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New 55+ Communities in Winter Haven

by Andrew Selby | Updated: February 9, 2023

Located just 50 miles east of Tampa and about the same distance southwest of Orlando, Winter Haven is the perfect location for retirees who are looking to get away from the big cities but still be close enough to visit whenever they want.

Winter Haven is also home to exciting outdoors and water sports opportunities, an award-winning community theater program, some of the best antique shopping in Florida, and a wide range of excellent dining options for all occasions.

Where to Retire in Winter Haven

Winter Haven has a wide variety of community and housing types to offer, but currently only one new 55+ community is being developed:

Lake Ashton – Winter Haven, FL

Set on over 1,200 scenic acres, amongst three spectacular lakes and nature preserves, Lake Ashton offers a great retirement lifestyle in the heart of Florida. This award-winning, 24-hour manned gated community is tucked between Tampa and Orlando.

Lake Ashton has two 18-hole golf courses, a 26,000 sq. ft. main clubhouse, a 30,000 sq. ft. fitness center, community pools, pickleball, and tennis courts, and so much more.

New homes and resales are available from the $300k's.

Request more information

Other Winter Haven 55+ Communities

Other popular 55+ communities include Traditions at Lake Ruby, Vienna Square, and several more. Here are some homes in various Winter Haven 55+ communities currently on the market:

