Retiring to Winter Haven: Pros, Cons & Costs in 2024

Retiring to Winter Haven: Pros, Cons & Costs in 2024

Having year-round access to the world’s best freshwater fishing or learning yoga on the tranquil waters of a lake may sound like the stuff of retirement fantasies. But scores of Americans retiring in their mid-40’s and 50’s to Winter Haven, Florida have turned this fantasy into reality.

Google Search Interest in Retirement Related Queries data. Winter Haven, FL vs Other US Cities.

Perhaps unsurprisingly, Spyfu SEO data reveal that each year, Americans run over 3,300 searches on retiring to Winter Haven, FL, also known as the ‘Chain of Lakes City’ (see figure above). Even more remarkably, the most recent IRS stats show that over 24,800 taxpayers moved to Polk County, seat of Winter Haven, from other US states within a single tax year (figure below).

Given that 3x as many people moved to Polk County as the number who moved away to other states (a little over 7,750), the writing on the wall is clear: Winter Haven, FL is clearly an attractive relocation destination for Americans.

IRS Migration Inflow data Winter Haven

But does that hold true for people considering retirement? Can retirees have a rewarding, yet affordable lifestyle in a place like Winter Haven, FL?

At PlayLouder, we know that to uncover the full picture, you’ve got to dive right in. So we dove. We looked at everything from fuel bills to fly fishing for a complete tear-down of what it is that makes Winter Haven, FL a great place to retire to.   

While we were at it, we put together a summary of handy facts, a kind of ready reckoner for anyone seriously looking to relocate to Winter Haven, FL in 2024. So here it is.

Main Pros and Cons of Winter Haven, FL for Retirees

Sometimes it’s helpful to get a bite-sized summary to digest quickly, before digging into the meal-sized report. That’s why we’ve put together just such a summary for you. 


If your retirement vision encompasses a healthy, outdoors lifestyle where fun and variety are nicely balanced against financial vigilance, Winter Haven, FL has got to be one of your top choices. The combination of natural beauty, cultural vibrancy and a safe and peaceful lifestyle are made irresistible by the affordability of everything from property rents to quality healthcare.  


On the other hand, if having access to unlimited culinary, shopping and nightlife options ranks high on your list of priorities, relocating to Winter Haven may throw up challenges. An added constraint is the lack of direct air connectivity, which might be a drawback if your work or lifestyle necessitates frequent flying.

Cost of Living


Winter Haven, FL possesses many charms, but the low cost of living in the area is arguably an attraction as strong as any of the others. Here is a walk-through of what life in Winter Haven costs in 2024. 

Housing and Utilities

According to the nationwide listing service, rents in Winter Haven, FL have gone down by 1.3% during the 2023-2024 period. However, local real estate listings reveal a 5% to 6% increase in apartment rents in the area.

When compared to the US average, however, Winter Haven rents continue to be substantially lower. According to recent Numbeo data, rents on one-bedroom apartments, whether within the city or on the outskirts, are significantly cheaper than their counterparts in other US cities. 

Rent savings on larger apartments are even steeper, particularly within city limits (figure below).

That’s not all…

Real Estate Cost of Living Winter Haven

As per Numbeo stats, buying a house in Winter Haven, FL today represents big savings (anywhere from 26% to 38%) when compared against nationwide averages. However, do these data hold up to local facts? I decided to find out, so I sourced data from a number of local realtors. 

What I found was that the average sale price of a house in Winter Haven, FL in 2024 comes out to a little over $302,000. (Keep in mind that expert assessments during 2023-2024 peg the median price of a house in the US at anywhere between $426,000 and $492,000.)

A buyer can thus expect to save over $100K on a house, if the property is in or around the Winter Haven area! 

Utilities Cost of Living Winter Haven

Winter Haven is on par with the rest of the US with respect to utility bills (heating/ cooling, waste disposal). On the other hand, both internet and cell-phone bills represent significant savings of over 20% (figure above).

Food, Grocery and Apparel

Food Cost of Living Winter Haven

Barring milk and oranges, I could find hardly any essentials that did not carry lower price tags in Winter Haven compared to the respective country averages. The weekly $$ savings are likely to add up to a tidy sum in the course of a year (figure above).

