Homes For Sale in Winter Haven FL

Tue, Jan 02, 2024 at 10:20AM

Homes For Sale In Winter Haven FL & Real Estate

Homes For Sale in Winter Haven FL: Nestled between Tampa and Orlando, Winter Haven Florida is a hidden gem offering an abundance of attractions, delicious dining, a rich arts and culture scene, unique shopping experiences and a thriving real estate market. Discover why this city’s picturesque landscape, vibrant community, and lakeside charm make it a must-visit destination or even a place to call home.

Winter Haven Summary

  • Explore Winter Haven, FL for exciting attractions & activities, outdoor adventures and nightlife
  • Enjoy local eateries and cafes plus unique shopping finds in a vibrant city full of art, culture & history
  • Now is the time to find your dream home in Winter Haven’s growing real estate market with quality schools. See the following houses for sale under the price of 100k, under 200k, under 300k, under 400k, under 500k, under 600k, under 700k, under 800k, under 900k.
  • Find your next home by searching by number of bedrooms. 2 bedrooms, 3 bedrooms, 4 bedrooms or 5 bedrooms or more.
  • Types of homes for sale, Mobile Homes , Condos, Waterfront homes and all others.
  • Most popular zip codes with homes for sale 33880 , 33881 and 33884. Even Land For Sale. Customize Your Own Search.

Discovering Winter Haven: Top Attractions and Activities Near Any Homes For Sale in Winter Haven Florida

Aerial view of Winter Haven area with LEGOLAND Florida Resort and Peppa Pig Theme Park Florida

Winter Haven offers a diverse array of attractions and activities that cater to all age groups and interests. The city’s convenient location between Tampa and Orlando makes it easily accessible for residents and visitors alike, while its stunning lakes and rolling hills paint a picturesque backdrop for adventure-seekers in Winter Haven, FL.

From the exhilarating thrills of theme parks to the world-renowned water skiing scene, Winter Haven has something for everyone. Whether you’re looking for:

  • a family-friendly day out

  • an adrenaline-filled adventure

  • a relaxing getaway

  • a cultural experience

Winter Haven has it all. Come and explore all that this vibrant city has to offer, including Downtown Winter Haven.

LEGOLAND Florida Resort & Peppa Pig Theme Park Florida

LEGOLAND Florida Resort & Peppa Pig Theme Park Florida, operated by Merlin Entertainments Group, are must-visit destinations for families in search of fun and adventure. These parks offer an assortment of themed hotels like the LEGOLAND Hotel and Peppa Pig Hotel, ensuring an immersive and memorable experience for the entire family. With rides and attractions like Brickbeard’s Watersport Stunt Show on Lake Eloise, these parks provide a day full of excitement and entertainment.

Beyond the rides and attractions, LEGOLAND Florida Resort also pays homage to its predecessor, Cypress Gardens by preserving its iconic botanical gardens. The beautiful gardens provide a serene escape from the excitement of the park while showcasing Winter Haven’s rich history.

Water Ski Capital of the World

Winter Haven has earned its title as the Water Ski Capital of the World, thanks in large part to the efforts of Dick Pope Sr. who used water skiing to promote his Cypress Gardens theme park in the 1930s. Today, the city is proud to be associated with 10 members of the Water Ski Hall of Fame – an unrivalled amount compared to any other city in the world. This is truly a testament to its historic significance and importance in the global ski community.

Lake Eloise at Cypress Gardens serves as the central hub for water skiing in Winter Haven providing an excellent location for both beginners and experienced water skiers to practice and perfect their skills. The city’s numerous lakes and interconnected canal system make it an ideal destination for water sports enthusiasts.

Outdoor Adventures and Lakeside Fun

Winter Haven’s Chain of Lakes offers a plethora of outdoor activities for residents and visitors to enjoy. Comprising 55 lakes, 24 of which are connected by canals, the Chain of Lakes provides ample opportunities for water-based fun. Some activities you can enjoy on the Chain of Lakes include:

  • Exploring the lakes by pontoon boat

  • Paddleboarding

  • Wakeboarding

  • Kayaking

For those who prefer a more leisurely pace, the many lakes in the region are also renowned for world-class bass fishing.

The lakeside lifestyle in Winter Haven offers:

  • Relaxation and enjoyment

  • Unwinding on a dock

  • Savoring a glass of wine or a locally brewed craft beer

  • Watching the sun set in a breathtaking display of orange and pink hues

  • Beautiful scenery

  • Inviting atmosphere

Winter Haven’s lakeside living is a dream come true, with the soothing sound of water adding to its charm.

