Market · Kissimmee, Osceola County, Florida
Off-market investment properties in Kissimmee.
Kissimmee pairs one of the fastest-growing counties in Florida with one of its highest distress rates — growth on one side, motivated sellers on the other. That spread between distressed acquisition price and stabilized value is exactly what our investors underwrite for, and we source it off-market: pre-foreclosure, probate, tired-landlord, and wholesale situations delivered to our list before any public listing. Top Investment Properties (TIP), operated by 24propertymanagement.com Inc, a licensed Florida real estate brokerage, sells off-market properties to cash investors across Central Florida.
The market, in numbers
What is the Kissimmee investor market doing in 2026?
Kissimmee is a buyer's market with a growth engine underneath it. The typical city home value is $375,833 (Zillow, April 2026) and Osceola County's median sale price of $384,602 was down 6.2% year over year with homes taking 59 days to sell (Redfin, May 2026) — sellers are negotiating. Underneath the correction, the county grew 23.9% since 2020, easily the fastest in our eight-county footprint (U.S. Census), and NeoCity's advanced-manufacturing build-out gives the local economy a second story beyond tourism.
The distress side is what makes Kissimmee unusual: Florida carried the #1 foreclosure rate in the country in H1 2026 — 1 in 373 housing units (ATTOM) — and Osceola ranked among its top counties for filings in June 2026. For investors on our list, that shows up as a steadier flow of pre-foreclosure and motivated-seller deals than calmer counties produce; for underwriting, it means comps deserve a hard look because the same distress sits in your resale market.
Rents ask for discipline here. The Apartment List Kissimmee median fell 5.9% year over year to $1,385 (May 2026), while county-level Zillow asking rent reads $2,091 (July 2026) — a methodology spread wide enough that the only safe practice is underwriting your specific bedroom count and street, conservatively. Heavy new construction (about 15 permits per 1,000 residents county-wide) is the reason: new supply competes with your rental. Buy below the median with a margin that survives flat rents, and Kissimmee's growth does the rest.
Why investors target Kissimmee
Growth on one side, motivated sellers on the other.
Fastest-growing county
Osceola grew 23.9% since 2020 (U.S. Census) — new residents keep absorbing supply and backstopping every exit strategy.
Distress = deal flow
A top-4 Florida foreclosure county (ATTOM, Jun 2026) in the #1 foreclosure state — motivated-seller situations surface here first.
A real STR path
Clearer vacation-rental rules than most neighbors — in the right zoning, with the right license. Near-attractions demand does the rest.
What pencils here
Which strategies work in Kissimmee right now?
Distress-sourced flips and workforce rentals lead; STR works only in the right zoning.
Run your own numbers — free flip calculator →
Distress-sourced flips
Osceola sits among Florida’s top foreclosure counties (ATTOM, Jun 2026), and Florida flips grossed a median $75,000 at 28.3% ROI in Q1 2026. Buy the workout below retail, keep the scope realistic.
Workforce rentals
The county grew 23.9% since 2020 (U.S. Census) and rent-to-price screens near 6.5% gross county-wide — but rents softened, so underwrite flat rents and check competing new supply before you buy.
STR in the right zoning
Osceola has a clearer vacation-rental path than most neighbors — in the right overlay, with a Florida vacation-rental license and local business-tax receipt. Verify the parcel before underwriting STR income.
Where we source
Active across Kissimmee and its neighbors.
Our Osceola inventory is off-market and cash-only — pre-foreclosure, probate, wholesale, and tired-landlord situations delivered to our investor list before any public listing.
- Kissimmee proper
Tourism-adjacent demand and the county’s deepest rental pool — watch STR overlay zoning parcel by parcel.
- St. Cloud
The fast-growing family market southeast of the metro — newer construction and conventional long-term-rental demand.
- Poinciana
Large, affordable master-planned area for workforce rentals — model the competing new supply honestly.
Full county context — median prices, rents, growth, and the cash-flow read for all of Osceola — lives on our Osceola County market page. Sourcing the employment core instead? See Orlando. Looking west of the parks? See Clermont.
Kissimmee investor FAQ
Straight answers, sourced numbers.
What does an investment property cost in Kissimmee right now?
The typical Kissimmee home value is $375,833 as of April 2026 (Zillow), a touch under the Osceola County median sale price of $384,602 (Redfin, May 2026). County prices were down 6.2% year over year with homes taking 59 days to sell — real negotiating room for cash buyers. Our off-market inventory prices below these retail benchmarks because sellers trade price for a fast, certain, as-is close.
Are short-term rentals allowed in Kissimmee?
In the right zoning, yes — Osceola County offers a clearer vacation-rental path than most Central Florida neighbors, but only inside the proper zoning or overlay, and it requires zoning verification, a Florida vacation-rental license, and a local business-tax receipt. Verify the exact parcel before you underwrite STR income; a long-term-rental fallback number is the honest base case.
Why are investors watching Kissimmee foreclosures in 2026?
Osceola ranked among the top Florida counties for foreclosure filings in June 2026 (ATTOM), in the #1 foreclosure state in the country (1 in 373 units, H1 2026). Distress at that scale is a sourcing tailwind: more pre-foreclosure and motivated-seller situations reach our list as off-market deals, priced for the workout instead of the courthouse steps.
What do Kissimmee rentals actually rent for?
The Apartment List median rent is $1,385 as of May 2026, down 5.9% year over year, while Zillow puts Osceola County’s typical asking rent at $2,091 (July 2026) — different methodologies and unit mixes, so underwrite to the conservative figure for your specific bedroom count and location. Falling rents argue for buying below the median, not for assuming growth.
How do I buy off-market properties in Kissimmee?
Join our investor list and complete your buy-box profile — target areas, price band, property types, strategy. When a Kissimmee deal fits, you get the full deal card (ARV comps, repair estimate, projected returns) before any public listing. Terms are the same on every deal: cash or hard money, as-is, $5,000 non-refundable EMD, 7–21 day close.
Questions about our terms — the $5K EMD, as-is closings, deal access? Read the full investor FAQ →
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