# 4520 Smugglers Drive, Captiva, FL 33924

> **TL;DR:** land, $130,000. Est. $695/mo. Listed 34 days.

## Property at a Glance

| Attribute | Value |
|-----------|-------|
| Price | $130,000 |
| Lot Size | 9,496 sqft (0.22 acres) |
| Property Type | Land (Other) |
| Status | Active |
| Days on Market | 34 |

## Estimated Monthly Costs

| Category | Amount |
|----------|--------|
| Principal & Interest (20% down, 30-year at 6.5%) | $657 |
| Estimated Insurance | $38 |
| **Total** | **$695** |

## Property Highlights

- 0.22 acre lot

## Description

### Agent Description
CASTAWAY KEY ISLAND LIVING STARTS HERE. This homesite on Upper Captiva offers the perfect opportunity to build your own private island retreat in the desirable Castaway Key community. Surrounded by the natural beauty and relaxed atmosphere that make Upper Captiva so special, this lot provides an ideal setting for a custom full time residence, vacation getaway, or investment property. Enjoy the unique island lifestyle with beautiful Gulf beaches, boating, fishing, shelling, and unforgettable sunsets all close by. With its tropical surroundings and peaceful setting, this property is a blank canvas ready for your vision. Build the home you have been dreaming of and create your own slice of paradise in Castaway Key on Upper Captiva.

## Location

- **Address:** 4520 Smugglers Drive, Captiva, FL 33924
- **County:** Lee
- **Neighborhood:** CASTAWAY KEY
- **Coordinates:** 26.596488, -82.22128
- **Google Maps:** https://www.google.com/maps?q=26.596488,-82.22128

## Virtual Tour & Media

- **Video Tour:** https://www.propertypanorama.com/instaview/fgcmls/2026033871

## Listing Agent

- **Name:** Jeffrey Miloff · **License:** 252000469
- **Brokerage:** The Keyes Company
- **Phone:** 2395650831
- **Broker Phone:** 239-373-5300
- **Listing URL:** [View original listing](https://www.realtor.com/realestateandhomes-detail/4520-Smugglers-Dr_Captiva_FL_33924_M58850-95854?f=listhub&s=FMSWFL&m=2026033871&c=propsimple)

## Photos

![4520 Smugglers Drive - Photo 1](http://lh.rdcpix.com/357dd69f04b335c30a71f6ab2b490427l-f2101916418r.jpg)

![4520 Smugglers Drive - Photo 2](http://lh.rdcpix.com/357dd69f04b335c30a71f6ab2b490427l-f2248313859r.jpg)

![4520 Smugglers Drive - Photo 3](http://lh.rdcpix.com/357dd69f04b335c30a71f6ab2b490427l-f1586612923r.jpg)

![4520 Smugglers Drive - Photo 4](http://lh.rdcpix.com/357dd69f04b335c30a71f6ab2b490427l-f2369713319r.jpg)

![4520 Smugglers Drive - Photo 5](http://lh.rdcpix.com/357dd69f04b335c30a71f6ab2b490427l-f4071027475r.jpg)

![4520 Smugglers Drive - Photo 6](http://lh.rdcpix.com/357dd69f04b335c30a71f6ab2b490427l-f2061152684r.jpg)

![4520 Smugglers Drive - Photo 7](http://lh.rdcpix.com/357dd69f04b335c30a71f6ab2b490427l-f3532191770r.jpg)

![4520 Smugglers Drive - Photo 8](http://lh.rdcpix.com/357dd69f04b335c30a71f6ab2b490427l-f1668380806r.jpg)

![4520 Smugglers Drive - Photo 9](http://lh.rdcpix.com/357dd69f04b335c30a71f6ab2b490427l-f4274391942r.jpg)

![4520 Smugglers Drive - Photo 10](http://lh.rdcpix.com/357dd69f04b335c30a71f6ab2b490427l-f3833232889r.jpg)

