# 150 List Street, Upper Matecumbe Key Islamorada, FL 33036

> **TL;DR:** land, $4,499,500.
> Waterfront, View. Est. $24,064/mo. Listed 244 days.

## Property at a Glance

| Attribute | Value |
|-----------|-------|
| Price | $4,499,500 |
| Lot Size | 33,977 sqft (0.78 acres) |
| Property Type | Land (Other) |
| Status | Active |
| Days on Market | 244 |

## Why This Home Stands Out

- **Waterfront** - Waterfront location listed
- **Views** - Water

## Estimated Monthly Costs

| Category | Amount |
|----------|--------|
| Principal & Interest (20% down, 30-year at 6.5%) | $22,752 |
| Estimated Insurance | $1,312 |
| **Total** | **$24,064** |

## Key Amenities

- Waterfront
- View

## Property Highlights

- 0.78 acre lot
- Waterfront

## Description

### Agent Description
Discover an extraordinary opportunity to own 34,000 square feet of prime bayfront real estate in one of Islamorada's most coveted and private enclaves. Boasting 100+ feet of pristine bay frontage, this exceptional property captures open water views, serene sunsets, and the essence of the Florida Keys lifestyle. Tucked within the property is a charming ground level 1950s cottage offering one bedroom and one bathroom - ideal for a comfortable interim residence while you bring your custom waterfront vision to life. For boating enthusiasts, the estate offers dockage with direct bay access, placing world-class fishing, sandbars, and crystal-clear waters just moments away. A PERMIT HAS BEEN ISSUED to repair and expand the existing dock and add two boat lifts (20,000 lb and 16,000 lb), significantly enhancing the property's boating capabilities and long-term value. With the existing estate slated for demolition and redevelopment, the conceptual renderings unveil a spectacular 4,872-square-foot custom residence offering five bedrooms, five and a half bathrooms, a three-car garage, and a resort style pool - all thoughtfully designed to capture water views from every vantage point. This remarkable bayfront estate offers endless possibilities in an unparalleled setting.

## Location

- **Address:** 150 List Street, Upper Matecumbe Key Islamorada, FL 33036
- **County:** Monroe
- **Neighborhood:** Strattons (82.5)
- **Coordinates:** 24.924569, -80.629517
- **Google Maps:** https://www.google.com/maps?q=24.924569,-80.629517

## Virtual Tour & Media

- **Video Tour:** https://bcove.video/3ML6hRM

## Listing Agent

- **Name:** Bonnie Ekblom Oliver · **License:** 3186690
- **Brokerage:** Ocean Sotheby's International Realty
- **Broker Phone:** 3057128888
- **Listing URL:** [View original listing](https://www.realtor.com/realestateandhomes-detail/150-List-St_Islamorada_FL_33036_M56418-18064?f=listhub&s=FLKEYSMLSFL&m=618920&c=propsimple)

## Photos

![150 List Street - Photo 1](http://lh.rdcpix.com/8c3031eaeea8927565ddd9f4203d5334l-f1198726027r.jpg)

![150 List Street - Photo 2](http://lh.rdcpix.com/8c3031eaeea8927565ddd9f4203d5334l-f1348255021r.jpg)

![150 List Street - Photo 3](http://lh.rdcpix.com/8c3031eaeea8927565ddd9f4203d5334l-f3411482918r.jpg)

![150 List Street - Photo 4](http://lh.rdcpix.com/8c3031eaeea8927565ddd9f4203d5334l-f9685714r.jpg)

![150 List Street - Photo 5](http://lh.rdcpix.com/8c3031eaeea8927565ddd9f4203d5334l-f3671579448r.jpg)

![150 List Street - Photo 6](http://lh.rdcpix.com/8c3031eaeea8927565ddd9f4203d5334l-f3834228964r.jpg)

![150 List Street - Photo 7](http://lh.rdcpix.com/8c3031eaeea8927565ddd9f4203d5334l-f3265109240r.jpg)

![150 List Street - Photo 8](http://lh.rdcpix.com/8c3031eaeea8927565ddd9f4203d5334l-f3163544369r.jpg)

