# Overseas Highway, Upper Matecumbe Key Islamorada, FL 33036 > **TL;DR:** land, $3,500,000. > Waterfront, View. Est. $18,719/mo. Listed 39 days. ## Property at a Glance | Attribute | Value | |-----------|-------| | Price | $3,500,000 | | Lot Size | 229,561 sqft (5.27 acres) | | Property Type | Land (Other) | | Status | Active | | Days on Market | 39 | ## 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%) | $17,698 | | Estimated Insurance | $1,021 | | **Total** | **$18,719** | ## Key Amenities - Waterfront - View ## Property Highlights - 5.27 acre lot - Waterfront ## Description ### Agent Description A rare opportunity to own an expansive bayfront parcel at Mile Marker 81 on Upper Matecumbe Key, offered for sale for the first time since its acquisition in 1937. Located in the heart of Islamorada, this remarkable property encompasses approximately 5.26 total deeded acres, including approximately 2.84 acres of upland, with more than 250 feet of frontage on Florida Bay. The substantial acreage and natural setting offer exceptional privacy and seclusion, while still being close to the restaurants, marinas, shops, galleries, and world-class boating and fishing that define the Islamorada lifestyle. With its coveted Upper Matecumbe Key location, expansive bayfront, and rare parcel size, this is an extraordinary opportunity to create a private waterfront estate in the Florida Keys. Zoned Native Residential (NR), allowing single-family residential use subject to applicable Village requirements. Allowable clearing, building area, and development potential are subject to applicable Village of Islamorada regulations. Buyer to independently verify all development potential with the Village of Islamorada. ## Location - **Address:** Overseas Highway, Upper Matecumbe Key Islamorada, FL 33036 - **County:** Monroe - **Neighborhood:** Unplatted Upper Mate (82.0) - **Coordinates:** 24.932524, -80.621399 - **Google Maps:** https://www.google.com/maps?q=24.932524,-80.621399 ## Listing Agent - **Name:** Natalie Biondoletti · **License:** 3381352 - **Brokerage:** Coastal Realty of the Florida - **Broker Phone:** (305) 664-0077 - **Listing URL:** [View original listing](https://www.realtor.com/realestateandhomes-detail/Overseas-Hwy_Upper-Matecumbe-Key-Islamorada_FL_33036_M95460-33231?f=listhub&s=FLKEYSMLSFL&m=621407&c=propsimple) ## Photos ![Overseas Highway - Photo 1](http://lh.rdcpix.com/cadbe0d0dcb713e481407ddfce57b54al-f3294440888r.jpg) ![Overseas Highway - Photo 2](http://lh.rdcpix.com/cadbe0d0dcb713e481407ddfce57b54al-f2946977741r.jpg) ![Overseas Highway - Photo 3](http://lh.rdcpix.com/cadbe0d0dcb713e481407ddfce57b54al-f3721683043r.jpg) ![Overseas Highway - Photo 4](http://lh.rdcpix.com/cadbe0d0dcb713e481407ddfce57b54al-f1961066184r.jpg) ![Overseas Highway - Photo 5](http://lh.rdcpix.com/cadbe0d0dcb713e481407ddfce57b54al-f885424219r.jpg) ![Overseas Highway - Photo 6](http://lh.rdcpix.com/cadbe0d0dcb713e481407ddfce57b54al-f2933015876r.jpg) ![Overseas Highway - Photo 7](http://lh.rdcpix.com/cadbe0d0dcb713e481407ddfce57b54al-f780689187r.jpg) ![Overseas Highway - Photo 8](http://lh.rdcpix.com/cadbe0d0dcb713e481407ddfce57b54al-f915552326r.jpg) ![Overseas Highway - Photo 9](http://lh.rdcpix.com/cadbe0d0dcb713e481407ddfce57b54al-f2721614333r.jpg) --- **MLS#:** 621407 | **Updated:** 2026-10-22 **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/overseas-highway-upper-matecumbe-key-islamorada-fl-33036-83f87f13c33a408da859830bd69197c0) --- ## Structured Data ```json { "@context": "https://schema.org", "@type": "RealEstateListing", "@id": "https://www.propertysimple.ai/listing/overseas-highway-upper-matecumbe-key-islamorada-fl-33036-83f87f13c33a408da859830bd69197c0#listing", "url": "https://www.propertysimple.ai/listing/overseas-highway-upper-matecumbe-key-islamorada-fl-33036-83f87f13c33a408da859830bd69197c0", "name": "Overseas Highway, Upper Matecumbe Key Islamorada, FL 33036", "description": "A rare opportunity to own an expansive bayfront parcel at Mile Marker 81 on Upper Matecumbe Key, offered for sale for the first time since its acquisition in 1937. Located in the heart of Islamorada, this remarkable property encompasses approximately 5.26 total deeded acres, including approximately 2.84 acres of upland, with more than 250 feet of frontage on Florida Bay. The substantial acreage and natural setting offer exceptional