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$3,850,000
74049 Overseas Highway
Islamorada, FL 33036
MLS# A12064940
4 beds  |  4 baths  |  5054 sqft


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Open House (09/26/2026 - 12:00 pm - 2:00 pm)

Property 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 offers a handicap-friendly layout, with a 1 additional bedroom, 1 bathroom, a cabana bath, and a second full kitchen. Step outside to your private pool, then take just a few steps to your own private beach, creating the ultimate island experience. A new A/C system and metal roof also adds comfort and peace of mind. Conveniently located just minutes from Robbie's Marina and Theater of the Sea, you'll enjoy world class fishing, boating, snorkeling, waterfront dining, and everything that makes Islamorada one of the premier destinations in the Florida Keys.

Details
Maps
Contract Information
Comp Sale YN: No
Occupant Type: Tenant
Listing Date: 2026-08-06
Status: Active
Original List Price: 3850000
List Price: $3,850,000
Current Price: $3,850,000
Location and Legal
County Or Parish: Monroe
County Parish Name: Monroe
City Name: Islamorada
Postal Zip: 33036
Geographic Area: Other
Flood Zone: VE,AE
Country: United States
Street Number: 74049
Street Name: Overseas
Street Suffix: Highway
State Or Province: FL
Postal Code: 33036
Postal Code +4: 4203
Subdivision Name: LOWER MATECUMBE BEACH
Area: 5940 - Other Florida County
Elementary School: Plantation Key
Middle Or Junior School: Plantation Key
High School: Coral Shores
Parcel Number: 00389650000000
Zoning: SINGLE FAMILY RESID
General Property Information
Living Area Main: 2596
Lot Size Area: 21600
Water Frontage Feet: 30
Senior Community YN: No
Outdoor Living Spaces YN: Yes
Stories Total: 2
Pool Private YN: Yes
Property Sub Type: Single Family Residence
Bedrooms Total: 4
Bathrooms Total: 4
Bathrooms Full: 4
Building Area Main: 5054
Year Built: 1970
Carport YN: 1
Carport Spaces: 1
Covered Spaces: 1
Lot Size Acres: 0.5
Waterfront YN: 1
Direction Faces: Northwest
Financial Information
Estimated Monthly Assoc Recurring Fee: 0
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
Office/Member Information
DXORIGMLSID: SEF
Amenities
Other: 1
Dining Area
Family/Dining Combination: 1
Flooring
Tile: 1
Leasing Permitted Details
Leasing Permitted YN: Yes
Okay To Lease With Restrictions: 1
Parking Features
Driveway: 1
Property Condition
Resale: 1
Fencing
Fenced: 1
Possession
Negotiable: 1
Sewer
Public Sewer: 1
Special Information
Sold As-Is: 1
View
Pool: 1
Heating
Central: 1
Water Access
Ocean Access: 1
Other: 1
Water View
Direct Ocean: 1
Ocean: 1
Appliances
Dishwasher: 1
Dryer: 1
Electric Range: 1
Microwave: 1
Refrigerator: 1
Washer: 1
Construction Materials
CBS: 1
Levels
Two: 1
Listing Terms
Cash: 1
Conventional: 1
Pool Features
In Ground: 1
Roof
Metal: 1
Water Source
Public: 1
Waterfront Features
Ocean Front: 1
Cooling
Central Air: 1
Showing Requirements
24 Hour Notice: 1
Call Listing Agent: 1
Master Bedroom/Bath
Master Bdrm - Ground: 1
Pool Size Details
Pool Size (WxL): 0
Restrictions
Lease Restrictions: 1
Tax Information
Tax Reflects No Exemptions: 1
Outdoor Living Spaces
Balcony: 1
Patio: 1
Balcony Details
Balcony - Open: 1
Room Types
Garage Converted: 1
Price Calculations
Current Price To SqFt: 1483.05
Section Details
Parcel Number MLX: 1478
Acreage Description
1/2 To Less Than 1 Acre Lot: 1
Status Change Information
Major Change Timestamp: 2026-08-06T04:00:00Z
Major Change Type: New Listing
Status Change Date: 2026-08-06
Originating Details
Originating System Key: 540551817
Originating System ID: M00000151
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
Room Information
Room Name
Garage Converted

IDX
Listing Office: Luxe Properties
Source MLS Verified

Last Updated: September - 23 - 2026

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