![150 List Street - Photo 9](http://lh.rdcpix.com/8c3031eaeea8927565ddd9f4203d5334l-f120344394r.jpg)

![150 List Street - Photo 10](http://lh.rdcpix.com/8c3031eaeea8927565ddd9f4203d5334l-f2747870334r.jpg)

![150 List Street - Photo 11](http://lh.rdcpix.com/8c3031eaeea8927565ddd9f4203d5334l-f3613071692r.jpg)

![150 List Street - Photo 12](http://lh.rdcpix.com/8c3031eaeea8927565ddd9f4203d5334l-f2467669605r.jpg)

![150 List Street - Photo 13](http://lh.rdcpix.com/8c3031eaeea8927565ddd9f4203d5334l-f3071158213r.jpg)

![150 List Street - Photo 14](http://lh.rdcpix.com/8c3031eaeea8927565ddd9f4203d5334l-f2288709070r.jpg)

![150 List Street - Photo 15](http://lh.rdcpix.com/8c3031eaeea8927565ddd9f4203d5334l-f1908123041r.jpg)

![150 List Street - Photo 16](http://lh.rdcpix.com/8c3031eaeea8927565ddd9f4203d5334l-f1954785412r.jpg)

![150 List Street - Photo 17](http://lh.rdcpix.com/8c3031eaeea8927565ddd9f4203d5334l-f3587095394r.jpg)

![150 List Street - Photo 18](http://lh.rdcpix.com/8c3031eaeea8927565ddd9f4203d5334l-f3072586550r.jpg)

![150 List Street - Photo 19](http://lh.rdcpix.com/8c3031eaeea8927565ddd9f4203d5334l-f220737543r.jpg)

![150 List Street - Photo 20](http://lh.rdcpix.com/8c3031eaeea8927565ddd9f4203d5334l-f3577141240r.jpg)

![150 List Street - Photo 21](http://lh.rdcpix.com/8c3031eaeea8927565ddd9f4203d5334l-f1249262613r.jpg)

![150 List Street - Photo 22](http://lh.rdcpix.com/8c3031eaeea8927565ddd9f4203d5334l-f858121358r.jpg)

![150 List Street - Photo 23](http://lh.rdcpix.com/8c3031eaeea8927565ddd9f4203d5334l-f773135509r.jpg)

![150 List Street - Photo 24](http://lh.rdcpix.com/8c3031eaeea8927565ddd9f4203d5334l-f2433212493r.jpg)

![150 List Street - Photo 25](http://lh.rdcpix.com/8c3031eaeea8927565ddd9f4203d5334l-f1927494650r.jpg)

![150 List Street - Photo 26](http://lh.rdcpix.com/8c3031eaeea8927565ddd9f4203d5334l-f440062297r.jpg)

![150 List Street - Photo 27](http://lh.rdcpix.com/8c3031eaeea8927565ddd9f4203d5334l-f583447761r.jpg)

![150 List Street - Photo 28](http://lh.rdcpix.com/8c3031eaeea8927565ddd9f4203d5334l-f1187929206r.jpg)

![150 List Street - Photo 29](http://lh.rdcpix.com/8c3031eaeea8927565ddd9f4203d5334l-f2726731123r.jpg)

![150 List Street - Photo 30](http://lh.rdcpix.com/8c3031eaeea8927565ddd9f4203d5334l-f4036902751r.jpg)

---

**MLS#:** 618920 | **Updated:** 2026-10-20
**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/150-list-street-upper-matecumbe-key-islamorada-fl-33036-67eb6eb057874c5abcf85e15a85b3e9c)

