Winter Haven, Florida

Best Places to Retire in Florida


Winter Haven (population 26,500) is located in the heart of central Florida – 46 miles due east from Tampa, and 49 miles southwest of the city of Orlando.  It is less than 75 miles to Kennedy Space Center and to the beaches.  Lakeland, the nearest good-sized city (75,000), is 15 miles away. The county (Polk County) has a total population of nearly 500,000.

Winter Haven has roots back into the mid-1800s and began to form as an agricultural community in the 1880s.  The railroad came through soon after and the population grew to about 400, with citrus groves, floral nurseries, a canning factory, and became headquarters of the Florida Growers Association.  It matured as a community with its churches, social activities, a band, its own newspaper, and a theater, and was incorporated in 1911.

Winter Haven boomed, along with Florida, in the 1920s and by the mid-1930s tourism had become the major component of the local economy by the time Cypress Gardens had opened in 1936. The city, sometimes referred to as the Chain of Lakes City, is built in an area where there are 23 fresh-water lakes, with 14 of them linked together by a series of canals.  They offer world-class fishing, swimming, skiing and other water activities, and idyllic waterfront and water-view home sites. 

The egrets, ospreys, and other birds, together with moss covered cypress and oaks, and flowering plants, all add to the beauty of the area. There are many choices for outdoor activities, including more than three dozen golf courses, tennis, adult athletic teams, and much, much more. Winter Haven is less than five miles from world famous Cypress Gardens, and it is the spring training home of the Cleveland Indians.

Winter Haven offers a comfortable lifestyle, somewhat away from the urban scene, surrounded by citrus groves and gentle rolling land. Yet it is close enough to easily enjoy the amenities they have to offer.  There is good shopping, many dining choices, including upscale restaurants, cultural activities, and many civic events.

The area enjoys a stable economic base with environmentally friendly industries, including tourism, a number of large regional distribution centers, agriculture, cattle, and light industry.  The cost of living in Polk County is 95.93% of the state’s average. Winter Haven was ranked in 2000 as the 17th most affordable place to live in the US by National Home Builders Association.

Arts & Culture

Lake Wales Little Theatre (15 mi.) is a 139-seat theater that provides dramatic, comedic, and musical productions, as well as an active program for young people and drama students.

Theatre Winter Haven offers eight high-quality performances of popular shows annually.

Lakeland Center (15 mi.) is a regional convention center.  It is a premier venue for conventions, sports events, and entertainment.  It offers 100,000 sq. ft. of convention and exhibitor space, a 2,296-seat theatre, and a 10,000-seat arena.

Imperial Symphony Orchestra, with a history of near 40 years, performs at the Lakeland Center.   

Polk Theatre (Lakeland) offers a Performing Arts Series, as well as hosting films.

Lakeland Concert Band has been performing since 1978.  Its performances are at the Youkey Theatre, Lakeland Center. 

Ridge Art Association offers exhibits at its gallery and offers programs that contribute to the cultural growth of the community.  

Lake Wales National Historic District offers very interesting shops, galleries, and antique stores.  It also has some of the area’s finest restaurants. 

The Depot ñ Lake Wales Museum & Cultural Center 

Ridge Live Steamers in nearby Dundee preserves the railroad heritage.  


Historic Bok Sanctuary (Lake Wales area), with a majestic carillon tower, stands on the highest point in Florida — 295-foot Iron Mountain.  The carillon, with 57 bronze bells weighing from 17 pounds to 12 tons, is surrounded by 157-acres of gardens.  There are tours and daily carillon recitals.  

Polk County has more than 36 golf courses and a wide range of tournaments, including the Champion’s Professional Tour. It is an outstanding golfing area with a good number of uncrowded courses in parts of the county. The Cleveland Indians long-time home for training is Chain of Lakes Park in Winter Haven. The park seats 7,000.  

Fantasy of Flight in Polk City features vintage aircraft of WW I and WW II and full motion flight simulators.  It also offers biplane and balloon rides.

Historic Cypress Gardens is now owned by Polk County.  The 30-acre park features its botanical gardens and ski show, and includes additional rides and a new water park. 


Florida Southern College, Lakeland, Fla., is a four-year private school.

Southeastern College, Lakeland, Fla., is a Christian college.

Warner Southern College, Lake Wales, Fla., is a Christian liberal arts college.

Senior Programs

Theatre Winter Haven offers a Senior Theatre Program called ACT IV Players, which tours retirement homes and community centers Winter Haven Senior Center  (863) 291-5870


Winter Haven Hospital is the major medical center for eastern Polk County.  It is an acute care medical facility with 759-beds. There are eight hospitals, 10 clinics, and more than 900 physicians and dentists in the county.


Tampa International Airport –

Orlando International Airport –


The News Chief –

Property Taxes

Polk County –


Lakeland -15 miles

Lake Wales – 15 miles

Kissimmee – 38 miles

Orlando – 46 miles

Tampa – 49 miles

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