• Skip to primary navigation
  • Skip to main content
  • Skip to primary sidebar
  • Skip to footer
Florida for Boomers

Florida for Boomers

Guide to Florida Retirement Communities and Condos

  • About
  • Best Communities
  • Best Places
    • Central Florida
    • East Coast
    • Northeast Florida
    • Panhandle
    • Southeast Florida
    • Southwest Florida
    • West Coast
  • Free Newsletter
  • Recent Articles
  • Store
    • Florida Retirement Handbook
    • Florida Retirement Masterclass
    • My Book About The Villages
    • Pick the Right Place
  • Search

55+ Homes for Sale in Kissimmee

by Ryan Erisman | Updated: February 7, 2024

Located just south of Orlando, Kissimmee is consistently listed among the best places to retire.

To get a better sense of what the real estate market is like in Kissimmee, take a look at some of the 55+ homes currently on the market below.

Also, two of our featured communities are in Kissimmee, and both are worth a closer look:

Solivita is an award-winning retirement community in Central Florida’s attraction zone. No matter where you live within this lush gated 55-plus community in Kissimmee, you can easily walk, bike or drive your golf cart to indoor and outdoor dining venues, state-of-the-art spa and fitness complexes, pickleball or tennis courts, and other facilities for sports and games.

With two stunning championship golf courses, intimate neighborhood centers, softball field, miles of green space for walking and biking, and too many classes and clubs to count, you will have many ways to enjoy the Solivita life.

Home prices start in the $200k's.

Learn More About Solivita

Four Seasons at Orlando is a gated community of 557 single-family homes located in Kissimmee, Florida, just south of Orlando. Amenities here include a 14,000-square-foot clubhouse with a state-of-the-art fitness center and an arts and crafts room, as well as an outdoor swimming pool, pickleball courts, and access to the 18-hole Mystic Dunes Golf Club. 

There are 7 floorplans that range in size from 1,428 to 2,328 square feet. Prices start in the $400k’s.