---

## Structured Data

```json
{
  "@context": "https://schema.org",
  "@type": "RealEstateListing",
  "@id": "https://www.propertysimple.ai/listing/150-list-street-upper-matecumbe-key-islamorada-fl-33036-67eb6eb057874c5abcf85e15a85b3e9c#listing",
  "url": "https://www.propertysimple.ai/listing/150-list-street-upper-matecumbe-key-islamorada-fl-33036-67eb6eb057874c5abcf85e15a85b3e9c",
  "name": "150 List Street, Upper Matecumbe Key Islamorada, FL 33036",
  "description": "Discover an extraordinary opportunity to own 34,000 square feet of prime bayfront real estate in one of Islamorada's most coveted and private enclaves. Boasting 100+ feet of pristine bay frontage, this exceptional property captures open water views, serene sunsets, and the essence of the Florida Keys lifestyle. Tucked within the property is a charming ground level 1950s cottage offering one bedroom and one bathroom - ideal for a comfortable interim residence while you bring your custom waterfront vision to life. For boating enthusiasts, the estate offers dockage with direct bay access, placing world-class fishing, sandbars, and crystal-clear waters just moments away. A PERMIT HAS BEEN ISSUED to repair and expand the existing dock and add two boat lifts (20,000 lb and 16,000 lb), significantly enhancing the property's boating capabilities and long-term value. With the existing estate slated for demolition and redevelopment, the conceptual renderings unveil a spectacular 4,872-square-foot custom residence offering five bedrooms, five and a half bathrooms, a three-car garage, and a resort style pool - all thoughtfully designed to capture water views from every vantage point. This remarkable bayfront estate offers endless possibilities in an unparalleled setting.",
  "image": [
    "http://lh.rdcpix.com/8c3031eaeea8927565ddd9f4203d5334l-f1198726027r.jpg",
    "http://lh.rdcpix.com/8c3031eaeea8927565ddd9f4203d5334l-f1348255021r.jpg",
    "http://lh.rdcpix.com/8c3031eaeea8927565ddd9f4203d5334l-f3411482918r.jpg",
    "http://lh.rdcpix.com/8c3031eaeea8927565ddd9f4203d5334l-f9685714r.jpg",
    "http://lh.rdcpix.com/8c3031eaeea8927565ddd9f4203d5334l-f3671579448r.jpg",
    "http://lh.rdcpix.com/8c3031eaeea8927565ddd9f4203d5334l-f3834228964r.jpg",
    "http://lh.rdcpix.com/8c3031eaeea8927565ddd9f4203d5334l-f3265109240r.jpg",
    "http://lh.rdcpix.com/8c3031eaeea8927565ddd9f4203d5334l-f3163544369r.jpg",
    "http://lh.rdcpix.com/8c3031eaeea8927565ddd9f4203d5334l-f120344394r.jpg",
    "http://lh.rdcpix.com/8c3031eaeea8927565ddd9f4203d5334l-f2747870334r.jpg",
    "http://lh.rdcpix.com/8c3031eaeea8927565ddd9f4203d5334l-f3613071692r.jpg",
    "http://lh.rdcpix.com/8c3031eaeea8927565ddd9f4203d5334l-f2467669605r.jpg",
    "http://lh.rdcpix.com/8c3031eaeea8927565ddd9f4203d5334l-f3071158213r.jpg",
    "http://lh.rdcpix.com/8c3031eaeea8927565ddd9f4203d5334l-f2288709070r.jpg",
    "http://lh.rdcpix.com/8c3031eaeea8927565ddd9f4203d5334l-f1908123041r.jpg",
    "http://lh.rdcpix.com/8c3031eaeea8927565ddd9f4203d5334l-f1954785412r.jpg",
    "http://lh.rdcpix.com/8c3031eaeea8927565ddd9f4203d5334l-f3587095394r.jpg",
    "http://lh.rdcpix.com/8c3031eaeea8927565ddd9f4203d5334l-f3072586550r.jpg",
