Picture this: while friends back home are scraping ice off their windshields, you’re having coffee on your lanai, planning a lazy day on the lake or a morning walk through downtown Winter Garden. If you’ve been dreaming about a second home in Florida, West Orange County deserves a close look.
Winter Garden, Windermere, Montverde, Dr. Phillips, and Horizon West offer a rare mix of small-town charm, lake living, and easy access to Orlando’s world-famous attractions. Here’s why so many second-home buyers choose this corner of Central Florida, plus what to know about costs and upkeep before you buy.
Mild Winters and Plenty of Sunshine
Central Florida’s winters are a big draw. Orlando’s normal January high is about 72°F, with lows near 50°F, according to the National Weather Service. That’s ideal weather for golf, biking, boating, and dining outdoors.
Summers are hot and humid, with normal July highs around 92°F and frequent afternoon thunderstorms. Many second-home owners plan most of their visits for the drier months from fall through spring.
Close to the Theme Parks, Without Living in Tourist Traffic
West Orange County puts you close to the action while giving you a quieter home base. From Windermere, Walt Disney World is typically a 10- to 20-minute drive, and Orlando International Airport is about 25 to 35 minutes away. Universal Orlando and SeaWorld are a short drive east.
Having your own home nearby means you can split park days across several trips, skip resort pricing, and come home to a full kitchen and your own pool instead of a hotel room.
Small-Town Charm and an Outdoor Lifestyle
- Downtown Winter Garden: Historic Plant Street is lined with restaurants, shops, and a popular Saturday farmers market.
- The West Orange Trail: This paved trail runs 22 miles through Oakland, Winter Garden, and Apopka, and it’s a favorite for biking, walking, and skating.
- Lake living in Windermere: The Butler Chain of Lakes offers boating, paddleboarding, and waterfront homes.
- Nature on Lake Apopka: The Lake Apopka Wildlife Drive is one of the region’s best spots for birdwatching.
- Room to breathe in Montverde: Just over the Lake County line, Montverde offers rolling hills and a quieter, rural feel.
- New communities in Horizon West: Newer master-planned neighborhoods offer modern homes, parks, and shopping close by.
What to Know About Costs and Taxes
Owning a second home in Florida comes with a few rules that surprise out-of-state buyers. Talk with a tax professional about your situation, but here are the basics:
- State income tax: Florida doesn’t have a personal state income tax, but that benefit applies to Florida residents. If your primary home is in another state, you’ll generally still owe income tax there.
- Property taxes: Second homes don’t qualify for Florida’s homestead exemption. For non-homestead residential property, annual increases in assessed value are capped at 10 percent for most taxes, though the cap doesn’t apply to school taxes. Paying your bill in full in November earns a 4 percent discount.
- Insurance: Budget for homeowners insurance with wind coverage, and ask about flood insurance, which standard policies don’t include.
- HOA fees: Many West Orange County neighborhoods have homeowners associations with monthly or annual dues and community rules.
- Renting it out: If you plan to rent your home short-term, check city, county, and HOA rules before you buy. Florida also charges sales tax and local tourist development tax on rentals of six months or less.
Plan for Upkeep from Day One
Florida’s heat, humidity, and storm season mean an empty home needs regular attention. Keep the AC running, keep humidity at or below 60 percent, and have a hurricane plan in place before June 1. Our Florida Vacation Home Maintenance guide walks through what to check each season.
Your Next Steps
- Visit in different seasons: Rent in a few neighborhoods first to see what fits your lifestyle.
- Work with a local real estate agent: Choose someone who knows vacation properties, HOA rules, and the local market.
- Line up help before closing: Plan who will prepare the home before your first visit and look after it while you’re away.
Homes & Living Collective helps new owners settle in with relocation and pre-arrival home prep, then keeps your home cared for with weekly home watch and vacation home management in Winter Garden, Windermere, Montverde, Dr. Phillips, and nearby communities. Schedule a free consultation to learn more.
Keep reading: How to Manage a Florida Vacation Home from Afar: 10 Essential Tips and How to Choose the Right Vendors for Your Central Florida Vacation Home.
West Orange County Vacation Home FAQs
Walt Disney World is typically a 10- to 20-minute drive from Windermere, depending on where you are in town and traffic. Orlando International Airport is about 25 to 35 minutes away.
Winters are mild. Orlando’s normal January high is about 72°F, with lows near 50°F, according to the National Weather Service. Summers are hot and humid, with frequent afternoon storms.
No. Florida’s homestead exemption applies only to your permanent primary residence. Second homes are taxed as non-homestead property, with annual assessed-value increases capped at 10 percent for most taxes, excluding school taxes.
It depends on your city, county zoning, and HOA rules, so check before you buy. Rentals of six months or less are also subject to Florida sales tax and local tourist development tax.
Homes & Living Collective provides weekly home watch visits, maintenance coordination, hurricane prep, and pre-arrival home prep for vacation homes in Winter Garden, Windermere, Montverde, Dr. Phillips, and nearby communities. Schedule a free consultation to get started.
About the Author
Nicole Mickle is the founder of Homes & Living Collective. With more than 20 years in the real estate industry, including work as a mortgage broker, loan officer, transaction coordinator, and founder of a mobile notary closing company, she helps homeowners in Winter Garden, Windermere, Montverde, Dr. Phillips, and nearby communities keep their homes cared for, whether they live here full time or visit a few times a year.