400 El Camino Drive Winter Haven FL 33884
New Listing - 7 hours online
1 / 9
$89,999
Condo For Sale
Active
1
BED
2
TOTAL BATHS
768
SQFT
400 El Camino Drive #211
Winter Haven, FL 33884
Orchid Spgs Vill 400 San Miguel Subdivision
4146 Bedford Avenue Winter Haven FL 33884
Open House Sat, Mar 25, 6 AM UTC
1 / 33
$334,999
Single Family Home For Sale
Active
2
BEDS
2
TOTAL BATHS
1,819
SQFT
4146 Bedford Avenue
Winter Haven, FL 33884
Traditions Ph 01 Subdivision
150 El Dorado Winter Haven FL 33884
New Listing - 7 days online
1 / 39
$144,900
Condo For Sale
Active
2
BEDS
2
TOTAL BATHS
1,372
SQFT
150 El Dorado #107
Winter Haven, FL 33884
Hawaiian A Condo Subdivision
2600 Lucerne Park Road Winter Haven FL 33881
New Listing - a week online
1 / 13
$139,900
Condo For Sale
Active
2
BEDS
2
TOTAL BATHS
845
SQFT
2600 Lucerne Park Road #508
Winter Haven, FL 33881
Lake Point Landing Subdivision
2600 Lucerne Park Road Winter Haven FL 33881
New Listing - a week online
1 / 15
$129,900
Townhouse For Sale
Active
2
BEDS
2
TOTAL BATHS
845
SQFT
2600 Lucerne Park Road #505
Winter Haven, FL 33881
Lake Point Landing Subdivision
3987 Bedford Avenue Winter Haven FL 33884
New Listing - a week online
1 / 32
$375,000
Single Family Home For Sale
Active
2
BEDS
2
TOTAL BATHS
1,817
SQFT
3987 Bedford Avenue
Winter Haven, FL 33884
Traditions Ph 02 Subdivision
1700 6th Street NW Winter Haven FL 33881
New Listing - a week online
1 / 46
$75,000
Condo For Sale
Active
1
BED
1
TOTAL BATH
640
SQFT
1700 6th Street NW #C3
Winter Haven, FL 33881
Winter Haven Harbour Apts Condo Subdivision
4500 Grayhawk Drive Winter Haven FL 33884
New Listing - 2 weeks online
1 / 100
$449,900
Single Family Home For Sale
Active
3
BEDS
2
TOTAL BATHS
1,840
SQFT
4500 Grayhawk Drive
Winter Haven, FL 33884
Lake Ashton West Ph I Subdivision
150 El Dorado Winter Haven FL 33884
New Listing - 2 weeks online
1 / 48
$135,000
Condo For Sale
Active
2
BEDS
2
TOTAL BATHS
1,372
SQFT
150 El Dorado #206
Winter Haven, FL 33884
Hawaiian A Condo Subdivision
4076 Carteret Drive Winter Haven FL 33884
New Listing - 2 weeks online
1 / 52
$285,000
Single Family Home For Sale
Active
2
BEDS
2
TOTAL BATHS
1,605
SQFT
4076 Carteret Drive
Winter Haven, FL 33884
Traditions Ph 01 Subdivision
10 Kendra Court Winter Haven FL 33880
New Listing - 2 weeks online
1 / 33
$145,000
Villa For Sale
Active
2
BEDS
2
TOTAL BATHS
953
SQFT
10 Kendra Court
Winter Haven, FL 33880
Brandy Chase Village A Rep Subdivision
3655 Plymouth Drive Winter Haven FL 33884
New Listing - 2 weeks online
1 / 51
$365,000
Single Family Home For Sale
Active
3
BEDS
2
TOTAL BATHS
1,873
SQFT
3655 Plymouth Drive
Winter Haven, FL 33884
Traditions Ph 02 Subdivision
1776 6th Street NW Winter Haven FL 33881
New Listing - 2 weeks online
1 / 21
$144,900
Condo For Sale
Active
2
BEDS
2
TOTAL BATHS
1,347
SQFT
1776 6th Street NW #107
Winter Haven, FL 33881
Lakeridge Condo Subdivision
333 Lake Howard Dr NW Winter Haven FL 33880
New Listing - 3 weeks online
1 / 34
$159,999
Condo For Sale
Active
3
BEDS
2
TOTAL BATHS
1,226
SQFT
333 Lake Howard Dr NW #204 D
Winter Haven, FL 33880
Imperial Harboursphases 01 & 02 Subdivision
4043 Bedford Avenue Winter Haven FL 33884
New Listing - 4 weeks online
1 / 57
$374,900
Single Family Home For Sale
Active
2
BEDS
2
TOTAL BATHS
1,871
SQFT
4043 Bedford Avenue
Winter Haven, FL 33884
Traditions Ph 02 Subdivision
6152 Pebble Beach Boulevard Winter Haven FL 33884
New Listing - 4 weeks online
1 / 71
$499,900
Single Family Home For Sale
Active
3
BEDS
2
TOTAL BATHS
2,045
SQFT
6152 Pebble Beach Boulevard
Winter Haven, FL 33884
Lake Ashton West Ph Ii North Subdivision
2860 Attwater Loop Winter Haven FL 33884
1 / 25
$240,000
Villa For Sale
Active
2
BEDS
2
TOTAL BATHS
1,385
SQFT
2860 Attwater Loop
Winter Haven, FL 33884
Traditions Ph 2a Subdivision
100 El Camino Drive Winter Haven FL 33884
1 / 17
$115,900
Condo For Sale
Active
1
BED
1
TOTAL BATH
1,078
SQFT
100 El Camino Drive #305
Winter Haven, FL 33884
Orchid Springs Village 100 Condo Subdivision
4019 Carteret Drive Winter Haven FL 33884
Open House Sat, Apr 1, 4 AM UTC
1 / 32
$300,000
Single Family Home For Sale
Active
3
BEDS
2
TOTAL BATHS
1,719
SQFT
4019 Carteret Drive
Winter Haven, FL 33884
Traditions Ph 01 Subdivision
3023 Caneel Street Winter Haven FL 33884
1 / 52
$251,500
Villa For Sale
Active
2
BEDS
2
TOTAL BATHS
1,385
SQFT
3023 Caneel Street
Winter Haven, FL 33884
Traditions Ph 2a Subdivision

For more information on what options might be available in your desired price range, just fill out this form:

Fill out my online form.

Getting to Winter Haven

As I mentioned, Winter Haven is pretty much equidistant to Tampa and Orlando, so you could potentially fly into either Orlando International Airport or Tampa International Airport.

It's a pretty easy drive from anywhere within Central Florida to get to Winter Haven, as it sits about 10 miles south of I-4.


