Why Was Orlando Named The #1 Place to Retire?
With Florida's tax advantages, year-round recreation, warm climate, world-class attractions, easy travel, and a wide range of communities, Southwest Orlando offers an ideal lifestyle that matters most to many retirees. So, it should be no surprise that Orlando was recently named the #1 place to retire in the U.S. by WalletHub. Let's take a closer look at what makes Orlando a top choice for retirees.
What Makes Southwest Orlando a Great Place to Retire?
Location and lifestyle are two of the top reasons people choose Southwest Orlando for their retirement home base. Its Central Florida location makes it easy to travel throughout Florida to the east and west coasts for beaches and cruise ports. Port Canaveral is around 1.5 hours away, making last-minute cruise travel easy and convenient. Proximity to international airports, including Orlando International Airport & Sanford Airport, makes it easy to travel in and out of the area. The Brightline high-speed train station, now located in Orlando, also makes it convenient to travel south to Fort Lauderdale and Miami.
Want to live in a place that family really wants to visit? Try living in Walt Disney World's backyard. For all the reasons SW Orlando is easy to travel out of, it's also easy for friends and family members to visit. The world-class attractions of Disney, Universal, SeaWorld, and beyond make it a no-brainer for families seeking a top destination to visit and explore.
Lifestyle in Southwest Orlando combines the features retirees look for in a home with local connection, plus the amenities and activities they can enjoy more of in retirement. Whether it be golf, pickleball, tennis, trails, fishing, boating, or simply enjoying the sun by a private or community pool, Southwest Orlando is simply unmatched.
What Retirement in Orlando Could Look Like
Retirement looks different for everyone, and so does the path to getting there. Some need to finish their role at an on-site location before making any moves. In contrast, others may have the flexibility to relocate before retirement and finish their careers from their next destination.
For those already visiting Orlando multiple times a year for Walt Disney World or other attractions, buying a home before retirement can offer another path. The property may begin as a vacation home base, become a snowbirding or seasonal residence, and then ultimately transition to a full-time home after retirement.
The good news is, there is no wrong answer when it comes to the best plan for the individual and family dynamic.
Where to Live in Southwest Orlando for Retirement
Once the timeline starts to take shape, it's natural to start thinking about where to live. Narrowing down Orlando communities is a great next step. Let's look at the SW Orlando communities retirees may consider when choosing their next move.
Windermere
Located just north of Walt Disney World, Windermere offers many of the lifestyle features retirees are seeking. Communities with on-site golf courses like Keene's Pointe and others with amenity centers like Belmere Village and Lakeside at Lakes of Windermere, homes with lake access on the Butler Chain of Lakes or one of the many private lakes, and small-town charm in the downtown, all make Windermere a great home base for that relaxed lifestyle with easy access to world-class attractions, shopping, dining, and services, including medical.
View communities and available homes in Windermere.
Dr. Phillips
In addition to proximity to some of the most concentrated dining and shopping at Restaurant Row, Universal, and Disney, the Dr. Phillips area offers many community options with access to world-class golf, including Bay Hill, Orange Tree, and Golden Oak. Dr. Phillips is also located near major roadways, including I-4 and SR-528, making access to downtown, medical facilities, and airports convenient.
View communities and available homes in Dr. Phillips.
Winter Garden
For those seeking newer construction communities alongside a nearby active downtown, Winter Garden has a variety of living options. Downtown, a well-known farmers market is held weekly, and plenty of dining and local shops are located off Plant Street. The West Orange Trail also runs right through town, so for those who like to get outdoors for a bike ride or daily walk, Winter Garden trail living makes it easy to take advantage of the 22 miles of trail.
Further south in Horizon West, the newer construction communities like Waterleigh, Hamlin Reserve, and Avalon Woods offer neighborhood connection to easy access to shopping and medical services at Winter Garden Village, Hamlin Town Center, and Flamingo Crossings. Access to Walt Disney World is also another top reason why retirees choose Winter Garden, with easy access via Western Way or Reams Road.
View communities and available homes in Winter Garden.
