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Winter Haven, Florida Real Estate & FHA Homes for Sale -

Between two of Florida's largest cities, Orlando and Tampa, Winter Haven is home to plenty of appealing attractions, from beautiful lakes to the world's largest LEGOLAND and a world-class vintage aircraft collection. And that's not all; there are plenty of other places to reflect, explore, and play.

With a history in Americana rock & roll, lakes, and citrus, Winter Haven offers an experience of modern lifestyle possibilities. It's where you'll find family fun in every park, a concert in every corner, and arguably one of the few places where affordable lake living is accessible.

Why Move to Winter Haven, Florida?

Being a typical Florida town, there are numerous perks to living in Winter Haven, Florida.

Plenty of Attractions and Family-Friendly Activities

If you're looking to move to Winter Haven, Florida, be ready to discover this town's finest. Some of the city's renowned attractions include:

LEGOLAND Florida Resort

Winter Haven is no exception to Central Florida's theme park utopia. Home to the famed LEGOLAND Florida Resort, the town is one of the finest family-friendly spots in Florida.

The Legoland theme park offers over 55 attractions and rides that are entirely LEGO-inspired. A water park, interactive experiences, botanical gardens, and roller coasters are just a few attractions you can find here. And yes, you may even design your art pieces at the Build-Your-Art Gallery, which will later be displayed.

Aside from rides and attractions, the park is packed with LEGO figures with whom families may pose for photos. Characters such as Nya and Kai are frequently spotted exploring the park.

Plan your visit during one of the park's seasonal festivals to spice up the experience. Its signature event is the Brick-or-Treat Halloween festival, which features amusing entertainment, a special Monster Party, exclusive LEGO characters, and candy buckets.

Theatre Winter Haven

Theatre Winter Haven is the place to go in Central Florida for anyone looking for a night at the theater. The company at Theatre Winter Haven is renowned for throwing great musical performances and is regarded as one of the top community theaters in the country.

Established in the 1970s, Theatre Winter Haven presents a Tribute Tuesday Series, a Professional Series, a two-play Academy series, and a five-play MainStage season. Even more impressive, the company has launched a new Blackbox theater as a second performance space in 2022.

The MainStage shows have been a significant source of entertainment for Winter Haven residents and visitors for over 50 seasons. Some of its notable recent performances are Elf, The Musical, Hairspray, Little Shop of Horrors, and Grease.

Suppose you're planning a prolonged stay in Winter Haven; the theater offers acting and movement training.

Sherman's Antique

Winter Haven has a plethora of antique shops. On the other hand, Sherman's Antiques is the greatest in town. The vast multi-level antiquities store is overflowing with ancient treasures. From the outside, it may not look like much, but soon as you get past the crowded front area, you'll uncover an entire universe of antique delights.

The shop, operating for over two decades now, is around 10,000 square feet, with approximately 35 vendors exhibiting anything from pocket watches to paintings, China sets, and vintage toys.

Vintage doll restoration is one of Sherman's Antiques' expertise, with the shop featuring a Doll Hospital, which has been in business for 40 years.

The Village Sampler, Central Avenue Antiques, and Treasure House Antiques are three more antique outlets to visit while in town.

The Fantasy of Flight

If you're an aviation buff, The Fantasy of Flight, a museum dedicated to antique aircraft from various eras, is a must-visit. This enormous hangar museum features a stunning collection of planes dating back to the 1900s, including the 1909 Herring-Curtiss Pusher and the 1911 Valkyrie.

You'll also come across a collection of Golden Age planes and aircraft used in World War I and World War II planes. Surprisingly, many of these aircraft are still operational and airworthy, and you may even see some taking off from the neighboring seaplane airstrip or runway.

Polk Museum of Art

The Polk Museum of Art, situated on the Florida Southern College campus in Lakeland, is a treasure trove of fantastic artworks. The museum, a short drive from Winter Haven, started more than five decades ago and now houses over 2,800 works of art by famous artists such as Picasso, Chagall, Warhol, and more.

Besides its permanent collection, the Polk Museum of Art offers an active roster of online exhibitions, educational events, and seasonal exhibits.