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Winter Haven History

The area that would eventually become known as Winter Haven was originally home to the Timucua and Calusa tribes. It was also inhabited by various Seminole tribes throughout the 19th century. Railroad expansion in the middle of that century brought the first settlers to the area which was eventually named Winter Haven because of its comfortable year-round climate.

While there was some growth in the area during the early 1900s, things really began to take off in Winter Haven following World War II. During this century, the town welcomed the very first Publix supermarket, a large citrus packing plant, and the visually stunning Cypress Gardens, which would eventually become today's Legoland.

Winter Haven Cost of Living

With a cost of living index of 88.1, Winter Haven is quite a bit under the national average (100) in this department, and even further under Florida's cost of living index of 102.8.

A large component of the cost of living index is an area's median home sales price. While the median sales price for Florida as a whole in 2021 was $348,000, the median home sales price in the Lakeland-Winter Haven Metropolitan Statistical Area for the same time period was $270,000.

So if you are trying to figure out where in Florida you can get the most bang for your buck housing-wise, and also be able to stretch a dollar further once you get here, you can't do too much better right now than the Winter Haven area.

Winter Haven Healthcare

Admittedly you won't find as many healthcare options in Winter Haven as you would in bigger cities like Orlando, Tampa, or Jacksonville. But there are some decent options available, including Winter Haven Hospital, and Lakeland Regional Health Medical Center is about 30 minutes away in Lakeland.


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Winter Haven Weather

As the name suggests, it's a Haven in the Winter. Here’s a look at the average low and high temperatures in Winter Haven throughout the year:

MonthAvg. LowAvg. High
January5173
February5276
March5780
April6084
May6689
June7191
July7392
August7392
September7290
October6686
November5979
December5375
Avg. temps in degrees Fahrenheit. Source: NOAA

Winter Haven Lifestyle

The Winter Haven lifestyle is all about getting out on the water and enjoying more than 55 lakes that you will find across the region. That means that everything from waterskiing and wakeboarding to kayaking and standup paddleboarding is available here throughout the year.

Tripadvisor has a good list of the best things to do in Winter Haven.

Winter Haven Culture

Theatre Winter Haven has long been the heart of the cultural side of the community. Here you will find one of the most decorated community theatre organizations in all of Florida, and just wait until you see what they have planned for their brand new Chain O' Lakes Complex!

There is also the Polk Theatre located right down the road in Lakeland, which almost always has an old film or live musical performance on its calendar.

Nearby Lakeland is also the home of Florida Southern College, which houses the largest single-site collection of Frank Lloyd Wright designs, and you can find some exciting vintage aircraft restoration projects happening at The Fantasy of Flight.

Winter Haven Dining

If delicious food in a casual environment is what you are looking for, Nutwood should be at the top of your bucket list for dining in Winter Haven. This modern American restaurant boasts some high-end menu items at mid-range prices that keep your palate coming back for more. And since the weather is always great in Winter Haven, you can usually make use of their lovely patio seating.

Another favorite restaurant in the area is Harry's Old Place, which is the classic Florida seafood restaurant that offers the perfect combination of a casual environment and stunning views of the water. Their fried fish “blackboard” changes every day, and you can get their fresh catches prepared just about any way you like.

When you are ready for a special meal in Winter Haven, Arabellas is the ultimate destination. This high-end Italian restaurant offers all of your favorite dishes prepared perfectly in an environment that just screams “special occasion.”


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With everything that Winter Haven has to offer, it is no surprise that it has developed a reputation as one of the best destinations for retirees. If you are looking for an option between Tampa and Orlando, this lovely town offers a unique hybrid combination of both.

Reader Interactions

Comments

  1. Debra Miller says

    September 15, 2022 at 3:07 pm

    Thanks for information regarding Winter Haven! That’s exactly what I been looking for a Winter Haven. Some place to go and enjoy being retired in the winters to get away from Northwest Indiana winters. Even though should say Chicago since were only about an hour away from the big cold Windy City and the frozen lake..

    Reply
  2. Mike and Lynn Schlies says

    October 15, 2019 at 10:04 am

    Thank you for all the great information you share. We are researching FL, and your blog helps us determine whether or not we will move here. I appreciate you!

    Reply

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