Florida Ranked Most Difficult State for Home Sellers

Rising insurance costs and market headwinds have slowed sales for Florida homeowners.

Updated on Oct. 4, 2026 in Residential

Gouache-painted illustration of a single Florida residential home with surrounding palm foliage, representing the current housing market cooling.
Underwood Law Firm has identified Florida as the most challenging state for home sellers, as rising insurance costs significantly cool residential activity. AI Illustration. Upload story photo >

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Underwood Law Firm has ranked Florida as the most challenging state for home sellers, citing a significant slowdown in residential activity. The ranking highlights how high costs and shifting market conditions are impacting homeowners across the state.

Why it matters

Rising property insurance costs, which have doubled over the last five years, combined with higher interest rates, have constrained buyer affordability. These factors have cooled the market, making it more difficult for sellers to close deals quickly.

Pending home sales in the Tampa Bay area have fallen 5.9% year over year, while homes in the region now sit on the market for an average of 70 days. These figures reflect a broader cooling trend as property insurance costs have doubled for many residents over the last five years.

The players

Underwood Law Firm

A legal entity that compiles real estate data to evaluate and compare state housing market performance.

The details

The housing market shift is driven by a convergence of high insurance premiums and property taxes that lower the pool of eligible buyers. As affordability hurdles grow, the frequency of bidding wars seen during the pandemic era has subsided. Some homeowners are now delaying listing their properties until after the November 2026 election, waiting to see the potential outcome of Amendment 3 tax cuts.

Timeline

  1. Property insurance costs in Florida have doubled over the last five years.

  2. Underwood Law Firm released the state housing market rankings in October 2026.

  3. Florida voters will decide on Amendment 3 tax cuts in November 2026.

Money Landscape

The current market slowdown in Florida is occurring against the backdrop of the upcoming Amendment 3 ballot vote. This development highlights how political and fiscal policy uncertainty, paired with structural insurance cost increases, is cooling the state's residential landscape.

Homeowners currently listing property should review local market absorption rates and the impact of insurance premiums on buyer affordability. Before making major sales decisions, consult with a qualified real estate or tax professional regarding how local tax policies like Amendment 3 might shift.

The takeaway

The Florida housing market has entered a period of cooling as insurance costs and affordability pressures persist. Homeowners should track local sales data and plan for potential tax changes in the months ahead by speaking with a professional financial advisor.

What happens next

Florida voters will decide on the potential tax cuts associated with Amendment 3 in November 2026.

Further reading

For more on the current climate for homeowners, see our Residential section.

Source note: This article includes information reported by Spectrum News Bay News 9.

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Do you believe now is a good time to sell a home in your local area?