    "http://lh.rdcpix.com/8c3031eaeea8927565ddd9f4203d5334l-f220737543r.jpg",
    "http://lh.rdcpix.com/8c3031eaeea8927565ddd9f4203d5334l-f3577141240r.jpg",
    "http://lh.rdcpix.com/8c3031eaeea8927565ddd9f4203d5334l-f1249262613r.jpg",
    "http://lh.rdcpix.com/8c3031eaeea8927565ddd9f4203d5334l-f858121358r.jpg",
    "http://lh.rdcpix.com/8c3031eaeea8927565ddd9f4203d5334l-f773135509r.jpg",
    "http://lh.rdcpix.com/8c3031eaeea8927565ddd9f4203d5334l-f2433212493r.jpg",
    "http://lh.rdcpix.com/8c3031eaeea8927565ddd9f4203d5334l-f1927494650r.jpg",
    "http://lh.rdcpix.com/8c3031eaeea8927565ddd9f4203d5334l-f440062297r.jpg",
    "http://lh.rdcpix.com/8c3031eaeea8927565ddd9f4203d5334l-f583447761r.jpg",
    "http://lh.rdcpix.com/8c3031eaeea8927565ddd9f4203d5334l-f1187929206r.jpg",
    "http://lh.rdcpix.com/8c3031eaeea8927565ddd9f4203d5334l-f2726731123r.jpg",
    "http://lh.rdcpix.com/8c3031eaeea8927565ddd9f4203d5334l-f4036902751r.jpg"
  ],
  "primaryImageOfPage": {
    "@type": "ImageObject",
    "url": "http://lh.rdcpix.com/8c3031eaeea8927565ddd9f4203d5334l-f1198726027r.jpg",
    "caption": "150 List Street - Upper Matecumbe Key Islamorada, FL"
  },
  "datePosted": "2026-03-04",
  "dateModified": "2026-10-20T17:54:55.984Z",
  "mainEntity": {
    "@type": "Place",
    "@id": "https://www.propertysimple.ai/listing/150-list-street-upper-matecumbe-key-islamorada-fl-33036-67eb6eb057874c5abcf85e15a85b3e9c#property",
    "name": "150 List Street, Upper Matecumbe Key Islamorada, FL 33036",
    "address": {
      "@type": "PostalAddress",
      "streetAddress": "150 List Street",
      "addressLocality": "Upper Matecumbe Key Islamorada",
      "addressRegion": "FL",
      "postalCode": "33036",
      "addressCountry": "US"
    },
    "geo": {
      "@type": "GeoCoordinates",
      "latitude": 24.924569,
      "longitude": -80.629517
    },
    "image": [
      "http://lh.rdcpix.com/8c3031eaeea8927565ddd9f4203d5334l-f1198726027r.jpg",
      "http://lh.rdcpix.com/8c3031eaeea8927565ddd9f4203d5334l-f1348255021r.jpg",
      "http://lh.rdcpix.com/8c3031eaeea8927565ddd9f4203d5334l-f3411482918r.jpg",
      "http://lh.rdcpix.com/8c3031eaeea8927565ddd9f4203d5334l-f9685714r.jpg",
      "http://lh.rdcpix.com/8c3031eaeea8927565ddd9f4203d5334l-f3671579448r.jpg",
      "http://lh.rdcpix.com/8c3031eaeea8927565ddd9f4203d5334l-f3834228964r.jpg",
      "http://lh.rdcpix.com/8c3031eaeea8927565ddd9f4203d5334l-f3265109240r.jpg",
      "http://lh.rdcpix.com/8c3031eaeea8927565ddd9f4203d5334l-f3163544369r.jpg",
      "http://lh.rdcpix.com/8c3031eaeea8927565ddd9f4203d5334l-f120344394r.jpg",
      "http://lh.rdcpix.com/8c3031eaeea8927565ddd9f4203d5334l-f2747870334r.jpg",
      "http://lh.rdcpix.com/8c3031eaeea8927565ddd9f4203d5334l-f3613071692r.jpg",
      "http://lh.rdcpix.com/8c3031eaeea8927565ddd9f4203d5334l-f2467669605r.jpg",
      "http://lh.rdcpix.com/8c3031eaeea8927565ddd9f4203d5334l-f3071158213r.jpg",
      "http://lh.rdcpix.com/8c3031eaeea8927565ddd9f4203d5334l-f2288709070r.jpg",
      "http://lh.rdcpix.com/8c3031eaeea8927565ddd9f4203d5334l-f1908123041r.jpg",
      "http://lh.rdcpix.com/8c3031eaeea8927565ddd9f4203d5334l-f1954785412r.jpg",