Clermont
Heading a bit further west is Clermont. Like Winter Garden, Clermont has seen significant growth over the last few years. With a mix of newer communities like Waterbrooke and established neighborhoods like Magnolia Pointe, Clermont offers a range of home styles and price points. Clermont's downtown has also seen a rebirth of dining and shopping, making it a cozy, yet vibrant space. Communities further south like Parkside Trails of US-27 are also benefiting from increased connectivity to Winter Garden with connector roadways currently in progress. Three road projects include the New Independence Parkway Extension connecting Orange County to Lake County at Wellness Way, SR-516, located a bit further south of Schofield Road, and the connector between Flemings Road to Sawgrass Bay to Western Way, and on to Disney.
View communities and available homes in Clermont.
55+ Communities Near Southwest Orlando
Central Florida offers a unique opportunity to live in dedicated 55+ neighborhoods. Ideal for those seeking an abundance of on-site resort-style amenities, like outdoor swimming pools, tennis and pickleball courts, fitness centers, and social events. These communities offer low-maintenance lifestyles with a variety of home styles. Some community HOA fees include lawn maintenance, high-speed internet, TV, gated entrances, and more.
55+ Community in Winter Garden
55+ Communities in Clermont & Minneola
- Kings Ridge
- Del Webb Lakehaven
- Heritage Hills
- Esplanade at Highland Ranch
- Summit Greens
- Del Webb Minneola
- Palms at Serenoa
55+ Community in Kissimmee
A Local Perspective on Retiring in Southwest Orlando
When choosing a location and home for retirement, especially when relocating from outside the area, it's important to work with a local expert who knows the area. They know the neighborhoods, but just as importantly, they know the right questions to ask to understand what matters most to each person. Jeffrey Funk has spent more than 25 years helping buyers and sellers navigate Southwest Orlando real estate. Along with his wife, Renee, they co-founded The Funk Collection and has called Windermere home for many years.
For those considering Central Florida for their retirement, it's often much more than finding a house with the right number of bedrooms. Windermere, Dr. Phillips, Winter Garden, Clermont, and the surrounding Disney area can offer very different day-to-day experiences, even when they appear relatively close on a map.
Understanding those differences can help narrow the search around the retirement lifestyle that matters most, whether that means getting out on the course daily, weekends on the lake, having easy access to travel, welcoming visiting family, choosing a lower-maintenance home, or staying close to everything that makes Southwest Orlando appealing. Schedule a call with Jeff to start a conversation about retiring in Orlando.
Frequently Asked Questions About Retiring in Orlando
Is Southwest Orlando a good place to retire?
Yes. Southwest Orlando offers warm weather, recreation, access to major attractions, airports, medical services, and a wide range of housing and community options. Windermere, Dr. Phillips, Winter Garden, Clermont, and the surrounding Disney area each offer a different lifestyle.
Is Florida tax-friendly for retirees?
Florida has no individual state income tax, which can be appealing to retirees relocating from states that tax income or retirement distributions. Property taxes and other housing expenses still vary by location and property.
Does someone need to live in a 55+ community to retire in Orlando?
No. In fact, many retirees choose traditional neighborhoods based on location, home style, golf or lake access, amenities, and proximity to attractions.
What are the benefits of living in a 55+ community?
Benefits vary by community, but many offer pools, fitness centers, pickleball and tennis courts, social activities, and lower-maintenance living. Some HOA fees may also include services such as lawn care, internet, or gated access.
Can a retirement home in Orlando start as a vacation or seasonal home?
Yes. Some future retirees purchase before leaving the workforce, use the home seasonally, and later transition it into a full-time residence.
Can a home near Disney be used as a short-term rental before retirement?
Some properties can, depending on local regulations and community rules. Always confirm short-term rental eligibility before purchasing. That's why working with local experts, like The Funk Collection, who understand the regulations is key.
Is Southwest Orlando convenient for frequent travelers?
Yes. Southwest Orlando offers access to Orlando International Airport, Sanford International Airport, Brightline service to South Florida, and Port Canaveral for cruise travel.
Is Orlando a good place to retire if family will visit often?
Definitely. Walt Disney World, Universal Orlando, SeaWorld, golf, resorts, dining, and other attractions give visiting family plenty to do while spending time together.
What type of home should someone look for when planning for retirement?
Look for a home that supports the expected lifestyle. Priorities may include single-story living or a primary bedroom on the main level, lower maintenance, guest space, community amenities, and golf or lake access.
Posted by Jen Durben on
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