Learn More About Four Seasons at Orlando

508 LAGO MATISSE STREET KISSIMMEE FL 34759
New Listing - 6 days on site
1 / 22
$367,000
IDX Logo for Stellar MLS
Single Family Residence For Sale
Active
3
BEDS
2
TOTAL BATHS
1,807
SQFT
508 LAGO MATISSE STREET
KISSIMMEE, FL 34759
SOLIVITA PH 5B Subdivision
448 SORRENTO ROAD KISSIMMEE FL 34759
New Listing - 6 days on site
1 / 62
$335,000
IDX Logo for Stellar MLS
Single Family Residence For Sale
Active
3
BEDS
2
TOTAL BATHS
2,141
SQFT
448 SORRENTO ROAD
KISSIMMEE, FL 34759
SOLIVITA PH 06B Subdivision
1880 SPRING SHOWER CIRCLE KISSIMMEE FL 34744
New Listing - a week on site
1 / 37
$349,990
IDX Logo for Stellar MLS
Single Family Residence For Sale
Active
2
BEDS
2
TOTAL BATHS
1,559
SQFT
1880 SPRING SHOWER CIRCLE
KISSIMMEE, FL 34744
TOHOQUA PH 5B Subdivision
2016 FLORA PASS PLACE KISSIMMEE FL 34747
New Listing - a week on site
1 / 60
$675,000
IDX Logo for Stellar MLS
Single Family Residence For Sale
Active
3
BEDS
2
TOTAL BATHS
2,202
SQFT
2016 FLORA PASS PLACE
KISSIMMEE, FL 34747
FOUR SEASONS/ORLANDO PH 2 Subdivision
1983 LIMESTONE TRAIL KISSIMMEE FL 34747
Open House Sat, Sep 12, 1 PM
1 / 35
$549,000
IDX Logo for Stellar MLS
Single Family Residence For Sale
Active
3
BEDS
2
TOTAL BATHS
2,202
SQFT
1983 LIMESTONE TRAIL
KISSIMMEE, FL 34747
FOUR SEASONS AT ORLANDO PH 3C & 3D Subdivision
1989 SPRING SHOWER CIRCLE KISSIMMEE FL 34744
New Listing - a week on site
1 / 32
$399,000
IDX Logo for Stellar MLS
Single Family Residence For Sale
Active Under Contract
3
BEDS
2
TOTAL BATHS
2,087
SQFT
1989 SPRING SHOWER CIRCLE
KISSIMMEE, FL 34744
TOHOQUA RESERVE Subdivision
1908 FLORA PASS PLACE KISSIMMEE FL 34747
Real Estate Owned
1 / 10
$349,900
IDX Logo for Stellar MLS
Townhouse For Sale
Active
2
BEDS
2
TOTAL BATHS
1,437
SQFT
1908 FLORA PASS PLACE
KISSIMMEE, FL 34747
FOUR SEASONS AT ORLANDO PH 2 Subdivision
2160 ANTILLES CLUB DRIVE KISSIMMEE FL 34747
New Listing - 2 weeks on site
1 / 30
$419,999
IDX Logo for Stellar MLS
Single Family Residence For Sale
Active
2
BEDS
2
TOTAL BATHS
1,778
SQFT
2160 ANTILLES CLUB DRIVE
KISSIMMEE, FL 34747
FOUR SEASONS AT ORLANDO PH 1 Subdivision
513 BARCELONA DRIVE KISSIMMEE FL 34759
New Listing - 2 weeks on site
1 / 50
$295,000
IDX Logo for Stellar MLS
Single Family Residence For Sale
Active
2
BEDS
2
TOTAL BATHS
1,574
SQFT
513 BARCELONA DRIVE
KISSIMMEE, FL 34759
SOLIVITA PH 04C SEC 02 Subdivision
205 BELL TOWER CROSSING WEST KISSIMMEE FL 34759
New Listing - 3 weeks on site
1 / 100
$254,500
IDX Logo for Stellar MLS
Single Family Residence For Sale
Active
2
BEDS
2
TOTAL BATHS
1,405
SQFT
205 BELL TOWER CROSSING WEST
KISSIMMEE, FL 34759
SOLIVITA PH IIB Subdivision
141 LEMON GROVE DRIVE KISSIMMEE FL 34759
New Listing - 4 weeks on site
1 / 78
$649,900
IDX Logo for Stellar MLS
Single Family Residence
Pending
4
BEDS
5
TOTAL BATHS
2,917
SQFT
141 LEMON GROVE DRIVE
KISSIMMEE, FL 34759
SOLIVITA PH 07C Subdivision
105 CUPOLA LOOP KISSIMMEE FL 34759