![4520 Smugglers Drive - Photo 11](http://lh.rdcpix.com/357dd69f04b335c30a71f6ab2b490427l-f3468331510r.jpg)

![4520 Smugglers Drive - Photo 12](http://lh.rdcpix.com/357dd69f04b335c30a71f6ab2b490427l-f1869775639r.jpg)

![4520 Smugglers Drive - Photo 13](http://lh.rdcpix.com/357dd69f04b335c30a71f6ab2b490427l-f405621008r.jpg)

![4520 Smugglers Drive - Photo 14](http://lh.rdcpix.com/357dd69f04b335c30a71f6ab2b490427l-f954637229r.jpg)

![4520 Smugglers Drive - Photo 15](http://lh.rdcpix.com/357dd69f04b335c30a71f6ab2b490427l-f4010196113r.jpg)

![4520 Smugglers Drive - Photo 16](http://lh.rdcpix.com/357dd69f04b335c30a71f6ab2b490427l-f2668353826r.jpg)

![4520 Smugglers Drive - Photo 17](http://lh.rdcpix.com/357dd69f04b335c30a71f6ab2b490427l-f3681252534r.jpg)

![4520 Smugglers Drive - Photo 18](http://lh.rdcpix.com/357dd69f04b335c30a71f6ab2b490427l-f2981655426r.jpg)

![4520 Smugglers Drive - Photo 19](http://lh.rdcpix.com/357dd69f04b335c30a71f6ab2b490427l-f819143763r.jpg)

![4520 Smugglers Drive - Photo 20](http://lh.rdcpix.com/357dd69f04b335c30a71f6ab2b490427l-f1246688071r.jpg)

![4520 Smugglers Drive - Photo 21](http://lh.rdcpix.com/357dd69f04b335c30a71f6ab2b490427l-f664740193r.jpg)

![4520 Smugglers Drive - Photo 22](http://lh.rdcpix.com/357dd69f04b335c30a71f6ab2b490427l-f2376239085r.jpg)

![4520 Smugglers Drive - Photo 23](http://lh.rdcpix.com/357dd69f04b335c30a71f6ab2b490427l-f426898396r.jpg)

![4520 Smugglers Drive - Photo 24](http://lh.rdcpix.com/357dd69f04b335c30a71f6ab2b490427l-f1914993791r.jpg)

![4520 Smugglers Drive - Photo 25](http://lh.rdcpix.com/357dd69f04b335c30a71f6ab2b490427l-f792384235r.jpg)

![4520 Smugglers Drive - Photo 26](http://lh.rdcpix.com/357dd69f04b335c30a71f6ab2b490427l-f260598203r.jpg)

![4520 Smugglers Drive - Photo 27](http://lh.rdcpix.com/357dd69f04b335c30a71f6ab2b490427l-f3106883124r.jpg)

![4520 Smugglers Drive - Photo 28](http://lh.rdcpix.com/357dd69f04b335c30a71f6ab2b490427l-f3059583488r.jpg)

![4520 Smugglers Drive - Photo 29](http://lh.rdcpix.com/357dd69f04b335c30a71f6ab2b490427l-f1430955028r.jpg)

![4520 Smugglers Drive - Photo 30](http://lh.rdcpix.com/357dd69f04b335c30a71f6ab2b490427l-f476512925r.jpg)

![4520 Smugglers Drive - Photo 31](http://lh.rdcpix.com/357dd69f04b335c30a71f6ab2b490427l-f788748314r.jpg)

![4520 Smugglers Drive - Photo 32](http://lh.rdcpix.com/357dd69f04b335c30a71f6ab2b490427l-f3083715812r.jpg)

![4520 Smugglers Drive - Photo 33](http://lh.rdcpix.com/357dd69f04b335c30a71f6ab2b490427l-f215495106r.jpg)

![4520 Smugglers Drive - Photo 34](http://lh.rdcpix.com/357dd69f04b335c30a71f6ab2b490427l-f2544123992r.jpg)