      "http://lh.rdcpix.com/8c3031eaeea8927565ddd9f4203d5334l-f3587095394r.jpg",
      "http://lh.rdcpix.com/8c3031eaeea8927565ddd9f4203d5334l-f3072586550r.jpg",
      "http://lh.rdcpix.com/8c3031eaeea8927565ddd9f4203d5334l-f220737543r.jpg",
      "http://lh.rdcpix.com/8c3031eaeea8927565ddd9f4203d5334l-f3577141240r.jpg",
      "http://lh.rdcpix.com/8c3031eaeea8927565ddd9f4203d5334l-f1249262613r.jpg",
      "http://lh.rdcpix.com/8c3031eaeea8927565ddd9f4203d5334l-f858121358r.jpg",
      "http://lh.rdcpix.com/8c3031eaeea8927565ddd9f4203d5334l-f773135509r.jpg",
      "http://lh.rdcpix.com/8c3031eaeea8927565ddd9f4203d5334l-f2433212493r.jpg",
      "http://lh.rdcpix.com/8c3031eaeea8927565ddd9f4203d5334l-f1927494650r.jpg",
      "http://lh.rdcpix.com/8c3031eaeea8927565ddd9f4203d5334l-f440062297r.jpg",
      "http://lh.rdcpix.com/8c3031eaeea8927565ddd9f4203d5334l-f583447761r.jpg",
      "http://lh.rdcpix.com/8c3031eaeea8927565ddd9f4203d5334l-f1187929206r.jpg",
      "http://lh.rdcpix.com/8c3031eaeea8927565ddd9f4203d5334l-f2726731123r.jpg",
      "http://lh.rdcpix.com/8c3031eaeea8927565ddd9f4203d5334l-f4036902751r.jpg"
    ],
    "identifier": {
      "@type": "PropertyValue",
      "propertyID": "MLS",
      "value": "618920"
    },
    "amenityFeature": [
      {
        "@type": "LocationFeatureSpecification",
        "name": "Views",
        "value": "Water"
      },
      {
        "@type": "LocationFeatureSpecification",
        "name": "Waterfront",
        "value": true
      },
      {
        "@type": "LocationFeatureSpecification",
        "name": "View",
        "value": true
      }
    ],
    "additionalProperty": [
      {
        "@type": "PropertyValue",
        "name": "Lot Size",
        "value": "0.78 acres"
      },
      {
        "@type": "PropertyValue",
        "name": "Property Subtype",
        "value": "Other"
      },
      {
        "@type": "PropertyValue",
        "name": "Property Type",
        "value": "Land"
      }
    ]
  },
  "offers": {
    "@type": "Offer",
    "@id": "https://www.propertysimple.ai/listing/150-list-street-upper-matecumbe-key-islamorada-fl-33036-67eb6eb057874c5abcf85e15a85b3e9c#offer",
    "url": "https://www.propertysimple.ai/listing/150-list-street-upper-matecumbe-key-islamorada-fl-33036-67eb6eb057874c5abcf85e15a85b3e9c",
    "price": 4499500,
    "priceCurrency": "USD",
    "businessFunction": "http://purl.org/goodrelations/v1#Sell",
    "availability": "https://schema.org/InStock",
    "seller": {
      "@id": "https://www.propertysimple.ai/listing/150-list-street-upper-matecumbe-key-islamorada-fl-33036-67eb6eb057874c5abcf85e15a85b3e9c#agent"
    }
  },
  "provider": {
    "@type": "Person",
    "@id": "https://www.propertysimple.ai/listing/150-list-street-upper-matecumbe-key-islamorada-fl-33036-67eb6eb057874c5abcf85e15a85b3e9c#agent",
    "name": "Bonnie Ekblom Oliver",
    "worksFor": {
      "@type": "Organization",
      "@id": "https://www.propertysimple.ai/listing/150-list-street-upper-matecumbe-key-islamorada-fl-33036-67eb6eb057874c5abcf85e15a85b3e9c#brokerage",
      "name": "Ocean Sotheby's International Realty",
      "telephone": "3057128888"
    }
  }
}
```