16 Essential Pros and Cons of Living in Winter Haven, Florida
Tampa BayFlorida

Is Winter Haven a good place to live? If you enjoy a laid-back community that offers residents a low cost of living, great neighborhoods, and plenty of ways to enjoy themselves in the outdoors, then yes, it’s a wonderful place to live. Once known as the “World’s Winter Haven,” people once flocked here to escape cold winters. Now, it’s a premium spot to live between the major Florida metros of Orlando and Tampa, but there are a few things you need to know before you pack your bags. Here’s our list of the biggest pros and cons of living in Winter Haven, Florida.
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Winter Haven at a Glance
- Population: Winter Haven’s population is about 52,800.
- Median age: The median age in Winter Haven is 40.6. However, according to U.S. Census data, roughly 20 percent of the population is over 65, and over 21 percent is under 18, making it a great place to live for families and retirees alike.
- City size: Winter Haven’s total area is about 40 square miles.
- Location: The city is located in Central Florida and sits halfway between Tampa and Orlando.
- Fun fact: Winter Haven is considered the “Water Ski Capital of the World” thanks to its 50+ lakes.
16 Pros and Cons of Living in Winter Haven, Florida
If you want to know more about whether Winter Haven is a good place to live, we’ve compiled a list of 16 important pros and cons to know before you make the move.
1. Pro: Winter Haven, FL Is Centrally Located
So, where is Winter Haven, Florida, located? The city is in Polk County, which is in central Florida. One of the many benefits of living in Winter Haven, FL, is that you’re roughly halfway between two major cities in Florida, Tampa and Orlando. This means you can visit all the fun of Walt Disney World and Universal Studios in just over an hour. Or, head west toward the beaches and Busch Gardens in Tampa.
Winter Haven is the home of Legoland Florida, so you don’t have to travel out of the city to enjoy roller coasters, water parks, and even a botanical garden. The larger city of Lakeland is not far from Winter Haven as well and features a thriving arts and cultural scene.
2. Con: The Weather in Winter Haven May Take Some Getting Used To
While people still flock to Winter Haven during the cold northern winters, if you’re not originally from Central Florida, the summer weather may take some getting used to. Moving from a different climate isn’t all that bad if you’re moving in November, but Winter Haven is hot and humid outside those mild months. The summer season peaks in July, with temperatures that consistently reach the 90s. You can expect almost daily rainstorms from June to August, plus lots of muggy weather.
There’s also hurricane season to take into account. Central Florida cities like Winter Haven might be a little safer from hurricane damage than coastal cities, but there is a flood and heavy rain risk to be aware of. Plus high winds and the rare tornado that pops up during a hurricane.

