Welcome to 5500 Willow Bend Trail - 5500 WILLOW BEND TRL, KISSIMMEE
Formal living room as you enter the home. - 5500 WILLOW BEND TRL, KISSIMMEE
Spacious and connects to the formal dining room - 5500 WILLOW BEND TRL, KISSIMMEE
Plenty of space for entertaining - 5500 WILLOW BEND TRL, KISSIMMEE
Formal dining room at the back of the home. - 5500 WILLOW BEND TRL, KISSIMMEE
View from dining room looking towards the front of the home and the living room - 5500 WILLOW BEND TRL, KISSIMMEE
Kitchen and breakfast bar - 5500 WILLOW BEND TRL, KISSIMMEE
Pendant lighting and new range and refrigerator - 5500 WILLOW BEND TRL, KISSIMMEE
Lots of cabinet space - 5500 WILLOW BEND TRL, KISSIMMEE
Eat in kitchen/dinette at the back of the home. - 5500 WILLOW BEND TRL, KISSIMMEE
Family room at the back of the home with sliders to the back porch and pool - 5500 WILLOW BEND TRL, KISSIMMEE
Again, lots of space for entertaining. - 5500 WILLOW BEND TRL, KISSIMMEE
View from the family room looking towards the slider and pool - 5500 WILLOW BEND TRL, KISSIMMEE
Spacious laundry room - 5500 WILLOW BEND TRL, KISSIMMEE
Primary bedroom - 5500 WILLOW BEND TRL, KISSIMMEE
Another view of the primary bedroom looking towards the ensuite bathroom - 5500 WILLOW BEND TRL, KISSIMMEE
Primary bedroom looking towards the entrance - 5500 WILLOW BEND TRL, KISSIMMEE
Primary bathroom with dual sinks, garden tub and separate shower. - 5500 WILLOW BEND TRL, KISSIMMEE
Shower and separate tub. - 5500 WILLOW BEND TRL, KISSIMMEE
Bedroom 2 is spacious. - 5500 WILLOW BEND TRL, KISSIMMEE
View of bedroom 2 at the back of the home on the 2nd floor. - 5500 WILLOW BEND TRL, KISSIMMEE
Guest bathroom has dual sinks as well. - 5500 WILLOW BEND TRL, KISSIMMEE
3rd bedroom - 5500 WILLOW BEND TRL, KISSIMMEE
Also at the back of the home is this 3rd bedroom - 5500 WILLOW BEND TRL, KISSIMMEE
Den/loft/flex space - 5500 WILLOW BEND TRL, KISSIMMEE
Another view of the flex space, (home theater), playroom, home office? - 5500 WILLOW BEND TRL, KISSIMMEE
So much versatility. - 5500 WILLOW BEND TRL, KISSIMMEE
4th bedroom - 5500 WILLOW BEND TRL, KISSIMMEE
This is towards the front of the home on the 2nd floor. - 5500 WILLOW BEND TRL, KISSIMMEE
Backyard and pool.  Look at that view! - 5500 WILLOW BEND TRL, KISSIMMEE
Lots of space in the screen enclosure. - 5500 WILLOW BEND TRL, KISSIMMEE
Watch the wildlife from your pool. - 5500 WILLOW BEND TRL, KISSIMMEE
Looking at the back of the home. - 5500 WILLOW BEND TRL, KISSIMMEE
Backyard view from the lake. - 5500 WILLOW BEND TRL, KISSIMMEE
Ahh, rest, relaxation and views. - 5500 WILLOW BEND TRL, KISSIMMEE
Water on 2 sides. - 5500 WILLOW BEND TRL, KISSIMMEE
Overview of the home. - 5500 WILLOW BEND TRL, KISSIMMEE
Overhead view of the community. - 5500 WILLOW BEND TRL, KISSIMMEE
Amenities that are included with no HOA fees. - 5500 WILLOW BEND TRL, KISSIMMEE
Get away from the cold and enjoy your community amenities - 5500 WILLOW BEND TRL, KISSIMMEE
Brand new basketball courts - 5500 WILLOW BEND TRL, KISSIMMEE
Tennis courts and other amenities - 5500 WILLOW BEND TRL, KISSIMMEE
Imagine your winters here. - 5500 WILLOW BEND TRL, KISSIMMEE
Entrance to the community. - 5500 WILLOW BEND TRL, KISSIMMEE
Overhead view.  Look at the size of the conservation area across the lake.  Won't be built on. - 5500 WILLOW BEND TRL, KISSIMMEE
Overhead view of the home from the front. - 5500 WILLOW BEND TRL, KISSIMMEE
Welcome home. - 5500 WILLOW BEND TRL, KISSIMMEE
Street entrance. - 5500 WILLOW BEND TRL, KISSIMMEE
5500 Willow Bend Trail - 5500 WILLOW BEND TRL, KISSIMMEE
This gives you a good lay of the land. - 5500 WILLOW BEND TRL, KISSIMMEE
50 photos

