The Insider
Amendment 3 Passed: What Florida Downsizers Should Do Now
Florida voters approved Amendment 3 (HJR 1-F) on November 3 with about 62% of the vote, based on unofficial results. The homestead exemption on non-school taxes rises to $150,000 in 2027 and $250,000 in 2028. School taxes do not get the larger exemption.
Downsizing within Florida? Save Our Homes and portability did not change, so you can still carry your tax savings to your next home. Moving from out of state? Establish permanent Florida residency by December 31, 2026, or you start at a $50,000 exemption until your fifth year. The Legislature still has to pass implementing details.
Read What Passed & What to Do Next →What's Your Biggest Concern About Downsizing?
Real estate strategies designed for your specific situation, not just the price of your home.
The Tax Trap
You want to move to a smaller home, but your current property taxes are so low that you worry moving will accidentally cause your tax bill to jump.
The 2026 Tax Cutoff
You are moving to Central Florida and need to meet strict year-end residency deadlines to lock in tax savings and avoid big financial penalties.
High Maintenance Costs
You want to swap unused rooms and costly repairs (roof, pool, landscaping) for a modern, easy-to-maintain "lock-and-leave" luxury home.
Our home sold within 24 hours of hitting the MLS — with multiple offers. Yousef's listing, photos, and description did exactly what they needed to do. He was also exceptional at managing us as sellers when the stress got high, and coordinated seamlessly with the agent on our buy side. A true consummate professional. You will not be disappointed.
We closed last week — at a price I didn't expect. And it wasn't easy: the roof needed replacing, the HOA held up approvals, and there were curveballs at every turn. Yousef hit every single one out of the park. In twenty residential transactions over my lifetime, I've never worked with someone this smart and this proactive. If you want a no-B.S. agent who will actually move your property, call Yousef.
He worked magic in a simultaneous closing of three properties — my sale, my purchase of a new home, and the sale of the home my buyers were leaving. My journey with Yousef involved more than just the sale of my house — it included great counseling on downsizing and optimizing the look and feel of the property to maximize yield. Yousef is an energetic, creative, and boundlessly supportive agent I would recommend to anyone seeking a true partner in their real estate transaction. I can't thank him enough.
Find Your Next Home: Low-Maintenance, Lakefront & Gated Communities
KNOW YOUR HOME’SVALUE
See what your home is worth today and exactly how much cash you'll walk away with after taxes and fees.
GET HOME VALUE
PLAN YOUR MOVE& TAX SAVINGS
Map out your moving timeline and keep your low property tax rate so you don't overpay on your next home.
BOOK A CALL
SELL & CLOSEWITH EASE
Protect your sale with clear contracts and skilled negotiation so you sell smoothly for top dollar.
VIEW SELLING STRATEGYComparing Central Florida Neighborhoods? See How They Match Up.
Moving to a new area means comparing local property taxes, home values, and ongoing monthly expenses. If you are weighing your options, see how Dr. Phillips compares to Isleworth, look into Dr. Phillips vs. MetroWest, or view our side-by-side comparison of Dr. Phillips vs. Bay Hill to find the neighborhood that best protects your home equity.
Best Areas to Downsize Near Orlando
Market trends, demand insights, and off-market home listings across Central Florida's premier communities.
Dr. Phillips
Dellagio Town Center dining, Sand Lake Road access, and zero CDD community development taxes.
Isleworth
Deep-water Butler Chain access, 24/7 security guard gate, and total privacy for estate owners.
Winter Park
Walkable Park Avenue shops and dining, historic architecture, and access to top private schools.
Case Studies: How We Sold Them
Every sale starts with a different problem. Here is what two Central Florida sellers were up against, and the plan that got them paid.
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Featured Subdivisions & Neighborhood Profiles
Access local market data, active home listings, CDD fee breakdowns, and neighborhood guides for top communities across Southwest Orlando:
Winter Garden Communities
- Waterleigh Homes in Horizon West
A resort-style master community in Horizon West featuring modern single-family homes with community infrastructure fees (CDD).
- Watermark Homes in Winter Garden
Upscale Craftsman and Mediterranean homes featuring clubhouse amenities near top-rated West Orange public schools.
- Tuscany Homes in Winter Garden
A gated community featuring custom tile-roof homes and private wooded lots with no CDD taxes.
- Orchard Hills Homes in Winter Garden
A family-focused neighborhood located along the Hamlin shopping corridor with low historical property taxes.
Windermere & Butler Chain Neighborhoods
- Windermere Ridge Homes in Orlando
Exclusive gated neighborhood known for mature trees, large custom lots, and high property tax savings potential.
- Lake Down Crest Homes in Windermere
Private waterfront neighborhood with direct boat dock access to Lake Down on the Butler Chain of Lakes.
- Lake Down Cove Homes in Windermere
Gated luxury homes with flexible property rules (no strict HOA) and direct water access.
- Lake Butler Waterfront Homes
Central Florida's top luxury address featuring multi-million dollar custom estates on deep-water lakefront lots.
Southwest Orlando Regional Markets
- MetroWest Homes in Orlando
Established golf course living offering condos, townhomes, and single-family homes with reasonable local tax rates.
- Winter Garden Homes for Sale
Historic downtown charm combined with new luxury homes, offering low-maintenance living options.
- Windermere Homes For Sale
Town-center neighborhoods and private acreage compounds surrounded by Central Florida's famous chain of lakes.
Downsizing in Orlando: Common Questions
What does a downsizing realtor do?
A downsizing realtor plans your sale and your next purchase together. That includes estimating your net proceeds, reviewing your Save Our Homes portability, comparing HOA, CDD and insurance costs, and coordinating both closings. Yousef also helps line up estate sale companies and senior move managers.
What are the best low-maintenance communities for downsizing near Orlando?
Dr. Phillips offers choices like Bay Hill and gated villa communities, and Windermere has waterfront options with smaller homes and lots. Winter Park has condos and townhomes near Park Avenue, and Winter Garden has newer single-story homes and 55+ options. The best fit depends on your HOA, CDD and tax costs.
How much does it cost to downsize in Orlando?
As an estimate, a $500,000 sale and $400,000 purchase often cost about $44,400 to $90,900 in total, or 9% to 18% of the sale price. That includes commissions, closing costs, prep, moving and any retrofits. Yousef's free report estimates your own home value and net proceeds.
How do I keep my property tax savings when I downsize in Florida?
Save Our Homes portability can move up to $500,000 of your savings to your next Florida homestead. Moving to a lower-priced home transfers the same percentage of your savings, not the full dollar amount. You generally have until January 1 of the third year after leaving your old homestead, and you must file Form DR-501T with your homestead application.
How does Amendment 3 affect downsizing in Florida?
Based on unofficial results, voters approved Amendment 3 on November 3, 2026. The non-school homestead exemption rises to $150,000 in 2027 and $250,000 in 2028. School taxes do not get the larger exemption, and Save Our Homes portability did not change. Confirm the details with your CPA or property appraiser.
Can I sell my house and buy a smaller one at the same time?
Yes. Buying and selling at the same time takes careful scheduling and clear contract terms. Drawing on 10+ years of United Nations negotiation experience, Yousef coordinates both closings around your timeline, and options like a rent-back, bridge loan or HELOC can help you avoid moving twice.
What should I know before buying a waterfront home in Windermere?
Buying on the Butler Chain of Lakes requires understanding dock rights, environmental rules, and waterfront valuation trends.