![4520 Smugglers Drive - Photo 35](http://lh.rdcpix.com/357dd69f04b335c30a71f6ab2b490427l-f1382635357r.jpg)

![4520 Smugglers Drive - Photo 36](http://lh.rdcpix.com/357dd69f04b335c30a71f6ab2b490427l-f134583371r.jpg)

![4520 Smugglers Drive - Photo 37](http://lh.rdcpix.com/357dd69f04b335c30a71f6ab2b490427l-f4218550803r.jpg)

![4520 Smugglers Drive - Photo 38](http://lh.rdcpix.com/357dd69f04b335c30a71f6ab2b490427l-f29020852r.jpg)

![4520 Smugglers Drive - Photo 39](http://lh.rdcpix.com/357dd69f04b335c30a71f6ab2b490427l-f1100781761r.jpg)

![4520 Smugglers Drive - Photo 40](http://lh.rdcpix.com/357dd69f04b335c30a71f6ab2b490427l-f701796182r.jpg)

![4520 Smugglers Drive - Photo 41](http://lh.rdcpix.com/357dd69f04b335c30a71f6ab2b490427l-f2850212037r.jpg)

![4520 Smugglers Drive - Photo 42](http://lh.rdcpix.com/357dd69f04b335c30a71f6ab2b490427l-f1248989979r.jpg)

---

**MLS#:** 2026033871 | **Updated:** 2026-08-20
**Source:** listhub

*Copyright © 2026 Florida Gulf Coast Multiple Listing Service, Inc. 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/4520-smugglers-drive-captiva-fl-33924-26033871)

