74049 Overseas Highway, Islamorada, FL 33036

New Listing

$3,850,000

Virtual Tour

https://www.zillow.com/view-imx/fd6384c4-b093-40ea-8178-9728687b8973?wl=true&setAttribution=mls&initialViewType=pano

Property Type: Residential Bedrooms: 4 Baths: 4 Square Footage: 5,054 Status: Active

Current Price: $3,850,000 List Date: 8/06/2026 Last Modified: 8/06/2026

Overview

Description

Rare opportunity to own an ocean side single family home in the heart of Islamorada. Situated on a private corner half acre lot with your own private beach, this property offers the space, privacy, and tropical lifestyle that make the Florida Keys one of the most sought-after destinations in the world. Currently operating as a successful VRBO vacation rental, this turnkey, income-producing property is being sold fully furnished, allowing the new owner to seamlessly continue operating it as a successful vacation rental from day one or immediately begin enjoying it as a private island retreat. Designed with flexibility in mind, this two-story home features a total of 4 bedrooms, 4 bathrooms, and two full kitchens. The upper level offers 3 bedrooms, 2 bathrooms, a full kitchen, and a private balcony, while the lower level includes 1 additional bedroom, 1 bathroom, a cabana bath, and a second full kitchen, making it ideal for guests, multi-generational living, or maximizing short term ren ... (Read more)

Listing Details MLS# A12064940

General Property Information

Property Sub Type: Single Family Residence
Bedrooms Total: 4
Bathrooms Total: 4
Bathrooms Full: 4
Building Area Main: 5054
Living Area Main: 2596
Year Built: 1970
Carport YN: Yes
Carport Spaces: Yes
Covered Spaces: Yes
Lot Size Area: 21600
Lot Size Acres: 0.5
Senior Community YN: No
Waterfront YN: Yes
Water Frontage Feet: 30
Outdoor Living Spaces YN: Yes
Stories Total: 2
Direction Faces: Northwest
Pool Private YN: Yes

Property Features

Dining Area: Family/Dining Combination Flooring: Tile Leasing Permitted Details: Okay To Lease With Restrictions Parking Features: Driveway Property Condition: Resale Appliances: Dishwasher; Dryer; Electric Range; Microwave; Refrigerator; Washer Construction Materials: CBS Cooling: Central Air Fencing: Fenced Heating: Central Levels: Two Listing Terms: Cash; Conventional Pool Features: In Ground Possession: Negotiable Restrictions: Lease Restrictions Roof: Metal Sewer: Public Sewer Special Information: Sold As-Is Tax Information: Tax Reflects No Exemptions View: Pool Water Access: Ocean Access; Other Water Source: Public Water View: Direct Ocean; Ocean Waterfront Features: Ocean Front Showing Requirements: 24 Hour Notice; Call Listing Agent Outdoor Living Spaces: Balcony; Patio Balcony Details: Balcony - Open Room Types: Garage Converted Acreage Description: 1/2 To Less Than 1 Acre Lot

Contract Information

Comp Sale YN: No
Original List Price: 3850000
Occupant Type: Tenant

Location and Legal

Country: United States
County Or Parish: Monroe
County Parish Name: Monroe
Street Number: 74049
Street Name: Overseas
Street Suffix: Highway
City Name: Islamorada
State Or Province: FL
Postal Code: 33036
Postal Code +4: 4203
Postal Zip: 33036
Subdivision Name: LOWER MATECUMBE BEACH
Area: 5940 - Other Florida County
Geographic Area: Other
Elementary School: Plantation Key
Middle Or Junior School: Plantation Key
High School: Coral Shores
Parcel Number: 00389650000000
Zoning: SINGLE FAMILY RESID
Flood Zone: VE,AE

Financial Information

Membership Fee Required YN: No
Tax Annual Amount: 24268
Tax Year: 2025
Tax Legal Description: BK 4 LOT 2 & SW'LY 30' OF NE'LY 110' TR B LOWER MATECUMBE BEACH PB3-34 LOWER MATECUMBE OR426-786 OR1368-1165 OR3185-2211 OR3275-1588
Estimated Monthly Assoc Recurring Fee: 0

Status Change Information

Major Change Timestamp: 2026-08-06T04:00:00Z
Major Change Type: New Listing
Status Change Date: 2026-08-06

More Information

Leasing Permitted Details

Leasing Permitted YN: Yes
Okay To Lease With Restrictions: Yes

Price Calculations

Current Price To SqFt: 1483.05

Section Details

Parcel Number MLX: 1478

Originating Details

Originating System Key: 540551817
Originating System ID: M00000151

Office/Member Information

DXORIGMLSID: SEF

Amenities

Other: Yes

Dining Area

Family/Dining Combination: Yes

Flooring

Tile: Yes

Parking Features

Driveway: Yes

Property Condition

Resale: Yes

Fencing

Fenced: Yes

Possession

Negotiable: Yes

Sewer

Public Sewer: Yes

Special Information

Sold As-Is: Yes

View

Pool: Yes

Heating

Central: Yes

Water Access

Ocean Access: Yes
Other: Yes

Water View

Direct Ocean: Yes
Ocean: Yes

Appliances

Dishwasher: Yes
Dryer: Yes
Electric Range: Yes
Microwave: Yes
Refrigerator: Yes
Washer: Yes

Construction Materials

CBS: Yes

Levels

Two: Yes

Listing Terms

Cash: Yes
Conventional: Yes

Pool Features

In Ground: Yes

Roof

Metal: Yes

Water Source

Public: Yes

Waterfront Features

Ocean Front: Yes

Cooling

Central Air: Yes

Showing Requirements

24 Hour Notice: Yes
Call Listing Agent: Yes

Master Bedroom/Bath

Master Bdrm - Ground: Yes

Pool Size Details

Pool Size (WxL): No

Restrictions

Lease Restrictions: Yes

Tax Information

Tax Reflects No Exemptions: Yes

Outdoor Living Spaces

Balcony: Yes
Patio: Yes

Balcony Details

Balcony - Open: Yes

Room Types

Garage Converted: Yes

Acreage Description

1/2 To Less Than 1 Acre Lot: Yes

Room Information

Room Name
Garage Converted

Listing Office: Luxe Properties

Last Updated: August - 06 - 2026

This information is not verified for authenticity or accuracy and is not guaranteed and may not reflect all real estate activity in the market. Copyright 2026 Beaches Multiple Listing Service, Inc. All rights reserved. Information Not Guaranteed and Must Be Confirmed by End User. Site contains live data.

74049 Overseas Highway, Islamorada, FL 33036 (MLS# A12064940)