Eating out in this city also works out cheaper than average, whether you’re grabbing a bite at the corner café or pulling out all the stops at an upscale restaurant. 

Likewise, restocking your wardrobe is likely to be cheaper in Winter Haven, FL compared to the US average, and significantly lower than metro city prices, with the only exceptions being items such as women’s summer wear (figure below). 

Clothing Cost of Living Winter Haven

Transportation and Fuel

Winter Haven’s exceptional public transit system, called Citrus Connection, operates not one or two, but three distinct sets of regional transit services in the Lakeland-Winter Haven area. 

Buses under the Citrus Connection fleet label and the Winter Haven Area Transit (WHAT) label run along 8 routes that serve multiple towns and suburbs in the area, including Auburndale, Bartow, Dundee, Fort Meade, Frostproof, Haines City, Lake Alfred, Lakeland, Lake Wales and Winter Haven. 

In addition, the city’s paratransit system operates ADA-compliant vehicles that provide door drop and pickup for eligible passengers on request. 

A range of fares is available, from regular, one-way tickets ($1.50) to discounted fares for students, seniors and differently-abled passengers, besides unlimited daily, weekly and monthly passes. Children and ADA-eligible passengers ride free.        

Fuel, Transportation and Automobiles Cost of Living Winter Haven

Driving is also an economical option in this city, particularly for those with more complex commutes, since gas prices are nearly 10% lower than average. For those looking to buy, a mid-sized, entry level sedan could well net you nearly 12% in savings here when compared to other cities.

Local Economy and Part-Time Job Opportunities

US Census Bureau analysts named Winter Haven-Lakeland among the top five fastest-growing metro areas in the country for two consecutive years, ranking it #3 in 2022 and #2 in 2023. Data from FRED (the St. Louis Federal Reserve) show that in the last five years (2018 to 2022), Winter Haven’s GDP has grown by an average 7.6%.

Employment Growth Rate in Winter Haven

In sync with this trend, the city’s Chamber of Commerce pegs economic growth at a healthy 1.3% over the coming year. Keeping pace with this trend, US Bureau of Labor Statistics (US-BLS) data forecast a 2.5% growth in Winter Haven job opportunities through 2024-2025 (figure above).

US-BLS data additionally reveal that the major drivers of job growth in the area are the education and healthcare sectors, followed by government service (figure below).   

Economic Growth Rate in Winter Haven

Local sources confirm these growth trends, saying that plans to expand educational facilities like Polk State College will create more job opportunities. Similarly, a new manufacturing facility for 84 Lumber, one of the nation’s biggest building materials suppliers, is creating over 80 jobs in the area. 

Other infrastructure projects currently underway that are creating new jobs and expected to continue doing so include:

  • Affordable housing development project – $  23 million
  • Lake Elbert trail construction – $    9.6 million
  • Winter Haven roadworks – $    3.3 million

Job Prospects for Retirees

In a survey by Columbia University’s School of Public Health, the majority of business owners expressed a preference for hiring older adults. The most commonly cited reasons were:

  • Experience in coping with job challenges
  • More reliable and consistent in performance
  • Ease in mentoring younger, junior team members
  • Good at building rapport with customers 

For those considering retiring to Winter Haven, FL, its combination of robust economic growth, great public transit system and expanding senior community are major factors tilting the scale in favor of finding the ideal post-retirement employment. The figure below offers a bird’s eye view of remuneration across job sectors in the Winter Haven area over the last 9 months.

Weekly Wages by Sector in Winter Haven

Healthcare Facilities, Costs, and Quality

Winter Haven, FL is currently served by two major hospitals, the Winter Haven Hospital (part of the Baycare Health System) and AdventHealth Heart of Florida.

The 468-bed Winter Haven Hospital provides a spectrum of care, with over two dozen departments ranging from dermatology and ear, nose and throat health (ENT) to immunology, neurology and pulmonology or respiratory health. Hospital facilities also include advanced imaging and surgical specialties, as well as cancer care and psychiatric care.

AdventHealth addresses a host of major and minor health concerns. Their main center in Winter Haven houses multiple departments dedicated to cardiology, orthopedics, stroke care as well as obstetrics and gynecology. In addition, they have an urgent care center (CentraCare) and an upcoming emergency care or ER center. 