$499,000

5500 WILLOW BEND TRL
KISSIMMEE, FL 34758
Listed by Chris Loschiavo · RE/MAX HERITAGE PROFESSIONALS
Bedrooms
4
Bathrooms
2.5
Living area
2,847 sqft
Year built
2003

About this home

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.

Highlights

WaterfrontPrivate pool

Property details

MLS
Stellar MLS
MLS #
MFRS5147335
Property type
Single Family Residence
Subdivision
WILLOW BEND AT CRESCENT LAKES
Status
Active
Days on market
182
On market date
April 7, 2026
Stories
N/A
Total bathrooms
2.5
Garage spaces
2
Parking spaces
N/A
Lot size
0.2 acres
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Nearby schools

Within 10 miles. School directory data from the National Center for Education Statistics (NCES), accessed via the Urban Institute Education Data API. Local Score is calculated by INNOVATE Real Estate; where a state rating is shown, it comes from that state's own official school report card.

Elementary
REEDY CREEK ELEMENTARY SCHOOL
0.8 mi away · Grades -1-5
Nearest school -- attendance-zone data not available here
3.0
Local Score (student-teacher ratio only (preliminary -- will incorporate state test-score data once available)) -- not an official state rating
Enrollment
864
Student:teacher ratio
15.7:1
District
OSCEOLA
Middle
HORIZON MIDDLE SCHOOL
2.58 mi away · Grades 6-8
Nearest school -- attendance-zone data not available here
3.0
Local Score (student-teacher ratio only (preliminary -- will incorporate state test-score data once available)) -- not an official state rating
Enrollment
1,325
Student:teacher ratio
17.9:1
District
OSCEOLA
High
POINCIANA HIGH SCHOOL
0.88 mi away · Grades 9-12
Nearest school -- attendance-zone data not available here
2.0
Local Score (student-teacher ratio only (preliminary -- will incorporate state test-score data once available)) -- not an official state rating
Enrollment
2,442
Student:teacher ratio
22.0:1
District
OSCEOLA

Walkability

Blended score for KISSIMMEE's center, calculated by INNOVATE Real Estate from two sources: the EPA's National Walkability Index (street network, transit, land-use mix) and Google Places amenity data (what's actually reachable on foot from this point). 60% EPA National Walkability Index + 40% nearby-amenity density (Google Places).

44
Somewhat walkable
out of 100
EPA National Walkability Index
9.3 / 20 -- Below average walkable
Google Places amenity density
40 / 100
Restaurants & cafes2
Grocery stores1
Parks1
Schools5
Transit stops4
Pharmacies0

Market position

How this listing compares to current activity in KISSIMMEE, from live MLS data.

On the market 182 days -- 81 more days than KISSIMMEE's current average of 101 days.
For reference, the median list price across 5,299 active listings in KISSIMMEE right now is $314,990.

Mortgage calculator

Estimate only - actual rate and payment depend on your lender, credit, and loan program.

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Est. monthly payment
$3,155/mo
$99,800 down
$399,200 loan
Principal & interest$2,589
Property tax (est.)$416
Home insurance (est.)$150

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Data source: Listing information provided by Stellar MLS (mfrmls) via Trestle/CoreLogic. Last updated 18 days ago.

Information herein deemed reliable but not guaranteed; all measurements, school assignments, HOA fees, taxes, and feature lists are approximate and should be independently verified. Equal Housing Opportunity.