New Listing - 4 weeks on site
1 / 50
$399,000
IDX Logo for Stellar MLS
Single Family Residence For Sale
Active
2
BEDS
2
TOTAL BATHS
2,066
SQFT
105 CUPOLA LOOP
KISSIMMEE, FL 34759
SOLIVITA PH 02D Subdivision
7789 FOUR SEASONS BOULEVARD KISSIMMEE FL 34747
1 / 36
$549,000
IDX Logo for Stellar MLS
Single Family Residence For Sale
Active
3
BEDS
3
TOTAL BATHS
2,360
SQFT
7789 FOUR SEASONS BOULEVARD
KISSIMMEE, FL 34747
FOUR SEASONS AT ORLANDO PB 3B & 4A Subdivision
1896 FLORA PASS PLACE KISSIMMEE FL 34747
1 / 95
$420,000
IDX Logo for Stellar MLS
Townhouse For Sale
Active Under Contract
2
BEDS
2
TOTAL BATHS
1,557
SQFT
1896 FLORA PASS PLACE
KISSIMMEE, FL 34747
FOUR SEASONS AT ORLANDO PH 2 Subdivision
163 OLYMPUS WAY KISSIMMEE FL 34759
1 / 58
$474,000
IDX Logo for Stellar MLS
Single Family Residence For Sale
Active
4
BEDS
3
TOTAL BATHS
2,200
SQFT
163 OLYMPUS WAY
KISSIMMEE, FL 34759
SOLIVITA PH 5-A Subdivision
280 INDIAN WELLS AVENUE KISSIMMEE FL 34759
1 / 38
$374,900
IDX Logo for Stellar MLS
Single Family Residence For Sale
Active
2
BEDS
2
TOTAL BATHS
2,101
SQFT
280 INDIAN WELLS AVENUE
KISSIMMEE, FL 34759
SOLIVITA PH 07A Subdivision
1001 PLANTATION DRIVE C1 KISSIMMEE FL 34741
Price Change - 3 weeks ago
1 / 23
$149,900
IDX Logo for Stellar MLS
Condominium For Sale
Active
2
BEDS
1
TOTAL BATH
1,008
SQFT
1001 PLANTATION DRIVE C1
KISSIMMEE, FL 34741
HERITAGE HOUSE CONDOS Subdivision
159 CASAVISTA DRIVE KISSIMMEE FL 34759
Price Change - 2 days ago
1 / 51
$419,500
IDX Logo for Stellar MLS
Single Family Residence For Sale
Active
2
BEDS
2
TOTAL BATHS
1,771
SQFT
159 CASAVISTA DRIVE
KISSIMMEE, FL 34759
SOLIVITA Subdivision
230 BAY DRIVE KISSIMMEE FL 34759
1 / 56
$296,000
IDX Logo for Stellar MLS
Single Family Residence For Sale
Active
2
BEDS
2
TOTAL BATHS
1,489
SQFT
230 BAY DRIVE
KISSIMMEE, FL 34759
SOLIVITA PH 01 Subdivision
1647 KEY BAY TRAIL KISSIMMEE FL 34747
Short Sale
1 / 8
$325,000
IDX Logo for Stellar MLS
Townhouse For Sale
Active Under Contract
2
BEDS
2
TOTAL BATHS
1,557
SQFT
1647 KEY BAY TRAIL
KISSIMMEE, FL 34747
FOUR SEASONS AT ORLANDO PB 3B & 4A Subdivision
1994 SPRING SHOWER CIRCLE KISSIMMEE FL 34744
1 / 36
$435,000
IDX Logo for Stellar MLS
Single Family Residence For Sale
Active
3
BEDS
2
TOTAL BATHS
2,056
SQFT
1994 SPRING SHOWER CIRCLE
KISSIMMEE, FL 34744
TOHOQUA PH 5A Subdivision
1144 VIA GALUPPI STREET KISSIMMEE FL 34759
1 / 47
$365,000
IDX Logo for Stellar MLS
Single Family Residence For Sale
Active Under Contract
3
BEDS
2
TOTAL BATHS
1,723
SQFT
1144 VIA GALUPPI STREET
KISSIMMEE, FL 34759
SOLIVITA Subdivision
2316 PALM TREE DRIVE KISSIMMEE FL 34759
Price Change - 3 weeks ago
1 / 69
$282,000
IDX Logo for Stellar MLS
Townhouse For Sale
Active
2
BEDS
2
TOTAL BATHS
1,539
SQFT
2316 PALM TREE DRIVE
KISSIMMEE, FL 34759
SOLIVITA PH 05F Subdivision
518 DAVINCI PASS KISSIMMEE FL 34759
1 / 54
$346,000
IDX Logo for Stellar MLS
Single Family Residence For Sale
Active
2
BEDS
2
TOTAL BATHS
1,491