Besides these, Winter Haven has a full-fledged, 61-bed women’s hospital (also affiliated to the Baycare Health System) that provides comprehensive care across the lifespan for the women of Polk County.

The city boasts over 750 healthcare practitioners specialized in diverse fields, from family and internal medicine to neurology and psychiatry, ensuring that all your healthcare needs are amply met in Winter Haven, FL. Healthcare for your beloved pets is also assured, with over 90 veterinarians actively practicing in and around the city.

Average Healthcare Cost in Winter Haven

A quick survey showed me that on the whole, healthcare costs are also lower in Winter Haven compared to country averages. You can expect to pay less on doctor and dentist visits (see figure above), as well as on eye-care. On the other hand, veterinarian visits are likely to cost a fair bit extra (35%). 

Healthcare and assisted living for seniors

A plethora of facilities has grown in Winter Haven, FL to keep pace with the growing community of older adults and seniors in the area. These range from retirement communities with independent living for active older adults to full-time assisted living for seniors requiring nursing and memory care.

Well-reputed facilities that cater to the entire range of senior care needs, from independent lifestyles with minimal support to full-on assisted living include the Spring Haven Retirement Community and Lake Howard Heights. 

Top-rated institutions that offer both short-term care (such as rehab, post-op care) as well as longer-term assisted living services include Hawthorne Inn and Wedgewood of Winter Haven. Trusted facilities that specialize in assisted living include Brookdale Winter Haven and The Gardens of Lake Alfred.   

Safety and Accessibility

Crime and safety

From a quick comparison of the FBI’s crime rate statistics (see figure below), it was evident that Winter Haven’s stats are much lower than the country average for violent crimes as well as property crimes. 

However, we decided to get some insider perspective. How safe does the city actually feel? So we sought out the opinions and experiences of locals – both current and former residents.

Crime Rate Per 100k Individual in Winter Haven

Here’s a summary of what over a dozen different people, both residents and visitors to the city, had to say about Winter Haven, FL: 

Without an exception, everyone reported feeling very safe in the city, with a couple of people adding that they’d moved around the city safely at night, too. Only one person was able to share with us a ‘brush with crime’ experience—a drive-through store robbery that occurred in the street behind her house. 

As one individual picturesquely phrased it, “if you enjoy living life in the fast lane, you’re more likely to be a victim of boredom than of crime in Winter Haven”. 

Safest neighborhoods

Given the overall high safety ratings people provided for the city, we decided to question them on places to be avoided. Many responded by saying that they didn’t know of any really unsafe neighborhoods in Winter Haven. However, a few people suggested that the Inwood and Jan Phyl Village areas might be poor choices for living in.

Accessibility: Getting to Winter Haven, FL

By road

Google Map getting to Winter Haven
  • Orlando, FL: Lying roughly 46 miles southwest, Winter Haven is a 50-minute drive away. Begin by heading west on I-4 West for 40 miles. Take exit 41, merge onto FL-570 East and keep on for about 20 miles. Take exit 14 onto FL-540 West/County Line Road and drive for approximately 9 miles. Turn right onto US-17 North/South Florida Avenue and continue for roughly 2 miles to reach Winter Haven.
  • Tampa, FL: The hour-long drive from Tampa to Winter Haven is just short of 50 miles. Start out by taking I-4 East for about 45 miles. Then take exit 27 and follow FL-570 East for approximately 18 miles. Next, take exit 14, get onto FL-540 West/County Line Road and continue for about 9 miles. Turn right onto US-17 North/South Florida Avenue and drive the last 2 miles to Winter Haven.
  • Miami, FL: At approximately 226 miles northwest, the drive from Miami to Winter Haven typically takes around 3 hours and 40 minutes. Set out along I-95 North for about 150 miles, then merge onto I-4 West toward Orlando. In about 180 miles, take exit 41. Merge onto FL-570 East and drive for about 20 miles. Take exit 14 to get onto FL-540 West/County Line Road and follow it for roughly 9 miles. Turn right onto US-17 North/South Florida Avenue for 2 miles till you hit Winter Haven.
  • Fort Myers, FL: It’s a round 108-mile drive from Fort Myers to Winter Haven that takes a little over 2 hours. Begin by driving north on I-75 North. In about 90 miles, take exit 261. Turn right onto FL-582 East and continue for roughly 10 miles. Turn left and keep on US-98 North for approximately 30 miles. Turn left onto FL-540 East/Winter Lake Road and drive for about 6 miles. Turn left onto US-17 North/South Florida Avenue for the last 2 miles to Winter Haven.
  • Jacksonville, FL: Winter Haven is 186 miles to the southwest of Jacksonville, a journey of about 3 hours. Start by driving south on I-95 South. After about 120 miles, merge onto I-4 West toward Orlando and keep on for about 150 miles. Take exit 41, merge onto FL-570 East and drive for about 20 miles. Take exit 14 to get onto FL-540 West/County Line Road, and drive for about 9 miles. Turn right onto 

