By Christopher R. Gabriel, PA, REALTOR, eXp Realty | Updated November 4, 2026
Cover image: AI-generated illustration of a Florida home with American and Florida flags.
Moving to Orlando starts with matching the home to the life you want to live: your work location, daily travel, outdoor space and ownership budget. If Central Florida is already on your shortlist, begin now with a realistic closing and move-in calendar. Buyers considering a 2026 move should also review the December 31 residency provision in Amendment 3 before making assumptions about future homestead benefits. [1]
Choose your daily routine before your floor plan
Build a shortlist around the places you actually need to reach. Compare Windermere and Winter Garden homes against the same requirements: an office, garage capacity, pool, maintenance needs and your routes to work or appointments. If Lake Nona or another part of Orlando is your destination, test that trip at the times you expect to travel. A map distance alone does not establish a reliable commute.
Turn a year-end goal into a workable calendar
Discuss financing, inspections, insurance, title work and possession together. Ask whether a resale home can be delivered vacant on your schedule. For new construction, confirm the builder's current completion estimate and the contract's timing provisions. Keep room for delays so the deadline supports your planning without pushing you into a home that does not fit.
Understand the residency milestone
The amendment distinguishes people maintaining permanent Florida residence by December 31, 2026 from later arrivals. Its expanded exemption is not awarded merely because you sign a contract. Review your circumstances with the property appraiser before relying on a tax benefit. [1]
Prepare the homestead application with the move
For 2027, plan to own and occupy the qualifying permanent home by January 1 and apply by March 1. The appraiser may ask for a Florida driver license, vehicle registration, domicile information or other residency evidence. Buying a home and establishing permanent residence are related but separate steps. [2]
Compare the whole monthly ownership cost
Request a buyer-specific tax estimate because a sale may lead to reassessment. Add your loan payment, insurance quote, HOA or condominium fees, utilities and upkeep. Compare actual properties using the same assumptions. Review association documents and planned assessments, and verify which costs are included in a new-construction quote. [3]
Your purchase checklist
- Set a purchase budget and confirm financing or proof of funds.
- Shortlist homes by daily travel, layout and maintenance needs.
- Confirm inspections, insurance, closing and possession dates.
- Check residency evidence and homestead filing with the appraiser.
Buyer questions, answered
Should I rent first or buy before relocating?
Base that decision on your familiarity with the area, available homes and timeline. Renting can allow time to test a location; a purchase can work when the home and schedule are well matched.
Can a new-construction home meet my move date?
Possibly. Verify the specific home's status, contract terms and occupancy timing. Treat an estimated completion date as an estimate.
How should I compare Windermere and Winter Garden?
Use your own priorities and property-level costs. Tour both, test your regular journeys and compare homes with similar features and condition.
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About Christopher Gabriel
Christopher R. Gabriel, PA | REALTOR, eXp Realty. Helping buyers with Central Florida relocation, luxury homes, second homes and Disney-area rental properties.
More in this Florida homebuying series
- Florida Amendment 3 Passes: Homestead Exemption Changes for 2027 and 2028
- Buying a Second Home in Central Florida: Costs, Location and Ownership
- Buying a Central Florida Rental Property: A Long-Term Investor's Guide
- Buying a Vacation Home Near Disney: Personal Use and Short-Term Rentals
Sources
Checked November 4, 2026.
- Florida Department of State: Amendment 3 ballot summary
- Florida Department of Revenue: homestead application requirements
- Florida Statutes: reassessment after ownership changes
General information. Confirm current rules and property-specific eligibility with the responsible authority.