The Mayfaire by the Lake festival, a major outdoor arts event, is one of the museum's must-attend events and arguably the best in Florida.


Winter Haven wouldn't be able to consider itself a Florida city if it lacked access to beaches. Luckily, the city's well-known series of 50 lakes offers numerous beaches situated within the municipal borders.

Furthermore, you can also visit some of Florida's most stunning and well-known ocean beaches, like Clearwater Beach, which is only roughly an hour and a half drive away.

That means you have unlimited access to swimming, sailing, kayaking, fishing, sunbathing, and other activities that make up a pleasurable Florida lifestyle.

Good School Systems

Polk County Public School District is the 37th-largest in the US and the eighth-largest in The Sunshine State.

It boasts roughly 160 schools, including 16 senior high schools, 19 junior high/middle schools, and 65 elementary schools. Adult schools, charter schools, technical and vocational institutions, and other alternative schools are also covered.

There are roughly 95,000 students enrolled. With almost 12,000 workers, over half of them being teachers, the district is Polk County's largest employer.

Polk State College, a typical four-year college, provides comprehensive career options. The University of Tampa, the University of Central Florida, Webster University, Warner Southern College, Webber International University, the University of South Florida, Keiser College, and Florida Southern College are all within commuting distance. Ridge Technical Center and Traviss Technical Center are also other local technical institutions.

Exquisite Floridian Restaurants and Cuisine

Having a taste of Winter Haven's cuisine is something you'd certainly want to try. The city's dining scene is dynamic, offering you the most diverse selection of restaurants and foods.

If you're searching for good meals in a relaxed setting, Nutwood ought to top your Winter Haven dining list. This modern yet affordable American restaurant offers some delectable menu dishes at mid-range rates that will have your taste buds yearning for more. And since the weather is often fantastic in Winter Haven, you can choose to make the most out of your dining experience through their terrific patio seats.

Another popular restaurant in Winter Haven is Harry's Old Place, a typical Florida seafood restaurant with great water views and a relaxed atmosphere. Their daily fried fish "blackboard" varies, and you can request them to prepare their fresh catches in almost any manner you desire.

Arabella's, on the other hand, makes an ideal spot whenever you're in the mood for a spectacular lunch in Winter Haven. This upscale Italian restaurant serves your favorite meals freshly cooked in a setting that shouts "special occasion."

Convenience in Getting Around

Since Winter Haven has a suburban feel, you might want to bring your car to help get you around. Nonetheless, some parts of the town are purposely walkable.

Specifically, the recently revitalized downtown is meant to be pedestrian-friendly and provide quick access to its various stores and restaurants. Furthermore, specific neighborhoods, such as our Cypress Harbor neighborhood, allow you to conveniently and safely access amenities and visit neighbors.

The city also has its bus system known as Winter Haven Area Transit, which runs nine buses. The Polk County Citrus Connection transit system also operates four extra buses, allowing you to move around the city without needing to drive.


Of course, you want to feel safe and enjoy all the recreation and amenities your selected city offers.

Despite having a somewhat higher crime rate than the national average, Winter Haven has a crime rate of 4.16 offenses per 1,000 people. In addition, the city has a lower crime rate than the national average in categories such as burglary and motor vehicle theft.

Winter Haven is exceptionally safe on the city's southwestern and eastern outskirts. In these parts, you can enjoy living in confidence and security for a genuinely tranquil retirement.

Great Culture

Theatre Winter Haven has long been the center of the community's cultural life. It's undoubtedly one of Florida's most prominent community theater organizations. Wait till you find out what they have prepared for their fresh new Chain O' Lakes Complex!

There's also the Polk Theatre in Lakeland, which nearly always has a live musical event or an old film on the schedule.

Moreover, you may also visit the Florida Southern College near Lakeland, which boasts the most extensive single-site portfolio of Frank Lloyd Wright designs. And if you are interested in aviation, you can visit The Fantasy of Flight and check out some of their intriguing, ongoing antique aircraft restoration projects.

Proximity to Various Amenities

As you'd expect, Winter Haven doesn't lack in essential amenities, including:


Like most cities, Winter Haven features a general aviation airfield that you might be keen on if you intend to do your flying. But if you are seeking air transportation to and from Winter Haven, you have several options in the larger cities around the area.

