Winter Haven - Cypress Gardens Real Estate

Located just an hour southwest of Orlando, Winter Haven is a Central Florida gem that blends theme park excitement, lakeside leisure, and foodie-friendly experiences — all perfect for a family getaway. Home to LEGOLAND Florida Resort and the whimsical Peppa Pig Theme Park, it's also conveniently close to major attractions like Walt Disney World (30 miles away) and Bok Tower Gardens in nearby Lake Wales (just 18 miles away).

Dubbed the “Chain of Lakes City” and the “Water Ski Capital of the World,” Winter Haven boasts 50 lakes within or along its borders. Visitors can catch the legendary Cypress Gardens Water Ski Team in action on Lake Eloise, cruise the scenic waterways by boat, or rent kayaks, paddleboards, or a pontoon to explore the interconnected lakes — with plenty of chances to reel in some bass along the way. Prefer dry land? There are plenty of trails, parks, and birding spots to keep you exploring.

Back in town, Winter Haven’s arts and entertainment scene shines at venues like the Historic Ritz Theatre, the iconic Gram Parsons Derry Down, and Theatre Winter Haven — often hailed as one of the top community theaters in the country. Shoppers can browse charming local boutiques like Andy Thornal Company and 417 Boutique, while food lovers will find a range of flavors, from beloved waterfront spots like Harborside and Harry’s Old Place to the nostalgic Andy’s Igloo — serving up classic burgers, shakes, and ice cream since 1951. Want to sample a little bit of everything? Winter Haven Food Tours offers guided tastings through the city’s best bites.

Whether you're traveling with kids, a partner, or a group, Winter Haven has a place to stay for every style and budget — from the colorful Pirate Island Hotel, LEGOLAND Hotel, and LEGOLAND Beach Retreat to cozy campgrounds and RV parks.

Winter Haven - Cypress Gardens Listings Summary

Winter Haven - Cypress Gardens - Town vs. County Stats

Winter Haven - Cypress Gardens Real Estate Market Health

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1400 South International Parkway Suite 1020
Lake Mary, FL 32746

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MLS Logo All information deemed reliable but not guaranteed. All properties are subject to prior sale, change or withdrawal. Neither listing broker(s) or information provider(s) shall be responsible for any typographical errors, misinformation, misprints and shall be held totally harmless. Listing(s) information is provided for consumer's personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. The data relating to real estate for sale on this website comes in part from the Internet Data Exchange program of the Multiple Listing Service. Real estate listings held by brokerage firms other than LPT Realty Office may be marked with the Internet Data Exchange logo and detailed information about those properties will include the name of the listing broker(s) when required by the MLS. Copyright ©2026 All rights reserved. Last Updated: September 17, 2026 3:06 PM UTC Show More...

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MLS Logo All information deemed reliable but not guaranteed. All properties are subject to prior sale, change or withdrawal. Neither listing broker(s) or information provider(s) shall be responsible for any typographical errors, misinformation, misprints and shall be held totally harmless. Listing(s) information is provided for consumer's personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. The data relating to real estate for sale on this website comes in part from the Internet Data Exchange program of the Multiple Listing Service. Real estate listings held by brokerage firms other than LPT Realty Office may be marked with the Internet Data Exchange logo and detailed information about those properties will include the name of the listing broker(s) when required by the MLS. Copyright ©2026 All rights reserved. Last Updated: September 17, 2026 2:46 PM UTC Show More...

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