---

## Structured Data

```json
{
  "@context": "https://schema.org",
  "@type": "RealEstateListing",
  "@id": "https://www.propertysimple.ai/listing/4520-smugglers-drive-captiva-fl-33924-26033871#listing",
  "url": "https://www.propertysimple.ai/listing/4520-smugglers-drive-captiva-fl-33924-26033871",
  "name": "4520 Smugglers Drive, Captiva, FL 33924",
  "description": "CASTAWAY KEY ISLAND LIVING STARTS HERE. This homesite on Upper Captiva offers the perfect opportunity to build your own private island retreat in the desirable Castaway Key community. Surrounded by the natural beauty and relaxed atmosphere that make Upper Captiva so special, this lot provides an ideal setting for a custom full time residence, vacation getaway, or investment property. Enjoy the unique island lifestyle with beautiful Gulf beaches, boating, fishing, shelling, and unforgettable sunsets all close by. With its tropical surroundings and peaceful setting, this property is a blank canvas ready for your vision. Build the home you have been dreaming of and create your own slice of paradise in Castaway Key on Upper Captiva.",
  "image": [
    "http://lh.rdcpix.com/357dd69f04b335c30a71f6ab2b490427l-f2101916418r.jpg",
    "http://lh.rdcpix.com/357dd69f04b335c30a71f6ab2b490427l-f2248313859r.jpg",
    "http://lh.rdcpix.com/357dd69f04b335c30a71f6ab2b490427l-f1586612923r.jpg",
    "http://lh.rdcpix.com/357dd69f04b335c30a71f6ab2b490427l-f2369713319r.jpg",
    "http://lh.rdcpix.com/357dd69f04b335c30a71f6ab2b490427l-f4071027475r.jpg",
    "http://lh.rdcpix.com/357dd69f04b335c30a71f6ab2b490427l-f2061152684r.jpg",
    "http://lh.rdcpix.com/357dd69f04b335c30a71f6ab2b490427l-f3532191770r.jpg",
    "http://lh.rdcpix.com/357dd69f04b335c30a71f6ab2b490427l-f1668380806r.jpg",
    "http://lh.rdcpix.com/357dd69f04b335c30a71f6ab2b490427l-f4274391942r.jpg",
    "http://lh.rdcpix.com/357dd69f04b335c30a71f6ab2b490427l-f3833232889r.jpg",
    "http://lh.rdcpix.com/357dd69f04b335c30a71f6ab2b490427l-f3468331510r.jpg",
    "http://lh.rdcpix.com/357dd69f04b335c30a71f6ab2b490427l-f1869775639r.jpg",
    "http://lh.rdcpix.com/357dd69f04b335c30a71f6ab2b490427l-f405621008r.jpg",
    "http://lh.rdcpix.com/357dd69f04b335c30a71f6ab2b490427l-f954637229r.jpg",
    "http://lh.rdcpix.com/357dd69f04b335c30a71f6ab2b490427l-f4010196113r.jpg",
    "http://lh.rdcpix.com/357dd69f04b335c30a71f6ab2b490427l-f2668353826r.jpg",
    "http://lh.rdcpix.com/357dd69f04b335c30a71f6ab2b490427l-f3681252534r.jpg",
    "http://lh.rdcpix.com/357dd69f04b335c30a71f6ab2b490427l-f2981655426r.jpg",
    "http://lh.rdcpix.com/357dd69f04b335c30a71f6ab2b490427l-f819143763r.jpg",
    "http://lh.rdcpix.com/357dd69f04b335c30a71f6ab2b490427l-f1246688071r.jpg",
    "http://lh.rdcpix.com/357dd69f04b335c30a71f6ab2b490427l-f664740193r.jpg",
    "http://lh.rdcpix.com/357dd69f04b335c30a71f6ab2b490427l-f2376239085r.jpg",
    "http://lh.rdcpix.com/357dd69f04b335c30a71f6ab2b490427l-f426898396r.jpg",
    "http://lh.rdcpix.com/357dd69f04b335c30a71f6ab2b490427l-f1914993791r.jpg",
    "http://lh.rdcpix.com/357dd69f04b335c30a71f6ab2b490427l-f792384235r.jpg",
    "http://lh.rdcpix.com/357dd69f04b335c30a71f6ab2b490427l-f260598203r.jpg",
    "http://lh.rdcpix.com/357dd69f04b335c30a71f6ab2b490427l-f3106883124r.jpg",
    "http://lh.rdcpix.com/357dd69f04b335c30a71f6ab2b490427l-f3059583488r.jpg",
    "http://lh.rdcpix.com/357dd69f04b335c30a71f6ab2b490427l-f1430955028r.jpg",
