Estate Planning in Key West: the Local Picture
Key West and the Florida Keys are a unique, high-value market of retirees, second-home owners, and seasonal residents spread along the island chain. A high-value island market where second homes, homestead, domicile, and probate avoidance all matter, often for owners who also keep a home up north.
A home at that value sits well above Florida’s $150,000 summary-administration threshold, raised from $75,000 on July 1, 2026, so without planning it can pull your family into a full, months-long probate. The fix is to coordinate the home, the will or trust, and any deed together, so the house passes the way you intend.
What a Complete Plan Covers
The wills, trusts, and powers of attorney people ask us about in Key West are really one plan in three pieces. A last will and testament names who inherits, a living trust keeps the estate out of probate, and a durable power of attorney covers the years you are still here.
An estate plan is a coordinated set of documents, not one piece of paper. It takes a will or a revocable living trust to direct your property, a durable power of attorney so someone can act if you can’t, and a health-care surrogate, living will, and HIPAA authorization for medical decisions. Homeowners often add a lady bird deed on the homestead. See the full estate-planning guide →
Keeping a Key West Home Out of Probate
Your Florida homestead carries special rules. It generally can’t be left freely in a will if you have a spouse or minor child, and it passes outside the will by its own path. A funded revocable trust or a lady bird deed keeps the home out of probate while you keep full control during life. See Monroe County probate → or find the right deed →
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Book a no-cost consultYour Trust in Key West, Step by Step
2,791 Monroe County homes are held in a family trust, 5.62 percent of the county’s homes, and 881 of them keep a homestead exemption. 31,211 Monroe County parcels belong to an owner with a mailing address in another state, and 324 more to an owner abroad. An owner who lives elsewhere is the one a trust helps most, because a Florida house otherwise needs a second probate here. The Monroe County court opened 346 new probate cases in the 2024 to 2025 court year. A home held in a trust passes to the family without adding to that count.
- 1Monroe County Clerk of the Circuit Court and Comptroller, Key West office (Recording), 500 Whitehead Street, Key West, FL 33040. Directions
- 2Monroe County Clerk, Marathon office, 3117 Overseas Highway, Marathon, FL 33050 (a drive, not on the map). Directions
- 3Monroe County Clerk, Plantation Key office, 88770 Overseas Highway Suite 2, Tavernier, FL 33070 (a drive, not on the map). Directions
- 4Monroe County Property Appraiser, Key West office, 500 Whitehead Street, Key West, FL 33040. Directions
- 5Monroe County Property Appraiser, Marathon office, 2798 Overseas Hwy, Suite 310, Marathon, FL 33050 (a drive, not on the map). Directions
- 6Monroe County Property Appraiser, Plantation Key office, 88700 Overseas Hwy, Plantation Key, FL 33036 (a drive, not on the map). Directions
- 7The UPS Store Key West #1471, 2900 N Roosevelt Blvd, Ste 1107, Key West, FL 33040 (a drive, not on the map). Directions
- 8Key West Post Office, 400 Whitehead St, Key West, FL 33040. Directions
- 9First Horizon Bank, Key West branch, 330 Whitehead St, Key West, FL 33040. Directions
- 10Centennial Bank, Key West branch, 701 Whitehead St, Key West, FL 33040. Directions
- 11First State Bank, 1201 Simonton St, Key West, FL 33040. Directions
- 12Cuban Coffee Queen Downtown, 5 Key Lime Square, Key West, FL 33040. Directions
- 13Fausto’s Food Palace, 522 Fleming Street, Key West, Florida 33040. Directions
- 14Old Town Parking Garage (Park n’ Ride), 301 Grinnell Street, Key West, FL 33040. Directions
- 15Mallory Square, Mallory Square, Key West, FL 33040. Directions
- 16Monroe County Veterans Affairs, Key West office (Gato Building), 1100 Simonton Street 1-190, Key West, FL 33040. Directions
- 17Monroe County Tax Collector driver license office, Key West, 1200 Truman Avenue, Suite #101, Key West, FL 33040. Directions
- 18Florida Department of Health in Monroe County, Vital Statistics (Gato Building), 1100 Simonton St., Gato Building, Key West, FL 33040. Directions
Signing your trust in Key West, with two witnesses and a notary
A Florida trust that leaves your home or savings to someone at your death has to be signed the way a will is signed, with two witnesses who watch you sign and a notary. Florida law voids the parts of a trust that pass property at death when they are signed without those formalities, and Florida courts have thrown out trust amendments that carried one witness instead of two. We run the signing with our own witnesses and notary, by video or in person. If you would rather sign locally, these are the places nearby.
