Premier Brokers International
74049 Overseas Highway, Islamorada, FL 33036
ActiveMLS listing sourceMIAMI REALTORS® MLS
ActiveMLS® A12064940
$3,850,000

74049 Overseas Highway, Islamorada, FL 33036

Beds
4
Baths
4
Sqft
2,596
Est. payment$23,924/mo
Home type
Single Family Residence
Year built
1970
Lot size
21,780 sqft
Price / sqft
$1,483
HOA
$0/mo
Community
LOWER MATECUMBE BEACH

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.

Listing activity

Days on market
52
Listed
Aug 6, 2026
MLS listing updated
Sep 27, 2026
Feed last checked
8 minutes ago

Listed by Kimberly Farias · Luxe Properties

Map

Map location is based on MLS-supplied coordinates. Verify the location before relying on it.

Facts & features

Interior

Bedrooms & bathrooms

Bedrooms
4
Bathrooms
4
Bathrooms (decimal)
4
Full bathrooms
4
Half bathrooms
0

Rooms & features

Rooms
1
Flooring
Tile
Appliances
Dishwasher, Dryer, Electric Range, Microwave, Refrigerator, Washer

Heating & cooling

Heating
Central
Cooling
Central Air
Property

Parking

Garage spaces
0
Carport spaces
1
Carport
Yes
Covered spaces
1
Parking features
Driveway
Attached garage
No

Exterior

Stories
2
Building area
5,054 sqft
Patio & porch
Patio
Exterior features
Balcony
Fencing
Fenced
Pool
Yes
Pool features
In Ground
View
Ocean, Direct Ocean, Pool
Waterfront
Other, Ocean Access, Ocean
Waterfront property
Yes

Lot

Lot size
21,780 sqft
Lot size (acres)
0.5 acres
Zoning
SINGLE FAMILY RESID
Construction

Type & style

Home type
Single Family Residence
Year built
1970
New construction
No

Materials

Construction
CBS
Roof
Metal
Property condition
Resale
Levels
Two
Faces
Northwest
Utilities & green energy

Utilities

Sewer
Public Sewer
Water
Public
Community & HOA

Community

Subdivision
LOWER MATECUMBE BEACH
MLS area
5940 - Other Florida County
MLS subarea
Other
55+ community
No

Association

Has association
No
Estimated monthly dues
$0
Amenities
Other
Lease details

Not reported by the listing source.

Location

Area details

City
Islamorada
County
Monroe
ZIP code
33036
Manufactured home details

Not reported by the listing source.

Financial & listing details

Listing

MLS number
A12064940
Possession
Negotiable
Original list price
$3,850,000
Parcel number
00389650000000
Annual property tax
$24,268
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
Additional MLS details

Reported by the listing source

Association Amenities
Other
Association
No
Bathrooms Total Decimal
4
Bathrooms Total Integer
4
Building Area Total
5054
Construction Materials
CBS
County Or Parish
Monroe
Days On Market
52
Direction Faces
Northwest
Elementary School
Plantation Key
High School
Coral Shores
List Price
3850000
Listing Contract Date
2026-08-06
Living Area
2596
Lot Size Acres
0.5
Lot Size Area
21600
MLSArea Major
5940 - Other Florida County
MLSArea Minor
Other
Middle Or Junior School
Plantation Key
Mls Status
Active
On Market Date
2026-08-06
Patio And Porch Features
Patio
Photos Count
72
Postal Code
33036
Property Sub Type
Single Family Residence
Property Type
Residential
Rooms Total
1
Senior Community
No
Standard Status
Active
State Or Province
FL
Status Change Timestamp
2026-08-06T04:00:00Z
Stories Total
2
Subdivision Name
LOWER MATECUMBE BEACH
Water Source
Public
Waterfront Features
Other, Ocean Access, Ocean
Tax Annual Amount
24268
Bathrooms Full
4
Pool Private
Yes
Bedrooms Total
4
Bathrooms Half
0

Market value

Automated estimate—No licensed valuation source connected
Estimated sales range—Ask Karim for a local market analysis
Estimated rent—No licensed rental valuation source connected

Price history

DateEventPrice
Aug 6, 2026ListedMIAMI REALTORS® MLS$3,850,000$1,483/sqft

Public tax history

YearProperty taxesAssessment
2025$24,268—

Payment calculator

Estimated monthly payment$23,924/moIllustrative estimate, not a loan offer.
Principal & interest
$19,977
Property taxes
$2,022
Insurance
$1,925
Association dues
$0

Live national rate context is displayed below through Mortgage News Daily’s official widget. The calculator rate remains a separate assumption until licensed machine-readable access is connected. This is not a loan offer.

Neighborhood

Area

LOWER MATECUMBE BEACH

Islamorada · Monroe County · 33036

Climate risk

—

No licensed climate-risk source is connected.

Nearby schools

Plantation KeyElementary
—
Plantation KeyMiddle
—
Coral ShoresHigh
—
School names and districts are MLS-reported when available. Verify attendance boundaries with the school district. Ratings require a licensed ratings provider.

Nearby homes

12 homes

Similar homes

12 homes
MLS listing source

MIAMI REALTORS® MLS · Listing courtesy of Luxe Properties. All listings featuring the BMLS logo are provided by BeachesMLS, Inc. This information is not verified for authenticity or accuracy and is not guaranteed. Copyright ©2026 BeachesMLS, Inc. IDX information is provided exclusively for consumers’ personal, non-commercial use and may be used only to identify prospective properties they may be interested in purchasing or leasing. Terms of use · Equal Housing Opportunity.