13 Pros and Cons of Living in Winter Haven, FL

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Winter Haven, Florida, AKA Chain of Lakes City, is eight square miles of lakes connected by canals.

With 70,000 permanent residents split between the city limits and the surrounding area, Winter Haven has a small-town, family-friendly ethos.

Consequently, Winter Haven’s ample opportunities to enjoy the outdoors attract families from everywhere.

Pros of Living in Winter Haven, FL

1. The Chain of Lakes

Eight of the 50 lakes within the city limits or surrounding borders lie north of town, while another 16 run south to southwest, connected by canals.

The Natural Resources Division of Public Works oversees all 50 lakes, monitoring water quality and quantity.

Fortunately, Silver Lake, Lake Cannon, Haines, Hamilton, and Hartridge each have one public restroom, while Lake Shipp has two: one near Chain of Lakes Park and one near the northern end of Lake Shipp Park.

Unfortunately, however, Lakes Hamilton and Haines do not have public boat launch ramps.

Nevertheless, twenty-eight other lakes have public boat launch ramps, so you should not have problems getting your boat into the water.

2. Recreation

The City of Winter Haven Parks, Recreation & Culture Division, Office of Special Events issues parade permits for processions, races, walks, bicycle rides, and other parade-like events.

Consequently, suppose you wish to hold a large family reunion, carnival, festival, tournament, dance, concert, or block party in any city park. 

If so, you must apply for a special event permit a year before your event.

Inflatables may not be water-based and require the event organizer to provide the City Special Coordinator with a copy of insurance listing the city as a certificate holder.

Teen dance parties or any event which will serve alcohol, however, must hire WHPD police officers at the expense of the event holder.

In addition, events serving alcohol must get advance permission from the City Commissioners.

3. Night Live: Manor Professional Wrestling Dinner Theater

Winter Haven’s rich nightlife includes Manor Professional Wrestling Dinner Theater.

Seven bouts occur during the two-hour dinner, where the winners compete for the coveted Manor Medallion.

Dinner features chicken, mashed potatoes, and Manor cheesecake.

Although not currently open, their Manor Facebook group remains active, and you will find wrestler Panther B. Rolex there, so join the group to learn when the next bouts will take place!

4. Nightlife: Jessie’s Lounge and Jensen’s Corner Bar

Open Tuesday through Saturday from 4:00 PM to 2:00 AM, Jessie’s Lounge features live, original musical performances, including Jim and Judy’s Big Ass Jam on Wednesdays at 7:00 PM, where anyone can get up on stage to play and sing along.

Jessie’s also features Peace Train Karaoke every Thursday at 9:00 PM and an annual Super Bowl party.

Join Jessie’s Lounge Facebook group to keep up with events. 

Sister establishment, the non-smoking, pet-friendly Jensen’s Corner Bar, lies three doors down, connected to Jessie’s Lounge by a walkway and outdoor patio.

5. Nightlife: Barrel 239

Barrel 239 is the first and only whiskey bar in Winter Haven.

You can play Texas Hold’em every Tuesday at 7:00 PM and get 10 percent off drinks at the poker table.

Come early for bonus poker chips: 500 extra for arriving a half-hour early, and 1000 free poker chips for arriving at 6:00 PM.

Barrel 239 opens at noon Monday through Sunday and closes at 2:00 AM every day except Sunday when we close at midnight.

Join us on Thursdays for Trivia Night with Triviosity Live or Fridays for Karaoke Out Back, subject to weather.

Check Facebook for information.

The owners answer questions quickly and graciously.

6. Nightlife: Gram Parsons’ Derry Down

Byrds front man Ingram “Gram” Parsons, born in Winter Haven on Guy Fawkes Day, never abandoned his roots.

He called his country, blues, folk rock style Cosmic American Music, and Rolling Stone Magazine named him number 87 in their 100 Greatest Artists of All Time.

In addition, the State of Florida designated the Derry Down as a historical site on Gram’s birthday in 2015.

During your visit or while purchasing show tickets, you can also buy Derry Down merchandise, which includes a Gram Parsons Cosmic Revival T-shirt, a gift card, or commemorative bricks at the entrance. 

Join us on the first Monday of each month from 6:00 PM to 9:00 PM for open mic night.

Sign up to perform three songs in a welcoming, encouraging place for no charge.

7. Nightlife: Cypress Lanes

Open Monday through Thursday from 9:00 AM to 12:00 AM, Friday until 12:30 AM, Saturday until 1:30 AM, and Sunday until 10:00 PM, Cypress Lanes offers 40 bowling lanes, a two-story laser tag arena, and more than 70 classic and VR arcade games.