Both Greyhound and FlixBus operate services to Winter Haven, FL, making it a viable alternative to driving. Starting points include all nearby cities (such as Tampa, Orlando, Miami and Jacksonville) as well as major cities further away (New York, Washington, Richmond, Nashville, Atlanta, Houston, Phoenix, Denver and so on). 

By rail

Winter Haven, FL is not directly on the train route. However, sister city Lakeland is served by AMTRAK, with a daily train running from Jacksonville. Travelers can then take the AMTRAK shuttle from Lakeland to Winter Haven, with a total travel time of roughly five and a half hours.      

By air

The nearest airport to Winter Haven is Orlando international airport (MCO), at a distance of 48 miles. Another option is Tampa international airport (TPA), at 57 miles. Both these airports are served by all major US carriers (American, Delta, Southwest, United) as well as a host of international airlines including Air Canada, British Airways, Caribbean Airlines and Virgin Atlantic.


Tucked away in the heart of Central Florida, Winter Haven boasts a humid subtropical climate all year round. 

The sun-drenched summers are perfect for waterside activities, whether vigorous pursuits like water-skiing and paddleboarding, a gentle boat ride or even just lazing on a deck. Autumn's moderate temperatures encourage leisurely afternoon walks around the scenic Chain of Lakes and evening outings in the charming downtown area. 

Winter Haven enjoys mild winters, just crisp enough to invigorate outdoor activities without the need for heavy bundling. Lush greenery and gentle sunshine set the stage in spring for golfing, fishing and paying a visit to the famed Cypress Gardens (now part of the Legoland Florida Resort).

Annual Temperature Range in Winter Haven

Weather and water preparedness

Winter Haven falls within the broad swath of Florida's hurricane zone. During the rainy months from June to November, it is advisable to stay updated on local weather forecasts, and to adhere to safety advisories. 

Foremost among hurricane precautions is securing loose objects (for example, trash cans or patio furniture) that could turn into dangerous projectiles in high wind. Having an emergency kit handy that includes essential supplies is also a good idea—drinking water, non-perishable food, essential medications and a first aid kit as well as a flashlight and batteries.

While exploring the lakes and waterways of the Winter Haven area, prudence likewise dictates being on the lookout for alligators and snakes, which are native to the area. Additionally, avoiding swimming in non-designated areas and keeping a close watch on children near and in water are good precautions.

Environment quality

Among its many attractions, the Winter Haven-Lakeland area provides lungfuls of fresh, clean air. Some evaluators rank Winter Haven, FL among the top 5 US cities in environmental quality, as its residents are assured of approximately 315 days a year with AQIs averaging lower than 40. Naturally, the particulate matter count for the city stays well below the EPA's annual cutoff of 12 μg/m³ throughout the year (figures below).

Air Quality Index in Winter Haven
Particulate Matter Index in Winter Haven

Mid-Florida has year-round mild weather, and the warm winters are especially conducive to triggering spring-time allergies. In Winter Haven, the trees that put out the most pollen in spring include different varieties of oaks, ash, cedar and hickory (pecan). 

Summer and fall allergies in this region are largely owing to grasses such as Timothy, Johnson and Bermuda, as well as redtop, bluegrass and sweet vernal. Weeds such as lambsquarters, Russian thistle, ragweed and pigweed are also often culprits, especially during the fall.  

For those prone to allergic reactions, still days with no breeze and strong sunshine can be a sign to limit time spent outdoors. The ozone clouds that form in such weather can contribute by worsening allergy symptoms.