A Taste of Winter Haven: Dining and Nightlife

People enjoying nightlife in Winter Haven Who purchased one of the homes for sale in Winter Haven FL

Winter Haven’s dining scene is as diverse as its attractions, offering a delectable array of local eateries, cafes, and nightlife options to suit every palate. From cozy coffee shops to upscale Italian restaurants, the city’s culinary landscape reflects its vibrant culture and community spirit.

The nightlife in Winter Haven is equally enticing, with live music venues, bars, and theaters providing a lively atmosphere for an unforgettable night out. Whether you’re in the mood for a casual drink with friends or a night of dancing and entertainment, Winter Haven has you covered.

Local Eateries and Cafes

The city’s local eateries and cafes offer a taste of Winter Haven’s unique culinary scene. Some options include:

These establishments showcase the city’s commitment to quality ingredients and local flavor, serving mouthwatering dishes in a welcoming atmosphere.

For a true taste of Winter Haven, don’t miss out on the Lakeland Pigfest held each January. This exciting event features more than 150 barbecue teams serving up a variety of delicious main dishes, sides, sauces, and desserts providing a delectable feast for all who attend.

Nightlife and Entertainment

Winter Haven’s nightlife and entertainment scene offers something for everyone, including:

  • Lively bars like Barrel 239 and Caribbean Bay

  • More laid-back options like Jessie’s and Jensen’s Corner Bar

  • Bowling alleys, movie theaters, and arcades for all ages

You’re guaranteed to have a fun-filled experience in Winter Haven.

No matter your preference, the Winter Haven area has a venue or activity to suit your taste.

Art, Culture, and History in Winter Haven

People enjoying arts and culture hotspots in Winter Haven

Winter Haven is a city rich in arts, culture, and history. From its vibrant art galleries and theaters to its historical landmarks, Winter Haven offers a unique blend of the past and present. Visitors can immerse themselves in the city’s artistic and cultural scene by exploring its galleries, theaters, Central Park and historical sites.

The city, located along Central Avenue, is home to a variety of art galleries, theaters and museums, each offering a different offering.

Arts and Culture Hotspots

The city’s arts and culture hotspots include community theaters like The Winter Haven Community Theatre, The Lakeland Community Theatre and The Polk Theatre, which showcase local talent and provide quality entertainment. Music venues such as The Haven Lounge, The Attic and The Music Box offer live performances and a lively atmosphere for music lovers.

Winter Haven is home to numerous art galleries, including:

  • Crow’s Nest Artisanal Wares

  • Ridge Art Association

  • Carroll Estate Gallery

  • Lake Wales Arts Center

  • Polk Museum of Art

These galleries display the work of local artists and provide a glimpse into the city’s thriving arts scene.

Historical Highlights

Winter Haven’s rich history spans from its agricultural roots to its transformation into a bustling city. The first Publix Food Store opened in Winter Haven in 1930, marking the beginning of the now-iconic grocery store chain. The city’s famous Cypress Gardens, which entertained millions of visitors from 1936 to 2009, is now the site of LEGOLAND Florida maintaining the spirit of the original gardens while offering new attractions for families to enjoy.

The city’s history is also intertwined with its present-day arts and culture scene. For example, the once-thriving African American neighborhood of Pughsville was home to a vibrant community that included schools, social halls and restaurants. The legacy of Pughsville lives on through its remaining historical landmarks and the continued celebration of its rich cultural heritage.

Shopping in Winter Haven: Unique Finds and Local Boutiques

People shopping in Winter Haven's local shops and boutiques

Shopping in Winter Haven provides a unique experience, with local boutiques and antique shops offering one-of-a-kind finds for every taste. From trendy clothing to vintage treasures, Winter Haven’s shopping scene is a treasure trove of distinctive items waiting to be discovered.

Local Shops and Boutiques

Winter Haven is home to a variety of local shops and boutiques, such as The Shop, Andy Thornal Company, and 417 Boutique by Cate. These stores offer a curated selection of clothing, accessories and home goods that reflect the city’s unique charm and individuality.

Whether you’re searching for the perfect gift or simply looking to treat yourself, Winter Haven’s local shops have something for everyone.

Antique Hunting

For antique enthusiasts, Winter Haven offers a wealth of opportunities to explore and uncover hidden treasures. Popular antique shops like Sherman’s Antiques, The Village Sampler, and Treasure House Antiques & Collectibles are filled with vintage finds that are sure to delight collectors and casual shoppers alike.