If you have a large group[, the owners advise making a reservation 24 hours in advance with their Activities Office.

Reservations require a deposit, and you must make a two-hour, two-lane minimum.

Call (863) 294-3295 to check availability before you leave home. 

Do you need somewhere to stay cool in the summer heat and keep the kids entertained?

Try a bowling day camp or field trip.

At $6 per child for one hour or $10 for two hours, including shoes and bowling balls, it’s the cheapest day camp around.

In addition, you can toggle “add extras” when you reserve your child’s spot to add a $4 lunch, including pizza or a hot dog and a 12-ounce soda, along with a 15-minute laser tag session for another $4.

Consequently, even if you shell out for the $14 package deal, it is a genuine bargain.

8. Lego Land

Pictures 150 acres with over 50 Lego-themed rides!

Every day between 10:00 AM and 7:00 PM, you can enjoy the Lego Land Brickworks, splash in the Water Park, or explore the new Peppa Pig Park.

Come for a single day, a weekend, or longer, or better yet, buy a seasonal pass and visit as often as you wish. 

9. S&S Micro Farm

If you would like a relaxing stroll through a 13-acre working mini farm, call 407-719-2403 or make an appointment online before you head downtown.

You will find the farm near the southwest end of Lake Elbert.

If you intend to go boating before or after your visit, Lake Elbert’s public launch ramp lies across the street from Polk Community College.

Cons of Living in Winter Haven, FL

Finding negatives about Winter Haven, Florida, poses a real challenge.

With so much to see and do, exhaustion should possibly have a spot on this list.

Nevertheless, there are a few downsides to Winter Haven Life (TM).

1. You Are Not Here Yet

Winter Haven brings YOLO and FOMO to a whole new level.

If you come for a visit, make it two weekends, bookending an entire week.

Lego Land requires at least three days to see everything in the park, and all the other activities in Winter Haven require a half-day to a full day each.

Many attractions offer parking for oversized vehicles such as travel trailers and motor homes.

Most must-see parks accommodate parents with children in strollers and people who use mobility devices.

If you intend to move here, the current three percent unemployment rate will allow you to find a new job in no time.

2. Public Transportation

The purple line of the Citrus Connection provides public bus service between Lakeland, Florida, and Winter Haven and takes a little over an hour from terminal to terminal.

Once in Winter Haven, eight fixed-route bus lines serve the area, including one specifically for Lego Land.

In addition, Citrus Connection offers riders the convenience of their mobile ticketing app, where single-ride, all-day, and monthly passes will display on your smartphone, eliminating the need to worry about buying and losing tokens.

Fares in Winter Haven rival other cities, charging just $1.50 for a one-way adult fare, $3 to ride all day, $12 for unlimited rides all week, or $47 for a monthly unlimited-ride pass.

Seniors pay half-fares, and ADA fixed-route riders pay nothing.

In addition, paratransit rides from door to door cost just $2 each way. 

3. Property Taxes

Like nearly every city, people love to complain about taxes.

Winter Haven’s property tax rate of $8.09 per $1,000 in home value might seem high to some, but it compares favorably to the rest of the United States, where it currently runs $11.36 per $1,000.

4. Crime

In February 2022, the Winter Haven Police Department had 100 fewer calls for service than it received in 2021. 

Moreover, burglaries, criminal mischief, robberies, and petty thefts saw the most significant drops.

The city had 187 violent crimes in 2019, only three homicides and 22 rapes. 

However, aggravated assaults accounted for 137 crime reports.

Overall, since Winter Haven experiences more crime than the rest of the country, allow your gut instincts to lead. 

For example, retain awareness of your surroundings at night.

During the day, exercise precautions such as locking purses and valuables in the trunk or taking them with you instead of leaving them in plain sight in your vehicle.

Carry as little money as possible, and use payment apps instead of cash or credit cards whenever available. 

Pros and Cons of Living in Winter Haven, FL – Summary Table

Florida Safety Overview

READ THE FULL REPORT: Florida Safety Review

Safety Index:

70

• OVERALL RISK: MEDIUM
• TRANSPORT & TAXIS RISK: MEDIUM
• PICKPOCKETS RISK: MEDIUM
• NATURAL DISASTERS RISK: MEDIUM
• MUGGING RISK: MEDIUM
• TERRORISM RISK: HIGH
• SCAMS RISK: MEDIUM
• WOMEN TRAVELERS RISK: LOW