Education and Learning

Winter Haven, FL has an educational landscape that presents a wide range of learning avenues for people of all ages. Whether it's young students embarking on their educational path in kindergarten or senior citizens pursuing personal growth, Winter Haven's educational institutions are geared to meet the diverse learning requirements of its residents throughout their lives.

Traditional Academics

Polk State College (PSC) is the major institution for higher education whose campus is right within the city. PSC offers two-year associate degree programs in its ‘lower division’ (in-state tuition in 2024: $112.22/ credit hour or as well as four-year bachelor’s degrees in its ‘upper division’ ($123.89/ 

Lakeland, FL, sister city to Winter Haven, is home to numerous colleges and universities, including Florida Southern College (FSC), Florida Polytechnic University (FPU), Keiser University and the Lakeland campus of the University of South Florida (USF). These institutions vastly expand the opportunities available to residents.

FSC offers a full complement of undergraduate and graduate courses, including master’s and doctoral programs. In 2024, full-time undergraduate tuition is $44,040, while graduate tuition ranges from $475 to $850/

Apart from undergraduate programs, Keiser University’s unique College of Golf boasts programs designed for careers in the golfing industry, ranging from turf management to teaching professional golf. Florida Polytechnic offers STEM-oriented programs in a host of disciplines, from applied mathematics to cybersecurity engineering.

Continued Learning

In addition to full-time students, Polk State offers continuing education courses for older adults aiming to broaden their workplace skill-set or to deepen their knowledge. The host of subjects on offer ranges from civic leadership to emergency medical services (EMS) to advanced manufacturing. Course fees range from as little as $150 to $1,900.

Florida Southern College has a special stream of bachelor’s programs designed for adults wishing to pursue study later in life. Tuition for adult bachelor’s programs in 2024 is $340/ 

USF-OLLI (Osher Lifelong Learning Institute) has over 200 courses for older adults and seniors wishing to stay engaged and to enrich their lives and skills. Courses range from card games such as canasta to investment skills and real estate fraud detection, health and fitness (yoga, Alzheimer’s care) as well as technology skills such as using generative AI.  

USF-OLLI courses require signing up for a membership (at an annual registration fee of $50). Course fees range from as little as $20 to $65, while several single-session lectures and courses are offered free. 

School Education

The Winter Haven area has a total of 35 schools listed by NCES, including 21 public and 14 private schools. At least 10 public schools have pre-KG, kindergarten and elementary grades, 9 schools include middle grades, while 6 cater to high school students. 

Some of the most highly rated schools in the area include Hartridge Academy and Frank E. Brigham Academy (both cater to grades K‒5), Jewett Middle Academy (6‒8), as well as Winter Haven Senior High (6‒12) and Chain Of Lakes Collegiate High School (11‒12). 

Demographics and Social Profile

Demographic Profile in Winter Haven

Winter Haven, FL is home to approximately 55,020 individuals, per the 2022 census. Of them, roughly 15,400 (28%) fall in the below 18 age-group, while senior citizens – age 65 and above – make up another 23% (roughly 12,650 in number). Clearly, the age demographic of this city is spread out pretty evenly.

Likewise, the male‐female ratio is well-balanced in Winter Haven, at approximately 48% : 52%. In terms of ethnicity, Caucasians/ Whites make up a slight majority (53%), while African-Americans constitute nearly 27%. Individuals of Hispanic descent make up another 21%. Asians make up less than 2.5%, while those of Native American or Alaskan origin constitute less than 1%.

A significant 9% (approximately 4,950) of Winter Haven residents are foreign-born. Foremost among them are individuals of Cubans (roughly 4%), Haitians (about 1.5%) and Colombians (a little over 1%).

In every presidential election since 2000, the city of Winter Haven has returned a Republican majority. The vote split in the 2020 presidential election was approximately 57% Republican vs. 42% Democrat (with roughly 1% of votes going to the independent candidate). The Polk County area leans conservative, with the city itself being generally viewed as being only somewhat conservative.

Founder at Play Louder !

Joe DiSanto is the founder of Play Louder! He has built multi-million dollar businesses, produced critically acclaimed documentaries and an Emmy-winning TV show, invested millions in real estate, and semi-retired at age 43. Now, Joe serves as a Fractional CFO for several creative firms and is sharing a lifetime of fiscal know-how via Play Louder, an invaluable resource that helps individuals and business owners increase their net worth and plan better for their future.