Living in Winter Haven, FL, means enjoying lakefront dining and beautiful sunsets — without the higher cost of living found in nearby cities like Tampa and Orlando.
(Source: Visit Central Florida via Facebook)
3. Pro: The Cost of Living in Winter Haven, Florida, Is Low
One of the major pros of living in Winter Haven is the lower cost of living, especially compared to other Florida cities. The cost of living in Winter Haven, Florida, is 91.6, which is lower than the national index of 100 and the state average of 103.1. By choosing to live in a city like Winter Haven, you’ll avoid the higher costs of living in Tampa, with its score of 104.2, as well as in Orlando, with its score of 106.
This means that if you need a salary of at least $50,000 in Tampa or $52,000 in Orlando, you’d only need to make $46,000 in Winter Haven as a single adult.
4. Con: Tourist Season in Winter Haven Can Be Tough
Tourists escape to cities like Winter Haven for a reason — to avoid the cold winters! That means as a resident, you’re going to share the mild winters with snowbirds. This can lead to congestion on the roads, increased competition for parking spaces, and more people in general enjoying all the community has to offer. You’ll notice an increase in people out on the many lakes, at restaurants, enjoying parks, and out on the golf courses.
5. Pro: Retirees Especially Love Living in Winter Haven, FL
If retiring in Florida is on your radar, Winter Haven’s community is a strong point in the “pro” list. Retirees really love living in Winter Haven, but you’ll also find a lot of families here thanks to the strong community ties and great neighborhoods. Retiring in Winter Haven is the dream for a lot of seniors, thanks to its lower cost of living, mild winters, HOA-focused communities, and great golf courses, like the Cypresswood Golf and Country Club. Winter Haven has a more relaxed pace of life than other Florida cities, offers lots of opportunities to stay active, and has stellar healthcare facilities like Winter Haven Hospital.
6. Con: There Is Limited Public Transportation in Winter Haven, FL
Most residents of Winter Haven have a car, as the public transportation is limited. The city operates as part of the Citrus Connection, which gives riders access to areas across Polk County. However, most people use it to connect to Lakeland and not as a way to get around Winter Haven. It is worth noting that downtown Winter Haven is very accessible, with a walk score of 77 out of 100.
7. Pro: Winter Haven’s Dining Scene Is Growing
Although it’s a smaller-sized city, the food and dining scene has been growing lately in Winter Haven. A lot of this has to do with the revitalization of downtown, which allows pedestrians to easily walk to a variety of restaurants and bars to enjoy delicious food and drink with a view of one of the many lakes. Grab American favorites at Lucille’s American Cafe, or enjoy Louisiana BBQ at Smokin’ OX. Grab a beer at Grove Roots Brewing Co., Winter Haven’s first craft brewery, and stay for the live music, trivia nights, food trucks, and vendor market.
8. Con: Winter Haven Doesn’t Score High When It Comes to Safety
Is Winter Haven, FL, safe? Winter Haven doesn’t have the highest safety rating according to NeighborhoodScout. Its total crime index is 20, making it safer than only 20 percent of U.S. cities. Your chance of being a victim of either violent or property crime is 1 in 57, making Winter Haven’s crime rate higher than 73 percent of other Florida cities. There are safe neighborhoods in Winter Haven, though, including Lake Ashton, Gordonville, and Shadow Wood.

There are plenty of things to do in Winter Haven, Florida — like spending the day at the LEGOLand Florida Resort.
9. Pro: There Are Lots of Things To Do in Winter Haven, Florida
You’ll never be bored in this city, as there are all kinds of things to do in Winter Haven, FL, no matter what you’re up for! Here area few ideas:
- LEGOLand: This theme park has it all for both kids and adults. There are thrilling rides, live shows, a water park, an aquarium, and annual events like the LEGO Festival.
- Theatre Winter Haven: If it’s live performances you’re interested in, Theatre Winter Haven is the place to be. Whether you enjoy plays, musicals, karaoke, or lively bingo nights, there’s never a dull night in Winter Haven.
- Downtown Winter Haven: The downtown area is the hub of the community — plus, it’s very walkable. Admire the historic buildings, stop into coffee shops like Richard’s Fine Coffee, enjoy strolling through Central Park, or stop for burgers and seafood at Sauvage.
10. Con: There Are Limited Nightlife Options in Winter Haven
While the dining scene is growing, you’ll find nightlife options a little limited in Winter Haven. The demographics of the city (more retirees and families) skews the entertainment options to more family-focused or recreational. Residents prefer to enjoy the outdoors and get the most out of the city’s lakes, whether with boating, kayaking, or fishing. While there is a good selection of bars in downtown Winter Haven, you won’t find many clubs or late-night entertainment options.
11. Pro: Winter Haven Has Plenty of Great Neighborhoods
Out of the various pros and cons of living in Winter Haven, Florida, one of the major pros is its neighborhoods. If you’re ready to move to Winter Haven, consider finding a home in one of these top communities! The best Winter Haven neighborhoods include:
- Elbert Lake: Elbert Lake is a great community, especially for families, because it is a quiet, safe neighborhood that offers walkability. It’s conveniently located close to downtown Winter Haven, as well as Rotary Park. This spot is also popular for dog owners because of the well-maintained walking areas!
- Lake Ashton: Lots of retirees call Lake Ashton home because it is a safe, 55+ community that provides 24-hour gated access. Residents here love the two 18-hole golf courses, as well as the clubhouse, fitness center, and indoor pool.
- Chain of Lakes: If you’re a young professional with a growing family interested in moving to Winter Haven, you’ll want to check out the neighborhood of Chain of Lakes. Here you’ll have immediate access to multiple lakes perfect for boating and fishing, as well as convenient shopping and dining options at Chain O’Plaza.
12. Con: The Job Market in Winter Haven, FL, Is Limited
Keep in mind that moving to Winter Haven, FL, means you have limited opportunities when it comes to job industries. Major industries include agribusiness, transportation, healthcare, and tourism. This city is smaller in size, so it doesn’t offer jobs in as many fields as nearby Lakeland, Tampa, or Orlando — although commuting to those cities for work is always an option. The unemployment rate is also lower than the national average, at 4.5 percent.