SQFT
518 DAVINCI PASS
KISSIMMEE, FL 34759
SOLIVITA PH 04C SEC 02 Subdivision
1974 SPRING SHOWER CIRCLE KISSIMMEE FL 34744
1 / 69
$447,000
IDX Logo for Stellar MLS
Single Family Residence For Sale
Active
3
BEDS
3
TOTAL BATHS
2,175
SQFT
1974 SPRING SHOWER CIRCLE
KISSIMMEE, FL 34744
TOHOQUA PH 5A Subdivision
1132 VIA GALUPPI STREET KISSIMMEE FL 34759
1 / 60
$364,500
IDX Logo for Stellar MLS
Single Family Residence For Sale
Active
3
BEDS
2
TOTAL BATHS
1,725
SQFT
1132 VIA GALUPPI STREET
KISSIMMEE, FL 34759
SOLIVITA PH 5D Subdivision
941 SHOREHAVEN DRIVE KISSIMMEE FL 34759
Price Change - 2 weeks ago
1 / 23
$299,995
IDX Logo for Stellar MLS
Single Family Residence For Sale
Active
3
BEDS
3
TOTAL BATHS
2,325
SQFT
941 SHOREHAVEN DRIVE
KISSIMMEE, FL 34759
SOLIVITA PH 02D Subdivision
1973 SPRING SHOWER CIRCLE KISSIMMEE FL 34744
Price Change - a week ago
1 / 35
$360,000
IDX Logo for Stellar MLS
Single Family Residence For Sale
Active
3
BEDS
2
TOTAL BATHS
1,701
SQFT
1973 SPRING SHOWER CIRCLE
KISSIMMEE, FL 34744
TOHOQUA PH 5A Subdivision
2071 LIMESTONE TRAIL KISSIMMEE FL 34747
1 / 89
$549,000
IDX Logo for Stellar MLS
Single Family Residence For Sale
Active Under Contract
3
BEDS
2
TOTAL BATHS
2,066
SQFT
2071 LIMESTONE TRAIL
KISSIMMEE, FL 34747
FOUR SEASONS AT ORLANDO PH 3C & 3D Subdivision
1598 WHITEWOOD COURT KISSIMMEE FL 34747
1 / 58
$445,000
IDX Logo for Stellar MLS
Single Family Residence For Sale
Active Under Contract
3
BEDS
2
TOTAL BATHS
2,066
SQFT
1598 WHITEWOOD COURT
KISSIMMEE, FL 34747
FOUR SEASONS AT ORLANDO PB 3B & 4A Subdivision
453 SORRENTO RD KISSIMMEE FL 34759
1 / 67
$499,900
IDX Logo for Stellar MLS
Single Family Residence For Sale
Active
3
BEDS
4
TOTAL BATHS
2,580
SQFT
453 SORRENTO RD
KISSIMMEE, FL 34759
SOLIVITA - PHASE VIB Subdivision
7624 SAND PIERRE COURT KISSIMMEE FL 34747
1 / 52
$319,000
IDX Logo for Stellar MLS
Single Family Residence For Sale
Active Under Contract
2
BEDS
2
TOTAL BATHS
1,437
SQFT
7624 SAND PIERRE COURT
KISSIMMEE, FL 34747
FOUR SEASONS AT ORLANDO PB 3B & 4A Subdivision
7774 FOUR SEASONS BOULEVARD KISSIMMEE FL 34747
Price Change - 3 weeks ago
1 / 99
$675,000
IDX Logo for Stellar MLS
Single Family Residence For Sale
Active
3
BEDS
2
TOTAL BATHS
1,969
SQFT
7774 FOUR SEASONS BOULEVARD
KISSIMMEE, FL 34747
FOUR SEASONS AT ORLANDO PB 3B & 4A Subdivision
162 TALL PINES PASS KISSIMMEE FL 34759
Price Change - 2 days ago
1 / 60
$299,900
IDX Logo for Stellar MLS
Single Family Residence For Sale
Active
2
BEDS
2
TOTAL BATHS
2,038
SQFT
162 TALL PINES PASS
KISSIMMEE, FL 34759
SOLIVITA - PHASE IIB Subdivision
813 GLENDORA ROAD KISSIMMEE FL 34759
Price Change - 4 weeks ago
1 / 63
$489,000
IDX Logo for Stellar MLS
Single Family Residence For Sale
Active
3
BEDS
3
TOTAL BATHS
2,454
SQFT
813 GLENDORA ROAD
KISSIMMEE, FL 34759
SOLIVITA PH 02D Subdivision
7637 SAND PIERRE COURT KISSIMMEE FL 34747
1 / 48
$394,500
IDX Logo for Stellar MLS
Townhouse For Sale
Active
2
BEDS
2
TOTAL BATHS