    "http://lh.rdcpix.com/357dd69f04b335c30a71f6ab2b490427l-f476512925r.jpg",
    "http://lh.rdcpix.com/357dd69f04b335c30a71f6ab2b490427l-f788748314r.jpg",
    "http://lh.rdcpix.com/357dd69f04b335c30a71f6ab2b490427l-f3083715812r.jpg",
    "http://lh.rdcpix.com/357dd69f04b335c30a71f6ab2b490427l-f215495106r.jpg",
    "http://lh.rdcpix.com/357dd69f04b335c30a71f6ab2b490427l-f2544123992r.jpg",
    "http://lh.rdcpix.com/357dd69f04b335c30a71f6ab2b490427l-f1382635357r.jpg",
    "http://lh.rdcpix.com/357dd69f04b335c30a71f6ab2b490427l-f134583371r.jpg",
    "http://lh.rdcpix.com/357dd69f04b335c30a71f6ab2b490427l-f4218550803r.jpg",
    "http://lh.rdcpix.com/357dd69f04b335c30a71f6ab2b490427l-f29020852r.jpg",
    "http://lh.rdcpix.com/357dd69f04b335c30a71f6ab2b490427l-f1100781761r.jpg",
    "http://lh.rdcpix.com/357dd69f04b335c30a71f6ab2b490427l-f701796182r.jpg",
    "http://lh.rdcpix.com/357dd69f04b335c30a71f6ab2b490427l-f2850212037r.jpg",
    "http://lh.rdcpix.com/357dd69f04b335c30a71f6ab2b490427l-f1248989979r.jpg"
  ],
  "primaryImageOfPage": {
    "@type": "ImageObject",
    "url": "http://lh.rdcpix.com/357dd69f04b335c30a71f6ab2b490427l-f2101916418r.jpg",
    "caption": "4520 Smugglers Drive - Captiva, FL"
  },
  "datePosted": "2026-08-11T00:00:00+00:00",
  "dateModified": "2026-08-20T19:35:00.205006+00:00",
  "mainEntity": {
    "@type": "Place",
    "@id": "https://www.propertysimple.ai/listing/4520-smugglers-drive-captiva-fl-33924-26033871#property",
    "name": "4520 Smugglers Drive, Captiva, FL 33924",
    "address": {
      "@type": "PostalAddress",
      "streetAddress": "4520 Smugglers Drive",
      "addressLocality": "Captiva",
      "addressRegion": "FL",
      "postalCode": "33924",
      "addressCountry": "US"
    },
    "geo": {
      "@type": "GeoCoordinates",
      "latitude": 26.596488,
      "longitude": -82.22128
    },
    "image": [
      "http://lh.rdcpix.com/357dd69f04b335c30a71f6ab2b490427l-f2101916418r.jpg",
      "http://lh.rdcpix.com/357dd69f04b335c30a71f6ab2b490427l-f2248313859r.jpg",
      "http://lh.rdcpix.com/357dd69f04b335c30a71f6ab2b490427l-f1586612923r.jpg",
      "http://lh.rdcpix.com/357dd69f04b335c30a71f6ab2b490427l-f2369713319r.jpg",
      "http://lh.rdcpix.com/357dd69f04b335c30a71f6ab2b490427l-f4071027475r.jpg",
      "http://lh.rdcpix.com/357dd69f04b335c30a71f6ab2b490427l-f2061152684r.jpg",
      "http://lh.rdcpix.com/357dd69f04b335c30a71f6ab2b490427l-f3532191770r.jpg",
      "http://lh.rdcpix.com/357dd69f04b335c30a71f6ab2b490427l-f1668380806r.jpg",
      "http://lh.rdcpix.com/357dd69f04b335c30a71f6ab2b490427l-f4274391942r.jpg",
      "http://lh.rdcpix.com/357dd69f04b335c30a71f6ab2b490427l-f3833232889r.jpg",
      "http://lh.rdcpix.com/357dd69f04b335c30a71f6ab2b490427l-f3468331510r.jpg",
      "http://lh.rdcpix.com/357dd69f04b335c30a71f6ab2b490427l-f1869775639r.jpg",
      "http://lh.rdcpix.com/357dd69f04b335c30a71f6ab2b490427l-f405621008r.jpg",
      "http://lh.rdcpix.com/357dd69f04b335c30a71f6ab2b490427l-f954637229r.jpg",
      "http://lh.rdcpix.com/357dd69f04b335c30a71f6ab2b490427l-f4010196113r.jpg",
      "http://lh.rdcpix.com/357dd69f04b335c30a71f6ab2b490427l-f2668353826r.jpg",
      "http://lh.rdcpix.com/357dd69f04b335c30a71f6ab2b490427l-f3681252534r.jpg",
      "http://lh.rdcpix.com/357dd69f04b335c30a71f6ab2b490427l-f2981655426r.jpg",