Living in Lakeland, FL, gives outdoor enthusiasts access to endless opportunities for water sports and lakefront adventures.
(Source: City of Winter Haven, FL via Facebook)
13. Pro: Adventuring Outdoors Is Easy in Winter Haven, FL
When you’re considering the pros and cons of living in Florida, it’s always good to know if you’ll be able to enjoy the outdoors. Luckily, moving to Winter Haven means you’ll be among like-minded residents who really take advantage of their beautiful natural surroundings.
The interconnected freshwater lakes offer you the chance to get out on the water — sometimes in your own backyard! There are plenty of opportunities for boating, paddleboarding, kayaking, fishing, and swimming throughout the city, as well as lots of green spaces to relax in, like Central Park.
14. Con: Winter Haven Deals With Lots of Congestion & Traffic
Although it increases more during the winter, you’ll find that congestion and traffic are concerns throughout the year in Winter Haven. The city has been growing steadily year-over-year at a rate of 3.76 percent, meaning the city is becoming more crowded. Plus, the city’s layout isn’t great for reducing traffic, as roads must be routed around the many lakes.
15. Pro: Winter Haven Is a Tight-Knit Community
Winter Haven is a relaxed, welcoming community that takes pride in offering lots of ways for neighbors to connect. Whether it’s farmer’s markets, craft shows, youth athletics, summer camps, or senior yoga at the library, there’s a way to get involved for all ages in Winter Haven. The neighborhoods are walkable, and most residents enjoy being near the lakes, making it easy to meet up with friends or make new ones.
16. Con: Property Taxes in Winter Haven May Be Higher
Florida has no state income tax, which means as a resident of Winter Haven, you’ll get to keep more of your hard-earned income in your pocket. However, the property taxes you’ll need to pay may seem a little higher, especially if you’re moving to Florida from out of state. A lot of property taxes across the state, including in Winter Haven, seem to be rising for a variety of reasons that include an increase in population, higher home values, and more service costs.
Pros and Cons of Living in Winter Haven — FAQs
Q: What is the crime rate in Winter Haven, Florida?
A: Winter Haven’s total crime index is 20, according to NeighborhoodScout, meaning it is safer than 20 percent of U.S. cities.
Q: What should you know before moving to Florida?
A: Be ready for intense weather that can include high heat and destructive hurricanes. Lots of tourists lead to congestion year-round, but there are a variety of things to do, including great beaches and natural areas to explore in Florida.
Q: Which is better, Lakeland or Winter Haven?
A: Lakeland is larger with more amenities, while Winter Haven offers a slower pace of life and is more affordable.
Q: Is Winter Haven, FL, a nice place to live?
A: Yes, especially for families and retirees because it is laid back and the cost of living is low.
Q: What is Winter Haven known for?
A: The city is known for its chain of lakes, thanks to its 16 interconnected lakes.

After weighing the pros and cons of living in Winter Haven, Florida, make your move flexible with PODS.
Knowing the Pros & Cons of Living in Winter Haven, Florida, Why Not Move There With PODS?
Deciding to move to Winter Haven is the easy part. The challenge is getting there. PODS can make your move flexible with a portable storage container delivered right to your driveway. You can load it on your own or hire local packing and loading assistance if you need help with the heavy lifting. Once you’re ready to move, have your container picked up and delivered to your new Winter Haven home or to a secure PODS Storage Center until you’re ready to unload. One month of storage is included in the cost of every more, so you can take your time without feeling rushed.
Visit PODS online for a free local moving quote or call 877-350-7637 for long-distance moving.
Editor’s note: For ease of reading, monthly rental prices were rounded to the nearest $25 and home values were rounded to the nearest $100.
Source for image featured at top: City of Winter Haven, FL via Facebook
*This article was written on behalf of PODS Enterprises, LLC (“PODS”). PODS does not warrant the completeness or accuracy of any information contained in this article and disclaims any liability for reliance upon the content herein.

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