1,557
SQFT
7637 SAND PIERRE COURT
KISSIMMEE, FL 34747
FOUR SEASONS AT ORLANDO PB 3B & 4A Subdivision
172 ACADIA DRIVE KISSIMMEE FL 34759
1 / 67
$254,900
IDX Logo for Stellar MLS
Single Family Residence For Sale
Active
2
BEDS
2
TOTAL BATHS
1,392
SQFT
172 ACADIA DRIVE
KISSIMMEE, FL 34759
SOLIVITA PH 04B Subdivision
305 ROCK SPRINGS DRIVE KISSIMMEE FL 34759
1 / 63
$474,900
IDX Logo for Stellar MLS
Single Family Residence For Sale
Active
3
BEDS
3
TOTAL BATHS
2,454
SQFT
305 ROCK SPRINGS DRIVE
KISSIMMEE, FL 34759
SOLIVITA PH I Subdivision
308 BEACON AVENUE KISSIMMEE FL 34759
1 / 43
$310,000
IDX Logo for Stellar MLS
Single Family Residence For Sale
Active
2
BEDS
2
TOTAL BATHS
2,038
SQFT
308 BEACON AVENUE
KISSIMMEE, FL 34759
SOLIVITA PH IIA Subdivision
795 AVIARA LANE KISSIMMEE FL 34759
1 / 55
$429,000
IDX Logo for Stellar MLS
Single Family Residence
Pending
3
BEDS
3
TOTAL BATHS
2,427
SQFT
795 AVIARA LANE
KISSIMMEE, FL 34759
SOLIVITA PH 7E UN 2 Subdivision
699 GLENDORA ROAD KISSIMMEE FL 34759
1 / 56
$430,000
IDX Logo for Stellar MLS
Single Family Residence For Sale
Active
3
BEDS
3
TOTAL BATHS
2,450
SQFT
699 GLENDORA ROAD
KISSIMMEE, FL 34759
SOLIVITA PH 02D Subdivision
1192 VIA GALUPPI STREET KISSIMMEE FL 34759
1 / 26
$370,000
IDX Logo for Stellar MLS
Single Family Residence For Sale
Active
3
BEDS
2
TOTAL BATHS
1,723
SQFT
1192 VIA GALUPPI STREET
KISSIMMEE, FL 34759
SOLIVITA PH 5D Subdivision
2074 FLORA PASS PLACE KISSIMMEE FL 34747
Price Change - yesterday
1 / 60
$579,000
IDX Logo for Stellar MLS
Single Family Residence For Sale
Active
3
BEDS
2
TOTAL BATHS
2,130
SQFT
2074 FLORA PASS PLACE
KISSIMMEE, FL 34747
FOUR SEASONS AT ORLANDO PH 2 Subdivision
313 SANTA BARBARA LANE KISSIMMEE FL 34759
1 / 57
$445,000
IDX Logo for Stellar MLS
Single Family Residence For Sale
Active
2
BEDS
3
TOTAL BATHS
2,343
SQFT
313 SANTA BARBARA LANE
KISSIMMEE, FL 34759
SOLIVITA PH 07B2 Subdivision
619 TAPATIO LANE KISSIMMEE FL 34759
1 / 36
$559,999
IDX Logo for Stellar MLS
Single Family Residence For Sale
Active
5
BEDS
5
TOTAL BATHS
2,881
SQFT
619 TAPATIO LANE
KISSIMMEE, FL 34759
SOLIVITA PH 07C Subdivision

Reader Interactions

Leave a Reply Cancel reply

Your email address will not be published. Required fields are marked *

Primary Sidebar

Footer

Popular Articles

25 Best Places to Retire in Florida
Best Florida Retirement Communities
Cost of Living in Florida
Florida Property Taxes

Florida 55+ Communities

Jacksonville 55+ Communities
Ocala 55+ Communities
Orlando 55+ Communities
Tampa 55+ Communities
Full List of 55+ Communities

Popular Communities

The Villages
On Top of the World
Valencia Riverland
Del Webb Communities
Villages of Citrus Hills

Regions

Northeast Florida
Central East Coast
South Florida
Southwest Florida
Central West Coast
Central Florida
Panhandle/NW Florida

Copyright 2007-2026 Florida for Boomers

  • About
  • Advertising
  • Blog
  • Contact
  • Privacy Policy
  • Terms of Use