A Florida deed needs two witnesses and a notary. We set up the signing for you by video, so a homeowner who spends part of the year up north can sign from wherever the winter finds them. If you would rather sign in person, The UPS Store Key West (store #1471) at 2900 N Roosevelt Blvd, Ste 1107, in the Kmart Shopping Plaza by the new Publix, lists notary service seven days a week along with printing and faxing, at (305) 292-4177. The store is on the Roosevelt Boulevard side of the island, a short drive from Old Town rather than a walk.
The Monroe Clerk posts its own recording checklist. The deed needs a title, the name and address of the person who prepared it, original signatures with a notary’s seal, and two witnesses whose full addresses are written under their signatures. The Clerk adds $1 for each name to be indexed after the first four, and a deed sent by mail needs a self-addressed stamped envelope large enough for its return. When we draft and e-record your deed, those details are handled.
If you are in Old Town on a weekday anyway, the everyday errands sit within a few blocks of the Clerk’s office on Whitehead Street. The Key West Post Office is at 400 Whitehead Street, about 4 minutes on foot, open weekdays from 8:30 a.m. to 5 p.m. and Saturday from 9:30 a.m. to noon, at 305-294-9539. For a cashier’s check, if you bank there, First Horizon has a branch at 330 Whitehead Street and Centennial Bank has one at 701 Whitehead Street, each about 5 minutes on foot. First State Bank, which the FDIC lists as a Key West bank established in 1955, has its main office at 1201 Simonton Street, about 18 minutes on foot.
For hot coffee, Cuban Coffee Queen Downtown is at 5 Key Lime Square, where Southard meets Duval, about 5 minutes on foot. The shop serves coffee in an enclosed courtyard under shade trees, open daily from 7 a.m. to 7 p.m., at (305) 294-7787, and its roasting operation sits steps away in a converted old-time barbershop. For groceries or lunch to take home, Fausto’s Food Palace at 522 Fleming Street is about 5 minutes on foot, open every day from 7:30 a.m. to 7 p.m., at 305-296-5663. Fausto’s says it was established in 1926 and calls itself the oldest running Key West business.
If you drive to the Clerk’s office yourself, the city’s Old Town Parking Garage (the Park n’ Ride) is at 301 Grinnell Street, at the corner of Caroline and Grinnell, about 15 minutes on foot from the Clerk’s office. The garage is open 24 hours except during evacuations and charges $6 an hour or $48 a day plus tax, and paying there lets everyone in your car ride the city’s Key West bus routes free for the day. The bus stop is across Caroline Street in front of West Marine.
The streets around the Clerk’s office carry their own history. The Great Fire of 1886 started next to the San Carlos Institute on Duval Street, burned for 12 hours and tore through blocks of Fleming, Whitehead, Eaton, Duval and Simonton streets, destroying 18 cigar factories and 614 houses and other buildings, according to the city’s own history page. After an errand, Mallory Square on the water is about 9 minutes on foot, the ground where Commodore David Porter based an anti-piracy squadron in 1823 and where salvaged cargo from shipwrecks was later stored and auctioned.
Putting your Key West home into the trust
Putting your home into the trust means recording a new deed, from you to yourself as trustee, in Monroe County’s official records. The trust deed is recorded at the same office, and in the same way, as any other deed.
In Monroe County, deeds are recorded by the Clerk of the Circuit Court and Comptroller, Kevin Madok, and the main office is in Old Town at 500 Whitehead Street in Key West. The Clerk’s offices are open Monday through Friday from 8:30 a.m. to 5 p.m. The Recording Division answers at 305-292-3540, and deeds sent by mail go to the Monroe County Clerk of the Court, Attn. Recording, at the same Whitehead Street address.
The Clerk keeps two more offices up the Overseas Highway, one at 3117 Overseas Highway in Marathon (305-289-6027) and one at 88770 Overseas Highway, Suite 2, in Tavernier on Plantation Key (305-852-7145). The Clerk tells anyone with a time-sensitive document to record it in person at one of its office locations.
You will not need to go to any of them. We record your deed electronically through Simplifile, which is first on the Monroe Clerk’s own list of e-recording vendors, so the signed original never has to travel down the Overseas Highway by mail. The Clerk says plainly that it cannot guarantee a document is recorded on the day it arrives. The Clerk posts the recording fee as $10 for the first page and $8.50 for each page after, so a two-page deed costs $18.50 to record.
Keeping the homestead exemption with the home in a trust
A home held in your revocable trust keeps its homestead exemption when the trust gives you a lifetime interest in the home, which is how we draft it. The Property Appraiser still asks for proof of the trust, and each county asks for something slightly different, so here is what this one wants.