privacy and seclusion, while still being close to the restaurants, marinas, shops, galleries, and world-class boating and fishing that define the Islamorada lifestyle. With its coveted Upper Matecumbe Key location, expansive bayfront, and rare parcel size, this is an extraordinary opportunity to create a private waterfront estate in the Florida Keys. Zoned Native Residential (NR), allowing single-family residential use subject to applicable Village requirements. Allowable clearing, building area, and development potential are subject to applicable Village of Islamorada regulations. Buyer to independently verify all development potential with the Village of Islamorada.", "image": [ "http://lh.rdcpix.com/cadbe0d0dcb713e481407ddfce57b54al-f3294440888r.jpg", "http://lh.rdcpix.com/cadbe0d0dcb713e481407ddfce57b54al-f2946977741r.jpg", "http://lh.rdcpix.com/cadbe0d0dcb713e481407ddfce57b54al-f3721683043r.jpg", "http://lh.rdcpix.com/cadbe0d0dcb713e481407ddfce57b54al-f1961066184r.jpg", "http://lh.rdcpix.com/cadbe0d0dcb713e481407ddfce57b54al-f885424219r.jpg", "http://lh.rdcpix.com/cadbe0d0dcb713e481407ddfce57b54al-f2933015876r.jpg", "http://lh.rdcpix.com/cadbe0d0dcb713e481407ddfce57b54al-f780689187r.jpg", "http://lh.rdcpix.com/cadbe0d0dcb713e481407ddfce57b54al-f915552326r.jpg", "http://lh.rdcpix.com/cadbe0d0dcb713e481407ddfce57b54al-f2721614333r.jpg" ], "primaryImageOfPage": { "@type": "ImageObject", "url": "http://lh.rdcpix.com/cadbe0d0dcb713e481407ddfce57b54al-f3294440888r.jpg", "caption": "Overseas Highway - Upper Matecumbe Key Islamorada, FL" }, "datePosted": "2026-09-25", "dateModified": "2026-10-22T00:22:22.376Z", "mainEntity": { "@type": "Place", "@id": "https://www.propertysimple.ai/listing/overseas-highway-upper-matecumbe-key-islamorada-fl-33036-83f87f13c33a408da859830bd69197c0#property", "name": "Overseas Highway, Upper Matecumbe Key Islamorada, FL 33036", "address": { "@type": "PostalAddress", "streetAddress": "Overseas Highway", "addressLocality": "Upper Matecumbe Key Islamorada", "addressRegion": "FL", "postalCode": "33036", "addressCountry": "US" }, "geo": { "@type": "GeoCoordinates", "latitude": 24.932524, "longitude": -80.621399 }, "image": [ "http://lh.rdcpix.com/cadbe0d0dcb713e481407ddfce57b54al-f3294440888r.jpg", "http://lh.rdcpix.com/cadbe0d0dcb713e481407ddfce57b54al-f2946977741r.jpg", "http://lh.rdcpix.com/cadbe0d0dcb713e481407ddfce57b54al-f3721683043r.jpg", "http://lh.rdcpix.com/cadbe0d0dcb713e481407ddfce57b54al-f1961066184r.jpg", "http://lh.rdcpix.com/cadbe0d0dcb713e481407ddfce57b54al-f885424219r.jpg", "http://lh.rdcpix.com/cadbe0d0dcb713e481407ddfce57b54al-f2933015876r.jpg", "http://lh.rdcpix.com/cadbe0d0dcb713e481407ddfce57b54al-f780689187r.jpg", "http://lh.rdcpix.com/cadbe0d0dcb713e481407ddfce57b54al-f915552326r.jpg", "http://lh.rdcpix.com/cadbe0d0dcb713e481407ddfce57b54al-f2721614333r.jpg" ], "identifier": { "@type": "PropertyValue", "propertyID": "MLS", "value": "621407" }, "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": "5.27 acres" }, { "@type": "PropertyValue", "name": "Property Subtype", "value": "Other" }, { "@type": "PropertyValue", "name": "Property Type", "value": "Land" } ] }, "offers": { "@type": "Offer", "@id": "https://www.propertysimple.ai/listing/overseas-highway-upper-matecumbe-key-islamorada-fl-33036-83f87f13c33a408da859830bd69197c0#offer", "url": "https://www.propertysimple.ai/listing/overseas-highway-upper-matecumbe-key-islamorada-fl-33036-83f87f13c33a408da859830bd69197c0", "price": 3500000, "priceCurrency": "USD", "businessFunction": "http://purl.org/goodrelations/v1#Sell", "availability": "https://schema.org/InStock", "seller": { "@id": "https://www.propertysimple.ai/listing/overseas-highway-upper-matecumbe-key-islamorada-fl-33036-83f87f13c33a408da859830bd69197c0#agent" } }, "provider": { "@type": "Person", "@id": "https://www.propertysimple.ai/listing/overseas-highway-upper-matecumbe-key-islamorada-fl-33036-83f87f13c33a408da859830bd69197c0#agent", "name": "Natalie Biondoletti", "worksFor": { "@type": "Organization", "@id": "https://www.propertysimple.ai/listing/overseas-highway-upper-matecumbe-key-islamorada-fl-33036-83f87f13c33a408da859830bd69197c0#brokerage", "name": "Coastal Realty of the Florida", "telephone": "(305) 664-0077", "logo": { "@type": "ImageObject", "url": "http://lh.rdcpix.com/dde52e81b82311e7a5f60242ac110004k-c1005535109r.png" } } } } ```