November 3, 2026: Florida Amendment 3 is on the ballot. Rentals do not get the new homestead exemption.County impact →

Orange County · Table 5 · 2028 model

Winter Park rental holding costs and Amendment 3

People searching “is it worth buying a rental in Winter Park” need tax, millage, and insurance — not a slogan. Below are the cited figures. We do not declare this market a buy.

· · Figures retrieved 2026-10-18

Amendment 3 modeled 2028 tax (Table 5)

TypeAdditional taxPercent
Apartment unit$36811.88%
Single-family rental$1,57211.05%

Walczak Table 5 · county-level Table 4 is on the Orange Amendment 3 page.

Millage used for a purchase-year tax sketch

Our extract of the Orange millage sheet does not include a published Winter Park citywide total, so we do not invent one. The calculator default below is the county example (16.1366 mills — Unincorporated Orange County, mill code 10). Replace it with the TRIM millage for the parcel.Orange County Property Appraiser, 2025 Final Millage Rates.

OIR homeowners-with-wind average for Orange as of 2025-09-30: $3,585. That is a labeled placeholder, not a Winter Park DP-3 quote.Insurance page.

Is it worth buying a rental in Winter Park?

This site does not rate Winter Park as a buy or a pass. Worth depends on rent, millage, insurance, flood, and HOA on the specific parcel. Walczak Table 5 models $1,572 (11.05%) additional 2028 tax on the average Winter Park single-family rental if millage is raised to replace homestead revenue — an assumption, not a forecast.

Does a Winter Park rental get the Amendment 3 homestead exemption?

No. Homestead is for a permanent resident’s primary home. Source: Pinellas County Property Appraiser Amendment 3 FAQs.

Calculator starting from Orange

If Winter Park millage is in our files, type 16.1366 into the millage field. Label: Unincorporated Orange County, mill code 10 (city total not in our extract; using county example).