Homestead is handled by Scott P. Russell, the Monroe County Property Appraiser, whose Key West office is in the same building as the Clerk, at 500 Whitehead Street, open weekdays from 8 a.m. to 5 p.m., at 305-292-3420. The Property Appraiser also has offices at 2798 Overseas Hwy, Suite 310, in Marathon (305-289-2550) and at 88700 Overseas Hwy on Plantation Key (305-853-7353), and you can apply at any of the three. You can also file online after registering for an account, and the office is taking applications for 2027 now. Applications are due by March 1, and an application received after that date is treated as a prefile for the following year.
Many Key West homeowners live somewhere else for part of the year, and the Property Appraiser’s rules speak to that directly. To qualify, you must hold title on January 1, have made Monroe County your legal domicile, and live on the property. The Property Appraiser asks you to show that neither you nor your spouse receives a residency-based exemption on any other property, and warns that changing your voter registration from Monroe County to another county or state will affect your homestead. Renting out all or substantially all of the home counts as abandoning the homestead, although renting after January 1 does not cost you that year’s exemption unless the home is rented for more than 30 days a year for two years in a row. The office also warns that an owner who fails to report a change in status can be back taxed for up to 10 years, with 15 percent interest a year and a 50 percent penalty.
Bring your recorded deed, a Florida driver license and a vehicle registration showing the property address, your Social Security number, and your voter registration card or a Declaration of Domicile. A permanent resident who is not a U.S. citizen must present a Permanent Resident Card and file a Declaration of Domicile, and the Property Appraiser says those documents must be dated before January 1 of the year you apply.
The Monroe Property Appraiser answers the lady bird question in its own FAQ. An owner who transfers the future interest in the home to children and keeps a life estate keeps both the homestead exemption and any existing Save Our Homes value, and a lady bird deed keeps that life estate for you. After your death the exemptions end, the home is reassessed the following year, and a family member who moves in must apply and qualify for a new homestead exemption.
The Property Appraiser also asks owners who add or remove someone from the title, or move the home into a trust, to call and discuss the change, so we suggest a quick call to 305-292-3420 after your deed records. If your home goes into a trust instead, the office asks for a copy of the trust so it can confirm you still qualify.
When the time comes, what your successor trustee does
After your death your successor trustee steps in without a court. Within 60 days the trustee must tell the beneficiaries the trust exists, and Florida law requires a notice of trust to be filed with the court in Monroe County. To sell or transfer the house, the trustee signs a deed as trustee and gives the title company a certification of trust instead of the whole trust.
After you die, the house is already your family’s. To show that in the record, they record a certified copy of your death certificate and an affidavit, and then a title company can insure a sale. The circuit’s own administrative order on recording death certificates tells the Clerk to require the cause-of-death section to be covered before the certificate is recorded, and the same order notes that recording the death certificate is a recognized way to end a life estate. We handle that step.
The Florida Department of Health in Monroe County issues certified death certificates in Key West at its office in the Gato Building, 1100 Simonton Street, about 16 minutes on foot from the Clerk’s office. Vital Statistics is open weekdays from 9 a.m. to 4 p.m. by appointment only, so call 305-293-7500 first. Each certificate is $16, the office issues certificates for Florida deaths from 2009 on, every request needs a photo ID, and the cause of death is released only to family or a legal representative. We prepare and record the rest.
After it records: find it, get a copy, and watch it
We send you the recorded deed as soon as the Clerk returns it. The deed also appears in the Clerk’s official records search, where you can look it up by your name and print a plain copy at home.
If a bank or title company asks for a certified copy, the Clerk’s fee schedule lists $1 a page for the copy and $2 a page for the certification.
Then take two minutes to sign up for the Clerk’s free title monitoring, called Property Fraud Alert, which Fidlar Technologies runs in partnership with Monroe County. You enter your own name or a business name, and the service notifies you whenever a document is recorded under a matching name. The alert does not stop a false deed from being filed, but it gives you an early warning so you can act. For help signing up, the service answers at 800-728-3858.
If you are a veteran with a disability rating
A disabled veteran may qualify for more than the basic homestead exemption, and the proof is a letter from the U.S. Department of Veterans Affairs. The Monroe Property Appraiser lists an exemption of up to $5,000 for an honorably discharged veteran disabled at least 10 percent by service, a full exemption on the homestead for a veteran with a service-connected total and permanent disability, and a property tax discount for a veteran 65 or older with a permanent, combat-related disability. The discount is filed on form DR 501DV with the veteran’s DD Form 214 and the VA rating decision letter. An unremarried surviving spouse can keep some of these exemptions, and service members deployed abroad may qualify for an additional exemption on form DR-501M.
Monroe County Veterans Affairs helps with the paperwork from its Key West office in the historic Gato Building, 1100 Simonton Street 1-190, about 16 minutes on foot from the Clerk’s office. The office is open weekdays from 8 a.m. to 5 p.m. and answers at 305-295-5150.