      "http://lh.rdcpix.com/357dd69f04b335c30a71f6ab2b490427l-f819143763r.jpg",
      "http://lh.rdcpix.com/357dd69f04b335c30a71f6ab2b490427l-f1246688071r.jpg",
      "http://lh.rdcpix.com/357dd69f04b335c30a71f6ab2b490427l-f664740193r.jpg",
      "http://lh.rdcpix.com/357dd69f04b335c30a71f6ab2b490427l-f2376239085r.jpg",
      "http://lh.rdcpix.com/357dd69f04b335c30a71f6ab2b490427l-f426898396r.jpg",
      "http://lh.rdcpix.com/357dd69f04b335c30a71f6ab2b490427l-f1914993791r.jpg",
      "http://lh.rdcpix.com/357dd69f04b335c30a71f6ab2b490427l-f792384235r.jpg",
      "http://lh.rdcpix.com/357dd69f04b335c30a71f6ab2b490427l-f260598203r.jpg",
      "http://lh.rdcpix.com/357dd69f04b335c30a71f6ab2b490427l-f3106883124r.jpg",
      "http://lh.rdcpix.com/357dd69f04b335c30a71f6ab2b490427l-f3059583488r.jpg",
      "http://lh.rdcpix.com/357dd69f04b335c30a71f6ab2b490427l-f1430955028r.jpg",
      "http://lh.rdcpix.com/357dd69f04b335c30a71f6ab2b490427l-f476512925r.jpg",
      "http://lh.rdcpix.com/357dd69f04b335c30a71f6ab2b490427l-f788748314r.jpg",
      "http://lh.rdcpix.com/357dd69f04b335c30a71f6ab2b490427l-f3083715812r.jpg",
      "http://lh.rdcpix.com/357dd69f04b335c30a71f6ab2b490427l-f215495106r.jpg",
      "http://lh.rdcpix.com/357dd69f04b335c30a71f6ab2b490427l-f2544123992r.jpg",
      "http://lh.rdcpix.com/357dd69f04b335c30a71f6ab2b490427l-f1382635357r.jpg",
      "http://lh.rdcpix.com/357dd69f04b335c30a71f6ab2b490427l-f134583371r.jpg",
      "http://lh.rdcpix.com/357dd69f04b335c30a71f6ab2b490427l-f4218550803r.jpg",
      "http://lh.rdcpix.com/357dd69f04b335c30a71f6ab2b490427l-f29020852r.jpg",
      "http://lh.rdcpix.com/357dd69f04b335c30a71f6ab2b490427l-f1100781761r.jpg",
      "http://lh.rdcpix.com/357dd69f04b335c30a71f6ab2b490427l-f701796182r.jpg",
      "http://lh.rdcpix.com/357dd69f04b335c30a71f6ab2b490427l-f2850212037r.jpg",
      "http://lh.rdcpix.com/357dd69f04b335c30a71f6ab2b490427l-f1248989979r.jpg"
    ],
    "identifier": {
      "@type": "PropertyValue",
      "propertyID": "MLS",
      "value": "2026033871"
    },
    "additionalProperty": [
      {
        "@type": "PropertyValue",
        "name": "Lot Size",
        "value": "0.22 acres"
      },
      {
        "@type": "PropertyValue",
        "name": "Property Subtype",
        "value": "Other"
      },
      {
        "@type": "PropertyValue",
        "name": "Property Type",
        "value": "Land"
      }
    ]
  },
  "offers": {
    "@type": "Offer",
    "@id": "https://www.propertysimple.ai/listing/4520-smugglers-drive-captiva-fl-33924-26033871#offer",
    "url": "https://www.propertysimple.ai/listing/4520-smugglers-drive-captiva-fl-33924-26033871",
    "price": 130000,
    "priceCurrency": "USD",
    "businessFunction": "http://purl.org/goodrelations/v1#Sell",
    "availability": "https://schema.org/InStock",
    "seller": {
      "@id": "https://www.propertysimple.ai/listing/4520-smugglers-drive-captiva-fl-33924-26033871#agent"
    }
  },
  "provider": {
    "@type": "Person",
    "@id": "https://www.propertysimple.ai/listing/4520-smugglers-drive-captiva-fl-33924-26033871#agent",
    "name": "Jeffrey Miloff",
    "telephone": "2395650831",
    "worksFor": {
      "@type": "Organization",
      "@id": "https://www.propertysimple.ai/listing/4520-smugglers-drive-captiva-fl-33924-26033871#brokerage",
      "name": "The Keyes Company",
      "telephone": "239-373-5300"
    }
  }
}
```