- **Broker Phone:** (305) 304-8841
- **Listing URL:** [View original listing](https://www.realtor.com/realestateandhomes-detail/16-Avacado-St_Islamorada_FL_33036_M66583-40378?f=listhub&s=FLKEYSMLSFL&m=621766&c=propsimple)

## Photos

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---

**MLS#:** 621766 | **Updated:** 2026-10-30
**Source:** listhub

*Copyright © 2026 Florida Keys Board of REALTORS®. All rights reserved. All information provided by the listing agent/broker is deemed reliable but is not guaranteed and should be independently verified.*

[View on PropertySimple](https://www.propertysimple.ai/listing/16-avacado-street-upper-matecumbe-key-islamorada-fl-33036-9ab67ef73f2e46a5af9899cccb4f71fb)

---

## Structured Data

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  "url": "https://www.propertysimple.ai/listing/16-avacado-street-upper-matecumbe-key-islamorada-fl-33036-9ab67ef73f2e46a5af9899cccb4f71fb",
  "name": "16 Avacado Street, Upper Matecumbe Key Islamorada, FL 33036",
  "description": "Rarely do the lines intersect between architectural excellence, positioning, thoughtfulness, and elite water access, until now. Set on a private street in downtown Islamorada, this gated bayfront property includes a main house, guest house, sunset views, and 170 feet of dockage. Built above flood, the main house offers 6 bedrooms, 6 bathrooms, 2 half baths, and an office. A pivot front door opens to living spaces overlooking the bay. The formal dining room includes a wet bar and wine cellar, while the kitchen's double islands provide room for preparing meals and gathering. A water vapor fireplace anchors the living room, and ceilings open to the second floor above both the living room and kitchen. A floating staircase and elevator connect the two levels. Two primary suites, one on each floor, offer a choice of setting. Both feature freestanding soaking tubs and bay-facing windows that turn opaque at the touch of a button. A powder room serves the main living area, and a cabana bath is located by the pool. Outside, the infinity pool's swim-up bar and submerged seating meet the outdoor kitchen counter. The gazebo is equipped with roll-down hurricane shades. Along the waterfront, a 70-foot concrete jetty shelters the basin around the beach. An additional 100-foot wood dock provides two boatlifts (30,000 lb & 10,000 lb) and space for visiting boats. Across the front courtyard, the guest house offers independent living space, including 3 bedrooms and 2 bathrooms upstairs. Three air-conditioned garage bays occupy the ground floor. Tropical landscaping chosen for the Keys climate keeps upkeep manageable. A 100 kW standby propane generator serves the entire property, and an organic mosquito misting system helps make the grounds more comfortable. Years of planning and construction come together in a property designed for life on the bay, from everyday living to time spent on the water.",
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