From rare furniture and home decor to one-of-a-kind trinkets, Winter Haven’s antique shops provide a shopping experience unlike any other.

Winter Haven Real Estate: Finding Your Dream Home


Winter Haven’s real estate market offers a diverse range of options for those looking to call the city home. From charming lakefront properties to modern downtown condos, Winter Haven has something to suit every lifestyle and budget. Surely one of the homes for sale in Winter Haven FL will catch your eye.

With its growing population and expanding real estate market, now is the perfect time to explore the city’s housing options and find your dream home with the help of a professional who holds real estate brokerage expertise.

Current Market Trends

Winter Haven’s real estate market is showing positive trends, including:

  • The median home price in May 2023 standing at $313,000, up 2.6% compared to last year

  • The city’s continued expansion and increasing demand for housing in the area

  • The number of homes for sale in Winter Haven has decreased slightly by 9.9% between April 2023 and May 2023

This makes it an opportune time for prospective properties consumers to explore the market with the help of a local mls brokerage, take advantage of the listing broker’s offer, and identify prospective properties consumers may be interested in.

Investors and homeowners alike can find value in Winter Haven’s real estate market, as the city has experienced an impressive 182.51% appreciation in property values over the last ten years. This equates to an average annual home appreciation rate of 10.94%, making Winter Haven one of the most promising markets for investors.

Schools and Education

For families considering a move to Winter Haven, the city’s educational offerings are an important factor to consider. Winter Haven’s public schools, operated by Polk County Public Schools, provide quality education for students from elementary to high school. Some top-rated public schools in Winter Haven include:

  • Lincoln Avenue Academy

  • Hartridge Academy

  • Polk Pre-Collegiate Academy

  • Chain of Lakes Collegiate High School

These schools offer excellent educational opportunities for students in the area.

In addition to its strong academic programs, Winter Haven’s schools provide a wealth of extracurricular activities, such as:

  • clubs

  • after-school programs

  • music

  • art

  • sports

These offerings enrich the educational experience for students and contribute to the city’s vibrant community.


Winter Haven, Florida, is a city that offers something for everyone, from its exciting attractions and diverse dining scene to its thriving real estate market and rich history. Whether you’re planning a visit or considering a move to the area, Winter Haven’s unique charm and lakeside allure are sure to captivate your heart and imagination.

Frequently Asked Questions

Is Winter Haven a good place to live in Florida?

Living in Winter Haven offers a unique opportunity to experience both small-town charm and Florida’s wonderful outdoor lifestyle. With its many lakes, lush vegetation and proximity to the attractions of Central Florida, Winter Haven is an ideal place to call home.

From families looking for a peaceful atmosphere to those seeking adventure, Winter Haven has something to offer everyone.

Is Winter Haven Florida a good place to retire?

Winter Haven is a great place to retire due to its beautiful lakefront views, abundance of outdoor activities, easy access to the larger cities of Orlando and Tampa and strong sense of community.

It’s the perfect mix of peacefulness and entertainment for those looking for a pleasant retirement destination.

What cities are between Orlando and Winter Haven?

It’s a pleasure to share that the journey between Orlando and Winter Haven is filled with great cities to explore, including Kissimmee, Lakeland, Lake Wales, Winter Park and Clermont.

How far is Winter Haven fl from the beach?

At just over an hour’s drive away, you can enjoy the beautiful beaches of Clearwater Beach from Winter Haven, FL. With a distance of 66.82 miles, Clearwater Beach is characterized by white sand beaches stretching for 2.5 miles (4 km) along the Gulf and sits on a barrier island. This makes it the perfect getaway for those living in Winter Haven. Enjoy the sun, sand and surf of Clearwater Beach, just a short drive away.

What county is Winter Haven FL in?

Winter Haven, Florida is located in Polk County. Home to a population of over 686,480 people, it is one of the fastest growing regions in the state and nation. With a total area of 2,000 square miles, Winter Haven is within Florida’s 15th congressional district, which encompasses parts of Hillsborough, Pasco and Polk counties. Contact us about any of the homes for sale in Winter Haven FL.

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All listing information is deemed reliable but not guaranteed and should be independently verified through personal inspection by appropriate professionals. Listings displayed on this website may be subject to prior sale or removal from sale; availability of any listing should always be independent verified. Listing information is provided for consumer personal, non-commercial use, solely to identify potential properties for potential purchase; all other use is strictly prohibited and may violate relevant federal and state law. The source of the listing data is as follows: Stellar MLS (updated 5/29/24 5:04 PM) |

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Winter Garden, Florida 34787

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