If your name has changed since you bought the home
Marriage or divorce often leaves a home titled in a name you no longer use. We write the new deed with both names, the name on your old deed and your name today, so the record connects them and a future title search does not stall on the difference.
Your driver license should match as well, because the Property Appraiser asks for a Florida driver license with the property address when you file for homestead. The Florida Department of Highway Safety and Motor Vehicles requires every name change on a license to be made in person at a local office, and only after the Social Security Administration has updated your name, allowing 24 to 48 hours after that. In Key West the driver license office is run by the Monroe County Tax Collector at 1200 Truman Avenue, Suite #101, about 24 minutes on foot from Whitehead Street, open weekdays from 8 a.m. to 4:45 p.m., with all driver license services ending at 4:15 p.m., at 305-295-5000. The Tax Collector adds a service fee to the state’s fees.
Local details checked September 29, 2026 on the offices' and businesses' own sites and Google Maps. Places are listed for convenience, not as a recommendation; call ahead, since hours change. Map data © OpenStreetMap contributors. Trust figures count family trusts on the county’s 2026 roll from the owner name, not counting land trusts (method and county table). County figures from the Florida Department of Revenue 2026 property roll and Data Book and the Florida courts' FY 2024 to 2025 Statistical Reference Guide. Sources: Monroe County Clerk of Court and Comptroller (offices and hours) · Monroe Clerk, Basic Recording Information (e-recording vendors, checklist, fees) · Monroe Clerk, contact directory (Recording Division) · Monroe Clerk, fee schedule · Monroe Clerk, official records search · Property Fraud Alert, Monroe County · Sixteenth Judicial Circuit, AO 2.006, Recordation of Death Certificates · Monroe County Property Appraiser · Monroe County Property Appraiser, contact and offices · Monroe County Property Appraiser, homestead and changes in status · Monroe County Property Appraiser, FAQ (qualifying, documents, life estate, trust, rentals) · Monroe County Property Appraiser, veterans and military exemptions · Monroe County Property Appraiser, online homestead filing · Monroe County Veterans Affairs · FLHSMV name and address changes · FLHSMV Monroe County office locations · Florida Department of Health in Monroe County, death certificates · Florida Department of Health in Monroe County, Administration and Vital Statistics hours · City of Key West, Old Town Parking Garage · City of Key West Fire Department, Our History (the Great Fire of 1886) · City of Key West, History of Mallory Square · Cuban Coffee Queen Downtown · Fausto’s Food Palace · The UPS Store Key West #1471 · USPS Post Office locator · FDIC BankFind, Key West branches · OpenStreetMap foot routing (walking times)
Communities We Serve
We work with families across Monroe County, including Marathon, Islamorada, Key Largo, Big Pine Key, Stock Island, Cudjoe Key, and the rest of Monroe County. Any deed in your plan records with the Monroe County Clerk of the Circuit Court and Comptroller, whose office is at 500 Whitehead Street in Key West; we prepare and e-record it for you. We are a Miami firm serving Key West wherever you are; this is not a Key West office.
Flat Fees
Trust-based plan $3,200 individual / $4,500 couple (trust + pour-over will + durable POA + health-care directives + one funding deed). Will-based plan $1,200 individual / $1,950 couple (will, durable POA, health-care directives and a lady bird deed on the home). Single documents from $299. Government recording costs are additional, at cost. See full pricing →
Frequently Asked Questions
Do you have an office in Key West?
No. StepUpLaw is a Miami firm that serves Key West and Monroe County residents wherever they are, by phone and video. Most of the work happens online, and your signing is coordinated to meet Florida formalities (two witnesses and a notary).
Where are deeds recorded in Monroe County?
Deeds and other documents for a Monroe County property are recorded with the Monroe County Clerk of the Circuit Court and Comptroller. We handle the recording for any deed in your plan and pass the county’s cost through at cost.
Do I need a living trust, or is a will enough?
It depends on what you own and your goals. A will alone still goes through probate; a funded revocable living trust avoids it and manages things if you lose capacity. For a single home passing to your kids, a lady bird deed may be all you need. We talk through both at the no-cost consult.
Updated September 30, 2026. Reviewed by Kevin D. Klagge, Esq., Fla. Bar No. 99502. Attorney Kevin Klagge represents families, businesses, and international clients in estate and tax planning, business structuring, and international law, with a focus on Florida legal tools. He litigates estate and business issues in court. General information about Florida law, not legal advice, and no attorney-client relationship is created. We serve Key West and Monroe County residents from our Miami office. Local figures are Census estimates (ACS 2024) and approximate.