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New 55+ Communities in Kissimmee

by Ryan Erisman | Updated: January 15, 2025

See also:
25 Best Places to Retire in Florida
Ultimate List of 55+ Communities in Florida

If one of your concerns is that you move to Florida for retirement and your kids and grandkids never come to visit, that won't be the case if you end up in Kissimmee.

In fact, you might have a hard time getting them to leave!

Kissimmee is located just south of Orlando and is just minutes from popular attractions like the Walt Disney World Resort, Universal Studios, Sea World, and more.

They call Kissimmee the “attraction zone” and it's easy to see why.

Where to Retire in Kissimmee

Located right next to Kissimmee, The Lakes at Harmony is a 55 and Better community from Jones Homes USA. Residents enjoy beautiful homes with the latest designs, technology, and included luxury features. Experience active living at its best, with Harmony’s signature golf course, Town Center, community events, walking trails, and more.

Harmony is more than a community, it’s a way of life; where the peace and tranquility of small-town living is surrounded by pristine lakes, abundant natural areas, popular Town Square and exclusive amenities, all close to the excitement and activities of nearby Orlando.

In addition to Harmony's outstanding amenities and convenient location, all homes by Jones Homes USA are built for the way you live today, with oversized kitchens, open living spaces and incredible included luxury features. With its perfect blend of small-town living, outstanding amenities, convenient location and, of course, extraordinary homes from Jones Homes USA, everyone wants to live in Harmony. 

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Here are some homes currently listed for sale in 55+ communities around Kissimmee:

1873 SPRING SHOWER CIRCLE KISSIMMEE FL 34744
New Listing - 23 hours on site
1 / 18
$365,000
Townhouse For Sale
Active
3
BEDS
2
TOTAL BATHS
1,559
SQFT
1873 SPRING SHOWER CIRCLE
KISSIMMEE, FL 34744
TOHOQUA PH 5B Subdivision
1130 SABINE LANE KISSIMMEE FL 34759
New Listing - yesterday
1 / 44
$289,000
Single Family Residence For Sale
Active
3
BEDS
2
TOTAL BATHS
1,487
SQFT
1130 SABINE LANE
KISSIMMEE, FL 34759
POINCIANA NBRHD 06 VILLAGE 07 Subdivision
159 CASAVISTA DRIVE KISSIMMEE FL 34759
New Listing - yesterday
1 / 56
$445,000
Single Family Residence For Sale
Active
2
BEDS
2
TOTAL BATHS
1,771
SQFT
159 CASAVISTA DRIVE
KISSIMMEE, FL 34759
SOLIVITA Subdivision
448 GRAND CANAL DRIVE KISSIMMEE FL 34759
New Listing - 5 days on site
1 / 34
$265,000
Single Family Residence For Sale
Active
2
BEDS
2
TOTAL BATHS
1,504
SQFT
448 GRAND CANAL DRIVE
KISSIMMEE, FL 34759
SOLIVITA Subdivision
1062 UMBRIA DRIVE KISSIMMEE FL 34759
New Listing - 5 days on site
1 / 46
$350,000
Single Family Residence For Sale
Active
2
BEDS
2
TOTAL BATHS
1,655
SQFT
1062 UMBRIA DRIVE
KISSIMMEE, FL 34759
SOLIVITA PH 5C Subdivision
203 LARKSPUR COURT KISSIMMEE FL 34743
New Listing - 5 days on site
1 / 3
$355,000
Single Family Residence For Sale
Active
3
BEDS
2
TOTAL BATHS
1,257
SQFT
203 LARKSPUR COURT
KISSIMMEE, FL 34743
BVL UNIT 2 Subdivision
615 DAVINCI PASS KISSIMMEE FL 34759
New Listing - 7 days on site
1 / 74
$374,900
Single Family Residence For Sale
Active
3
BEDS
3
TOTAL BATHS
2,276
SQFT
615 DAVINCI PASS
KISSIMMEE, FL 34759
SOLIVITA PH IVC SEC 02 Subdivision
1936 SPRING SHOWER CIRCLE KISSIMMEE FL 34744
New Listing - 7 days on site
1 / 30
$414,650
Single Family Residence For Sale
Active
2
BEDS
2
TOTAL BATHS
1,981
SQFT
1936 SPRING SHOWER CIRCLE
KISSIMMEE, FL 34744
TOHOQUA RESERVE Subdivision

Where to Stay

You've got plenty of options when coming to town to visit and tour communities, but one place stands out, at least for me, and that's Gaylord Palms. It's part of the Marriott family, and 9 times out of 10 it's where I stay with my family when we visit the area.

Staying at the Gaylord is like getting a mini-tour of Florida, as the resort is divided into different themed areas that represent different parts of Florida like the Everglades, St. Augustine, and Key West. You really have to see it to believe it.

Also, every year at Christmastime they have an event called ICE, where you get to walk through a 9-degree indoor winter wonderland complete with ice carvings, ice slides, and more. This event is popular with people from communities like The Villages and others, and they come in by the busload just for this event.

Theme Parks

wdw-entrance

Kissimmee is literally just minutes from the front door of the Walt Disney World Resort and its various parks like Walt Disney World, Epcot, Animal Kingdom, and Hollywood Studios.

About a 15-minute drive away are two more parks in Universal Studious and Islands of Adventure, and right down the road from there you also have Sea World.

Like I said before, with easy access to all of these parks, your guests may never want to leave.

But don't just think these parks are only for the young ones. Some of the best times I've had have been while visiting them with just my wife and I.

One of our favorite events is the Epcot Food and Wine festival held over several weeks each Fall. If you enjoy good food, exploring new wines and beers, this is a can't miss event.

epcot-food-wine

Planning to Work in Retirement?

Lots of people, even if they didn't initially plan to, end up getting part-time work in retirement.

Sometimes this is to make a little extra money to pay for trips they want to take or to cover some bills, and other times it's just to stay active and keep a routine going.

But whatever the reason, the theme parks are a great place for retirees to consider working, and they employ thousands of retirees as part-time employees already.

In addition to the pay, they offer some great perks like free park admission and other discounts that can come in handy when friends and relatives do visit.

Reader Interactions

Comments

  1. TK Love says

    March 1, 2020 at 2:55 pm

    Wife is not over 55 even though I am. Is that a problem?

    Reply

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