Real Estate Investing in Kissimmee, Florida (34744)
Everything the listing leaves out — vacancy, rent trend, cap rate, landlord climate. All free.
Should you buy in 34744 (Kissimmee, FL)? Our answer, based on the numbers below.
Mixed — home prices are stretched relative to local incomes. Run the math on your specific situation.
A cash-flow market — rent-to-price math works from day one, though value growth is modest. Great for income-focused investors.
- Elevated vacancy: 10.3% vacancy may signal weakening demand.
What’s happening in Kissimmee, FL (34744)?
Click any question — our AI will research it live from the web and show you sources.
Market Analysis: 34744 Kissimmee
ZIP 34744 inside Osceola County looks affordable on the surface — median value of $386K — but the discount exists for reasons that a careful buyer should understand before committing.
The 34744 ZIP can work — but only with a tight operating hand. Remote landlords and passive investors tend to struggle here more than the underwriting suggests.
Put differently, 34744 offers a low basis, the region around Kissimmee has moved on in ways that the ZIP itself has not fully absorbed. The result is a discount with genuine reasons.
The 34744 ZIP's population of 62,756 has faced economic pressure over the last decade. That pressure shows up in rent delinquency patterns that clocks in at the need for careful underwriting.
looks to the ZIP is not uninvestable, but it is unforgiving. Section 8 landlords, local operators, and specialized value-add funds are the investor types that tend to succeed.
Here's what matters if you're considering buying a home in Kissimmee:
Property Strategy for 34744
Which property type performs best in this market?
📊 Compare All Property Types →
| Type | Median Value | Est. Rent | Cap Rate | 5yr CAGR | $/Bedroom |
|---|---|---|---|---|---|
| 2BR | $271,879 | $1,720 | 4.6% | +7.6% | $135,939 |
| 3BR | $354,088 | $2,160 | 4.4% | +7.5% | $118,029 |
| 4BR | $421,795 | $2,550 | 4.4% | +7.5% | $105,449 |
| 5BR | $507,633 | — | — | +7.7% | $101,527 |
Market Trends
Home Value History (with trend line)
Rent History (with trend line)
📊 How Does 34744 Compare?
| Metric | 34744 | Kissimmee | Orlando-Kissimmee-Sanford, FL | Florida |
|---|---|---|---|---|
| Home Value | $385,787 | $353,498 | N/A | $374,697 |
| 5-Year CAGR | 4.8% | 4.4% | N/A | 7.4% |
| Avg Rent | $2,150 | $2,007 | N/A | - |
| Cap Rate | 4.4% | 4.5% | - | - |
Similar ZIPs Within 25 Miles
Compare other nearby markets to see if a neighbor offers a better fit.
Landlord Ground Truth
Real numbers from people who own or manage rentals in ZIP 34744 (Kissimmee, FL). Anonymous, moderated, never written by AI.
Do you own or manage rentals in ZIP 34744 (Kissimmee, FL)?
~25 seconds · no account needed · your report is anonymous
Property managers serving Osceola County
Manage rentals here? List your business →Towers Property Management provides community association management services to homeowners associations and condominium associations in Central Florida, including Orlando, Altamonte Springs, Oviedo, summary from their website
Paragon Property Services, LLC offers full-service home inspection services in Central Florida, including Lake, Sumter, Seminole, Orange, Osceola, Polk, Pasco, Hernando, Hillsborough, Volusia, and Cit summary from their website
Park Avenue Property Management provides property management services in Orlando and Central Florida. summary from their website
Listings are shown for convenience — Repit doesn’t endorse or vet these companies. Ratings shown come only from email-verified visitors.
📊 Market Snapshot
| Home Value | $385,787 |
| Monthly Rent | $2,150 |
| Price-to-Rent | 15.0:1 |
| 1% Rule | ✗ Fails |
💰 Return Metrics
| Gross Yield | 6.7% |
| Cap Rate | 4.4% |
| 5-Year IRR | 9.2% |
📈 Home Appreciation
| 1-Year | -0.6% ▼ |
| 3-Year CAGR | -0.6% ▼ |
| 5-Year CAGR | +4.8% ▲ |
| 10-Year CAGR | +7.0% ▲ |
🏠 Rent Trends
| 1-Year | +0.2% ▲ |
| 3-Year CAGR | +0.4% ▲ |
| 5-Year CAGR | +4.1% ▲ |
The current 30-yr mortgage rate (6.8%) exceeds the estimated cap rate (4.4%). Financing reduces your cash-on-cash return below the cap rate. Markets like this may still make sense as IRR plays — factoring in appreciation, depreciation, and a future refinance when rates drop.
Run an IRR Analysis →⚠️ Risk Signals
Composite view of factors that can impact a ZIP's stability and your downside risk.
Demographics in 34744
Population: 62,756
Crime & Safety
Crime & Safety Data Coming Soon
We're integrating comprehensive crime statistics including violent crime rates, property crime, and safety scores to help you make informed investment decisions.
Expected: Q1 2025
🎓 Schools in 34744
Schools in This ZIP Code
About Repit School Scores
Traditional school ratings rely heavily on standardized test scores, which often reflect family income more than school quality. Repit takes a different approach.
We evaluate schools based on factors that research shows actually impact educational outcomes:
- Class Size — Smaller classes mean more individual attention
- School Funding — Resources available for programs, staff, and facilities
- Community Factors — Neighborhood characteristics that influence student success
- School Environment — Size, type, and structure
Scores are updated annually using federal education data.
🎓 Nearby Colleges & Universities
Investor Insight: With 2,813 students living off-campus nearby, this area has strong rental demand from the college population.
Frequently Asked Questions
How much does a house cost in Kissimmee, FL?
In Kissimmee, FL the median home value sits at $386K. Against the broader FL market, that reads as reasonable for most investors.
What is the tenant pool like in Kissimmee, FL?
The tenant pool in Kissimmee, FL is solid, supported by local employment and population fundamentals. Rents of $2,150/mo are well-absorbed by the market.
What is the typical vacancy rate in Kissimmee, FL?
Occupancy in Kissimmee, FL runs predictable with elevated vacancy. Well-priced units at $2,150/mo lease on reasonable timelines.
How viable is house hacking in Kissimmee, FL?
House hacking in Kissimmee, FL is a challenging. With home values around $386K and rents at $2,150/mo, owner-occupants can offset a meaningful share of PITI.
Is Kissimmee, FL landlord-friendly?
FL ranks as a landlord-friendly state for landlord-tenant law. Kissimmee generally follows the statewide framework, so landlords face reasonable operating rules.
You know 34744 now. You don’t know where it ranks.
This page stays free — all of it. What one page can’t tell you is how 34744 compares to every other market. Investor ($19/mo) screens every U.S. ZIP by cap rate, the 1% rule, vacancy and landlord climate, and exports your shortlist.
How 34744 ranks in Orlando-Kissimmee-Sanford, FL
Every ZIP in this metro, ranked. Free.
AI Market Advisor
Ask questions about investing in 34744 (Kissimmee)
Community Ratings
What people who’ve spent time here actually say. Not paid reviews.
Be the first to rate 34744 (Kissimmee, FL).
It takes 30 seconds. No signup. Your rating helps everyone who comes here after you.