5500 WILLOW BEND TRAIL, KISSIMMEE, FL, 34758
Active114 days on marketListed Apr 7, 2026MLS #S5147335
About this home
5500 WILLOW BEND TRAIL
Tucked away in one of Kissimmee’s most desirable communities, this exceptional property at 5500 Willow Bend Trail offers a rare combination of space, privacy, and breathtaking views. Situated on one of the largest—and arguably the nicest—lots in the neighborhood, this home stands out from the moment you arrive.Inside, you’ll find a home that has been meticulously maintained and thoughtfully cared for, offering a clean, move-in-ready feel throughout. The layout is both functional and inviting, with comfortable living spaces designed for everyday living and effortless entertaining. The kitchen is equipped with brand new stainless steel appliances, adding a modern touch and peace of mind for the next owner.Step outside to your private outdoor retreat featuring a large screened pool cage that fully encloses the pool—perfect for enjoying Florida living year-round. The pool pump is brand new, and the A/C system has also been recently replaced, providing added efficiency and confidence in the home’s major systems. With a roof that’s just 7 years old, the big-ticket items have already been taken care of.What truly sets this home apart is the setting. Overlooking a peaceful lake with a vast conservation area beyond, the backdrop delivers a sense of tranquility and natural beauty that is increasingly hard to find. From the comfort of your screened-in porch, you can regularly enjoy Florida wildlife, including birds and turtles — creating a true connection to nature right in your backyard. Whether you’re enjoying a quiet morning coffee, entertaining guests, or unwinding at sunset, the views here are simply unmatched. The expansive lot provides added privacy and room to breathe, creating a setting that feels both open and secluded.Even better—there is no HOA, giving you added flexibility and freedom, while still offering great amenitities such as a softball field, soccer fields, basketball courts and tennis courts and more.With standout outdoor living, premium lot positioning, major system updates, and unforgettable water and conservation views, 5500 Willow Bend Trail is a rare opportunity you don’t want to miss.
Facts & features
The home at a glance
4
Bedrooms
2.5
Bathrooms
2,847
Sqft
0.2 ac
Lot size
2
Garage
2003
Year built
Two
Levels
$175
Per sqft
Inside
Outside & construction
Community & fees
Utilities & systems
The numbers
What it really costs
Built from this home's actual numbers — the most recent property-tax bill on record — not generic estimates.
$3,660 /mo · 3.5% down FHA, 30-yr fixed at 6%
The assumptions
FHA is the default here because it gets you in the door with just 3.5% down. Switch to Conventional or VA below.
These numbers assume a generic buyer — your credit, down payment and loan program change them. Get the real quote in minutes:
Andrew Acosta
Acosta Home Loans with PRMG · NMLS #1468866
Run your own numbers
Estimated payment
$3,660/mo
Includes FHA mortgage insurance and the financed 1.75% upfront premium. Taxes reflect the most recent bill on record; insurance is a typical-Florida estimate. Your lender’s numbers will differ. CENTURY 21 Edge partners with Florida’s best lenders.
Value check
Is the price right?
The internet’s favorite home-value number comes from a single automated model that has never seen the street, the finishes, or the view — which is why it routinely misses by tens of thousands of dollars. The edgeAI estimate combines multiple independent data sources with our team’s on-the-ground expertise in this exact market.
vs edgeAI estimate
−1.8%
$/sqft vs Kissimmee actives
$175 vs $206
Days on market
114 vs 45 typical
Where $175/sqft sits among the 400 Kissimmee actives
The edgeAI estimate is a starting point, not an appraisal or a broker price opinion. It is generated from public records, listing data and market modeling, and is subject to change once a licensed real estate professional personally inspects the property. Condition, floor, view and lot are not fully captured by any model — ask us for a full comparative market analysis.
The investor lens
Two ways this home pays
This home sits inside Crescent Lakes, a community zoned to allow true short-term rentals — so it can earn as a nightly rental or a traditional lease. Here’s how the two paths compare.
Short-term rental · projected
$52,948/yr gross
Projected nightly rate, occupancy and annual revenue for this exact home.
Long-term rental
$2,150/mo median
Live Kissimmee rental listing data — this home’s rate depends on size, condition and furnishing.
The Florida short-term market
▼ Softening50%
Occupancy
▼ 32% yr/yr
$296
Avg nightly rate
▲ 15% yr/yr
$35K/yr
Revenue per listing
$148
RevPAR
63 days
Booking lead time
5.5 nights
Avg stay
3
Typical min nights
10,047
Active rentals
▲ 12% supply
Seasonality — monthly occupancy
Peaks at 58% in Feb · bottoms at 38% in Jun
Last 12 months of data, January–December, bars scaled to the seasonal peak. Market-wide averages across all home sizes in Florida — the projection above is specific to this home’s size.