Orlando International Airport (MCO), which is roughly an hour's drive and less than 40 miles from Winter Haven, is the closest. Other airports a little farther away are Orlando Sanford Airport (SFB) and Tampa International Airport.

Depending on your budget and time, you may commute to these airports by shuttle, bus, or car. That means you can get into and out of the city relatively fast.

Healthcare Facilities

Winter Haven does not have as many healthcare facilities as other larger cities like Tampa, Orlando, or Jacksonville. However, there exist several great choices, such as Winter Haven Hospital and Lakeland Regional Health Medical Center, which is only 30 minutes away in Lakeland.

You may also find other medical care options, from nursing homes to rehab centers and surgery facilities. So, regardless of your medical needs, expect convenient and easy access to excellent healthcare.


Winter Haven can also meet all of your postal needs. There is a post office in the city and multiple FedEx and UPS stations. If you opt to reside in a retirement community like Cypress Harbor, you may also do some postal service transactions directly within your neighborhood.


Managing your banking errands in Winter Haven is straightforward, owing to the convenient availability of several financial institutions. From regional institutions to lenders, banks, and credit unions, your bank of choice is most likely nearby.

As such, everything from obtaining a loan to withdrawing cash is simple to accomplish locally, allowing you to manage your savings effortlessly.

Pleasant Weather

Winter Haven got its name from its excellent year-round climate, which makes it a genuine getaway from the brutal winters of northern regions.

If you can manage some minor mugginess mid-year, you may enjoy mild temperatures that make life in this town and state a very pleasurable experience.

Hand choose a wooden house on green grass

Real Estate and Cost of Living in Winter Haven, Florida

Winter Haven has an 88.1 cost of living index, slightly below the national average of 100, and even farther below the state of Florida's 102.8.

An area's median house selling price is a crucial element of the cost-of-living index. While Florida's median home selling price in 2021 was $348,000, the Lakeland-Winter Haven Metropolitan Statistical Area's median home selling price was $275,000 during the same period.

So, if you're trying to find out where in Florida you can get the most value for your money in terms of housing and stretch a dollar farther once you're here, you couldn't do much better than the Winter Haven region right now.

Best Neighborhoods in Winter Haven, Florida

If you're looking to move to Winter Haven, Florida, you have plenty of great neighborhoods and properties to pick from. There's something for everyone, from golf community homes to homes on the chain of lakes and luxury homes.

A few notable neighborhoods to check out in Winter Haven include:


Terranova is a lovely gated community with an entrance on Eloise Loop Road. When driving past, you will note the many beachfront and lakeside homes within, and even typical homes, all in a traditional neighborhood setting.

Suppose you choose to live here; you'll enjoy convenient proximity to shopping centers like Walmart, Publix, or Winn Dixie, among other amenities.

Lake Somerset

Living in Lake Somerset provides homeowners a dense suburban atmosphere, and most people here own their houses.

Even more impressive, the neighborhood boasts plenty of parks and restaurants, proximity to various amenities, and above-average school systems, all of which make the quality of life worthwhile.

Florence Villa

Florence Villa is another notable suburban neighborhood in the Lakeland/Winter Haven area. It boasts proximity to an array of parks, including Grant Park and McKay Bay Nature, which provide fantastic playgrounds and leisure opportunities for kids and adults alike.

Families can also walk along the trail for a social outing or enjoy wonderful picnics under the shade during summer.

What's Next?

This article shows that Winter Haven, Florida, is a remarkable place to buy a property and live. And suppose you've always dreamt of living by the lake; it might just be the proper city for you, given its chain of roughly 50 lakes scattered all over the city.

Additionally, it boasts small-town vibes, offers excellent affordability, and cuts it among Florida's fastest-growing cities. With all these perks, and all the information gathered in this piece, moving to Winter Haven is a no-brainer.

With over 50 years of mortgage industry experience, we are here to help you achieve the American dream of owning a home. We strive to provide the best education before, during, and after you buy a home. Our advice is based on experience with Phil Ganz and Team closing over One billion dollars and helping countless families.

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