Where it sits
Inside Crescent Lakes
Drive times from this address
Estimated driving times, typical traffic. Data © OpenStreetMap contributors.
Crescent Lakes is a short-term-rental community. See the full guide →
Crescent Lakes — neighborhood snapshot
Population
1,871
Median age
40
Median income
$79,955
Median home value
$304,200
Avg household
3
Households w/ children
135
For the school run
Osceola County School District
School assignments and ratings via edgeAI — always verify with the district.
The numbers that matter
The Kissimmee market
$369K → $358K
Kissimmee median sold, yr/yr
97.2%
Sale-to-list ratio (12 mo)
160 of 400
Kissimmee actives have cut their price
Median sold price, Kissimmee, trailing 36 months (3-month rolling) · live MLS data.
This home is listed 86% above the KISSIMMEE 34758 median. See the full Kissimmee market guide →
Paper trail
This home's history
Reality check
What actually sold near 5500 WILLOW BEND TRAIL
Asking prices are opinions — closed sales are facts. The most comparable homes that actually changed hands nearby in the last twelve months.
Sold · May ’26$450,000
5516 WILLOW BEND TRAIL · same community
5 bd · 3 ba · 3,140 sqft · $143/sqft · 8 DOM
Sold · Mar ’26$374,900
2410 WILLOW TREE LANE · same community
4 bd · 3 ba · 2,308 sqft · $162/sqft · 113 DOM
Sold · Mar ’26$415,000
5456 CREPE MYRTLE CIRCLE
4 bd · 2.5 ba · 2,847 sqft · $146/sqft · 10 DOM
Closed-sale data from the MLS, last 12 months, selected for similarity in size and location. No two homes are identical — ask us for a full comparative analysis.
Your home team
The pros in your corner
Buying a home is two conversations — the home and the money. Here’s who handles each, side by side, already working together.
Your agent
David Ramirez
Real Estate Agent · CENTURY 21 Edge
Tours, negotiation, and every question about 5500 WILLOW BEND TRAIL — start here.
Your lender
Andrew Acosta
Acosta Home Loans with PRMG · NMLS #1468866
Pre-approval, rates, and the real monthly number for 5500 WILLOW BEND TRAIL — before you fall in love.
See it in person
Schedule a tour
Pick a day that works — this goes straight to David's phone and CRM.
Straight answers
5500 WILLOW BEND TRAIL FAQs
What would the monthly payment be for 5500 WILLOW BEND TRAIL?+
With 3.5% down on a 30-year FHA loan at 6%, the all-in payment lands around $3,660/mo — principal and interest, the actual property-tax bill and typical Florida insurance. The payment calculator on this page lets you switch loan type (FHA, Conventional, VA) and adjust the down payment, rate and term.
What are the property taxes on 5500 WILLOW BEND TRAIL?+
The most recent tax bill on record (2025) was $4,099. A new owner's bill can differ once the sale price resets the assessed value — we can walk you through what to expect.
Can 5500 WILLOW BEND TRAIL be rented short-term?+
Yes — this home sits inside Crescent Lakes, a community zoned to allow short-term rentals. Nightly-rental income could change the math on this purchase entirely; request a free rental income analysis and our team will prepare projections for this exact home.
Are pets allowed at 5500 WILLOW BEND TRAIL?+
The listing reports pets: Yes. Communities often layer on breed or weight rules — we'll verify the specifics with the association before you commit.
How does the price compare to other homes in Kissimmee?+
At $499,000, this home is listed about 31% above the Kissimmee median of $379,850. The market section on this page shows how the area is trending.
Which schools are assigned to 5500 WILLOW BEND TRAIL?+
Reedy Creek Elementary School (elementary), Poinciana High School (high), Horizon Middle School (middle) — Osceola County School District. Always verify school assignments with the district before relying on them.
The brief
Five things that matter here
01Positioned at the premium end
$499,000 runs 86% above the KISSIMMEE 34758 median — but at 2,847 sqft it's also 57% larger than the typical Kissimmee listing.
02Zoned for nightly rentals
Crescent Lakes is one of the communities zoned to allow true short-term rentals — nightly income could change the math on this purchase entirely. Ask for the free rental analysis below.
03Waterfront living
This home sits directly on the water — the single scarcest feature in Florida inventory and the strongest long-term value anchor.
04Time on market is leverage
114 days on market against a Kissimmee median of 45 — sellers in this position are usually ready to negotiate.
05The price has already moved
Listed at $515,000, now $499,000 — a $16K cut. The full history is in the market section below.
Keep looking
Similar homes nearby
Listing courtesy of RE/MAX HERITAGE PROFESSIONALS · Chris Loschiavo. MLS #S5147335.
IDX information is provided exclusively for consumers’ personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Data is deemed reliable but is not guaranteed accurate by Stellar MLS.
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